Organic Compound and Organic Light-Emitting Device

Abstract

To provide an organic compound with high emission efficiency.SOLUTION: An organic compound is represented by general formula [1]. In the formula [1], R1 to R8 are each independently selected from hydrogen, halogen, an alkyl group, and the like, and X1 is oxygen, sulfur, selenium, tellurium, or a CR9R10 group. R9 and R10 are each independently selected from hydrogen, halogen, an alkyl group, and the like, where at least one of R1 to R8 is a group represented by general formula [2]. R11 to R15 are each independently selected from hydrogen, halogen, an alkyl group, and the like, and *1 represents a binding position, where at least one of R11 to R15 is an amino group represented by general formula [3-1] or the like, and each X2 is independently selected from the group consisting of an alkyl group, a phenyl group, and the like. *2 represents a binding position.SELECTED DRAWING: None

Description

Technical Field

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

Background Art

[0002] An organic light-emitting device (hereinafter sometimes referred to as an "organic electroluminescence device" or an "organic EL device") is an electronic device having a pair of electrodes and an organic compound layer disposed between these electrodes. By injecting electrons and holes from these pair of electrodes, excitons of a light-emitting organic compound in the organic compound layer are generated, and when the excitons return to the ground state, the organic light-emitting device emits light. Recent progress in organic light-emitting devices is remarkable, including low driving voltage, various emission wavelengths, high-speed response, and the ability to make the light-emitting device thinner and lighter. Regarding the improvement of the efficiency of the light-emitting device, there are devices using high-efficiency materials such as phosphorescent materials and delayed fluorescence materials. Compound A-1 below is described in Patent Document 1, and compound A-2 below is described in Patent Document 2.

[0003]

Chemical Formula

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0005] However, when the compound A-1 described in Patent Document 1 and the compound A-2 described in Patent Document 2 are used in an organic light-emitting device, there are problems with luminous efficiency. The present invention has been made to solve the above problems, and an object thereof is to provide an organic compound having high luminous efficiency. Another object of the present invention is to provide an organic light-emitting device having excellent luminous efficiency and driving durability characteristics.

Means for Solving the Problems

[0006] The organic compound of the present invention is characterized by being represented by the following general formula [1].

[0007]

Chemical formula

[0008]

Chemical formula

[0009]

Chemical Formula

Advantages of the Invention

[0010] The organic compound according to the present invention has a structure excellent in light-emitting characteristics and film properties. Therefore, when used in an organic light-emitting device, an organic light-emitting device excellent in luminous efficiency and driving durability characteristics can be provided.

Brief Description of the Drawings

[0011] [Figure 1] It is a diagram showing the electron orbital distribution of HOMO and LUMO. [Figure 2] It is a diagram showing the aspect ratio of the molecule. [Figure 3] It is a schematic cross-sectional view of an example of a display device using the organic light-emitting device according to an embodiment of the present invention. [Figure 4] It is a schematic diagram showing an example of the display device according to an embodiment of the present invention. [Figure 5](a) A schematic diagram showing an example of an imaging device according to an embodiment of the present invention. (b) A schematic diagram showing an example of an electronic device according to an embodiment of the present invention. [Figure 6] (a) A schematic diagram showing an example of a display device according to an embodiment of the present invention. (b) A schematic diagram showing an example of a foldable display device. [Figure 7] (a) A schematic diagram showing an example of an illumination device according to an embodiment of the present invention. (b) A schematic diagram showing an example of an automobile having a vehicle lamp according to an embodiment of the present invention. [Figure 8] (a) A schematic diagram showing an example of a wearable device according to an embodiment of the present invention. (b) A schematic diagram showing another example of a wearable device according to an embodiment of the present invention. [Figure 9] (a) A schematic diagram showing an example of an image forming apparatus according to an embodiment of the present invention. (b)(c) A schematic diagram showing an example of an exposure light source of the image forming apparatus according to an embodiment of the present invention.

Embodiments for Carrying Out the Invention

[0012] ≪Organic Compound≫ First, the organic compound according to the present embodiment will be described. The organic compound according to the present embodiment is characterized by being represented by the following general formula [1].

[0013]

Chemical Formula

[0014] <R1 to R8> In general formula [1], R1 to R8 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a silyl group, and a cyano group.

[0015] Examples of the halogen atom include, but are not limited to, fluorine, chlorine, bromine, iodine, and the like.

[0016] Examples of the alkyl group include, but are not limited to, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, tertiary butyl group, secondary butyl group, octyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, and the like. The alkyl group is preferably an alkyl group having 1 to 10 carbon atoms.

[0017] Examples of the alkoxy group include, but are not limited to, methoxy group, ethoxy group, propoxy group, 2-ethyl-octyloxy group, benzyloxy group, and the like. The alkoxy group is preferably an alkoxy group having 1 to 10 carbon atoms.

[0018] Examples of the amino group 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-dibenzylamino 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-tertiary butylphenyl)amino group, N-phenyl-N-(4-trifluoromethylphenyl)amino group, N-piperidyl group, carbazolyl group, acridyl group, and the like.

[0019] Examples of the aromatic hydrocarbon group include, but are not limited to, a phenyl group, a naphthyl group, an indenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a phenanthryl group, a triphenylenyl group, a pyrenyl group, an anthranyl group, a perylenyl group, a chrysenyl group, a fluoranthenyl group, etc. The aromatic hydrocarbon group is preferably an aromatic hydrocarbon group having 6 to 60 carbon atoms.

[0020] Examples of the heterocyclic group include, but are not limited to, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a carbazolyl group, an acridinyl group, a phenanthrolyl group, etc. The heterocyclic group is preferably a heterocyclic group having 3 to 60 carbon atoms.

[0021] Examples of the aryloxy group include, but are not limited to, a phenoxy group, a naphthoxy group, etc.

[0022] Examples of the heteroaryloxy group include, but are not limited to, a furanyloxy group, a thienyloxy group, etc.

[0023] Examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triphenylsilyl group, etc.

[0024] Examples of the substituent that the above alkyl group, alkoxy group, amino group, aromatic hydrocarbon group, heterocyclic group, aryloxy group, or heteroaryloxy group may further have include, but are not limited to, an alkyl group such as methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, or tertiary butyl group; an aralkyl group such as benzyl group; an aromatic hydrocarbon group such as phenyl group, biphenyl group, or naphthyl group; a heterocyclic group such as pyridyl group, pyrrolyl group, pyrazyl group, or triazyl group; an amino group such as dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, or ditolylamino group; an alkoxy group such as methoxy group, ethoxy group, or propoxy group; an aryloxy group such as phenoxy group; a halogen atom such as fluorine, chlorine, bromine, or iodine; and a cyano group.

[0025] <x1> X1 represents any one of oxygen, sulfur, selenium, tellurium, CR9R 10 group. X1 is preferably oxygen or sulfur.

[0026] R9 and R 10 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a silyl group, and a cyano group.

[0027] R9 to R 10 Specific examples of the halogen atom, alkyl group, alkoxy group, amino group, aromatic hydrocarbon group, heterocyclic group, aryloxy group, heteroaryloxy group, and silyl group represented by are the same as those described for R1 to R8, but are not limited thereto. As the alkyl group, an alkyl group having 1 to 10 carbon atoms is preferable. As the alkoxy group, an alkoxy group having 1 to 10 carbon atoms is preferable. As the aromatic hydrocarbon group, an aromatic hydrocarbon group having 6 to 60 carbon atoms is preferable. As the heterocyclic group, a heterocyclic group having 3 to 60 carbon atoms is preferable. Specific examples of the substituents that the alkyl group, alkoxy group, amino group, aromatic hydrocarbon group, heterocyclic group, aryloxy group, and heteroaryloxy group may further have are the same as those described for R1 to R8, but are not limited thereto.

[0028] In the organic compound according to this embodiment, at least one of R1 to R8, preferably at least one of R1 to R4 and one of R5 to R8, is a group represented by the following general formula [2].

[0029]

Chemical formula

[0030] In general formula [2], R 11 up to R 15 is independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a silyl group, and a cyano group respectively. *1 represents the bonding position.

