Organic compound and organic light-emitting element

Abstract

An organic compound characterized by being represented by any one of general formulae G1-G6. In general formulae G1-G6, R12 to R18, R22 to R28, R31, R32, R111 to R114, R211 to R214 are each a hydrogen atom or any substituent. However, at least one of R31 and R32 is other than a hydrogen atom and a deuterium atom, and at least one of R12 to R18, R22 to R28, R111 to R114, and R211 to R214 is other than a hydrogen atom. X1 and X2 are each independently selected from the group consisting of an oxygen atom, a sulfur atom, a tellurium atom, and a selenium atom.

Description

Organic Compound and Organic Light-Emitting Device

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

[0002] An organic light-emitting device (hereinafter sometimes referred to as an "organic electroluminescence device" or an "organic EL device") is an electronic device having a pair of electrodes and an organic compound layer disposed between these electrodes. By injecting electrons and holes from these 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.

[0003] By the way, creation of compounds suitable for organic light-emitting devices has been actively carried out up to now. In Patent Document 1, BD-C1 to BD-C2 are described as compounds having an indolocarbazole skeleton.

[0004]

[0005] International Publication No. 2020 / 067290

[0006] However, since the organic compound described in Patent Document 1 is a compound that easily aggregates, there is room for improvement in luminous efficiency.

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

[0008] The organic compound according to the present invention is characterized by being represented by general formulas G1 to G6.

[0009]

[0010] In general formulas G1 to G6, R １２ to R １８ , R ２２ to R ２８ , R ３１ , R ３２ , R １１１ to R １１４ , R ２１１ to R ２１４Each of the following groups is independently selected from the group consisting of hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted thioalkoxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted thioaryl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted thioheteroaryl groups, substituted or unsubstituted heteroaryloxy groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amino groups, cyano groups, and nitro groups. However, R ３１ and R ３２ At least one of them is a non-hydrogen atom, R １２ ~R １８ , R ２２ ~R ２８ , R １１１ ~R １１４ , R ２１１ ~R ２１４ At least one of them is not a hydrogen atom. １ and X ２ Each of these atoms is independently selected from the group consisting of oxygen atoms, sulfur atoms, tellurium atoms, and selenium atoms.

[0011] According to the present invention, it is possible to provide an organic compound with excellent luminescence efficiency.

[0012] This is a schematic cross-sectional view showing an example of a pixel in a display device according to one embodiment of the present invention. This is a schematic cross-sectional view showing an example of a display device using an organic EL element according to one embodiment of the present invention. This is a schematic diagram showing an example of a display device according to one embodiment of the present invention. This is a schematic diagram showing an example of an imaging device according to one embodiment of the present invention. This is a schematic diagram showing an example of an electronic device according to one embodiment of the present invention. This is a schematic diagram showing an example of a display device according to one embodiment of the present invention. This is a schematic diagram showing an example of a foldable display device. This is a schematic diagram showing an example of a lighting device according to one embodiment of the present invention. This is a schematic diagram showing an example of an automobile having vehicle lighting fixtures according to one embodiment of the present invention. This is a schematic diagram showing an example of an automobile having vehicle lighting fixtures and a display unit according to one embodiment of the present invention. This is a schematic diagram showing an example of a wearable device according to one embodiment of the present invention. This is a schematic diagram showing an example of a wearable device having an imaging device according to one embodiment of the present invention. This is a schematic diagram showing an example of an image forming apparatus according to one embodiment of the present invention. This is a schematic diagram showing an example of an exposure light source for an image forming apparatus according to one embodiment of the present invention. This is a schematic diagram showing an example of an exposure light source for an image forming apparatus according to one embodiment of the present invention. This is the normalized emission spectrum of compound BD-1 in a toluene solution. This is the normalized emission spectrum of compound BD-C1 in a toluene solution. This is the normalized emission spectrum of compound BD-C2 in a toluene solution. The diagram shows the structures of compounds BD-1, BD-C1, and BD-C2 viewed from the horizontal.

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

[0014] The alkyl group may be an alkyl group having 1 to 50 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or an alkyl group having 1 to 4 carbon atoms. Specifically, examples include, but are not limited to, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, secondary butyl group, octyl group, cyclohexyl group, tert-pentyl group, 3-methylpentan-3-yl group, 1-adamantyl group, and 2-adamantyl group.

[0015] The alkenyl group may be either an E-alkenyl group or a Z-alkenyl group. The E-alkenyl group and the Z-alkenyl group may have 1 to 20 carbon atoms, 1 to 10 carbon atoms, or 1 to 8 carbon atoms.

[0016] The alkynyl group may be an alkynyl group having 1 to 20 carbon atoms, an alkynyl group having 1 to 10 carbon atoms, or an alkynyl group having 1 to 8 carbon atoms.

[0017] The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. Specifically, examples include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, a 2-ethyl-octyloxy group, a benzyloxy group, etc.

[0018] A thioalkoxy group is a structure in which the oxygen atom that would normally substitute for an alkyl group in an alkoxy group is replaced by a sulfur atom. A thioalkoxy group may have 1 to 20 carbon atoms, 1 to 10 carbon atoms, or 1 to 4 carbon atoms. Specifically, examples include, but are not limited to, thiomethoxy, thioethoxy, thiopropoxy, 2-ethyl-octylthio, and benzylthio groups.

[0019] The aryl group may be an aryl group having 6 to 50 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aryl group having 6 to 18 carbon atoms, or an aryl group having 6 to 12 carbon atoms. Specifically, examples include, but are not limited to, phenyl, naphthyl, indenyl, biphenyl, terphenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, anthranyl, perilenyl, chrysenyl, and fluoranthenyl groups.

[0020] A thioaryl group is a structure in which the oxygen atom bonded to the aryl group in an aryloxy group is replaced by a sulfur atom. Examples include, but are not limited to, the thiophenoxy group.

[0021] Examples of aryloxy groups include, but are not limited to, phenoxy groups.

[0022] The heteroaryl group may be a heteroaryl group having 3 to 50 carbon atoms, a heteroaryl group having 5 to 50 carbon atoms, a heteroaryl group having 3 to 24 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a heteroaryl group having 5 to 18 carbon atoms, or a heteroaryl group having 5 to 12 carbon atoms. Specifically, examples include, but are not limited to, pyridyl, pyrimidyl, pyrazyl, triazyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, carbazolyl, acridinyl, and phenanthrolyl groups.

[0023] A thioheteroaryl group is a heteroaryloxy group in which the oxygen atom bonded to the heteroaryl group is replaced by a sulfur atom. Examples include, but are not limited to, the thienylthio group.

[0024] Examples of heteroaryloxy groups include, but are not limited to, thienyloxy groups.

[0025] Examples of silyl groups include, but are not limited to, trimethylsilyl and triphenylsilyl groups.

[0026] The amino group may be a substituted amino group substituted with an alkyl group or an aryl group, and may be a substituted amino group substituted with an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 12 carbon atoms. Specifically, examples include, but are not limited to, N-methylamino group, N-ethylamino group, N,N-dimethylamino group, N,N-diethylamino group, N-methyl-N-ethylamino group, N-benzylamino group, N-methyl-N-benzylamino group, N,N-dibenzyloamino group, anilino group, N,N-diphenylamino group, N,N-dinaphthylamino group, N,N-difluorenylamino group, N-phenyl-N-tolylamino group, N,N-ditolylamino group, N-methyl-N-phenylamino group, N,N-dianisorylamino group, N-mesityl-N-phenylamino group, N,N-dimesitylamino group, N-phenyl-N-(4-tert-butylphenyl)amino group, N-phenyl-N-(4-trifluoromethylphenyl)amino group, N-piperidyl group, etc.

[0027] The alkyl, alkenyl, alkynyl, alkoxy, thioalkoxy, aryl, thioaryl, aryloxy, heteroaryl, thioheteroaryl, heteroaryloxy, silyl, and amino groups may further contain substituents such as halogen atoms (fluorine, chlorine, bromine, iodine), alkyl groups (methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl), alkoxy groups (methoxy, ethoxy, propoxy), amino groups (dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditrilylamino), aryloxy groups (phenoxy), aryl groups (phenyl, biphenyl), heteroaryl groups (pyridyl, pyrrolyl), and cyano groups, but are not limited to these.

[0028] Furthermore, in this specification, the basic structure refers to the R of general formulas G1 to G6. １２ ~R １８ , R ２２ ~R ２８ , R ３１ , R ３２ , R １１１ ~R １１４ , R ２１１ ~R ２１４ This refers to the skeleton, which consists of hydrogen atoms.

[0029] (1) Organic Compounds First, the organic compounds according to the present invention will be described.

[0030] The organic compound according to the present invention is a compound represented by general formula G1 to G6. The organic compound according to this embodiment is preferably a compound represented by general formula G1 or G2, and more preferably a compound represented by general formula G1.

[0031] <R １２ ~R １８ , R ２２ ~R ２８ , R １１１ ~R １１４ , R ２１１ ~R ２１４ > In general formulas G1 to G6, R １２ ~R １８, R ２２ ~R ２８ , R １１１ ~R １１４ , R ２１１ ~R ２１４ Each of these is independently selected from the group consisting of hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted thioalkoxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted thioaryl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted thioheteroaryl groups, substituted or unsubstituted heteroaryloxy groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amino groups, cyano groups, and nitro groups.

[0032] The organic compound according to the present invention is R １２ ~R １８ , R ２２ ~R ２８ , R １１１ ~R １１４ , R ２１１ ~R ２１４ At least one of the substituents is a hydrogen atom. The organic compound according to this embodiment is R １３ and R ２３ , R １４ and R ２４ , R １５ and R ２５ , R １７ and R ２７ , R １８ and R ２８ , R １１１ and R ２１１ , R ２１２ and R ２１２ , R １１３ and R ２１３ , R １１４ and R ２１４ It is preferable that at least one set of substituents other than hydrogen atoms. Furthermore, the organic compound according to this embodiment is R １３ and R ２３ , R １４ and R ２４ , R １７ and R ２７ , R １８ and R２８ , R １１１ and R ２１１ , R ２１２ and R ２１２ , R １１３ and R ２１３ , R １１４ and R ２１４ It is more preferable that at least one pair of them is a substituent other than a hydrogen atom. Further, in the organic compound according to the present embodiment, R １４ and R ２４ , R １１１ and R ２１１ It is more preferable that at least one pair of them is a substituent other than a hydrogen atom. Particularly, in the organic compound according to the present embodiment, it is particularly preferable that R １４ and R ２４ are substituents other than a hydrogen atom. Among the above combinations, for example, when R １３ and R ２３ are substituents other than a hydrogen atom, R １３ and R ２３ may be the same or different, but it is preferable that they are the same from the viewpoint of synthesis. The same applies to other combinations.

