Organic compound and organic light-emitting device

Abstract

To provide a compound for a blue light emitting material that has high emission efficiency by reduced concentration quenching, has excellent electron acceptability by large reduction potential, and has good color purity.SOLUTION: The present disclosure provides, for example, the following compound (reaction product C14).SELECTED DRAWING: None

Description

[Technical field]

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

[0002] An organic light-emitting element (also called an organic electroluminescent element or an organic EL element) is an electronic element having a pair of electrodes and an organic compound layer disposed between the electrodes. By injecting electrons and holes from the 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. Recent progress in organic light-emitting devices has been remarkable, including low driving voltage, diverse emission wavelengths, high-speed response, and the possibility of making light-emitting devices thinner and lighter. In addition, the sRGB and AdobeRGB standards are used to represent the color reproduction range of displays, and materials that can reproduce these have been in demand, but recently BT-2020 has been cited as a standard that will further expand the color reproduction range. Incidentally, the creation of light-emitting organic compounds has been actively carried out up to now. This is because the creation of compounds with excellent light-emitting properties is important in providing high-performance organic light-emitting devices. Patent Document 1 describes the following compounds 1-a, 1-A, and 1-B.

[0003] [ka]

[0004] [ka] [Prior art documents] [Patent documents]

[0005] [Patent Document 1] JP 2010-143879 A Summary of the Invention [Problem to be solved by the invention]

[0006] Compound 1-a described in Patent Document 1 is a blue light-emitting material, but further improvement in luminous efficiency in a thin film state is desired. Further improvement in electron-accepting property is also desired. Further improvement in luminous efficiency or durability of organic light-emitting devices using these compounds is desired. In addition, although compounds 1-A and 1-B described in Patent Document 1 are blue light-emitting materials, further improvement in electron acceptance is desired. In addition, considering the blue color reproduction range corresponding to the sRGB, AdobeRGB, and BT2020 standards, further improvement in color purity of blue light emission is desired. Further improvement in color purity or durability is desired for organic light-emitting elements using these compounds. The present invention has been made in view of the above problems, and an object of the present invention is to provide a blue light-emitting material which has high luminous efficiency due to reduced concentration quenching, excellent electron accepting property due to a large reduction potential, and good color purity. Another object of the present invention is to provide a blue light-emitting material having a high reduction potential, excellent electron acceptance, and good color purity.Another object of the present invention is to provide an organic light-emitting device having excellent color purity and driving durability.Another object of the present invention is to provide an organic light-emitting device having excellent luminous efficiency and driving durability. [Means for solving the problem]

[0007] One embodiment of the present invention provides an organic compound represented by the following general formula [1]:

[0008] [ka] In the general formula [1], R1 to R 18are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a silyl group, and a group represented by any one of the following general formulae [2] to [3],

[0102] to

[0104] , provided that at least one of them is a group represented by any one of the following general formulae [2] to [3],

[0102] to

[0104] . The group represented by any one of the following general formulas [2] and [3] is R 19 From R 32 A group bonded at any one of the positions The group shown in any one of the following general formulae

[0102] to

[0104] is a group bonded at the position shown by *. do.

[0009] [ka] In the general formulas [2] and [3], R 19 From R 32 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, and a silyl group. 19 From R 32 may form a ring with the adjacent group. X is independently selected from an oxygen atom, a sulfur atom, a selenium atom, and a tellurium atom.

[0010] [ka] (In the general formula

[0102] , X1 to X3 each represent a hydrogen atom, a carbon atom having a substituent Y, or a nitrogen atom constituting a ring, and at least one of them is a nitrogen atom. The substituent Y is a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, and a silyl group. When there are a plurality of carbon atoms having the substituent Y, the substituents Y may be the same or different. R105 ~R 106 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

[0011] [ka] (In the general formula

[0103] , X4 to X7 each represent a hydrogen atom or a carbon atom having a substituent Y, or a nitrogen atom constituting a ring, and at least one of them is a nitrogen atom. The substituent Y is a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, and a silyl group. When there are a plurality of carbon atoms having the substituent Y, the substituents Y may be the same or different. R 107 ~R 109 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

[0012] [ka] (In the general formula

[0104] , X8 to X 12 represents a hydrogen atom, a carbon atom having a substituent Y, or a nitrogen atom which constitutes a ring, and at least one of them is a nitrogen atom. The substituent Y is a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, and a silyl group. When there are a plurality of carbon atoms having the substituent Y, the substituents Y may be the same or different. R 110 ~R 111 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

[0013] Moreover, one embodiment of the present invention provides an organic compound represented by the following general formula:

[0014] [ka] (In general formula

[0101] , a group having an azine skeleton represented by the following general formulae

[0102] to

[0104] is bonded at the position indicated by * to at least one of the positions indicated by *1 to *6. When a plurality of groups having an azine skeleton represented by the general formulae

[0102] to

[0104] are bonded, the groups having an azine skeleton represented by the general formulae

[0102] to

[0104] may be the same or different. R 101 ~R 104 are each independently selected from a hydrogen atom, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aryloxy group.