[0031] R 11 up to R 15 Specific examples of the halogen atom, alkyl group, alkoxy group, amino group, aromatic hydrocarbon group, heterocyclic group, aryloxy group, heteroaryloxy group, and silyl group represented by are the same as those described for R1 to R8, but are not limited thereto. As the alkyl group, an alkyl group having 1 to 10 carbon atoms is preferable. As the alkoxy group, an alkoxy group having 1 to 10 carbon atoms is preferable. As the aromatic hydrocarbon group, an aromatic hydrocarbon group having 6 to 60 carbon atoms is preferable. As the heterocyclic group, a heterocyclic group having 3 to 60 carbon atoms is preferable. Specific examples of the substituents that the alkyl group, alkoxy group, amino group, aromatic hydrocarbon group, heterocyclic group, aryloxy group, and heteroaryloxy group may further have are the same as those described for R1 to R8, but are not limited thereto.

[0032] The organic compound according to this embodiment has at least one of R 11 up to R 15 , preferably at least one of R 11 , R 12 , R 14 , R 15 is an amino group represented by the following general formulas [3-1] to [3-30].

[0033]

Chemical formula

[0034] In general formulas [3-1] to [3-30], X2 is independently selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, and a substituted or unsubstituted pyridyl group. X2s may be the same or different from each other. It is preferable that X2 is a substituted or unsubstituted alkyl group. *2 represents the bonding position.

[0035] Specific examples of the alkyl group represented by X2 include the same ones as those described for R1 to R8, but are not limited thereto. As the alkyl group, an alkyl group having 1 to 10 carbon atoms is preferable. Specific examples of the substituent that the alkyl group, phenyl group, naphthyl group, and pyridyl group may further have include the same ones as those described for R1 to R8, but are not limited thereto.

[0036] The amino group represented by general formulas [3-1] to [3-30] may further have a substituent. The substituent that the amino group represented by general formulas [3-1] to [3-30] may further have is not particularly limited, but is preferably selected from a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, a tertiary butyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a pyrazyl group, a triazyl group, a dimethylamino group, a diethylamino group, a dibenzylamino group, a diphenylamino group, a ditolylamino group, a methoxy group, an ethoxy group, a propoxy group, a phenoxy group, fluorine, chlorine, bromine, iodine, and a cyano group.

[0037] Next, a method for synthesizing the organic compound according to the present embodiment will be described. The organic compound according to the present embodiment is synthesized, for example, according to the reaction scheme shown below.

[0038]

Chemical formula

[0039] Here, by appropriately modifying the compounds shown in the above (a) to (c), the compound represented by the general formula [1] can be obtained. Note that the synthesis method is not limited to these.

[0040] Next, since the organic compound according to the present embodiment has the following characteristics, an organic light-emitting device having high-efficiency light emission and excellent driving durability characteristics can be provided by using it in an organic light-emitting device. The basic skeleton in the present embodiment is a skeleton in which all of R1 to R8 of the compound represented by the general formula [1] are hydrogen atoms. When X1 is a CR9R 10 group, it is further a skeleton in which all of R9 to R 10 are hydrogen atoms. (1) By having a ring structure containing a carbonyl group, which is an electron-withdrawing group, as a basic skeleton, and an amino group, which is an electron-donating group having a steric hindrance group X2, the energy gap between S1 and T1 is small. (2) By having an electron-donating amino group having at least a steric hindrance group X2 with respect to a highly planar basic skeleton, the aspect ratio of the molecule becomes large, and a compound having excellent film properties is obtained.

[0041] Hereinafter, the characteristics will be described. (1) By having a ring structure containing a carbonyl group, which is an electron-withdrawing group, as a basic skeleton, and an amino group, which is an electron-donating group having a steric hindrance group X2, the energy gap between S1 and T1 is small.

[0042] In creating the organic compound represented by the general formula [1], the present inventors focused on the electron distribution of the HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) of the compound.

[0043] As shown in Fig. 1, in exemplary compounds B-1 to B-2 and D-21 which are the compounds of this embodiment, the portion occupying the electron orbital distribution of HOMO and the portion occupying the electron orbital distribution of LUMO are separated. That is, it can be seen that the portion occupying both HOMO and LUMO is small. This leads to a small overlap integral and a small energy difference between the singlet excited state (S1) and the triplet excited state (T1). Specifically, the energy gaps between S1 and T1 of exemplary compounds B-1 to B-2 and D-21 are as small as 0.0004 eV, 0.0035 eV, and 0.0005 eV, respectively. On the other hand, the energy gaps between S1 and T1 of Comparative Compound 1 and Comparative Compound 2 are as large as 0.21 eV and 0.24 eV, respectively. Note that Comparative Compound 1 is Compound A-1 described in Patent Document 1, and Comparative Compound 2 is Compound A-2 described in Patent Document 2.

[0044] This feature is the effect of having a condensed ring structure in which a carbonyl group, which is an electron-withdrawing group, forms a ring structure while bonding as a basic skeleton, and further having an electron-donating amino group having a steric hindrance group X2. Note that the steric hindrance group in the present invention is X2 of the amino group represented by General Formulas [3-1] to [3-30]. This steric hindrance group has the effect of causing the amino group represented by General Formulas [3-1] to [3-30], which binds to the group represented by General Formula [2], to have a twisted structure.

[0045] On the other hand, when having an amino group without a steric hindrance group like Comparative Compound 1 and Comparative Compound 2, the overlap between the portion occupying the electron orbital distribution of HOMO and the portion occupying the electron orbital distribution of LUMO is large. For this reason, the energy gap between S1 and T1 becomes large.

[0046] Note that the above calculation results were visualized using molecular orbital calculations. The calculation method of the molecular orbital calculation method used the currently widely used density functional theory (DFT). The functional was B3LYP, and the basis function was 6-31G * It was used. The molecular orbital calculation method was carried out using Gaussian09 (Gaussian09, Revision C.01, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, 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.), which is widely used currently.

[0047] Thus, the compound of this embodiment is characterized by a small energy difference between S1 and T1. By using the compound of this embodiment in the light-emitting layer of an organic light-emitting device, a device with high-efficiency light emission can be provided. The reason is that for excitons generated with a singlet exciton to triplet exciton ratio of 1:3 due to the small S1 and T1, the triplet excitons that were usually thermally deactivated can be used for delayed fluorescence-type light emission from the singlet excited state. To convert triplet excitons to the singlet excited state, it is advantageous that the difference between S1 and T1 is small because the energy barrier becomes smaller. Therefore, the compound of this embodiment with a small energy difference between S1 and T1 can easily convert triplet excitons to the singlet excited state, and thus can provide a device with high-efficiency light emission.

[0048] (2) By having an electron-donating amino group having at least a steric hindrance group X2 with respect to a highly planar basic skeleton, the aspect ratio of the molecule becomes large, resulting in a compound with excellent film properties.

[0049] In creating the organic compound represented by the general formula [1], the present inventors focused on the planarity of the compound. The basic skeleton of the compound of this embodiment has a structure in which an electron-withdrawing carbonyl group condenses while forming a six-membered ring, so it has a highly planar structure. High planarity makes it easy for molecules to stack. In other words, it is not preferable because molecular aggregation is likely to occur. This is because in an organic light-emitting device, molecular aggregation causes a decrease in efficiency due to concentration quenching. Also, molecular aggregation is disadvantageous for reverse intersystem crossing. This is because exciton annihilation (TTA) due to energy transfer of triplet excitons occurring between molecules is likely to occur, and reverse intersystem crossing to singlet excitons is less likely to occur.

[0050] Therefore, the present inventors found that an amino group represented by the general formulas [3-1] to [3-30] should be introduced as a group having a steric hindrance group. By introducing an amino group having a steric hindrance group, the molecular aspect ratio can be decreased and molecular aggregation can be reduced.

[0051] Here, the molecular aspect ratio in the present invention is the ratio of the maximum molecular length (molecular diameter) in the xy plane including the basic skeleton to the molecular length (molecular thickness) in the z-axis direction orthogonal to the xy plane including the basic skeleton, and is defined as molecular aspect ratio = (molecular diameter) / (molecular thickness). That is, the larger the molecular aspect ratio, the higher the planarity, which is not preferable. On the other hand, the smaller the molecular aspect ratio, the lower the planarity, and since molecular aggregation can be reduced, it is preferable. Specifically, the molecular aspect ratio is preferably 5.0 or less. More preferably, it is preferably 3.0 or less. Note that the molecular lengths of the molecular diameter and the molecular thickness are calculated from the molecular lengths in the ball-and-bond type display using the molecular structure obtained by the optimization structure calculation.

