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

Abstract

Provided is an organic compound represented by formula (1) and exhibiting a small ΔEST. R11-R16 and R21-R26 are each independently selected from the group consisting of a hydrogen atom, alkyl groups, and the like. RC is selected from the group consisting of a hydrogen atom, alkyl groups, and the like. A CyA ring and a CyB ring are each independently selected from the group consisting of aryl rings having 6-13 carbon atoms, and heteroaryl rings having 3-12 carbon atoms. RA and RB each represent a group bonded to a heteroatom or a carbon atom forming the CyA ring and the CyB ring, and are each independently selected from the group consisting of a hydrogen atom, alkyl groups, and the like. n and m each represent an integer of 4-14. X1 and X2 are each independently selected from the chalcogen atom group consisting of an oxygen atom, a sulfur atom, and the like. Y1 and Y2 are each independently selected from an oxygen atom and a sulfur atom.

Description

Organic compounds, organic light-emitting elements, ink compositions, display devices, photoelectric converters, image display devices, electronic devices, wearable devices, lighting devices, mobile devices, and exposure light sources.

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

[0002] Organic light-emitting devices (hereinafter sometimes referred to as "organic electroluminescent devices" or "organic EL devices") are electronic devices having a first electrode, a second electrode, and an organic compound layer placed between these electrodes. By injecting electrons and holes from this pair of electrodes, excitons of the luminescent organic compound in the organic compound layer are generated, and when these excitons return to the ground state, the organic light-emitting device emits light. Recent advances in organic light-emitting devices have been remarkable, and their features include low driving voltage, diverse emission wavelengths, fast response, and the ability to make light-emitting devices thinner and lighter. Currently, as an attempt to improve the luminescence efficiency of organic EL devices, the use of thermally activated delayed fluorescence (TADF) materials has been proposed. TADF materials are organic compounds that undergo reverse intersystem crossing from a triplet excited state to a singlet excited state, and organic EL devices using them are theoretically expected to have approximately four times the luminescence efficiency of devices using ordinary fluorescent light-emitting materials. Therefore, there has been a great deal of effort to create delayed fluorescence materials. In recent years, MR (multi-resonance)-TADF materials, which exhibit a narrow emission spectrum and excellent color purity, have also attracted attention. Patent Document 1 describes compound A as an luminescent material that can achieve a narrow emission spectrum and high color purity, and Patent Document 2 describes compound B as an luminescent material that can achieve high color purity and high efficiency.

[0003]

[0004] U.S. Patent Application Publication No. 2020 / 0185635, Japanese Patent Publication No. 2023-92457

[0005] Compound A described in Patent Document 1 is a material with a narrow emission spectrum width and excellent color purity. Similarly, compound B described in Patent Document 2 is also a material with a narrow emission spectrum width and excellent color purity. However, in these documents, the narrowing and verification of ΔE ST have not been studied, and there are problems in the material design for improving the emission efficiency. The present invention has been made in view of the above problems, and its object is to provide an organic compound showing a small ΔE ST .

[0006] The organic compound according to the present invention is characterized by being represented by the following general formula (1).

[0007] In general formula (1), R 11 to R 16 , R 21 to R 26 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. R C is selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. The Cy A ring and the Cy B ring are each independently selected from the group consisting of an aryl ring having 6 to 13 carbon atoms and a heteroaryl ring having 3 to 12 carbon atoms. R A and R B are each a Cy A ring and a Cy BThis represents a group bonded to a carbon or heteroatom constituting a ring, and is independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic, substituted or unsubstituted amino, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryloxy, substituted or unsubstituted silyl, and cyano groups. A Allies, adjacent R B They may be bonded together to form a ring. n and m each represent an integer between 4 and 14. X1 and X2 are independently selected from the chalcogen atom group consisting of oxygen, sulfur, selenium, and tellurium atoms. Y1 and Y2 are independently selected from oxygen and sulfur atoms, respectively.

[0008] According to the present invention, a small ΔE ST We can provide organic compounds having the following properties.

[0009] Other features and advantages of this disclosure will become apparent from the following description with reference to the accompanying drawings. In the accompanying drawings, the same or similar components are given the same reference numeral.

[0010] The attached drawings are included in the specification and constitute part thereof, illustrating embodiments of the disclosure and are used together with the description to illustrate the principles of the disclosure.

[0011] This figure shows the HOMO / LUMO orbital distributions of compound A, compound C, and example compound 1. This figure shows the HOMO / LUMO orbital distributions of compound D, compound E, and example compound 10. This is a schematic cross-sectional view showing an example of a pixel of 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 light-emitting 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 a mobile body having a vehicle light 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 another example of a wearable 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.

[0012] The embodiments will be described in detail below with reference to the attached drawings. Note that the following embodiments do not limit the scope of the claims. While the embodiments describe multiple features, not all of these features are necessary, and the features may be combined in any way. Furthermore, in the attached drawings, identical or similar configurations are given the same reference numerals, and redundant descriptions are omitted.

[0013] (1) Organic compound An organic compound according to one embodiment of the present invention is represented by the following formula (1).

[0014]

[0015] <R 11 ~R 16 , R 21 ~R 26 > In general formula (1), R 11 ~R 16 , R 21 ~R26 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 aryl groups, substituted or unsubstituted heterocyclic groups, substituted or unsubstituted amino groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryloxy groups, substituted or unsubstituted silyl groups, and cyano groups.

[0016] R 11 ~R 16 , R 21 ~R 26 This may be a hydrogen atom, a deuterium atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heterocyclic group having 4 to 12 carbon atoms, an amino group having 6 to 12 carbon atoms, or a cyano group, and may also be a hydrogen atom, an alkyl group having 1 to 7 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heterocyclic group having 4 to 12 carbon atoms, or a cyano group, and may also be a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a cyano group. Furthermore, R 11 ~R 16 , R 21 ~R 26 If the group is anything other than a hydrogen atom, it may be a methyl group, iso-propyl group, tert-butyl group, diarylamine group, phenyl group, phenyl group with an alkyl group as a substituent, or biphenyl group. Having these groups may help suppress aggregation of organic compounds and improve sublimation and solubility.

[0017] <R C > In general formula (1), R C This is selected from the group consisting of hydrogen atoms, deuterium atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heterocyclic groups, substituted or unsubstituted amino groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryloxy groups, substituted or unsubstituted silyl groups, and cyano groups.

[0018] R CThis may be a hydrogen atom, a deuterium atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heterocyclic group having 4 to 12 carbon atoms, an amino group having 6 to 12 carbon atoms, or a cyano group. It may also be a hydrogen atom, an alkyl group having 1 to 7 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heterocyclic group having 4 to 12 carbon atoms, or a cyano group. It may also be a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a cyano group. C This may be a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 carbon atoms, and may also be an alkyl group having 1 to 4 carbon atoms. Furthermore, R C If the group is anything other than a hydrogen atom, it may be a methyl group, iso-propyl group, tert-butyl group, diarylamine group, phenyl group, phenyl group with an alkyl group as a substituent, or biphenyl group. Having these groups may help suppress aggregation of organic compounds and improve sublimation and solubility.

[0019] <Cy A and Cy B > In general formula (1), Cy A Ring and Cy B The ring is independently selected from the group consisting of aryl rings with 6 to 13 carbon atoms and heteroaryl rings with 3 to 12 carbon atoms. An aryl ring is a ring structure consisting only of hydrocarbons, such as a benzene ring or a naphthalene ring. A heteroaryl ring is a ring structure consisting of a hydrocarbon and a heteroatom, such as a pyridine ring or a dibenzofuran ring. However, the substituents bonded to the ring structure are not limited to hydrocarbons. A Ring and Cy B The ring may be a benzene ring having 6 carbon atoms or a fused polycyclic ring having 3 to 12 carbon atoms, which may contain a chalcogen atom, a nitrogen atom, or a silicon atom, or it may be a benzene ring having 6 carbon atoms or a fused polycyclic ring having 3 to 8 carbon atoms, which may contain a nitrogen atom.

[0020] Also, Cy A Ring and Cy BThe ring may be a condensed polycyclic ring, and may be a fluorene ring, a dibenzofuran ring, a dibenzothiophene ring, a dibenzoselenophene ring, a dibenzoterolofen ring, or a spirofluorene ring, and may be a fluorene ring, a dibenzofuran ring, a dibenzothiophene ring, or a fluorene ring.

[0021] <R A and R B > In general formula (1), R A and R B These are Cy A Ring and Cy B This represents a group bonded to a carbon or heteroatom constituting a ring, and is independently selected from the group consisting of hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heterocyclic groups, substituted or unsubstituted amino groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryloxy groups, substituted or unsubstituted silyl groups, and cyano groups.