[0033] In the organic compound according to this embodiment, the substituent is preferably independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted thioalkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted thioaryl group having 6 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted thioheteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 3 to 50 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a cyano group, and a nitro group. Furthermore, in the organic compound according to this embodiment, it is even more preferable that the substituent is an alkyl group having 3 to 5 carbon atoms, a substituted or unsubstituted aryl group having 6 to 16 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. Furthermore, in the organic compound according to this embodiment, it is even more preferable that the substituent is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 12 carbon atoms, or an alkyl group having 3 to 5 carbon atoms. Furthermore, in the organic compound according to this embodiment, it is particularly preferable that the substituent is an aryl group having 6 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms and an alkyl group having 1 to 4 carbon atoms, a heteroaryl group having 6 to 12 carbon atoms, or an alkyl group having 3 to 5 carbon atoms. In this case, the alkyl group having 1 to 4 carbon atoms may be a methyl group, an iso-propyl group, or a tert-butyl group.

[0034] <R ３１ and R ３２ > In general formulas G1 to G6, R ３１ and R ３２Each of these is independently selected from the group consisting of hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted thioalkoxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted thioaryl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted thioheteroaryl groups, substituted or unsubstituted heteroaryloxy groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amino groups, cyano groups, and nitro groups.

[0035] The organic compound according to the present invention is R ３１ and R ３２ At least one of them is a substituent other than a hydrogen atom. The organic compound according to this embodiment is R ３１ and R ３２ It is preferable that R is an atom other than a hydrogen atom. ３１ and R ３２ When R is a substituent other than a hydrogen atom, ３１ and R ３２ They may be the same or different, but from a compositional standpoint, it is preferable that they be the same.

[0036] In the organic compound according to this embodiment, the substituent is preferably independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted thioalkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted thioaryl group having 6 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted thioheteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 3 to 50 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a cyano group, and a nitro group. Furthermore, in the organic compound according to this embodiment, it is even more preferable that the substituent is an alkyl group having 3 to 5 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, or an amino group having 6 to 10 carbon atoms. Furthermore, in the organic compound according to this embodiment, it is even more preferable that the substituent is an alkyl group having 3 to 5 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or an amino group having 6 to 10 carbon atoms. Furthermore, in the organic compound according to this embodiment, it is even more preferable that the substituent is an iso-propyl group, a tert-butyl group, or C(C) ２ H ５ ) ２ Particularly preferred are a phenyl group, a phenyl group having an alkyl group with 1 to 4 carbon atoms, a phenyl group having a cyano group, a biphenyl group, or an amino group having a phenyl group. In this case, the alkyl group having 1 to 4 carbon atoms may be a methyl group, an iso-propyl group, or a tert-butyl group.

[0037] < X １ and X ２> In general formulas G1 to G6, X １ and X ２ Each of these atoms is independently selected from the group consisting of oxygen atoms, sulfur atoms, tellurium atoms, and selenium atoms. The organic compound according to this embodiment is X １ and X ２ Preferably, each of these is an oxygen atom or a sulfur atom. Furthermore, the organic compound according to this embodiment is X １ and X ２ They may be the same or different, but from a compositional standpoint, it is preferable that they be the same.

[0038] The present invention will be described in detail below.

[0039] The organic compound according to the present invention is R ３１ and R ３２ At least one of them has a substituent other than a hydrogen atom, and R １２ ~R １８ , R ２２ ~R ２８ , R １１１ ~R １１４ , R ２１１ ~R ２１４ The presence of at least one substituent other than a hydrogen atom results in superior luminescence efficiency.

[0040] Figure 11 shows the horizontal structures of compound BD-1, an organic compound according to the present invention, and comparative examples, compounds BD-C1 and BD-C2. As shown in Figure 11, the basic skeleton of the organic compound according to the present invention has a highly planar structure as a whole because the planarity is high near the benzene ring located in the center of the basic skeleton and near the benzophlo structure at the end of the skeleton. Compound BD-C1 has an iso-propyl group in the central benzene ring, so the planarity is low near the benzene ring. However, because the planarity is high near the benzophlo structure at the end of the skeleton, the compound is prone to aggregation. Similarly, compound BD-C2 has a phenyl group substituted near the benzophlo structure at the end of the skeleton, so the planarity is low near the benzophlo structure. However, because the planarity is high near the benzene ring located in the center of the basic skeleton, the compound is prone to aggregation, similar to compound BD-C1.

[0041] On the other hand, the organic compounds according to the present invention have a structure in which the benzene atom located at the center of the basic skeleton has substituents other than hydrogen atoms, and substituents are also present in parts other than the benzene atom. In particular, as seen in compound BD-1 in Figure 11, the benzene and benzophlo structure located at the center of the basic skeleton, which has particularly high molecular planarity, are covered by substituents. Therefore, compared to compounds BD-C1 and BD-C2, the organic compounds according to the present invention have lower overall molecular planarity and are less prone to aggregation of compounds.

[0042] Here, we will explain the effects of organic compounds being less prone to aggregation.

[0043] Films using organic compounds that are less prone to aggregation are less likely to crystallize, resulting in a more uniform film quality. Specifically, partial crystallization within the film is less likely to occur. When organic compounds are less prone to aggregation, the formation of grain boundaries, trap levels, and quenchers associated with minute crystallization is less likely, and energy transfer from the host material to the guest material becomes easier. Furthermore, when the organic compounds according to this embodiment are used as the guest material, a light-emitting layer in which the guest materials are dispersed can be formed. As a result, concentration quenching due to aggregation of guest materials can be reduced, making it possible to provide an organic light-emitting element with excellent luminescence efficiency.

[0044] Therefore, the organic compounds according to the present invention can reduce aggregation between compounds, thus providing organic compounds with excellent luminescence efficiency.

[0045] Next, in order to quantitatively confirm the effect of the organic compounds according to this embodiment, the cohesive energy density of each compound was calculated. Cohesive energy density is a known parameter that indicates how easily organic compounds cohesive. A higher cohesive energy density indicates that organic compounds cohesive easily with each other, while a lower value indicates that organic compounds do not cohesive easily with each other. In this embodiment, the cohesive energy density was 35 kcal mol. －１ nm －３ It may be less than 30 kcal mol －１ nm －３ The following may be used: 27 kcal mol －１ nm－３ The following may be used: 25 kcal mol －１ nm －３ The following is acceptable:

[0046] The cohesive energy density was calculated using the following equation (1): Cohesive energy density = Cohesive energy / Molecular volume ... Equation (1)

[0047] The cohesive energy was calculated using the Potential of Mean Force (PMF) obtained by molecular dynamics. GROMACS can be used as the molecular dynamics software.

[0048] When performing calculations using molecular dynamics, parameters defining the interactions between atoms are set in advance. For setting these parameters, GAFF (General Amber Force Field), commonly used in calculations of organic molecules, was employed. The charge assigned to each atom was determined using quantum chemical calculations. In this specification, structural optimization calculations were performed using the B3LYP functional and basis set 6-31G*, and the most stable structure was fitted with MK (Merz-Kollmann-Singh) charges. Quantum chemical calculation software used included, for example, Gaussian 16 and Revision C. 01 (Gaussian 16, Revision C.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone、G. A. Petersson、H. Nakatsuji、X. Li, M. Caricato、A. V. Marenich、J. Bloino、B. G. Janesko、R. Gomperts, B. Mennucci, H.P. A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery,Jr. , J. E. Peralta, F. Ogliaro, M. J. Bearpark, J. J. Heyd, E. N. Brothers, K. N. Kudin, V. N. Staroverov, T. A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. P. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2019. The MK charge fitting is described in B. H. Besler, et al., J. Comp. Chem. 11, 431 (1990) and U. C. Singh, et al., J. Comp. Chem. 5, 129 (1984).

[0049] PMF is calculated using the umbrella sampling method. First, equilibrium and production calculations are performed under isothermal and isobaric conditions for multiple prepared windows. Then, the WHAM (Weighted Histogram Analysis Method) is used to analyze and obtain the PMF potential curve. In addition, since the degrees of freedom of molecules differ at each intermolecular distance, an entropy correction term 2kTln(r) is added. Here, k is the Boltzmann constant, T is the absolute temperature, r is the distance between two molecules, and ln is the natural logarithm. Using the corrected PMF, the cohesive energy is calculated from the difference between the maximum and minimum energies. The calculation method for PMF is described in J. S. Hub, et al., J Chem Theory Comput 6.12.3713-3720 (2010). In this calculation, for the sake of accuracy, the window step was set to 0.05 nm, and the cohesive energy was the average of the results from 10 calculations.

[0050] The molecular volume is calculated using quantum chemical calculations, and the Cavity volume used is utilized when calculating the SMD model of the SCRF (Self-consistent reaction field) method. The SMD model is described in A. V. Marenich, et al. J. Phys. Chem. B, 113.18. 6378-6396 (2009).

[0051] Table 1 shows the cohesive energy densities of compounds BD-1 to BD-41, which are organic compounds according to this embodiment, and compounds BD-C1 and BD-C2, which are comparative examples. The PMF values ​​in the table are in units of kcal mol. －１ nm －３ This is an abbreviation of ).

[0052]

[0053]

[0054]

[0055] Table 1 shows that the PMF of compound BD-1, an organic compound according to the present invention, is 27 kcal mol. －１ nm －３ In contrast, the PMF of the comparative compounds BD-C1 and BD-C2 was 41 kcal mol each. －１ nm －３ and 39 kcal mol －１ nm －３ Therefore, compared to the comparative examples compounds BD-C1 and BD-C2, compound BD-1, the organic compound according to the present invention, is less prone to aggregation and is therefore found to be an organic compound with excellent luminescence efficiency.

[0056] Furthermore, the PMF of BD-1 is 27 kcal mol. －１ nm －３ In contrast, the PMF of BD-6 is 33 kcal mol. －１ nm －３ That was the case. BD-6 is R ３２ While is a hydrogen atom, BD-1 is R ３２It differs in that it is an iso-propyl group. Since the PMF of BD-1 was lower than that of BD-6, R ３１ and R ３２ R is preferably a substituent other than a hydrogen atom. ３１ and R ３２ This is thought to be because the substituents other than hydrogen atoms result in a lower planarity of benzene, which is located at the center of the basic skeleton.

[0057] Furthermore, the organic compound according to this embodiment is R ３１ and R ３２ Compared to compounds in which R is an aryl group, ３１ and R ３２ Compounds in which the parent molecule is an alkyl group tended to show low PMF. In particular, R ３１ and R ３２ It is preferable that has a branched alkyl group such as an iso-propyl group or a tert-butyl group, R ３１ and R ３２ It is even more preferable that the group is a branched alkyl group such as an iso-propyl group or a tert-butyl group.