[0052] Here, the results of comparing the molecular aspect ratios are shown in FIG. 2. From FIG. 2, the molecular aspect ratios of the exemplary compounds B-1, B-2, and B-15 are 2.7, 1.8, and 3.3, respectively, while the comparative compound 1 is as large as 7.5. This is because the compounds of the present embodiment have an amino group having a steric hindrance group.

[0053] From the above, the compounds according to the present embodiment have a low molecular aspect ratio and are less likely to cause stacking between molecules, so molecular aggregation is less likely to occur.

[0054] In addition, this feature is also effective in improving the amorphous property of organic compounds. When the compound of the present embodiment is used in the organic layer of an organic light-emitting device, it is difficult to crystallize, forms a stable amorphous film, and an organic light-emitting device excellent in high durability can be obtained without crystallization even after long-term driving.

[0055] Furthermore, this feature also has the effect of improving sublimability. The improvement of sublimability enables high purification of materials by sublimation purification and the production of organic light-emitting devices by vapor deposition. Thereby, impurities contained in the organic light-emitting device can be reduced, and it is possible to prevent a decrease in light emission efficiency and a decrease in driving durability due to impurities.

[0056] Furthermore, it is preferable that the organic compound satisfies the following conditions (3) to (6).

[0057] (3)At least one of R1 to R4 and at least one of R5 to R8 is a group represented by the general formula [2]. This is because when this condition is satisfied, the molecular aspect ratio decreases. Specifically, in FIG. 2, it can be seen that the exemplified compounds B-1 and B-2 in which any one of R1 to R4 is a group represented by the general formula [2] have a smaller molecular aspect ratio than the exemplified compound B-15 having a group represented by the general formula [2] in R1 to R4 and R5 to R8. Thus, as described in the above feature (2), it is preferable because molecular aggregation is further reduced. When this condition is satisfied, the other of R1 to R4 and R5 to R8 is preferably selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, and a cyano group.

[0058] (4)X1 is oxygen or sulfur. This is because when this condition is satisfied, oxygen atoms and sulfur atoms have many lone pairs and become more stable compounds against the redox reactions repeated in the organic light-emitting element.

[0059] (5)R 11 、R 12 、R 14 、R 15 At least one of them is an amino group represented by the general formulas [3-1] to [3-30]. This is because when this condition is satisfied, the molecular aspect ratio decreases. Specifically, in FIG. 2, it can be seen that the exemplified compound B-2 having an amino group in R 12 of the group represented by the general formula [2] has a smaller molecular aspect ratio than the exemplified compound B-1 having an amino group in R 13 Thus, as described in the above feature (2), it is preferable because molecular aggregation is further reduced. When this condition is satisfied, R 13 is preferably a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted phenyl group, rather than an amino group represented by General Formulas [3-1] to [3-30].

[0060] (6) X2 is a substituted or unsubstituted alkyl group. This is because the amino group represented by General Formulas [3-1] to [3-30] is the part responsible for the HOMO of the compound, and introducing an alkyl group that is electron-donating to this amino group has the effect of enhancing the electron-donating property of the HOMO. Therefore, the charge separation between the HOMO and LUMO of the compound is promoted, and the energy difference between S1 and T1 becomes smaller. That is, as described in the above characteristic (1), it is preferable from the viewpoint of improving the light emission efficiency.

[0061] Furthermore, it is particularly preferable that X2 is a methyl group. This is because the energy gap between S1 and T1 can be reduced with a group having a lower molecular weight. A lower molecular weight is preferable from the viewpoint of sublimability, and an improvement in purity by sublimation purification can be expected. Good sublimability and ease of high-purification mean that impurities contained in the device can be reduced when manufacturing an organic light-emitting device, and an improvement in device characteristics can be expected.

[0062] Furthermore, the compound of the present embodiment is preferably used in the light-emitting layer in an organic light-emitting device, and in that case, it has the following characteristics. (7) By mixing the compound of the present embodiment with a host material in the light-emitting layer, the compound of the present embodiment is more likely to cause exciton recombination, providing a highly efficient light-emitting device. (8) By mixing the compound of the present embodiment with a host material in the light-emitting layer and further having a light-emitting material, a highly efficient and high-color-purity light-emitting device is provided. (9) When the light-emitting material is a hydrocarbon compound, a highly efficient and long-lasting light-emitting device is provided.

[0063] Hereinafter, the characteristics will be described. (7) By mixing the compound of this embodiment with a host material in the light-emitting layer, the compound of this embodiment is more likely to cause exciton recombination, providing a highly efficient light-emitting device.

[0064] The compound of this embodiment has a carbonyl group which is electron-withdrawing, and by substituting an amino group which is electron-donating and mixing it with a host material in the light-emitting layer of an organic light-emitting device, the LUMO of the compound of this embodiment is at a lower level (farther from the vacuum level) than that of the host material, and the HOMO of the compound of this embodiment becomes at a higher level (closer to the vacuum level) than that of the host material.

[0065] Therefore, electrons and holes supplied from the transport layer in the light-emitting layer are trapped by the compound of this embodiment, and exciton recombination occurs. As described in the above feature (1), since the energy difference between S1 and T1 of the compound of this embodiment is small, it efficiently generates delayed fluorescence-type emission in the light-emitting layer, and more triplet excitons can be utilized for emission. In particular, this effect is significant when the host material is a hydrocarbon compound because the energy difference between the HOMO and LUMO of the host and the compound of this embodiment becomes larger, making it easier to trap electrons and holes. A hydrocarbon compound is a compound composed only of carbon and hydrogen.

[0066] (8) By mixing the compound of this embodiment with a host material in the light-emitting layer and further having a light-emitting material, a highly efficient and high-color-purity light-emitting device is provided.

[0067] The compound of this embodiment is used in the light-emitting layer, and further doped with a light-emitting material having a high photoluminescence quantum yield used as a light-emitting material and a light-emitting material having a spectrum suitable for showing high color purity in the emission spectrum, thereby providing a light-emitting device with higher efficiency and higher color purity. In this case, the compound of this embodiment functions as an assist material and needs to be configured at a concentration such that it can preferentially trap electrons and holes in the light-emitting layer in order to facilitate exciton recombination. The compound of this embodiment is preferably 0.1% by mass or more and 45% by mass or less, more preferably 1% by mass or more and 30% by mass or less, based on the entire light-emitting layer. On the other hand, since the doping concentration as a light-emitting material is less affected by concentration quenching due to intermolecular interaction and changes in the emission spectrum, it is preferable to dope a light-emitting material other than the compound of this embodiment in the light-emitting layer. Preferably, the doping concentration of the light-emitting material is 10% by mass or less, more preferably 5% by mass or less. As described above, a light-emitting device with high efficiency and high color purity can be provided.

[0068] (9) When the light-emitting material is a hydrocarbon compound, a light-emitting device with high efficiency and good durability characteristics is provided.

[0069] Since the compound of this embodiment has a strongly electron-withdrawing carbonyl group, the light-emitting material doped in feature (8) is preferably a light-emitting material having no amino group which is an electron-donating group, and a hydrocarbon compound is preferable. The reason is that in the case of a light-emitting material having an amino group, the carbonyl group of the compound of this embodiment interacts in the light-emitting layer, resulting in a decrease in emission efficiency due to exciplex formation and a change in the emission spectrum of the light-emitting material, thereby deteriorating the color purity of the light-emitting device.

[0070] Furthermore, since a light-emitting material having an amino group has a low ionization potential, it is easily oxidized and the device durability is poor. Therefore, the light-emitting material is preferably a compound composed of hydrocarbons, more preferably a condensed polycyclic compound having a 5-membered ring. This is because it has a structure with a higher ionization potential and is less likely to be oxidized. A hydrocarbon compound is a compound composed only of carbon and hydrogen in the molecule.

[0071] As described above, by mixing the compound of the present embodiment with a host material in a light-emitting layer, an organic light-emitting device with high-efficiency light emission can be obtained. At this time, the light-emitting material may be the compound of the present embodiment, or a light-emitting material may be further mixed and the compound of the present embodiment may function as an assist material. By using a light-emitting material with good color purity, an organic light-emitting device with high efficiency and high color purity can be obtained. Furthermore, when the host material is a hydrocarbon compound, the compound of the present embodiment is likely to trap electrons and holes, so the effect of improving efficiency is greatly preferable.

[0072] Specific examples of the organic compound according to the present invention are shown below (B-35, 36, C-3, 8, 10, 13, 15, D-7, 8 are reference examples) . However, the present invention is not limited to these.