[0015] [ka] (In the general formula

[0102] , X1 to X3 each represent a hydrogen atom, a carbon atom having a substituent Y, or a nitrogen atom constituting a ring, and at least one of them is a nitrogen atom. The substituent Y is a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, and a silyl group. When there are a plurality of carbon atoms having the substituent Y, the substituents Y may be the same or different. R 105 ~R 106 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

[0016] [ka] (In the general formula

[0103] , X4 to X7 each represent a hydrogen atom or a carbon atom having a substituent Y, or a nitrogen atom constituting a ring, and at least one of them is a nitrogen atom. The substituent Y is a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, and a silyl group. When there are a plurality of carbon atoms having the substituent Y, the substituents Y may be the same or different. R 107 ~R 109 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

[0017] [ka] (In the general formula

[0104] , X8 to X 12 represents a hydrogen atom, a carbon atom having a substituent Y, or a nitrogen atom which constitutes a ring, and at least one of them is a nitrogen atom. The substituent Y is a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, and a silyl group. When there are a plurality of carbon atoms having the substituent Y, the substituents Y may be the same or different. R 110 ~R 111 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. Effect of the Invention

[0018] The organic compound represented by the general formula [1] according to the present invention has high luminous efficiency due to reduced concentration quenching, and has excellent electron accepting property due to a large reduction potential, and is capable of emitting blue light with good color purity.

[0019] The organic compound represented by the general formula

[0101] according to the present invention is a blue light-emitting material having a large reduction potential, excellent electron acceptance properties, and good color purity. [Brief description of the drawings]

[0020] [Figure 1] 1 is a schematic cross-sectional view of an example of a display device using an organic light-emitting element according to one embodiment of the present invention. [Diagram 2] FIG. 1 is a schematic diagram illustrating an example of a display device according to an embodiment of the present invention. [Diagram 3] 1A is a schematic diagram illustrating an example of an imaging device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram illustrating an example of an electronic device according to an embodiment of the present invention. [Figure 4] 1A is a schematic diagram illustrating an example of a display device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram illustrating an example of a foldable display device. [Diagram 5] 1A is a schematic diagram showing an example of an illumination device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram showing an example of an automobile having a vehicle lamp according to an embodiment of the present invention. [Figure 6] FIG. 1 is a visualization of the HOMO and LUMO electron orbital distributions of the diacenaphtho[1,2-b:1',2'-k]chrysene skeleton. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0021] <Organic compound represented by general formula [1]> First, the organic compound according to the present embodiment will be described. The novel organic compound according to the present embodiment is an organic compound represented by the following general formula [1].

[0022] [ka]

[0023] In the general formula [1], R1 to R 18are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a silyl group, and a group represented by any one of the following general formulae [2] to [3],

[0102] to

[0104] , provided that at least one of them is a group represented by any one of the following general formulae [2] to [3],

[0102] to

[0104] .

[0024] The group represented by any one of the following general formulas [2] and [3] is R 19 From R 32 is a group bonded at any one of the positions.

[0025] [ka]

[0026] In the general formulas [2] and [3], R 19 From R 32 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, and a silyl group. 19 From R 32 may form a ring with the adjacent group.

[0027] X is independently selected from an oxygen atom, a sulfur atom, a selenium atom, and a tellurium atom.

[0028] [ka]

[0029] In the general formula

[0102] , X1 to X3 each represent a hydrogen atom, a carbon atom having a substituent Y, or a nitrogen atom which constitutes a ring, and at least one of them is a nitrogen atom. The substituent Y is a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, and a silyl group. When there are a plurality of carbon atoms having the substituent Y, the substituents Y may be the same or different. R 105 ~R 106 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

[0030] [ka]

[0031] In the general formula

[0103] , X4 to X7 each represent a hydrogen atom or a carbon atom having a substituent Y, or a nitrogen atom which constitutes a ring, and at least one of them is a nitrogen atom. The substituent Y is a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, and a silyl group. When there are a plurality of carbon atoms having the substituent Y, the substituents Y may be the same or different. R 107 ~R 109 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

[0032] [ka]

[0033] In the general formula

[0104] , X8 to X 12 represents a hydrogen atom, a carbon atom having a substituent Y, or a nitrogen atom which constitutes a ring, and at least one of them is a nitrogen atom. The substituent Y is a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, and a silyl group. When there are a plurality of carbon atoms having the substituent Y, the substituents Y may be the same or different. R 110 ~R 111 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

[0034] The group represented by any one of the general formulae [2] to [3] and

[0102] to

[0104] is preferably a group represented by any one of the general formulae [2] to [3]. The number of groups represented by any one of the general formulae [2] to [3] and

[0102] to

[0104] is not particularly limited, but is preferably 1 to 4, more preferably 1 to 2. In addition, R3, R4, R7, R8, R9, and R 12 , R 13 , R 16 , R 17 , R 18 At least one of R7, R8, R9, R 16 , R 17 , R 18 At least one of the groups represented by the general formulas [2] to [3] and

[0102] to

[0104] is preferably a group represented by any one of the general formulas [2] to [3]. 22 , R 23 , R 29 It is preferable that the group represented by any one of the general formulae [2] and [3] is a dibenzofuranyl group or a dibenzothiophenyl group.

[0035] Also, R1 to R 18 are preferably independently selected from a hydrogen atom and a group represented by any one of the general formulae [2] to [3],

[0102] to

[0104] . 10 , R 15is a hydrogen atom, R3, R4, R 12 , R 13 are hydrogen atoms, R7, R9, R 16 and R 18 is preferably a hydrogen atom.

[0036] In this embodiment, R1 to R 32 Examples of the halogen atom represented by the formula (I) include, but are not limited to, fluorine, chlorine, bromine, and iodine.

[0037] R1 to R 32 Examples of the alkyl group represented by the formula (1) include, but are not limited to, a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, a tertiary butyl group, a secondary butyl group, an octyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, etc. Among these, an alkyl group having 1 to 10 carbon atoms is preferred.