[0022] R A and R B This may be a hydrogen atom, a deuterium atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heterocyclic group having 4 to 12 carbon atoms, an amino group having 6 to 12 carbon atoms, or a cyano group, and may also be a hydrogen atom, an alkyl group having 1 to 7 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heterocyclic group having 4 to 12 carbon atoms, or a cyano group, and may also be a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a cyano group. Furthermore, R A and R B If the group is anything other than a hydrogen atom, it may be a methyl group, iso-propyl group, tert-butyl group, diarylamine group, phenyl group, phenyl group with an alkyl group as a substituent, or biphenyl group. Having these groups may help suppress aggregation of organic compounds and improve sublimation and solubility.

[0023] Adjacent R A Allies, adjacent RB They may be joined together to form a ring. As will be described later, Cy A Ring and Cy B The fused ring structure, in which atoms constituting a ring are bonded together, is ΔE ST It is not suitable for making it larger, R A and R B Similarly, the fused ring structure in which these are bonded also has ΔE ST It is not suitable for making it larger.

[0024] <n and m> In general formula (1), n ​​and m represent integers between 4 and 14, respectively.

[0025] <X1 and X2> In general formula (1), X1 and X2 are independently selected from the chalcogen atom group consisting of oxygen, sulfur, selenium, and tellurium atoms. X1 and X2 may also be sulfur, selenium, or tellurium atoms that exhibit the heavy atom effect, and can be either a sulfur atom or a tellurium atom.

[0026] <Y1 and Y2> In general formula (1), Y1 and Y2 are independently selected from oxygen atoms and sulfur atoms, respectively. Y1 and Y2 may also be oxygen atoms.

[0027] The organic compound according to this embodiment may be a compound represented by the following formula (2) or (3).

[0028]

[0029] <Z1 and Z2> In general formula (3), Z1 and Z2 are each independently selected from the group consisting of O, S, Se, Te, CR'R'', NR', and SiR'R''. R' and R'' are each independently selected from the group consisting of substituted or unsubstituted alkyl groups and substituted or unsubstituted aryl groups. R' and R'' may be substituted or unsubstituted alkyl groups. R' and R'' may be alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 18 carbon atoms, alkyl groups having 1 to 7 carbon atoms, aryl groups having 6 to 12 carbon atoms, alkyl groups having 1 to 4 carbon atoms, and aryl groups having 6 to 12 carbon atoms. Furthermore, R' and R'' may be methyl groups, iso-propyl groups, tert-butyl groups, phenyl groups, phenyl groups having an alkyl group as a substituent, or biphenyl groups.

[0030] In general formula (2), R A , R B At least one of them may be an alkyl group having 1 to 6 carbon atoms, or an aryl group having 5 to 7 carbon atoms. Also, in general formula (3), (R A ) 4, (R B R shown in )4 A , R B It is also possible that all of them are hydrogen atoms.

[0031] In this specification, halogen atoms include, but are not limited to, fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0032] Examples of chalcogen atoms include, but are not limited to, oxygen atoms, sulfur atoms, selenium atoms, and tellurium atoms.

[0033] The alkyl group may have 1 to 40 carbon atoms, 1 to 20 carbon atoms, or 1 to 10 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.

[0034] The aryl group may have 6 to 20 carbon atoms, 6 to 18 carbon atoms, or 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.

[0035] The heterocyclic group may have 3 to 24 carbon atoms, 3 to 18 carbon atoms, or 3 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.

[0036] 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.

[0037] The alkoxy group may have 1 to 40 carbon atoms, 1 to 20 carbon atoms, or 1 to 10 carbon atoms. Specifically, examples include, but are not limited to, methoxy groups, ethoxy groups, propoxy groups, 2-ethyl-octyloxy groups, and benzyloxy groups.

[0038] Examples of aryloxy groups include, but are not limited to, phenoxy groups.

[0039] Examples of heteroaryloxy groups include, but are not limited to, thienyloxy groups.

[0040] Examples of silyl groups include, but are not limited to, trimethylsilyl and triphenylsilyl groups.

[0041] Examples of substituents that may further be present include, but are not limited to, alkyl groups, aryl groups, heterocyclic groups, amino groups, alkoxy groups, aryloxy groups, heteroaryloxy groups, and silyl groups, halogen atoms such as fluorine, chlorine, bromine, and iodine; alkyl groups such as methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, and tert-butyl groups; alkoxy groups such as methoxy groups, ethoxy groups, and propoxy groups; amino groups such as dimethylamino groups, diethylamino groups, dibenzylamino groups, diphenylamino groups, and ditolylamino groups; aryloxy groups such as phenoxy groups; aryl groups such as phenyl groups and biphenyl groups; heterocyclic groups such as pyridyl groups and pyrrolyl groups; and cyano groups.

[0042] <Features> The organic compound of this embodiment has a smaller ΔE ST This shows that the organic compound of this embodiment is Δ EST The calculated value of may be 0.42 eV or less, or 0.40 eV or less. Here, a small ΔE ST I will explain the advantages of demonstrating this.

[0043] When organic compounds are electrically excited, such as in organic EL devices, it is known that singlet excited states and triplet excited states are generated in a ratio of 1:3 (25%:75%). Emission from the singlet excited state is observed as fluorescence, and emission from the triplet excited state is observed as phosphorescence. However, phosphorescence is not usually observed at room temperature, so the internal quantum efficiency of fluorescent materials remains at 25%. As mentioned above, TADF materials undergo reverse intersystem crossing from the triplet excited state to the singlet excited state, and emit fluorescence when returning from the singlet excited state to the ground state, so theoretically, 100% of excitons can contribute to emission. However, the triplet excited state has a longer exciton lifetime than the singlet excited state, and its high exciton density can cause triplet-triplet annihilation and triplet-polaron annihilation, leading to a decrease in luminescence efficiency and a shortened operating lifetime. Therefore, in TADF materials, it is considered important that reverse intersystem crossing from the triplet excited state to the singlet excited state occurs more quickly. This inverse interterm velocity constant (k RISC ) is expressed by the following formula (A).

[0044]

[0045] Here, k B is the Boltzmann constant, T is the temperature, H-bar is the Dirac constant, and <S1|HSO|T1> represents the spin-orbit coupling (SOC). λ is the Marcus reorientation energy, and assuming that λ does not differ significantly across compounds and the temperature T is constant, k RISC It is proportional to the square of the SOC.

[0046] That is, ΔE is the difference between the singlet excited state and the triplet excited state. ST The smaller k RISC It will become larger. Also, if SOC is large, k RISC The value increases, making reverse interterm crossing more likely. RISC A larger value is suitable because it increases the number of excitons contributing to light emission, and it is suitable because it can suppress the decrease in luminescence efficiency and shortening of the operating life due to triplet-triplet annihilation and triplet-polaron annihilation.

[0047] The organic compounds used in this embodiment are described below.

[0048] ΔE ST Quantum chemical calculations can be used when providing organic compounds with a small SOC (State of Core) or a large SOC (State of Core). Quantum chemical calculations are a computational chemistry approach that predicts molecular properties based on quantum mechanics.

[0049] ΔE between each energy level ST The functional is PBE1PBE, and the basis sets are 6-31g. * A structural optimization calculation is performed to determine the most stable structure of the ground state S0 using a density functional theory. Then, the excitation energy E from S0 to S1 is determined for the most stable structure of S0 using the aforementioned functional and basis function time-dependent density functional theory. S1 Excitation energy E from S0 to T1 T1 Excitation energy E from S0 to T2 T2 Excitation energy E from S0 to T3 T3 Excitation energy E from S0 to T4 T4 We find ΔE for T1.ST is E S1 - E T1 , ΔE with respect to T2 ST is E S1 - E T2 , ΔE with respect to T3 ST is E S1 - E T3 , ΔE with respect to T4 ST is E S1 - E T4 can be obtained by. As the basis function, 6 - 31g *In the case of a molecule containing an element that cannot be used, DGDZVP is used for the corresponding molecule. As calculation software for density functional and time-dependent density functional methods, for example, Gaussian 16, Revision C.01 (Gaussian 16, Revision C.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. V. Marenich, J. Bloino, B. G. Janesko, R. Gompertz, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasagawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery, Jr., J. E. Peralta, F. Oglialoro, M. J. Bearpark, J. J. Heyd, E. N. Brothers, K. N. Kudin, V. N. Staroverov, T. A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. P. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2019.) can be used.

[0050] S1 and Tn The calculation of the SOC between levels (n = 1, 2, 3, 4) is performed using the aforementioned time-dependent density functional method, as described in Non-Patent Document 1 below. S1 and E Tn Casida-type wave function Ψ using the inter-configuration interaction coefficient output during the calculation. S1 and Ψ Tn And, the effective charge approximation Breit-Pauli spin-orbit interaction Hamiltonian H eff SOC It is calculated using [this method]. For example, PySOC can be used as software to calculate the SOC.

