Organic compound, organic light-emitting element, display device, photoelectric conversion device, electronic device, lighting device, and mobile body

Abstract

To provide an organic compound excellent in luminous efficiency.SOLUTION: An organic compound represented by general formula [1] in the figure is provided. In general formula [1], R1 to R6 are each independently selected from among a hydrogen atom and substituents represented by general formulas [2]-[18]; at least one of R1 and R2 is a hydrogen atom; at least one of R3 and R4 is a hydrogen atom; and at least one of R5 and R6 is a hydrogen atom.SELECTED DRAWING: Figure 1

Description

Technical Field

[0001] The present invention relates to an organic compound, an organic light-emitting element, a display device, a photoelectric conversion device, an electronic device, a lighting device, and a moving body.

Background Art

[0002] An organic light-emitting element (hereinafter sometimes referred to as an "organic electroluminescence element" or an "organic EL element") is an electronic element 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 element emits light.

[0003] Recent progress in organic light-emitting elements has been remarkable, and its features include low driving voltage, various emission wavelengths, high-speed responsiveness, and the ability to make the light-emitting device thinner and lighter.

[0004] Regarding the improvement of the efficiency of organic light-emitting elements, elements using high-efficiency materials such as phosphorescent materials and delayed fluorescence materials have been reported. Compound A-1 below is described in Patent Document 1. Further, Compound A-2 below is described in Patent Document 2.

Chemical Formula

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0006] When the compound A-1 described in Patent Document 1 or the compound A-2 described in Patent Document 2 is used in the light-emitting layer of an organic light-emitting device, there are still problems with the luminous efficiency.

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

Means for Solving the Problems

[0008] The organic compound as one aspect of the present invention is characterized by being represented by the following general formula [1].

Chemical formula

[18] , and R 1 ~R 6 are such that at least one is a substituent represented by the following general formulas [2] to

[18] . However, one of R 1 or R 2 is a substituent represented by the following general formulas [2] to

[18] , and one of R 3 or R 4 is a substituent represented by the following general formulas [2] to

[18] . R 1 and R 2 are such that at least one of them is a hydrogen atom or a hydrocarbon group. R 3 and R 4 are such that at least one of them is a hydrogen atom or a hydrocarbon group. R 5 and R 6 are such that at least one of them is a hydrogen atom.

Effects of the Invention

[0009] When the compound of the present invention is used in an organic light-emitting device, an organic compound having excellent luminous efficiency can be provided.

Brief Description of the Drawings

[0010]

Figure 1

Figure 2

Figure 3

[0011] (b) It is a schematic view showing an example of a portable device according to an embodiment of the present invention.

Figure 4

[0012] (b) It is a schematic view showing an example of a foldable display device.

Figure 5

[0013] (b) It is a schematic view showing an automobile which is an example of a moving body according to an embodiment of the present invention.

Embodiments for Carrying Out the Invention

[0014] ≪Organic Compound≫ First, the organic compound according to the present embodiment will be described. The organic compound according to the present embodiment is represented by the following general formula [1].

Chemical formula

[18] , and R 1 ~R 6 are such that at least one is a substituent represented by the following general formulas [2] to

[18] . R 1 and R 2 are such that at least one of them is a hydrogen atom or a hydrocarbon group. R 3 and R4 is such that at least one of them is a hydrogen atom or a hydrocarbon group. R 5 and R 6 is such that at least one of them is a hydrogen atom or a hydrocarbon group.

[0015] In other words, in the general formula [1], R 1 and R 2 are such that one of them is a hydrogen atom or a hydrocarbon group.

[0016] In the general formula [1], when any one of R 1 to R 6 is a hydrocarbon group, it is preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms. That is, in the general formula [1], R 1 to R 6 are preferably substituents independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and a substituent represented by the following general formulas [2] to

[18] . [Chemical formula] In the general formulas [2] to

[18] , X 1 and X 2 are substituents independently selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. In the general formulas [2] to

[18] , X 1 and X 2 are preferably substituents independently selected from a substituted or unsubstituted alkyl group having 6 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and a substituted or unsubstituted heterocyclic group having 3 to 9 carbon atoms.

[0017] X 1 and X 2Suitable alkyl groups include, for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, tertiary butyl group, secondary butyl group, cyclohexyl group, etc., but are not limited thereto. Among them, X 1 and X 2 Preferably, the alkyl group has 1 to 6 carbon atoms and is a methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, tertiary butyl group, secondary butyl group, or cyclohexyl group.

[0018] X 1 and X 2 Suitable aryl groups include, for example, phenyl group, naphthyl group, indenyl group, etc., but are not limited thereto. Among them, X 1 and X 2 Preferably, the aryl group has 6 to 10 carbon atoms and is a phenyl group, naphthyl group, or indenyl group.

[0019] X 1 and X 2 Suitable heterocyclic groups include, for example, pyridyl group, pyrimidyl group, pyrazyl group, triazyl group, quinolinyl group, isoquinolinyl group, indolyl group, benzofuranyl group, benzothiophenyl group, etc., but are not limited thereto. Among them, X 1 and X 2 Preferably, the heterocyclic group has 3 to 9 carbon atoms and is a pyridyl group, pyrimidyl group, pyrazyl group, triazyl group, quinolinyl group, isoquinolinyl group, indolyl group, benzofuranyl group, or benzothiophenyl group.

[0020] X 1 and X 2 Examples of the substituents that the alkyl group, aryl group, and heterocyclic group represented by X

[0021] 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 following reaction schemes 1 to 3. [Chemical formula] [Chemical formula] [Chemical formula]

[0022] Here, the substituent Gr in the above reaction schemes 1 to 3 is a substituent selected from the group of substituents represented by the above general formulas [2] to

[18] . In the above reaction schemes 1 to 3, by appropriately changing the compound represented by Gr-H, various compounds with different substituents Gr can be obtained. Note that the synthesis method is not limited to these. The synthesis method will be described in detail in the examples.

[0023] Next, the organic compound according to the present embodiment has the following characteristics. By using the organic compound according to the present embodiment in an organic light-emitting device, an organic light-emitting device with high-efficiency light emission and excellent driving durability characteristics can be provided. The basic skeleton in the present embodiment refers to the R of the compound represented by the general formula [1] 1 ~R 6 is a skeleton in which all are hydrogen atoms. The skeleton in which all of R of the compound represented by the general formula [1] 1 ~R 6 are hydrogen atoms is also referred to as a hexaazatriphenylene skeleton.

[0024] (1) Having an electron-withdrawing hexaazatriphenylene skeleton as the basic skeleton, and further, at least one of R 1 ~R 6 is an electron-donating substituent represented by the general formulas [2] to

[18] , so that the energy gap between S 1 and T 1 is small.

[0025] (2) The substituents of the hexaazatriphenylene skeleton, which is a basic skeleton having a highly planar structure, are substituents represented by general formulas [2] to

[18] with relatively large steric hindrance, so that molecular association is unlikely to occur.

[0026] (3) Due to the structure in which the substituents represented by general formulas [2] to

[18] are arranged in a sterically twisted manner with respect to the hexaazatriphenylene skeleton as the basic skeleton, the S 1 energy level becomes a preferable level as a material for the green and red light-emitting layers.

[0027] Hereinafter, the above characteristics will be described.

[0028] (1) It has an electron-withdrawing hexaazatriphenylene skeleton as the basic skeleton, and furthermore, R 1 ~R 6 At least one of them is an electron-donating substituent represented by general formulas [2] to

[18] , so that the energy gap between S 1 and T 1 is small.

