Organic compound, organic light-emitting element, ink composition, display device, photoelectric conversion device, image display device, electronic unit, wearable device, illumination device, moving body, and exposure light source

Abstract

An organic compound represented by formula (1) is provided as an organic compound having high oscillator strength and high light-emitting efficiency.　In formula (1), the a ring and the b ring are each independently selected from among aryl rings and the like. R1 to R3 are each independently selected from among a hydrogen atom, alkyl groups, and the like. However, one or more of R1 to R3 are independently selected from among groups represented by formula (2). R4 to R7 are each independently selected from among a hydrogen atom, alkyl groups, and the like. However, one neighboring group of two among R4 to R7 are bonded to form a c ring, and the c ring is a heteroaryl ring obtained by condensation of a five-membered ring and a six-membered ring. X1 is an oxygen atom or a sulfur atom.　In formula (2), the d rings are each independently selected from among heteroaryl rings obtained by condensation of a five-membered ring and a six-membered ring, and the like. The X2s are each independently selected from among an oxygen atom or a sulfur atom. The * represents the bonding position with formula (1).

Description

Organic compound, organic light-emitting element, ink composition, display device, photoelectric conversion device, image display device, electronic device, wearable device, lighting device, mobile object, and exposure light source

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

[0002] An organic light-emitting device (hereinafter sometimes referred to as an "organic electroluminescence device" or "organic EL device") is an electronic device 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 device emits light. To improve the color purity of organic light-emitting devices, fluorescent materials with narrow fluorescence spectrum widths have attracted attention. For example, a group of boron-containing compounds known as DABNA are known to have narrow emission spectrum widths due to their rigid structure. Patent Document 1 describes compound Ref-1 as an example of a fluorescent material into which boron atoms have been introduced.

[0003]

[0004] Chinese Patent Application Publication No. 115772185

[0005] However, the compound Ref-1 described in Patent Document 1 has a low oscillator strength, which is a factor that contributes to the luminance during emission, for a light-emitting material, and an organic compound with a higher oscillator strength and a higher PLQY has been desired.

[0006] The present disclosure has been made in view of the above-mentioned problems, and aims to provide an organic compound having high oscillator strength and high PLQY. The organic compound of the present disclosure is characterized by being represented by the following general formula (1):

[0007] In general formula (1), ring a and ring b are each independently selected from a substituted or unsubstituted aryl ring and a substituted or unsubstituted heteroaryl ring. Ring a and ring b may be bonded to each other. R1 to R3 are each independently selected from 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 heteroaryl 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. However, at least one of R1 to R3 is each independently selected from a group represented by the following general formula (2): R4 to R7 are each independently selected from 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 heteroaryl 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. However, two adjacent groups from one pair of R4 to R7 are bonded to form a c-ring, and the c-ring is a substituted or unsubstituted heteroaryl ring in which a five-membered ring and a six-membered ring are fused. X1 is an oxygen atom or a sulfur atom.

[0008] In general formula (2), ring d is independently selected from a substituted or unsubstituted aryl ring and a substituted or unsubstituted heteroaryl ring formed by condensing a five-membered ring and a six-membered ring. X2 is independently selected from an oxygen atom and a sulfur atom. * indicates the bonding position with general formula (1). Substituents that ring a to ring d may have are independently selected from a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl 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.

[0009] According to the present disclosure, an organic compound having high oscillator strength and high luminous efficiency can be provided.

[0010] Other features and advantages of the present disclosure will become apparent from the following description taken in conjunction with the accompanying drawings, in which the same or similar components are designated by the same reference numerals.

[0011] The accompanying drawings are included in and constitute a part of the specification, illustrate embodiments of the present disclosure, and are used, together with the description thereof, to explain the principles of the present disclosure.

[0023] FIG. 1 is a schematic cross-sectional view illustrating an example of a pixel of a display device according to an embodiment of the present disclosure.

[0024] FIG. 2 is a schematic cross-sectional view illustrating an example of a display device using an organic light-emitting element according to an embodiment of the present disclosure.

[0025] FIG. 3 is a schematic view illustrating an example of a display device according to an embodiment of the present disclosure.

[0026] FIG. 4 is a schematic view illustrating an example of an imaging device according to an embodiment of the present disclosure.

[0027] FIG. 5 is a schematic view illustrating an example of an electronic device according to an embodiment of the present disclosure.

[0028] FIG. 6 is a schematic view illustrating an example of a display device according to an embodiment of the present disclosure.

[0029] FIG. 7 is a schematic view illustrating an example of a bendable display device.

[0030] FIG. 8 is a schematic view illustrating an example of an illumination device according to an embodiment of the present disclosure.

[0031] FIG. 9 is a schematic view illustrating an example of a moving object having a vehicle lamp according to an embodiment of the present disclosure.

[0032] FIG. 10 is a schematic view illustrating an example of a wearable device according to an embodiment of the present disclosure.

[0033] FIG. 11 is a schematic view illustrating another example of a wearable device according to an embodiment of the present disclosure.

[0034] FIG. 12 is a schematic view illustrating an example of an image forming apparatus according to an embodiment of the present disclosure.

[0035] FIG. 13 is a schematic view illustrating an example of an exposure light source of an image forming apparatus according to an embodiment of the present disclosure.

[0036] FIG. 14 is a schematic view illustrating an example of an exposure light source of an image forming apparatus according to an embodiment of the present disclosure.

[0012] Hereinafter, embodiments will be described in detail with reference to the accompanying drawings. Note that the following embodiments do not limit the scope of the claims. Although multiple features are described in the embodiments, not all of these multiple features are required, and multiple features may be combined arbitrarily. Furthermore, in the accompanying drawings, the same reference numerals are used to designate the same or similar components, and redundant explanations will be omitted.

[0013] In this specification, examples of halogen atoms include, but are not limited to, fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0014] The alkyl group may have from 1 to 40 carbon atoms, from 1 to 20 carbon atoms, from 1 to 10 carbon atoms, or from 1 to 6 carbon atoms. Specific examples include a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, a tertiary butyl group, a secondary butyl group, an octyl group, a cyclohexyl group, a tertiary pentyl group, a 3-methylpentan-3-yl group, a 1-adamantyl group, and a 2-adamantyl group, but are not limited to these.

[0015] The aryl group may have 5 to 20 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms. Specific examples include, but are not limited to, a phenyl group, a naphthyl group, an indenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a phenanthryl group, a triphenylenyl group, a pyrenyl group, an anthranyl group, a perylenyl group, a chrysenyl group, and a fluoranthenyl group. The heteroaryl group may have 3 to 24 carbon atoms, 3 to 18 carbon atoms, or 3 to 12 carbon atoms. Furthermore, the heteroaryl group may have 6 to 24 carbon atoms, 6 to 18 carbon atoms, or 6 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.

[0016] 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.

[0017] The alkoxy group may have from 1 to 40 carbon atoms, from 1 to 20 carbon atoms, or from 1 to 10 carbon atoms. Specific examples include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, a 2-ethyl-octyloxy group, and a benzyloxy group.

[0018] Specific examples of the aryloxy group include, but are not limited to, a phenoxy group.

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

[0020] Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group and a triphenylsilyl group.

[0021] Examples of substituents that the alkyl group, aryl group, heteroaryl group, amino group, alkoxy group, aryloxy group, heteroaryloxy group, and silyl group may further have include, but are not limited to, halogen atoms such as fluorine, chlorine, bromine, and iodine; alkyl groups such as methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, and tertiary butyl group; alkoxy groups such as methoxy group, ethoxy group, and propoxy group; amino groups such as dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, and ditolylamino group; aryloxy groups such as phenoxy group; aryl groups such as phenyl group and biphenyl group; heteroaryl groups such as pyridyl group and pyrrolyl group; and cyano group.

[0022] (1) Organic Compound First, the organic compound according to the present disclosure will be described. The organic compound according to the present disclosure is a compound represented by the following general formula (1).

[0023]

[0024] <Ring a, Ring b> In general formula (1), ring a and ring b are each independently selected from substituted or unsubstituted aryl rings and substituted or unsubstituted heteroaryl rings. Ring a and ring b may each independently be selected from substituted or unsubstituted aryl rings. Ring a and ring b may be bonded to each other.

[0025] <R1 to R3> In general formula (1), R1 to R3 are each independently selected from 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 heteroaryl 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. R1 to R3 may each independently be selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. R1 to R3 may each independently be selected from a hydrogen atom and a substituted or unsubstituted alkyl group.