[0073]

Chemical formula

[0074]

Chemical formula

[0075]

Chemical formula

[0076]

Chemical formula

[0077]

Chemical formula

[0078] Those belonging to Group B are compounds in which X1 is oxygen in the compound represented by the general formula [1]. Since X1 is oxygen, a condensed polycyclic structure having an electron-withdrawing carbonyl group is less likely to undergo chemical reactions such as oxidation, providing a chemically stable compound.

[0079] Those belonging to Group C are compounds in which X1 is sulfur in the compound represented by the general formula [1]. Since X1 is sulfur, the condensed polycyclic structure having an electron-withdrawing carbonyl group becomes a structure rich in lone pairs, resulting in a compound with more excellent carrier transport ability.

[0080] Those belonging to Group D are compounds in which X1 is CR9R in the compound represented by the general formula [1]. 10 Since X1 is CR9R 10 it is excellent in reducing molecular aggregation. Therefore, it becomes a compound that is less likely to undergo concentration quenching.

[0081] Those belonging to Group E are compounds in which X1 is selenium or tellurium in the compound represented by the general formula [1]. Since selenium and tellurium have d orbitals and are metallic elements, the compounds belonging to Group E have high carrier mobility.

[0082] The organic compound according to this embodiment is a compound with high luminous efficiency and excellent film properties. Therefore, by using the organic compound according to this embodiment as a constituent material of an organic light-emitting device, an organic light-emitting device having good light-emitting characteristics and excellent durability characteristics can be obtained.

[0083] ≪Organic Light-Emitting Device≫ Next, the organic light-emitting device of this embodiment will be described.

[0084] The organic light-emitting device of this embodiment has at least an anode and a cathode which are a pair of electrodes, and an organic compound layer disposed between these electrodes. In the organic light-emitting device of this 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. 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. Also, the light-emitting layer may be a single layer or a laminate composed of a plurality of layers.

[0085] In the organic light-emitting device of the present embodiment, at least one layer of the organic compound layer contains the organic compound according to the present embodiment. Specifically, the organic compound according to the present embodiment is included in any one of the above-described light-emitting layer, hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole-exciton blocking layer, electron transport layer, electron injection layer, and the like. The organic compound according to the present embodiment is preferably included in the light-emitting layer. The light-emitting layer can emit green light or red light, but the emission color is not limited thereto. The light-emitting layer can emit green light or red light, but the emission color is not limited thereto.

[0086] In the organic light-emitting device of the present embodiment, when the organic compound according to the present embodiment is included in the light-emitting layer, the light-emitting layer may be a layer composed only of the organic compound according to the present embodiment, or a layer composed of the organic compound according to the present embodiment and other compounds. Here, when the light-emitting layer is a layer composed of the organic compound according to the present embodiment and other compounds, the organic compound according to the present embodiment may be used as a host of the light-emitting layer, or may be used as a guest. It may also be used as an assist material that can be included in the light-emitting layer. Here, the host is the compound having the largest mass ratio among the compounds constituting the light-emitting layer. The guest is a compound having a mass ratio smaller than that of the host among the compounds constituting the light-emitting layer and is a compound responsible for main emission. The assist material is a compound having a mass ratio smaller than that of the host among the compounds constituting the light-emitting layer and assisting the emission of the guest.

[0087] Here, when the organic compound according to the present embodiment is used as a guest of the light-emitting layer, the concentration of the guest is preferably 0.01% by mass or more and 20% by mass or less, more preferably 1% by mass or more and 15% by mass or less, based on the entire light-emitting layer. When the organic compound according to the present embodiment is used as an assist material of the light-emitting layer, the concentration of the assist material is preferably 0.1% by mass or more and 45% by mass or less, more preferably 1% by mass or more and 30% by mass or less, based on the entire light-emitting layer.

[0088] When using the organic compound according to this embodiment as a guest in the light-emitting layer, it is preferable to use a material having a higher LUMO than the organic compound according to this embodiment (a material having a LUMO closer to the vacuum level) as a host. Since the organic compound of this embodiment has a carbonyl group, its LUMO is low (far from the vacuum level). Therefore, when the organic compound of this embodiment is used in the light-emitting layer, it is easy to form the above-described LUMO relationship. This is because by using a material having a higher LUMO than the organic compound according to this embodiment as a host, the organic compound according to this embodiment can receive more electrons supplied to the host of the light-emitting layer.

[0089] When using the organic compound according to this embodiment as an assist material in the light-emitting layer, it is preferable to use a material having a higher LUMO than the organic compound according to this embodiment (a material having a LUMO closer to the vacuum level) as a guest. Since the organic compound of this embodiment has a carbonyl group, its LUMO is low (far from the vacuum level). Therefore, when the organic compound of this embodiment is used in the light-emitting layer, it is easy to form the above-described LUMO relationship. By using a material having a higher LUMO than the organic compound of this embodiment as a guest which is a light-emitting material, the organic compound of this embodiment can receive more electrons supplied to the host of the light-emitting layer, and the assist material is responsible for exciton recombination. As a result, it becomes possible to efficiently cause energy transfer to the guest which is a light-emitting material.

[0090] The inventors have conducted various studies and found that when the organic compound according to this embodiment is used as a host, guest, or assist material in the light-emitting layer, particularly as a guest in the light-emitting layer, an element with high-efficiency and high-brightness light output and extremely high durability can be obtained. Furthermore, when used as an assist material in the light-emitting layer, it has been found that an element with high-efficiency and high-brightness light output and extremely high durability can be obtained. This light-emitting layer may be a single layer or a multilayer, and may also contain a plurality of light-emitting materials. The multilayer may be a state where another light-emitting layer is laminated on the light-emitting layer, or an intermediate layer may be laminated between a plurality of light-emitting layers. Also, tandem elements or stack elements may be used. In these cases, the emission color of the organic light-emitting element is not limited to a single color. More specifically, it may be white or an intermediate color. Also, the film formation method is film formation by evaporation or coating film formation. Details of this will be described in detail in the examples described later.

[0091] The organic compound according to this embodiment can be used as a constituent material of an organic compound layer other than the light-emitting layer constituting the organic light-emitting element of this embodiment. Specifically, it may be used as a constituent material of an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, a hole blocking layer, etc.

[0092] Here, in addition to the organic compound according to this embodiment, conventionally known low-molecular and high-molecular hole injection compounds or hole transport compounds, host compounds, light-emitting compounds, electron injection compounds, or electron transport compounds, etc. can be used together as necessary. Examples of these compounds are given below.

[0093] As a hole injection and transport material, a material with a high hole mobility is preferred, which facilitates the injection of holes from the anode and transports the injected holes to the light-emitting layer. Also, in order to reduce the deterioration of the film quality such as crystallization in the organic light-emitting device, a material with a high glass transition temperature is preferred. Examples of low molecular weight and high molecular weight materials having hole injection and transport performance include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. Furthermore, the above hole injection and transport materials are also preferably used for the electron blocking layer. Specific examples of the compounds used as the hole injection and transport materials are shown below, but of course, they are not limited thereto.

[0094] [Chemical formula]

[0095] Among those listed as hole transport materials, 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, HT3, HT4, HT5, HT6, HT10, and HT12 may be used in the organic compound layer adjacent to HT16. Also, multiple materials may be used in one organic compound layer.

[0096] As the light-emitting materials mainly related to the light-emitting function, in addition to the organic compounds of this embodiment, condensed ring compounds (such as fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, organoaluminum complexes such as tris(8-quinolinolato)aluminum, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, and polymer derivatives such as poly(phenylene vinylene) derivatives, poly(fluorene) derivatives, and poly(phenylene) derivatives can be mentioned. Specific examples of the compounds used as the light-emitting materials are shown below, but of course, they are not limited thereto.

[0097]

Chem.

[0098]

Chem.

[0099] When the light-emitting material is a hydrocarbon compound, it is preferable to prevent a decrease in the light-emitting efficiency due to exciplex formation and a deterioration in color purity due to a change in the emission spectrum of the light-emitting material. A hydrocarbon compound is a compound composed only of carbon and hydrogen, and BD7, BD8, GD5 to GD9, and RD1 correspond thereto. When the light-emitting material is a condensed polycycle containing a five-membered ring, it is more preferable because it has a high ionization potential, is difficult to oxidize, and provides an element with a long and durable life. BD7, BD8, GD5 to GD9, and RD1 correspond thereto.