[0029] In creating the organic compound represented by general formula [1], the present inventors focused on the electron distributions of the HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) of the compound.

[0030] As shown in Table 1, in exemplary compounds B-1 and B-2, 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.

[0031] This means that the overlap integral is small, leading to a small energy difference between the singlet excited state (S 1 ) and the triplet excited state (T 1 ). Specifically, the energy gaps (ΔST) between S 1 and T 1 of exemplary compounds B-1 and B-2 are as small as 0.17 eV and 0.17 eV, respectively. On the other hand, the S of comparative compounds a-1 to a-41 and T 1 The energy gaps (ΔST) of are 0.36 eV, 0.36 eV, 0.36 eV, and 0.52 eV, respectively, which are large.

[0032] The above characteristics are due to the effect that the compound of the present embodiment having a nitrogen-containing condensed ring skeleton which is electron-withdrawing as a basic skeleton, having an electron-donating amino group as a substituent, and the amino group as a substituent being twisted with respect to the basic skeleton. The substituents of the compound of the present embodiment represented by the general formula [1] are represented by the general formulas [2] to

[18] . However, the general formulas [2] to

[18] further have substituents X 1 and X 2 having. Substituent X 1 and X 2 are arranged at positions near the bonding position where the entire substituent represented by the general formulas [2] to

[18] bonds to the basic skeleton and where steric hindrance can occur between the basic skeleton. In the present embodiment, since the substituents X 1 and X 2 are any of an alkyl group, an aryl group, and a heterocyclic group, the substituents represented by the general formulas [2] to

[18] cause a relatively large steric hindrance between the basic skeleton. The hexaazatriphenylene skeleton as the basic skeleton has a highly planar structure. However, due to the above-mentioned steric hindrance, the substituents represented by the general formulas [2] to

[18] are twisted with respect to the basic skeleton. That is, the compound represented by the general formula [1] has a structure in which the plane in which the substituents represented by the general formulas [2] to

[18] exist and the plane in which the hexaazatriphenylene skeleton as the basic skeleton exists are not parallel but intersect.

[0033] On the other hand, the comparative compounds a-1 to a-3 and the comparative compounds A-1 to A-2 also have a structure in which the hexaazatriphenylene skeleton as the basic skeleton has an amino group as a substituent. However, the substituents of these comparative compounds do not have substituents that cause a relatively high steric hindrance such as the substituents represented by the general formulas [2] to

[18] . More specifically, the substituents of the comparative compounds a-1 to a-3 and the comparative compounds A-1 to A-2 are the substituents X 1 and X 2The portion corresponding to is unsubstituted, i.e., it is a hydrogen atom. Therefore, since no steric hindrance occurs like the substituents represented by general formulas [2] to

[18] , comparative compounds a-1 to a-3 and comparative compounds A-1 to A-2 adopt a structure in which the plane where the substituent exists and the plane where the basic skeleton exists are parallel. That is, the basic skeleton and the substituent do not adopt a three-dimensionally twisted structure. Therefore, as also shown in Table 1, in exemplary compounds a-1 to a-3 and comparative compounds A-1 to A-2, the portion occupying the electron orbital distribution of HOMO and the portion occupying the electron orbital distribution of LUMO are not separated, and the overlap between HOMO and LUMO is large. For this reason, 1 S and 1 T have a large energy gap.

Table 1

[0034] Incidentally, 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 *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.). Hereinafter, the molecular orbital calculations in this specification were carried out by the same method.

[0035] Thus, the compound of this embodiment represented by the general formula [1] is S1 and T 1 is characterized in that the energy difference (ΔST) between S and T is small. Thus, when the compound of the present embodiment is used in the light-emitting layer of an organic light-emitting device, an element with high-efficiency light emission can be provided. The reason is that S 1 and T 1 For excitons generated with a singlet exciton to triplet exciton ratio of 1:3 due to the small energy difference between S and T, the triplet excitons that were usually thermally deactivated can be used for delayed fluorescence-type light emission that emits light from the singlet excited state. For reverse intersystem crossing that converts triplet excitons to singlet excited states, S 1 and T 1 It is advantageous that the smaller the energy difference between S and T, the smaller the energy barrier. Since the compound of the present embodiment meets that condition and is advantageous, an element with high-efficiency light emission can be provided.

[0036] (2) The substituents of the hexaazatriphenylene skeleton, which is a basic skeleton having a highly planar structure, are substituents represented by general formulas [2] to

[18] with relatively large steric hindrance, so that molecular aggregation hardly occurs.

[0037] In creating the organic compound represented by general formula [1], the present inventors focused on the planarity of the compound. The basic skeleton of the compound of the present embodiment is a hexaazatriphenylene skeleton, which has a highly planar structure. High planarity means that stacking of molecules easily occurs. In other words, it is not preferable because molecular aggregation easily occurs. This is because in an organic light-emitting device, molecular aggregation causes a decrease in efficiency due to concentration quenching. Also, it is disadvantageous for reverse intersystem crossing. This is because exciton annihilation (TTA) due to energy transfer of triplet excitons occurring between molecules easily occurs, and reverse intersystem crossing to singlet excitons hardly occurs.

[0038] As described above, the compound represented by the general formula [1] has a structure in which the substituents represented by the general formulas [2] to

[18] are sterically twisted with respect to the basic skeleton. Therefore, the substituents represented by the general formulas [2] to

[18] can disrupt the high planarity of the basic skeleton. Therefore, the compound represented by the general formula [1] has relatively low planarity, making it difficult for molecules to stack and for molecular aggregation to occur, which is preferable. Therefore, when the compound of the present embodiment is used in the light-emitting layer of an organic light-emitting device, molecular aggregation is less likely to occur, so concentration quenching is less likely to occur, and an organic light-emitting device with high-efficiency light emission can be obtained.

[0039] Also, the above characteristics are effective in improving the amorphousness of organic compounds. When the compound of the present embodiment is used in the organic layer (organic compound layer) of an organic light-emitting device, it is difficult to crystallize and a stable amorphous film can be formed. As a result, it is preferable for obtaining an organic light-emitting device with excellent high durability that does not crystallize even when driven for a long time.

[0040] Furthermore, the above characteristics also have the effect of improving sublimability. Improving sublimability enables high purification of materials by sublimation purification and fabrication of organic light-emitting devices by vapor deposition. As a result, 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.

[0041] (3) By having a structure in which the substituents represented by the general formulas [2] to

[18] are sterically twisted with respect to the hexaazatriphenylene skeleton, which is the basic skeleton, S 1 the energy level becomes a preferable level as a material for green and red light-emitting layers.

[0042] Exemplary compound B-1, which is one of the compounds represented by the general formula [1], has a structure in which the 1-position and 8-position of the carbazole group, which is an amino substituent, are substituted with methyl groups when compared with comparative compound a-1. As a result, as described above, the amino substituent has a structure that is sterically twisted with respect to the basic skeleton. The S of comparative compound a-1 1The energy level of [Compound Name] is 424 nm, while the S of Exemplary Compound B-1 1 has an energy level of 488 nm. That is, Exemplary Compound B-1 is a compound with an emission wavelength that is about 64 nm longer than that of Comparative Compound a-1, and can provide a compound advantageous as a green light-emitting material. Further, by further increasing the amino substituents, the S 1 energy level becomes even lower, and the emission wavelength can be changed in a direction advantageous as a green light-emitting material or a red light-emitting material. Therefore, the compound represented by General Formula [1] is preferable as a green light-emitting material or a red light-emitting material.