[0058] Furthermore, the PMF of BD-1 is 27 kcal mol. －１ nm －３ In contrast, the PMF of BD-4 is 31 kcal mol. －１ nm －３ That was the case. BD-4 is R １１２ and R ２１２ While is a phenyl group, BD-1 is R １４ and R ２４ It differs in that it is a phenyl group. Since the PMF of BD-1 was lower than that of BD-4, R １４ and R ２４ It is preferable that the molecule has substituents. １４ and R ２４ This is thought to be because the presence of substituents reduces the planarity of the benzofluo structure.

[0059] Furthermore, the PMF of BD-1 is 27 kcal mol. －１ nm －３ In contrast, the PMF of BD-2 is 34 kcal mol.－１ nm －３ That was the case. BD-2 is R １４ and R ２４ While is a tert-butyl group, BD-1 is R １４ and R ２４ It differs in that it is a phenyl group. Since the PMF of BD-1 was lower than that of BD-2, R １４ and R ２４ It is preferable that the group is an aryl group or a heteroaryl group.

[0060] Specific examples of organic compounds according to the present invention are shown below. However, the present invention is not limited to these.

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068] (2) Organic Light-Emitting Device Next, an organic light-emitting device according to one embodiment of the present invention will be described. The organic light-emitting device according to one embodiment of the present invention has a first electrode, a second electrode, and an organic compound layer disposed between these electrodes. One of the first electrode and the second electrode is an anode and the other is a cathode. In the organic light-emitting device according to this embodiment, the organic compound layer may be a single layer or a laminate consisting of multiple layers, provided that it has a light-emitting layer. The organic compound according to the present invention may be contained in the organic compound layer, and preferably it is contained in the light-emitting layer. Here, if the organic compound layer is a laminate consisting of multiple layers, the organic compound layer may have a hole injection layer, a hole transport layer, an electron blocking layer, a hole-exciton blocking layer, an electron transport layer, an electron injection layer, etc., in addition to the light-emitting layer. The light-emitting layer may be a single layer or a laminate consisting of multiple layers. If there are multiple light-emitting layers, a charge generation layer may be provided between the light-emitting layers. The charge generation layer may be composed of a compound whose LUMO (Lowest Unoccupied Molecular Orbital) energy level is lower than that of the hole transport layer, and the LUMO energy level of the charge generation layer may be lower than that of the HOMO energy level of the hole transport layer. Here, the HOMO and LUMO energy levels of the organic compound layer may be those of the organic compound with the largest weight ratio in the organic compound layer.

[0069] Here, the HOMO energy level and LUMO energy level are described as "higher" the closer they are to the vacuum level. When the LUMO energy level of the charge generation layer is lower than the HOMO energy level of the hole transport layer, it means that the LUMO energy level of the charge generation layer is further from the vacuum level than the HOMO energy level of the hole transport layer.

[0070] In this specification, the HOMO energy levels and LUMO energy levels can be calculated using molecular orbital calculations. Molecular orbital calculations may be performed using density functional theory (DFT), with the functional being B3LYP and the basis set being 6-31G*, etc.The molecular orbital calculation can be carried out, for example, using Gaussian09 (Gaussian09, Revision C.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. 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. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gompertz, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2010.).

[0071] In this specification, the HOMO energy level and LUMO energy level can be calculated using the ionization potential and band gap. The HOMO energy level can be estimated by measuring the ionization potential. The ionization potential can be measured using a measuring device such as AC-3 after dissolving the compound to be measured in a solvent such as toluene or after creating a vapor-deposited film of the compound on a substrate such as glass. The band gap can be measured by dissolving the compound to be measured in a solvent such as toluene and irradiating it with excitation light. The band gap can be measured by measuring the absorption edge of the absorption spectrum of the excitation light. Alternatively, the compound to be measured can be vapor-deposited on a substrate such as glass and the vapor-deposited film can be irradiated with excitation light. The measurement can be performed by measuring the absorption edge of the absorption spectrum of the vapor-deposited film that absorbs the excitation light.

[0072] The LUMO energy level can be calculated using the band gap and ionization potential. By subtracting the ionization potential from the band gap, the LUMO energy level can be estimated.

[0073] The LUMO energy level can also be estimated from the reduction potential. For example, the one-electron reduction potential can be estimated using cyclic volmetry (CV) measurement. CV measurement is performed, for example, in a 0.1 M tetrabutylammonium perchlorate DMF solution, with an Ag / Ag reference electrode. ＋ The measurement can be performed using Pt as the counter electrode and glassy carbon as the working electrode. The LUMO energy level can be estimated by adding the difference between the reduction potential of the obtained compound and the reduction potential of ferrocene, which is -4.8 eV.

[0074] In an organic light-emitting element according to one embodiment of the present invention, if the organic compound according to the present invention is included in the light-emitting layer, the light-emitting layer may consist only of the organic compound according to the present invention, or it may consist of the organic compound according to the present invention and other compounds. Here, if the light-emitting layer is a layer consisting of the organic compound according to the present invention and other compounds, the organic compound according to the present invention may be used as a host material for the light-emitting layer, or as a guest material. It may also be used as an assist material that can be included in the light-emitting layer. Here, the host material is also called the "host" or "first compound," and is the compound with the largest mass ratio among the compounds constituting the light-emitting layer. The guest material is also called the "guest," "dopant material," "dopant," or "third compound," and is a compound with a smaller mass ratio than the host among the compounds constituting the light-emitting layer, and is the compound that is primarily responsible for light emission. For this reason, the guest material is sometimes also called the light-emitting material. The assist material is also called the "assist" or "second compound," and is a compound with a smaller mass ratio than the host material among the compounds constituting the light-emitting layer, and assists the light emission of the guest material. The assist material is also called the second host.

[0075] Here, let S1(H) be the lowest singlet excitation energy of the host material, S1(D) be the lowest singlet excitation energy of the guest material, and S1(A) be the lowest singlet excitation energy of the assist material. The guest material may be considered to be an organic compound according to the present invention. In this case, it is preferable that the organic light-emitting element according to this embodiment satisfies S1(H) > S1(D) or S1(H) > S1(A) > S1(D). By satisfying the above relationship between the lowest singlet excitation energy of the compound included in the organic light-emitting element according to this embodiment, excitons can be efficiently transferred to the guest material, resulting in an organic light-emitting element with superior luminescence efficiency.

[0076] When the organic compound according to the present invention is used as a guest material for the light-emitting layer, the concentration of the guest material may be 0.01% by mass or more and less than 50% by mass relative to the entire light-emitting layer, preferably 0.01% by mass or more and 10% by mass or less, and more preferably 0.01% by mass or more and 5% by mass or less.

[0077] When the light-emitting layer further comprises an assisting material, the assisting material may be 1% by mass or more and less than 50% by mass of the entire light-emitting layer, and is preferably 10% by mass or more and less than 50% by mass. The guest may be 0.01% by mass or more and 20% by mass or less, and is preferably 0.01% by mass or more and 5% by mass or less.

[0078] The inventors have conducted various studies and found that when the organic compound according to the present invention is used as a host material or guest material for the light-emitting layer, particularly as a guest material for the light-emitting layer, a device can be obtained that exhibits high efficiency, high brightness, and extremely high durability. This light-emitting layer may be a single layer or a multi-layer, and it is also possible to mix the light emission with the blue light emission of this embodiment by including a light-emitting material having another light emission color. A multi-layer means a state in which one light-emitting layer and another light-emitting layer are stacked. In this case, the light emission color of the organic light-emitting element is not limited to blue. More specifically, it may be white or an intermediate color. In the case of white, the other light-emitting layer emits a color other than blue, i.e., red or green. Furthermore, the film is formed by vapor deposition or coating. Details of this will be explained in detail in the examples described later.

[0079] The organic compound according to the present invention can be used as a constituent material for organic compound layers other than the light-emitting layer constituting the organic light-emitting device according to this embodiment. Specifically, it may be used as a constituent material for electron transport layers, electron injection layers, hole transport layers, hole injection layers, hole blocking layers, etc. In this case, the light-emitting color of the organic light-emitting device is not limited to blue. More specifically, it may be white light or an intermediate color.

[0080] (3) Other Compounds In addition to the organic compounds according to the present invention, conventionally known low-molecular-weight and high-molecular-weight hole-injection compounds or hole-transport compounds, host materials, luminescent compounds, electron-injection compounds or electron-transport compounds, etc., can be used together as needed. Examples of these compounds are listed below.

[0081] As hole-injection transport materials, materials with high hole mobility are preferred to facilitate hole injection from the anode and to transport the injected holes to the light-emitting layer. Furthermore, materials with a high glass transition temperature are preferred to suppress crystallization of organic compounds in the organic light-emitting element. Examples of low-molecular-weight and high-molecular-weight materials with hole-injection transport properties include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. In addition, the above-mentioned hole-injection transport materials are also suitably used in electron-blocking layers. Moreover, when the hole-injection layer is fabricated by a coating method, a mixture of polyethylenedioxythiophene and polystyrene sulfonic acid (PEDOT:PSS), which is commonly used as a hole-injection material, may be used. Specific examples of compounds used as hole-injection transport materials are shown below, but are not limited to these.

[0082]

[0083] Among the hole-injection transportable materials listed, HT16 to HT18 can reduce the driving voltage when used in the layer in contact with the anode. HT16 is widely used in organic light-emitting devices. HT2 to HT7, HT10, HT12, and HT22 to 28 may be used in the organic compound layer adjacent to HT16. Hole-transportable polymer compounds such as polyphenylene vinylene (PPV), polyfluorene (PF), polyvinylcarbazole (PVK), and their derivatives may also be used. In addition, inorganic insulating layers such as SiO2 and SiN, or organosilicon polymers such as siloxanes can also be used. Furthermore, multiple materials may be used in a single organic compound layer.

[0084] Guest materials primarily involved in luminescence include donor-acceptor type organic compounds, boron-containing complexes, indolocarbazole fused ring compounds, fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, organoaluminum complexes such as tris(8-quinolinolate)aluminum, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, poly(phenylenevinylene) derivatives, poly(fluorene) derivatives, poly(phenylene) derivatives, and other polymer derivatives. Furthermore, when creating a luminescent layer by coating, polymer compounds with luminescence properties are mainly used. This is because polymer compounds tend to exhibit high glass transition temperatures, making them less prone to crystallization compared to low-molecular-weight systems. Specific examples of materials used include polymer compounds such as polyphenylene vinylene (PPV), polyfluorene (PF), polyvinylcarbazole (PVK), and their derivatives.