[0051] <Non-Patent Document 1> Evaluation of Spin-Orbit Couplings with Linear-Response Time-Dependent Density Functional Methods Xing Gao, Shuming Bai, Daniele Fazzi, Thomas Niehaus, Mario Barbatti, and Walter Thiel J. Chem. Theory Comput. , 2017, 13(2), pp515-524

[0052] In this specification, the HOMO energy level and LUMO energy level can be calculated using the ionization potential and band gap.

[0053] 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 depositing the compound onto 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 deposited onto a substrate such as glass, and the band gap can be measured by irradiating the deposited film with excitation light. The measurement can be performed by measuring the absorption edge of the absorption spectrum where the deposited film absorbs the excitation light.

[0054] LUMO can be calculated using the energy levels, band gap, and ionization potential. Subtracting the ionization potential from the band gap allows for the estimation of the LUMO energy level. 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 measurements are 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.

[0055] Example compound 1 is a compound in general formula (1) that contains Cy A Ring and Cy B The ring is a benzene ring (an aryl ring with 6 carbon atoms), n and m are 4, R A and R B One of each is a methyl group, three are hydrogen atoms, R C X1 and X2 are hydrogen atoms, Y1 and Y2 are oxygen atoms, R 11 ~R 16 , R 21 ~R 26 It is a compound in which all atoms are hydrogen atoms.

[0056]

[0057] Here, the singlet excited state (S1) and triplet excited state (T1) of compounds A and B described in Patent Documents 1 and 2, and example compound 1 were calculated by quantum chemical calculations. The results are shown in Table 1.

[0058]

[0059]

[0060] As shown in Table 1, the ΔE of compound A described in Patent Document 1 ST While the ΔE of example compound 1 is 0.48 eV, ST 0.41 eV, and ΔE STIt can be seen that example compound 1 is smaller than compound A. Compound B described in Patent Document 2 has a similar skeleton to the compound of this embodiment, but Cy A Rings corresponding to rings and Cy B It has a fused ring structure in which the carbon atoms constituting the ring are bonded to each other, ΔE ST The value was 0.54 eV, which is higher than that of example compound 1. From this, Cy A Ring and Cy B The fused ring structure, in which atoms constituting a ring are bonded together, is ΔE ST To make it larger, Cy A Ring and Cy B The atoms that make up the ring do not necessarily have to be bonded together to form a fused ring.

[0061] Comparing example compound 1 and compound A, it was found that the difference lies in the presence or absence of HOMO / LUMO orbital distributions on the chalcogen atoms corresponding to X1 and X2 in general formula (1). Figure 1 shows the HOMO / LUMO orbital distributions of compound A, compound C, and example compound 1. In compound A, the bonding positions of the chalcogen atoms corresponding to X1 and X2 differ from those of example compound 1. As shown in Figure 1, in compound A, HOMO and LUMO orbitals are not distributed on the chalcogen atoms corresponding to the positions of X1 and X2 in general formula (1). In contrast, in example compound 1, HOMO and LUMO orbitals are distributed on the chalcogen atoms indicated by X1 and X2 in general formula (1), and this is ΔE ST We believe this is producing an effect that reduces the ΔE due to the heavy atom effect. For this reason, when X1 and X2 are S, Se, and Te, the ΔE due to the heavy atom effect is ST Because it is expected to have a narrowing effect, it is a suitable organic compound.

[0062] Furthermore, the bonding positions of the chalcogen atoms corresponding to X1 and X2 in compound C differ from those of compound A and example compound 1. As shown in Figure 1, compound C, like compound A, does not have HOMO and LUMO orbitals distributed on the chalcogen atoms corresponding to X1 and X2. For this reason, chalcogen atoms may be contained at the bonding positions of X1 and X2 represented by general formula (1).

[0063]

[0064] Furthermore, it was found that the compound of this embodiment also exhibits the effect of increasing the SOC. In particular, in TADF materials, it is known that higher-order triplet excited states of T2 or higher function as intermediate transition states during reverse intersystem crossing to singlet excited states, and therefore the SOC in the higher-order triplet excited state is <S1 | Hso | T n The value of 〉 may increase. Perform quantum chemical calculations using the method described above, and SOC; 〈S1|Hso|T n >The maximum values ​​were calculated. As a result, compound A had a value of 0.42, compound C had a value of 0.21, and example compound 1 had a value of 0.97, confirming that including chalcogen atoms at the bonding positions of X1 and X2 in general formula (1) significantly increases the SOC. At this time, the SOC may be 0.5 or higher, 0.8 or higher, or 0.9 or higher. In this embodiment, organic compounds with a large SOC are more prone to reverse intersystem crossing, which shortens the time that excitons remain at T1, and thus reduces the degradation of the light-emitting layer due to excitons remaining at T1. Therefore, organic light-emitting devices using the organic compounds of this embodiment as the light-emitting layer are expected to have excellent durability. Furthermore, it is thought that using the organic compounds of this embodiment as the light-emitting layer can reduce quenching from T1. Therefore, organic light-emitting devices using the organic compounds of this embodiment as the light-emitting layer are expected to have excellent luminous efficiency.

[0065] Using the same method as described above, the singlet excited state (S1) and triplet excited state (T1) were calculated for example compounds 2 to 21 and compounds D and E. The results are shown in Table 2.

[0066]

[0067]

[0068]

[0069] The difference between example compound 2 and example compound 1 is R A and R B Of each, two are methyl groups and two are hydrogen atoms, R C The key point is that it is a methyl group. ΔE of example compound 2ST The voltage was 0.41 eV, which is equivalent to that of example compound 1.

[0070] Exemplary compounds 2 to 4 and exemplary compound 11 differ in that X1 and X2 are O, S, Se, and Te, respectively. Their ΔE ST These values ​​were 0.41 eV, 0.39 eV, 0.38 eV, and 0.35 eV, respectively.

[0071] The difference between example compound 5 and example compound 3 is R A and R B The key difference is that one of each is a phenyl group and three are hydrogen atoms. ΔE of example compound 5 ST The value was 0.39 eV. The difference between example compound 6 and example compound 3 is that Cy A and Cy B is a dimethylfluorene ring, and R A and R B The key point is that all of them are hydrogen atoms. ΔE of example compound 6 ST The value was 0.41 eV. The difference between example compounds 7 and 8 and example compound 3 is R C However, the key difference lies in the fact that they are a mesityl group and a pyridyl group, respectively. ΔE of example compounds 7 and 8 ST The ΔE of both was 0.38 eV. The difference between example compound 9 and example compound 3 is that Y1 and Y2 are sulfur atoms. ST The value was 0.40 eV. The difference between example compound 10 and example compound 3 is R A and R B The key difference is that one of each is a tert-butyl group, and three are hydrogen atoms. ΔE of example compound 10 ST The voltage was 0.39 eV. C For example compounds 12 to 21 in which is an aryl group, ΔE ST The voltage was 0.4 eV or less.

[0072] These results show that in all compounds, the ΔE was equal to or less than that of example compound 1. ST It was found that this indicates...

[0073] Figure 2 shows the HOMO / LUMO orbital distributions of compound D, compound E, and example compound 10. Compound D has different binding positions for chalcogen atoms corresponding to X1 and X2 compared to example compound 10. Compound E has different chalcogen atoms corresponding to X1 and X2 compared to compound D. As shown in Figure 2, compound D and compound E do not have HOMO / LUMO orbitals distributed around the chalcogen atoms corresponding to X1 and X2. Furthermore, the ΔE of compound D and compound E... ST The values ​​were 0.46 eV and 0.47 eV, respectively, which were higher than those of example compound 10.

[0074] <Specific Examples> The following are examples of specific structural formulas of organic compounds according to this embodiment. However, the organic compounds according to this embodiment are not limited to these.

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106] <Example of a compound> The organic compound according to this embodiment may be a compound represented by the following general formula (4), or a compound represented by the following general formula (5). Compounds represented by general formulas (4) to (5) can be used in the light-emitting layer. From the viewpoint of synthesis, the organic compound for the light-emitting layer is more preferably the compound represented by general formula (5).

[0107]

[0108] In general formulas (4) to (5), R 11 ~R 16 , R 21 ~R 26 , R 31 ~R 34 , R 41 ~R 44Each of these is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aryl group. c R is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aryl group. In general formula (5), R 31 , R 34 , R 41 , R 44 R may be a hydrogen atom, c This may be selected from the group consisting of substituted or unsubstituted alkyl groups and substituted or unsubstituted aryl groups. Specifically, the compounds represented by general formulas (4) to (5) may be the following compounds.

[0109]

[0110]

[0111]

[0112]

[0113] Furthermore, the organic compounds of this embodiment, particularly those represented by general formulas (4) to (5), may be used together with the compounds represented by general formulas (6) to (8) below. In other words, the light-emitting layer according to this embodiment may include the organic compounds of this embodiment, particularly those represented by general formulas (4) to (5), and any of the organic compounds represented by general formulas (6) to (8). Also, any of the organic compounds represented by general formulas (6) to (8) may be used as a host material for the light-emitting layer.