[0026] However, at least one of R1 to R3 is independently selected from the group represented by the following general formula (2): One of R1 to R3, for example, R2, may be a group represented by the following general formula (2):

[0027] <R4 to R7, Ring c> In general formula (1), R4 to R7 are each independently selected from 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 heteroaryl 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. R4 to R7 may each independently be selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. R4 to R7 may also be a hydrogen atom.

[0028] However, two adjacent groups from R4 to R7 in one group are bonded to form a c-ring, and the c-ring is a substituted or unsubstituted heteroaryl ring in which a five-membered ring and a six-membered ring are fused. The two adjacent groups from R4 to R7 in one group are R4 and R5, R5 and R6, or R6 and R7. Among these, R6 and R7 may be bonded to form a c-ring. The c-ring may be a benzofuran ring, a benzothiophene ring, or a benzotellurophene ring.

[0029] <X1> In general formula (1), X1 is an oxygen atom or a sulfur atom. X1 may be an oxygen atom.

[0030]

[0031] <Ring d> In general formula (2), ring d is independently selected from a substituted or unsubstituted aryl ring and a substituted or unsubstituted heteroaryl ring formed by condensing a five-membered ring and a six-membered ring. Ring d may be a substituted or unsubstituted heteroaryl ring formed by condensing a five-membered ring and a six-membered ring.

[0032] <X2> In general formula (2), X2 is independently selected from an oxygen atom and a sulfur atom, and may be an oxygen atom.

[0033] <*> In formula (2), * indicates the bonding position to formula (1).

[0034] <Substituents that Rings a to d May Have> Substituents that Rings a to d may have are each independently selected from a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl 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. Substituents that Rings a to d may each independently be selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted phenoxy group.

[0035] <Example of Compound> The organic compound according to this embodiment may be a compound represented by the following general formula (3).

[0036]

[0037] [R4 to R7] In general formula (3), two adjacent groups of R4 to R7 in one pair are bonded to a group represented by general formula (4) below. The two adjacent groups of R4 to R7 in one pair are R4 and R5, R5 and R6, or R6 and R7. Among these, R6 and R7 may be bonded to a group represented by general formula (4) below.

[0038] [R8 to R 16 In general formula (3), R to R 16 are each independently selected from 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 heteroaryl 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. 16may each be independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.

[0039] R8 to R 11 Two adjacent ones of a pair of R to R may be bonded to a group represented by the following general formula (4): 11 The two adjacent pairs of R8 and R9, R9 and R 10 , or R 10 and R 11 Among these, R8 and R9 may be bonded to a group represented by the following general formula (4).

[0040] R8 to R 16 Two adjacent ones of R may be bonded to each other to form a ring, for example, R and R 10 , R 14 and R 15 may be bonded to each other to form a ring. 16 may be connected by a single bond.

[0041]

[0042] [R 17 ~R 20 In general formula (4), R 17 ~R 20 are each independently selected from 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 heteroaryl 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. 17 ~R 20 may each be independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.

[0043] [Y1] In the general formula (4), Y1 is an oxygen atom, a sulfur atom, a selenium atom, or a tellurium atom. Y1 may be an oxygen atom, a sulfur atom, or a tellurium atom.

[0044] [*] In the general formula (4), * indicates the bonding position to the general formula (3).

[0045] <Example of d Ring> The d ring may be a ring represented by the following general formula (5) or (6), or may be a ring represented by the following general formula (5).

[0046]

[0047] [R 21 To R 28 In general formula (5), R 21 To R 28 are each independently selected from 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 heteroaryl 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. 21 ~R 28 One of the R bonds to X. 21 ~R 28 may each be independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.

[0048] [Y2] In the general formula (5), Y2 is an oxygen atom, a sulfur atom, a selenium atom, or a tellurium atom. Y2 may be an oxygen atom, a sulfur atom, or a tellurium atom.

[0049] [R 29 To R 33 In general formula (6), R 29 To R 33 are each independently selected from 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 heteroaryl 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. 29 ~R33 may be each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. 29 ~R 33 may be a hydrogen atom.

[0050] [*] In general formula (6), * indicates the bonding position to X2.

[0051] At least one of the substituents which ring a to ring d may have, R to R, and R to R may be selected from a substituted or unsubstituted alkyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having from 6 to 18 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, and a cyano group, and may be selected from a substituted or unsubstituted alkyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 18 carbon atoms, and a substituted or unsubstituted heteroaryl group having from 6 to 18 carbon atoms from the viewpoint of sublimability, and may have the following structure.

[0052] At least one of the substituents which may be possessed by rings a to d, R1 to R7, and R1 to R7 may be selected from Group A below.

[0053]

[0054] <Characteristics> The characteristics of the organic compound according to this embodiment will be described below. The organic compound according to this embodiment has a structure represented by general formula (1), and therefore exhibits high oscillator strength. In particular, in general formula (1), the c-ring portion is made into a heteroaryl ring, i.e., the π-electron system is expanded, thereby exhibiting high oscillator strength.

[0055] As described in paragraph

[0262] of JP 2020-47930 A and paragraph

[0035] of JP 2022-46999 A, it is known that compounds with high oscillator strength tend to exhibit high quantum yields (luminous efficiencies). Therefore, the oscillator strength of the organic compound may exhibit a high value.

[0056] Tables 1 and 2 show the oscillator strength values ​​of Compound 1-14, an organic compound according to this embodiment, and Comparative Compound 1-15, a comparative example. Compounds 1-6 and Comparative Compound 1-9 are compounds in which the a ring and the b ring are not bonded, while Compounds 7-14 and Comparative Compounds 10-15 are compounds in which the a ring and the b ring are bonded. Furthermore, Comparative Compounds 1, 2, and 10 are compounds in which a heteroaryl ring is bonded to B and X1, Comparative Compounds 3-6, 9, and 11-15 are compounds without a c ring, and Comparative Compounds 7 and 8 are compounds in which the ring corresponding to the c ring is an aryl ring. The oscillator strengths were calculated using Gaussian 16 (Gaussian 16, Revision C.01, M.J. Frisch, et al., Gaussian, Inc., Wallingford, CT, 2019), a molecular orbital calculation software manufactured by Gaussian, Inc., USA. B3LYP / 6-31G was used as the basis function. * was used.

[0057]

[0058]

[0059]

[0060]

[0061] As can be seen from Tables 1 and 2, compounds 1-6 and 7-14, which are organic compounds according to the present embodiment, exhibit higher oscillator strengths than comparative compounds 1-9 and 10-15, respectively. Therefore, the organic compounds according to the present embodiment are organic compounds that exhibit high oscillator strengths. On the other hand, comparative compounds 7 and 8, in which the ring corresponding to ring c is an aryl ring, exhibit lower oscillator strengths than comparative compounds 1 and 2.

[0062] <Exemplary Compounds> Specific examples of organic compounds according to the present disclosure are shown below, although the present disclosure is not limited thereto.

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076] (2) Organic Light-Emitting Element Next, an 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 an emitting layer. The organic compound according to this embodiment may be included in the organic compound layer or may be included in the emitting layer. Here, when the organic compound layer is a laminate consisting of multiple layers, the organic compound layer may have, in addition to the emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole / exciton blocking layer, an electron transport layer, an electron injection layer, etc. Furthermore, the emitting layer may be a single layer or a laminate consisting of multiple layers. When the emitting layer is a multiple layer, a charge generation layer may be included between the emitting layers. The charge generation layer may be composed of a compound having a LUMO (lowest unoccupied molecular orbital) energy level lower than the LUMO energy level of the hole transport layer, and the LUMO energy level of the charge generation layer may be lower than the HOMO (highest occupied molecular orbital) energy level of the hole transport layer. Here, the HOMO energy level and LUMO energy level of the organic compound layer may be the HOMO energy level and LUMO energy level of the organic compound having the largest mass ratio in the organic compound layer.

[0077] 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.

[0078] In this specification, the HOMO energy level and the LUMO energy level can be calculated using molecular orbital calculations. The molecular orbital calculations are performed using density functional theory (DFT) or the like, with the functional being B3LYP and the basis set being 6-31G. *It may be performed using, etc. Note that 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. Hasegawa, 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. Klen, 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.).

[0079] The HOMO energy level and LUMO energy level herein can be calculated using the ionization potential and band gap.

[0080] 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-2. 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 the excitation light.

[0081] 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.