[0043] Furthermore, the compound of the present invention is preferably used in the light-emitting layer of an organic light-emitting device, and in that case, has the following characteristics.

[0044] (4) 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.

[0045] (5) 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.

[0046] (6) When the light-emitting material is a compound composed of hydrocarbons, a highly efficient and long-lasting light-emitting device is provided Hereinafter, the characteristics (4) to (6) will be described.

[0047] (4) 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.

[0048] The compound of this embodiment is a compound having a nitrogen-containing heterocyclic group with electron-withdrawing properties and an amino group with electron-donating properties. Therefore, by mixing with a host material in the light-emitting layer of an organic light-emitting device, due to the contribution of electron-withdrawing properties, a light-emitting layer with electron-trapping properties, or due to the contribution of electron-donating properties, a hole-trapping light-emitting layer is formed.

[0049] Therefore, electrons or 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), the compound of this embodiment has S 1 and T 1 Since the energy difference between them is small, delayed fluorescence-type emission is efficiently generated in the light-emitting layer, and more triplet excitons can be utilized for emission.

[0050] In particular, when the host material is a hydrocarbon compound, the LUMO of the compound of this embodiment tends to be at a lower level (far from the vacuum level) than the host material, or the HOMO of the compound of this embodiment tends to be at a higher level (close to the vacuum level) than the host material. Therefore, it is easier to trap electrons and holes, and the effect is significant. A hydrocarbon compound is a compound composed only of carbon and hydrogen in its molecule.

[0051] Furthermore, as described in (2), the compound of this embodiment is less likely to cause molecular aggregation, so concentration quenching is less likely to occur in the host material. This effect leads to preventing quenching due to the interaction between excitons when the compound of this embodiment is in an excited state, and is effective in efficiently generating delayed fluorescence-type emission in the light-emitting layer.

[0052] (5) By mixing the compound of this embodiment with a host material in the light-emitting layer and further having a light-emitting material, a light-emitting device with high efficiency and high color purity is provided.

[0053] The compound of the present 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 more efficient and high-color-purity light-emitting device. In this case, since the compound of the present embodiment facilitates exciton recombination, it is necessary to configure it at a concentration that can preferentially trap electrons and holes in the light-emitting layer. Therefore, the concentration of the compound of the present embodiment is preferably 0.1% by mass or more and 45% by mass or less, more preferably 1% by mass or more and 35% by mass or less, and particularly preferably 10% by mass or more and 30% by mass or less with respect to the entire light-emitting layer. Furthermore, the concentration of the compound of the present embodiment may be 15% by mass or more with respect to the entire light-emitting layer. On the other hand, when the compound of the present embodiment is regarded as a light-emitting material, a lower doping concentration is preferable because it is less affected by concentration quenching due to intermolecular interaction and changes in the emission spectrum. Therefore, it is preferable to dope a light-emitting material other than the compound of the present embodiment in the light-emitting layer. The doping concentration of the light-emitting material to be further doped in the light-emitting layer 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, and still more preferably 10% by mass or less. As described above, a highly efficient and high-color-purity light-emitting device can be provided. Furthermore, as the light-emitting material, green and red light-emitting materials are preferable. This is because the compound of the present embodiment is a green light-emitting material.

[0054] (6) When the light-emitting material used together with the compound of the present embodiment is a compound composed of hydrocarbons, a light-emitting device with high efficiency and good durability characteristics is provided.

[0055] Since the compound of the present embodiment has a strongly electron-withdrawing nitrogen-containing heterocyclic group, as described in (5) above, the luminescent material used by doping and together with the compound preferably has no amino group which is an electron-donating group, and a compound composed of hydrocarbons is preferable. The reason is as follows. When a luminescent material having an amino group is used together with the compound of the present embodiment, the nitrogen-containing heterocyclic group of the compound of the present embodiment and the luminescent material having an amino group interact with each other in the light-emitting layer. As a result, there is a possibility that the luminous efficiency decreases due to the formation of an exciplex, or the color purity of the light-emitting element deteriorates due to a change in the emission spectrum of the luminescent material.

[0056] Therefore, the luminescent material used together with the compound of the present embodiment 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 that is less likely to be oxidized due to a higher ionization potential. A hydrocarbon compound is a compound composed only of carbon and hydrogen in the molecule.

[0057] As described above, an organic light-emitting device with high-efficiency light emission can be obtained by mixing the compound of the present embodiment with a host material in the light-emitting layer. At this time, the luminescent material may be the compound of the present embodiment, and further, a luminescent material may be mixed and the compound of the present embodiment may function as an assist material. By using a luminescent 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 the efficiency is greatly preferable.

[0058] Specific examples of the organic compound according to the present invention are shown below. However, the present invention is not limited thereto.

Chemical formula

Chemical formula

Chemical formula

[0059] Those belonging to Group C are monosubstituted compounds (monosubstituted forms) in which, in the compound represented by the general formula [1], any one of R 1 ~R 6 is a substituent represented by the general formulas [2] to

[18] , and the rest are all hydrogen atoms. Since it is a monosubstituted form, ΔST (S 1 -T 1 difference) becomes small, and delayed fluorescence-type emission is likely to occur. The substituents represented by the general formulas [2] to

[18] are electron-donating substituents, and the LUMO is distributed in the substituents represented by the general formulas [2] to

[18] in the compound represented by the general formula [1]. Since the compounds belonging to Group C are monosubstituted forms, the number of substituents where the LUMO is distributed is small, the thermal vibration deactivation that can occur at the bonding site between the basic skeleton and the substituent is suppressed, and delayed fluorescence-type emission is more easily obtained.

[0060] Those belonging to Group D are disubstituted compounds (disubstituted forms) in which, in the compound represented by the general formula [1], any two of R 1 ~R 6 are substituents represented by the general formulas [2] to

[18] , and the rest are all hydrogen atoms. More specifically, R 1 and R 3 are substituents represented by the general formulas [2] to

[18] , and R 2 , and, R 4 ~R 6 may be hydrogen atoms. Since it has two substituents, the steric bulkiness increases compared to the monosubstituted form, the distance between molecules widens, it is difficult to cause molecular aggregation, and concentration quenching is difficult. Also, since ΔST is small as in the monosubstituted form, delayed fluorescence-type emission is easily obtained.

[0061] Those belonging to Group E are in the compound represented by the general formula [1], R 1 ~R 6Among them, any three are substituents represented by general formulas [2] to

[18] , and the rest are all hydrogen atoms, which is a trisubstituted compound (trisubstituted body). More specifically, R 1 、R 3 、and R 5 are substituents represented by general formulas [2] to

[18] , and R 2 、R 4 、and R 6 may be hydrogen atoms. Since it has three substituents, the planarity of the molecule is smaller than that of the monosubstituted body and the disubstituted body, that is, it is more three-dimensional. Therefore, molecular aggregation is less likely to occur, so concentration quenching is less likely to occur, which is more advantageous when used at high concentrations. In addition, the number of chemical reaction sites of the basic skeleton of hexaazatriphenylene decreases, and the reaction sites are sterically covered by the substituents, so the chemical stability is increased. Thereby, an organic light-emitting device excellent in durability can be realized.

[0062] ≪Organic Light-Emitting Device≫ Next, the organic light-emitting device of this embodiment will be described.

[0063] The organic light-emitting device of this embodiment has at least an anode (anode) and a cathode (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.

[0064] 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, etc. The light-emitting layer may be a single layer or a laminate composed of a plurality of layers.

[0065] 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, etc. 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.