[0114]

[0115] In general formulas (6) to (8), Rs to Ru and Rw are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a substituted or unsubstituted silyl group. Rv and Rx are each independently selected from a substituted or unsubstituted carbazole group. Y is a nitrogen atom or a carbon atom having a hydrogen atom. Specific examples of the organic compound represented by any of general formulas (6) to (8) include, but are not limited to, the following compounds.

[0116]

[0117] (2) Organic light-emitting device Next, the organic light-emitting device according to the present embodiment will be described. The organic light-emitting device according to the present embodiment has a first electrode, a second electrode, and an organic compound layer disposed between these electrodes. One of the first electrode and the second electrode is an anode and the other is a cathode. In the organic light-emitting device according to the present embodiment, the organic compound layer may be a single layer or a laminate composed of a plurality of layers as long as it has a light-emitting layer. The organic compound according to the present embodiment may be included in the organic compound layer or may be included in the light-emitting layer. Here, when the organic compound layer is a laminate composed of a plurality of layers, the organic compound layer may have, in addition to the light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole / exciton blocking layer, an electron transport layer, an electron injection layer, and the like. The light-emitting layer may be a single layer or a laminate composed of a plurality of layers. When the light-emitting layer has a plurality of 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 the LUMO energy level of the hole transport layer, and the LUMO energy level of the charge generation layer may be lower than the HOMO (highest occupied molecular orbital) energy level of the hole transport layer. Here, the HOMO energy level and the LUMO energy level of the organic compound layer may be the HOMO energy level and the LUMO energy level of the organic compound having the largest mass ratio in the organic compound layer.

[0118] 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.

[0119] In this specification, the HOMO energy levels and LUMO energy levels can be calculated using molecular orbital calculations. These calculations are performed using density functional theory (DFT), with the functional being B3LYP and the basis set being 6-31G. *It may be performed using, etc. Note that the molecular orbital calculation can be performed, for example, using Gaussian09 (Gaussian09, Revision C.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasagawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gompertz, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2010.).

[0120] In an organic light-emitting element according to one embodiment of the present invention, if the organic compound according to this embodiment is included in the light-emitting layer, the light-emitting layer may consist only of the organic compound according to this embodiment, or it may consist of the organic compound according to this embodiment and other compounds. Here, if the light-emitting layer consists of the organic compound according to this embodiment and other compounds, the organic compound according to this embodiment may be used as a host material 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.

[0121] 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 organic compound according to this embodiment may be a guest material, an assist material, or a host material. In this case, the organic light-emitting device according to this embodiment may satisfy S1(H) > S1(D) or S1(H) > S1(A) > S1(D). By satisfying the above relationship with respect to the lowest singlet excitation energy of the compound included in the organic light-emitting device according to this embodiment, excitons can be efficiently transferred to the guest material, resulting in an organic light-emitting device with superior luminescence efficiency.

[0122] When the organic compound according to this embodiment is used in the light-emitting layer, the concentration of the organic compound according to this embodiment may be 0.01% by mass or more and 99% by mass or less relative to the entire light-emitting layer. When the light-emitting layer is composed of the first compound and the organic compound according to this embodiment, the concentration of the organic compound according to this embodiment may be 0.01% by mass or more and 50% by mass or less, or 10% by mass or more and 50% by mass or less, relative to the entire light-emitting layer. When the light-emitting layer is composed of the first compound, the second compound and the organic compound according to this embodiment, the concentration of the organic compound according to this embodiment may be 1% by mass or more and 50% by mass or less, or 10% by mass or more and 50% by mass or less.

[0123] The inventors conducted various studies and found that when the organic compound according to this embodiment is used as a host, assist, or guest for the light-emitting layer, and particularly as a guest for the light-emitting layer, it exhibits excellent luminous efficiency and device operating life. ST We have found that this material is small in size. This light-emitting layer may be a single layer or a multi-layer layer, and it is also possible to mix it with the light-emitting color of this embodiment by including a light-emitting material having another light-emitting color. A multi-layer layer means that one light-emitting layer and another light-emitting layer are stacked on top of each other. In this case, the light-emitting color of the organic light-emitting element may be blue, green, red, white, or an intermediate color. In the case of white, it emits light in combination with blue, green, red, or an intermediate color. Furthermore, the film is formed by vapor deposition or coating. Details of this will be explained in detail in the examples described later.

[0124] The organic compound according to this embodiment 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 emission color of the organic light-emitting device is not limited to a single color. More specifically, it may be white light emission or an intermediate color.

[0125] <Other Compounds> In addition to the organic compounds according to this embodiment, 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.

[0126] The hole-injection transport material may be a material with high hole mobility to facilitate hole injection from the anode and transport the injected holes to the light-emitting layer. It may also be a material with a high glass transition temperature to suppress crystallization of organic compounds within 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. Furthermore, the above-mentioned hole-injection transport material may also be used in the electron-blocking layer. Additionally, when the hole-injection layer is fabricated by a coating method, a mixture of polyethylenedioxythiophene and polystyrene sulfonic acid (PEDOT:PSS), 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.

[0127]

[0128]

[0129] Among the hole-injection transport 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, HT22 to HT28 may be used in the organic compound layer adjacent to HT16. Hole-transport 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.

[0130] Guest materials primarily involved in luminescence include donor-acceptor type organic compounds, boron-containing complexes, indocarbazole fused ring compounds, fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, organoaluminum complexes such as tris(8-quinolinolate)aluminum, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, and polymer derivatives such as poly(phenylenevinylene) derivatives, poly(fluorene) derivatives, and poly(phenylene) derivatives. Furthermore, when creating a luminescent layer by coating, polymer compounds with luminescence properties are mainly used. This is because polymer compounds tend to exhibit high glass transition temperatures, making them less prone to crystallization compared to low-molecular-weight systems. Specific materials used include polymer compounds such as polyphenylene vinylene (PPV), polyfluorene (PF), polyvinylcarbazole (PVK), and their derivatives. Specific examples of compounds used as luminescent materials are shown below, but are not limited to these.

[0131]

[0132]

[0133]

[0134] 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.

[0135]

[0136]

[0137] [Assist Dopant] The organic compound of this embodiment may also be used together with the compounds represented by the following general formulas (9-1) to (10-2). In other words, the light-emitting layer according to this embodiment may contain the organic compound of this embodiment and an organic compound represented by any of the general formulas (9-1) to (10-2). Furthermore, the organic compound represented by any of the general formulas (9-1) to (10-2) may be used as an assist dopant material for the light-emitting layer.

[0138]

[0139]

[0140] In general formulas (9-1) to (10-2), R 11 ~R 13 , R 31 and R 32 The '' represents a substituent, which can be independently selected from a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a cyano group, and a silyl group.

[0141] n is an integer from 0 to 2, n' and n'' are integers from 0 to 4, and m and m' are integers from 0 to 5. If n, n', n'', m, and m' are 2 or more, multiple R 11 ~R 13 , R 31 and R 32 The individuals may be the same or different.

[0142] R 21 ~R 24 R is independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a cyano group, and a silyl group. 21 ~R24 At least one of these may be a substituted or unsubstituted alkyl group.

[0143] X represents oxygen, sulfur, selenium, and tellurium atoms.

[0144] Examples of these representative compounds include, but are not limited to, the following:

[0145]

[0146]

[0147]

[0148]

[0149] 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 may also be used in the hole-blocking layer. Specific examples of compounds used as electron-transporting materials are shown below, but of course, the material is not limited to these.

[0150]

[0151]

[0152] Electron injection 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. They can also be used in combination with the above-mentioned electron transport materials.

[0153] <Configuration of Organic Light-Emitting Device> The components constituting the organic light-emitting device of this embodiment will be described below. The organic light-emitting device is provided by forming an insulating layer, a first electrode, an organic compound layer, and a second electrode on a substrate. A protective layer, a color filter, a microlens, etc., may be provided on the second electrode. 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.

[0154] [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.

[0155] [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.

[0156] 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.

[0157] 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.

[0158] 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.

[0159] 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. Silver may be used, and a silver alloy may be used 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.

[0160] 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 methods such as DC and AC sputtering are suitable because they provide good film coverage and make it easy to lower resistance.

[0161] [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.

[0162] 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.

[0163] 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.).

[0164] 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.

[0165] 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.

[0166] 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.

[0167] [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.

[0168] [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.

[0169] [Planarizing Layer] A planarizing layer may be provided between the color filter and the protective layer. The planarizing layer is provided to reduce the unevenness of the layer below. It may also be called a material resin layer without limiting its purpose. The planarizing layer may be composed of an organic compound, and may be low molecular weight or high molecular weight, but can be high molecular weight.

[0170] 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.

[0171] [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.

[0172] 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.

[0173] [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.

[0174] [Pixel Circuit] An organic light-emitting device having an organic light-emitting element may have a pixel circuit connected to the organic light-emitting element. The pixel circuit may be an active-matrix type that 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.