[0038] R1 to R 32 Examples of the alkoxy group represented by the formula (1) include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, a 2-ethyl-octyloxy group, a benzyloxy group, etc. Among these, an alkoxy group having 1 to 6 carbon atoms is preferred.

[0039] R1 to R 32Examples of the amino group represented by the formula (I) include, but are not limited to, an N-methylamino group, an N-ethylamino group, an N,N-dimethylamino group, an N,N-diethylamino group, an N-methyl-N-ethylamino group, an N-benzylamino group, an N-methyl-N-benzylamino group, an N,N-dibenzylamino group, an anilino group, an N,N-diphenylamino group, an N,N-dinaphthylamino group, an N,N-difluorenylamino group, an N-phenyl-N-tolylamino group, an N,N-ditolylamino group, an N-methyl-N-phenylamino group, an N,N-dianisolylamino group, an N-mesityl-N-phenylamino group, an N,N-dimesitylamino group, an N-phenyl-N-(4-tert-butylphenyl)amino group, an N-phenyl-N-(4-trifluoromethylphenyl)amino group, and an N-piperidyl group.

[0040] R1 to R 32 Examples of the aryl group represented by the formula (1) include, but are not limited to, a phenyl group, a naphthyl group, an indenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a phenanthryl group, a triphenylenyl group, etc. Among these, an aryl group having 6 to 18 carbon atoms is preferred.

[0041] R1 to R 32 Examples of the aryloxy group represented by the formula (I) include, but are not limited to, a phenoxy group, a thienyloxy group, etc. Among these, an aryloxy group having 6 to 18 carbon atoms is preferred.

[0042] R1 to R 32 Examples of the silyl group represented by the formula (I) include, but are not limited to, a trimethylsilyl group and a triphenylsilyl group.

[0043] Examples of the substituent that the above alkyl group, alkoxy group, amino group, aryl group, and aryloxy group may further have include alkyl groups such as a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, and a tertiary butyl group; aralkyl groups such as a benzyl group; aryl groups such as a phenyl group and a biphenyl group; amino groups such as a dimethylamino group, a diethylamino group, a dibenzylamino group, a diphenylamino group, and a ditolylamino group; alkoxy groups such as a methoxy group, an ethoxy group, and a propoxy group; aryloxy groups such as a phenoxy group; halogen atoms such as fluorine, chlorine, bromine, and iodine; a thienyl group; and a thiol group, but are not limited to these.

[0044] Examples of the group represented by the general formula

[0102] include groups represented by the following general formulae

[0105] to

[0109] .

[0045] [ka]

[0046] In the general formulae

[0105] to

[0109] , R 112 ~R 127 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

[0047] Examples of the group represented by the general formula

[0103] or

[0104] include groups represented by the following general formulae

[0110] to

[0118] .

[0048] [ka]

[0049] In the general formulae

[0110] to

[0118] , R 128 ~R 181are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

[0050] Examples of the group represented by the general formula

[0103] or

[0104] include groups represented by the following general formulae

[0119] to

[0124] .

[0051] [ka]

[0052] In the general formulae

[0119] to

[0124] , R 182 ~R 211 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

[0053] In addition, examples of the group represented by the general formula

[0103] or

[0104] include a group in which X6 and X7 are carbon atoms, or 12 is a carbon atom.

[0054] Y, R 105 ~R 211 Examples of the alkyl group represented by the formula (1) include, but are not limited to, a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, a tertiary butyl group, a secondary butyl group, an octyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, etc. Among these, an alkyl group having 1 to 10 carbon atoms is preferred.

[0055] Y, R 105 ~R 211 Examples of the aryl group represented by the formula (1) include, but are not limited to, a phenyl group, a naphthyl group, an indenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a phenanthryl group, a triphenylenyl group, etc. Among these, an aryl group having 6 to 18 carbon atoms is preferred.

[0056] Y, R 105 ~R 211 Examples of the heterocyclic group represented by the formula (1) include, but are not limited to, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a carbazolyl group, an acridinyl group, a phenanthrolyl group, etc. Among these, a heterocyclic group having 3 to 15 carbon atoms is preferred.

[0057] Examples of the aryloxy group represented by Y include, but are not limited to, a phenoxy group and a thienyloxy group.

[0058] Examples of the silyl group represented by Y include, but are not limited to, a trimethylsilyl group and a triphenylsilyl group.

[0059] Examples of the substituent that the above alkyl group, aryl group, heterocyclic group, and aryloxy group may further have include alkyl groups such as a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, and a tertiary butyl group; aralkyl groups such as a benzyl group; aryl groups such as a phenyl group and a biphenyl group; heterocyclic groups such as a pyridyl group and a pyrrolyl group; alkoxy groups such as a methoxy group, an ethoxy group, and a propoxy group; and aryloxy groups such as a phenoxy group, but are not limited to these.

[0060] Next, a method for synthesizing the organic compound according to the present embodiment will be described. The organic compound according to the present embodiment can be synthesized, for example, according to the reaction scheme shown below.

[0061] [ka]

[0062] Here, by appropriately changing G1 to G4, a compound represented by the general formula [1] can be obtained. Details of the synthesis method will be explained in the Examples.