[0082] In an organic light-emitting device according to an embodiment of the present disclosure, when the organic compound according to this embodiment is contained in the light-emitting layer, the light-emitting layer may be a layer consisting solely of the organic compound according to this embodiment, or may be a layer consisting of the organic compound according to this embodiment and other compounds. When the light-emitting layer is a layer consisting of the organic compound according to this embodiment and other compounds, the organic compound according to this embodiment may be used as a host material or a guest material in the light-emitting layer. It may also be used as an assist material that can be contained in the light-emitting layer. The host material, also referred to as a "host" or "first compound," is the compound with the largest mass ratio among the compounds constituting the light-emitting layer. The guest material, also referred to as a "guest," "dopant material," "dopant," or "third compound," is a compound that is smaller in mass ratio than the host among the compounds constituting the light-emitting layer and is responsible for the primary emission of light. Therefore, the guest material is sometimes also referred to as the light-emitting material. The assist material, also referred to as an "assist" or "second compound," is a compound that is smaller in mass ratio than the host material among the compounds constituting the light-emitting layer and assists the emission of the guest material. The assist material is also referred to as a second host.

[0083] 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 this embodiment may be any of a guest material, an assist material, and a host material. In this case, the organic light-emitting element according to this embodiment may satisfy S1(H) > S1(D) or S1(H) > S1(A) > S1(D). When the lowest excited singlet energy of the compound contained in the organic light-emitting element according to this embodiment satisfies the above relationship, excitons can be efficiently transferred to the guest material, resulting in an organic light-emitting element with superior luminous efficiency.

[0084] When the organic compound according to this embodiment is used in the light-emitting layer, the concentration of the organic compound according to this embodiment may be 0.01% by mass or more and 99% by mass or less, based on the entire light-emitting layer. When the light-emitting layer is composed of the first compound and the organic compound according to this embodiment, the concentration of the organic compound according to this embodiment may be 0.01% by mass or more and 50% by mass or less, based on the entire light-emitting layer. When the light-emitting layer is composed of the first compound, the second compound, and the organic compound according to this embodiment, the concentration of the organic compound according to this embodiment may be 1% by mass or more and 50% by mass or less, based on the entire light-emitting layer.

[0085] The present inventors have conducted various studies and found that by using the organic compound according to this embodiment in the light-emitting layer, an element can be obtained that exhibits highly efficient, high-brightness light output and is extremely durable. This light-emitting layer may be a single layer or multiple layers, and it is also possible to mix colors by including a light-emitting material having another light-emitting color. Multiple layers refer to a state in which a light-emitting layer and another light-emitting layer are stacked. In this case, the light-emitting color of the organic light-emitting element is not limited to a single color. More specifically, it may be white or a neutral color. In the case of white, when the light-emitting layer emits, for example, blue, 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.

[0086] The organic compound according to this embodiment can be used as a constituent material of an organic compound layer other than the light-emitting layer that constitutes the organic light-emitting device according to this embodiment. Specifically, it may be used as a constituent material of an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, a hole blocking layer, etc. In this case, the emission color of the organic light-emitting device is not limited to a single color. More specifically, it may emit white light or an intermediate color.

[0087] <Other Compounds> In addition to the organic compound according to this embodiment, conventionally known low-molecular-weight and high-molecular-weight hole-injecting or hole-transporting compounds, host materials, light-emitting compounds, electron-injecting or electron-transporting compounds, etc. may also be used together as needed. Examples of these compounds are listed below.

[0088] The hole injection / transport material may be a material with high hole mobility that facilitates hole injection from the anode and transports the injected holes to the light-emitting layer. It may also be a material with a high glass transition temperature that suppresses crystallization of organic compounds in organic light-emitting devices. Examples of low-molecular-weight and high-molecular-weight materials with hole injection / transport properties include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. Furthermore, the above-mentioned hole injection / transport materials can also be used in electron blocking layers. Furthermore, when the hole injection layer is prepared by a coating method, a mixture of polyethylenedioxythiophene and polystyrene sulfonic acid (PEDOT:PSS), which is commonly used as a hole injection material, may also be used. Specific examples of compounds that can be used as hole injection / transport materials are listed below, but of course, they are not limited to these.

[0089]

[0090] Among the hole injection and transport materials listed above, HT16 to HT18 can reduce the driving voltage when used in a layer in contact with the anode. HT16 is widely used in organic light-emitting devices. HT2 to HT7, HT10, HT12, and HT22 to HT28 may be used in an organic compound layer adjacent to HT16. Hole-transporting polymer compounds such as polyphenylene vinylene (PPV), polyfluorene (PF), polyvinyl carbazole (PVK), and derivatives thereof may also be used. In addition, inorganic insulator layers such as SiO2 and SiN, and organosilicon polymers such as siloxane may also be used. Multiple materials may also be used in a single organic compound layer.

[0091] Examples of guest materials primarily involved in light-emitting function include donor-acceptor organic compounds, boron-containing complexes, indocarbazole fused ring compounds, fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, organoaluminum complexes such as tris(8-quinolinolato)aluminum, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, and polymer derivatives such as poly(phenylenevinylene) derivatives, poly(fluorene) derivatives, and poly(phenylene) derivatives. Furthermore, when preparing a light-emitting layer using a coating method, polymer compounds with light-emitting properties are primarily used. This is because polymer compounds tend to exhibit high glass transition temperatures and are therefore less prone to crystallization than low-molecular-weight compounds. Specific examples of materials that can be used include polymer compounds such as polyphenylene vinylene (PPV), polyfluorene (PF), polyvinyl carbazole (PVK), and derivatives thereof. Specific examples of compounds that can be used as the light-emitting material are shown below, but the light-emitting material is not limited to these.

[0092]

[0093]

[0094]

[0095] Specific examples of compounds that can be used as the host material or assist material contained in the light-emitting layer are shown below, but the present invention is not limited to these.

[0096]

[0097]

[0098] [Assist Dopant] The organic compound of this embodiment may be used together with a compound represented by the following general formula (13-1) to general formula (14-2). In other words, the composition of this embodiment may contain the organic compound of this embodiment and an organic compound represented by any one of general formulas (13-1) to (14-2). The organic compound represented by any one of general formulas (13-1) to (14-2) may be used as an assist dopant material for the light-emitting layer.

[0099]

[0100]

[0101] In the general formulae (13-1) and (14-2), R 11 ~R 13 , R 31 and R 32 represents a substituent, which is independently selected from a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a cyano group, and a silyl group.

[0102] n is an integer of 0 to 2, n' and n" are integers of 0 to 4, and m and m' are integers of 0 to 5. When n, n', n", m, and m' are 2 or more, a plurality of R 11 ~R 13 , R 31 and R 32 They may be the same or different from each other.

[0103] R 21 ~R 24 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a cyano group, and a silyl group. 21 ~R 24 At least one of the groups may be a substituted or unsubstituted alkyl group.

[0104] X is an oxygen atom, a sulfur atom, a selenium atom, or a tellurium atom.

[0105] Representative examples of these compounds include, but are not limited to, the following:

[0106]

[0107]

[0108]

[0109]

[0110] 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 can also be used in hole-blocking layers. Specific examples of compounds used as electron transport materials are listed below, but of course, are not limited to these.

[0111]

[0112]

[0113] The electron injection material can be arbitrarily selected from those that allow easy electron injection from the cathode, and is selected taking into consideration 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. They can also be used in combination with the above-mentioned electron transport materials.

[0114] <Configuration of Organic Light-Emitting Element> 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 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. Either the first electrode or the second electrode may be an anode, and the other may be a cathode.

[0115] [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.

[0116] [Electrodes] A pair of electrodes can be used. The pair of electrodes may be an anode and a cathode. When an electric field is applied in the direction in which the organic light-emitting element emits light, the electrode with 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.

[0117] The anode material should preferably 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.

[0118] 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.

[0119] 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 technology can be used to form the electrode.

[0120] On the other hand, materials with a low work function are preferred for the cathode. 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. Silver can be used, and a silver alloy can be used 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.

[0121] 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, etc., provide good film coverage and are easy to reduce resistance.

[0122] [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, it may contain copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, etc. 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.

[0123] 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 element according to an embodiment of the present disclosure are formed by the method described below.

[0124] The organic compound layer constituting the organic light-emitting device according to an embodiment of the present disclosure can be formed by dry processes such as vacuum deposition, ionization deposition, sputtering, plasma, etc. Alternatively, instead of a 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 (e.g., spin coating, casting, microgravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, screen printing, flexographic printing, offset printing, inkjet printing, capillary coating, nozzle coating, etc.). Among these, vacuum deposition, ionization deposition, inkjet printing, nozzle coating, etc. can be used to manufacture large-area organic light-emitting devices.

[0125] When forming a light-emitting layer using a compound having high solubility in an organic solvent among the organic compounds of this embodiment, the light-emitting layer may be formed by a coating method. Examples of the coating method include spin coating, slit coating, printing, inkjet printing, dispensing, and spraying. Alternatively, the light-emitting layer may be formed by a vacuum deposition method.