[0175] The organic 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.

[0176] The slope of the current-voltage characteristic of the transistors constituting the pixel circuit may be smaller than the slope of the current-voltage characteristic of the transistors constituting the display control circuit. The slope of the current-voltage characteristic can be measured using the so-called Vg-Ig characteristic. The transistors constituting the pixel circuit are transistors connected to light-emitting elements, such as the first light-emitting element.

[0177] [Pixels] An organic light-emitting device having organic light-emitting elements has a plurality of pixels. Each pixel has sub-pixels that emit light of a different color from the others. The sub-pixels may each have, for example, RGB emission colors.

[0178] 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.

[0179] The distance between subpixels may be 10 μm or less, specifically 8 μm, 7.4 μm, or 6.4 μm.

[0180] 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.

[0181] <Applications of Organic Light-Emitting Devices> The organic light-emitting device according to this embodiment can be used as a component of display devices and lighting devices. Other applications include exposure light sources for electrophotographic image forming apparatuses, backlights for liquid crystal display devices, and light-emitting devices with a color filter in a white light source.

[0182] The display device may also be an image information processing device having an image input unit for inputting image information from an area CCD, linear CCD, memory card, etc., an information processing unit for processing the input information, and for displaying the input image on a display unit. The display device may have a plurality of pixels, and at least one of the plurality of pixels may have the organic light-emitting element of this embodiment and an active element such as a transistor connected to the organic light-emitting element. In this case, the substrate may be a semiconductor substrate such as silicon, and the transistor may be a MOSFET formed on the substrate. The image display device has an input unit for inputting image information and a display unit for outputting an image, and the display unit has the display device of this embodiment. Alternatively, the image display device may have a display unit having the organic light-emitting element of this embodiment and a housing on which the display unit is provided.

[0183] 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.

[0184] Next, the display device according to this embodiment will be described with reference to the drawings.

[0185] Figure 3 is a schematic cross-sectional view showing an example of a display device having an organic light-emitting element and a transistor connected to this organic light-emitting element. The transistor is an example of an active element. The transistor may also be a thin-film transistor (TFT).

[0186] Figure 3A is a schematic cross-sectional view of 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 10 has a reflective electrode which is a first electrode 2 on an interlayer insulating layer 1, an insulating layer 3 covering the end of the first electrode 2, an organic compound layer 4 covering the first electrode 2 and the insulating layer 3, a transparent electrode which is a first electrode 5, a protective layer 6, and a color filter 7.

[0187] The interlayer insulating layer 1 may have transistors and capacitive elements placed in the layer below or inside it. The transistor and the first electrode 2 may be electrically connected via a contact hole or the like (not shown).

[0188] The insulating layer 3 is also called a bank or pixel isolation layer. It covers the end of the first electrode 2 and is arranged to surround the first electrode 2. The portion not covered by the insulating layer 3 is in contact with the organic compound layer 4 and becomes the light-emitting region.

[0189] The organic compound layer 4 includes a hole injection layer 41, a hole transport layer 42, a light-emitting layer 43, a hole blocking layer 44, and an electron transport layer 45.

[0190] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0191] The protective layer 6 reduces the penetration of moisture into the organic compound layer 4. Although the protective layer 6 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.

[0192] The color filter 7 is classified into 7R, 7G, and 7B according to its color. The color filter 7 may be formed on a planarization film (not shown). The color filter 7 may also have a resin protective layer (not shown). Alternatively, the color filter 7 may be formed on a protective layer 6, or it may be bonded to an opposing substrate such as a glass substrate after being placed on it.

[0193] The display device 100 in Figure 3B includes an organic light-emitting element 26 and a TFT 18, which is an example of a transistor. A substrate 11 made of glass, silicon, or the like is provided, with an insulating layer 12 on top of it. An active element such as the TFT 18 is placed on the insulating layer 12, and the active element has a gate electrode 13, a gate insulating film 14, and a semiconductor layer 15. The TFT 18 has a drain electrode 16 and a source electrode 17. An insulating film 19 is provided on top of the TFT 18. The anode 21 and the source electrode 17 constituting the organic light-emitting element 26 are connected via a contact hole 20 provided in the insulating film 19.

[0194] Note that the method of electrical connection between the electrodes (anode 21, cathode 23) included in the organic light-emitting element 26 and the electrodes (source electrode 17, drain electrode 16) included in the TFT 18 is not limited to the configuration shown in Figure 3B. In other words, it is sufficient if either the anode 21 or the cathode 23 is electrically connected to either the source electrode 17 or the drain electrode 16 of the TFT 18. TFT refers to a thin-film transistor.

[0195] In the display device 100 shown in Figure 3B, the organic compound layer 22 is illustrated 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 26.

[0196] In the display device 100 shown in Figure 3B, a transistor is used as the switching element, but other switching elements such as MIM elements may be used instead.

[0197] Furthermore, the transistor used in the display device 100 in Figure 3B is not limited to a thin-film transistor having an active layer on the insulating surface of the substrate, but may also be a transistor using a single-crystal silicon wafer. Examples of the active layer include non-single-crystal silicon such as single-crystal silicon, amorphous silicon, and microcrystalline silicon, and non-single-crystal oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Thin-film transistors are also called TFT elements.

[0198] The transistors included in the display device 100 in Figure 3B 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.

[0199] 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, the organic light-emitting element may be provided on a Si substrate.

[0200] Figure 4 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.

[0201] 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.

[0202] 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.

[0203] The display device according to this embodiment may be used in the display unit of an imaging device having an optical unit with multiple lenses and an image sensor that receives light that has passed through the optical unit. The imaging device may have a display unit that displays information acquired by the image sensor. Furthermore, the display unit may be a display unit exposed to the outside of the imaging device or a display unit located inside the viewfinder. The imaging device may be a digital camera or a digital video camera.

[0204] Figure 5A 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 obstruction, etc.

[0205] Since the optimal timing for imaging is very short, it is best to display the information as quickly as possible. Therefore, a display device using the organic light-emitting element according to this embodiment may be used, because organic light-emitting elements have a fast response speed.

[0206] 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.

[0207] Figure 5B 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 1202 may also be a biometric recognition unit that recognizes a fingerprint to unlock or otherwise perform actions. An electronic device having a communication unit can also be called a communication device. The electronic device 1200 may further have a camera function by including a lens and an image sensor. Images captured by the camera function are displayed on the display unit 1201. Examples of the electronic device 1200 include smartphones and laptop computers.

[0208] Figure 6 is a schematic diagram showing an example of a display device according to this embodiment. Figure 6A is a display device such as a television monitor or a PC monitor. The display device 1300 has a housing (frame) 1301 and a display unit 1302. The display unit 1302 may use an organic light-emitting element according to this embodiment. 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 6A. The lower edge of the housing 1301 may also serve as the base. In addition, the housing 1301 and the display unit 1302 may be curved. The radius of curvature may be 5000 mm or more and 6000 mm or less.

[0209] Figure 6B is a schematic diagram showing another example of a display device according to this embodiment. The display device 1310 in Figure 6B 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.

[0210] Figure 7A 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 (optical filter) 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.

[0211] 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.

[0212] 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.

[0213] Figure 7B 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 1501 may illuminate when the brakes are applied or the like. The body 1503 may also be called the machine body. The automobile 1500 may have a window 1502 attached to the body 1503.

[0214] The tail lamp 1501 may have an organic light-emitting element according to this embodiment. The tail lamp 1501 may have a protective member to protect the light source. The protective member has a reasonably high strength and is transparent, so the material is not limited, but it may be made of polycarbonate or the like. A frangic acid derivative, an acrylonitrile derivative, or the like may be mixed with the polycarbonate.

[0215] The window 1502 may be a transparent display if it is not a window for checking the front and rear of the vehicle. The transparent display may have an organic light-emitting element according to this embodiment. In this case, the constituent materials such as electrodes of the organic light-emitting element according to this embodiment are made of transparent material.

[0216] The moving body according to this embodiment includes a driving force generating unit that generates a driving force mainly used for the movement of the moving body, and one or both of the rotating bodies mainly used for the movement of the moving body. The driving force generating unit may be an engine, a motor, etc. The rotating body may be a tire, a wheel, a ship's propeller, an aircraft's propeller, etc.

[0217] The mobile body according to this embodiment may specifically be a bicycle, automobile, train, ship, aircraft, drone, etc. The mobile body may have a body and a light fixture installed on the body. The light fixture may emit light to determine the position of the body. The light fixture may have an organic light-emitting element according to this embodiment.

[0218] Referring to Figure 8, 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. The wearable device may have a display unit having the organic light-emitting element of this embodiment, an optical system for focusing the light from the display unit, and a control device for controlling the display of the display unit.

[0219] Figure 8A is a schematic diagram showing an example of a wearable device according to this embodiment. Using Figure 8A, we will explain a pair of glasses 1600 (smart glasses) according to one application example. The glasses 1600 have a display unit on the back side of the lens 1601. The display unit may have an organic light-emitting element according to this embodiment. Furthermore, an imaging device 1602 such as a CMOS sensor or SPAD may be provided on the front side of the lens 1601.

