Organic compound and organic light-emitting element

Abstract

This organic compound is represented by general formula (1). In general formula (1), R12 to R32 are each a hydrogen atom or a substituent. Two of R13 to R17 and two of R23 to R27 each have a specific substituent. At least two of R12, R18, R22, and R28 each have a specific substituent.

Description

Organic compound and organic light-emitting device

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

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

[0003] Recent progress in organic light-emitting devices has been remarkable, and their features include low driving voltage, a wide range of emission wavelengths, high-speed response, and the possibility of thinning and reducing the weight of light-emitting devices.

[0004] Incidentally, there has been active research into the creation of compounds suitable for organic light-emitting devices. This is because the creation of compounds with excellent device life is important in providing high-performance organic light-emitting devices. Patent Document 1 describes compound Ref-1, and Patent Document 2 describes compound Ref-2.

[0005]

[0006] International Publication No. 2019 / 111971 U.S. Patent Application Publication No. 2023 / 0322802

[0007] However, all of the above compounds have the problem of being prone to aggregation in films or solutions.

[0008] The present invention has been made in view of the above problems, and an object of the present invention is to provide an organic compound that is less likely to aggregate in a film or solution.

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

[0010]

[0011] In general formula (1), R １２ ~R １８ , R ２２ ~R ２８, R ３１ and R ３２ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. １３ ~R １７ Two of the groups are substituted with general formula (2), and R ２３ ~R ２７ Two of R are substituted with general formula (2). １２ , R １８ , R ２２ , R ２８ At least two of the above are represented by general formula (3) or general formula (4).

[0012]

[0013] In general formula (2), R １１１ ~R １１４ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. X is an oxygen atom, a sulfur atom, or CRR', and R and R' are either a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. * indicates the bonding position with general formula (1).

[0014] In general formulas (3) and (4), R ３０１ , R ３０６ , R ４０１ , R ４０５ , R ４０６ , and R ４１０are each independently selected from the group consisting of a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group, provided that R ４０５ and R ４１０ may be directly bonded. ３０２ , R ３０４ ~R ３０５ , R ４０２ ~R ４０４ , and R ４０７ ~R ４０９ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. ３０１ ~R ３０６ Two adjacent ones of these may be bonded to form a ring. * indicates the bonding position to general formula (1).

[0015] According to the present invention, it is possible to provide an organic compound that is less likely to aggregate.

[0016] FIG. 1 is a schematic cross-sectional view showing an example of a pixel of a display device according to one embodiment of the present invention. FIG. 2 is a schematic cross-sectional view of an example of a display device using an organic light-emitting element according to one embodiment of the present invention. FIG. 3 is a schematic view showing an example of a display device according to one embodiment of the present invention. FIG. 4 is a schematic view showing an example of an imaging device according to one embodiment of the present invention. FIG. 5 is a schematic view showing an example of an electronic device according to one embodiment of the present invention. FIG. 6 is a schematic view showing an example of a display device according to one embodiment of the present invention. FIG. 7 is a schematic view showing an example of a bendable display device. FIG. 8 is a schematic view showing an example of a lighting device according to one embodiment of the present invention. FIG. 9 is a schematic view showing an example of an automobile having a vehicle lamp according to one embodiment of the present invention. FIG. 10 is a schematic view showing an example of an automobile having a display unit according to one embodiment of the present invention. FIG. 11 is a schematic view showing an example of a wearable device according to one embodiment of the present invention. FIG. 12 is a schematic view showing an example of a wearable device according to one embodiment of the present invention, having an imaging device. FIG. 13 is a schematic view of a head-mounted display as a display device according to one embodiment of the present invention. FIG. 14 is a schematic view showing an example in which a display device according to one embodiment of the present invention is connected to an external device. FIG. 15 is a schematic view showing an example of an image forming device according to one embodiment of the present invention. FIG. 16 is a schematic view showing an example of an exposure light source of an image forming device according to one embodiment of the present invention. These are molecular models of compounds A-1, A-3, A-4, Ref-1, and Ref-4 viewed from the horizontal direction.

[0017] In this specification, examples of halogen atoms include, but are not limited to, fluorine, chlorine, bromine, iodine, astatine, tennessine, and the like.

[0018] The alkyl group may be an alkyl group having from 1 to 20 carbon atoms, or from 1 to 10 carbon atoms. Specific examples include, but are not limited to, a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, a tertiary butyl group, a secondary butyl group, an octyl group, a cyclohexyl group, a cyclopentyl group, a tertiary pentyl group, a 3-methylpentan-3-yl group, a 1-adamantyl group, and a 2-adamantyl group. The alkyl group includes a linear alkyl group, a cycloalkyl group, and a branched alkyl group. The linear alkyl group may have from 1 to 20 carbon atoms, or from 1 to 10 carbon atoms. The cycloalkyl group and the branched alkyl group may have from 3 to 20 carbon atoms, or from 3 to 10 carbon atoms. A carbon atom constituting the cycloalkyl group may be substituted with a heteroatom, but in this case, it is preferable that the cycloalkyl group have one heteroatom.

[0019] The alkenyl group may be either an E-alkenyl group or a Z-alkenyl group. The E-alkenyl group and Z-alkenyl group may have from 1 to 20 carbon atoms, from 1 to 10 carbon atoms, or from 1 to 8 carbon atoms.

[0020] The alkynyl group may have from 1 to 20 carbon atoms, from 1 to 10 carbon atoms, or from 1 to 8 carbon atoms.

[0021] The alkoxy group may be an alkoxy group having from 1 to 20 carbon atoms, or may be an alkoxy group having from 1 to 10 carbon atoms. Specific examples include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a tertiary butoxy group, a 2-ethyl-octyloxy group, and a benzyloxy group.

[0022] A silyl group is a group in which the silicon atom has a hydrogen atom or a substituent. The substituent may be a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. The substituted or unsubstituted alkyl group carried by the silicon atom may be a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. The substituted or unsubstituted aryl group carried by the silicon atom may be a substituted or unsubstituted aryl group having 6 to 10 carbon atoms. The silyl group may be a trialkylsilyl group or a triarylsilyl group. Specific examples include, but are not limited to, a trimethylsilyl group and a triphenylsilyl group.

[0023] The aryl group may have from 6 to 20 carbon atoms, from 6 to 18 carbon atoms, or from 6 to 12 carbon atoms. Specific examples include, but are not limited to, a phenyl group, a biphenyl group, a naphthyl group, a phenanthrenyl group, a triphenylenyl group, an indenyl group, a terphenyl group, a fluorenyl group, a pyrenyl group, an anthranyl group, a perylenyl group, a chrysenyl group, and a fluoranthenyl group.

[0024] The heterocyclic group may have from 3 to 24 carbon atoms, from 3 to 18 carbon atoms, or from 3 to 12 carbon atoms. Specific examples include, but are not limited to, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a carbazolyl group, an acridinyl group, and a phenanthrolyl group.

[0025] The amino group may be a substituted amino group substituted with an alkyl group or an aryl group, and may be a substituted amino group substituted with an alkyl group having from 1 to 4 carbon atoms or an aryl group having from 6 to 12 carbon atoms. Specific examples include, but are not limited to, an N-methylamino group, an N-ethylamino group, an N,N-dimethylamino group, an N,N-diethylamino group, an N-methyl-N-ethylamino group, an N-benzylamino group, an N-methyl-N-benzylamino group, an N,N-dibenzylamino group, an anilino group, an N,N-diphenylamino group, an N,N-dinaphthylamino group, an N,N-difluorenylamino group, an N-phenyl-N-tolylamino group, an N,N-ditolylamino group, an N-methyl-N-phenylamino group, an N,N-dianisolylamino group, an N-mesityl-N-phenylamino group, an N,N-dimesitylamino group, an N-phenyl-N-(4-tert-butylphenyl)amino group, an N-phenyl-N-(4-trifluoromethylphenyl)amino group, and an N-piperidyl group.

[0026] Specific examples of the aryloxy group include, but are not limited to, a phenoxy group.

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

[0028] The acyl group is a substituent derived from an alkyl group, and the alkyl group is an alkyl group as defined above.

[0029] The alkoxycarbonyl group is a substituent derived from an alkyl group, and the alkyl group is an alkyl group as defined above.

[0030] The imino group is a substituent derived from a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group, or an aryl group, and the alkyl group and the aryl group are the alkyl group and aryl group described above.

[0031] The sulfanyl group has a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group, or an aryl group, the alkyl group and the aryl group being the alkyl group and the aryl group described above.

[0032] The sulfinyl group is a substituent derived from a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group, or an aryl group, and the alkyl group and the aryl group are the alkyl group and aryl group described above.

[0033] The sulfonyl group is a substituent derived from a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group, or an aryl group, and the alkyl group and the aryl group are the alkyl group and the aryl group described above.

[0034] Examples of substituents that the alkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, aryloxy group, silyl group, aryl group, heterocyclic group, heteroaryloxy group, acyl group, alkoxycarbonyl group, imino group, sulfanyl group, sulfinyl group, and sulfonyl group may further have include, but are not limited to, deuterium, alkyl groups such as methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, and tertiary butyl group, aralkyl groups such as benzyl group, aryl groups such as phenyl group and biphenyl group, heterocyclic groups such as pyridyl group and pyrrolyl group, amino groups such as dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, and ditolylamino group, alkoxy groups such as methoxy group, ethoxy group, and propoxy group, aryloxy groups such as phenoxy group, halogen atoms such as fluorine, chlorine, bromine, and iodine, cyano group, and nitro group.

[0035] (1) Organic Compound First, the organic compound according to the present invention will be explained.

[0036] The organic compound according to this embodiment is a compound represented by general formula (1).

[0037]

[0038] <R １２ ~R １８ , R ２２ ~R ２８ , R ３１ and R ３２ > R １２ ~R １８ , R ２２ ~R ２８ , R３１ and R ３２ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. １３ ~R １７ Two of these are substituted with general formula (2) described below, and R ２３ ~R ２７ Two of R are substituted with general formula (2). １２ , R １８ , R ２２ , R ２８ At least two of the above are represented by general formula (3) or (4) described below, and are preferably represented by general formula (3).

[0039] In the general formula (1), the combination of the bonding positions with the general formula (2) is R １３ ~R １７ Among them, R １３ and R １４ , R １４ and R １５ , or R １６ and R １７ and R ２３ ~R ２７ Among them, R ２３ and R ２４ , R ２４ and R ２５ , or R ２６ and R ２７ R １３ ~R １７ Among them, R １４ and R １５ is substituted in general formula (2), and R ２３ ~R ２７ Among them, R ２４ and R ２５ is preferably substituted with general formula (2).

[0040] Here, for example, "R １３ and R １４ is substituted with general formula (2)" means that R１３ and R １４ represents that the two carbon atoms to which R are bonded are bonded to the * in general formula (2). １５ ~R １７ , R ２３ ~R ２７ The same is true for .

[0041] R １２ and R ２２ , or R １８ and R ２８ is preferably a general formula (3), and R １２ and R ２２ It is more preferable that the general formula (3) is

[0042] R １２ and R ２２ , or R １８ and R ２８ is preferably general formula (4), and R １２ and R ２２ is more preferably represented by general formula (4).

[0043] In general formula (1), R ３１ and R ３２ may be a hydrogen atom. １３ ~R １７ and R ２３ ~R ２７ In the formula (2), the portion not substituted by the general formula (2) may be a hydrogen atom. １６ and R ２６ When does not bond to general formula (2), R １６ and R ２６ is preferably a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. Specifically, it is an alkyl group having 3 or 4 carbon atoms or an aryl group having from 6 to 10 carbon atoms, and is preferably an isopropyl group, a tert-butyl group, or a phenyl group, and more preferably an isopropyl group or a phenyl group.

[0044]

[0045] In general formula (2), * indicates the bonding position to general formula (1).

[0046] <R １１１ ~R １１４ In the general formula (2), R １１１ ~R １１４ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group.

[0047] R １１１ may be a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specifically, it may be a hydrogen atom, an alkyl group having 3 or 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms, and is preferably a hydrogen atom, an isopropyl group, a tert-butyl group, or a phenyl group, more preferably a hydrogen atom or a phenyl group, and particularly preferably a hydrogen atom. １１２ ~R １１４ may be a hydrogen atom.

[0048] Here, in the general formulas (1) and (2), R １５ , R １６ , R ２５ , R ２６ , R １１１ At least two of the groups may be a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and are preferably an isopropyl group or a phenyl group, and more preferably a phenyl group.

[0049] <X> X is an oxygen atom, a sulfur atom, or CRR', and may be an oxygen atom or CRR'. R and R' are either a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0050] X is preferably an oxygen atom or a sulfur atom, more preferably an oxygen atom.

[0051] Furthermore, a plurality of Xs may have the same structure or different structures, but from the viewpoint of ease of synthesis, it is preferable that they have the same structure.

[0052]

[0053] In general formula (3), * indicates the bonding position to general formula (1).

[0054] <R ３０１ ~R ３０６ In the general formula (3), R ３０１ and R ３０６ are each independently selected from the group consisting of a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group.