[0100] Examples of the light-emitting layer host or light-emitting assist material contained in the light-emitting layer include aromatic hydrocarbon compounds or their derivatives, carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organoaluminum complexes such as tris(8-quinolinolato)aluminum, and organoberyllium complexes. Specific examples of the compounds used as the light-emitting layer host or light-emitting assist material contained in the light-emitting layer are shown below, but of course, they are not limited thereto.

[0101]

Chem.

[0102] When the host material is a hydrocarbon compound, the compound of the present embodiment easily traps electrons and holes, so the effect of improving the efficiency is greatly preferable. A hydrocarbon compound is a compound composed only of carbon and hydrogen, and EM1 to EM12 and EM16 to EM27 correspond thereto.

[0103] As the electron transporting material, it can be arbitrarily selected from those capable of transporting electrons injected from the cathode to the light emitting layer, and is selected in consideration of the balance with the hole mobility of the hole transporting material and the like. Examples of materials having electron transporting performance include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organic aluminum complexes, and condensed ring compounds (for example, fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the above electron transporting materials are also preferably used for the hole blocking layer. Specific examples of the compounds used as the electron transporting material are shown below, but of course, they are not limited thereto.

[0104] [Chemical formula]

[0105] As the electron injecting material, it can be arbitrarily selected from those that can easily inject electrons from the cathode, and is selected in consideration of the balance with the hole injecting property and the like. Organic compounds also include n-type dopants and reducing dopants. For example, compounds containing alkali metals such as lithium fluoride, lithium complexes such as lithium quinolinol, benzimidazolidene derivatives, imidazolidene derivatives, fulvalene derivatives, and acridine derivatives can be mentioned.

[0106] [Structure of organic light emitting device] The organic light emitting device is provided by forming an anode, an organic compound layer, and a cathode on a substrate. A protective layer, a color filter, etc. may be provided on the cathode. When providing a color filter, a planarization layer may be provided between the protective layer. The planarization layer can be composed of an acrylic resin or the like.

[0107] [Substrate] Examples of the substrate include quartz, glass, silicon wafers, resins, metals, etc. The substrate may be provided with switching elements such as transistors and wirings thereon, and an insulating layer may be provided thereon. As the insulating layer, any material may be used as long as it can form contact holes to ensure electrical connection between the anode and the wiring and can ensure insulation from non-connected wirings. For example, resins such as polyimide, silicon oxide, silicon nitride, etc. can be used.

[0108] [Electrode] A pair of electrodes can be used as the electrodes. The pair of electrodes may be an anode and a cathode. When an electric field is applied in the direction in which the organic light-emitting element emits light, the electrode with a higher potential is the anode and the other is the cathode. Also, it can be said that the electrode that supplies holes to the light-emitting layer is the anode and the electrode that supplies electrons is the cathode.

[0109] As the constituent material of the anode, those with as large a work function as possible are preferable. For example, simple metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, tungsten, etc., mixtures containing these, alloys combining these, metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide, etc. can be used. Also, conductive polymers such as polyaniline, polypyrrole, polythiophene, etc. can be used.

[0110] These electrode materials may be used alone or in combination of two or more. Also, the anode may be composed of a single layer or multiple layers.

[0111] When used as a reflective electrode, for example, chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys thereof, laminated materials, etc. can be used. Also, when used as a transparent electrode, oxide transparent conductive layers such as indium tin oxide (ITO), indium zinc oxide, etc. can be used, but are not limited thereto. Photolithography technology can be used for forming the electrodes.

[0112] On the one hand, as the constituent material of the cathode, those with a small work function are preferable. For example, alkali metals such as lithium, alkaline earth metals such as calcium, simple metals such as aluminum, titanium, manganese, silver, lead, chromium, or mixtures containing these can be mentioned. Alternatively, alloys combining these simple metals can also be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper, zinc-silver, etc. can be used. The use of metal oxides such as indium tin oxide (ITO) is also possible. These electrode materials may be used alone or in combination of two or more. Also, the cathode may have a single-layer structure or a multi-layer structure. Among them, it is preferable to use silver, and in order to reduce the aggregation of silver, it is more preferable to use a silver alloy. As long as the aggregation of silver can be reduced, the ratio of the alloy does not matter. For example, it may be 1:1.

[0113] The cathode may be a top emission element using an oxide conductive layer such as ITO, or a bottom emission element using a reflective electrode such as aluminum (Al), and is not particularly limited. As the method for forming the cathode, although not particularly limited, it is more preferable to use direct current and alternating current sputtering methods, etc., because the film coverage is good and the resistance is easily reduced.

[0114] [Protective layer] A protective layer may be provided on the cathode. For example, by adhering glass provided with a moisture absorbent on the cathode, the intrusion of water, etc. into the organic compound layer can be suppressed, and the occurrence of display defects can be suppressed. Also, as another embodiment, a passivation film such as silicon nitride may be provided on the cathode to suppress the intrusion of water, etc. into the organic compound layer. For example, after forming the cathode, it can be transported to another chamber without breaking the vacuum, and a silicon nitride film with a thickness of 2 μm can be formed by CVD method to be used as a protective layer. A protective layer using atomic layer deposition method (ALD method) may be provided after the film formation by CVD method.

[0115] [Color filter] A color filter may be provided on the protective layer. For example, a color filter considering the size of the organic light-emitting element may be provided on another substrate and bonded to the substrate provided with the organic light-emitting element, or a color filter may be patterned on the protective layer shown above using photolithography technology. The color filter may be composed of a polymer.

[0116] [Flattening layer] A flattening layer may be provided between the color filter and the protective layer. The flattening layer may be composed of an organic compound, and may be a low molecule or a polymer, but a polymer is preferable.

[0117] The flattening layer may be provided above and below the color filter, and the constituent materials thereof may be the same or different. Specifically, examples include polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicon resin, urea resin, etc.

[0118] [Counter substrate] A counter substrate may be provided on the flattening layer. Since the counter substrate is provided at a position corresponding to the aforementioned substrate, it is called a counter substrate. The constituent material of the counter substrate may be the same as that of the aforementioned substrate.

[0119] [Organic layer] The organic compound layers (hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, electron injection layer, etc.) constituting the organic light-emitting element according to an embodiment of the present invention are formed by the following method.

[0120] For the organic compound layers constituting the organic light-emitting element according to an embodiment of the present invention, dry processes such as vacuum evaporation, ionization evaporation, sputtering, and plasma can be used. Also, instead of the dry process, a wet process of dissolving in an appropriate solvent and forming a layer by a known coating method (for example, spin coating, dipping, casting method, LB method, inkjet method, etc.) can be used.

[0121] When a layer is formed by a vacuum evaporation method, a solution coating method, or the like, crystallization and the like hardly occur, and the layer has excellent stability over time. Further, when forming a film by a coating method, a film can also be formed in combination with an appropriate binder resin.

[0122] Examples of the binder resin include, but are not limited to, polyvinyl carbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, urea resin, and the like.

[0123] In addition, these binder resins may be used alone as a homopolymer or copolymer, or two or more of them may be mixed and used. Furthermore, additives such as known plasticizers, antioxidants, and ultraviolet absorbers may be used in combination as necessary.

[0124] <Use of the organic light-emitting element according to the present embodiment> The organic light-emitting element according to the present embodiment can be used as a component of a display device or a lighting device. In addition, there are applications such as an exposure light source of an electrophotographic image forming device, a backlight of a liquid crystal display device, and a light-emitting device having a color filter for a white light source.

[0125] The display device may be an image information processing device that has an image input unit for inputting image information from an area CCD, a linear CCD, a memory card, etc., has an information processing unit for processing the input information, and displays 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 according to the present embodiment and a transistor connected to the organic light-emitting element.

[0126] In addition, the display unit included in an imaging device or an inkjet printer may have a touch panel function. The driving method of this touch panel function may be an infrared method, a capacitance method, a resistive film method, or an electromagnetic induction method, and is not particularly limited. The display device may also be used for the display unit of a multifunction printer.

[0127] Next, the display device according to this embodiment will be described with reference to the drawings. FIG. 3 is a schematic cross-sectional view showing an example of a display device having an organic light-emitting element and a TFT element connected to the organic light-emitting element. The TFT element is an example of an active element.

[0128] In the display device 10 of FIG. 3, a substrate 11 such as glass is provided with a moisture-proof film 12 for protecting the TFT element or the organic compound layer on the upper part thereof. Reference numeral 13 denotes a metal gate electrode. Reference numeral 14 denotes a gate insulating film, and 15 denotes a semiconductor layer.