[0220] 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.

[0221] Figure 8B is a schematic diagram showing another example of a wearable device according to this embodiment. Using Figure 8B, we will describe a pair of glasses 1610 (smart glasses) according to one application example. The glasses 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 this embodiment. 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.

[0222] The control device 1612 may have a gaze detection unit that detects the wearer's gaze. Gaze detection may use infrared light. The infrared light emitter emits infrared light towards the eyeball of the user who is fixating on the displayed image. An imaging unit having a light-receiving element detects the reflected light from the eyeball from the emitted infrared light, thereby obtaining an image of the eyeball. By having a reduction means that reduces the light from the infrared light emitter to the display unit in a planar view, the deterioration of image quality is reduced.

[0223] 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. More specifically, gaze detection processing based on the pupil-corneal reflection method is performed. Using the pupil-corneal reflection method, the user's gaze is detected by producing a gaze vector representing the orientation (rotation angle) of the eyeball based on the pupil image and the Purkinje image included in the image of the eyeball.

[0224] 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. Specifically, the display device determines a first field of view area that the user is fixated on, and a second field of view area other than the first field of view area, based on the gaze information. 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. In the display area of ​​the display device, the display resolution of the first field of view area may be controlled to be higher than the display resolution of the second field of view area. In other words, the resolution of the second field of view area may be lower than that of the first field of view area.

[0225] 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.

[0226] AI may be used to determine the first field of view and the high-priority field of view. 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 contained in the display device, the imaging device, or an external device. If the external device contains the AI, it can be applied to smart glasses that further contain an imaging device for capturing images of the outside. The smart glasses can display the captured external information in real time.

[0227] Figure 9A 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 recording 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.

[0228] Figures 9B and 9C are diagrams showing the exposure light source 28, schematic diagrams showing how multiple light-emitting units 36 are arranged on a long substrate. Arrows 37 indicate the column direction in which the organic light-emitting elements are arranged. This column direction is the same as the direction of the axis of rotation of the photoreceptor 27. This direction can also be called the long axis direction of the photoreceptor 27. Figure 9B shows a configuration in which the light-emitting units 36 are arranged along the long axis direction of the photoreceptor 27. Figure 9C is a different configuration from Figure 9B, 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 9C can also be described as a grid pattern, a houndstooth pattern, or a checkerboard pattern.

[0229] 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.

[0230] (3) Ink Composition Next, the ink composition according to this embodiment will be described. The ink composition according to this embodiment contains at least one of the organic compounds according to this embodiment. By using the ink composition according to this embodiment, it is possible to produce a layer made of the organic compounds constituting the organic light-emitting element according to this embodiment, particularly the light-emitting layer, by a coating method, and relatively inexpensive large-area elements can be easily produced.

[0231] The ink composition according to this embodiment may contain a solvent for dissolving the organic compound according to this embodiment. Examples of solvents for dissolving the organic compound according to this embodiment include toluene, xylene, mesitylene, dioxane, methylnaphthalene, tetrahydrofuran, diglyme, 1,2-dichlorobenzene, and 1,2-dichloropropane. These solvents can be used individually or in combination of two or more. Among these, a solvent with a suitable evaporation rate, specifically one with a boiling point of about 70°C to 200°C, may be used in order to easily obtain a thin film with a uniform thickness.

[0232] Furthermore, 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.

[0233] The concentration of the organic compound in the ink composition according to this embodiment may be 0.05% by mass or more and 20% by mass or less, or 0.1% by mass or more and 5% by mass or less, based on the total composition.

[0234] The ink composition according to this embodiment can be formed by methods such as spin coating, bar coating, slit coating, inkjet, nozzle coating, casting, and gravure printing. The organic light-emitting element of this embodiment can be used to construct a display device such as a screen by forming the organic light-emitting element of this embodiment on electrodes formed on a pixel pattern.

[0235] The following describes some examples, but the present invention is not limited to these.

[0236] The organic compounds according to this embodiment can be synthesized, for example, by the following synthesis method. Below, the synthesis of exemplary compound 6 and exemplary compound 3 are shown as examples.

[0237] <Example 1 (Synthesis of Exemplary Compound 6)> <Synthesis of Intermediate 1-1>

[0238] Under a nitrogen atmosphere, dibenzo[b,d]thiophen-1-ol (5.0 g, 24.9 mmol), cesium carbonate (8.1 g, 24.9 mmol), and 5-Bromo-1,3-difluoro-2-methylbenzene (1.0 mL, 7.7 mmol) were suspended in 1-methyl-2-pyrrolidone (100 mL) and stirred at 170°C for 18 hours. After cooling, saturated brine and toluene were added to the reaction mixture, and the organic layer was separated. The organic layer was dried over sodium sulfate, and the filtrate was removed by vacuum distillation. Acetonitrile was added to the resulting residue, and the precipitated solid was filtered and washed with hexane to obtain intermediate 1-1 as a white solid (2.8 g, 4.9 mmol, 64%).

[0239] 1 H NMR (400MHz, CDCl3) δ (ppm): 2.33 (s, 3H), 6.85 (dd, J = 8.0, 0.6Hz, 2H), 7.00 (s, 2H), 7.41 (t, J = 8.0H, 2H), 7.45-7.52 (m, 4H) 2, 7.64 (dd, J=8.0, 0.6Hz, 2H), 7.88-7.91 (m, H), 8.59-8.60 (m, 2H)

[0240] <Synthesis of Intermediate 1-2>

[0241] ​Under a nitrogen atmosphere, intermediate 1-1 (1.20 g, 2.12 mmol), Bis(9,9-dimethyl-9H-fluoren-2-yl)amine (932 mg, 2.32 mmol), palladium acetate (6.3 mg, 0.030 mmol), tri-tert-butylphosphonium tetrafluoroborate (19.5 mg, 0.070 mmol), and sodium-tert-butoxide (413 mg, 4.29 mmol) were suspended in toluene (20 mL) and stirred at 100°C for 14 hours. After cooling, water and methylene chloride were added to the reaction mixture, and the organic layer was separated. The organic layer was dried over sodium sulfate, and the filtrate was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (Hexane:CH2Cl2=3:2, v / v), and the resulting solid was washed with hexane to obtain intermediates 1-2 as white solids (1.78 g, 2.00 mmol, 94%).

[0242] 1 H NMR (400MHz, CD2Cl2) δ (ppm): 1.30 (s, 12H), 2.25 (s, 3H), 6.78 (s, 2H), 6.88 (dd, J = 8.0, 0.72Hz, 2H), 7.02 (dd, J = 8.2, 2.1Hz, 2H), 7.20-7.29 (m, 6H), 7.3 5-7.39 (m, 4H), 7.47-7.50 (m, 6H), 7.52 (dd, J = 8.0, 0.8Hz, 2H), 7.58 (dd, J = 6.7, 0.8Hz, 2H), 7.85-7.87 (m, 2H), 8.66-8.69 (m, 2H). MS (MALDI-TOF): m / z calcd for C 61 H 45 NO2S2 887.289; found 887.384 ([M] + ).

[0243] <Synthesis of Exemplary Compound 6>

[0244] ​Under a nitrogen atmosphere, intermediates 1-2 (502 mg, 0.565 mmol) were suspended in 1,2,4-trichlorobenzene (15 mL). Boron triiodide (1.06 g, 2.70 mmol) was added to this suspension, and the mixture was stirred at 150°C for 23 hours. After cooling, saturated sodium sulfite aqueous solution and methylene chloride were added to the reaction mixture, and the organic layer was separated. The organic layer was dried over sodium sulfate, and the filtrate was concentrated under reduced pressure. Methanol was added to the resulting residue, and the precipitated solid was filtered off. Exemplary compound 6 was obtained as a yellow solid (119 mg, 0.132 mmol, 23%) by recrystallization of the solid from toluene-hexane.

[0245] 1 H NMR (400MHz, (CDCl2)2, 130°C) δ (ppm): 1.47 (s, 6H), 1.84 (s, 6H), 3.50 (s, 3H), 7.42 (dt, J = 7.2, 0.8Hz, 2H), 7.48-7.53 (m, 4H), 7.62 (td, J = 7.6, 0.8Hz, 2H), 7.82 (td , J=7.8, 1.2Hz, 2H), 8.02-8.05 (m, 4H), 8.08 (d, J=8.4Hz, 2H), 8.48 (s, 2H), 8.97 (d, J=8.0Hz, 2H), 9.17 (s, 2H), 9.54 (d, J=7.6Hz, 2H). MS (MALDI-TOF): m / z calcd for C 61 H 39 B2NO2S2 903.261; found 903.102 ([M] + ).