[0055] R ３０１ and R ３０６ may be each independently selected from the group consisting of an alkyl group having 3 or 4 carbon atoms, an aryl group having from 6 to 24 carbon atoms, a substituted or unsubstituted silyl group, and a cyano group, and may each independently be selected from the group consisting of an isopropyl group, a tert-butyl group, a cyclopropyl group, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, a substituted or unsubstituted silyl group, and a cyano group. In particular, R ３０１ and R ３０６ are preferably each independently selected from the group consisting of an alkyl group having 3 or 4 carbon atoms and an aryl group having 6 to 24 carbon atoms, more preferably each independently selected from the group consisting of an isopropyl group, a cyclopropyl group, a phenyl group, a naphthyl group, and a chain of multiple phenyl groups, and even more preferably an isopropyl group. ３０１ and R ３０６may each be independently selected from the group consisting of an isopropyl group, a tert-butyl group, a cyclopropyl group, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, a substituted or unsubstituted silyl group, and a cyano group. ３０１ and R ３０６ may have the same structure or different structures, but from the viewpoint of ease of synthesis, it is preferable that they have the same structure.

[0056] Here, the chain consisting of a plurality of phenyl groups is the chain consisting of a plurality of phenyl groups in the exemplary compound 13. ３０１ and R ３０６ In the exemplary compound 13, R ３０１ and R ３０６ is a chain consisting of four phenyl groups, but is not limited to this, and may be a chain consisting of two phenyl groups or a chain consisting of three phenyl groups.

[0057] R ３０２ , and R ３０４ ~R ３０５ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group.

[0058] R ３０２ and R ３０５ may be, for example, a hydrogen atom. ３０４ may be a hydrogen atom, an alkyl group having 3 or 4 carbon atoms, or an aryl group having 6 to 24 carbon atoms, and is preferably an isopropyl group. ３０４ is R ３０１ and R ３０６ It is preferred that the compound has the same structure as

[0059] R ３０１ ~R ３０６ Any two adjacent groups among R may be bonded to form a ring. ３０１ ~R３０６ The two adjacent ones are R ３０１ and R ３０２ , R ３０２ and R ３０４ , R ３０４ and R ３０５ , R ３０５ and R ３０６ and R ３０１ and R ３０２ , and R ３０５ and R ３０６ may each form a ring. ３０１ ~R ３０６ The ring formed by bonding of adjacent two of R may be a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, and may form a substituted or unsubstituted phenyl group. More specifically, Exemplary Compound 7 described later has R ３０１ and R ３０２ , and R ３０５ and R ３０６ Each of these forms a phenyl group having a methyl group. ３０１ and R ３０６ is an unsaturated branched alkyl group having 3 carbon atoms. From the viewpoint of ease of synthesis, R ３０１ ~R ３０６ It is preferred that adjacent two of these do not form a ring.

[0060]

[0061] In general formula (3), * indicates the bonding position to general formula (1).

[0062] <R ４０１ ~R ４１０ In the general formula (4), R ４０１ , R ４０５ , R ４０６ , and R ４１０ are each independently selected from the group consisting of a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group, provided that R ４０５ and R ４１０may be directly bonded. Specifically, the general formula (4) may be a substituent derived from a carbazolyl group.

[0063] R ４０１ , R ４０５ , R ４０６ , and R ４１０ may be each independently selected from the group consisting of an alkyl group having 3 or 4 carbon atoms, an aryl group having from 6 to 24 carbon atoms, a substituted or unsubstituted silyl group, and a cyano group, and may each independently be selected from the group consisting of an isopropyl group, a tert-butyl group, a cyclopropyl group, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, a substituted or unsubstituted silyl group, and a cyano group. In particular, R ４０１ , R ４０５ , R ４０６ , and R ４１０ are preferably each independently selected from the group consisting of an alkyl group having 3 or 4 carbon atoms and an aryl group having 6 to 24 carbon atoms, more preferably each independently selected from the group consisting of an isopropyl group, a cyclopropyl group, a phenyl group, a naphthyl group, and a chain of multiple phenyl groups, and even more preferably an isopropyl group. ４０１ , R ４０５ , R ４０６ , and R ４１０ may each be independently selected from the group consisting of an isopropyl group, a tert-butyl group, a cyclopropyl group, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, a substituted or unsubstituted silyl group, and a cyano group.

[0064] R ４０５ and R ４１０ Similarly, when R ４０１ and R ４０５ Examples of the substituents include the above-mentioned substituents. ４０１ and R ４０５are preferably each independently selected from the group consisting of an alkyl group having 3 or 4 carbon atoms and an aryl group having from 6 to 24 carbon atoms, more preferably each independently selected from the group consisting of an isopropyl group, a cyclopropyl group, a phenyl group, a naphthyl group, and a chain of multiple phenyl groups, and even more preferably an isopropyl group.

[0065] R ４０１ , R ４０５ , R ４０６ , and R ４１０ , or R ４０１ and R ４０５ may have the same structure or different structures, but from the viewpoint of ease of synthesis, it is preferable that they have the same structure.

[0066] R ４０２ ~R ４０４ and R ４０７ ~R ４０９ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. ４０２ ~R ４０４ and R ４０７ ~R ４０９ may be a hydrogen atom.

[0067] The organic compound represented by general formula (1) is preferably an organic compound represented by general formula (5).

[0068]

[0069] <R ２１１ ~R ２１４ , R ２２１ ~R ２２４ In the general formula (5), R ２１１ ~R ２１４ , R ２２１ ~R ２２４are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. ２１１ ~R ２１４ , R ２２１ ~R ２２４ may each be a hydrogen atom. １２ , R １３ , R １６ ~R １８ , R ２２ , R ２３ , R ２６ ~R ２８ , X are as described above, and X may be the same or different. From the viewpoint of ease of synthesis, it is preferable that X are the same.

[0070] The structure of the organic compound according to this embodiment will be described below.

[0071] The organic compound according to this embodiment is R １２ , R １８ , R ２２ , R ２８ By having a substituent represented by general formula (3) or (4) in at least two of the above, the organic compound becomes less likely to aggregate.

[0072] The mechanism by which the above-described structure provides the effects of the present invention will be described below. The skeleton represented by general formula (1) alone is generally referred to as an indolocarbazole skeleton. The central benzene ring and its periphery in the indolocarbazole skeleton have a particularly highly planar structure. In addition, when X in general formula (2) is an oxygen atom or a sulfur atom, the structure of general formula (2) also has a high degree of planarity. Therefore, organic compounds composed of general formulas (1) and (2) have a structure in which indolocarbazoles tend to aggregate together due to the high planarity of the central benzene ring of the indolocarbazole skeleton and its periphery, and the structural portion of general formula (2).

[0073] Therefore, the organic compound according to this embodiment is R １２ , R １８ , R ２２ , R ２８ The organic compound according to this embodiment is characterized in that at least two of the above are substituents represented by general formula (3) or (4). The substituent represented by general formula (3) has bulky substituents at both ortho positions relative to the position marked with *. By having bulky substituents at the ortho positions, a structure is formed in which the substituents cover the indolocarbazole skeleton. Furthermore, by arranging the substituents so as to cover particularly planar portions of the organic compound represented by general formulas (1) and (2), aggregation of indolocarbazoles can be reduced. As a result, the organic compound according to this embodiment is an organic compound that is less likely to aggregate.

[0074] 8A to 8C show the structural formulas and horizontally viewed molecules of organic compounds A-1, A-3, and A-4 according to this embodiment, and comparative examples Ref-1 and Ref-4. Comparing A-1 and Ref-1, it is clear that in Ref-1, the substituents do not sufficiently cover the indolocarbazole skeleton, whereas in A-1, bulky substituents are arranged to cover the indolocarbazole skeleton. Therefore, compared to Ref-1, A-1 can reduce aggregation of indolocarbazole molecules. Similar trends can be confirmed when comparing A-2, in which X is a sulfur atom in general formula (2), with Ref-1, or when comparing A-4 with Ref-4.

[0075] Next, in order to quantitatively confirm the effect of the organic compound according to this embodiment, the cohesive energy density of each compound was calculated. The cohesive energy density is known as a parameter that indicates the tendency of an organic compound to aggregate. The higher the cohesive energy density value, the more likely the organic compounds are to aggregate together, and the lower the value, the less likely the organic compounds are to aggregate together. In this embodiment, the cohesive energy density is 30 kcalmol －１ nm －３ may be less than 25 kcalmol －１ nm －３ may be less than or equal to 23 kcalmol －１ nm－３ may be less than 20 kcalmol －１ nm －３ It may be the following:

[0076] The cohesive energy density was calculated using the following formula (1): cohesive energy density = cohesive energy / molecular volume (1)

[0077] The cohesive energy was calculated using the PMF (Potential of Mean Force) calculated by molecular dynamics. GROMACS can be used as software for the molecular dynamics.

[0078] When performing calculations using molecular dynamics, parameters for defining the interactions between atoms are set in advance. GAFF (General Amber force field), which is generally used for calculations of organic molecules, is used. The charge assigned to each atom is set using quantum chemical calculations. A geometry optimization calculation is performed using B3LYP as the functional and 6-31G* as the basis function, and MK (Merz-Kollman-Singh) charges are fitted to the most stable structure.As computational software for quantum chemical calculations, for example, Gaussian 16, Revision C.01 (Gaussian 16, Revision C.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. V. Marenich, J. Bloino, B. G. Janesko, R. Gompertz, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasagawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery, Jr., J. E. Peralta, F. Oglialoro, M. J. Bearpark, J. J. Heyd, E. N. Brothers, K. N. Kudin, V. N. Staroverov, T. A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. P. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cami, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2019.) can be used.The fitting of MK charges is described in B. H. Besler, et al., J. Comp. Chem. 11, 431 (1990) and U. C. Singh, et al., J. Comp. Chem. 5, 129 (1984).

[0079] The PMF is calculated using the umbrella sampling method. First, equilibrium and production calculations are performed under isothermal and isobaric conditions for multiple prepared windows. Then, analysis is performed using the WHAM (Weighted Histogram Analysis Method) to obtain a PMF potential curve. Additionally, because the degrees of freedom of the molecules differ at each intermolecular distance, an entropy correction term 2kTln(r) is added. Here, k is the Boltzmann constant, T is the absolute temperature, r is the distance between two molecules, and ln is the natural logarithm. Using the corrected PMF, the cohesive energy is calculated from the difference between the maximum and minimum energies. The PMF calculation method is described in J. S. Hub, et al., J Chem Theory Comput 6.12.3713-3720 (2010). In this calculation, the window step was set to 0.05 nm from the viewpoint of calculation accuracy.

[0080] The molecular volume is calculated by quantum chemical calculation, and the cavity volume used when calculating the SMD model of the SCRF (Self-consistent reaction field) method is used. The SMD model is described in A. V. Marenich, et al. J. Phys. Chem. B, 113.18.6378-6396 (2009).

[0081] Tables 1-1 and 1-2 show the cohesive energy densities of organic compounds A-1 to A-4 according to this embodiment and comparative examples Ref-1 to Ref-5. Note that A-1 is exemplary compound 21, A-2 is exemplary compound 15, A-3 is exemplary compound 5, and A-4 is exemplary compound 11.

[0082]

[0083]

[0084] As can be seen from Tables 1-1 and 1-2, the cohesive energy density of the organic compound according to this embodiment is lower than that of the organic compound according to the comparative example. This is thought to be because the substituent bonded to the indolocarbazole skeleton has a bulky substituent at the ortho position, which allows it to cover the highly planar portion of the indolocarbazole skeleton. Therefore, the organic compound according to this embodiment is a compound that is less likely to aggregate.

[0085] Here, the effects achieved by the organic compound being less likely to aggregate will be described. A film using an organic compound that is less likely to aggregate is less likely to crystallize, resulting in more uniform film quality. When organic compounds are less likely to aggregate, the generation of crystal grain boundaries, trap levels, and quenchers associated with microcrystallization is less likely to occur, and energy transfer from the host material to the guest material is more likely. Furthermore, when the organic compound according to this embodiment is used as a guest material, an emitting layer in which guest materials are dispersed can be formed. As a result, concentration quenching due to aggregation of guest materials can be reduced, making it possible to provide an organic light-emitting element with excellent luminous efficiency.

[0086] Among the organic compounds according to this embodiment, A-2 in particular exhibited a low cohesive energy density. This is thought to be because A-2 has another substituent in addition to the substituent represented by general formula (3) or (4). Furthermore, A-2 has a structure similar to that of R in general formula (1). １６ and R ２６ As described above, the organic compound consisting of the general formulas (1) and (2) has a high planarity in the portion of the general formula (2). １６ and R ２６ The substituent makes the portion of general formula (2) a bulky structure. As a result, it is thought that the intermolecular stacking of indolocarbazole molecules can be further reduced, resulting in a lower cohesive energy density.

[0087] For the above reasons, the organic compound according to this embodiment is an organic compound that is unlikely to aggregate, and therefore, when this compound is used in an organic light-emitting element, an organic light-emitting element with excellent luminous efficiency can be obtained.

[0088] Furthermore, in the general formula (1), R １２ , R １８ , R ２２ , R ２８ When at least two of the above are represented by the general formula (3), the film is less likely to aggregate, resulting in a more excellent shape of the emission spectrum. Specifically, this is preferred because the amount of light emitted in the wavelength region of 430 nm or less is extremely reduced.

[0089] Specific examples of organic compounds according to this embodiment are shown below. However, the present invention is not limited to these. Among the following exemplary compounds, exemplary compounds 5, 11, 15, and 21 are preferred, and exemplary compounds 15 and 21 are more preferred.

[0090]

[0091]

[0092] (2) Organic Light-Emitting Element Next, the organic light-emitting element according to this embodiment will be described. The organic light-emitting element according to this embodiment 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 is preferably contained in the light-emitting layer.