[0066] 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 material of the light-emitting layer, or may be used as a guest material. It may also be used as an assist material that can be included in the light-emitting layer. Here, the host material is the compound having the largest mass ratio among the compounds constituting the light-emitting layer. The guest material is a compound having a mass ratio smaller than that of the host material 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 material among the compounds constituting the light-emitting layer and assisting the emission of the guest material.

[0067] Here, when the organic compound according to the present embodiment is used as a guest material of the light-emitting layer, the concentration of the organic compound according to the present embodiment as the guest material is preferably 0.01% by mass or more and 20% by mass or less with respect to the entire light-emitting layer, and more preferably 0.1% by mass or more and 5% by mass or less. When the organic compound according to the present embodiment is used as an assist material of the light-emitting layer, the concentration of the organic compound according to the present embodiment as the assist material is preferably 0.1% by mass or more and 45% by mass or less with respect to the entire light-emitting layer, and more preferably 1% by mass or more and 30% by mass or less.

[0068] When the organic compound according to the present embodiment is used as a guest material in the light-emitting layer, the mass ratio of the host material to the organic compound as the guest material (host material / guest material) is preferably 1.1 or more and 10,000 or less. Further, the mass ratio is more preferably 2 or more and 1,000 or less, and even more preferably 2 or more and 100 or less.

[0069] When the organic compound according to the present embodiment is used as a guest material in the light-emitting layer, it is preferable to use a material having a higher LUMO than the organic compound according to the present embodiment (a material closer to the vacuum level in terms of LUMO) as the host material. This is because the organic compound according to the present embodiment tends to have a lower LUMO, so by using a material with a higher LUMO than the organic compound according to the present embodiment as the host material, the organic compound according to the present embodiment can receive more electrons supplied to the host material of the light-emitting layer.

[0070] When the organic compound according to the present embodiment is used as a guest material in the light-emitting layer, it is preferable to satisfy the following relationship. Let the energy level of S of the host material be S 1 and the energy level of T of the host material be T h1 , and the energy level of S of the guest material be S 1 and the energy level of T of the guest material be T h1 . When S 1 is S g1 and T 1 is T g1 , it is preferable to satisfy S h1 >S g1 and T h1 >T g1 .

[0071] When using the organic compound according to the present embodiment as an assist material for the light-emitting layer, it is preferable to use a material having a higher LUMO than the organic compound according to the present embodiment (a material having a LUMO closer to the vacuum level) as the guest material. The organic compound according to the present embodiment tends to have a low LUMO. Therefore, by using a material having a higher LUMO than the organic compound according to the present embodiment as the light-emitting material (guest material), the organic compound according to the present embodiment receives more electrons supplied to the host material 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 light-emitting material (guest material). When using the organic compound according to the present embodiment as an assist material for the light-emitting layer, the S 1 material having an energy level lower than that of the organic compound is preferably used as the guest material (light-emitting material).

[0072] The present inventors have conducted various studies and found that when the organic compound according to the present embodiment is used as the host material, guest material, or assist material of the light-emitting layer, particularly as the guest material of the light-emitting layer, an element that exhibits a high-efficiency and high-brightness light output and has extremely high durability can be obtained. Furthermore, it has been found that when used as an assist material for the light-emitting layer, an element that exhibits a high-efficiency and high-brightness light output and has 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 in which a light-emitting layer and another light-emitting layer are laminated, 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-forming method is not particularly limited, and film formation is performed by evaporation or coating film formation. Details of this will be described in detail in the examples described later.

[0073] The organic compound according to the present 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 according to the present 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.

[0074] <Materials Constituting the Organic Light-Emitting Element> Here, as materials constituting the organic light-emitting element, in addition to the organic compounds according to the present embodiment, various conventionally known low molecular weight and high molecular weight compounds can be used as necessary. Typically, a hole injection compound or a hole transport compound, a compound serving as a host material, a light-emitting compound, an electron injection compound or an electron transport compound, etc. can be used together. Examples of these compounds are given below.

[0075] As the hole injection / transport material (hole injection material or hole transport material), a material with a high hole mobility is preferable so as to facilitate the injection of holes from the anode and transport the injected holes to the light-emitting layer. Also, in order to suppress deterioration of the film quality such as crystallization in the organic light-emitting element, a material with a high glass transition temperature is preferable. Examples of low molecular weight and high molecular weight materials having hole injection / 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 / transport materials are also preferably used for the electron blocking layer.

[0076] Specific examples of the compounds used as the hole injection / transport material are shown below, but are of course not limited thereto.

Chemical formula

[0077] Among those listed as the hole injection / 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 elements. HT2, HT3, HT4, HT5, HT6, HT10, and HT12 may be used in the organic compound layer adjacent to HT16. Also, a plurality of materials may be used in one organic compound layer.

[0078] As luminescent materials mainly related to the luminescence function, in addition to the organic compounds represented by the general formula [1], 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-hydroxyquinolato)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.

[0079] Specific examples of the compounds used as luminescent materials are shown below, but of course, they are not limited to these.

Chemical formula

Chemical formula

[0080] When the luminescent material is a hydrocarbon compound, it is preferable because it can prevent the reduction of luminescence efficiency due to exciplex formation and the deterioration of color purity due to the change in the luminescence spectrum of the luminescent material. Here, the hydrocarbon compound is a compound composed only of carbon and hydrogen, and among the specific examples of the compounds used as the above luminescent materials, BD7, BD8, GD5 to GD9, and RD1 correspond.

[0081] When the luminescent material is a condensed polycycle containing a 5-membered ring, it is more preferable because it has a high ionization potential, is difficult to oxidize, and can provide an element with a long and durable life. Among the specific examples of the compounds used as the above luminescent materials, BD7, BD8, GD5 to GD9, and RD1 correspond.

[0082] As the light-emitting layer host material or light-emitting assist material contained in the light-emitting layer, in addition to aromatic hydrocarbon compounds or their derivatives, carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organic aluminum complexes such as tris(8-quinolinolato)aluminum, and organic beryllium complexes can be mentioned.

[0083] Specific examples of the compounds used as the light-emitting layer host material or light-emitting assist material contained in the light-emitting layer are shown below, but of course, they are not limited to these.

Chemical formula

[0084] When the host material is a hydrocarbon compound, since the compound of the present invention is likely to trap electrons and holes, the effect of improving the efficiency is greatly preferable. Here, the hydrocarbon compound is a compound composed only of carbon and hydrogen, and among the specific examples of the compounds used as the above host material, EM1 to EM12 and EM16 to EM27 correspond.

[0085] As the electron transport 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 transport material. Materials having electron transport 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 transport materials are also preferably used in the hole blocking layer.

[0086] Specific examples of the compounds used as the electron transport material are shown below, but of course, they are not limited to these.

Chemical formula

[0087] As the electron injection material, it can be arbitrarily selected from those that enable easy electron injection from the cathode, and is selected in consideration of the balance with hole injection properties, etc. 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, benzimidazolide derivatives, imidazolide derivatives, fulvalene derivatives, and acridine derivatives can be mentioned.

[0088] <Configuration of Organic Light-Emitting Element> The organic light-emitting element 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 and the color filter. The planarization layer can be composed of an acrylic resin or the like.

[0089] [Substrate] As the substrate, a semiconductor substrate such as quartz, glass, or silicon wafer, resin, metal, etc. can be used. Further, a switching element such as a transistor and wiring may be provided on the substrate, and an insulating layer may be provided thereon. As the insulating layer, as long as a contact hole can be formed to ensure conduction between the anode and the wiring and insulation from non-connected wiring can be ensured, the material is not limited. For example, resins such as polyimide, silicon oxide, silicon nitride, etc. can be used.