[0126] Here, when a layer is formed by a vacuum deposition method or a solution coating method, crystallization is unlikely to occur and the layer has excellent stability over time. When a film is formed by a coating method, the film can be formed by combining with an appropriate binder resin.

[0127] 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.

[0128] 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.

[0129] The thickness of each layer in the organic light-emitting device may generally be 1 nm to 10 μm. In particular, the thickness of the light-emitting layer of the organic compound layer may be 10 nm to 100 nm to obtain effective light-emitting characteristics.

[0130] [Protective Layer] A protective layer may be provided on the second electrode. For example, by adhering glass with a moisture absorbent on the second electrode, the infiltration of water and other contaminants 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 second electrode to reduce the infiltration of water and other contaminants into the organic compound layer. For example, after forming the second electrode, the second electrode may be transferred to another chamber without breaking the vacuum, and a 2 μm-thick silicon nitride film may be formed by CVD to serve as a protective layer. A protective layer may be provided using atomic layer deposition (ALD) after the CVD film formation. The material of the film formed by ALD is not limited, and may be silicon nitride, silicon oxide, aluminum oxide, or the like. Silicon nitride may be further formed on the film formed by ALD by CVD. The film formed by ALD may have a smaller thickness than the film formed by CVD. 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.

[0131] [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.

[0132] [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 may be a high molecular weight.

[0133] 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.

[0134] [Microlens] The organic light-emitting element 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.

[0135] 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.

[0136] [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.

[0137] [Pixel Circuit] An organic light-emitting device having an organic light-emitting element may have a pixel circuit connected to the organic 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.

[0138] The light-emitting device has a display region and a peripheral region arranged around the display region. The display region has a pixel circuit, and the peripheral region has a display control circuit. The mobility of a transistor constituting the pixel circuit may be smaller than the mobility of a transistor constituting the display control circuit. The slope of the current-voltage characteristics of the transistor constituting the pixel circuit may be smaller than the slope of the current-voltage characteristics of the transistor constituting the display control circuit. The slope of the current-voltage characteristics can be measured by the so-called Vg-Ig characteristics. The transistor constituting the pixel circuit is a transistor connected to a light-emitting element, such as a first light-emitting element.

[0139] [Pixel] An organic light-emitting device having an organic light-emitting element may have a plurality of pixels. Each pixel has sub-pixels that emit different colors. The sub-pixels may each emit RGB light, for example.

[0140] A pixel has an area, also called a pixel aperture, from which light is emitted. 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. The distance between subpixels may be 10 μm or less, more specifically, it may be 8 μm, 7.4 μm, or 6.4 μm.

[0141] 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.

[0142] The organic light-emitting device according to this embodiment can be used as a component of a display device or a lighting device. Other applications 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.

[0143] 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, or the like, an information processing unit that processes the input information, and displays the input image on a display unit. The display device may have a plurality of pixels, at least one of which may have the organic light-emitting element of this embodiment and an active element such as a transistor connected to the organic light-emitting element. In this case, the substrate may be a semiconductor substrate such as silicon, and the transistor may be a MOSFET formed on the substrate. The image display device has an input unit for inputting image information and a display unit for outputting an image, and the display unit includes the display device of this embodiment. The image display device may also have a display unit having the organic light-emitting element of this embodiment and a housing in which the display unit is provided.

[0144] 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.

[0145] Next, a display device according to this embodiment will be described with reference to the drawings. Fig. 1 is a cross-sectional view 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).

[0146] 1A is a cross-sectional schematic diagram of an example of a pixel, which is a component of a display device according to this embodiment. The pixel includes subpixels 10. The subpixels 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 subpixels may be selectively transmitted or color-converted using a color filter or the like. Each subpixel 10 includes a reflective electrode serving as a first electrode 2 on an interlayer insulating layer 1, an insulating layer 3 covering the edge of the first electrode 2, an organic compound layer 4 covering the first electrode 2 and the insulating layer 3, a transparent electrode serving as a second electrode 5, a protective layer 6, and a color filter 7.

[0147] A transistor and a capacitor element may be disposed below or inside the interlayer insulating layer 1. The transistor and the first electrode 2 may be electrically connected via a contact hole or the like (not shown).

[0148] The insulating layer 3 is also called a bank or a pixel separation film. It covers the edges of the first electrode 2 and is disposed to surround the first electrode 2. The portion where the insulating layer 3 is not disposed is in contact with the organic compound layer 4 and becomes a light-emitting region.

[0149] The organic compound layer 4 includes a hole injection layer 41 , a hole transport layer 42 , a light emitting layer 43 , a hole blocking layer 44 , and an electron transport layer 45 .

[0150] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0151] The protective layer 6 reduces the penetration of moisture into the organic compound layer 4. Although the protective layer 6 is illustrated as being one layer, it may be a multi-layer structure, with each layer being an inorganic compound layer and an organic compound layer.

[0152] The color filters 7 are divided into 7R, 7G, and 7B depending on their colors. The color filters 7 may be formed on a planarization film (not shown). A resin protective layer (not shown) may be provided on the color filters 7. The color filters 7 may be formed on a protective layer 6. Alternatively, the color filters 7 may be provided on an opposing substrate such as a glass substrate and then bonded thereto.

[0153] The display device 100 in FIG. 1B has an organic light-emitting element 26 and a TFT 18, which is 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 such as the TFT 18 is disposed on the insulating layer 12, and a gate electrode 13 of the active element, a gate insulating film 14, and a semiconductor layer 15 are provided. The TFT 18 has a drain electrode 16 and a source electrode 17. An insulating film 19 is provided on top of the TFT 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 19.

[0154] The electrical connection between the electrodes (anode 21, cathode 23) included in the organic light-emitting element 26 and the electrodes (source electrode 17, drain electrode 16) included in the TFT 18 is not limited to the mode shown in Fig. 1B. In other words, it is sufficient that either the anode 21 or the cathode 23 is electrically connected to either the source electrode 17 or the drain electrode 16 of the TFT 18.

[0155] 1B, the organic compound layer 22 is illustrated as a single layer, but may be a multi-layer organic compound layer 22. A first protective layer 24 and a second protective layer 25 are provided on the cathode 23 to reduce deterioration of the organic light-emitting element 26.

[0156] In the display device 100 of FIG. 1B, a transistor is used as the switching element, but other switching elements such as MIM elements may be used instead.

[0157] Also, the transistor used in the display device 100 of FIG. 1B is not limited to a thin film transistor having an active layer on the insulating surface of the substrate, and a transistor using a single crystal silicon wafer may also be used. 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 a thin film transistor is also called a TFT element.

[0158] 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.

[0159] The organic light emitting element according to the present embodiment has its emission luminance controlled by a TFT which is an example of a switching element, and an image can be displayed by the respective emission luminances by providing a plurality of organic light emitting elements in a plane. Note that the switching element according to the present embodiment is not limited to a TFT, and may be a transistor formed of low temperature polysilicon or an active matrix driver formed on a substrate such as a Si substrate. "On the substrate" can also mean "in the substrate". Whether to provide a transistor in the substrate or use a TFT is selected according to the size of the display portion. For example, if the size is about 0.5 inches, an organic light emitting element may be provided on a Si substrate.

[0160] 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. The touch panel 1003 and the display panel 1005 are connected by flexible printed circuits FPCs 1002 and 1004. 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.

[0161] 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.

[0162] 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.

[0163] The display device according to this embodiment may be used as a display unit of an imaging device having an optical unit with a plurality of lenses and an imaging element that receives light that has passed through the optical unit. 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.

[0164] 3A is a schematic diagram showing an example of an imaging device according to this embodiment. The imaging device 1100 may include a viewfinder 1101, a rear display 1102, an operation unit 1103, and a housing 1104. The viewfinder 1101 and the rear display 1102 may include a display device according to this embodiment. In this case, the display device may display not only an 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.

[0165] Since the optimum timing for capturing an image is very short, it is better to display information as soon as possible. Therefore, a display device using the organic light-emitting element of this embodiment may be used. This is because the organic light-emitting element has a fast response speed. A display device using the organic light-emitting element can be used more effectively than a liquid crystal display device, which requires a high display speed.

[0166] 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.

[0167] 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 1202 may be a biometric recognition unit that recognizes a fingerprint to perform operations such as unlocking. An electronic device having a communication unit can also be called a communication device. The electronic device 1200 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 1201. Examples of the electronic device 1200 include a smartphone and a laptop computer.