[0093] When the organic compound layer is a laminate consisting of multiple layers, the organic compound layer may have, in addition to the light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole / exciton blocking layer, an electron transport layer, an electron injection layer, etc. The light-emitting layer may be a single layer or a laminate consisting of multiple layers. When the light-emitting layer is a multiple-layer structure, a charge generation layer may be provided between the light-emitting layers.

[0094] The charge generation layer may contain a compound exhibiting a LUMO (Lowest Unoccupied Molecular Orbital) energy level lower than the LUMO energy level of the hole transport layer. The charge generation layer may also contain a compound exhibiting a LUMO (Highest Occupied Molecular Orbital) energy level lower than the HOMO (Highest Occupied Molecular Orbital) energy level of the hole transport layer. Here, the HOMO and LUMO energy levels of the charge generation layer may be the HOMO and LUMO energy levels of the organic compound that constitutes the largest weight ratio of the charge generation layer. The same applies to the hole transport layer and other organic compound layers.

[0095] Here, the closer the HOMO energy level and LUMO energy level are to the vacuum level, the higher they are described as being. The LUMO energy level of the charge generation layer being lower than the HOMO energy level of the hole transport layer means that the LUMO energy level of the charge generation layer is farther from the vacuum level than the HOMO energy level of the hole transport layer.

[0096] In this specification, the HOMO energy level and the LUMO energy level can be calculated using molecular orbital calculations. The molecular orbital calculations may be performed using density functional theory (DFT) or the like, using the B3LYP functional and the 6-31G* basis function or the like.The molecular orbital calculation can be performed, for example, using Gaussian09 (Gaussian09, Revision C.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasagawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gompertz, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2010.).

[0097] The HOMO energy level and LUMO energy level herein can be calculated using the ionization potential and band gap. The HOMO energy level can be estimated by measuring the ionization potential. The ionization potential can be measured by dissolving the compound to be measured in a solvent such as toluene, or by forming a vapor-deposited film of the compound to be measured on a substrate such as glass, and then measuring it with a measuring device such as an AC-3. The band gap can be measured by dissolving the compound to be measured in a solvent such as toluene and irradiating it with excitation light. The band gap can be measured by measuring the absorption edge of the absorption spectrum of the excitation light. Alternatively, the compound to be measured can be vapor-deposited on a substrate such as glass, and then irradiating the vapor-deposited film with excitation light. The band gap can be measured by measuring the absorption edge of the absorption spectrum where the vapor-deposited film absorbs excitation light.

[0098] The LUMO energy level can be calculated using the band gap and the ionization potential value. The LUMO energy level can be estimated by subtracting the ionization potential value from the band gap.

[0099] The LUMO energy level can also be estimated from the reduction potential. For example, the one-electron reduction potential is estimated using CV (cyclic volmetry) measurement. CV measurement is performed, for example, in a 0.1 M tetrabutylammonium perchlorate solution in DMF, and a Ag / Ag reference electrode is used. ＋ Measurements can be performed using a Pt counter electrode and a glassy carbon working electrode. The LUMO energy level can be estimated by adding -4.8 eV, the difference between the reduction potential of the obtained compound and that of ferrocene, to the reduction potential of the compound.

[0100] In the organic light-emitting device according to one embodiment of the present invention, when the organic compound according to the present invention is contained in the light-emitting layer, the light-emitting layer may be a layer consisting of only the organic compound according to the present invention, or may be a layer consisting of the organic compound according to the present invention and other compounds.

[0101] Here, when the light-emitting layer is a layer composed 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 guest material or a host material in the light-emitting layer. Here, the host material is also called a "host" or a "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 a "guest," "dopant material," "dopant," or a "second compound," and is a compound with a mass ratio smaller than that of the host among the compounds constituting the light-emitting layer, and is the compound that is primarily responsible for emitting light. Therefore, the guest material is sometimes also called an emitting material. The assist material is also called an "assist" or a "third compound," and is a compound with a mass ratio smaller than that of the host among the compounds constituting the light-emitting layer, and assists the guest in emitting light.

[0102] The host material is not particularly limited, but is preferably an organic compound represented by general formula (6).

[0103]

[0104] In general formula (6), A １ or A １０ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group.

[0105] <A １ or A ２ > The 9th and 10th positions of anthracene are the most reactive substitution positions in anthracene, so １ or A ２ is preferably a substituent. When the carbon atom at this position has a hydrogen atom, a deuterium atom, or a halogen atom, the 9th and 10th positions of anthracene are likely to react with the organic compound or impurities contained in the organic compound layer during operation of the organic light-emitting device. As a result, a quencher is likely to be produced.

[0106] When the organic compound represented by general formula (6) has substituents other than hydrogen atoms, deuterium atoms, or halogen atoms at the carbon atoms at the 9th and 10th positions, the reaction between the carbon atoms at the 9th and 10th positions of anthracene and the organic compound or impurities contained in the organic compound layer can be reduced. As a result, the generation of quenchers can be reduced, and the organic compound represented by general formula (6) has excellent stability. Therefore, the organic light-emitting device according to this embodiment is preferable because it exhibits excellent device life.

[0107] A １ or A ２ are preferably each independently selected from the group consisting of a substituted or unsubstituted aryl group and a substituted or unsubstituted heterocyclic group. １ or A ２ One of the groups may be a substituted or unsubstituted aryl group, and the other may be a substituted or unsubstituted heterocyclic group. The aryl group may be an aryl group having from 6 to 24 carbon atoms, and the heterocyclic group may be a heterocyclic group having from 5 to 12 carbon atoms. More preferably, the aryl group is a phenyl group, a naphthyl group, or a chain consisting of at least one phenyl group and a naphthyl group, and the heterocyclic group is benzofuran, benzothiophene, dibenzofuran, or dibenzothiophene. More preferably, it is a chain consisting of one to four phenyl groups, or dibenzofuran.

[0108] <A ３ or A １０ > A ３ or A １０ are not particularly limited, and may each be independently selected from the group consisting of a hydrogen atom, a deuterium atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 10 carbon atoms, a heterocyclic group having 5 to 12 carbon atoms, and a cyano group. ３ or A １０ may each be independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 10 carbon atoms, or may be a hydrogen atom.

[0109] More preferred structures of the organic compound represented by general formula (6) are shown below. The organic compound represented by general formula (6) is preferably represented by general formula (7), and more preferably represented by general formula (7-1).

[0110]

[0111] In the general formulas (7) and (7-1), R １ ~R ２０ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted acyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted imino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted sulfanyl group, a substituted or unsubstituted sulfinyl group, a substituted or unsubstituted sulfonyl group, and a cyano group. X is an oxygen atom or a sulfur atom, and is preferably an oxygen atom. However, R １６ ~R ２０ One of the formulas is any one of general formulas (8) to (10).

[0112]

[0113] In the general formulas (8) to (10), R ２１ ~R ２９are 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 aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted acyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted imino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted sulfanyl group, a substituted or unsubstituted sulfinyl group, a substituted or unsubstituted sulfonyl group, and a cyano group. * indicates the bonding position with general formula (7) or (7-1). When the structures represented by general formulas (8) to (10) have aryl groups, it is preferable that the number of the aryl groups is 1 to 4.

[0114] Here, when the general formula (7) and (7-1) have the general formula (8), the general formula (8) is R １６ , R １７ , R １９ , or R ２０ When general formula (7) has general formula (9), general formula (9) is preferably R １６ , R １７ , R １９ , or R ２０ When the general formula (7) has the general formula (10), the general formula (10) is preferably R １７ or R １９ It is preferred that the nucleotide sequence binds to either of the following:

[0115] In the general formulas (7) and (7-1), R １ ~R ２０ may be 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 alkoxy group, a substituted or unsubstituted amino group, and a cyano group. １ ~R ２０are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, an alkyl group having from 1 to 6 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, an amino group having an alkyl group having from 1 to 6 carbon atoms, and a cyano group. For example, R １ ~R １５ may be a hydrogen atom. Particularly preferably, R １ ~R １８ , R １９ ~R ２０ , R ２１ ~R ２８ is a hydrogen atom, and R １９ is the general formula (9).

[0116] In the general formulas (8) to (10), R ２１ ~R ２９ may be 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 alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, and a cyano group. ２１ ~R ２９ are preferably each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, an alkyl group having from 1 to 6 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, an aryl group having from 6 to 30 carbon atoms, a heterocyclic group having from 3 to 12 carbon atoms, an amino group having an alkyl group having from 1 to 6 carbon atoms, an amino group having a phenyl group, and a cyano group. Specific examples include a hydrogen atom, a deuterium atom, a fluorine atom, a tert-butyl group, a hexyl group, a cyclopentyl group, an alkoxy group derived from a cyclohexyl group, an amino group having an isopropyl group, an amino group having a methyl group, an amino group having a cyclohexyl group, a phenyl group, a chain consisting of multiple phenyl groups, a naphthyl group, a fluorenyl group, a phenanthrenyl group, and a pyrenyl group. The chain consisting of multiple phenyl groups may be a chain consisting of from 1 to 6 phenyl groups, a chain consisting of from 1 to 5 phenyl groups, or a chain consisting of from 1 to 4 phenyl groups. In addition, R ２１ ~R ２９In another aspect, any one of R ２１ ~R ２９ may not have an aryl group, and R ２１ ~R ２９ may be a hydrogen atom.

[0117] Specific examples of the organic compound represented by general formula (7) are shown below.

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133] The organic compound according to the present embodiment may be used as a composition containing the organic compound according to the present embodiment and another material different from the organic compound according to the present embodiment. The other material may be, for example, a guest material.

[0134] Here, the lowest excited singlet energy of the host material is S1(H), the lowest excited singlet energy of the guest material is S1(D), and the lowest excited singlet energy of the assist material is S1(A). The organic compound according to the present invention may be any of a guest material, a host material, and an assist material, but is preferably a guest material. In this case, the organic light-emitting element according to this embodiment preferably satisfies S1(H)>S1(D). Furthermore, when the organic light-emitting element according to this embodiment has an assist material, it also preferably satisfies S1(A)>S1(D). When the lowest excited singlet energy of the compound contained in the organic light-emitting element according to this embodiment satisfies the above relationship, excitons can be efficiently transferred to the guest material, resulting in an organic light-emitting element with better luminous efficiency.

[0135] When the organic compound according to the present invention is used in the light-emitting layer, the concentration of the organic compound according to the present invention may be 0.01% by mass or more and 20% by mass or less, and preferably 5% by mass or more and 10% by mass or less, based on the total mass of the light-emitting layer.

[0136] The light-emitting layer may be a single layer or multiple layers, and it is also possible to mix colors by including light-emitting materials having other emitting colors. Multiple layers means that a light-emitting layer and another light-emitting layer are stacked. In this case, the emitting color of the organic light-emitting element is not limited to a single color. More specifically, it may be white or an intermediate color. In the case of white, when the light-emitting layer emits blue light, 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 film formation.

[0137] The organic compound according to the present invention can be used as a constituent material of an organic compound layer other than the light-emitting layer constituting the organic light-emitting device according to this embodiment. Specifically, it may be used as a constituent material of an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, a hole blocking layer, etc. In this case, the emission color of the organic light-emitting device is not limited to a single color. More specifically, it may emit white light or an intermediate color.

[0138] Here, blue light is light whose emission spectrum has a peak wavelength of 430 nm or more and 480 nm or less, green light is light whose emission spectrum has a peak wavelength of 500 nm or more and 550 nm or less, and red light is light whose emission spectrum has a peak wavelength of 580 nm or more and 650 nm or less.

[0139] (3) Other Materials In addition to the materials described above, conventionally known low-molecular-weight and high-molecular-weight hole-injecting or hole-transporting compounds, host compounds, light-emitting compounds, electron-injecting or electron-transporting compounds, etc. may also be used in the production of the organic light-emitting device according to this embodiment, as needed. Examples of these compounds are listed below.

[0140] As the hole injection and transport material, a material with high hole mobility is preferred so that holes can be easily injected from the anode and the injected holes can be transported to the light-emitting layer. Furthermore, a material with a high glass transition temperature is preferred to reduce deterioration of film quality, such as crystallization, in organic light-emitting devices. Examples of low-molecular-weight and high-molecular-weight materials with hole injection and transport properties include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, triazole derivatives, oxadiazole derivatives, imidazole derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, polyarylamine derivatives, polyvinylcarbazole derivatives, polythiophene derivatives, conductive polymers such as PEDOT:PSS, and copolymers or mixtures thereof. Furthermore, the above-mentioned hole injection and transport materials are also suitable for use in electron blocking layers. Specific examples of compounds that can be used as hole injection and transport materials are listed below, but of course, the present invention is not limited to these.

[0141] HT20 is a material called PEDOT:PSS, and SO ３ － It is a compound in which an electron is bonded to a thiophene radical.

[0142]

[0143]

[0144] Specific examples of compounds that can be used as light-emitting materials are shown below, but the present invention is not limited to these.

[0145]

[0146]

[0147]

[0148] Further, examples of the luminescent compound include the following organometallic complexes. The organometallic complex is a compound capable of emitting light from a triplet excited state. While there are no particular limitations on the organometallic complex as long as it emits light from a triplet excited state, it is preferably an organometallic complex containing a ligand and at least one metal selected from iridium, platinum, osmium, gold, copper, rhenium, and ruthenium. The ligand preferably has an orthometal bond. In terms of high phosphorescence quantum yield and the ability to further improve the external quantum efficiency of the light-emitting device, metal complexes containing a metal atom selected from iridium, osmium, and platinum are preferred. Metal complexes such as iridium complexes, osmium complexes, and platinum complexes are more preferred, and orthometallated iridium complexes are even more preferred. Specific examples of compounds used as organometallic complexes are shown below, but of course, are not limited to these.