[0063] Next, the organic compound according to this embodiment has the following characteristics, and therefore exhibits high-efficiency blue light emission with high color purity, has a large reduction potential (in the direction away from the vacuum level when expressed in terms of LUMO), and is a chemically stable compound. Furthermore, by using the organic compound according to this embodiment, it is possible to provide an organic light-emitting device with excellent color purity, luminous efficiency, and device durability.

[0064] (1) The basic skeleton has a benzochalcogenophene derivative group represented by any one of general formulas [2] and [3] (hereinafter, sometimes simply referred to as a "benzochalcogenophene derivative group") as an electron-withdrawing substituent, and thus has high electron-accepting properties and blue light emission with high color purity. (2) The inclusion of a benzochalcogenophene derivative group in the basic structure as a substituent for reducing concentration quenching improves the luminescence efficiency in a thin film state.

[0065] The basic skeleton in this embodiment is R1 to R2 of the compound represented by the general formula [1]. 18 is a skeleton in which all are replaced by hydrogen atoms.

[0066] The following describes the properties of the basic skeleton of the organic compound according to this embodiment, with reference to comparative compounds having a structure similar to that of the organic compound according to this embodiment. Specifically, the comparative compounds are comparative compound 1-a described in Patent Document 1 and comparative compound 1-b similar to the organic compound according to this embodiment.

[0067] [ka]

[0068] Here, one of the organic compounds according to the present embodiment is a compound represented by the formula [1], in which R1 to R7 and R9 to R 16 , R 18is a hydrogen atom, R and R 17 is an exemplary compound A1 in which the substituent is a dibenzofuranyl group.

[0069] (1) The basic structure has a benzochalcogenophene derivative group as an electron-withdrawing substituent, which results in high electron-accepting properties and blue emission with high color purity. In inventing the organic compound represented by the general formula [1], the present inventors focused on the basic skeleton itself.

[0070] First, in order to emit blue light with good color purity, the basic skeleton itself must be in a blue region with high color purity. In this embodiment, the desired emission wavelength region is a blue region with high color purity, specifically, the maximum emission wavelength in a dilute solution is within a band of 430 nm to 450 nm. The basic skeleton of this embodiment is a skeleton suitable for emitting the desired blue light.

[0071] On the other hand, the basic skeleton of this embodiment exhibits blue light emission with good color purity, but the band gap of the compound is large and the electron acceptance is low. It is necessary to increase the stability of the organic light-emitting material against electric charges, and for this purpose, it is required to increase the electron acceptance. In an organic light-emitting device, an organic compound sandwiched between electrodes repeats oxidation and reduction between molecules, and the excited state and ground state of the organic compound are repeated by carrier recombination, and light is emitted. Therefore, a compound that is unstable against the transfer of electric charges undergoes a chemical change in the oxidation-reduction process or the excited state, and changes into a different compound. As a result, the original element characteristics are impaired, the luminance of the organic light-emitting device is reduced, and the element durability during continuous operation is deteriorated. In order to reduce such deterioration, stability against electric charges is required, and high electron acceptance is necessary.

[0072] Therefore, the inventors focused on increasing the reduction potential as one of the design guidelines for materials with high electron-accepting properties, and discovered the compound of general formula [1]. Specifically, by substituting a benzochalcogenophene derivative group as an electron-withdrawing substituent on the basic skeleton, the electron-accepting property can be improved and the stability against electric charge can be further increased.

[0073] The reduction potentials and maximum emission wavelengths in a dilute toluene solution are compared by CV measurement using the exemplary compound A1 according to this embodiment and the comparative compounds 1-a and 1-b in Table 1. The comparative compound 1-b is listed as a comparative compound similar to the exemplary compound A1 and does not have a chalcogen atom in order to show the effect of the chalcogen atom, which is a feature of this embodiment.

[0074] The emission wavelength was measured by photoluminescence measurement of a diluted toluene solution at room temperature with an excitation wavelength of 350 nm using a Hitachi F-4500. The reduction potential was measured by CV (cyclic voltammetry). The CV measurement was performed using a 0.1 M tetrabutylammonium perchlorate solution in DMF (reduction potential measurement), and the reference electrode was Ag / Ag + The counter electrode was Pt and the working electrode was glassy carbon. The voltage sweep rate was 1.0 V / s. The measurement device used was an electrochemical analyzer, Model 660C, manufactured by ALS.

[0075] [Table 1]

[0076] From Table 1, it can be seen that the compound of this embodiment has a benzochalcogenophene derivative group as an electron-withdrawing substituent, and thus has a higher reduction potential than the comparative compounds 1-a and 1-b. In other words, it can be seen that the compound of this embodiment has improved electron-accepting properties. In addition, the emission wavelength of the comparative compound 1-a is 448 nm, whereas the exemplary compound A1 of this embodiment emits blue light with higher color purity. In this way, it has been found that the unique effect of the benzochalcogenophene derivative group is that it can emit blue light with high color purity and have a high reduction potential.

[0077] (2) The inclusion of a benzochalcogenophene derivative group in the basic structure as a substituent for reducing concentration quenching improves the luminescence efficiency in a thin film state. Although the basic skeleton of this embodiment emits blue light with good color purity, its high planarity causes a decrease in luminous efficiency in a thin film due to concentration quenching. If the efficiency decreases in a thin film, the luminous efficiency also decreases when used in an organic light-emitting device. Therefore, it is necessary to reduce concentration quenching by introducing a substituent, but the effect varies depending on the type of the substituent. Therefore, in this embodiment, as one of the design guidelines for reducing concentration quenching, the compound of general formula [1] was found by focusing on the effect of reducing intermolecular interactions due to a bulky fused ring structure among the substituents.