[0246] <Example 2 (Synthesis of Exemplary Compound 3)> <Synthesis of Intermediate 2-1>

[0247] ​Under a nitrogen atmosphere, intermediate 1-1 (2.50 g, 4.52 mmol), bis(3,4-dimethylphenyl)amine (1.12 g, 4.96 mmol), tris(dibenzylideneacetone)dipalladium (0) (44.8 mg, 0.049 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (45.8 mg, 0.096 mmol), and sodium tert-butoxide (886 mg, 9.22 mmol), synthesized in the same manner as in Example 1, were suspended in toluene (40 mL) and stirred at 100°C for 26 hours. After cooling, water and methylene chloride were added to the reaction mixture, and the organic layer was separated. The organic layer was dried over sodium sulfate, and the filtrate was concentrated under reduced pressure. Methanol was added to the resulting residue, and the precipitate was filtered. The filtered solid was dissolved in chloroform, activated carbon was added, and the mixture was stirred at room temperature for 30 minutes, followed by Celite filtration. The filtrate was concentrated under reduced pressure, and the resulting solid was washed with hexane to obtain intermediate 2-1 as a white solid (1.09 g, 1.53 mmol, 34%).

[0248] 1 H NMR (400MHz, CDCl3) δ (ppm) 2.10 (s, 6H), 2.11 (s, 3H), 2.14 (s, 6H), 6.67 (s, 2H), 6.78-6.8 (m, 4H), 6.89-6.94 (m, 4H), 7.35 ( t, J=8.0Hz, 2H), 7.45-7.47 (m, 4H), 7.51 (dd, J=8.8, 0.8Hz, 2H), 7.84-7.86 (m, 2H), 8.69-8.71 (m, 2H). MS (MALDI-TOF): m / z calcd for C 47 H 37 NO2S2 711.227; found 711.322 ([M] + ).

[0249] <Synthesis of Example Compound 3>

[0250] ​Under a nitrogen atmosphere, intermediate 2-1 (707 mg, 0.993 mmol) was suspended in o-dichlorobenzene (10 mL). Boron triiodide (1.97 g, 5.04 mmol) was added to this suspension and the mixture was stirred at 150°C for 21 hours. After cooling, diisopropylethylamine (4.0 mL) and methanol were added to the reaction mixture, and the precipitate was filtered. Exemplary compound (3) was obtained as a yellow solid (628 mg, 0.863 mmol, 87%) by heat washing of the filtered solid with chlorobenzene.

[0251] MS (MALDI-TOF): m / z calcd for C 47 H 31 B2NO2S2 727.198; found 727.004 ([M] + ). Anal. calcd for C 47 H 31 B2NO2S2 C, 77.60; H, 4.30; N, 1.93. Found: C, 77.56; H, 4.32; N, 1.83.

[0252] <Example 3 (Synthesis of Exemplary Compound 12)> <Synthesis of Intermediate 12a>

[0253] A solution of 2-bromo-5-chloro-1,3-difluorobenzene (0.51 g, 2.2 mmol), 3,5-di-tert-butylphenylboronic acid (0.61 g, 2.6 mmol), potassium carbonate (0.55 g, 4.0 mmol), and Pd(dppf)Cl2 (0.071 g, 0.097 mmol) in 1,4-dioxane (8 mL) and water (2 mL) was stirred at 100°C for 18 hours. The reaction solution was extracted with dichloromethane, the organic layer was dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation. The residue was purified by column chromatography (SiO2, eluent: hexane) followed by GPC (eluent: CHCl3) to obtain intermediate 12a as a colorless solid (yield 0.71 g, 2.1 mmol, 95%).

[0254] 1 H NMR (400MHz, CDCl3), δ (ppm): 7.50 (t, 1.6Hz, 1H), 7.28 (d, J = 1.6Hz, 2H), 7.05 (d, 3 J​HF =7.0Hz, H), 1.38(s, 18H).

[0255] <Synthesis of Intermediate 12b> A solution of dibenzo[b,d]thiophen-1-ol (0.72 g, 3.6 mmol) and tert-butoxypotassium (0.41 g, 3.6 mmol) in N-methyl-2-pyrrolidone (16 mL) was stirred at room temperature for 30 minutes. Intermediate 12a was added to this solution and stirred at 170°C for 22 hours. Water was added to the reaction mixture and extracted with toluene, and the organic layer was extracted with anhydrous sodium sulfate. After filtration, the mixture was concentrated, methanol was added to the residue to suspend it, and it was filtered. The residue was purified by column chromatography (SiO2, eluent:Hexane:CH2Cl2 = 4:1, v / v), washed with methanol, and intermediate 12b was obtained as a colorless solid (0.41 g, 0.60 mmol, 40%).

[0256] 1 H NMR (400MHz, CDCl3), δ (ppm): 8.37-8.35 (m, 2H), 7.89-7.76 (m, 2H), 7.52 (dd, J = 7.3, 0.7Hz, 2H), 7.41-7.31 (m, 6H), 7.13 (d, J=1.8Hz, 2H), 7.01 (s, 2H), 6.95-6.93 (m, 3H), 0.92 (s, 18H).

[0257] <Synthesis of Intermediate 12c> Intermediate 12b (0.25 g, 0.36 mmol) was mixed with bis(3,4-dimethylphenyl)amine (0.088 g, 0.39 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.011 g, 0.016 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (XPhos, 0.011 g, 0.022 mmol), and sodium tert-butoxide (0.069 g, 0.72 mmol) in toluene (5 mL) under reflux for 21 hours. Water was added to the reaction solution, extracted with dichloromethane, dried over anhydrous sodium sulfate, and the solvent was removed by distillation. The residue was purified by silica gel column chromatography (SiO2, eluent:Hexane:CH2Cl2 = 1:1, v / v), the solvent was removed, and the residue was washed with methanol to obtain intermediate 12c as a colorless solid (0.26 g, 0.30 mmol, 82%). ​

[0258] 1 H NMR (400MHz, CDCl3), δ (ppm): 8.83-8.36 (m, 2H), 7.73-7.71 (m, 2H), 7. 38 (dd, J=7.9, 0.8Hz, 2H), 7.36-7.27 (m, 6H), 7.03 (d, J=1.8Hz, 2H), 6. 99-6.96 (m, 4H), 6.91 (dd, J=8.0, 0.7Hz, 2H), 6.88 (dd, J=8.1, 2.2Hz, 2 H), 6.76 (t, J=1.8Hz, 1H), 6.75 (s, 2H), 2.16 (s, 6H), 2.14 (s, 6H), 0.78 (s, 18H)

[0259] <Synthesis of Exemplary Compound 12> A solution of intermediate 12c (0.41 g, 0.46 mmol) and boron triiodide (0.94 g, 2.4 mmol) in o-DCB (4 mL) was stirred at 150°C for 24 hours. N,N-diisopropylethylamine (2 mL) was added to the reaction solution, and the mixture was added to methanol. After filtering the resulting suspension, the residue was purified by silica gel column chromatography (SiO2, eluent:toluene), washed with acetonitrile at 80°C, and exemplary compound 12 was obtained as a yellow solid (0.22 g, 0.25 mmol, 55%).

[0260] 1 H NMR (400MHz, CDCl3), δ (ppm): 8.83 (dJ = 8.1Hz, 2H), 8.62 (s, 2H), 8.20 ( s, 2H), 8.06 (t, J = 1.8Hz, 1H), 7.94 (d, J = 8.1Hz, 2H), 7.83-7.81 (m, 2H) , 7.61 (d, J=1.8Hz, 2H), 7.41-7.39 (m, 2H), 7.36 (td, J=7.6, 1.1Hz, 2H) , 7.01 (td, J=7.6, 1.1Hz, 2H), 2.55 (s, 6H), 2.45 (s, 6H), 1.39 (s, 18H); MS (MALDI-TOF, positive): m / z 901.330 (M + , calcd for C 60 H 49 B2NO2S2 901.339).

[0261] <<Example 4 (Synthesis of Exemplary Compound 13)>> ​​

[0262] <Synthesis of dibenzo[b,d]selenophen-1-ol> 1-bromo-dibenzoselenophen was synthesized according to Chemical Communications (2023), 59(49), 7599-7602.

[0263] 1-bromodibenzoselenophen (6.45 g, 20.8 mmol) and KOH (3.51 g, 62.5 mmol) were placed in a 100 mL round-bottom flask, and the inside was purged with nitrogen. Then 13 mL of dioxane and 13 mL of distilled water were added, and nitrogen bubbling was performed for 15 minutes. After that, Pd2(dba)3 (0.38 g, 0.40 mmol) and t BuXPhos (0.71 g, 1.7 mmol) was added and refluxed at 110°C for 24 hours. After cooling to room temperature, the mixture was neutralized with hydrochloric acid and ammonium chloride, extracted with chloroform, and the extract was dried over magnesium sulfate. The crude product was recovered by concentration to dryness, and this was separated by column chromatography (hexane: CHCl3 = 10:1 to 0:1). The desired fraction was concentrated to obtain a white powder of dibenzo[b,d]selenophen-1-ol (Yield 3.55 g, 14.4 mmol, 69%).