[0149]

[0150] Examples of host materials or assist materials contained in the light-emitting layer include aromatic hydrocarbon compounds or derivatives thereof, as well as polymers such as carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, triazine derivatives, organoaluminum complexes such as tris(8-quinolinolato)aluminum, organic beryllium complexes, polyphenylene derivatives, polyphenylenevinylene derivatives, polyfluorene derivatives, and polyvinylcarbazole derivatives, as well as copolymers or mixtures thereof. Specific examples of compounds used as assist materials contained in the light-emitting layer are shown below, but the present invention is not limited to these.

[0151]

[0152]

[0153]

[0154] The electron transport material can be arbitrarily selected from those capable of transporting electrons injected from the cathode to the light-emitting layer, and is selected taking into consideration the balance with the hole mobility of the hole transport material. Examples of materials having electron transport properties include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organoaluminum complexes, and fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the above electron transport materials are also suitable for use in hole-blocking layers. Specific examples of compounds usable as electron transport materials are listed below, but of course, are not limited to these.

[0155]

[0156] The electron injection material can be arbitrarily selected from those that allow easy electron injection from the cathode, and is selected in consideration of the balance with hole injection properties, etc. Organic compounds include n-type dopants and reducing dopants. Examples include compounds containing alkali metals such as lithium fluoride, lithium complexes such as lithium quinolinol, benzimidazolidene derivatives, imidazolidene derivatives, fulvalene derivatives, and acridine derivatives.

[0157] It can also be used in combination with the above electron transporting material.

[0158] (4) Ink Composition The ink composition of this embodiment contains the organic compound of this embodiment. The ink composition may contain various additives, such as a charge transport material, a resin, a plasticizer, an antioxidant, and an ultraviolet absorber, as needed. Among these, it is preferable to contain a resin or a charge transport material (for example, an electron transport material).

[0159] The resin is preferably a resin serving as a binder. Specific examples include polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, and urea resin. The resin may be a homopolymer or a copolymer, and one or more types of resins may be used.

[0160] Known materials can be used as the electron transport material. For example, 1,3-bis[2-(4-tert-butylphenyl)-1,3,4-oxadiazo-5-yl]benzene can be mentioned. Commercially available electron transport materials (for example, trade name "OXD-7", manufactured by Lumnessence Technology) can also be used. The content (ppm) of the electron transport material in the luminescent composition is preferably 10 ppm or more and 5,000 ppm or less, based on the total mass of the luminescent composition.

[0161] The ink composition according to this embodiment may use an organic solvent as the solvent. There are no particular limitations on the organic solvent as long as it can dissolve or disperse the organic compound of this embodiment. In particular, it is preferable to use an organic solvent having a boiling point of 70°C or higher and 300°C or lower at 1 atmosphere. The content of the organic solvent in the ink composition is preferably 85% by mass or higher and 95% by mass or lower with respect to the entire ink composition. The ink composition preferably contains an organic compound represented by general formula (1) and an organic compound represented by general formula (6). Among the organic compounds represented by general formula (6), R １７ or R １９ It is preferable that the organic compound is an organic compound which is bonded to the general formula (9) by the following formula.

[0162] Specific examples of organic solvents include toluene, o-xylene, p-xylene, mesitylene, diethyl ether, dibutyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, anisole, 4-methylanisole, phenylcyclohexane, dimethoxyethane, diethylene glycol dimethyl ether, ethyl acetate, butyl acetate, methyl benzoate, cyclopentanone, cyclohexanone, dimethylformamide, dimethylacetamide, methyl ethyl ketone, N-methylpyrrolidone, dimethylimidazolidinone, etc. One or more organic solvents can be used in order to adjust various properties such as the compatibility of various materials in the luminescent composition, and the viscosity and surface tension of the liquid.

[0163] (5) Manufacturing Method of Organic Light-Emitting Device The manufacturing method of the organic light-emitting device of this embodiment includes a step of applying the organic compound of this embodiment to a substrate. This step may be a step of applying the organic compound of this embodiment to the substrate by a coating method or a printing method.

[0164] A method for manufacturing an organic light-emitting device having organic compound layers (such as a hole injection layer, a hole transport layer, an electron blocking layer, an emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer) will be described below. The organic light-emitting device is manufactured by a manufacturing method including a step of applying the organic compound of this embodiment to a substrate to form an organic compound layer.

[0165] Examples of methods for forming an organic compound layer include dry processes and wet processes. Examples of dry processes include vacuum deposition, ionization deposition, sputtering, and plasma deposition. Examples of wet processes include coating methods such as spin coating, casting, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, capillary coating, and slit coating, and printing methods such as screen printing, flexographic printing, offset printing, and inkjet printing. Among these, vacuum deposition, ionization deposition, spray coating, slit coating, or inkjet deposition is preferred from the viewpoint of achieving both film uniformity in thin film formation with a thickness of several nanometers and large-area pixel formation. Among these, when an organic compound highly soluble in organic solvents is used, spray coating, slit coating, and inkjet deposition can be used.

[0166] The wet process will now be described in detail. The wet process is a method in which the ink composition according to this embodiment is applied to a substrate by a known method, and an organic compound layer is formed by drying the organic solvent after the layer is formed. Drying conditions can be appropriately set depending on the constituent materials of the organic compound layer, etc., but drying is preferably performed under an air or inert gas (nitrogen, argon, etc.) atmosphere. The heating temperature for drying is preferably 100°C or higher and 250°C or lower, and more preferably 110°C or higher and 200°C or lower. The heating time for drying is preferably 5 minutes or higher and 60 minutes or lower. The pressure during heating for drying may be normal pressure (1 atmosphere) or reduced pressure (100 Pa to 0.1 MPa). The various conditions (temperature, pressure, and time) in the drying step may be set so as to remove the organic solvent from the organic compound layer, etc.

[0167] When an organic compound layer is formed by a wet process using the ink composition according to this embodiment, it is preferable to appropriately determine the composition. Examples of solid components constituting the organic compound layer include the organic compound according to this embodiment and organometallic complexes.

[0168] When the ink composition according to this embodiment is applied to a substrate by an inkjet method to form an organic compound layer, it is preferable to appropriately control the physical properties of the ink composition. The surface tension of the ink composition at 25°C is preferably 15 mN / m or more and 75 mN / m or less, and more preferably 25 mN / m or more and 45 mN / m or less. The surface tension of the ink composition can be adjusted by appropriately determining the type and content of the organic solvent in the ink composition. Furthermore, the viscosity of the ink composition at 25°C is preferably 0.1 mPa·s or more and 20.0 mPa·s or less, and more preferably 0.5 mPa·s or more and 10.0 mPa·s or less. By setting the viscosity within the above range, clogging and ejection defects in the liquid ejection head when ejecting by the inkjet method can be suppressed.

[0169] (6) Structure of the Organic Light-Emitting Element Hereinafter, the components that make up the organic light-emitting element of this embodiment will be described.

[0170] The organic light-emitting element is provided by forming an insulating layer, a first electrode, an organic compound layer, and a second electrode on a substrate. A protective layer, a color filter, a microlens, etc. may be provided on the second electrode. When a color filter is provided, a planarizing layer may be provided between the color filter and the protective layer. The planarizing layer may be made of an acrylic resin, etc. The same applies when a planarizing layer is provided between the color filter and the microlens.

[0171] [Substrate] Examples of the substrate include quartz, glass, silicon wafer, resin, and metal. Furthermore, the substrate may be provided with a switching element such as a transistor and wiring, and an insulating layer thereon. The insulating layer may be made of any material as long as it can form a contact hole so that wiring can be formed between the first electrode and the insulating layer, and can ensure insulation from wiring that is not connected. For example, resins such as polyimide, silicon oxide, silicon nitride, etc. can be used.

[0172] [Electrodes] A pair of electrodes can be used. The pair of electrodes is a first electrode and a second electrode. Specifically, the pair of electrodes may be an anode and a cathode. When an electric field is applied in the direction in which the organic light-emitting element emits light, the electrode with a higher potential is the anode, and the other is the cathode. It can also be said that the electrode that supplies holes to the light-emitting layer is the anode, and the electrode that supplies electrons is the cathode.

[0173] The anode material should have as large a work function as possible. Examples of such materials include simple metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten, mixtures containing these metals, alloys of these metals, and metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and zinc indium oxide. Conductive polymers such as polyaniline, polypyrrole, and polythiophene can also be used.

[0174] These electrode materials may be used alone or in combination of two or more. The anode may be composed of one layer or multiple layers.

[0175] When used as a reflective electrode, for example, chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys or laminates thereof can be used. The above materials can also function as a reflective film without functioning as an electrode. When used as a transparent electrode, transparent conductive oxide layers such as indium tin oxide (ITO) and indium zinc oxide can be used, but are not limited to these. Photolithography techniques can be used to form the electrode.

[0176] The cathode material preferably has a low work function. Examples include alkali metals such as lithium, alkaline earth metals such as calcium, and metals such as aluminum, titanium, manganese, silver, lead, and chromium, as well as mixtures containing these metals. Alternatively, alloys combining these metals can be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper, and zinc-silver can be used. Metal oxides such as indium tin oxide (ITO) can also be used. These electrode materials can be used alone or in combination. The cathode can have either a single-layer or multi-layer structure. Among these, silver is preferred, and a silver alloy is even more preferred to reduce silver aggregation. The alloy ratio is not critical as long as silver aggregation can be reduced. For example, the silver:other metal ratio can be 1:1, 3:1, or the like.

[0177] The cathode may be a top-emission element using an oxide conductive layer such as ITO, or a bottom-emission element using a reflective electrode such as aluminum (Al), and is not particularly limited. The method for forming the cathode is not particularly limited, but DC and AC sputtering methods are more preferable because they provide good film coverage and make it easier to reduce resistance.

[0178] [Organic Compound Layer] The organic compound layer may be formed as a single layer or as multiple layers. When multiple layers are present, they may be called hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, or electron injection layer depending on their functions. The organic compound layer is mainly composed of organic compounds, but may also contain inorganic atoms or inorganic compounds. For example, the organic compound layer may contain copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, or the like. The organic compound layer may be disposed between the first electrode and the second electrode, or may be disposed in contact with the first electrode and the second electrode.

[0179] The organic compound layers (hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, electron injection layer, etc.) constituting the organic light-emitting device according to this embodiment are formed by the method described below.

[0180] The organic compound layer constituting the organic light-emitting element according to this embodiment can be formed by a dry process such as vacuum deposition, ionization deposition, sputtering, plasma, etc. Alternatively, instead of the dry process, a wet process can be used in which a compound is dissolved in an appropriate solvent and a layer is formed by a known coating method (for example, spin coating, dipping, casting, LB method, inkjet method, etc.).

[0181] Here, forming a layer by a vacuum deposition method, a solution coating method, etc. makes it difficult for crystallization to occur and provides excellent stability over time. When forming a film by a coating method, it is also possible to form a film by combining with an appropriate binder resin.

[0182] Examples of the binder resin include, but are not limited to, polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, and urea resin.

[0183] These binder resins may be used singly or in combination as homopolymers or copolymers, and may further contain known additives such as plasticizers, antioxidants, and ultraviolet absorbers, if necessary.

[0184] [Protective Layer] A protective layer may be provided on the cathode. For example, by adhering glass provided with a moisture absorbent on the cathode, the intrusion of water and the like into the organic compound layer can be reduced, thereby reducing the occurrence of display defects. In another embodiment, a passivation film such as silicon nitride may be provided on the cathode to reduce the intrusion of water and the like into the organic compound layer. For example, after forming the cathode, the cathode may be transported to another chamber without breaking the vacuum, and a silicon nitride film with a thickness of 2 μm may be formed by a CVD method to serve as a protective layer. A protective layer may be provided using an atomic layer deposition (ALD) method after the film formation by the CVD method. The material of the film formed by the ALD method is not limited, and may be silicon nitride, silicon oxide, aluminum oxide, etc. Silicon nitride may be further formed on the film formed by the ALD method by a CVD method. The film formed by the ALD method may have a smaller thickness than the film formed by the CVD method. Specifically, the thickness of the film formed by the ALD method may be 50% or less, or even 10% or less, of the thickness of the film formed by the CVD method.

[0185] [Color Filter] A color filter may be provided on the protective layer. For example, a color filter taking into consideration the size of the organic light-emitting element may be provided on a separate substrate and then bonded to the substrate on which the organic light-emitting element is provided, or a color filter may be patterned on the protective layer described above using photolithography technology. The color filter may be made of a polymer.

[0186] [Planarization Layer] A planarization layer may be provided between the color filter and the protective layer. The planarization layer is provided for the purpose of reducing the unevenness of the underlying layer. It may also be called a material resin layer without limiting its purpose. The planarization layer may be composed of an organic compound, and may be either a low molecular weight or a high molecular weight, but is preferably a high molecular weight.

[0187] The planarizing layer may be provided above or below the color filter, and may be made of the same or different materials, such as polyvinyl carbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, and urea resin.

[0188] [Microlens] The organic light-emitting element according to this embodiment may have an optical component such as a microlens on the light-emitting side. The microlens may be made of acrylic resin, epoxy resin, or the like. The microlens may be used to increase the amount of light extracted from the organic light-emitting element and to control the direction of the extracted light. The microlens may have a hemispherical shape. When the microlens has a hemispherical shape, among the tangents to the hemisphere, there is a tangent that is parallel to the insulating layer, and the point of contact between this tangent and the hemisphere is the vertex of the microlens. The vertex of the microlens can be determined in the same way in any cross-sectional view. In other words, among the tangents to the semicircle of the microlens in the cross-sectional view, there is a tangent that is parallel to the insulating layer, and the point of contact between this tangent and the semicircle is the vertex of the microlens.