[0078] Specifically, the luminous efficiency in a thin film state can be improved by substituting a benzochalcogenophene derivative group as a bulky fused ring structure substituent relative to the basic skeleton. Table 2 compares the luminous quantum yields in a dilute toluene solution and in a vapor deposition film (single film) using the exemplary compound A1 according to this embodiment and the comparative compound 1-a. The luminous quantum yields are shown as a ratio when the luminous quantum yield of the comparative compound 1-a is set to 1.0.

[0079] The evaporated film was formed on a glass substrate by vacuum deposition using resistance heating in a vacuum chamber. The emission quantum yield was measured by placing the evaporated glass substrate in the integrating sphere of a Hamamatsu Photonics C9920-02 and measuring photoluminescence at room temperature with an excitation wavelength of 350 nm.

[0080] From Table 2, it can be seen that the luminescence quantum yield of the compound A1 of this embodiment is improved compared to the comparative compound 1-a due to the substituent having a bulky fused ring structure. In other words, it can be seen that the compound of this embodiment has an improved effect of reducing concentration quenching.

[0081] [Table 2]

[0082] Furthermore, in the organic compound represented by the general formula [1], R7, R8, R9, R 16 , R 17 , R 18It is preferable that at least one of the groups has a chalcogenophene derivative group.

[0083] The basic skeleton plane of this embodiment has a large ratio of the long axis to the short axis. Therefore, if the substituent is not substituted near the center of gravity, the distance between the basic skeleton planes becomes short in the thin film state, and the intermolecular interaction becomes large. This causes concentration quenching and a decrease in sublimation. Therefore, it is preferable that the substituent is substituted near the center of the molecule. In particular, the chalcogenophene derivative group has a high effect, as explained above.

[0084] In addition, the organic compound of this embodiment has a high glass transition temperature of 120° C. or more. This is because it has a benzochalcogenophene derivative group that is a condensed ring structure. When used in an organic light-emitting device, high crystallinity and a glass transition temperature lower than 120° C. induce crystallization during the process of device fabrication or during device operation, leading to a decrease in efficiency and a decrease in durability. Therefore, low crystallinity and a high glass transition temperature are necessary performances for realizing an excellent organic light-emitting device.

[0085] In the general formula [1], the group represented by any one of the general formulas [2] and [3] is R 22 , R 23 , R 29 This is because the group represented by any one of the general formulas [2] and [3] is a group represented by R 22 , R 23 , R 29 This is because, among the organic compounds according to this embodiment, an organic compound bonded at any one of the positions above exhibits blue light emission with higher color purity and a larger reduction potential.

[0086] Table 3 shows the maximum emission wavelength in a dilute toluene solution and the reduction potential by CV measurement for the exemplary compounds A1, B1, and B9 according to this embodiment. 22 , R 23 , R 29It can be seen that Exemplary Compound A1, in which the molecule is bonded at any one of the positions, has the shortest wavelength and the largest reduction potential.

[0087] [Table 3]

[0088] As described above, the organic compound according to the present embodiment is a compound having the above properties (1) and (2), and therefore exhibits high efficiency blue light emission with high color purity, and is a compound with high reduction potential and chemical stability, compared with the comparative compound. Therefore, by using the organic compound according to the present embodiment, an organic light-emitting device excellent in color purity, luminous efficiency, and element durability can be obtained.

[0089] Specific examples of the organic compound according to this embodiment are shown below, but this embodiment is not limited to these.

[0090] [ka]

[0091] [ka]

[0092] [ka]

[0093] [ka]

[0094] [ka]

[0095] [ka]

[0096] [ka]

[0097] [ka]

[0098] [ka]

[0099] [ka]

[0100] [ka]

[0101] Among the above-mentioned exemplary compounds, the compounds belonging to group A are those in which, in the formula [1], the benzochalcogenophene derivative group substituting the basic skeleton is R 22 , R 23 , R 29 The compounds belonging to group A are bonded at any one of the positions. Among the compounds according to this embodiment, the compounds belonging to group A emit blue light with a shorter wavelength and have a larger reduction potential. That is, group A is a compound group that emits blue light with higher color purity and has higher electron acceptance. In short, the compounds belonging to group A can also be used as a host material for the emission layer, a transport layer, or an injection layer, but when used in the emission layer, the emission efficiency is lower than when used as a guest at a low concentration.

[0102] Among the above-mentioned exemplary compounds, the compounds belonging to group B are those in which, in the formula [1], the benzochalcogenophene derivative group substituting the basic skeleton is R 22 , R 23 , R 29Among the compounds according to this embodiment, the B group is a compound group capable of finely adjusting blue luminescence and reduction potential.

[0103] Among the above-mentioned exemplary compounds, the compounds belonging to group C are those in which the basic skeleton has three or more substituents in formula [1], or those in which the benzochalcogenophene derivative group has further substituents. The intermolecular interaction is reduced by increasing the number of substituents or by increasing the bulk of the substituents. Therefore, among the compounds according to this embodiment, group C is a compound group that can further reduce concentration quenching in a thin film state when used as a guest in the light-emitting layer.

[0104] Among the above exemplary compounds, those belonging to group D are represented by the formula

[0105] The compound has a group represented by the formula

[0109] or

[0110] introduced therein. The compound has both high electron accepting properties and blue light emission with high color purity.