[0090] [Electrode] As the electrodes, a pair of electrodes can be used. The pair of electrodes may be an anode and a cathode. When an electric field is applied in the direction in which the organic light-emitting element emits light, the electrode with a higher potential is the anode, and the other is the cathode. 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.

[0091] As the anode constituent material, it is preferable to use one with as large a work function as possible. For example, single 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.

[0092] 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.

[0093] 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 it is not limited thereto. For the formation of the electrode, photolithography technology can be used.

[0094] On the other hand, as the cathode constituent material, one with a small work function is preferable. For example, alkali metals such as lithium, alkaline earth metals such as calcium, single metals such as aluminum, titanium, manganese, silver, lead, chromium, etc. or mixtures containing these can be mentioned. Or alloys combining these single 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 be a single - layer structure or a multi - layer structure. Among them, it is preferable to use silver, and in order to suppress the aggregation of silver, it is more preferable to use a silver alloy. As long as the aggregation of silver can be suppressed, the ratio of the alloy does not matter. For example, it may be 1:1.

[0095] The organic light-emitting device may be a top-emission device using an oxide conductive layer such as ITO as the cathode, or a bottom-emission device using a reflective electrode such as aluminum (Al) as the cathode, and is not particularly limited. The method for forming the cathode is not particularly limited, but the DC and AC sputtering methods are more preferable because they provide good film coverage and are likely to reduce resistance.

[0096] [Protective layer] A protective layer may be provided after the formation of the cathode. For example, by bonding glass provided with a moisture absorbent on the cathode, the intrusion of water or the like into the organic compound layer can be suppressed, and the occurrence of display defects can be suppressed. As another embodiment, a passivation film such as silicon nitride may be provided on the cathode to suppress the intrusion of water or the like into the organic EL layer. For example, after the formation of the cathode 7, it may be transported to another chamber without breaking the vacuum, and a silicon nitride film with a thickness of 2 μm may be formed by the CVD method to serve as a protective layer. A protective layer using the atomic layer deposition method (ALD method) may be provided after the film formation by the CVD method.

[0097] [Color filter] A color filter may be provided on the protective layer. For example, a color filter adapted to the size of the organic light-emitting device may be provided on another substrate and bonded to the substrate provided with the organic light-emitting device, or a color filter may be patterned on the protective layer such as silicon oxide using photolithography technology. The color filter may be composed of a polymer.

[0098] [Planarization layer] A planarization layer may be provided between the color filter and the protective layer. The planarization layer may be composed of an organic compound, and may be a low molecule or a polymer, but is preferably a polymer.

[0099] The planarization layer may be provided above and below the color filter, respectively, 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, silicone resin, urea resin, and the like.

[0100] [Counter substrate] A counter substrate may be provided on the planarization 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.

[0101] [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 device according to an embodiment of the present invention are formed by the following method.

[0102] For the organic compound layers constituting the organic light-emitting device according to an embodiment of the present invention, dry processes such as vacuum evaporation, ionization evaporation, sputtering, and plasma can be used. Alternatively, 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 also be used.

[0103] Here, 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 stability over time is excellent. Also, when forming a film by a coating method, a film can be formed in combination with an appropriate binder resin.

[0104] Examples of the binder resin include, but are not limited to, polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, urea resin, and the like.

[0105] 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. Further, if necessary, additives such as known plasticizers, antioxidants, and ultraviolet absorbers may be used in combination.

[0106] <Use of the organic light-emitting device according to this embodiment> The organic light-emitting device according to this embodiment can be used as a component of a display device 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.

[0107] The display device may be an image information processing device having an image input unit for inputting image information from an area CCD, a linear CCD, a memory card, etc., an information processing unit for processing the input information, and a display unit for displaying the input image. The display device may have a plurality of pixels, and at least one of the plurality of pixels may have the organic light-emitting device according to this embodiment and a transistor connected to the organic light-emitting device. At this time, the substrate may be a semiconductor substrate such as silicon, and the transistor may be a MOSFET formed on the substrate.

[0108] In addition, the display unit of 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. Further, the display device may be used for the display unit of a multifunction printer.

[0109] Next, the display device according to this embodiment will be described with reference to the drawings. FIG. 1 is a schematic cross-sectional view showing an example of a display device having an organic light-emitting device and a TFT element connected to this organic light-emitting device. The TFT element is an example of an active element.

[0110] The display device 1 in FIG. 1 is provided with a substrate 11 such as glass, and a moisture-proof film 12 for protecting the TFT element or the organic compound layer on the upper part thereof. On the moisture-proof film 12, a metal gate electrode 13, a gate insulating film 14, and a semiconductor layer 15 are provided.

[0111] 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 is connected to the source electrode 17 through a contact hole 20.

[0112] In addition, the electrical connection method between the electrodes (anode 21, cathode 23) included in the organic light-emitting element and the electrodes (source electrode 17, drain electrode 16) included in the TFT is not limited to the mode shown in FIG. 1. That is, any one of the anode 21 or the cathode 23 and any one of the source electrode 17 or the drain electrode 16 of the TFT element 18 may be electrically connected.

[0113] In the display device 1 of FIG. 1, the organic compound layer 22 is illustrated as if it were a single layer, but the organic compound layer 22 may be a plurality of layers. On the cathode 23, a first protective layer 25 and a second protective layer 24 for suppressing the deterioration of the organic light-emitting element are provided.

[0114] In the display device 1 of FIG. 1, a transistor is used as the switching element, but an MIM element may be used as the switching element instead.

[0115] In addition, the transistor used in the display device 1 of FIG. 1 is not limited to a thin-film transistor having an active layer on an insulating surface of the substrate, and a transistor using a single-crystalline silicon wafer may also be used. 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. In addition, the thin-film transistor is also called a TFT element.

[0116] The transistor included in the display device 1 of FIG. 1 may be formed within a substrate such as an Si substrate. Here, being formed within the substrate means manufacturing the transistor by processing the substrate itself such as an Si substrate. That is, having a transistor within the substrate can also be regarded as the substrate and the transistor being integrally formed.

[0117] In the organic light-emitting element according to the present embodiment, the emission luminance is 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 the present embodiment is not limited to a TFT, and may be a transistor formed of low-temperature polysilicon or an active matrix driver formed on a substrate such as an Si substrate. Being on the substrate can also mean within the substrate. Whether to provide a transistor within 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.

[0118] FIG. 2 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. A transistor is 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 it is a portable device.

[0119] The display device according to this embodiment may be used in a display unit of an imaging device having an optical unit with a plurality of lenses and an imaging element that receives light that has passed through the optical unit. The imaging device may have a display unit that displays information acquired by the imaging element. 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 alternatively referred to as an optoelectronic conversion device.

[0120] FIG. 3(a) is a schematic diagram showing an example of the imaging device according to this embodiment. The imaging device 1100 may have a viewfinder 1101, a rear display 1102, an operation unit 1103, and a housing 1104. The viewfinder 1101 may have the display device according to this 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.

[0121] Since the timing suitable for imaging is a very short time, it is better to display information earlier. Therefore, it is preferable to use the display device using the organic light-emitting element of this 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 suitably used than these devices, such as a liquid crystal display device, for which a display speed is required.

[0122] The imaging device 1100 has an optical unit (not shown). The optical unit has a plurality of lenses and forms an image on an imaging element 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.

[0123] The display device according to this embodiment may have a color filter having red, green, and blue. The red, green, and blue may be arranged in a delta array in the color filter.