[0189] It is also possible to define the midpoint of the microlens. In the cross section of the microlens, a line segment is imaginary, from the point where one arc shape starts to the point where another arc shape starts, and the midpoint of this line segment can be called the midpoint of the microlens. The cross section for determining the vertex and midpoint may be a cross section perpendicular to the insulating layer.

[0190] [Counter Substrate] An counter substrate may be provided on the planarization layer. The counter substrate is called a counter substrate because it is provided at a position corresponding to the aforementioned substrate. The constituent material of the counter substrate may be the same as that of the aforementioned substrate. When the aforementioned substrate is defined as a first substrate, the counter substrate may be a second substrate.

[0191] [Pixel Circuit] The light-emitting device may have a pixel circuit connected to the light-emitting element. The pixel circuit may be an active matrix type that controls the emission of the first light-emitting element and the second light-emitting element independently. The active matrix type circuit may be voltage-programmed or current-programmed. The drive circuit has a pixel circuit for each pixel. The pixel circuit may have a light-emitting element, a transistor that controls the emission brightness of the light-emitting element, a transistor that controls the emission timing, a capacitor that holds the gate voltage of the transistor that controls the emission brightness, and a transistor for connecting to GND without going through the light-emitting element.

[0192] The light-emitting device has a display region and a peripheral region arranged around the display region. The display region has pixel circuits, and the peripheral region has a display control circuit. The mobility of a transistor constituting the pixel circuit may be lower than the mobility of a transistor constituting the display control circuit.

[0193] The slope of the current-voltage characteristics of the transistors that make up the pixel circuit may be smaller than the slope of the current-voltage characteristics of the transistors that make up the display control circuit. The slope of the current-voltage characteristics can be measured by the so-called Vg-Ig characteristics.

[0194] The transistors that make up the pixel circuit are transistors connected to light-emitting elements such as the first light-emitting element.

[0195] [Pixels] The organic light emitting device has a plurality of pixels. Each pixel has sub-pixels that emit different colors. The sub-pixels may emit, for example, RGB colors.

[0196] The pixel emits light from an area called the pixel aperture. This area is the same as the first area. The pixel aperture may be 15 μm or less, or 5 μm or more. More specifically, it may be 11 μm, 9.5 μm, 7.4 μm, 6.4 μm, etc.

[0197] The distance between the subpixels may be 10 μm or less, and specifically may be 8 μm, 7.4 μm, or 6.4 μm.

[0198] The pixels may be arranged in a known manner in a plan view. For example, they may be in a stripe arrangement, a delta arrangement, a pentile arrangement, or a Bayer arrangement. The shape of the subpixels in a plan view may be any known shape. For example, they may be rectangular, quadrilaterals such as diamonds, or hexagons. Of course, a shape that is close to a rectangle, rather than an exact shape, is included in the rectangle. The shape of the subpixels and the pixel arrangement may be used in combination.

[0199] (7) Uses of the organic light-emitting device according to this embodiment The organic light-emitting device according to this embodiment can be used as a component of a display device, an image display device, or a lighting device. Other uses include an exposure light source for an electrophotographic image forming device, a backlight for a liquid crystal display device, and a light-emitting device having a white light source and a color filter.

[0200] The display device may be an image information processing device having an image input unit that inputs image information from an area CCD, a linear CCD, a memory card, etc., an information processing unit that processes the input information, and displays the input image on the display unit.

[0201] The display unit of the imaging device or inkjet printer may have a touch panel function. The driving method of this touch panel function may be an infrared method, a capacitance method, a resistive film method, or an electromagnetic induction method, and is not particularly limited. The display device may also be used in the display unit of a multifunction printer.

[0202] Next, the display device according to this embodiment will be described with reference to the drawings.

[0203] 1A and 1B are cross-sectional views showing an example of a display device having an organic light-emitting element and a transistor connected to the organic light-emitting element. The transistor is an example of an active element. The transistor may be a thin film transistor (TFT).

[0204] 1A shows an example of a pixel, which is a component of the display device according to this embodiment. The pixel includes sub-pixels 10. The sub-pixels are divided into 10R, 10G, and 10B based on their light emission. The emitted colors may be distinguished by the wavelength of light emitted from the light-emitting layer, or the light emitted from the sub-pixels may be selectively transmitted or color-converted using a color filter or the like. Each sub-pixel includes a reflective electrode 2, which serves as a first electrode, on an interlayer insulating layer 1; an insulating layer 3 covering the edge of the reflective electrode 2; an organic compound layer 4 covering the first electrode and the insulating layer; a transparent electrode 5; a protective layer 6; and a color filter 7.

[0205] A transistor and a capacitor element may be disposed below or inside the interlayer insulating layer 1. The transistor and the first electrode may be electrically connected via a contact hole or the like (not shown).

[0206] The insulating layer 3 is also called a bank or a pixel separation film. It covers the edges of the first electrodes and surrounds the first electrodes. The portions where the insulating layer is not provided are in contact with the organic compound layer 4 and become light-emitting regions.

[0207] 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 .

[0208] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0209] The protective layer 6 reduces the penetration of moisture into the organic compound layer. Although the protective layer is illustrated as a single layer, it may be a multi-layer structure. Each layer may include an inorganic compound layer and an organic compound layer.

[0210] The color filters 7 are divided into 7R, 7G, and 7B depending on their colors. The color filters may be formed on a planarization film (not shown). A resin protective layer (not shown) may be provided on the color filters. The color filters may be formed on a protective layer 6. Alternatively, the color filters may be provided on an opposing substrate such as a glass substrate and then bonded thereto.

[0211] The display device 100 in FIG. 1B includes an organic light-emitting element 26 and a TFT 18 as an example of a transistor. A substrate 11 made of glass, silicon, or the like is provided with an insulating layer 12 on top of it. An active element 18 such as a TFT is disposed on the insulating layer, along with a gate electrode 13, a gate insulating film 14, and a semiconductor layer 15 of the active element. The active element 18 also includes the semiconductor layer 15, a drain electrode 16, and a source electrode 17. An insulating film 19 is disposed on top of the active element 18. An anode 21 constituting the organic light-emitting element 26 and the source electrode 17 are connected via a contact hole 20 provided in the insulating film.

[0212] Note that the method of electrical connection between the electrodes (anode, cathode) included in the organic light-emitting element 26 and the electrodes (source electrode, drain electrode) included in the TFT is not limited to the mode shown in FIG. 1B. That is, it is sufficient that either one of the anode or the cathode is electrically connected to either one of the TFT source electrode or the drain electrode. The TFT refers to a thin film transistor.

[0213] In the display device 100 of FIG. 1B, the organic compound layer is illustrated as if it were a single layer, but the organic compound layer 22 may be a plurality of layers. On the cathode 23, a first protective layer 24 and a second protective layer 25 for reducing the deterioration of the organic light-emitting element are provided.

[0214] In the display device 100 of FIG. 1B, a transistor is used as the switching element, but other switching elements may be used instead.

[0215] Further, the transistor used in the display device 100 of FIG. 1B is not limited to a transistor using a single crystal silicon wafer, and may also be a thin film transistor having an active layer on an insulating surface of a substrate. Examples of the active layer 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. Note that the thin film transistor is also called a TFT element.

[0216] The transistor included in the display device 100 of FIG. 1B may be formed in a substrate such as a Si substrate. Here, forming in the substrate means manufacturing a transistor by processing the substrate itself such as a Si substrate. That is, having a transistor in the substrate can also be regarded as the substrate and the transistor being integrally formed.

[0217] The organic light-emitting element according to this embodiment has its emission brightness controlled by a TFT, which is an example of a switching element. By providing multiple organic light-emitting elements on a surface, an image can be displayed based on the emission brightness of each element. The switching element according to this embodiment is not limited to a TFT, but may also be a transistor formed from low-temperature polysilicon or an active matrix driver formed on a substrate such as a Si substrate. "On the substrate" can also be referred to as "inside the substrate." Whether to provide a transistor within the substrate or to use a TFT is determined by the size of the display unit. For example, for a display unit of about 0.5 inches, it is preferable to provide the organic light-emitting element on a Si substrate.

[0218] 2 is a schematic diagram illustrating an example of a display device according to this embodiment. The display device 1000 may include a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008 between an upper cover 1001 and a lower cover 1009. The display panel 1005 may include an organic light-emitting element according to this embodiment. Flexible printed circuits FPCs 1002 and 1004 are connected to the touch panel 1003 and the display panel 1005, respectively. Transistors are printed on the circuit board 1007. The battery 1008 may not be provided if the display device is not a portable device, and may be provided in a different position even if the display device is a portable device.

[0219] The display device according to this embodiment may have color filters having red, green, and blue colors, which may be arranged in a delta arrangement.

[0220] The display device according to the present embodiment may be used as a display unit of a mobile terminal. In this case, the display device may have both a display function and an operation function. Examples of the mobile terminal include a mobile phone such as a smartphone, a tablet, and a head-mounted display.

[0221] The display device according to this embodiment may be used as a display unit of an imaging device having an imaging element that receives light. The imaging device may have a display unit that displays information acquired by the imaging element. The display unit may be a display unit exposed to the outside of the imaging device or a display unit disposed within a viewfinder. The imaging device may be a digital camera or a digital video camera.

[0222] 3A is a schematic diagram illustrating an example of an imaging device according to this embodiment. The imaging device 1100 may include a viewfinder 1101, a rear display 1102, an operation unit 1103, and a housing 1104. The viewfinder 1101 and the rear display 1102 may include the organic light-emitting element according to this embodiment. In this case, the viewfinder 1101 and the rear display 1102 may display not only the image to be captured, but also environmental information, imaging instructions, and the like. The environmental information may include the intensity of external light, the direction of external light, the speed at which the subject is moving, the possibility that the subject will be blocked by an obstruction, and the like.

[0223] Since the optimum timing for capturing an image is very short, it is better to display information as soon as possible. Therefore, it is preferable to use a display device using the organic light-emitting element according to this embodiment, because the organic light-emitting element has a fast response speed.

[0224] The imaging device 1100 may further include an optical unit (not shown). The optical unit may include a single lens or multiple lenses, which form an image on an imaging element housed in a housing 1104. The focus of the multiple lenses can be adjusted by adjusting their relative positions. This operation can also be performed automatically. The imaging device may also be called a photoelectric conversion device. Instead of sequentially capturing images, the photoelectric conversion device may include an imaging method that detects the difference from the previous image, or a method of cutting out an image from a constantly recorded image.

[0225] FIG. 3B is a schematic diagram illustrating an example of an electronic device according to this embodiment. The electronic device 1200 has a display unit 1201, an operation unit 1202, and a housing 1203. The housing 1203 may have a circuit, a printed circuit board having the circuit, a battery, and a communication unit. The operation unit 1202 may be a button or a touch panel type reaction unit. The operation unit may be a biometric recognition unit that recognizes a fingerprint to unlock the device, etc. An electronic device having a communication unit can also be called a communication device. The electronic device may further have a camera function by including a lens and an image sensor. An image captured by the camera function is displayed on the display unit. Examples of the electronic device include a smartphone, a laptop computer, etc.

[0226] 4A and 4B are schematic diagrams illustrating an example of a display device according to this embodiment. Fig. 4A illustrates a display device such as a television monitor or a PC monitor. The display device 1300 includes a housing 1301 and a display unit 1302. The display unit 1302 may include the organic light-emitting element according to this embodiment.

[0227] The display device 1300 may include a housing 1301 and a base 1303 that supports a display portion 1302. The base 1303 is not limited to the form shown in Fig. 4A. The bottom side of the housing 1301 may also serve as the base.

[0228] The housing 1301 and the display unit 1302 may be curved. The radius of curvature may be 5000 mm or more and 6000 mm or less.

[0229] FIG. 4B is a schematic diagram illustrating another example of a display device according to the present embodiment. The display device 1310 in FIG. 4B is configured to be bendable, and is a so-called foldable display device. The display device 1310 has a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may include an organic light-emitting element according to the present embodiment. The first display unit 1311 and the second display unit 1312 may be a single, seamless display device. The first display unit 1311 and the second display unit 1312 can be separated by the bending point. The first display unit 1311 and the second display unit 1312 may each display different images, or the first and second display units may display a single image.

[0230] FIG. 5A is a schematic diagram illustrating an example of a lighting device according to this embodiment. The lighting device 1400 may include a housing 1401, a light source 1402, and a circuit board 1403. The light source 1402 may include an organic light-emitting element according to this embodiment. The lighting device 1400 may include an optical film 1404 to improve the color rendering properties of the light source. The lighting device 1400 may also include a light diffusion unit 1405 to effectively diffuse light from the light source. By including the light diffusion unit 1405, the lighting device 1400 can deliver light over a wide range. The optical film 1404 and the light diffusion unit 1405 may be provided on the light emission side of the lighting device. If necessary, a cover may be provided on the outermost surface.

[0231] The lighting device is, for example, a device that illuminates a room. The lighting device may emit white, daylight white, or any other color from blue to red. The lighting device according to this embodiment may have a dimming circuit that dims these colors. The lighting device according to this embodiment may also have a power supply circuit that is connected to the organic light-emitting element according to this embodiment. The power supply circuit may be a circuit that converts AC voltage to DC voltage. Furthermore, white has a color temperature of 4200K, and daylight white has a color temperature of 5000K. The lighting device according to this embodiment may further have a color filter.