[0085] The following are some specific examples of compounds used as luminescent materials, but of course, they are not the only ones.

[0086]

[0087]

[0088] The following are specific examples of compounds used as host or assist materials in the light-emitting layer, but of course, they are not the only ones that can be used.

[0089]

[0090] Among EM1 to EM47, the host material may be a hydrocarbon compound having a condensed polycyclic hydrocarbon group. Specifically, these are EM1 to EM26, EM46, and EM47.

[0091] As electron-transporting materials, any material capable of transporting electrons injected from the cathode to the light-emitting layer can be arbitrarily selected, taking into consideration the balance with the hole mobility of the hole-transporting material. Examples of materials with electron-transporting properties include oxadiazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organoaluminum complexes, and fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the above electron-transporting materials are also suitably used in the hole-blocking layer.

[0092] The following are specific examples of compounds used as electron transport materials, but of course, they are not the only ones.

[0093]

[0094] Electron-injectable materials can be arbitrarily selected from those that allow for easy electron injection from the cathode, taking into consideration the balance with hole injection properties. Organic compounds include n-type dopants and reducing dopants. Examples include alkali metal compounds such as lithium fluoride, lithium complexes such as lithium quinolinol, benzimidazolidene derivatives, imidazolidene derivatives, fluvalene derivatives, and acridine derivatives.

[0095] It can also be used in combination with the electron transport materials mentioned above.

[0096] Furthermore, the organic compounds according to the present invention can also be used as ink compositions.

[0097] The ink composition according to this embodiment contains at least one compound represented by general formulas G1 to G6. By using the ink composition according to this embodiment, it becomes possible to produce a layer made of organic compounds constituting an organic light-emitting element, particularly a light-emitting layer, by a coating method, making it possible to easily produce large-area elements at relatively low cost. Examples of solvents for dissolving the compounds represented by general formulas G1 to G6 include toluene, xylene, mesitylene, dioxane, methylnaphthalene, tetrahydrofuran, diglyme, 1,2-dichlorobenzene, and 1,2-dichloropropane. These solvents can be used alone or in combination of two or more. Among these, it is preferable to use a solvent with a suitable evaporation rate, specifically one with a boiling point of about 70 to 200°C, as it is easier to obtain a thin film with a uniform thickness. The ink composition according to this embodiment may also contain other additive compounds. Examples of additive compounds include the above-mentioned known light-emitting layer host or light-emitting assist material, hole transport material, light-emitting material, electron transport material, etc.

[0098] In the ink composition according to this embodiment, the concentration of the compound represented by general formulas G1 to G6 is preferably 0.05% by weight or more and 20% by weight or less, and more preferably 0.1% by weight or more and 5% by weight or less, relative to the entire composition.

[0099] The ink composition according to this embodiment can be formed into a film by methods such as spin coating, bar coating, slit coating, inkjet, nozzle coating, casting, or gravure printing to create the organic light-emitting element described later.

[0100] (4) Configuration of the Organic Light-Emitting Device The following describes the components that make up the organic light-emitting device of this embodiment.

[0101] An organic light-emitting element is provided on a substrate by forming an insulating layer, a first electrode, an organic compound layer, and a second electrode. A protective layer, a color filter, a microlens, etc., may be provided on the second electrode. If a color filter is provided, a planarization layer may be provided between it and the protective layer. The planarization layer can be made of acrylic resin or the like. The same applies when a planarization layer is provided between the color filter and the microlens.

[0102] [Substrate] Examples of substrates include quartz, glass, silicon wafers, resins, and metals. Switching elements such as transistors and wiring may be provided on the substrate, and an insulating layer may be provided on top of them. The insulating layer can be made of any material that allows for the formation of contact holes so that wiring can be formed between it and the first electrode, and that ensures insulation from wiring that is not connected. For example, resins such as polyimide, silicon oxide, and silicon nitride can be used.

[0103] [Electrodes] A pair of electrodes can be used. The pair of electrodes consists of a first electrode and a second electrode. Specifically, the pair of electrodes may be an anode and a cathode. When an electric field is applied in the direction in which the organic light-emitting element emits light, the electrode with the higher potential is the anode, and the other is the cathode. Alternatively, the electrode that supplies holes to the light-emitting layer may be the anode, and the electrode that supplies electrons may be the cathode.

[0104] The anode material should ideally have a high work function. For example, elemental metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten, or mixtures containing these, or alloys combining them, as well as metal oxides such as tin oxide, zinc oxide, indium oxide, tin-indium oxide (ITO), and zinc-indium oxide can be used. Conductive polymers such as polyaniline, polypyrrole, and polythiophene can also be used.

[0105] These electrode materials may be used individually or in combination of two or more types. Furthermore, the anode may consist of a single layer or multiple layers.

[0106] When used as a reflective electrode, materials such as chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys or laminates thereof can be used. These materials can also function as reflective films without serving as electrodes. Furthermore, when used as a transparent electrode, oxide transparent conductive layers such as indium tin oxide (ITO) or indium zinc oxide can be used, but are not limited to these. Photolithography techniques can be used to form the electrodes.

[0107] 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 elemental metals or mixtures containing aluminum, titanium, manganese, silver, lead, and chromium. Alternatively, alloys combining these elemental metals can also 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 may be used individually or in combination of two or more. The cathode may also be a single-layer or multi-layer structure. Among these, silver is preferred, and a silver alloy is even more preferred to reduce silver aggregation. The alloy ratio is not important as long as silver aggregation is reduced. For example, the ratio of silver to other metals may be 1:1, 3:1, etc.

[0108] 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 using DC and AC sputtering methods is more preferable because it provides good film coverage and makes it easier to reduce resistance.

[0109] [Organic Compound Layer] The organic compound layer may be formed as a single layer or as multiple layers. If there are multiple layers, they may be called a hole injection layer, a hole transport layer, an electron blocking layer, an emissive layer, a hole blocking layer, an electron transport layer, or an electron injection layer, depending on their function. The organic compound layer is mainly composed of organic compounds, but may also contain inorganic atoms and inorganic compounds. For example, it may contain copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, etc. The organic compound layer may be placed between the first electrode and the second electrode, or it may be placed in contact with the first electrode and the second electrode.

[0110] The organic compound layers constituting the organic light-emitting element according to this embodiment (hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, electron injection layer, etc.) are formed by the method shown below.

[0111] The organic compound layer constituting the organic light-emitting element according to this embodiment can be formed using a dry process such as vacuum deposition, ionization deposition, sputtering, or plasma deposition. Alternatively, instead of a dry process, a wet process can be used in which the layer is formed by dissolving the compound in a suitable solvent and applying a known coating method (e.g., spin coating, dipping, casting, LB method, inkjet method, etc.).

[0112] By forming layers using methods such as vacuum deposition or solution coating, crystallization is less likely to occur, resulting in excellent stability over time. Furthermore, when forming films using coating methods, it is possible to combine the film with an appropriate binder resin.

[0113] Examples of the binder resins mentioned above include, but are not limited to, polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenolic resin, epoxy resin, silicone resin, and urea resin.

[0114] Furthermore, these binder resins may be used individually as homopolymers or copolymers, or as a mixture of two or more types. Additionally, known additives such as plasticizers, antioxidants, and UV absorbers may be used in combination as needed.

[0115] [Protective Layer] A protective layer may be provided on the cathode. For example, by bonding glass with a desiccant to the cathode, the intrusion of water and other substances into the organic compound layer can be reduced, thereby reducing the occurrence of display defects. In another embodiment, a passivation film such as silicon nitride may be provided on the cathode to reduce the intrusion of water and other substances into the organic compound layer. For example, after forming the cathode, the material may be transported to another chamber without breaking the vacuum, and a silicon nitride film with a thickness of 2 μm may be formed by CVD to serve as a protective layer. A protective layer may also be provided using atomic deposition (ALD) after the film formation by CVD. The material of the film formed by ALD is not limited, but may be silicon nitride, silicon oxide, aluminum oxide, etc. Silicon nitride may be further formed by CVD on the film formed by ALD. The film formed by ALD may have a thinner film thickness than the film formed by CVD. Specifically, the film thickness of the film formed by the ALD method may be 50% or less, and even 10% or less, of the film thickness of the film formed by the CVD method.

[0116] [Color Filter] A color filter may be provided on top of the protective layer. For example, a color filter that takes into account the size of the organic light-emitting element may be provided on a separate substrate and bonded to the substrate on which the organic light-emitting element is provided, or a color filter may be patterned on the protective layer as described above using photolithography technology. The color filter may be made of polymer.

[0117] [Planarizing Layer] A planarizing layer may be provided between the color filter and the protective layer. The planarizing layer is provided for the purpose of reducing the unevenness of the layer below. It may also be called a material resin layer without limiting its purpose. The planarizing layer may be composed of an organic compound, and may be low molecular weight or high molecular weight, but high molecular weight is preferred.

[0118] The planarization layer may be provided above or below the color filter, and its constituent materials may be the same or different. Specifically, examples include polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenolic resin, epoxy resin, silicone resin, urea resin, etc.

[0119] [Microlens] The organic light-emitting element according to this embodiment may have an optical element such as a microlens on the light-emitting side. The microlens may be made of acrylic resin, epoxy resin, etc. The microlens may be used to increase the amount of light extracted from the organic light-emitting element and to control the direction of the extracted light. The microlens may have a hemispherical shape. If it has a hemispherical shape, among the tangents that are tangent to the hemisphere, there is a tangent that is parallel to the insulating layer, and the point of contact between that tangent and the hemisphere is the vertex of the microlens. The vertex of the microlens can be similarly determined in any cross-sectional view. That is, among the tangents that are tangent to the semicircle of the microlens in the cross-sectional view, there is a tangent that is parallel to the insulating layer, and the point of contact between that tangent and the semicircle is the vertex of the microlens.

[0120] Furthermore, the midpoint of a microlens can also be defined. In the cross-section of a microlens, a line segment can be imagined from the point where one arc shape begins to the point where another arc shape begins, and the midpoint of this line segment can be called the midpoint of the microlens. The cross-section used to determine the vertices and midpoints may be a cross-section perpendicular to the insulating layer.

[0121] [Opposite Substrate] An opposite substrate may be provided on the planarization layer. The opposite substrate is called an opposite substrate because it is provided in a position corresponding to the aforementioned substrate. The constituent material of the opposite substrate may be the same as that of the aforementioned substrate. The opposite substrate may be the second substrate if the aforementioned substrate is the first substrate.

[0122] [Pixel Circuit] The light-emitting device may have a pixel circuit connected to a light-emitting element. The pixel circuit may be an active-matrix type that independently controls the emission of light from a first light-emitting element and a second light-emitting element. 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 include 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.