[0105] On the other hand, among the above example compounds, those belonging to group E are compounds into which groups represented by formulae

[0110] to

[0118] have been introduced. Since the number of nitrogen atoms per introduced group is lower than that of group D, the electron accepting property is alleviated, but Tg is improved with an increase in molecular weight, and it is possible to combine high heat resistance with blue light emission with good color purity.

[0106] Among the above-mentioned exemplary compounds, those belonging to group F are compounds having groups represented by the formulae

[0119] to

[0124] introduced therein. They can have both high heat resistance and high electron accepting property.

[0107] The organic compound according to the present embodiment is a compound that exhibits high efficiency and is suitable for blue light emission and has high chemical stability. Therefore, by using the organic compound according to the present embodiment as a constituent material of an organic light-emitting device, an organic light-emitting device having good light-emitting characteristics and excellent durability can be obtained.

[0108] <Organic compound represented by the general formula

[0101] > First, the organic compound according to this embodiment will be described. The organic compound according to this embodiment is an organic compound represented by the following general formula:

[0109] [ka]

[0110] In the general formula

[0101] , a group having an azine skeleton represented by the following general formulas

[0102] to

[0104] (hereinafter, sometimes simply referred to as a "group having an azine skeleton") is bonded to at least one position, preferably two positions, among the positions indicated by *1 to *6. The group having an azine skeleton is bonded at the position indicated by *. When a plurality of groups having an azine skeleton are bonded, the groups having an azine skeleton may be the same or different. R 101 ~R 104 R is a group independently selected from a hydrogen atom, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aryloxy group. 101 ~R 104 is preferably a hydrogen atom. 101 ~R 104 is preferably a group that does not have a lone pair of electrons, such as an aryl group that does not have a lone pair of electrons, in order to reduce intermolecular stacking.

[0111] [ka]

[0112] In the general formula

[0102] , X1 to X3 each represent a hydrogen atom, a carbon atom having a substituent Y, or a nitrogen atom which constitutes a ring, and at least one of them is a nitrogen atom. The substituent Y is a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, and a silyl group. When there are a plurality of carbon atoms having the substituent Y, the substituents Y may be the same or different. R 105 ~R 106 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

[0113] [ka]

[0114] In the general formula

[0103] , X4 to X7 each represent a hydrogen atom or a carbon atom having a substituent Y, or a nitrogen atom which constitutes a ring, and at least one of them is a nitrogen atom. The substituent Y is a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, and a silyl group. When there are a plurality of carbon atoms having the substituent Y, the substituents Y may be the same or different. R 107 ~R 109 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

[0115] [ka]

[0116] In the general formula

[0104] , X8 to X 12 represents a hydrogen atom, a carbon atom having a substituent Y, or a nitrogen atom which constitutes a ring, and at least one of them is a nitrogen atom. The substituent Y is a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, and a silyl group. When there are a plurality of carbon atoms having the substituent Y, the substituents Y may be the same or different. R 110 ~R 111are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

[0117] The groups bonded to the positions indicated by *1 to *6 may be groups having an azine skeleton represented by the general formula

[0102] , or may be groups having an azine skeleton represented by the general formula

[0103] or

[0104] .

[0118] Examples of the group having an azine skeleton represented by the general formula

[0102] include groups represented by the following general formulae

[0105] to

[0109] .

[0119] [ka]

[0120] In the general formulae

[0105] to

[0109] , R 112 ~R 127 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

[0121] Examples of the group having an azine skeleton represented by the general formula

[0103] or

[0104] include groups represented by the following general formulae

[0110] to

[0118] .

[0122] [ka]

[0123] In the general formulae

[0110] to

[0118] , R 128 ~R 181 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

[0124] Examples of the group having an azine skeleton represented by the general formula

[0103] or

[0104] include groups represented by the following general formulae

[0119] to

[0124] .

[0125] [ka]

[0126] In the general formulae

[0119] to

[0124] , R 182 ~R 211 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

[0127] In addition, examples of the group having an azine skeleton represented by the general formula

[0103] or

[0104] include a group in which X6 and X7 are carbon atoms, or 12 is a carbon atom.

[0128] Y, R 105 ~R 211 Examples of the alkyl group represented by the formula (1) include, but are not limited to, a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, a tertiary butyl group, a secondary butyl group, an octyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, etc. Among these, an alkyl group having 1 to 10 carbon atoms is preferred.

[0129] Y, R 101 ~R 211 Examples of the aryl group represented by the formula (1) include, but are not limited to, a phenyl group, a naphthyl group, an indenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a phenanthryl group, a triphenylenyl group, etc. Among these, an aryl group having 6 to 18 carbon atoms is preferred.

[0130] Y, R 105 ~R 211Examples of the heterocyclic group represented by the formula (1) include, but are not limited to, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a carbazolyl group, an acridinyl group, a phenanthrolyl group, etc. Among these, a heterocyclic group having 3 to 15 carbon atoms is preferred.

[0131] Y, R 101 ~R 104 Examples of the aryloxy group represented by the formula (I) include, but are not limited to, a phenoxy group and a thienyloxy group.

[0132] Examples of the silyl group represented by Y include, but are not limited to, a trimethylsilyl group and a triphenylsilyl group.

[0133] Examples of the substituent that the above alkyl group, aryl group, heterocyclic group, and aryloxy group may further have include alkyl groups such as a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, and a tertiary butyl group; aralkyl groups such as a benzyl group; aryl groups such as a phenyl group and a biphenyl group; heterocyclic groups such as a pyridyl group and a pyrrolyl group; alkoxy groups such as a methoxy group, an ethoxy group, and a propoxy group; and aryloxy groups such as a phenoxy group, but are not limited to these.