[0232] The lighting device according to this embodiment may also include a heat dissipation section, which dissipates heat from within the device to the outside and is made of a material such as metal or ceramic with high thermal conductivity.

[0233] 5B is a schematic diagram of an automobile, which is an example of a moving body according to this embodiment. The automobile has tail lamps, which are an example of a lighting device. The automobile 1500 has tail lamps 1501 and a body 1503, and may be configured so that the tail lamps are turned on when braking or the like is performed. The body 1503 may also be referred to as a fuselage. The automobile 1500 may have windows 1502 attached to the body 1503.

[0234] The tail lamp 1501 may include the organic light-emitting element according to this embodiment. The tail lamp may include a protective member for protecting the light source. The protective member may be made of any material as long as it has a certain degree of strength and is transparent, but is preferably made of polycarbonate or the like. Polycarbonate may be mixed with a furandicarboxylic acid derivative, an acrylonitrile derivative, or the like.

[0235] The window 1502 may be a transparent display other than a window for checking the front and rear of the vehicle. The transparent display may include the organic light-emitting element according to this embodiment. In this case, the constituent materials of the electrodes and the like of the organic light-emitting element according to the present invention are made of transparent materials.

[0236] 5C , the automobile 1500 includes a steering wheel 1504 for controlling the direction of travel of the vehicle, and a display unit 1505 for displaying a map, the position of the vehicle, turning directions, etc., and mounted on the vehicle body 1503. The display unit 1505 may include the organic light-emitting element according to this embodiment.

[0237] The moving body according to this embodiment includes one or both of a driving force generating unit that generates driving force mainly used to move the moving body, and a rotating body mainly used to move the moving body. The driving force generating unit may be an engine, a motor, etc. The rotating body may be a tire, a wheel, a ship's screw, a propeller of an aircraft, etc. Specifically, the moving body may be a bicycle, an automobile, a train, a ship, an aircraft, a drone, etc. The moving body may have a body and a lighting device provided on the body, or a display device provided on the body. The lighting device may emit light to indicate the position of the body.

[0238] 6A and 6B , application examples of the display devices of the above-described embodiments will be described. The display device can be applied to systems that can be worn as wearable devices, such as smart glasses, head-mounted displays, and smart contact lenses. A display device that can be used in a wearable device may include an imaging device that can photoelectrically convert visible light and a display device that can emit visible light.

[0239] 6A and 6B are schematic diagrams showing an example of glasses (smart glasses) according to this embodiment. Glasses 1600 (smart glasses) will be described using FIG. 6A . The glasses 1600 have a display unit on the rear side of lenses 1601. The display unit may have an organic light-emitting element according to the present invention. Furthermore, an imaging device 1602 such as a CMOS sensor or a SPAD may be provided on the front side of the lenses 1601.

[0240] The glasses 1600 further include a control device 1603. The control device 1603 functions as a power source that supplies power to the image capture device 1602 and the display unit. The control device 1603 also controls the operations of the image capture device 1602 and the display unit. The lens 1601 is formed with an optical system for condensing light from the image capture device 1602 and the display unit.

[0241] Using FIG. 6B , glasses 1610 (smart glasses) are described. The glasses 1610 include a control device 1612, which is provided with a display device having an organic light-emitting element according to the present invention. The control device 1612 may further include an imaging device corresponding to the imaging device 1602. A lens 1611 is formed with an optical system for projecting light emitted from the control device 1612, and an image is projected onto the lens 1611. The control device 1612 functions as a power source that supplies power to the imaging device and the display device, and controls the operation of the imaging device and the display device. The control device may include a gaze detection unit that detects the wearer's gaze. Infrared light may be used for gaze detection. The infrared light emitting unit emits infrared light toward the eyeball of a user gazing at a displayed image. An imaging unit having a light receiving element detects the emitted infrared light reflected from the eyeball, thereby obtaining an image of the eyeball. By including a reduction unit that reduces light from the infrared light emitting unit to the display unit in a planar view, degradation of image quality is reduced.

[0242] The control device 1612 detects the user's line of sight with respect to the displayed image from the captured image of the eyeball obtained by capturing infrared light. Any known method can be applied to gaze detection using the captured image of the eyeball. As an example, a gaze detection method can be used based on a Purkinje image formed by reflection of irradiated light on the cornea.

[0243] More specifically, gaze detection processing is performed based on the pupil-corneal reflex method, which uses the pupil-corneal reflex method to generate a gaze vector representing the orientation (rotation angle) of the eyeball based on the pupil image and Purkinje image contained in the captured image of the eyeball, thereby detecting the user's gaze.

[0244] The display device according to this embodiment may have an imaging device having a light receiving element, and may control the image displayed on the display device based on information about the user's line of sight from the imaging device.

[0245] Specifically, the display device determines a first field of view area where the user gazes and a second field of view area other than the first field of view area based on the line-of-sight information. The first field of view area and the second field of view area may be determined by a control device of the display device, or may be determined by an external control device and received. In the display area of ​​the display device, the display resolution of the first field of view area may be controlled to be higher than the display resolution of the second field of view area. In other words, the resolution of the second field of view area may be lower than that of the first field of view area.

[0246] The display area has a first field of view area and a second field of view area different from the first field of view area, and a high-priority area is determined from the first field of view area and the second field of view area based on line-of-sight information. The first field of view area and the second field of view area may be determined by a control device of the display device, or may be determined by an external control device and received. The resolution of the high-priority area may be controlled to be higher than the resolution of areas other than the high-priority area. In other words, the resolution of an area with a relatively low priority may be lowered.

[0247] AI may be used to determine the first field of view or a field of view with a high priority. The AI ​​may be a model configured to estimate the angle of gaze and the distance to an object in the line of sight from an image of the eyeball, using as training data an image of the eyeball and the direction in which the eyeball in the image was actually looking. The AI ​​may be included in the display device, the imaging device, or an external device. When the external device includes AI, it can be preferably applied to smart glasses that further include an imaging device that captures images of the outside. The smart glasses can display captured external information in real time.

[0248] 7A and 7B are schematic diagrams of an HMD (head-mounted display) 2301 as a display device according to one embodiment of the present invention. FIG. 7A 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 denotes the observer's right eye, and reference numeral 2303 denotes 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 at the exit pupil ER1 of the right-eye eyepiece optical system OR1, and the observer's left eye 2303 is positioned at the exit pupil EL1 of the left-eye eyepiece optical system OL1. The exit pupil ER1 is located a distance E1 away from the right-eye eyepiece optical system OR1. Similarly, the exit pupil EL1 is located at a distance E1 from the eyepiece optical system OL1 for the left eye. Optical films 2314 for lens protection, light collection, etc. are provided on the surfaces of the eyepiece optical system OR1 for the right eye (the surface facing the right eye 2302) and the eyepiece optical system OL1 for the left eye (the surface facing the left eye 2303).

[0249] Reference numerals 2308 and 2309 denote display devices for the right eye and the left eye, respectively. These display devices may be the display devices according to embodiment 1. FIG. 7B is a schematic diagram showing an example in which a display device according to an embodiment of the present invention is connected to an external device, showing the appearance of an HMD 2301 and a personal computer 2350 connected thereto. Each display device displays a display image (original image) corresponding to an image signal output from the personal computer 2350. In this embodiment, the display devices are connected by wire, but may also be connected wirelessly. Furthermore, the HMD 2301 may be a device that has an image processing device built in and operates as a standalone device.

[0250] The eyepiece optical systems OR1 and OL1 guide light from the display devices 2308 and 2309 to the exit pupils ER1 and EL1, respectively, to project enlarged virtual images of the displayed images onto the observer's right eye 2302 and left eye 2303. This allows the observer to observe the display images (virtual images of the images) displayed on the display devices 2308 and 2309 through the eyepiece optical systems OR1 and OL1.

[0251] Although not shown, the HMD 2301 may have a control device. The control device functions as a power source that supplies power to the display devices 2308 and 2309, and also controls the operations of the display devices 2308 and 2309.

[0252] 8A is a schematic diagram showing an example of an image forming apparatus according to the present embodiment. The image forming apparatus 40 is an electrophotographic image forming apparatus and includes a photoconductor 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transfer unit 32, a transport roller 33, and a fixing unit 35. Light 29 is irradiated from the exposure light source 28, and an electrostatic latent image is formed on the surface of the photoconductor 27. The exposure light source 28 may include an organic light-emitting element according to the present embodiment. The developing unit 31 includes toner and the like. The charging unit 30 charges the photoconductor 27. The transfer unit 32 transfers the developed image to a storage medium 34. The transport roller 33 transports the recording medium 34. The recording medium 34 is, for example, paper. The fixing unit 35 fixes the image formed on the recording medium 34.

[0253] 8B and 8C are diagrams showing an exposure light source 28 and are schematic diagrams illustrating a state in which multiple light-emitting units 36 are arranged on a long substrate. Arrow 37 indicates the column direction in which the organic light-emitting elements are arranged. This column direction is the same as the axis direction about which the photoconductor 27 rotates. This direction can also be referred to as the long axis direction of the photoconductor 27. FIG. 8B shows a configuration in which the light-emitting units 36 are arranged along the long axis of the photoconductor 27. FIG. 8C shows a different configuration from FIG. 8B, in which the light-emitting units 36 are arranged alternately in the column direction in the first and second columns. The first and second columns are arranged at different positions in the row direction. In the first column, multiple light-emitting units 36 are arranged at intervals. In the second column, the light-emitting units 36 are located at positions corresponding to the intervals between the light-emitting units 36 in the first column. In other words, multiple light-emitting units 36 are also arranged at intervals in the row direction. The arrangement in FIG. 8C can also be described as a grid-like arrangement, a houndstooth arrangement, or a checkerboard pattern.

[0254] As described above, by using a device using the organic light-emitting element according to this embodiment, it is possible to provide a stable display with good image quality even over a long period of time.

[0255] The present invention will be described in detail below using examples, but the present invention is not limited to these examples.

[0256] Example 1 Synthesis of Compound A-1 Compound A-1 was synthesized according to the following procedure.

[0257] <Synthesis of Intermediate A-1-3>

[0258]

[0259] 0.73 g (2.0 mmol, 1.0 eq) of intermediate A-1-1, 0.55 g (1.1 eq) of intermediate A-1-2, 0.62 g (3.0 eq) of sodium carbonate, and 0.06 g (0.03 eq) of tetrakis(triphenylphosphine)palladium(0) were weighed into a 100 mL three-necked round-bottom flask, and vacuum degassing / Ar substitution was performed five times. After thorough vacuum degassing and nitrogen substitution, 20 mL of toluene, 5.0 mL of ethanol, and 3.0 mL of water were added under a nitrogen atmosphere, and the mixture was refluxed and stirred at 74°C for 8 hours. After that, heating was stopped and the reaction solution was returned to room temperature. Extraction was performed three times with toluene, and anhydrous sodium sulfate was added and the mixture was left to stand for a while. The sodium sulfate was removed by filtration, and the solution was concentrated under reduced pressure. The resulting reaction solution was passed through silica gel short column chromatography (eluent: toluene), and the fraction containing the target product was collected and concentrated under reduced pressure. The resulting reaction solution was then passed through silica gel column chromatography (eluent: heptane-toluene), and the fraction containing the intermediate was collected and concentrated under reduced pressure. The resulting solid (0.68 g, yield 70%) was the target intermediate A-1-3, and mass spectrometry analysis showed that the molecular weight was 489.6590 and the m / z was 489.2668.

[0260] <Synthesis of Intermediate A-1-4>

[0261]

[0262] Intermediate A-1-3 (0.68 g, 1.4 mmol) was dissolved in dichloromethane (140 mL) and 1 M BBr ３A dichloromethane solution (4 mL, 4.0 mmol) of the above was added and refluxed for 8 hours. After completion of the reaction, ice water (50 mL) was added and the precipitate was filtered off. This solid was washed with methanol to obtain a white solid (0.57 g, yield 86%). The obtained solid was the target intermediate A-1-4, and mass spectrometry analysis showed that the molecular weight was 475.6320 and the m / z was 475.2511.

[0263] <Synthesis of Intermediate A-1-5>

[0264]

[0265] Intermediate A-1-4 (0.57 g, 1.2 mmol) was suspended in dichloromethane (60 mL) and pyridine (60 mL), and anhydrous triflate (0.29 mL, 1.8 mmol) was added and stirred at room temperature for 8 hours. After the reaction was completed, water (50 mL) was added and the precipitate was filtered off. This solid was washed with methanol and ethyl acetate to obtain a white solid (0.61 g, yield 83%). The obtained solid was the target intermediate A-1-5, and mass spectrometry analysis showed that the molecular weight was 607.6882 and the m / z was 607.2004.