[0129] The TFT element 18 has a semiconductor layer 15, a drain electrode 16, and a source electrode 17. An insulating film 19 is provided on the upper part of the TFT element 18. The anode 21 constituting the organic light-emitting element 26 and the source electrode 17 are connected via a contact hole 20.

[0130] 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 element 18 is not limited to the mode shown in FIG. 3. That is, either one of the anode 21 or the cathode 23 and either one of the source electrode 17 or the drain electrode 16 of the TFT element 18 may be electrically connected.

[0131] In the display device 10 of FIG. 3, the organic compound layer 22 is illustrated as a single layer, but the organic compound layer 22 may be a plurality of layers. A first protective layer 24 and a second protective layer 25 for reducing the deterioration of the organic light-emitting element 26 are provided on the cathode 23.

[0132] In the display device 10 of FIG. 3, a transistor is used as a switching element, but an MIM element may be used as a switching element instead.

[0133] In addition, the transistor used in the display device 10 of FIG. 3 is not limited to a transistor using a single-crystalline silicon wafer, and may be a thin-film transistor having an active layer on an insulating surface of a substrate. Examples of the active layer include non-single-crystalline silicon such as single-crystalline silicon, amorphous silicon, and microcrystalline silicon, and non-single-crystalline oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Note that a thin-film transistor is also called a TFT element.

[0134] The transistor included in the display device 10 of FIG. 3 may be formed in a substrate such as an Si substrate. Here, forming in the substrate means manufacturing a transistor by processing the substrate itself such as an Si substrate. That is, having a transistor in the substrate can also be regarded as the substrate and the transistor being integrally formed.

[0135] The organic light-emitting element according to this embodiment has its emission luminance controlled by a TFT which is an example of a switching element, and an image can be displayed by the respective emission luminances by providing the organic light-emitting elements in a plurality of planes. Note that the switching element according to this embodiment is not limited to a TFT, and may be a transistor formed of low-temperature polysilicon or an active matrix driver formed on a substrate such as an Si substrate. Forming on the substrate can also mean forming in the substrate. Whether to provide a transistor in the substrate or use a TFT is selected according to the size of the display portion. For example, if the size is about 0.5 inches, it is preferable to provide the organic light-emitting element on the Si substrate.

[0136] FIG. 4 is a schematic diagram showing an example of the display device according to the present embodiment. The display device 1000 may include a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008 between an upper cover 1001 and a lower cover 1009. The touch panel 1003 and the display panel 1005 are connected to flexible printed circuits FPC 1002 and 1004. Transistors are printed on the circuit board 1007. The battery 1008 may not be provided if the display device is not a portable device, or may be provided at another position even if the display device is a portable device.

[0137] The display device according to the present embodiment may be used for a display unit of a photoelectric conversion device such as an imaging device having an optical unit having a plurality of lenses and an imaging element that receives light that has passed through the optical unit. The imaging device may have a display unit that displays information acquired by the imaging element. Further, the display unit may be a display unit exposed to the outside of the imaging device or a display unit disposed in the viewfinder. The imaging device may be a digital camera or a digital video camera. The imaging device may be referred to as a photoelectric conversion device.

[0138] FIG. 5(a) is a schematic diagram showing an example of the imaging device according to the present 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 may include the display device according to the present embodiment. In that case, the display device may display not only the image to be captured but also environmental information, imaging instructions, and the like. The environmental information may include the intensity of external light, the direction of external light, the speed at which the subject moves, the possibility that the subject is shielded by an obstacle, and the like.

[0139] Since the timing suitable for imaging is a very short time, it is better to display information as soon as possible. Therefore, it is preferable to use the display device using the organic light emitting element of the present embodiment. This is because the organic light emitting element has a high response speed. The display device using the organic light emitting element can be more preferably used than these devices, such as a liquid crystal display device, for which a display speed is required.

[0140] The imaging device 1100 has an optical unit (not shown). The optical unit has a plurality of lenses and forms an image on an image sensor housed in the housing 1104. The plurality of lenses can adjust the focus by adjusting their relative positions. This operation can also be performed automatically.

[0141] The display device according to the present embodiment may have a color filter having red, green, and blue. The red, green, and blue colors of the color filter may be arranged in a delta array.

[0142] The display device according to the present embodiment may be used for a display unit of an electronic device such as a mobile terminal. In that case, it may have both a display function and an operation function. Examples of the mobile terminal include mobile phones such as smartphones, tablets, and head-mounted displays.

[0143] FIG. 5(b) is a schematic diagram showing an example of an electronic device according to the present 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 reaction unit of a touch panel method. The operation unit may be a biometric recognition unit that recognizes a fingerprint and performs operations such as unlocking. An electronic device having a communication unit can also be called a communication device.

[0144] FIG. 6 is a schematic diagram showing an example of a display device according to the present embodiment. FIG. 6(a) shows a display device such as a TV monitor or a PC monitor. The display device 1300 has a frame 1301 and a display unit 1302. The light-emitting device according to the present embodiment may be used for the display unit 1302. The frame 1301 and a base 1303 that supports the display unit 1302 are provided. The base 1303 is not limited to the form shown in FIG. 6(a). The lower side of the frame 1301 may also serve as the base. Further, the frame 1301 and the display unit 1302 may be curved. The radius of curvature may be 5000 mm or more and 6000 mm or less.

[0145] FIG. 6(b) is a schematic diagram showing another example of the display device according to the present embodiment. The display device 1310 in FIG. 6(b) is configured to be foldable, and is a so-called foldable display device. The display device 1310 includes a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may include the light-emitting device according to the present embodiment. The first display unit 1311 and the second display unit 1312 may be a single seamless display device. The first display unit 1311 and the second display unit 1312 can be separated at the bending point. The first display unit 1311 and the second display unit 1312 may display different images, or may display one image together with the first and second display units.

[0146] FIG. 7(a) is a schematic diagram showing an example of the lighting device according to the present embodiment. The lighting device 1400 may include a housing 1401, a light source 1402, a circuit board 1403, an optical filter 1404 that transmits light emitted by the light source 1402, and a light diffusing unit 1405. The light source 1402 may include the organic light-emitting element according to the present embodiment. The optical filter 1404 may be a filter that improves the color rendering property of the light source. The light diffusing unit 1405 can effectively diffuse the light of the light source, such as lighting up, and deliver the light to a wide range. The optical filter 1404 and the light diffusing unit 1405 may be provided on the light-emitting side of the lighting. If necessary, a cover may be provided on the outermost side.

[0147] The lighting device is, for example, a device that illuminates an interior. The lighting device may emit any color from white, day white, or other colors from blue to red. It may have a dimming circuit for dimming them. The lighting device may include the organic light-emitting element of the present embodiment and a power supply circuit connected thereto. The power supply circuit is a circuit that converts an AC voltage into a DC voltage. Also, white has a color temperature of 4200K and day white has a color temperature of 5000K. The lighting device may have a color filter.

[0148] In addition, the lighting device according to the present embodiment may have a heat radiating part. The heat radiating part releases the heat inside the device to the outside of the device, and examples thereof include a metal with a high specific heat and liquid silicon.

[0149] FIG. 7(b) is a schematic view of an automobile which is an example of a moving body according to the present embodiment. The automobile has a tail lamp which is an example of a lighting device. The automobile 1500 may have a tail lamp 1501 and may be configured to light the tail lamp when a braking operation or the like is performed.

[0150] The tail lamp 1501 may have an organic light-emitting element according to the present embodiment. The tail lamp 1501 may have a protective member for protecting the organic light-emitting element. The protective member has a certain degree of strength and may be made of any material as long as it is transparent, but is preferably made of polycarbonate or the like. A phthalic acid derivative, an acrylonitrile derivative or the like may be mixed into the polycarbonate.

[0151] The automobile 1500 may have a vehicle body 1503 and a window 1502 attached thereto. The window 1502 may be a transparent display as long as it is not a window for checking the front and rear of the automobile. The transparent display may have an organic light-emitting element according to the present embodiment. In this case, constituent materials such as electrodes of the organic light-emitting element are made of transparent members.

[0152] The moving body according to the present embodiment may be a ship, an aircraft, a drone or the like. The moving body may have a fuselage and a lighting device provided on the fuselage. The lighting device may emit light for notifying the position of the fuselage. The lighting device has an organic light-emitting element according to the present embodiment.

[0153] With reference to FIG. 8, application examples of the display device of each of the above embodiments will be described. The display device can be applied to a system wearable as a wearable device such as smart glasses, an HMD, or smart contacts. The imaging display device used in such an application example has an imaging device capable of photoelectrically converting visible light and a display device capable of emitting visible light.