[0123] The light-emitting device has a display area and a peripheral area arranged around the display area. The display area has a pixel circuit, and the peripheral area has a display control circuit. The mobility of the transistors constituting the pixel circuit may be smaller than the mobility of the transistors constituting the display control circuit.

[0124] The slope of the current-voltage characteristics of the transistors constituting the pixel circuit may be smaller than the slope of the current-voltage characteristics of the transistors constituting the display control circuit. The slope of the current-voltage characteristics can be measured using the so-called Vg-Ig characteristic.

[0125] The transistors that make up the pixel circuit are transistors connected to light-emitting elements, such as the first light-emitting element.

[0126] [Pixels] The organic light-emitting device has a plurality of pixels. Each pixel has sub-pixels that emit different colors from the others. The sub-pixels may each have, for example, RGB emission colors.

[0127] A pixel emits light in a region also called the pixel aperture. This region is the same as the first region. 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.

[0128] The distance between subpixels may be 10 μm or less, specifically 8 μm, 7.4 μm, or 6.4 μm.

[0129] Pixels can take on known arrangements in a plan view. For example, they may be in a stripe arrangement, delta arrangement, pentile arrangement, or Bayer arrangement. The shape of subpixels in a plan view may be any known shape. For example, rectangles, rhombuses, hexagons, etc. Of course, even if it is not a precise shape, if it is close to a rectangle, it is included in the category of rectangles. The shape of subpixels and the pixel arrangement can be used in combination.

[0130] (5) Applications of the Organic Light-Emitting Device According to This Embodiment The organic light-emitting device according to this embodiment can be used as a component of an image display device, a display device, a lighting device, etc. Other applications include a display unit for an image display device having a display unit and a housing on which the display unit is provided, an exposure light source for an electrophotographic image forming apparatus, a backlight for a liquid crystal display device, and a light-emitting device having a color filter in a white light source.

[0131] The display device may also be an image information processing device that has an image input unit for receiving image information from an area CCD, linear CCD, memory card, etc., an information processing unit for processing the input information, and displays the input image on the display unit.

[0132] Furthermore, the display unit of the imaging device or inkjet printer may have a touch panel function. The driving method for this touch panel function may be infrared, capacitive, resistive, or electromagnetic induction, and is not particularly limited. The display device may also be used as the display unit of a multifunction printer.

[0133] Next, the display device according to this embodiment will be described with reference to the drawings.

[0134] Figures 1A and 1B are schematic cross-sectional diagrams showing an example of a display device having an organic light-emitting element and a transistor connected to this organic light-emitting element. The transistor is an example of an active element. The transistor may also be a thin-film transistor (TFT).

[0135] Figure 1A shows an example of a pixel, which is a component of the display device according to this embodiment. The pixel has sub-pixels 10. The sub-pixels are divided into 10R, 10G, and 10B based on their light emission. The light emission color may be distinguished by the wavelength emitted from the light-emitting layer, or the light emitted from the sub-pixel may be selectively transmitted or color-converted by a color filter or the like. Each sub-pixel has a reflective electrode 2 which is a first electrode, an insulating layer 3 covering the end of the reflective electrode 2, an organic compound layer 4 covering the first electrode and the insulating layer, a transparent electrode 5, a protective layer 6, and a color filter 7 on an interlayer insulating layer 1.

[0136] The interlayer insulating layer 1 may have transistors and capacitive elements arranged in the layer below or inside it. The transistor and the first electrode may be electrically connected via a contact hole or the like (not shown).

[0137] The insulating layer 3 is also called a bank or pixel separation layer. It covers the edge of the first electrode and is arranged to surround the first electrode. The portion without the insulating layer is in contact with the organic compound layer 4 and becomes the light-emitting region.

[0138] The organic compound layer 4 includes a hole injection layer 41, a hole transport layer 42, a first light-emitting layer 43, a second light-emitting layer 44, and an electron transport layer 45.

[0139] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0140] The protective layer 6 reduces the penetration of moisture into the organic compound layer. Although the protective layer is shown as a single layer, it may consist of multiple layers. Each layer may contain an inorganic compound layer and an organic compound layer.

[0141] The color filters 7 are classified into 7R, 7G, and 7B according to their color. The color filters may be formed on a planarization film (not shown). The color filters may also have a resin protective layer (not shown). Alternatively, the color filters may be formed on a protective layer 6, or they may be bonded together after being placed on an opposing substrate such as a glass substrate.

[0142] Figure 1B shows a display device 100 which includes an organic light-emitting element 26 and a TFT 18 as an example of a transistor. A substrate 11 made of glass, silicon, or the like is provided, with an insulating layer 12 on top of it. An active element 18 such as a TFT is placed on the insulating layer, and the gate electrode 13, gate insulating film 14, and semiconductor layer 15 of the active element are arranged therein. The active element 18 is also composed of a semiconductor layer 15, a drain electrode 16, and a source electrode 17. An insulating film 19 is provided on top of the active element 18. The anode 21 and the source electrode 17 that constitute the organic light-emitting element 26 are connected via a contact hole 20 provided in the insulating film.

[0143] Note that the method of electrical connection between the electrodes (anode, cathode) included in the organic light-emitting element 26 and the electrodes (source electrode, drain electrode) included in the TFT is not limited to the configuration shown in Figure 1B. In other words, it is sufficient for either the anode or cathode to be electrically connected to either the TFT source electrode or the drain electrode. TFT refers to a thin-film transistor.

[0144] In the display device 100 shown in Figure 1B, the organic compound layer is depicted as a single layer, but the organic compound layer 22 may consist of multiple layers. A first protective layer 24 and a second protective layer 25 are provided on the cathode 23 to reduce the degradation of the organic light-emitting element.

[0145] In the display device 100 shown in Figure 1B, a transistor is used as the switching element, but other switching elements may be used instead.

[0146] Furthermore, the transistor used in the display device 100 in Figure 1B is not limited to a transistor using a single-crystal silicon wafer, but may also be a thin-film transistor having an active layer on an insulating surface of the substrate. Examples of active layers include non-single-crystal silicon such as single-crystal silicon, amorphous silicon, and microcrystalline silicon, and non-single-crystal oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Thin-film transistors are also called TFT elements.

[0147] The transistors included in the display device 100 in Figure 1B may be formed within a substrate such as a Si substrate. Here, "formed within a substrate" means that the transistors are manufactured by processing the substrate itself, such as a Si substrate. In other words, having transistors within a substrate can be seen as the substrate and transistors being formed as a single unit.

[0148] The organic light-emitting element according to this embodiment has its luminescence controlled by a TFT, which is an example of a switching element, and by providing multiple organic light-emitting elements on the surface, an image can be displayed according to the luminescence of each element. The switching element according to this embodiment is not limited to a TFT, but may also be a transistor made of low-temperature polysilicon, or an active matrix driver formed on a substrate such as a Si substrate. "On the substrate" can also mean "within the substrate." Whether to provide a transistor within the substrate or to use a TFT is selected depending on the size of the display area; for example, if the size is about 0.5 inches, it is preferable to provide the organic light-emitting element on a Si substrate.

[0149] Figure 2 is a schematic diagram showing an example of a display device according to this embodiment. The display device 1000 may have a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008 between an upper cover 1001 and a lower cover 1009. The display panel 1005 may have an organic light-emitting element according to this embodiment. Flexible printed circuits FPCs 1002 and 1004 are connected to the touch panel 1003 and the display panel 1005, respectively. Transistors are printed on the circuit board 1007. The battery 1008 does not need to be provided if the display device is not a portable device, or it may be provided in a different location even if it is a portable device.

[0150] The display device according to this embodiment may have a color filter having red, green, and blue colors. The color filter may have the red, green, and blue colors arranged in a delta array.

[0151] The display device according to this embodiment may be used in the display unit of a mobile terminal. In that case, it may have both display and operation functions. Examples of mobile terminals include smartphones and other mobile phones, tablets, and head-mounted displays.

[0152] The display device according to this embodiment may be used in the display unit of an imaging device having an image sensor that receives light. The imaging device may have a display unit that displays information acquired by the image sensor. The display unit may be an external display unit or a display unit located inside the viewfinder. The imaging device may be a digital camera or a digital video camera.

[0153] Figure 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 have organic light-emitting elements according to this embodiment. In that case, the viewfinder 1101 and the rear display 1102 may display not only the image to be captured, but also environmental information, imaging instructions, etc. Environmental information may include the intensity of ambient light, the direction of ambient light, the speed at which the subject is moving, the possibility of the subject being obscured by an obstacle, etc.

[0154] Since the optimal timing for imaging is very short, it is best to display the information as quickly as possible. Therefore, it is preferable to use a display device using the organic light-emitting element according to this embodiment, because organic light-emitting elements have a fast response speed.

[0155] The imaging device 1100 may further include an optical section (not shown). The lenses in the optical section may be one or more, and they form an image on the image sensor housed in the housing 1104. The focus can be adjusted by adjusting the relative positions of the multiple lenses. This operation can also be performed automatically. The imaging device may also be called a photoelectric converter. The photoelectric converter may not capture images sequentially, but may include methods of capturing images such as detecting the difference from the previous image or extracting from an image that is always being recorded.

[0156] Figure 3B is a schematic diagram showing an example of an electronic device according to this embodiment. The electronic device 1200 has a display unit 1201, an operation unit 1202, and a housing 1203. The housing 1203 may have a circuit, a printed circuit board having the circuit, a battery, and a communication unit. The operation unit 1202 may be a button or a touch panel type response unit. The operation unit may also be a biometric recognition unit that recognizes fingerprints to unlock or otherwise perform actions. An electronic device having a communication unit can also be called a communication device. The electronic device may further have a camera function by including a lens and an image sensor. Images captured by the camera function are displayed on the display unit. Examples of electronic devices include smartphones and laptop computers.

[0157] Figures 4A and 4B are schematic diagrams showing an example of a display device according to this embodiment. Figure 4A is a display device such as a television monitor or a PC monitor. The display device 1300 has a housing 1301 and a display unit 1302. An organic light-emitting element according to this embodiment may be used in the display unit 1302.

[0158] The display device 1300 may have a housing 1301 and a base 1303 that supports the display unit 1302. The base 1303 is not limited to the form shown in Figure 4A. The lower edge of the housing 1301 may also serve as the base.

[0159] Furthermore, the housing 1301 and the display unit 1302 may be curved. Their radius of curvature may be between 5000 mm and 6000 mm.