[0266] <Synthesis of Intermediate A-1-7>

[0267]

[0268] 0.61 g (1.0 mmol, 2.0 eq) of intermediate A-1-5, 0.16 g (1.0 eq) of intermediate A-1-6, 0.16 g (3.0 eq) of sodium carbonate, and 0.04 g (0.03 eq) of tetrakis(triphenylphosphine)palladium(0) were weighed into a 100 mL three-necked round-bottom flask, and vacuum degassing / Ar substitution was performed five times. After thorough vacuum degassing and nitrogen substitution, 10 mL of toluene, 2.5 mL of ethanol, and 1.5 mL of water were added under a nitrogen atmosphere, and the mixture was refluxed and stirred at 80°C for 8 hours. Heating was then stopped, and the reaction solution was allowed to return to room temperature. Extraction was performed three times with toluene, followed by addition of anhydrous sodium sulfate, and the mixture was allowed to stand for a while. The sodium sulfate was removed by filtration, and the solution was concentrated under reduced pressure. The resulting reaction solution was passed through silica gel short column chromatography (eluent: toluene), and the fraction containing the target product was collected and concentrated under reduced pressure. The resulting reaction solution was then passed through silica gel column chromatography (eluent: heptane-toluene), and the fraction containing the intermediate was collected and concentrated under reduced pressure. The resulting solid (0.40 g, yield 70%) was the target intermediate A-1-7, and mass spectrometry analysis showed that the molecular weight was 1151.1400 and the m / z was 1150.3471.

[0269] <Synthesis of Compound A-1>

[0270]

[0271] Under an argon atmosphere, intermediate A-1-8 (0.68 g, 0.35 mmol), 6.6 mg (0.1 eq.) of copper iodide, 8.0 mg (0.2 eq.) of L-proline, and 140 mg (3.0 eq.) of potassium carbonate were suspended in DMSO (10 mL) and heated with stirring at 150°C for 6 hours. After completion of the reaction, the mixture was filtered through Celite, and the solvent was distilled off to obtain a solid, which was purified by column chromatography to obtain a yellow solid (70 mg, yield 26%). The obtained solid was the target compound A-1, and as a result of mass spectrometry analysis, the molecular weight was 989.3160 ​​and the m / z was 988.4968.

[0272] Example 2 Synthesis of Compound A-2 Synthesis of Intermediate A-2-1

[0273]

[0274] 0.88 g (2.0 mmol, 1.0 eq) of intermediate A-2-1, 0.55 g (1.1 eq.) of intermediate A-2-2, 0.62 g (3.0 eq.) of sodium carbonate, and 0.06 g (0.03 eq.) of tetrakis(triphenylphosphine)palladium(0) were weighed into a 100 mL three-necked round-bottom flask, and vacuum degassing / Ar substitution was performed five times. After thorough vacuum degassing and nitrogen substitution, 20 mL of toluene, 5.0 mL of ethanol, and 3.0 mL of water were added under a nitrogen atmosphere, and the mixture was refluxed and stirred at 74°C for 8 hours. After that, heating was stopped and the reaction solution was returned to room temperature. Extraction was performed three times with toluene, and anhydrous sodium sulfate was added and the mixture was left to stand for a while. The sodium sulfate was removed by filtration, and the solution was concentrated under reduced pressure. The resulting reaction solution was passed through silica gel short column chromatography (eluent: toluene), and the fraction containing the target product was collected and concentrated under reduced pressure. The resulting oil was then subjected to silica gel column chromatography (eluent: heptane-toluene), and the fraction containing the intermediate was collected and concentrated under reduced pressure. The resulting solid (0.74 g, yield 65%) was the target intermediate A-2-3, and mass spectrometry analysis showed that the molecular weight was 565.7570 and the m / z was 565.2981.

[0275] <Synthesis of Intermediate A-2-4>

[0276]

[0277] Intermediate A-2-3 (0.74 g, 1.3 mmol) was dissolved in dichloromethane (130 mL) and 1 M BBr ３ A dichloromethane solution (3.7 mL, 3.7 mmol) of the above was added and refluxed for 8 hours. After completion of the reaction, ice water (50 mL) was added and the precipitate was filtered off. This solid was washed with methanol to obtain a white solid (0.57 g, yield 80%). The obtained solid was the target intermediate A-2-4, and mass spectrometry analysis showed that the molecular weight was 551.7300 and the m / z was 551.2824.

[0278] <Synthesis of Intermediate A-2-5>

[0279]

[0280] Intermediate A-2-4 (0.57 g, 1.0 mmol) was suspended in dichloromethane (60 mL) and pyridine (60 mL), and anhydrous triflate (0.24 mL, 1.5 mmol) was added and stirred at room temperature for 8 hours. After the reaction was completed, water (50 mL) was added and the precipitate was filtered off. This solid was washed with methanol and ethyl acetate to obtain a white solid (0.55 g, yield 79%). The obtained solid was the target intermediate A-2-5, and mass spectrometry analysis showed that the molecular weight was 683.7862 and the m / z was 683.2317.

[0281] <Synthesis of Intermediate A-2-7>

[0282]

[0283] 0.55 g (0.79 mmol, 2.0 eq.) of intermediate A-2-5, 0.12 g (1.0 eq.) of intermediate A-2-6, 0.13 g (3.0 eq.) of sodium carbonate, and 0.03 g (0.03 eq.) of tetrakis(triphenylphosphine)palladium(0) were weighed into a 100 mL three-necked round-bottom flask, and vacuum degassing / Ar substitution was performed five times. After thorough vacuum degassing and nitrogen substitution, 10 mL of toluene, 2.5 mL of ethanol, and 1.5 mL of water were added under a nitrogen atmosphere, and the mixture was refluxed and stirred at 80°C for 8 hours. After that, heating was stopped and the reaction solution was returned to room temperature. After extraction with toluene three times, the organic solvent layers were combined, anhydrous sodium sulfate was added, and the mixture was allowed to stand for a while. The sodium sulfate was removed by filtration, and the solution was concentrated under reduced pressure. The resulting reaction solution was passed through a silica gel short column chromatography (eluent: toluene), and the fraction containing the target product was collected and concentrated under reduced pressure. The resulting reaction solution was subjected to silica gel column chromatography (eluent: heptane-toluene), and the fraction containing the intermediate was collected and concentrated under reduced pressure. The resulting solid (0.31 g, yield 62%) was the target intermediate A-1-7, and mass spectrometry analysis showed that the molecular weight was 683.2317 and the m / z was 1302.4097.

[0284] <Synthesis of Compound A-2>

[0285]

[0286] Under an argon atmosphere, intermediate A-2-8 (0.31 g, 0.49 mmol), 9.0 mg (0.1 eq.) of copper iodide, 11.3 mg (0.2 eq.) of L-proline, and 180 mg (3.0 eq.) of potassium carbonate were suspended in DMSO (10 mL) and heated with stirring at 150°C for 6 hours. After completion of the reaction, the mixture was filtered through Celite, and the solvent was distilled off to obtain a solid, which was purified by column chromatography to obtain a yellow solid (110 mg, yield 20%). The obtained solid was the target compound A-2, and as a result of mass spectrometry analysis, it was found that the molecular weight was 1141.5120 and the m / z was 1140.5594.

[0287] [Example 3 (Preparation of Ink Composition)] The components shown in Table 2 were mixed in such proportions that the host material was 4.75 mass %, the guest material was 0.25 mass %, and the organic solvent was 95.0 mass % relative to the total mass of the composition. The mixture was then stirred at 60° C. for 5 hours and then at 25° C. for a further 12 hours. The mixture was then filtered through a filter with a pore size of 0.2 μm to prepare an ink composition.

[0288]

[0289] Example 4 (Fabrication and Evaluation of Organic Light-Emitting Device) Fabrication of Organic Light-Emitting Device An organic light-emitting device was fabricated by sequentially forming an anode, a hole injection layer, a light-emitting layer, an electron transport layer, and a cathode on a substrate according to the following procedure.

[0290] The transparent conductive support substrate (ITO substrate) used was a glass substrate on which an ITO film was formed as an anode by sputtering to a thickness of 100 nm. The ITO substrate was washed with pure water and then with isopropanol, and subjected to UV-ozone treatment. A hole injection layer was then formed by spin coating. The film formation conditions were as follows: Coating liquid: Poly(3,4-ethylenedioxythiophene)polystyrenesulfonic acid aqueous solution (PEDOT;PSS aqueous solution, manufactured by Aldrich, conductivity 1×10 －５ S / cm, compound concentration 2.8% by mass) Spin coating conditions: 3,000 rpm, 60 seconds Annealing conditions: 200°C, 1 hour Film thickness: 40 nm

[0291] Next, a light-emitting layer was formed by spin coating under the following conditions: Coating liquid: Ink composition No. 1 Spin coating conditions: 2,000 rpm, 60 seconds Annealing conditions: 110° C., 10 minutes Film thickness: 45 nm

[0292] Finally, an electron transport layer and a cathode were formed by vacuum deposition using resistance heating. ２ The film formation conditions were as follows: Degree of vacuum: 1×10 －５ Pa Electron transport layer: TPBi (50 nm) Cathode: LiF (0.5 nm), Al (90 nm)

[0293] Thereafter, in order to prevent deterioration of the element due to absorption of moisture, the element was covered with a protective glass plate in a dry air atmosphere and sealed with an acrylic resin adhesive.

[0294] <Evaluation of Organic Light-Emitting Element> The organic light-emitting element thus fabricated was subjected to a luminance test at 300 cd / m using an ITO electrode as the anode and an Al electrode as the cathode. ２ The external quantum efficiency was measured at each time point, and a relative value to that of Example 4 was calculated and evaluated according to the following criteria: AA: The ratio was 1.2 or more; A: The ratio was 1.0 or more and less than 1.2; B: The ratio was 0.7 or more and less than 1.0; C: The ratio was less than 0.7.

[0295] [Examples 5 to 7, Comparative Examples 1 to 3 (Fabrication and Evaluation of Organic Light-Emitting Devices)] Organic light-emitting devices were fabricated in the same manner as in Example 4, except that the coating liquid used to form the light-emitting layer was changed to the ink composition shown in Table 3.

[0296]

[0297] The results in Table 3 show that the organic light-emitting devices of Examples 4 to 9 exhibit superior external quantum efficiency compared to the organic light-emitting devices of Comparative Examples 1 to 3. This is thought to be because the organic compound according to this embodiment has bulky substituents at specific positions, which can reduce aggregation of guest materials.

[0298] Among the examples, the organic light-emitting devices of Examples 5, 7, and 9 exhibited particularly excellent external quantum efficiency. A-2, the guest material used in Examples 5, 7, and 9, is a compound in which the compound A-1 further has a substituent at a specific position, and is a compound that exhibits a lower cohesive energy density. Therefore, it is believed that the cohesion of the guest material could be further reduced, thereby exhibiting superior external quantum efficiency.

[0299] EM43, which is the host material used in Example 9, is a compound represented by the general formula (7), １７ or R １９ One of the structures is a metaphenylene chain in which three phenyl groups are bonded, which is a particularly bulky structure. This structure can further reduce the aggregation of the host materials, and the external quantum yield of this example was particularly excellent.

[0300] As described above, the organic compound according to the present invention is an organic compound that is unlikely to aggregate, and therefore, by using the organic compound according to the present invention, an organic light-emitting device that exhibits excellent luminous efficiency can be obtained.

[0301] The present invention can also have the following configuration.

[0302] (Configuration 1) An organic compound represented by general formula (1):

[0303]

[0304] In general formula (1), R １２ ~R １８ , R ２２ ~R ２８ , R ３１ and R ３２ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group, provided that in general formulas (1) and (2), R １５ , R １６ , R２５ , R ２６ , R １１１ At least two of R are substituted or unsubstituted alkyl groups or substituted or unsubstituted aryl groups. １３ ~R １７ Two of the groups are substituted with general formula (2), and R ２３ ~R ２７ Two of R are substituted with general formula (2). １２ , R １８ , R ２２ , R ２８ At least two of the above are represented by general formula (3) or general formula (4).

[0305]

[0306] In general formula (2), R １１１ ~R １１４ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. X is an oxygen atom, a sulfur atom, or CRR', and R and R' are either a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. * indicates the bonding position with general formula (1).

[0307] In general formulas (3) and (4), R ３０１ , R ３０６ , R ４０１ , R ４０５ , R ４０６ , and R ４１０ are each independently selected from the group consisting of a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group, provided that R ４０５ and R ４１０may be directly bonded. ３０２ , R ３０４ ~R ３０５ , R ４０２ ~R ４０４ , and R ４０７ ~R ４０９ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. ３０１ ~R ３０６ Two adjacent ones of these may be bonded to form a ring. * indicates the bonding position to general formula (1).

[0308] (Configuration 2) An organic compound represented by general formula (1):

[0309]

[0310] In general formula (1), R １２ ~R １８ , R ２２ ~R ２８ , R ３１ and R ３２ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. １３ ~R １７ Two of the groups are substituted with general formula (2), and R ２３ ~R ２７ Two of R are substituted with general formula (2). １２ , R １８ , R ２２ , R ２８ At least two of the above are represented by general formula (3) or general formula (4).

[0311]

[0312] In general formula (2), R １１１ ~R １１４ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. X is an oxygen atom or CRR', and R and R' are either a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. * indicates the bonding position with general formula (1).

[0313] In general formulas (3) and (4), R ３０１ , R ３０６ , R ４０１ , R ４０５ , R ４０６ , and R ４１０ are each independently selected from the group consisting of a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group, provided that R ４０５ and R ４１０ may be directly bonded. ３０２ , R ３０４ ~R ３０５ , R ４０２ ~R ４０４ , and R ４０７ ~R ４０９ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. ３０１ ~R ３０６Two adjacent ones of these may be bonded to form a ring. * indicates the bonding position to general formula (1).

[0314] (Configuration 3) In the general formulas (1) and (2), R １５ , R １６ , R ２５ , R ２６ , R １１１ 3. The organic compound according to claim 2, wherein at least two of the above are a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

[0315] (Configuration 4) In the general formulas (3) and (4), R ３０１ , R ３０６ , R ４０１ , R ４０５ , R ４０６ , and R ４１０ are each independently selected from the group consisting of an isopropyl group, a tert-butyl group, a cyclopropyl group, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, a substituted or unsubstituted silyl group, and a cyano group.