[0154] FIG. 8(a) is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention. Using FIG. 8(a), glasses 1600 (smart glasses) according to one application example will be described. An imaging device 1602 such as a CMOS sensor or a SPAD is provided on the front surface side of the lens 1601 of the glasses 1600. Further, a display device of each of the above-described embodiments is provided on the back surface side of the lens 1601.

[0155] The glasses 1600 further include a control device 1603. The control device 1603 functions as a power source that supplies power to the imaging device 1602 and the display device. Further, the control device 1603 controls the operations of the imaging device 1602 and the display device. An optical system for condensing light onto the imaging device 1602 is formed in the lens 1601.

[0156] FIG. 8(b) is a schematic diagram showing another example of a wearable device according to an embodiment of the present invention. Using FIG. 8(b), glasses 1610 (smart glasses) according to one application example will be described. The glasses 1610 have a control device 1612, and an imaging device corresponding to the imaging device 1602 in FIG. 8(a) and a display device are mounted on the control device 1612. An optical system for projecting light emitted from the imaging device and the display device is formed in the lens 1611, and an image is projected onto the lens 1611. The control device 1612 functions as a power source that supplies power to the imaging device and the display device, and controls the operations of the imaging device and the display device.

[0157] The control device 1612 may include a gaze detection unit that detects the wearer's gaze. Infrared light may be used for gaze detection. The infrared light emitting unit emits infrared light toward the eyes of the user who is gazing at the display image. An imaging unit having a light receiving element detects the reflected light of the emitted infrared light from the eyes, thereby obtaining an imaging image of the eyes. By providing a reducing means for reducing the light from the infrared light emitting unit to the display unit in a plan view, a decrease in image quality is reduced. The user's gaze with respect to the display image is detected from the imaging image of the eyes obtained by imaging the infrared light. Any known method can be applied to gaze detection using the imaging image of the eyes. As an example, a gaze detection method based on the Purkinje image by reflection of the irradiation light on the cornea can be used. More specifically, gaze detection processing based on the corneal reflection method is performed. Using the corneal reflection method, a gaze vector representing the orientation (rotation angle) of the eyes is calculated based on the image of the pupil and the Purkinje image included in the imaging image of the eyes, thereby detecting the user's gaze.

[0158] The display device according to an embodiment of the present invention 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 visual field region that the user gazes at and a second visual field region other than the first visual field region based on the gaze information. The first visual field region and the second visual field region may be determined by the control device of the display device, or the display device may receive those determined by an external control device. In the display area of the display device, the display resolution of the first visual field region may be controlled to be higher than the display resolution of the second visual field region. That is, the resolution of the second visual field region may be made lower than that of the first visual field region.

[0159] In addition, the display area has a first display area and a second display area different from the first display area, and based on the line-of-sight information, an area with a higher priority is determined from the first display area and the second display area. The first field of view area and the second field of view area may be determined by the control device of the display device, or may be received from an external control device. The resolution of the area with a higher priority may be controlled to be higher than the resolution of the areas other than the area with a higher priority. That is, the resolution of the area with a relatively low priority may be lowered.

[0160] Note that AI may be used to determine the first field of view area and the area with a higher priority. AI may be a model configured to estimate the angle of the line of sight and the distance to the target at the tip of the line of sight from the image of the eyeball, using the image of the eyeball and the direction in which the eyeball in the image is actually looking as teacher data. The AI program may be possessed by the display device, the imaging device, or an external device. When an external device possesses it, it is transmitted to the display device via communication.

[0161] When performing display control based on visual recognition detection, it is preferably applied to smart glasses further having an imaging device for imaging the outside. The smart glasses can display the imaged external information in real time.

[0162] FIG. 9(a) is a schematic diagram showing an example of an image forming apparatus according to the present embodiment. The image forming apparatus 40 is an electrophotographic image forming apparatus, and has a photoreceptor 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transferrer 32, a conveyance roller 33, and a fixing unit 35. Light 29 is emitted 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 has an organic light emitting element according to the present embodiment. The developing unit 31 has toner and the like. The charging unit 30 charges the photoreceptor 27. The transferrer 32 transfers the developed image onto a recording medium 34. The conveyance roller 33 conveys the recording medium 34. The recording medium 34 is, for example, paper. The fixing unit 35 fixes the image formed on the recording medium 34.

[0163] Figures 9(b) and 9(c) are diagrams showing the exposure light source 28, and are schematic diagrams showing a state in which a plurality of light emitting portions 36 are arranged on a long substrate. Arrow 37 represents the column direction in which the organic light emitting elements are arranged. This column direction is the same as the direction of the axis around which the photoreceptor 27 rotates. This direction can also be called the major axis direction of the photoreceptor 27. Figure 9(b) shows a form in which the light emitting portion 36 is arranged along the major axis direction of the photoreceptor 27. Figure 9(c) shows a form different from that of Figure 9(b), in which the light emitting portions 36 are alternately arranged in the column direction in each of the first column and the second column. The first column and the second column are arranged at different positions in the row direction. In the first column, a plurality of light emitting portions 36 are arranged at intervals. The second column has a light emitting portion 36 at a position corresponding to the interval between the light emitting portions 36 in the first column. That is, also in the row direction, a plurality of light emitting portions 36 are arranged at intervals. The arrangement in Figure 9(c) can also be described as, for example, a state of being arranged in a grid pattern, a state of being arranged in a staggered grid, or a checkered pattern.

[0164] As described above, by using the device using the organic light emitting element according to the present embodiment, it is possible to obtain a good image quality and a stable display even for a long-time display.

Example

[0165] Hereinafter, the present invention will be described by way of examples. However, the present invention is not limited thereto. [Example 1 (Synthesis of Exemplary Compound B-1)] Exemplary compound B-1 was synthesized according to the following scheme.

[0166]

Chemical formula

[0167] (1) Synthesis of Compound m-3 The following reagents and solvents were charged into a 500 ml eggplant flask. Compound m-1: 5.0 g (18.2 mmol) Compound m-2: 3.4 g (21.8 mmol) Sodium carbonate: 15.1 g (10.9 mmol) Toluene: 150 ml Pure water: 75 ml Ethanol: 150 ml Pd(PPh3)4: 210 mg Next, the reaction solution was heated and stirred at 100 °C for 7 hours under a nitrogen stream. After completion of the reaction, 100 ml of water was added and filtration was performed. The obtained solid was purified by silica gel column chromatography (toluene: ethyl acetate mixture) to obtain 4.5 g of m-3 (yield: 81%).

[0168] (2) Synthesis of Compound B-1 The following reagents and solvents were charged into a 200 ml eggplant flask. Compound m-3: 1.5 g (4.9 mmol) Compound m-4: 1.2 g (5.9 mmol) Sodium tert-butoxide: 1.41 g (14.7 mmol) Pd(dba)2: 280 mg xphos: 700 mg Ortho-xylene: 75 ml Next, the reaction solution was heated and stirred at 140 °C for 5 hours under a nitrogen stream. After completion of the reaction, filtration through celite was performed and the solution was concentrated to dryness. The obtained solid was purified by silica gel column chromatography (toluene: ethyl acetate mixture) to obtain 1.3 g of B-1 (yield: 59%).

[0169] For the exemplified compound B-1, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker). [MALDI-TOF-MS] Measured value: m / z = 465 Calculated value: C 33 H 23 NO2 = 465

[0170] [Examples 2 to 16 (Synthesis of Exemplified Compounds)] As shown in Tables 1 to 3, for the exemplified compounds shown in Examples 2 to 16, the exemplified compounds were synthesized in the same manner as in Example 1, except that starting material m-1 in Example 1 was changed to starting material 1, starting material m-2 was changed to starting material 2, and m-4 was changed to starting material 3. Also shown are the measured values of the mass spectrometry results: m / z measured in the same manner as in Example 1.

[0171]

Table 1

[0172]

Table 2

[0173]

Table 3

[0174] [Example 17] In this example, an organic EL element having a bottom emission type structure in which an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode were sequentially formed on a substrate was fabricated.