[0124] The display device according to this 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 a mobile phone such as a smartphone, a tablet, a head-mounted display, and the like.

[0125] FIG. 3(b) is a schematic diagram showing an example of the electronic device according to this embodiment. The electronic device 1200 has a display unit 1201, an operation unit 1202, and a housing 1203. The housing 1203 may have a circuit, a printed circuit board having the circuit, a battery, and a communication unit. The operation unit 1202 may be a button or a reaction unit of a touch panel method. The operation unit may be a biometric recognition unit that recognizes a fingerprint and performs unlocking or the like. An electronic device having a communication unit may also be referred to as a communication device.

[0126] FIG. 4 is a schematic diagram showing an example of the display device according to this embodiment. FIG. 4(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 this embodiment may be used for the display unit 1302. The display device 1300 has a base 1303 that supports the frame 1301 and the display unit 1302. The base 1303 is not limited to the form of FIG. 4(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 such that the display surface of the display unit 1302 is curved. The radius of curvature may be 5000 mm or more and 6000 mm or less.

[0127] FIG. 4(b) is a schematic diagram showing another example of the display device according to the present embodiment. The display device 1310 in FIG. 4(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.

[0128] FIG. 5(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 film 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 may be a filter that improves the color rendering property of the light source. The light diffusing unit can effectively diffuse the light of the light source, such as lighting up, and deliver the light to a wide range. The optical filter and the light diffusing unit may be provided on the light-emitting side of the lighting. If necessary, a cover may be provided on the outermost side.

[0129] The lighting device is, for example, a device that illuminates a room. The lighting device may emit any color from white, warm white, or other colors from blue to red. It may have a dimming circuit for dimming them or a color mixing circuit for mixing the emission colors. 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 warm white has a color temperature of 5000K. The lighting device may have a color filter.

[0130] 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.

[0131] FIG. 5(b) is a schematic diagram of an automobile which is an example of the mobile 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 turn on the tail lamp when a braking operation or the like is performed.

[0132] 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 EL 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 with the polycarbonate.

[0133] 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.

[0134] The mobile body according to the present embodiment may be a ship, an aircraft, a drone or the like. The mobile body may have a body and a lighting device provided on the body. The lighting device may emit light for notifying the position of the body. The lighting device has an organic light-emitting element according to the present embodiment.

[0135] As described above, by using the device using the organic light-emitting element according to the present embodiment, it is possible to achieve a good image quality and a stable display even for a long-time display.

Example

[0136] Hereinafter, the present invention will be described by way of examples. However, the present invention is not limited thereto.

[0137] <Example 1 (Synthesis of Exemplary Compound C-1)> Exemplary compound C-1 was synthesized according to the following scheme. The following scheme is the reaction scheme in Reaction Scheme 1 described above, where the substituent Gr is the substituent represented by the above general formula [2], and X 1 and X 2 are both methyl groups.

Chemical formula

[0138] (1) Synthesis of compound m-2 The following reagents and solvents were charged into a 200 ml eggplant flask. Compound m-1: 3.0 g Oxalyl dibromide: 3.0 ml Acetic acid: 60 ml Next, the reaction solution was heated under reflux with stirring. After 3 hours, the reaction solution was returned to room temperature, the precipitate was suction filtered, washed with methanol, and then dried under reduced pressure to obtain 5.0 g (yield: 90%) of compound m-2.

[0139] (2) Synthesis of compound m-4 The following reagents and solvents were charged into a 200 ml eggplant flask. Compound m-2: 2.0 g (5.10 mmol) Compound m-3: 1.1 g (5.61 mmol) Sodium tert-butoxide: 0.73 g (7.67 mmol) Pd(dba) 2 : 146 mg (0.52 mmol) Tri-tert-butylphosphine: 318 mg (1.59 mmol) o-Xylene: 60 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 1.95 g (yield: 75%) of yellow solid m-4.

[0140] (3) Synthesis of compound C-1 A 200 ml eggplant flask was charged with the reagents and solvents shown below. Compound m-4: 1.0 g (1.97 mmol) Sodium tert-butoxide: 0.28 g (2.97 mmol) Pd 2 (dba) 3 : 91 mg (0.99 mmol) Tri-tert-butylphosphine: 60 mg (2.96 mmol) o-Xylene: 30 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 carried out, and the solution was concentrated to dryness. The obtained solid was purified by silica gel column chromatography (toluene:ethyl acetate mixture), and 0.67 g (yield: 80%) of yellow solid C-1 was obtained.

[0141] For the obtained yellow solid C-1, mass spectrometry was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker). Mass spectrometry confirmed that the target compound C-1 was successfully synthesized.

[0142] [MALDI-TOF-MS] Measured value: m / z = 429 Calculated value: C 26 H 19 N 7 = 429 <Examples 2 to 11 (Synthesis of Exemplary Compounds)> As shown in Table 2, for the exemplary compounds shown in Examples 2 to 11, the exemplary compounds were synthesized in the same manner as in Example 1, except that the raw material m-3 in Example 1 was changed to Raw Material 1. Also, the measured values (m / z) of the mass spectrometry results measured in the same manner as in Example 1 are summarized in Table 2. [Table 2]

[0143] <Example 12 (Synthesis of Exemplary Compound D-2)> Exemplary compound D-2 was synthesized according to the following scheme. The following scheme is the reaction scheme in Reaction Scheme 2 described above, where the substituent Gr is the substituent represented by the above general formula [3], and X 1 and X 2 are both methyl groups.

Chemical Formula

[0144] (1) Synthesis of Compound m-7 The following reagents and solvents were charged into a 500 ml eggplant flask. Compound m-6 was synthesized via Compound m-5 by the method described in J. Heterocyclic Chem., 12, 829 (1975). Compound m-6: 6.0 g Tin powder: 11.6 g Dioxane: 200 ml Next, the reaction solution was heated to reflux with stirring under a nitrogen stream, and 42 ml of concentrated hydrochloric acid was added dropwise thereto, and the reaction was carried out for about 6 hours. The reaction solution was returned to room temperature, the precipitate was suction filtered, washed with ethanol, and dried under reduced pressure at 90 °C to obtain 6.2 g of the hydrochloride (tetrahydrochloride) of Compound m-7.

[0145] (2) Synthesis of Compound m-8 The following reagents and solvents were charged into a 200 ml eggplant flask. Tetrahydrochloride of Compound m-7: 3.0 g Oxalyl dibromide: 3.3 ml Acetic acid: 60 ml Next, the reaction solution was heated to reflux with stirring. After 3 hours, the reaction solution was returned to room temperature, the precipitate was suction filtered, washed with methanol, and dried under reduced pressure to obtain 3.7 g of Compound m-8.

[0146] (3) Synthesis of Compound m-10 The following reagents and solvents were charged into a 200 ml eggplant flask. Compound m-8: 2.0 g (3.63 mmol) Compound m-9: 1.5 g (7.64 mmol) Sodium tert-butoxide: 0.52 g (5.46 mmol) Pd(dba) 2 : 104 mg (0.18 mmol) Tri-tert-butylphosphine: 110 mg (0.55 mmol) o-Xylene: 60 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 2.0 g (yield: 70%) of yellow solid m-10.

[0147] (4) Synthesis of Compound D-2 A 200 ml eggplant flask was charged with the following reagents and solvents. Compound m-10: 1.0 g (1.28 mmol) Sodium tert-butoxide: 0.18 g (1.93 mmol) Pd 2 (dba) 3 : 59 mg (0.10 mmol) Tri-tert-butylphosphine: 39 mg (1.92 mmol) o-Xylene: 30 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 0.64 g (yield: 80%) of yellow solid D-2.