[0168] FIG. 4 is a schematic diagram 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 has a frame (housing) 1301 and a display unit 1302. The display unit 1302 may use a light-emitting element according to this embodiment. The display device 1300 has the frame 1301 and a base 1303 that supports the display unit 1302. The base 1303 is not limited to the form shown in FIG. 4A . The lower side of the frame 1301 may also serve as the base. The frame 1301 and the display unit 1302 may be curved. The radius of curvature may be 5000 mm or more and 6000 mm or less.

[0169] 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 a 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.

[0170] 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 (optical filter) 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.

[0171] 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.

[0172] 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.

[0173] 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 lamp. The automobile 1500 has tail lamps 1501 and a body 1503, and may be configured so that the tail lamps 1501 are turned on when the brakes are applied, for example. The body 1503 may also be referred to as a fuselage. The automobile 1500 may have windows 1502 attached to the body 1503.

[0174] The tail lamp 1501 may include the organic light-emitting element according to this embodiment. The tail lamp 1501 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 may be made of polycarbonate or the like. Polycarbonate may be mixed with a furandicarboxylic acid derivative, an acrylonitrile derivative, or the like.

[0175] 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 this embodiment are made of transparent materials.

[0176] The moving body according to this embodiment includes one or both of a driving force generating unit that generates a 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, an aircraft's propeller, etc.

[0177] Specifically, the moving object according to this embodiment may be a bicycle, an automobile, a train, a ship, an aircraft, a drone, or the like. The moving object may have a body and a lamp provided on the body. The lamp may emit light to indicate the position of the body. The lamp may have the organic light-emitting element according to this embodiment.

[0178] An application example of the display device of each of the above-described embodiments will be described with reference to Fig. 6. The display device can be applied to a system that can be worn as a wearable device, such as smart glasses, a head-mounted display, or a smart contact lens. A display device that can be used in a wearable device may have an imaging device that can photoelectrically convert visible light and a display device that can emit visible light.

[0179] Fig. 6A is a schematic diagram illustrating an example of a wearable device according to an embodiment of the present disclosure. Using Fig. 6A , glasses 1600 (smart glasses) according to one application example will be described. The glasses 1600 have a display unit on the back side of lenses 1601. The display unit may include an organic light-emitting element according to this embodiment. Furthermore, an imaging device 1602 such as a CMOS sensor or a SPAD may be provided on the front side of the lenses 1601.

[0180] 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.

[0181] FIG. 6B is a schematic diagram illustrating another example of a wearable device according to an embodiment of the present disclosure. Using FIG. 6B , glasses 1610 (smart glasses) according to one application example will be described. The glasses 1610 include a control device 1612, which is provided with a display device having an organic light-emitting element according to this embodiment. The control device 1612 may further include an imaging device corresponding to the imaging device 1602. An optical system for projecting light emitted from the control device 1612 is formed in the lens 1611, 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 also controls the operation of the imaging device and the display device.

[0182] The control device 1612 may have a gaze detection unit that detects the gaze of the wearer. The gaze detection may use infrared rays. The infrared light emitting unit emits infrared rays toward the eyeball of the user who is gazing at the displayed image. An imaging unit having a light receiving element detects the reflected light from the eyeball of the emitted infrared light, thereby obtaining an image of the eyeball. By having 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.

[0183] 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 based on a Purkinje image formed by reflection of irradiated light on the cornea can be used. More specifically, gaze detection processing based on the pupil-corneal reflex method is performed. Using the pupil-corneal reflex method, a gaze vector representing the direction (rotation angle) of the eyeball is generated based on the image of the pupil and the Purkinje image included in the captured image of the eyeball, thereby detecting the user's gaze.

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

[0185] 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.

[0186] 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 may be applied to, for example, 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.

[0187] 7A is a schematic diagram illustrating an example of an image forming apparatus according to an embodiment of the present disclosure. 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 includes the organic light-emitting element according to this 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 recording medium (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.

[0188] 7B and 7C are diagrams showing an exposure light source 28 and are schematic diagrams illustrating a state in which multiple light-emitting units 36 are arranged on a long substrate. Arrow 37 is a direction parallel to the axis of the photoconductor and represents the column direction in which the organic light-emitting elements are arranged. This column direction is the same as the axis direction about which the photoconductor 27 rotates. This direction can also be referred to as the long axis direction of the photoconductor 27. FIG. 7B shows a configuration in which the light-emitting units 36 are arranged along the long axis of the photoconductor 27. FIG. 7C shows a configuration different from that shown in FIG. 7B, in which the light-emitting units 36 are arranged alternately in the column direction in the first and second columns. The first and second columns are arranged at different positions in the row direction. In the first column, multiple light-emitting units 36 are arranged at intervals. In the second column, the light-emitting units 36 are located at positions corresponding to the intervals between the light-emitting units 36 in the first column. In other words, multiple light-emitting units 36 are also arranged at intervals in the row direction. The arrangement in FIG. 7C can also be described as a grid arrangement, a houndstooth arrangement, or a checkerboard pattern.

[0189] 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.

[0190] (3) Ink Composition Next, the ink composition according to this embodiment will be described. The ink composition according to this embodiment contains at least one organic compound according to this embodiment. By using the ink composition according to this embodiment, it becomes possible to prepare a layer made of an organic compound that constitutes the organic light-emitting device according to this embodiment, particularly a light-emitting layer, by a coating method, and a large-area device can be easily produced at a relatively low cost.

[0191] Examples of solvents that dissolve the organic compound of this embodiment include toluene, xylene, mesitylene, dioxane, methylnaphthalene, tetrahydrofuran, diglyme, 1,2-dichlorobenzene, and 1,2-dichloropropane. These solvents can be used alone or in combination of two or more. Among these, solvents with an appropriate evaporation rate, specifically a solvent with a boiling point of about 70°C to 200°C, may be used in order to easily obtain a thin film with a uniform thickness.

[0192] The ink composition according to this embodiment may also contain other compounds that serve as additives, such as the above-mentioned known light-emitting layer hosts or light-emitting assist materials, hole transport materials, light-emitting materials, and electron transport materials.

[0193] The concentration of the organic compound of this embodiment in the ink composition of this embodiment is, for example, 0.05 wt % or more and 20 wt % or less, and may be 0.1 wt % or more and 5 wt % or less, based on the total weight of the composition.

[0194] The ink composition according to this embodiment can be formed into a film by a spin coating method, a bar coating method, a slit coating method, an inkjet method, a nozzle coating method, a casting method, a gravure printing method, etc. The organic light-emitting element according to this embodiment can be used to construct a display device such as a display by forming a layer containing the organic compound according to this embodiment on an electrode formed in a pixel pattern.

[0195] The present disclosure will be described below with reference to examples, although the present disclosure is not limited thereto.

[0196] Example 1 (Synthesis of Compounds)

[0197] (1) Synthesis of Exemplary Compound 1 (Compound 1 of Chemical Formula 10) (1-1) 1,1'-((5-bromo-2-methyl-1,3-phenylene)bis(oxy))didibenzo[b,d]furan (Compound (A-1)) Under a nitrogen atmosphere, dibenzo[b,d]furan-1-ol (11.8 g, 64.0 mmol), cesium carbonate (19.9 g, 61.1 mmol), and 5-bromo-1,3-difluoro-2-methylbenzene (2.60 mL, 19.9 mmol) were suspended in NMP (140 mL) and stirred at 170°C for 22 hours. After allowing to cool, saturated saline and toluene were added to the reaction mixture, and the organic layer was separated. The organic layer was dried over sodium sulfate, and the filtrate was evaporated under reduced pressure. A mixed solution of hexane / dichloromethane (4:1, v / v) was added to the resulting residue, and the precipitated solid was filtered and washed with acetonitrile and hexane to obtain the target compound (A-1) as a colorless solid (5.9 g, 11.0 mmol, 55%).

[0198] 1 H NMR (400MHz, CDCl3) δ (ppm): 2.34 (s, 3H), 6.79 (dd, J = 7.5, 1.2Hz, 2H), 6.97 (s, 2H ), 7.34-7.44 (m, 6H), 7.47-7.51 (m, 2H), 7.61 (d, J=8.2Hz, 2H), 8.02-8.04 (m, 2H)

[0199] ​(1-2) 3,5-bis(dibenzo[b,d]furan-1-yloxy)-4-methyl-N,N-di-p-tolylaniline (Compound (A-2)) Compound (A-1) (1.0 g, 1.9 mmol), p,p'-ditolylamine (0.41 g, 2.1 mmol), palladium acetate (5.1 mg, 0.023 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.018 mg, 0.062 mmol), and sodium tert-butoxide (0.35 g, 3.6 mmol) were suspended in toluene (20 mL) under a nitrogen atmosphere, and the suspension was stirred at 100°C for 22 hours. After allowing to cool, water and methylene chloride were added to the reaction mixture, and the organic layer was separated. The organic layer was dried over sodium sulfate, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (Hexane only → Hexane:CH2Cl2 = 7:3, v / v) to obtain the target compound (A-2) as a colorless solid (0.98 g, 1.5 mmol, 79%).