[0175] First, ITO was deposited on a glass substrate, and an ITO electrode (anode) was formed by performing a desired patterning process. At this time, the film thickness of the ITO electrode was set to 100 nm. The substrate on which the ITO electrode was thus formed was used as an ITO substrate in the following steps. Next, vacuum evaporation by resistance heating in a vacuum chamber was performed to continuously form the organic compound layers and electrode layers shown in Table 4 on the ITO substrate. At this time, the electrode area of the opposing electrode (metal electrode layer, cathode) was 3 mm 2 so as to be. The "ratio %" in Table 4 is a mass ratio.

[0176]

Table 4

[0177] For the obtained device, the characteristics of the device were measured and evaluated. As the initial characteristics regarding light emission, green light emission with a maximum external quantum efficiency (E.Q.E.) of 5.0% was obtained. Specifically, the current-voltage characteristics were measured with a Keithley 4140B picoammeter manufactured by Hewlett-Packard Company, and the emission luminance was measured with a BM7 manufactured by Topcon Corporation. Furthermore, a continuous driving test was conducted at a current density of 50 mA / cm 2 ², and when the time (LT95) when the luminance degradation rate reached 5% was measured, it was 105 hours.

[0178] [Examples 18 to 22] In Example 17, an organic light-emitting device was fabricated in the same manner as in Example 17, except that the compounds shown in Table 5 were appropriately changed. For the obtained device, the characteristics of the device were measured and evaluated in the same manner as in Example 17. The measurement results are shown in Table 5.

[0179] [Table 5]

[0180] [Example 23] An organic light-emitting device was fabricated in the same manner as in Example 17, except that the organic compound layer and the electrode layer shown in Table 6 were continuously formed. The "ratio %" in Table 6 is the mass ratio.

[0181] [Table 6]

[0182] For the obtained device, the characteristics of the device were measured and evaluated in the same manner as in Example 17. As the initial characteristics regarding light emission, green light emission with a maximum external quantum efficiency (E.Q.E.) of 6.3% was obtained. Furthermore, a continuous driving test was conducted at a current density of 50 mA / cm 2 ², and when the time (LT95) when the luminance degradation rate reached 5% was measured, it was 136 hours.

[0183] [Examples 24 to 41, Comparative Examples 1 to 2] In Example 23, an organic light-emitting device was fabricated in the same manner as in Example 23, except that the compounds shown in Table 7 were appropriately modified. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 23. The measurement results are shown in Table 7. Note that Comparative Compound 1 and Comparative Compound 2 are Comparative Compound 1 shown in FIG. 1, and Comparative Compound 2 shown in FIG. 1, respectively.

[0184]

Table 7

[0185] From Table 7, the maximum external quantum efficiencies (E.Q.E.) of Comparative Example 1 and Comparative Example 2 are as low as 4.9% and 3.9%. This is because the difference between S1 and T1 is large, resulting in a small luminescence component due to delayed fluorescence. On the other hand, in the devices of Examples 24 to 41, the difference between S1 and T1 is small due to the substitution of an amino group, which is an electron-donating group with a steric hindrance group X2 and a carbonyl group, which is an electron-withdrawing group, and high-efficiency luminescence is exhibited due to luminescence by delayed fluorescence.

[0186] In addition, the 5% degradation life (LT95) of Comparative Example 1 was 89 hours, and the durability characteristics were poor. This is presumably because the molecular aspect ratio is large, so molecular aggregation is likely to occur, the film property is poor, and the compound is easy to crystallize. On the other hand, in the devices of Examples 24 to 41, the 5% degradation life (LT95) is 95 hours or more, and the durability characteristics are good. This is presumably because the basic skeleton has high planarity and has an amino group having X2 as a substituent that reduces the molecular planarity, so that the molecular aspect ratio becomes small and a highly amorphous film is formed, showing good durability characteristics.

Explanation of Symbols

[0187] 1: Interlayer insulating layer, 2: First electrode, 3: Insulating layer, 4: Organic compound layer, 5: Second electrode, 6: Protective layer, 7: Color filter, 10: Sub-pixel, 11: Substrate, 12: Insulating layer, 13: Gate electrode, 14: Gate insulating film, 15: Semiconductor layer, 16: Drain electrode, 17: Source electrode, 18: TFT, 19: Insulating film, 20: Contact hole, 21: Anode, 22: Organic compound layer, 23: Cathode, 24: First protective layer, 25: Second protective layer, 26: Organic light-emitting element, 100: Display device

Claims

1. An organic compound characterized by being represented by the following general formula [1]. 【Chemical Formula 1】 In general formula [1], R 1 to R 8 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a silyl group, and a cyano group. X 1 represents any one of oxygen, sulfur, selenium, tellurium, and a CR 9 R 10 group. R 9 and R 10 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a silyl group, and a cyano group. However, at least one of the above R 1 to R 8 is a group represented by the following general formula [2]. 【Chemical Formula 2】 In general formula [2], R 11 to R 15 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a silyl group, and a cyano group. *1 represents the bonding position. However, the above R 11 to R 15At least one of them is a specific amino group among the amino groups represented by the following general formulas [3-1] to [3-30], and the specific amino group is an amino group represented by the following general formulas [3-1] to [3-5], [3-7] to [3-10], [3-13] to [3-16], [3-19] to [3-22], or [3-25] to [3-28]. The amino groups represented by the general formulas [3-1] to [3-30] may further have substituents. 【Chemical Formula 3】 In the general formulas [3-1] to [3-30], X 2 is independently selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, and a substituted or unsubstituted naphthyl group. *2 represents the bonding position.

2. The organic compound according to claim 1, wherein the specific amino group is an amino group represented by the general formulas [3-1] to [3-5], [3-7], [3-13], [3-14], [3-25], [3-27], or [3-28].

3. The R 1 to R 4 and the R 5 to R 8 At least one of one side is a group represented by the general formula [2]. The organic compound according to claim 1 or 2.

4. The R 1 to R 4 and the R 5 to R 8 The other side is selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, and a cyano group. The organic compound according to claim 3.

5. The X 1 is oxygen or sulfur. The organic compound according to any one of claims 1 to 4.

6. The R 11 and R 12, R 14 , R 15 At least one of them is the specific amino group, and the organic compound according to any one of claims 1 to 5.

7. The above R 13 is selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted phenyl group, and the organic compound according to claim 6.

8. The above X 2 is a substituted or unsubstituted alkyl group, and the organic compound according to any one of claims 1 to 7.

9. The substituents that the amino group represented by the general formulas [3-1] to [3-30] may further have are a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, a tertiary butyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a pyrazyl group, a triazyl group, a dimethylamino group, a diethylamino group, a dibenzylamino group, a diphenylamino group, a ditolylamino group, a methoxy group, an ethoxy group, a propoxy group, a phenoxy group, fluorine, chlorine, bromine, iodine, and a cyano group, and the organic compound according to any one of claims 1 to 8.

10. An anode and a cathode, In an organic light-emitting device having an organic compound layer disposed between the anode and the cathode, At least one layer of the organic compound layer has the organic compound according to any one of claims 1 to 9, and the organic light-emitting device.

11. The layer having the organic compound is a light-emitting layer, and the organic light-emitting device according to claim 10.

12. The light-emitting layer further has a host material, and the organic light-emitting device according to claim 11.

13. The organic light-emitting device according to claim 12, wherein the host material is a hydrocarbon compound.

14. The organic light-emitting device according to claim 12 or 13, wherein the light-emitting layer further has a light-emitting material.

15. The organic light-emitting device according to claim 14, wherein the light-emitting material is a hydrocarbon compound.

16. The organic light-emitting device according to any one of claims 11 to 15, wherein the light-emitting layer emits green light or red light.

17. A display device having a plurality of pixels, wherein at least one of the plurality of pixels has the organic light-emitting device according to any one of claims 10 to 16 and an active element connected to the organic light-emitting device.

18. An optoelectronic conversion device having an optical unit having a plurality of lenses, an imaging element that receives light that has passed through the optical unit, and a display unit that displays an image captured by the imaging element, wherein the display unit has the organic light-emitting device according to any one of claims 10 to 16.

19. An electronic device having a display unit having the organic light-emitting device according to any one of claims 10 to 16, a housing in which the display unit is provided, and a communication unit provided in the housing and communicating with the outside.

20. An illumination device having a light source having the organic light-emitting device according to any one of claims 10 to 16 and a light diffusing unit or an optical filter that transmits light emitted by the light source.

21. A moving body having a lighting fixture having the organic light-emitting device according to any one of claims 10 to 16 and a body in which the lighting fixture is provided.

22. An exposure light source for an electrophotographic image forming apparatus, comprising the organic light-emitting element according to any one of claims 10 to 16.

Images