[0160] Figure 4B is a schematic diagram showing another example of a display device according to this embodiment. The display device 1310 in Figure 4B is configured to be foldable and is a so-called foldable display device. The display device 1310 has a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may have organic light-emitting elements according to this embodiment. The first display unit 1311 and the second display unit 1312 may be a single display device without seams. The first display unit 1311 and the second display unit 1312 can be separated by a bending point. The first display unit 1311 and the second display unit 1312 may each display different images, or the first and second display units may together display a single image.

[0161] Figure 5A is a schematic diagram showing an example of a lighting device according to this embodiment. The lighting device 1400 may have a housing 1401, a light source 1402, and a circuit board 1403. The light source 1402 may have an organic light-emitting element according to this embodiment. The lighting device 1400 may have an optical film 1404 to improve the color rendering of the light source. The lighting device 1400 may also have a light diffusion section 1405 to effectively diffuse the light from the light source. The lighting device 1400 having a light diffusion section 1405 allows light to be delivered over a wide area. The optical film 1404 and the light diffusion section 1405 may be provided on the light-emitting side of the lighting. A cover may be provided on the outermost part as needed.

[0162] The lighting device is, for example, a device for illuminating a room. The lighting device may emit white light, daylight white light, or any other color from blue to red. The lighting device according to this embodiment may have a dimming circuit for adjusting the brightness of these colors. The lighting device according to this embodiment may also have a power supply circuit connected to the organic light-emitting element according to this embodiment. The power supply circuit may be a circuit that converts AC voltage to DC voltage. White is defined as a color temperature of 4200K, and daylight white is defined as a color temperature of 5000K. The lighting device according to this embodiment may further have a color filter.

[0163] Furthermore, the lighting device according to this embodiment may have a heat dissipation section. The heat dissipation section releases heat from inside the device to the outside, and examples include metals, ceramics, and the like with high thermal conductivity.

[0164] Figure 5B is a schematic diagram of an automobile, which is an example of a mobile body according to this embodiment. The automobile has a taillight, which is an example of a lighting device. The automobile 1500 has a taillight 1501 and a body 1503, and the taillight may illuminate when the brakes are applied or the like. The body 1503 can also be called the machine body. The automobile 1500 may have a window 1502 attached to the body 1503. The taillight 1501 may have an organic light-emitting element according to this embodiment. The taillight may have a protective member to protect the light source. The protective member has a reasonably high strength and can be made of any material as long as it is transparent, but it is preferably made of polycarbonate or the like. A franciocarboxylic acid derivative, an acrylonitrile derivative, or the like may be mixed with the polycarbonate.

[0165] The window 1502 may be a transparent display if it is not a window for checking the front and rear of the automobile. The transparent display may have an organic light-emitting element according to this embodiment. In this case, the constituent materials such as electrodes of the organic light-emitting element according to the present invention are made of transparent material.

[0166] Furthermore, as shown in Figure 5C, the automobile 1500 includes a handle 1504 for controlling the direction of movement of the mobile body, a display unit 1505 mounted on the vehicle body 1503 for displaying a map, the position of the mobile body, the direction of turns, etc. The display unit 1505 may have an organic light-emitting element according to this embodiment. The mobile body according to this embodiment mainly includes a drive force generating unit that generates a driving force used for the movement of the mobile body, and one or both of a rotating body mainly used for the movement of the mobile body. The drive force generating unit may be an engine, motor, etc. The rotating body may be a tire, wheel, ship's propeller, etc. Specifically, it may be a bicycle, automobile, train, ship, aircraft, drone, etc. The mobile body may have a body and a light fixture provided on the body. The light fixture may emit light to let the position of the body be known.

[0167] With reference to Figures 6A and 6B, examples of applications of the display devices of each embodiment described above will be explained. The display device can be applied to systems that can be worn as wearable devices, such as smart glasses, head-mounted displays, and smart contact lenses. A display device that can be used in a wearable device may have an imaging device capable of photoelectric conversion of visible light and a display device capable of emitting visible light.

[0168] Figures 6A and 6B are schematic diagrams showing an example of eyeglasses (smart glasses) according to this embodiment. The eyeglasses 1600 (smart glasses) will be described using Figure 6A. The eyeglasses 1600 has a display unit on the back side of the lens 1601. The display unit may have an organic light-emitting element according to the present invention. Furthermore, an imaging device 1602 such as a CMOS sensor or SPAD may be provided on the front side of the lens 1601.

[0169] The eyeglasses 1600 further include a control device 1603. The control device 1603 functions as a power supply that provides power to the imaging device 1602 and the display unit. The control device 1603 also controls the operation of the imaging device 1602 and the display unit. The lens 1601 has an optical system formed therein for focusing light from the imaging device 1602 and the display unit.

[0170] Figure 6B will be used to describe the eyeglasses 1610 (smart glasses). The eyeglasses 1610 have a control device 1612, and the control device 1612 is equipped with a display device having an organic light-emitting element according to the present invention. The control device 1612 may further have an imaging device corresponding to an 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 supply that supplies power to the imaging device and the display device, and also controls the operation of the imaging device and the display device. The control device may have a gaze detection unit that detects the wearer's gaze. Gaze detection may use infrared light. The infrared light-emitting unit emits infrared light towards the eyeball of the user who is gazing at the displayed image. An image of the eyeball is obtained by detecting the reflected light from the eyeball of the emitted infrared light with an imaging unit having a light-receiving element. By having a reduction means that reduces the light from the infrared light-emitting unit to the display unit in planar view, the deterioration of image quality is reduced.

[0171] The control device 1612 detects the user's gaze toward the displayed image from the image of the eyeball obtained by imaging with infrared light. Any known method can be applied to gaze detection using the image of the eyeball. For example, a gaze detection method based on the Purkinje image obtained by the reflection of the irradiated light from the cornea can be used.

[0172] More specifically, gaze detection processing is performed based on the pupil-corneal reflection method. Using the pupil-corneal reflection method, a gaze vector representing the orientation (rotation angle) of the eyeball is produced based on the pupil image and Purkinje image contained in the captured image of the eyeball, thereby detecting the user's gaze.

[0173] The display device according to this embodiment includes an imaging device having a light-receiving element, and may control the display image of the display device based on the user's gaze information from the imaging device.

[0174] Specifically, the display device determines a first field of view that the user is fixated on, and a second field of view other than the first field of view, based on gaze information. The first and second field of view may be determined by the display device's control unit, or they may be determined by an external control unit and received by the display device. Within the display area of ​​the display device, the display resolution of the first field of view may be controlled to be higher than that of the second field of view. In other words, the resolution of the second field of view may be lower than that of the first field of view.

[0175] Furthermore, the display area has a first field of view and a second field of view different from the first field of view, and based on gaze information, a higher priority area is determined from the first and second field of view. The first and second field of view areas may be determined by the control device of the display device, or they may be determined by an external control device and received. The resolution of the higher priority area may be controlled to be higher than the resolution of the areas other than the higher priority area. In other words, the resolution of areas with relatively lower priority may be set lower.

[0176] AI may be used to determine the first field of view and the field of view with higher priority. The AI ​​may be a model configured to estimate the angle of line of sight and the distance to the target object at the end of the line of sight from the image of the eye, using the image of the eye and the direction the eye was actually looking in the image as training data. The AI ​​may be provided by the display device, the imaging device, or an external device. If the external device has the AI, it can preferably be applied to smart glasses that further have an imaging device for capturing images of the outside. The smart glasses can display the captured external information in real time.

[0177] Figure 7A is a schematic diagram showing an example of an image forming apparatus according to this embodiment. The image forming apparatus 40 is an electrophotographic image forming apparatus and includes a photoreceptor 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transfer unit 32, a transport roller 33, and a fuser 35. Light 29 is irradiated from the exposure light source 28, and an electrostatic latent image is formed on the surface of the photoreceptor 27. This exposure light source 28 may have an organic light-emitting element according to this embodiment. The developing unit 31 has toner or the like. The charging unit 30 charges the photoreceptor 27. The transfer unit 32 transfers the developed image to a storage medium 34. The transport roller 33 transports the recording medium 34. The recording medium 34 is, for example, paper. The fuser 35 fixes the image formed on the recording medium 34.

[0178] Figures 7B and 7C are diagrams showing the exposure light source 28, schematic diagrams showing how multiple light-emitting units 36 are arranged on a long substrate. Arrows 37 indicate the direction of the column in which the organic light-emitting elements are arranged. This column direction is the same as the direction of the axis in which the photoreceptor 27 rotates. This direction can also be called the long axis direction of the photoreceptor 27. Figure 7B shows a configuration in which the light-emitting units 36 are arranged along the long axis direction of the photoreceptor 27. Figure 7C shows a different configuration from Figure 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 with intervals between them. In the second column, light-emitting units 36 are located at positions corresponding to the intervals between the light-emitting units 36 in the first column. That is, multiple light-emitting units 36 are also arranged with intervals between them in the row direction. The arrangement in Figure 7C can also be described as a grid pattern, a houndstooth pattern, or a checkerboard pattern.

[0179] As described above, by using the device employing the organic light-emitting element according to this embodiment, stable display with good image quality is possible even during long-term display.

[0180] The present invention will be described below with reference to examples. However, the present invention is not limited to these examples.

[0181] [Example 1 (Synthesis of Compound)] (1) Synthesis of BD-1 Compound BD-1 was synthesized using the following synthesis route.

[0182]

[0183] (1-1) I-1 was synthesized by adding dichlorobenzene (9.6 g), chloroform (60 mL), and aluminum chloride (8.75 g). Under an ice bath, isopropyl chloride (13.2 mL) was added and the mixture was stirred for 2 hours. After adding ice water and extracting with chloroform, the solution was concentrated to obtain a pale yellow clear liquid I-1 (crude) (14.41 g).

[0184] (1-2) Synthesis of I-2: Dichlorodiisopropylbenzene (14.41 g crude grade), 1,2-Dichloroethanol (DCE) (250 ml), iodine (31.5 g), and potassium peroxodisulfate (33.6 g) were added, and trifluoroacetic acid (TFA) (50 ml) and sulfuric acid (2 ml) were added under ice bath. The mixture was then stirred at 60°C for 40 hours. Sodium sulfite aqueous solution was added, and the mixture was extracted with dichloromethane and concentrated. Silica suction filtration was performed with dichloromethane / hexane. Then 20 ml of toluene was added and dissolved at 80°C, and 240 ml of ethanol was added and the mixture was cooled to room temperature. Washing with ethanol and suction filtration was performed to obtain a white solid I-2 (5.08 g).

[0185] (1-3) Synthesis of I-3 1-Chloro-3-methoxy-2-nitrobenzene (10 g) was dissolved in chloroform (200 mL), then bromine (3 ml) and iron chloride (8.66 g) were added, and the mixture was stirred at room temperature for 20 hours. The reaction solution was filtered by silica suction filtration with chloroform. After concentration, it was washed with methanol and filtered to obtain white powder I-3 (12.35 g).