[0200] 1 H NMR (400MHz, CD2Cl2) δ (ppm): 2.19-2.208m, 9H), 6.49 (s, 2H), 6.76-6.82 (m, 6H), 6.88 (d, J = 7.8Hz, 4H), 7.28 (dd, J=8.2, 0.7Hz, 2H), 7.34-7.40 (m, 4H), 7.47-7.51 (m, 2H), 7.59 (dt, J=8.2, 0.7Hz, 2H), 8.01-8.03 (m, 2H) MS (MALDI-TOF): m / z calcd for C 45 H 33 NO4 651.241; found 651.244 ([M] + ).

[0201] ​(1-3) 7-(dibenzo[b,d]furan-1-yloxy)-6,12-dimethyl-9-(-tolyl)-9H-5,16-dioxa-9-aza-13b-boraindeno[1,2-a]naphtho[1,2,3-fg]anthracene (Exemplary Compound 1) Compound (A-2) (0.30 g, 0.46 mmol) was suspended in 1,2,4-trichlorobenzene (10 mL) under a nitrogen atmosphere. Boron triiodide (0.99 g, 2.5 mmol) was added to this suspension, and the mixture was stirred at 150°C for 19 hours. After cooling, a saturated aqueous solution of sodium sulfite and methylene chloride were added to the reaction mixture, and the organic layer was separated. The organic layer was dried over sodium sulfate, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane only → hexane:CH2Cl2 = 7:3, v / v) to obtain the desired exemplary compound 1 as a pale yellow solid (0.19 g, 0.29 mmol, 62%).

[0202] 1 H NMR (400MHz, CD2Cl2) δ (ppm): 2.40 (s, 3H), 2.52 (s, 3H), 2.77 (s, 3H), 5.90 (s, 1H), 6.70-6.75 (m, 2H), 6.91 (d, J = 8.2Hz, 2H), 7.19 ( d, J=7.8Hz, 2H), 7.22-7.26 (m, 1H), 7.27-7.32 (m, 3H), 7.43-7.47 (m, 1H), 7.49- 7.58 (m, 2H), 7.60 (d, J=8.2Hz, 1H), 7.68 (d, J=8.5Hz, 1H), 7.69-7.72 (m, 1H), 7. 80-7.83 (m, 1H), 8.61-8.64 (m, 1H), 8.74 (d, J = 1.5Hz, 1H), 8.95 (d, J = 8.5Hz, 1H) MS (MALDI-TOF): m / z calcd for C 45 H 30 BNO4 659.227; found 659.253 ([M] + ).

[0203] ​(2) Synthesis of Exemplary Compound 2 (Compound 2 of Chemical Formula 10) (2-1) 1,1'-((5-bromo-2-methyl-1,3-phenylene)bis(oxy))didibenzo[b,d]thiophene (Compound (B-1)) Under a nitrogen atmosphere, dibenzo[b,d]thiophen-1-ol (5.0 g, 24.9 mmol), cesium carbonate (8.1 g, 24.9 mmol), and 5-bromo-1,3-difluoro-2-methylbenzene (1.0 mL, 7.7 mmol) were suspended in 1-methyl-2-pyrrolidone (100 mL) and stirred at 170°C for 18 hours. After allowing to cool, saturated saline and toluene were added to the reaction mixture, and the organic layer was separated. The organic layer was dried over sodium sulfate, and the filtrate was evaporated under reduced pressure. Acetonitrile was added to the resulting residue, and the precipitated solid was filtered and washed with hexane to obtain the target compound (B-1) as a colorless solid (2.8 g, 4.9 mmol, 64%).

[0204] 1 H NMR (400MHz, CDCl3) δ (ppm): 2.33 (s, 3H), 6.85 (dd, J = 8.0, 0.6Hz, 2H), 7.00 (s, 2H), 7.41 (t, J = 8.0H, 2H), 7.45-7.52 (m, 4H), 7.64 (dd, J=8.0, 0.6Hz, 2H), 7.88-7.91 (m, 2H), 8.59-8.60 (m, 2H)

[0205] ​(2-2) 3,5-bis(dibenzo[b,d]thiophen-1-yloxy)-4-methyl-N,N-di-p-tolylaniline (compound (B-2)) Compound (B-1) (0.50 g, 0.88 mmol), p,p'-ditolylamine (0.20 g, 1.0 mmol), palladium acetate (7.3 mg, 0.033 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.011 mg, 0.038 mmol), and sodium-tert-butoxide (0.17 g, 1.8 mmol) were suspended in toluene (10 mL) under a nitrogen atmosphere, and the suspension was stirred at 100°C for 30 hours. After allowing to cool, water and methylene chloride were added to the reaction mixture, and the organic layer was separated. The organic layer was dried over sodium sulfate, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (Hexane:CHCl=7:3, v / v) to give the target compound (B-2) as a colorless solid (0.54 g, 0.78 mmol, 89%).

[0206] 1 H NMR (400MHz, CD2Cl2) δ (ppm): 2.14 (s, 3H), 2.22 (s, 6H), 6.58 (s, 2H), 6.83 (dd, J=8.0, 0.8Hz, 2H), 6.90-6.92 (m, 4H), 6.96 ( d, J = 8.3Hz, 4H), 7.38 (t, J = 8.0Hz, 2H), 7.45-7.50 (m, 4H), 7.55 (dd, J = 7.9, 0.8Hz, 2H), 7.87-7.89 (m, 2H), 8.64-8.66 (m, 2H) MS (MALDI-TOF): m / z calcd for C 45 H 33 BNO2S2 683.195; found 683.304 ([M] + ).

[0207] ​(2-3) 7-(dibenzo[b,d]thiophen-1-yloxy)-6,12-dimethyl-9-(p-tolyl)-9H-5-oxa-16-thia-9-aza-13b-boraindeno[1,2-a]naphtho[1,2,3-fg]anthracene (Exemplary Compound 2) Compound (B-2) (0.30 g, 0.46 mmol) was suspended in 1,2,4-trichlorobenzene (10 mL) under a nitrogen atmosphere. Boron triiodide (0.99 g, 2.5 mmol) was added to this suspension, and the mixture was stirred at 150°C for 19 hours. After allowing to cool, a saturated aqueous sodium sulfite solution and methylene chloride were added to the reaction mixture, and the organic layer was separated. The organic layer was dried over sodium sulfate, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane only → hexane:CH2Cl2 = 7:3, v / v), and the solid was washed with methanol and hexane to give the desired compound 2 as a yellow solid (0.068 g, 0.098 mmol, 21%).

[0208] 1 H NMR (400MHz, CD2Cl2) δ (ppm): 2.42 (s, 3H), 2.53 (s, 3H), 2.76 (s, 3H), 6.05 (s, 1H), 6.71 (dd, J=8.0, 0.7Hz, 1H), 6.75 (d, J=8.7Hz, 1H), 7.05 (d, J=8.0Hz, 2H), 7.26-7.32 (m, 4H), 7.38-7.42 (m, 1H), 7.44-7.48 (m, 1H), 7.51-7.61 (m, 3H), 7.88-7.92 (m, 2H), 7.96-7.98 ( m, 1H), 8.55-8.58 (m, 1H), 8.7 (d, J = 1.3Hz, 1H), 8.89 (d, J = 8.3Hz, 1H), 9.30-9.32 (m, 1H) MS (MALDI-TOF): m / z calcd for C 45 H 30 BNO2S2 691.181; found 691.324 ([M] + ).

[0209] (3) Synthesis of Exemplary Compound 3 (Compound 5 of Chemical Formula 10)

[0210] ​(3-1) N-(3,5-bis(dibenzo[b,d]thiophen-1-yloxy)-4-methylphenyl)-N-(9,9 -dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine (compound (C-1)) Under a nitrogen atmosphere, compound (B-1) (0.146 g, 0.36 mmol), Bis(9,9-dimethyl-9H-fluoren-2-yl)amine (0.188 g, 0.33 mmol), palladium acetate (3.0 mg, 0.013 mmol), tri-tert-butylphosphonium tetrafluoroborate (3.8 mg, 0.013 mmol), and sodium tert-butoxide (0.064 g, 0.66 mmol) were suspended in toluene (10 mL) and stirred at 100°C for 22 hours. After cooling, water and methylene chloride were added to the reaction mixture, and the organic layer was separated. The organic layer was dried over magnesium sulfate, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (Hexane only → Hexane:CH2Cl2 = 7:3, v / v) to obtain the target compound (C-1) as a colorless solid (0.074 g, 0.083 mmol, 25%).