[0316] (Configuration 5) In the general formulas (3) and (4), R ３０１ , R ３０６ , R ４０１ , R ４０５ , R ４０６ , and R ４１０ are each independently selected from the group consisting of an alkyl group having 3 or 4 carbon atoms and an aryl group having 6 to 24 carbon atoms.

[0317] (Configuration 6) In the general formulas (3) and (4), R ３０１ , R ３０６ , R ４０１ , R ４０５ , R ４０６ , and R ４１０ are each independently selected from the group consisting of an isopropyl group, a cyclopropyl group, a phenyl group, a naphthyl group, and a chain of multiple phenyl groups.

[0318] (Configuration 7) In general formula (1), R １２ and R ２２ 7. The organic compound according to any one of structures 1 to 6, wherein the organic compound has general formula (3) or (4).

[0319] (Configuration 8) In general formula (1), R １４ and R １５ , and R ２４ and R ２５ and each of the following is bonded to the general formula (2):

[0320] (Configuration 9) The organic compound according to configuration 1, wherein in general formula (2), X is an oxygen atom or a sulfur atom.

[0321] (Configuration 10) The organic compound according to any one of configurations 1 to 9, which is represented by general formula (5):

[0322]

[0323] In general formula (5), R ２１１ ~R ２１４ , R ２２１ ~R ２２４ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. X may be the same or different.

[0324] (Configuration 11) The organic compound according to any one of Configurations 1 to 10, wherein the organic compound represented by general formula (1) is the following compound:

[0325]

[0326] (Configuration 12) A composition comprising the organic compound according to any one of Configurations 1 to 11 and an organic compound represented by general formula (6).

[0327]

[0328] In general formula (6), A １ or A １０ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group.

[0329] (Configuration 13) In the general formula (6), A １ or A ２ are each independently selected from the group consisting of a substituted or unsubstituted aryl group and a substituted or unsubstituted heterocyclic group; ３ or A １０ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, an alkyl group having from 1 to 4 carbon atoms, an aryl group having from 6 to 10 carbon atoms, a heterocyclic group having from 5 to 12 carbon atoms, and a cyano group.

[0330] (Configuration 14) In the general formula (6), A １ or A ２ 14. The composition according to claim 12 or 13, wherein one of the groups is an aryl group having 6 to 24 carbon atoms, and the other is a heterocyclic group having 5 to 12 carbon atoms.

[0331] (Structure 15) An organic light-emitting element having a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, wherein at least one layer of the organic compound layer contains the organic compound according to any one of Structures 1 to 11.

[0332] (Structure 16) The organic light-emitting element according to Structure 15, wherein the organic compound layer is an emitting layer further containing a first compound, and the lowest excited singlet energy of the first compound is higher than the lowest excited singlet energy of the organic compound.

[0333] (Configuration 17) The organic light-emitting device according to Configuration 16, wherein the first compound is a compound represented by general formula (7).

[0334]

[0335] In general formula (7), R １ ~R ２０ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted acyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted imino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted sulfanyl group, a substituted or unsubstituted sulfinyl group, a substituted or unsubstituted sulfonyl group, and a cyano group. X is an oxygen atom or a sulfur atom. However, R １６ ~R ２０ One of the formulas is any one of general formulas (8) to (10).

[0336]

[0337] In the general formulas (8) to (10), R ２１ ~R ２９ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted acyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted imino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted sulfanyl group, a substituted or unsubstituted sulfinyl group, a substituted or unsubstituted sulfonyl group, and a cyano group. * indicates the bonding position with general formula (7).

[0338] (Configuration 18) A display device having a plurality of pixels, at least one of the plurality of pixels having the organic light-emitting element according to any one of Configurations 15 to 17 and a transistor connected to the organic light-emitting element.

[0339] (Configuration 19) A photoelectric conversion device comprising: an imaging element that receives light; and a display unit that displays an image captured by the imaging element, wherein the display unit has the organic light-emitting element according to any one of Configurations 15 to 17.

[0340] (Configuration 20) An image display device comprising: a display section having the organic light-emitting element according to any one of Configurations 15 to 17; and a housing in which the display section is provided.

[0341] (Configuration 21) An electronic device comprising: a display unit having the organic light-emitting element according to any one of Configurations 15 to 17; a housing in which the display unit is provided; and a communication unit provided in the housing and communicating with an external device.

[0342] (Configuration 22) A wearable device comprising: a display unit having the organic light-emitting element according to any one of Configurations 15 to 17; an optical system that focuses light from the display unit; and a control device that controls display on the display unit.

[0343] (Configuration 23) A moving body comprising: a lighting fixture having the organic light-emitting element according to any one of Configurations 15 to 17; and a vehicle on which the lighting fixture is provided.

[0344] The present invention is not limited to the above-described embodiments, and various modifications and variations can be made without departing from the spirit and scope of the present invention. Therefore, the following claims are appended to apprise the public of the scope of the present invention.

[0345] This application claims priority based on Japanese Patent Application No. 2024-145511 filed on August 27, 2024 and Japanese Patent Application No. 2025-112305 filed on July 2, 2025, the entire contents of which are incorporated herein by reference.

[0346] REFERENCE SIGNS LIST 1 Interlayer insulating layer 2 Reflective electrode 3 Insulating layer 4 Organic compound layer 5 Transparent electrode 6 Protective layer 7 Color filter 10 Subpixel 11 Substrate 12 Insulating layer 13 Gate electrode 14 Gate insulating film 15 Semiconductor layer 16 Drain electrode 17 Source electrode 18 Thin film transistor 19 Insulating film 20 Contact hole 21 Lower electrode 22 Organic compound layer 23 Upper electrode 24 First protective layer 25 Second protective layer 26 Organic light-emitting element 27 Photosensitive member 28 Exposure light source 29 Light 30 Charging section 31 Developing section 32 Transfer section 33 Transport section 34 Recording medium 35 Fixing section 36 Light-emitting section 37 First direction parallel to the major axis of the photosensitive member 40 Image forming apparatus 100 Display device 1000 Display device 1001 Upper cover 1002 Flexible printed circuit 1003 Touch panel 1004 Flexible printed circuit 1005 Display panel 1006 Frame 1007 Circuit board 1008 Battery 1009 Lower cover 1100 Imaging device 1101 Viewfinder 1102 Rear display 1103 Operation unit 1104 Housing 1200 Electronic device 1201 Display unit 1202 Operation unit 1203 Housing 1300 Display device 1301 Frame 1302 Display unit 1303 Base 1310 Display device 1311 First display unit 1312 Second display unit 1313 Housing 1314 Bend point 1400 Illumination device 1401 Housing 1402 Light source 1403 Circuit board 1404 Optical film 1405 Light diffusion unit 1500 Automobile 1501 Tail lamp 1502 Window 1503 Vehicle body 1600 Smart glasses 1601 Lens 1602 Imaging device 1603 Control device 1610 Smart glasses 1611 Lens 1612 Control device

Claims

1. An organic compound represented by general formula (1): In general formula (1), R １２ ~R １８ , R ２２ ~R ２８ , R ３１ and R ３２ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group, provided that in general formulas (1) and (2), R １５ , R １６ , R ２５ , R ２６ , R １１１ At least two of R are substituted or unsubstituted alkyl groups or substituted or unsubstituted aryl groups. １３ ~R １７ Two of the groups are substituted with general formula (2), and R ２３ ~R ２７ Two of R are substituted with general formula (2). １２ , R １８ , R ２２ , R ２８ At least two of the above are represented by general formula (3) or general formula (4). In general formula (2), R １１１ ~R １１４ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. X is an oxygen atom, a sulfur atom, or CRR', and R and R' are either a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. * indicates the bonding position with general formula (1). In general formulas (3) and (4), R ３０１ , R ３０６ , R ４０１ , R ４０５ , R ４０６ , and R ４１０ are each independently selected from the group consisting of a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group, provided that R ４０５ and R ４１０ may be directly bonded. ３０２ , R ３０４ ~R ３０５ , R ４０２ ~R ４０４ , and R ４０７ ~R ４０９ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. ３０１ ~R ３０６ Two adjacent ones of these may be bonded to form a ring. * indicates the bonding position to general formula (1).

2. In general formulas (3) and (4), R ３０１ , R ３０６ , R ４０１ , R ４０５ , R ４０６ , and R ４１０ are each independently selected from the group consisting of an isopropyl group, a tert-butyl group, a cyclopropyl group, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, a substituted or unsubstituted silyl group, and a cyano group.

3. In general formulas (3) and (4), R ３０１ , R ３０６ , R ４０１ , R ４０５ , R ４０６ , and R ４１０ and are each independently selected from the group consisting of an alkyl group having 3 or 4 carbon atoms and an aryl group having 6 to 24 carbon atoms.

4. In general formulas (3) and (4), R ３０１ , R ３０６ , R ４０１ , R ４０５ , R ４０６ , and R ４１０ are each independently selected from the group consisting of an isopropyl group, a cyclopropyl group, a phenyl group, a naphthyl group, and a chain of phenyl groups.

5. In general formula (1), R １２ and R ２２ The organic compound according to claim 1, characterized in that it has the general formula (3) or (4).

6. In general formula (1), R １４ and R １５ , and R ２４ and R ２５ and each bond to the general formula (2).

7. The organic compound according to claim 1, wherein X in general formula (2) is an oxygen atom or a sulfur atom.

8. The organic compound according to claim 1, which is represented by general formula (5). In general formula (5), R ２１１ ~R ２１４ , R ２２１ ~R ２２４ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. X may be the same or different.

9. The organic compound according to claim 1, characterized in that the organic compound represented by general formula (1) is the following compound:

10. An organic compound represented by general formula (1): In general formula (1), R １２ ~R １８ , R ２２ ~R ２８ , R ３１ and R ３２ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. １３ ~R １７ Two of the groups are substituted with general formula (2), and R ２３ ~R ２７ Two of R are substituted with general formula (2). １２ , R １８ , R ２２ , R ２８ At least two of the above are represented by general formula (3) or general formula (4). In general formula (2), R １１１ ~R １１４ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. X is an oxygen atom or CRR', and R and R' are either a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. * indicates the bonding position with general formula (1). In general formulas (3) and (4), R ３０１ , R ３０６ , R ４０１ , R ４０５ , R ４０６ , and R ４１０ are each independently selected from the group consisting of a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group, provided that R ４０５ and R ４１０ may be directly bonded. ３０２ , R ３０４ ~R ３０５ , R ４０２ ~R ４０４ , and R ４０７ ~R ４０９ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. ３０１ ~R ３０６ Two adjacent ones of these may be bonded to form a ring. * indicates the bonding position to general formula (1).

11. In general formulas (1) and (2), R １５ , R １６ , R ２５ , R ２６ , R １１１ 11. The organic compound according to claim 10, wherein at least two of the groups are a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

12. A composition comprising an organic compound according to any one of claims 1 to 11 and an organic compound represented by general formula (6). In general formula (6), A １ or A １０ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group.

13. In general formula (6), A １ or A ２ are each independently selected from the group consisting of a substituted or unsubstituted aryl group and a substituted or unsubstituted heterocyclic group; ３ or A １０ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, an alkyl group having from 1 to 4 carbon atoms, an aryl group having from 6 to 10 carbon atoms, a heterocyclic group having from 5 to 12 carbon atoms, and a cyano group.

14. In general formula (6), A １ or A ２ 14. The composition according to claim 13, wherein one of said groups is an aryl group having from 6 to 24 carbon atoms, and the other is a heterocyclic group having from 5 to 12 carbon atoms.

15. An organic light-emitting element having a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, wherein at least one layer of the organic compound layer contains the organic compound described in claim 1.

16. The organic light-emitting element according to claim 15, wherein the organic compound layer is an emitting layer further comprising a first compound, and the lowest excited singlet energy of the first compound is higher than the lowest excited singlet energy of the organic compound.

17. The organic light-emitting device according to claim 16, wherein the first compound is a compound represented by general formula (7). In general formula (7), R １ ~R ２０ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted acyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted imino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted sulfanyl group, a substituted or unsubstituted sulfinyl group, a substituted or unsubstituted sulfonyl group, and a cyano group. X is an oxygen atom or a sulfur atom. However, R １６ ~R ２０ One of the formulas is any one of general formulas (8) to (10). In the general formulas (8) to (10), R ２１ ~R ２９ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted acyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted imino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted sulfanyl group, a substituted or unsubstituted sulfinyl group, a substituted or unsubstituted sulfonyl group, and a cyano group. * indicates the bonding position with general formula (7).

18. A display device having a plurality of pixels, at least one of the plurality of pixels comprising an organic light-emitting element according to any one of claims 15 to 17 and a transistor connected to the organic light-emitting element.

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

20. An image display device comprising: a display unit having an organic light-emitting element according to any one of claims 15 to 17; and a housing in which the display unit is provided.

21. An electronic device comprising: a display unit having an organic light-emitting element according to any one of claims 15 to 17; a housing in which the display unit is provided; and a communication unit provided in the housing for communicating with the outside.

22. A wearable device comprising a display unit having the organic light-emitting element according to any one of claims 15 to 17, an optical system for focusing light from the display unit, and a control device for controlling the display of the display unit.

23. A moving object comprising a lighting fixture having the organic light-emitting element according to any one of claims 15 to 17, and a vehicle on which the lighting fixture is mounted.

Images