[0186] (1-4) Synthesis of I-4 I-3 (12.35 g), phenylboronic acid (5.65 g), tetrakistriphenylphosphine palladium (1.07 g), sodium carbonate (9.81 g), dioxane (210 mL), and water (70 mL) were added and stirred under nitrogen at 90°C for 12 hours. After washing with toluene and concentrating, the mixture was washed with methanol and filtered to obtain 9.04 g of white powder (I-4).

[0187] (1-5) Synthesis of I-5 I-4 (9.04 g), dibenzoflamboronic acid (8.72 g), palladium acetate (0.153 g), SPhos (0.562 g), potassium carbonate (9.45 g), dioxane (200 mL), and water (100 mL) were added and bubbling was performed with argon. The mixture was stirred under nitrogen at 90°C for 12 hours. Extraction was performed with toluene and filtered by silica suction. After concentration, the mixture was washed with methanol, filtered, and vacuum dried at 50°C to obtain 10.2 g of white powder (I-5).

[0188] (1-6) Synthesis of I-6 I-5 (10.2 g) and dichloromethane (200 mL) were added, and boron tribromide (1 M dichloromethane solution) (30.9 ml) was added under ice bath. The mixture was stirred for 12 hours. Water was added, and the mixture was extracted with dichloromethane and concentrated. It was purified by silica gel chromatography (ethyl acetate:hexane = 1:2) to obtain I-6.

[0189] (1-7) Synthesis of I-7 I-6, dichloromethane (200 mL), pyridine (4.54 mL) were added under ice bath, and anhydrous trifluoroacetic acid (6.18 mL) was added. The mixture was stirred for 12 hours. Water was added, and the mixture was extracted with dichloromethane and concentrated. The mixture was washed with methanol and filtered to obtain 12.07 g of white powder (I-7).

[0190] (1-8) Synthesis of I-8 I-7 (3g), MoO ２ Cl ２ (dmf) ２ (0.507 g), triphenylphosphine (4.595 g), and toluene (120 ml) were added. The mixture was stirred at 120°C for 30 hours. The mixture was concentrated by silica suction filtration with toluene. The mixture was washed with methanol / hexane and filtered to obtain 2.49 g of white powder (I-8).

[0191] (1-9) Synthesis of I-9: I-8 (1.6g), (BPin) ２ (1.01g), Pd ２ (dba) ３(0.091 g), XPhos (0.095 g), potassium acetate (0.978 g), and THF (150 mL) were added and argon bubbling was performed. The mixture was stirred under nitrogen at 80°C for 12 hours. Extraction was performed with dichloromethane and filtered by silica suction. After concentration, silica gel chromatography (ethyl acetate:hexane = 15:85) was performed to obtain 0.973 g of powder (I-9).

[0192] (1-10) Synthesis of I-10: I-2 (0.236 g), I-9 (0.785 g), Pd ２ (dba) ３ (0.023 g), tri-tert-butylphosphonium tetrafluoroborate (0.014 g), potassium carbonate (0.300 g), THF (50 mL), and water (5 mL) were added, and the mixture was bubbled with argon. The mixture was stirred at 80°C for 12 hours. The mixture was washed with methanol / water and filtered to obtain 0.218 g of gray powder (I-10 (crude)).

[0193] (1-11) Synthesis of BD-1 0.100 g of I-10 (crude), 0.021 g of copper iodide, 20.1 g of 1,10-phenanthroline monohydrate, and 0.095 g of potassium phosphate were added and bubbling was performed with argon. The mixture was stirred at 150°C for 12 hours. 1N HCl was added and the mixture was filtered. After concentration, silica gel chromatography (toluene:hexane = 10:90) was performed to obtain BD-1 (0.013 g). Mass spectrometry (MALDI-TOF MS) showed a molecular weight of 820.3090 and a m / z of 820.3105. Figure 8 shows the normalized emission spectrum of compound BD-1 in toluene solution.

[0194] [Comparative Example 1 (Synthesis of BD-C1 and BD-C2)] (1-1) Synthesis of BD-C1 Compound BD-C1 was synthesized using I-11 instead of I-9 in the synthesis route of BD-1. Figure 9 shows the normalized emission spectrum of compound BD-C1 in toluene solution.

[0195]

[0196] (1-2) Synthesis of BD-C2 Compound BD-C2 was synthesized using 1,4-dibromo-2,5-diiodobenzene instead of I-2 in the synthesis route of BD-1. Figure 10 shows the normalized emission spectrum of compound BD-C2 in toluene solution.

[0197] [Example 2, Comparative Example 2 (Measurement of Luminescence Quantum Yield of Organic Compounds)] Compounds BD-1, BD-C1, and BD-C2 were dissolved in toluene, and the toluene solution was irradiated with excitation light at 430 nm to measure the luminescence quantum yield (PLQY). The results are shown in Table 2.

[0198]

[0199] Table 2 shows that the PLQY of BD-1, an organic compound according to the present invention, was higher than that of the comparative examples BD-C1 and BD-C2. This is thought to be because the organic compound according to the present invention, by having substituents at predetermined positions, reduces the overall planarity of the molecule and suppresses aggregation between molecules.

[0200] Furthermore, referring to the cohesive energy density listed in Table 1, the cohesive energy density of BD-1 is 27 kcal mol. －１ nm －３ In contrast, the cohesive energy densities of BD-C1 and BD-C2 are 41 kcal mol, respectively. －１ nm －３ and 39 kcal mol －１ nm －３ Therefore, the cohesive energy density of BD-1 is lower than that of BD-C1 and BD-C2. Since molecules are less likely to aggregate when the cohesive energy density is lower, it is thought that BD-1 exhibited superior luminescence efficiency. Thus, it was found that the organic compound according to the present invention is an organic compound that exhibits excellent luminescence efficiency.

[0201] Based on the above, the organic compound according to the present invention is an organic compound that exhibits excellent luminescence efficiency.

[0202] Furthermore, the present invention can also take the following configuration.

[0203] (Composition 1) An organic compound characterized by being represented by any one of the general formulas G1 to G6.

[0204]

[0205] In general formulas G1 to G6, R １２ ~R １８ , R ２２ ~R ２８ , R ３１ , R ３２ , R １１１ ~R １１４ , R ２１１ ~R ２１４ Each of the following groups is independently selected from the group consisting of hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted thioalkoxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted thioaryl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted thioheteroaryl groups, substituted or unsubstituted heteroaryloxy groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amino groups, cyano groups, and nitro groups. However, R ３１ and R ３２ At least one of them is a non-hydrogen atom, R １２ ~R １８ , R ２２ ~R ２８ , R １１１ ~R １１４ , R ２１１ ~R ２１４ At least one of them is not a hydrogen atom. １ and X ２ Each of these atoms is independently selected from the group consisting of oxygen atoms, sulfur atoms, tellurium atoms, and selenium atoms.

[0206] (Configuration 2) In general formulas G1 to G6, X １ and X ２ The organic compound according to configuration 1, characterized in that one of the atoms is an oxygen atom or a sulfur atom.

[0207] (Configuration 3) In general formulas G1 to G6, R１３ and R ２３ , R １４ and R ２４ , R １５ and R ２５ , R １７ and R ２７ , R １８ and R ２８ , R １１１ and R ２１１ , R ２１２ and R ２１２ , R １１３ and R ２１３ , R １１４ and R ２１４ The organic compound according to configuration 1 or 2, characterized in that at least one set of substituents is a hydrogen atom.

[0208] (Configuration 4) In general formulas G1 to G6, R １３ and R ２３ , R １４ and R ２４ , R １７ and R ２７ , R １８ and R ２８ , R １１１ and R ２１１ , R ２１２ and R ２１２ , R １１３ and R ２１３ , R １１４ and R ２１４ An organic compound according to any one of configurations 1 to 3, characterized in that at least one set of substituents is other than a hydrogen atom.

[0209] (Configuration 5) In general formulas G1 to G6, R １４ and R ２４ An organic compound according to any one of configurations 1 to 4, characterized in that the substituent is a hydrogen atom.

[0210] (Configuration 6) In general formulas G1 to G6, R ３１ or R ３２ The organic compound according to any one of configurations 1 to 5, characterized in that at least one of the members is an alkyl group having 3 to 5 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, or an amino group having 6 to 10 carbon atoms.

[0211] (Configuration 7) In general formulas G1 to G6, R ３１ or R ３２ The organic compound according to any one of configurations 1 to 6, characterized in that at least one of the members is an alkyl group having 3 to 5 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or an amino group having 6 to 10 carbon atoms.

[0212] (Configuration 8) In general formulas G1 to G6, R ３１ or R ３２ At least one of them is an iso-propyl group, a tert-butyl group, or C(C ２ H ５ ) ２ The organic compound according to any one of the configurations 1 to 7, characterized by being a phenyl group, a phenyl group having an alkyl group with 1 to 4 carbon atoms, a phenyl group having a cyano group, a biphenyl group, or an amino group having a phenyl group.

[0213] (Configuration 9) The organic compound according to Configuration 8, characterized in that the alkyl group having 1 to 4 carbon atoms is a methyl group, an iso-propyl group, or a tert-butyl group.

[0214] (Configuration 10) In general formulas G1 to G6, R ３１ and R ３２ An organic compound according to any one of configurations 1 to 9, characterized in that the substituent is a hydrogen atom.

[0215] (Configuration 11) In general formulas G1 to G6, R １２ ~R １８ , R ２２ ~R ２８ , R １１１ ~R １１４ , R ２１１ ~R ２１４ The organic compound according to any one of configurations 1 to 10, characterized in that at least one of the members is an alkyl group having 3 to 5 carbon atoms, a substituted or unsubstituted aryl group having 6 to 16 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

[0216] (Configuration 12) In general formulas G1 to G6, R １２ ~R １８ , R ２２ ~R ２８ , R １１１ ~R １１４ , R ２１１ ~R ２１４ The organic compound according to any one of configurations 1 to 11, characterized in that at least one of the members is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 12 carbon atoms, or an alkyl group having 3 to 5 carbon atoms.

[0217] (Configuration 13) In general formulas G1 to G6, R １２ ~R １８ , R ２２ ~R ２８ , R １１１ ~R １１４ , R ２１１ ~R ２１４ The organic compound according to any one of configurations 1 to 12, characterized in that at least one of the members is an aryl group having 6 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms and an alkyl group having 1 to 4 carbon atoms, a heteroaryl group having 6 to 12 carbon atoms, or an alkyl group having 3 to 5 carbon atoms.