[0264] <Synthesis of Exemplary Compound 13> Exemplary compound 13 was synthesized in the same manner as exemplary compound 12, using dibenzo[b,d]selenophen-1-ol instead of dibenzo[b,d]thiophen-1-ol.

[0265] <<Example 5 (Synthesis of Exemplary Compound 14)>> Exemplary compound 14 was synthesized using [1,1'-biphenyl]-2-ylboronic acid instead of 3,5-di-tert-butylphenylboronic acid, in the same manner as exemplary compound 12.

[0266] <<Example 6 (Synthesis of Exemplary Compound 15)>> Exemplary compound 15 was synthesized using dibenzo[b,d]selenophen-1-ol instead of dibenzo[b,d]thiophen-1-ol, in the same manner as exemplary compound 14.

[0267] <<Example 7 (Synthesis of Exemplary Compound 16)>> Instead of 3,5-di-tert-butylphenylboronic acid, (2-isopropylphenyl)boronic acid was used to synthesize example compound 16 in the same manner as example compound 12.

[0268] <<Example 8 (Synthesis of Exemplary Compound 17)>> Exemplary compound 17 was synthesized using (2,4,6-triisopropylphenyl)boronic acid instead of 3,5-di-tert-butylphenylboronic acid, in the same manner as exemplary compound 12.

[0269] <<Example 9 (Synthesis of Exemplary Compound 18)>> Exemplary compound 18 was synthesized using di([1,1'-bisphenyl]-4-yl)amine instead of bis(3,4-dimethylphenyl)amine, in the same manner as exemplary compound 12.

[0270] <<Example 10 (Synthesis of Exemplary Compound 19)>> Exemplary compound 19 was synthesized using di([1,1'-bisphenyl]-4-yl)amine instead of bis(3,4-dimethylphenyl)amine, in the same manner as exemplary compound 14.

[0271] <<Example 11 (Synthesis of Exemplary Compound 20)>> Exemplary compound 20 was synthesized using di([1,1'-bisphenyl]-4-yl)amine instead of bis(3,4-dimethylphenyl)amine, in the same manner as exemplary compound 16.

[0272] <<Example 12 (Synthesis of Exemplary Compound 21)>> Exemplary compound 21 was synthesized using di([1,1'-bisphenyl]-4-yl)amine instead of bis(3,4-dimethylphenyl)amine, in the same manner as exemplary compound 17.

[0273] <<Comparative Example 1 (Synthesis of Compound A)>> Compound A was synthesized in the same manner as in Example 1 and Example 2.

[0274]

[0275] Example 13 (ΔE ST(Calculation) >> Example compound 6, example compound 3, and compound A are each dissolved in toluene in 1.0 × 10 -5 The solution was dissolved at concentration M, bubbled in Ar for 5 minutes, and then the fluorescence emission spectrum was measured at room temperature (298 K). A tangent line was drawn to the rise of the short-wavelength side of the measured fluorescence spectrum, and the wavelength λ at the intersection of this tangent line and the horizontal axis was measured. F Determine the (nm) and the excited singlet energy level (eV) = 1239.85 / λ F The excited singlet energy level S1 (eV) was calculated from the given equation.

[0276] The similarly prepared samples were cooled to 77 K, and the phosphorescent emission spectra observed after the excitation light was cut off were measured. A tangent line was drawn to the rise of the short-wavelength side of the measured phosphorescent spectrum, and the wavelength λ at the intersection of this tangent line and the horizontal axis was measured. P Determine the (nm) and the excited triplet energy level (eV) = 1239.85 / λ P The excited triplet energy level T1 (eV) was calculated from the given equation.

[0277] As mentioned above, ΔE ST (eV) was calculated. The results are shown in Table 3.

[0278] Example 14 (k RISC (Calculation of) >> Inverse interterm crossing velocity constant (k RISC The values ​​were calculated based on a previously published paper (Angewandte Chemie, 2022, 134, e202205684). Table 3 shows the relative values, with example compound 6 set as the baseline value of 1.0.

[0279]

[0280] Table 3 shows that the exemplary compounds 3, 6 and 12 to 21, which are organic compounds according to this embodiment, have a small ΔE. ST This was shown. Also, ΔE ST As the narrowing of the range increases, k becomes more important than compound A. RISC The size increased. Therefore, the organic light-emitting device using the organic compound according to this embodiment is expected to have excellent luminescence efficiency and device durability because the reverse intersystem crossing is fast and the retention time of excitons in the triplet excited state is short.

[0281] The 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, claims are attached to disclose the scope of the invention.

[0282] This application claims priority based on Japanese Patent Application No. 2024-164038 filed on September 20, 2024, Japanese Patent Application No. 2025-021010 filed on February 12, 2025, and Japanese Patent Application No. 2025-106348 filed on June 24, 2025, and all of the contents of those applications are incorporated herein by reference.

Claims

1. An organic compound characterized by being represented by the following general formula (1). In general formula (1), R 11 to R 16 and R 21 to R 26 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. R C is selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. Cy A ring and Cy B ring are each independently selected from the group consisting of an aryl ring having 6 to 13 carbon atoms and a heteroaryl ring having 3 to 12 carbon atoms. R A and R B each represent a group bonded to a carbon atom or a heteroatom constituting the Cy A ring and the Cy B ring, and are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, and a cyano group. Adjacent R A to each other, adjacent R B They may be bonded together to form a ring. n and m each represent an integer between 4 and 14. X1 and X2 are independently selected from the chalcogen atom group consisting of oxygen, sulfur, selenium, and tellurium atoms. Y1 and Y2 are independently selected from oxygen and sulfur atoms, respectively.

2. The organic compound according to claim 1, characterized by being represented by the following general formula (2) or (3). In general formula (3), Z1 and Z2 are each independently selected from the group consisting of O, S, Se, Te, CR'R'', NR', and SiR'R''. R' and R'' are each independently selected from the group consisting of substituted or unsubstituted alkyl groups and substituted or unsubstituted aryl groups.

3. The organic compound according to claim 1 or 2, characterized in that Y1 and Y2 are oxygen atoms.

4. The organic compound according to claim 1 or 2, characterized in that X1 and X2 are a sulfur atom, a selenium atom, or a tellurium atom.

5. The organic compound according to claim 4, characterized in that X1 and X2 are sulfur atoms or tellurium atoms.

6. In the general formula (2) above, R A , R B The organic compound according to any one of claims 2 to 5, characterized in that at least one of them is an alkyl group having 1 to 6 carbon atoms, or an aryl group having 5 to 7 carbon atoms.

7. In the above general formula (3), (R A ) 4, (R B R shown in )4 A , R B The organic compound according to any one of claims 2 to 5, characterized in that all of them are hydrogen atoms.

8. The aforementioned R C The organic compound according to any one of claims 1 to 7, characterized in that it is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 carbon atoms.

9. The aforementioned R C The organic compound according to claim 8, characterized in that it is a methyl group, an iso-propyl group, a tert-butyl group, a diarylamine group, a phenyl group, a phenyl group having an alkyl group as a substituent, or a biphenyl group.

10. Δ EST The organic compound according to any one of claims 1 to 7, characterized in that the calculated value is 0.40 eV or less.

11. An organic light-emitting element comprising a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, wherein at least one layer of the organic compound layer contains the organic compound described in any one of claims 1 to 10.

12. The organic light-emitting element according to claim 11, characterized in that the layer containing the organic compound is a light-emitting layer.

13. The organic light-emitting element according to claim 12, 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.

14. The organic light-emitting element according to claim 13, 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.

15. An ink composition characterized by containing the organic compound described in any one of claims 1 to 10.

16. 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 claim 11 and a transistor connected to the organic light-emitting element.

17. A photoelectric conversion device comprising an optical unit having a plurality of lenses, an image sensor that receives light that has passed through the optical unit, 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 11 to 14.

18. An image display device comprising a display unit having an organic light-emitting element as described in any one of claims 11 to 14, and a housing on which the display unit is provided.

19. An electronic device comprising: a display unit having an organic light-emitting element as described in any one of claims 11 to 14; a housing on which the display unit is provided; and a communication unit provided in the housing for communicating with the outside.

20. A wearable device comprising: a display unit having an organic light-emitting element as described in any one of claims 11 to 14; an optical system for focusing light from the display unit; and a control device for controlling the display of the display unit.

21. A lighting device comprising a light source having an organic light-emitting element as described in any one of claims 11 to 14, and a light-diffusing portion or optical film that transmits light emitted by the light source.

22. A mobile body characterized by comprising a lamp having an organic light-emitting element as described in any one of claims 11 to 14, and a body on which the lamp is provided.

23. An exposure light source for an electrophotographic image forming apparatus, characterized by having an organic light-emitting element according to any one of claims 11 to 14.

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