[0211] 1 H-NMR (500MHz, METHYLENE-CHLORI) δ8.67-8.69 (m, 2H), 7.85-7.87 (m, 2H), 7.59 (d, J = 6.7Hz, 2H), 7.47-7.53 (m, 8H), 7. 37 (t, J = 8.1Hz, 4H), 7.20-7.29 (m, 6H), 7.02-7.03 (m, 2H), 6.89 (d, J = 8.9Hz, 2H), 6.78 (s, 2H), 2.25 (s, 3H), 1.31 (s, 12H) MS (MALDI-TOF): m / z calcd for C 61 H 45 NO2S2 887.289; found 887.261 ([M] + ).

[0212] ​(3-2) 7-(dibenzo[b,d]thiophen-1-yloxy)-9-(9,9-dimethyl-9H-fluoren-2-yl)-6,11,11-trimethyl-9,11-dihydro-5-oxa-19-thia-9-aza-16b-boraindeno[1,2-a]indeno[2′,1′:6,7]naphtho[1,2,3-fg]anthracene (Exemplary Compound 3) Under a nitrogen atmosphere, compound (C-1) (0.050 g, 0.056 mmol) was suspended in chlorobenzene (3 mL). Boron triiodide (0.12 g, 0.306 mmol) was added to this suspension and stirred at 100°C for 2 hours. After cooling, saturated aqueous sodium sulfite and methylene chloride were added to the reaction mixture, and the organic layer was separated. The organic layer was dried over magnesium sulfate, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane only → hexane:CH2Cl2 = 7:3, v / v). The resulting solid was washed with methanol and hexane to obtain the desired exemplary compound 3 as a yellow solid (0.013 g, 0.0145 mmol, 26%).

[0213] 1 H-NMR (500MHz, METHYLENE-CHLORI) δ9.39-9.42 (m, 1H), 9.28 (s, 1H), 9.05 (d, J = 8.3Hz, 1H), 8.52 (d, J = 13 0Hz, 1H), 8.02 (t, J = 11.6Hz, 3H), 7.83 (q, J = 7.5Hz, 3H), 7.64-7.67 (m, 1H), 7.56-7.59 (m, 1H), 7.49 (d, J = 8.3Hz, 1H), 7.35-7.45 (m, 8H), 7.30 (t, J = 7.5Hz, 1H), 7.21 (t, J = 7.9Hz, 1H), 7.15 (d, J = 7.3Hz, 1H), 6.92 (s , 1H), 6.80 (d, J = 7.9Hz, 1H), 6.14 (s, 1H), 2.87 (s, 3H), 1.48 (s, 3H), 1.32 (s, 3H), 1.31 (s, 3H), 1.27 (s, 3H) MS (MALDI-TOF): m / z calcd for C 61 H 42 BNO2S2 895.275; found 895.265 ([M] + ​).

[0214] (4) Synthesis of Exemplary Compound 4 (Compound 13 of Chemical Formula 11)

[0215] (4-1) 9-(3,5-difluorophenyl)-3,6-diphenyl-9H-carbazole (D-1) Under a nitrogen atmosphere, 1-bromo-3,5-difluorobenzene (10.1 g, 52.3 mmol), 3,6-diphenylcarbazole (13.4 g, 41.9 mmol), sodium tert-butoxide (14.5 g, 150 mmol), 2-Di-tert-butylphosphono-2′, 4',6'-triisopropylbiphenyl (tBuXPhos, 1.56 g, 3.66 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 2.40 g, 2.62 mmol) were dissolved in toluene (300 mL) and stirred at 110°C for 11 hours. After cooling, the reaction mixture was added with dichloromethane and an aqueous ammonium chloride solution, and the organic phase was separated. The organic layer was dried over sodium sulfate, and the filtrate was evaporated under reduced pressure. The resulting residue was washed with methanol to give the target compound as a white solid (13.6 g, 31.5 mmol, 60%). GC-MS [431.1, M + , calcd. 431.1]

[0216] (4-2) 9-(3,5-difluoro-4-(triisopropylsilyl)phenyl)-3,6-diphenyl-9H-carbazole (D-2) Under a nitrogen atmosphere, D-1 (3.10 g, 7.18 mmol) was dissolved in dehydrated tetrahydrofuran (150 mL) and cooled to -78°C. A tetrahydrofuran / hexane solution of lithium diisopropylamide (1 mol / L, 10.2 mL) was added dropwise to the reaction solution, and the mixture was stirred for 1.5 hours. Thereafter, triisopropylsilyl chloride (1.66 g, 8.62 mmol) was added dropwise, and the mixture was stirred at room temperature for 15 hours. A saturated ammonium chloride solution was added to the reaction mixture, which was then extracted with dichloromethane, and the organic phase was recovered. The organic phase was dried over anhydrous magnesium sulfate, and the filtrate was evaporated under reduced pressure. The resulting residue was dissolved in chloroform and added dropwise to methanol, resulting in the precipitation of a white powder. The suspension was filtered to recover the target compound as a white powder (3.60 g, 6.12 mmol, 85%). GC-MS [587.2, M + , calcd. 587.2]

[0217] (4-3) 9-(3,5-difluoro-2-iodo-4-(triisopropylsilyl)phenyl)-3,6-diphenyl-9H-carbazole (D-3) Under a nitrogen atmosphere, D-2 (1.51 g, 2.55 mmol) was dissolved in dehydrated tetrahydrofuran (25 mL) and cooled to −78°C. A tetrahydrofuran / hexane solution of lithium diisopropylamide (1 mol / L, 3.1 mL) was added dropwise to the reaction solution, and the mixture was stirred at −78°C for 1.5 hours. Thereafter, a solution of iodine (777 mg) in tetrahydrofuran (5 mL) was added dropwise, and the mixture was stirred at −78°C for 1 hour and then at room temperature for 15 hours. A saturated aqueous solution of sodium thiosulfate was added to the reaction mixture, which was then extracted with dichloromethane, and the organic phase was recovered. The organic phase was dried over anhydrous magnesium sulfate, and the filtrate was evaporated under reduced pressure. The resulting residue was washed with methanol, and the target compound was recovered as a white powder (1.58 g, 2.21 mmol, 87%). GC-MS [713.1, M + , calcd. 713.1]

[0218] (4-4) 9-(3,5-difluoro-2-iodophenyl)-3,6-diphenyl-9H-carbazole (D-4) Under a nitrogen atmosphere, D-3 (1.50 g, 2.10 mmol) was dissolved in dehydrated tetrahydrofuran (18 mL). A solution of tetrabutylammonium fluoride in tetrahydrofuran (1 mol / L, 4.2 mL) was added dropwise to the mixture at room temperature, and the mixture was stirred for 1 hour. A saturated aqueous solution of ammonium chloride was added to the reaction mixture, which was then extracted with dichloromethane, and the organic phase was recovered. The organic phase was dried over anhydrous magnesium sulfate, and the filtrate was evaporated under reduced pressure. The resulting residue was washed with methanol, and the target compound was recovered as a white powder (860 mg, 1.54 mmol, 73%). GC-MS [557.0, M + , calcd. 557.0]

[0219] (4-5) 9-(3,5-bis(dibenzo[b,d]thiophen-1-yloxy)-2-iodophenyl)-3,6-diphenyl-9H-carbazole (D-5) D-4 (201 mg, 0.361 mmol), dibenzothiophen-1-ol (181 mg, 0.902 mmol), potassium carbonate (250 mg, 1.80 mmol), and dimethylformamide (6 mL) were mixed under a nitrogen atmosphere and stirred at 120°C for 11 hours. After cooling, a saturated aqueous solution of sodium chloride was added to the reaction mixture, which was then extracted with chloroform, and the organic phase was recovered. The organic phase was dried over anhydrous magnesium sulfate, and the filtrate was evaporated under reduced pressure. The resulting residue was purified by column chromatography (hexane / ethyl acetate) to recover the target compound as a white powder (320 mg, 0.35 mmol, 97%).