[0148] Mass spectrometry was performed on the obtained yellow solid D-2 using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker). Mass spectrometry confirmed that the target compound D-2 was successfully synthesized.

[0149] [MALDI-TOF-MS] Measured value: m / z = 620 Calculated value: C 40 H 28 N 8 = 620 <Examples 13 to 19 (Synthesis of Exemplary Compounds)> As shown in Table 3, for the exemplary compounds shown in Examples 13 to 19, the exemplary compounds were synthesized in the same manner as in Example 12, except that starting material m-9 shown in Example 12 was changed to starting material 2. Also, the measured values (m / z) of the mass spectrometry results measured in the same manner as in Example 12 are summarized in Table 3.

Table 3

[0150] <Example 20 (Synthesis of Exemplary Compound E-2)> According to the following scheme, exemplary compound D-2 was synthesized. The following scheme is the reaction scheme in Reaction Scheme 3 described above, where the substituent Gr is the substituent represented by the above general formula [3], and X 1 and X 2 are both methyl groups.

Chemical Formula

[0151] (1) Synthesis of Compound m-12 A 200 ml eggplant flask was charged with the following reagents and solvents. Compound m-11: 3.0 g Oxalyl dibromide: 8.9 ml Acetic acid: 90 ml Next, the reaction solution was heated under reflux and stirred. After 3 hours, the reaction solution was returned to room temperature, the precipitate was suction filtered, washed with methanol, and then dried under reduced pressure to obtain 11.4 g (yield: 90%) of compound m-12.

[0152] (2) Synthesis of Compound m-14 A 200 ml eggplant flask was charged with the following reagents and solvents. Compound m-12: 2.0 g (2.83 mmol) Compound m-13: 1.7 g (6.76 mmol) Sodium tert-butoxide: 0.40 g (4.24 mmol) Pd(dba)2 : 46 mg (0.08 mmol) Tri-tert-butylphosphine: 50 mg (0.25 mmol) o-Xylene: 60 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 carried out, and the solution was concentrated to dryness. The obtained solid was purified by silica gel column chromatography (toluene:ethyl acetate mixture) to obtain 2.4 g of yellow solid m-14 (yield: 80%).

[0153] (3) Synthesis of Compound E-2 A 200 ml eggplant flask was charged with the following reagents and solvents. Compound m-14: 1.0 g (0.95 mmol) Sodium tert-butoxide: 0.13 g (1.43 mmol) Pd 2 (dba) 3 : 30 mg (0.48 mmol) Tri-tert-butylphosphine: 29 mg (1.43 mmol) o-Xylene: 30 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 carried out, and the solution was concentrated to dryness. The obtained solid was purified by silica gel column chromatography (toluene:ethyl acetate mixture) to obtain 0.62 g of yellow solid E-2 (yield: 80%).

[0154] Mass spectrometry was performed on the obtained yellow solid E-2 using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker). Mass spectrometry confirmed that the target compound E-2 was successfully synthesized.

[0155] [MALDI-TOF-MS] Measured value: m / z = 814 Calculated value: C 54 H 39 N 9 = 814 <Examples 21 to 23 (Synthesis of Exemplary Compounds)> As shown in Table 4, for the exemplary compounds shown in Examples 21 to 23, the exemplary compounds were synthesized in the same manner as in Example 20, except that the raw material m-13 in Example 20 was changed to raw material 3. Further, the measured values (m / z) of the mass spectrometry results measured in the same manner as in Example 20 are summarized in Table 4.

Table 4

[0156] <Example 24> 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.

[0157] 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 deposit the organic compound layer and the electrode layer (cathode) shown in Table 5 on the ITO substrate. At this time, the electrode area of the electrode (cathode) facing the ITO electrode was 3 mm 2 so as to be.

Table 5

[0158] For the obtained device, the characteristics of the device were measured and evaluated. As an initial characteristic related to light emission, green light emission with a maximum external quantum efficiency (E.Q.E.) of 5.9% was obtained. Specifically, the current-voltage characteristics were measured with a microammeter 4140B manufactured by Hewlett-Packard Company, and the emission luminance was measured with a BM7 manufactured by Topcon Corporation. Further, a continuous drive test was performed at a current density of 50 mA / cm 2 and the time (LT95) when the luminance degradation rate reached 5% was measured, and it was 120 hours.

[0159] <Examples 25 to 29> In Example 24, an organic light-emitting device was fabricated in the same manner as in Example 24, except that the materials forming each layer were appropriately changed to the compounds shown in Table 6. For the layers not described in Table 6, the same configuration as in Example 24 was adopted. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 24. The measurement results are shown in Table 6 together with the measurement results of Example 24.

Table 6

[0160] <Example 30> In this example, a bottom-emission type organic EL device having a 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.

[0161] First, ITO was deposited on a glass substrate and subjected to a desired patterning process to form an ITO electrode (anode). 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 the electrode layer (cathode) shown in Table 7 on the ITO substrate. At this time, the electrode area of the electrode (cathode) facing the ITO electrode was set to 3 mm 2 to be.

Table 7

[0162] For the obtained device, the characteristics of the device were measured and evaluated. As an initial characteristic related to light emission, green light emission with a maximum external quantum efficiency (E.Q.E.) of 6.8% was obtained. Specifically, the current-voltage characteristics were measured with a microammeter 4140B manufactured by Hewlett-Packard, and the light emission luminance was measured with a BM7 manufactured by Topcon. Furthermore, at a current density of 50 mA / cm 2A continuous drive test was conducted, and when the luminance degradation rate reached 5%, the time (LT95) was measured and found to be 153 hours.

[0163] <Examples 31 to 45, Comparative Examples 1 to 2> In Example 30, an organic light-emitting device was fabricated in the same manner as in Example 30, except that the compounds shown in Table 8 were appropriately changed. For the layers not described in Table 8, the same configuration as in Example 30 was used. The characteristics of the obtained devices were measured and evaluated in the same manner as in Example 30. The measurement results are shown in Table 8 together with the measurement results of Example 30. The compounds (comparative compounds) used as assist materials in Comparative Examples 1 to 2 are shown below. [Chemical formula] [Table 8]

[0164] As shown in Table 8, the maximum external quantum efficiency (E.Q.E.) of the organic light-emitting devices of Comparative Example 1 and Comparative Example 2 was as low as 4.0 or less. That is, the organic light-emitting devices of Comparative Example 1 and Comparative Example 2 had low luminous efficiency. The comparative compound F-1 used as an assist material in Comparative Example 1 is the compound a-1 shown in Table 1. As described above, the compound a-1 has a structure having an amino group as a substituent on a hexaazatriphenylene skeleton which is a basic skeleton, but since the substituent does not have a structure with a large steric hindrance, the substituent and the basic skeleton are arranged on the same plane to form a highly planar structure. Therefore, the overlap of the HOMO electron orbital distribution and the LUMO electron orbital s distribution is large, and the energy difference between S 1 and T 1 is large. As a result, reverse intersystem crossing is less likely to occur, and delayed fluorescence-type emission is less likely to occur, so the luminous efficiency of the organic light-emitting device of Comparative Example 1 is low. The same applies to the comparative compound F-2 used as an assist material in Comparative Example 2. Since the substituent of the comparative compound F-2 does not have a structure with a large steric hindrance, it has a highly planar structure in which the substituent and the basic skeleton are arranged on the same plane. Therefore, the comparative compound F-2 also has S 1and T 1 Since the difference with T is large and delayed fluorescence emission hardly occurs, the light emission efficiency of the organic light-emitting device of Comparative Example 2 is low.