[0134] Next, a method for synthesizing the organic compound according to the present embodiment will be described. The organic compound according to the present embodiment can be synthesized, for example, according to the reaction scheme shown below. In the scheme, Ar' is a group having an azine skeleton represented by the general formulas

[0102] to

[0104] .

[0135] [ka]

[0136] [ka]

[0137] [ka]

[0138] [ka]

[0139] Here, by appropriately changing the above-mentioned substituents Ar and Ar', a compound represented by the general formula

[0101] can be obtained. Details of the synthesis method will be explained in the Examples.

[0140] Next, since the organic compound according to this embodiment has the following characteristics, it emits blue light with high color purity, has a large reduction potential, and is a chemically stable compound. Furthermore, by using this organic compound, it is possible to provide an organic light-emitting device with excellent color purity and element durability. (3) Groups having an azine skeleton, which is an electron-withdrawing substituent, are bonded to a position where the electron orbital distribution of the LUMO of the basic skeleton is relatively smaller than the electron orbital distribution of the HOMO. (4) The nitrogen atom in the group having an azine skeleton is oriented in a direction that does not form a hydrogen bond with the basic skeleton.

[0141] The characteristics will be described below. Here, the basic skeleton in this embodiment is a skeleton in which hydrogen atoms are bonded to the positions indicated by *1 to *6 in the general formula

[0101] instead of groups having an azine skeleton, and R1 to R4 are all hydrogen atoms.

[0142] (3) Groups having an azine skeleton, which is an electron-withdrawing substituent, are bonded to a position where the electron orbital distribution of the LUMO of the basic skeleton is relatively smaller than the electron orbital distribution of the HOMO. In inventing the organic compound represented by the general formula

[0101] , the present inventors focused on the basic skeleton itself.

[0143] First, in order to emit blue light with good color purity, the basic skeleton itself must be in a blue region with high color purity. In this embodiment, the desired emission wavelength region is a blue region with high color purity, specifically, the maximum emission wavelength in a dilute solution is within a band of 430 nm to 450 nm. The basic skeleton of this embodiment is a skeleton suitable for emitting the desired blue light.

[0144] On the other hand, the basic skeleton of this embodiment exhibits blue light emission with good color purity, but the band gap of the compound is large and the electron acceptance is low. It is necessary to increase the stability of the organic light-emitting material against electric charges, and for this purpose, it is required to increase the electron acceptance. In an organic light-emitting device, an organic compound sandwiched between electrodes repeats oxidation and reduction between molecules, and the organic compound repeats an excited state and a ground state by carrier recombination, and light is emitted. Therefore, a compound that is unstable against the transfer of electric charges undergoes a chemical change in the oxidation-reduction process or the excited state, and changes into a different compound. As a result, the original element characteristics are impaired, the luminance of the organic light-emitting device is reduced, and the element durability during continuous operation is deteriorated. In order to reduce such deterioration, stability against electric charges is required, and high electron acceptance is necessary.

[0145] In this embodiment, we focused on increasing the reduction potential as one of the design guidelines for materials with high electron-accepting properties, and found a compound of the general formula

[0101] . Specifically, by introducing a group having an azine skeleton as an electron-withdrawing group into the basic skeleton, the electron-accepting property can be improved and the stability against electric charge can be further increased.

[0146] Examples of electron-withdrawing groups include halogen groups such as fluorine atoms, but fluorine atoms have oxidizing power and therefore deteriorate the element life. Also, carboxyl groups are included, but they are difficult to purify by sublimation and are therefore not suitable as deposition materials. In this embodiment, a group having an azine skeleton has been found as an electron-withdrawing substituent that does not deteriorate the element characteristics, particularly the element durability life, and has excellent deposition properties. More preferred are groups having an azine skeleton represented by the general formulas

[0102] to

[0104] .

[0147] Table 4 is a table comparing the emission wavelengths and reduction potentials of the exemplary compounds of this embodiment and the comparative compounds. As an example of the exemplary compounds, a compound in which an electron-withdrawing substituent having an azine skeleton is introduced at *3 and *4 of the general formula

[0101] , which are the desired positions of the basic skeleton, is shown. On the other hand, a compound that does not have a group having an azine skeleton is shown as a comparative compound.

[0148] The emission wavelength was measured by photoluminescence measurement of a diluted toluene solution at room temperature with an excitation wavelength of 350 nm using a Hitachi F-4500. The reduction potential was measured by CV (cyclic voltammetry). The CV measurement was performed using a 0.1 M tetrabutylammonium perchlorate solution in DMF (reduction potential measurement), and the reference electrode was Ag / Ag + The counter electrode was Pt and the working electrode was glassy carbon. The voltage sweep rate was 1.0 V / s. The measurement device used was an electrochemical analyzer, Model 660C, manufactured by ALS.

[0149] [Table 4]

[0150] From Table 4, it can be seen that the compound of this embodiment has a reduction potential that is 0.1 V or more deeper than the comparative compound, without increasing the wavelength, because the group having an azine skeleton, which is an electron-withdrawing substituent, is bonded to a desired position. In other words, it can be seen that the compound of this embodiment exhibits blue light emission with high color purity and has improved electron-accepting properties. Details of the results in Table 4 and related considerations are described below.