[0218] (Configuration 14) The organic compound according to Configuration 13, characterized in that the alkyl group having 1 to 4 carbon atoms is a methyl group, an iso-propyl group, or a tert-butyl group.

[0219] (Configuration 15) The organic compound according to any one of Configurations 1 to 14, characterized in that the organic compound is represented by the general formula G1 or G2.

[0220] (Configuration 16) An organic light-emitting element having a first electrode and a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, wherein the organic compound layer has an organic compound as described in any of Configurations 1 to 15.

[0221] (Configuration 17) The organic light-emitting element according to Configuration 16, wherein the organic compound layer has a light-emitting layer, and the light-emitting layer has the organic compound.

[0222] (Configuration 18) The organic light-emitting element according to Configuration 17, wherein the light-emitting layer further comprises a first compound, and the lowest singlet excitation energy of the first compound is higher than the lowest singlet excitation energy of the organic compound.

[0223] (Configuration 19) The organic light-emitting element according to Configuration 18, wherein the light-emitting layer further comprises a second compound, and the lowest singlet excitation energy of the second compound is higher than the lowest singlet excitation energy of the organic compound and lower than the lowest singlet excitation energy of the first compound.

[0224] (Configuration 20) A display device having a plurality of pixels, wherein at least one of the plurality of pixels has an organic light-emitting element as described in any of Configurations 16 to 19 and a transistor connected to the organic light-emitting element.

[0225] (Configuration 21) A photoelectric conversion device comprising an image sensor that receives light and a display unit that displays an image captured by the image sensor, wherein the display unit has an organic light-emitting element as described in any of Configurations 16 to 19.

[0226] (Configuration 22) An image display device characterized by having a display unit having an organic light-emitting element as described in any of Configurations 16 to 19, and a housing on which the display unit is provided.

[0227] (Configuration 23) An electronic device comprising: a display unit having an organic light-emitting element as described in any of Configurations 16 to 19; a housing on which the display unit is provided; and a communication unit provided in the housing for communicating with the outside.

[0228] (Configuration 24) A wearable device comprising: a display unit having an organic light-emitting element as described in any of Configurations 16 to 19; an optical system for focusing light from the display unit; and a control device for controlling the display of the display unit.

[0229] (Configuration 25) A lighting device characterized by comprising a light source having an organic light-emitting element as described in any of Configurations 16 to 19, and a housing on which the light source is provided.

[0230] (Configuration 26) A mobile body characterized by having a light fixture having an organic light-emitting element as described in any of Configurations 16 to 19, and a body on which the light fixture is provided.

[0231] The present invention is not limited to the embodiments described above, and various modifications and variations are possible without departing from the spirit and scope of the invention. Accordingly, the following claims are attached to make the scope of the invention public.

[0232] This application claims priority based on Japanese Patent Application No. 2024-200562, filed on 18 November 2024, and all of its contents are incorporated herein by reference.

[0233] 1 Interlayer insulating layer 2 Reflective electrode 3 Insulating layer 4 Organic compound layer 5 Transparent electrode 6 Protective layer 7 Color filter 10 Sub-pixel 11 Substrate 12 Insulating layer 13 Gate electrode 14 Gate insulating film 15 Semiconductor layer 16 Drain electrode 17 Source electrode 18 Thin film transistor 19 Insulating film 20 Contact hole 21 Lower electrode 22 Organic compound layer 23 Upper electrode 24 First protective layer 25 Second protective layer 26 Organic light-emitting element 27 Photoreceptor 28 Exposure light source 29 Light 30 Charging unit 31 Developing unit 32 Transfer unit 33 Transport unit 34 Recording medium 35 Fixing unit 36 ​​Light-emitting unit 37 First direction parallel to the long axis of the photoreceptor 40 Image forming apparatus 100 Display device 1000 Display device 1001 Upper cover 1002 Flexible printed circuit board 1003 Touch panel 1004 Flexible printed circuit board 1005 Display panel 1006 Frame 1007 Circuit board 1008 Battery 1009 Lower cover 1100 Imaging device 1101 Viewfinder 1102 Rear display 1103 Operation unit 1104 Housing 1200 Electronic equipment 1201 Display unit 1202 Operation unit 1203 Housing 1300 Display device 1301 Frame 1302 Display unit 1303 Base 1310 Display device 1311 First display unit 1312 Second display unit 1313 Housing 1314 Bending point 1400 Lighting device 1401 Housing 1402 Light source 1403 Circuit board 1404 Optical film 1405 Light diffusion unit 1500 Automobile 1501 Taillight 1502 Window 1503 Body 1600 Smart Glasses 1601 Lens 1602 Imaging Device 1603 Control Device 1610 Smart Glasses 1611 Lens 1612 Control Device

Claims

1. An organic compound characterized by being represented by any one of general formulas G1 to G6. In general formulas G1 to G6, R １ , ２ , ２１４ to R １８ , R ２２ to R ２８ , R ３１ , R ３２ , R １１１ to R １１４ , R ２１１ to R ２１４ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thioalkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted thioaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted thioheteroaryl group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a cyano group, and a nitro group. However, at least one of R ３１ and R ３２ is other than a hydrogen atom and a deuterium atom, and at least one of R １２ to R １８ , R ２２ to R ２８ , R １１１ to R １１４ , R ２１１ to R ２１４ is other than a hydrogen atom. X １ and X ２ are each independently selected from the group consisting of an oxygen atom, a sulfur atom, a tellurium atom, and a selenium atom.

2. In general formulas G1 to G6, X １ and X ２ The organic compound according to claim 1, characterized in that one of the atoms is an oxygen atom or a sulfur atom.

3. In general formulas G1 to G6, R １３ and R ２３ , R １４ and R ２４ , R １５ and R ２５ , R １７ and R ２７ , R １８ and R ２８ , R １１１ and R ２１１ , R ２１２ and R ２１２ , R １１３ and R ２１３ , R １１４ and R ２１４ The organic compound according to claim 1, characterized in that at least one of the substituents is a hydrogen atom.

4. In general formulas G1 to G6, R １３ and R ２３ , R １４ and R ２４ , R １７ and R ２７ , R １８ and R ２８ , R １１１ and R ２１１ , R ２１２ and R ２１２ , R １１３ and R ２１３ , R １１４ and R ２１４ The organic compound according to claim 1, characterized in that at least one of the substituents is a hydrogen atom.

5. In general formulas G1 to G6, R １４ and R ２４ The organic compound according to claim 1, characterized in that the substituent is a hydrogen atom.

6. In general formulas G1 to G6, R ３１ or R ３２ The organic compound according to claim 1, characterized in that at least one of the members is an alkyl group having 3 to 5 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, or an amino group having 6 to 10 carbon atoms.

7. In general formulas G1 to G6, R ３１ or R ３２ The organic compound according to claim 1, characterized in that at least one of the members is an alkyl group having 3 to 5 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or an amino group having 6 to 10 carbon atoms.

8. In general formulas G1 to G6, R ３１ or R ３２ At least one of them is an iso-propyl group, a tert-butyl group, or C(C ２ H ５ ) ２ The organic compound according to claim 1, characterized in that it is a phenyl group, a phenyl group having an alkyl group with 1 to 4 carbon atoms, a phenyl group having a cyano group, a biphenyl group, or an amino group having a phenyl group.

9. The organic compound according to claim 8, characterized in that the alkyl group having 1 to 4 carbon atoms is a methyl group, an iso-propyl group, or a tert-butyl group.

10. In general formulas G1 to G6, R ３１ and R ３２ The organic compound according to claim 1, characterized in that the substituent is a hydrogen atom.

11. In general formulas G1 to G6, R １２ ~R １８ , R ２２ ~R ２８ , R １１１ ~R １１４ , R ２１１ ~R ２１４ The organic compound according to claim 1, characterized in that at least one of the members is an alkyl group having 3 to 5 carbon atoms, a substituted or unsubstituted aryl group having 6 to 16 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

12. In general formulas G1 to G6, R １２ ~R １８ , R ２２ ~R ２８ , R １１１ ~R １１４ , R ２１１ ~R ２１４ The organic compound according to claim 1, characterized in that at least one of the members is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 12 carbon atoms, or an alkyl group having 3 to 5 carbon atoms.

13. In General Formulas G1 to G6, R １２ to R １８ 、R ２２ to R ２８ 、R １１１ to R １１４ 、R ２１１ to R ２１４ at least one of which is an aryl group having 6 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms and having an alkyl group having 1 to 4 carbon atoms, a heteroaryl group having 6 to 12 carbon atoms, or an alkyl group having 3 to 5 carbon atoms. The organic compound according to claim 1, characterized in that.

14. The organic compound according to claim 13, characterized in that the alkyl group having 1 to 4 carbon atoms is a methyl group, an iso-propyl group, or a tert-butyl group.

15. The organic compound according to claim 1, characterized in that the organic compound is represented by the general formula G1 or G2.

16. An organic light-emitting element having a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, wherein the organic compound layer has the organic compound described in claim 1.

17. The organic light-emitting element according to claim 16, wherein the organic compound layer has a light-emitting layer, and the light-emitting layer has the organic compound.

18. The organic light-emitting element according to claim 17, wherein the light-emitting layer further comprises a first compound, and the lowest singlet excitation energy of the first compound is higher than the lowest singlet excitation energy of the organic compound.

19. The organic light-emitting element according to claim 18, wherein the light-emitting layer further comprises a second compound, and the lowest singlet excitation energy of the second compound is higher than the lowest singlet excitation energy of the organic compound and lower than the lowest singlet excitation energy of the first compound.

20. A display device having a plurality of pixels, wherein at least one of the plurality of pixels comprises an organic light-emitting element according to any one of claims 16 to 19 and a transistor connected to the organic light-emitting element.

21. A photoelectric conversion device comprising an image sensor that receives light and a display unit that displays an image captured by the image sensor, wherein the display unit has an organic light-emitting element as described in any one of claims 16 to 19.

22. An image display device comprising a display unit having an organic light-emitting element as described in any one of claims 16 to 19, and a housing on which the display unit is provided.

23. An electronic device comprising: a display unit having an organic light-emitting element as described in any one of claims 16 to 19; a housing on which the display unit is provided; and a communication unit provided in the housing for communicating with the outside.

24. A wearable device comprising: a display unit having an organic light-emitting element as described in any one of claims 16 to 19; an optical system for focusing light from the display unit; and a control device for controlling the display of the display unit.

25. A lighting device comprising a light source having an organic light-emitting element as described in any one of claims 16 to 19, and a housing on which the light source is provided.

26. A mobile body characterized by comprising a lamp having an organic light-emitting element as described in any one of claims 16 to 19, and a body on which the lamp is provided.

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