[0165] In addition, the 5% degradation life (LT95) of the organic light-emitting devices of Comparative Example 1 and Comparative Example 2 was 50 hours or less, indicating low durability. This is presumably because Comparative Compound F-1 and Comparative Compound F-2 have high planarity, so molecular aggregation easily occurs, the film property is poor, and they are compounds that easily crystallize.

[0166] On the other hand, the organic light-emitting devices of Examples 30 to 45 showed good results in both light emission efficiency and durability. All of the compounds of the present invention used as assist materials in Examples 30 to 45 have substituents with relatively large steric hindrance with respect to the hexaazatriphenylene skeleton which is the basic skeleton. Therefore, the substituent takes a non-planar structure in which it is spatially twisted with respect to the basic skeleton, and the overlap between the electron orbital distribution of HOMO and the electron orbital distribution of LUMO is small, and S 1 and T 1 The energy difference with T is small. As a result, reverse intersystem crossing easily occurs, delayed fluorescence emission easily occurs, and it is considered that high-efficiency light emission is shown. In addition, by having the above structure, it is considered that the light-emitting layer becomes a film with high amorphousness and shows good durability.

[0167] Example 36 and Comparative Example 1 have the same configuration in all aspects other than the assist material. In Example 36, Compound C-36, which is one of the compounds of the present invention, is used as the assist material, while in Comparative Example 1, Comparative Compound F-1 is used as the assist material. As described above, since the amino group, which is a substituent for the basic skeleton of Compound C-36, has relatively large steric hindrance, the substituent takes a configuration in which it is sterically twisted with respect to the basic skeleton. Therefore, S 1 and T 1 The energy difference with T is small, and it is considered that delayed fluorescence emission easily occurs. As a result, in Example 36, an organic light-emitting device excellent in both light emission efficiency and durability was obtained as compared with Comparative Example 1 using Comparative Compound F-1 in which delayed fluorescence emission hardly occurs.

[0168] Example 45 and Comparative Example 2 have the same configuration except for the assist material. In Example 45, Compound E-1, which is one of the compounds of the present invention, is used as the assist material, while in Comparative Example 2, Comparative Compound F-2 is used as the assist material. As described above, since the amino group, which is a substituent for the basic skeleton, of Compound E-1 has a relatively large steric hindrance, the substituent is arranged in a sterically twisted configuration with respect to the basic skeleton. Therefore, S 1 and T 1 are considered to have a small energy difference and be prone to delayed fluorescence emission. As a result, in Example 45, an organic light-emitting device having excellent luminous efficiency and durability was obtained as compared with Comparative Example 2 using Comparative Compound F-2, in which delayed fluorescence emission is less likely to occur.

Explanation of Reference Numerals

[0169] 1 Organic light-emitting device 11 Substrate 21 Anode 22 Organic compound layer 23 Cathode

Claims

1. An organic compound characterized by being represented by the following general formula [1]. 【Chemical 1】 (In general formula [1], R １ ~R ６ are each independently selected from the group consisting of a hydrogen atom, a hydrocarbon group, and a substituent represented by the following general formulas [2] to [18], and at least one of R １ ~R ６ is a substituent represented by the following general formulas [2] to [18]. However, one of R1 or R2 is a substituent represented by the following general formulas [2] to [18], and one of R3 or R4 is a substituent represented by the following general formulas [2] to [18]. R １ and R ２ are such that at least one of them is a hydrogen atom or a hydrocarbon group. R ３ and R ４ are such that at least one of them is a hydrogen atom or a hydrocarbon group. R ５ and R ６ are such that at least one of them is a hydrogen atom.) [Chemical 2] (In general formulas [2] to [18], X １ and X ２ are each independently selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.)

2. In the general formula [1], one of R1 or R2 is a substituent represented by the general formulas [2] to [18], one of R3 or R4 is a substituent represented by the general formulas [2] to [18], and one of R5 or R6 is a substituent represented by the general formulas [2] to [18]. The organic compound according to Claim 1, characterized in that.

3. In the general formula [1], R １ and R ３ are each independently selected from the substituents represented by the general formulas [2] to [18], and R ２ , and R ４ to R ６ are each independently a hydrogen atom or a hydrocarbon group, The organic compound according to claim 1.

4. In the general formula [1], R １ , R ３ , and R ５ are each independently selected from the substituents represented by the general formulas [2] to [18], R ２ and R ４ are each independently a hydrogen atom or a hydrocarbon group, and R6 is a hydrogen atom. The organic compound according to claim 1, characterized in that

5. In the general formula [2], X １ and X ２ are each independently selected from a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and a substituted or unsubstituted heterocyclic group having 3 to 9 carbon atoms. The organic compound according to any one of claims 1 to 4, characterized in that.

6. In the general formula [1], R １ ~R ６ is each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and a substituent represented by the following general formulas [2] to [18]. The organic compound according to any one of claims 1 to 5, characterized in that.

7. In the general formula [1], R １ ~R ６ is each independently selected from the group consisting of a hydrogen atom and substituents represented by the following general formulas [2] to [18], the organic compound according to any one of claims 1 to 5.

8. In the general formula [2], X １ and X ２ are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and the organic compound according to any one of claims 1 to 7 is characterized thereby.

9. In the general formula [2], X １ and X ２ are each independently a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and the organic compound according to any one of claims 1 to 7.

10. In the general formula [2], X １ and X ２ are each independently a substituted or unsubstituted heterocyclic group having 3 to 9 carbon atoms, and the organic compound according to any one of claims 1 to 7, characterized in that.

11. An anode and a cathode, In an organic light-emitting device having at least one organic compound layer disposed between the anode and the cathode, The organic compound layer contains the organic compound according to any one of Claims 1 to 10. The organic light-emitting device, characterized in that.

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

13. The light-emitting layer further contains a host material. The organic light-emitting device according to Claim 11 or 12, characterized in that.

14. The host material is a hydrocarbon compound. The organic light-emitting device according to Claim 13, characterized in that.

15. The light-emitting layer further contains a light-emitting material. The organic light-emitting device according to Claim 13 or 14, characterized in that.

16. The light-emitting material is a hydrocarbon compound. The organic light-emitting device according to Claim 15, characterized in that.

17. The light-emitting layer emits green light or red light. The organic light-emitting device according to any one of Claims 12 to 16, characterized in that.

18. A display device having a plurality of pixels, wherein at least one of the plurality of pixels has an organic light-emitting device according to any one of Claims 11 to 17 and a transistor connected to the organic light-emitting device.

19. A display device having a plurality of pixels, wherein the plurality of pixels have an organic light-emitting device according to any one of Claims 11 to 17, a transistor connected to the organic light-emitting device, and a color filter.

20. 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. The display unit has the organic light-emitting element according to any one of claims 11 to 17, and the photoelectric conversion device is characterized by this.

21. An electronic device, comprising: a display unit having the organic light-emitting element according to any one of claims 11 to 17; a housing provided with the display unit; and a communication unit provided in the housing and communicating with the outside.

22. An illumination device, comprising: a light source having the organic light-emitting element according to any one of claims 11 to 17; and a light diffusing unit or an optical filter that transmits light emitted by the light source.

23. A moving body, comprising: a lighting fixture having the organic light-emitting element according to any one of claims 11 to 17; and a body provided with the lighting fixture.

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