[0220] 1 ​H NMR (500MHz, CDCl3) δ (ppm): 6.90 (d, J = 2.5Hz, 1H), 6.98-7.05 (m , 3H), 7.19 (d, J = 8.5Hz, 2H), 7.29-7.54 (m, 12H), 7.58 (d, J = 7.0Hz , 1H), 7.64-7.77 (m, 7H), 7.83 (d, J = 8.0Hz, 1H), 7.86-7.95 (m, 1H), 8.31 (d, J = 7.5Hz, 1H), 8.38 (d, J = 9.0Hz, 2H), 8.60-8.66 (m, 1H)

[0221] (4-6) Exemplary Compound 4 Under a nitrogen atmosphere, D-5 (100 mg, 0.11 mmol) and toluene (4.0 mL) were mixed and cooled to −50°C in a dry ice / methanol / water bath. A tetrahydrofuran solution of isopropyl magnesium chloride-lithium chloride complex (1 mol / L, 0.13 mL) was added dropwise thereto, and the mixture was stirred at −50°C. After 30 minutes, boron tribromide (0.1 mL) was added dropwise thereto, and the mixture was stirred at room temperature for 2 hours. Then, diisopropylethylamine (1.0 mL) was added dropwise at 0°C, and the mixture was stirred at 110°C for 3 hours. The suspension of the reaction mixture was filtered, washed with acetonitrile and toluene, and then dissolved in dichloromethane and subjected to silica column chromatography. The resulting solution was concentrated and washed with toluene to recover a crude product. The crude product was purified by sublimation, and the target compound was recovered as a yellow powder (31 mg, 0.039 mmol, 36%).

[0222] 1 H NMR (500MHz, CDCl3) δ (ppm): 7.33-7.65 (m, 13H), 7.71-7.81 (m, 3H), 7.84-7.98 (m, 6H), 8.04-8 .12 (m, 2H), 8.48 (d, J = 1.8Hz, 1H), 8.64-8.70 (m, 2H), 8.91 (d, J = 8.2Hz, 1H), 9.06 (d, J = 7.1Hz, 1H), 9.13 (d, J=1.7Hz, 1H)

[0223] Example 2 (Measurement of PLQY) Exemplary Compounds 1 to 3 and Comparative Compound 1 were analyzed using toluene (10 -5 ​PLQY measurements were performed on the M) solution. The absolute PL quantum yields were measured using an integrating sphere system ILF-835 (Jasco). Table 2 shows the PLQY of Comparative Compound 1 as 100. The oscillator strengths shown in Table 1 are also shown.

[0224]

[0225] As can be seen from Table 2, exemplary compounds 1 to 3, which are organic compounds according to the present disclosure, exhibited higher PLQY than comparative compound 1. Exemplary compounds 1 to 3 also had higher oscillator strengths than comparative compound 1. Therefore, organic light-emitting devices using the organic compounds according to the present disclosure can be expected to have excellent luminous efficiency.

[0226] The invention is not limited to the above-described embodiments, and various changes and modifications can be made without departing from the spirit and scope of the invention. Accordingly, the following claims are appended to apprise the public of the scope of the invention.

[0227] This application claims priority based on Japanese Patent Application No. 2024-131759 filed on August 8, 2024, and Japanese Patent Application No. 2025-021009 filed on February 12, 2025, the entire contents of which are incorporated herein by reference.

[0228] 1: Interlayer insulating layer, 2: First electrode, 3: Insulating layer, 4: Organic compound layer, 5: Second 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: TFT, 19: Insulating film, 20: Contact hole, 21: Anode, 22: Organic compound layer, 23: Cathode, 24: First protective layer, 25: Second protective layer, 26: Organic light-emitting element, 100: Display device

Claims

An organic compound represented by the following general formula (1): In general formula (1), ring a and ring b are each independently selected from a substituted or unsubstituted aryl ring and a substituted or unsubstituted heteroaryl ring. The ring a and the ring b may be bonded to each other. R1 to R3 are each independently selected from 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 heteroaryl 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, with the proviso that at least one of R1 to R3 is each independently selected from a group represented by the following general formula (2): R4 to R7 are each independently selected from 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 heteroaryl 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 two adjacent groups from one pair of R4 to R7 are bonded to form a c-ring, and the c-ring is a substituted or unsubstituted heteroaryl ring in which a five-membered ring and a six-membered ring are fused. X1 is an oxygen atom or a sulfur atom. In general formula (2), the d rings are each independently selected from a substituted or unsubstituted aryl ring and a substituted or unsubstituted heteroaryl ring in which a five-membered ring and a six-membered ring are fused. X2 is independently selected from an oxygen atom and a sulfur atom. * indicates the bonding position with general formula (1). Substituents that the rings a to d may have are each independently selected from a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl 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.

2. The organic compound according to claim 1, represented by the following general formula (3): In general formula (3), two adjacent groups of R4 to R7 in one group are bonded to a group represented by the following general formula (4). R8 to R 16 are each independently selected from 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 heteroaryl 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. In general formula (4), R 17 ~R 20 are each independently selected from 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 heteroaryl 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. Y1 is an oxygen atom, a sulfur atom, a selenium atom, or a tellurium atom. * indicates the bonding position with general formula (3).

3. The organic compound according to claim 1, wherein the d ring is a ring represented by the following general formula (5) or (6): In general formula (5), R 21 To R 28 are each independently selected from 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 heteroaryl 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. 21 ~R 28 One of them is bonded to X2. Y2 is an oxygen atom, a sulfur atom, a selenium atom, or a tellurium atom. In general formula (6), R 29 To R 33 are each independently selected from 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 heteroaryl 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. * indicates the bonding position to X2.

4. The organic compound according to claim 1, wherein at least one of the substituents which the ring a to ring d may have, the R to R, and the R to R may have is selected from a substituted or unsubstituted alkyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having from 6 to 18 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, and a cyano group. 　 The organic compound according to claim 4, characterized in that at least one of the substituents which the rings a to d may have, the R1 to R7, and the substituents which the R1 to R7 may have is selected from the following Group A. The organic compound according to claim 5, wherein the substituents which the rings a to d may have, the R1 to R7, and the R1 to R7 may have are all selected from the group A.

7. The organic compound according to claim 1, wherein R2 of the R1 to R3 is a group represented by the general formula (2).

8. The organic compound according to claim 1, wherein the ring c is a benzofuran ring, a benzothiophene ring, or a benzotellurophene ring.

9. The organic compound according to claim 1, wherein the substituents that the ring a to ring d may have are each independently selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted phenoxy group. 　 The R8 to R 11 The organic compound according to claim 2, wherein two adjacent groups in one pair are bonded to the group represented by the general formula (4). 　 The organic compound according to any one of claims 1 to 10, wherein R6 and R7 are bonded to form a c-ring.

12. The organic compound according to claim 1, wherein R to R and R to R are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. 　 The R8 to R 16 , R 17 ~R 20 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. 　 The R 21 ~R 28 , R 29 ~R 33 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. 　 An organic light-emitting device having a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, An organic light-emitting device, wherein at least one of the organic compound layers contains the organic compound according to claim 1 . 　 The organic light-emitting device according to claim 15, wherein the layer containing the organic compound is a light-emitting layer. 　 the light-emitting layer further comprises a first compound; 17. The organic light-emitting device according to claim 16, wherein the lowest excited singlet energy of the first compound is higher than the lowest excited singlet energy of the organic compound. 　 the light-emitting layer further comprises a second compound; 18. The organic light-emitting element according to claim 17, wherein the lowest excited singlet energy of the second compound is higher than the lowest excited singlet energy of the organic compound and lower than the lowest excited singlet energy of the first compound. 　 An ink composition comprising the organic compound according to claim 1 .

19. A display device comprising a plurality of pixels, at least one of the plurality of pixels comprising the organic light-emitting element according to claim 15 and a transistor connected to the organic light-emitting element. 　 an optical unit having a plurality of lenses, an image pickup element that receives light that has passed through the optical unit, and a display unit that displays an image picked up by the image pickup element; The photoelectric conversion device, wherein the display section comprises the organic light-emitting element according to claim 15 .

19. An image display device comprising: a display unit having the organic light-emitting element according to claim 15; and a housing in which the display unit is provided.

19. An electronic device comprising: a display unit having the organic light-emitting element according to claim 15; a housing in which the display unit is provided; and a communication unit provided in the housing and communicating with an external device.

19. A wearable device comprising: a display unit having the organic light-emitting element according to claim 15; an optical system that collects light from the display unit; and a control device that controls display of the display unit.

19. A lighting device comprising: a light source having the organic light-emitting element according to claim 15; and a light diffusion section or an optical film that transmits light emitted from the light source. 　 A moving body comprising: a lamp having the organic light-emitting element according to any one of claims 15 to 18; and a body on which the lamp is provided. 　 An exposure light source for an electrophotographic image forming apparatus, comprising the organic light-emitting element according to claim 15 .

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