[0151] Comparative compound 1-A is a compound in which a phenyl group having no electron-withdrawing substituent is bonded to the 9th and 19th positions of the diacenaphtho[1,2-b:1',2'-k]chrysene skeleton, which is the basic skeleton, and is cited as an example of a compound having properties similar to the basic skeleton itself. Here, exemplary compound D1 has a structure in which an electron-withdrawing group having an azine skeleton is substituted at the 9th and 19th positions of the basic skeleton, and the reduction potential is -1.98V, which is higher than that of comparative compound 1-A. At the same time, the maximum emission wavelength of exemplary compound D1 is 444nm, which is shorter than that of comparative compound 1-A, and it can be seen that the color purity has shifted in a good direction.

[0152] In addition, the comparative compound 1-C has a structure in which a phenyl group is further substituted at the 3rd and 13th positions of the basic skeleton compared to the comparative compound 1-A. The band gap is narrowed due to the conjugation length being extended in the long axis direction of the basic skeleton. As a result, the reduction potential is larger than that of the comparative compound 1-A, but the maximum emission wavelength is longer and the color purity is shifted in the direction of deterioration. In contrast, the exemplary compound D11, which is a compound of this embodiment, has a structure in which a group having an azine skeleton is substituted at the 9th and 19th positions of the comparative compound 1-C instead of the phenyl group. It can be seen that the reduction potential is -1.87 V, which is larger than that of the comparative compound 1-C, while the wavelength is shorter than that of the comparative compound 1-C.

[0153] This result can be considered as follows. The electron orbital distribution of the HOMO and LUMO of the diacenaphtho[1,2-b:1',2'-k]chrysene skeleton, which is the basic skeleton, differs depending on the position of the basic skeleton. Therefore, it is considered that the degree of influence on the HOMO and LUMO differs depending on the position where the electron-withdrawing substituent is introduced. That is, in the example compounds D1 and D11, a group having an azine skeleton, which is an electron-withdrawing substituent, is introduced at the 9th and 19th positions of the basic skeleton, and at these positions, the electron orbital distribution of the LUMO of the basic skeleton is relatively small, and the electron orbital distribution of the HOMO is large. Therefore, the effect of electron-withdrawing on the HOMO is relatively large, and the optical band gap is widened, resulting in a shorter wavelength than each of the comparative compounds, and at the same time, the reduction potential is considered to be large due to the influence of the electron-withdrawing effect on the LUMO. Table 4 shows the results of introducing an electron-withdrawing group having an electron-withdrawing azine skeleton at the 9th and 19th positions of the basic skeleton, that is, at the positions *3 and *4 of the general formula

[0101] , but the same effect can be obtained by introducing it at the positions *1, *2, *5, and *6.

[0154] To support the above-mentioned effect, the distribution of electron orbitals of the HOMO and LUMO of the diacenaphtho[1,2-b:1',2'-k]chrysene skeleton, which is the basic skeleton, was visualized using molecular orbital calculations. The results are shown in Figure 6. Figure 6(a) is a visualization of the distribution of electron orbitals of the HOMO, and Figure 6(b) is a visualization of the distribution of electron orbitals of the LUMO.

[0155] It is the design method of the density functional which is based on the density functional (Density Functional Theory,DFT) is based on the B3LYP, and its range is 6-31G* It is also denoted by Gaussian09(Gaussian09,RevisionC.01,MJFr isch,GWTrucks,HBSchlegel,GEScuseria,MARobb,JRCheeseman,G.Scalmani,V.Barone,B.Mennucci,GAPetersson,H.Nak atsuji, M. Caricato, X. Li, HHPratchian, AFIzmaylov, J. Bloino, G. Zheng, JLSonnenberg, M. Hada, M. Ehara, K. Toyota, R.F Ukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. Montgomery, Jr., JEPeralta, F. Ogli hoop, M. Bearpark, JJ Heyd, E. Brothers, KNKudin, VNStaroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A.Re ndell, JCBurant, SSIyengar, J. Thomas, M. Cossi, N. Rega, JMMillam, M. Klene, JEKnox, JBCross, V. Bakken, C. Adamo, J. Jar starch,R.Gomperts,REStratmann,O.Yazyev,AJAustin,R.Cammi,C.Pomelli,JWOchterski,RLMartin,K.Morokuma,VGZak rzewski,GAVoth,P.Salvador,JJDannenberg,S.Dapprich,ADDaniels,O.Farkas,JBForesman,JVOrtiz,JCioslowski,and DJFox,Gaussian,Inc.,Wallingford CT,2010.)

[0156] From Figure 6, it can be seen that at the positions (positions of the arrows) indicated by *1 to *6 in the general formula

[0101] , the electron orbital distribution of the HOMO (Figure 6(a)) is greater than the electron orbital distribution of the LUMO at the relatively same positions (Figure 6(b)). This is because the numerical values ​​accompanying the arrows are the orbital coefficients of each position, and the orbital coefficients of the HOMO at the positions indicated by *1 to *6 are greater than the orbital coefficients of the LUMO. Therefore, when an electron-withdrawing group having an azine skeleton is introduced at these positions, the reduction potential increases due to the electron-withdrawing effect on the LUMO, but the effect of electron-withdrawing on the HOMO is even greater, resulting in a wider optical band gap and a shorter emission wavelength.

[0157] (4) The nitrogen atom in the group having an azine skeleton is oriented in a direction that does not form a hydrogen bond with the basic skeleton. The compound of this embodiment has a group having an azine skeleton, which is an electron-withdrawing substituent, at the positions shown by *1 to *6 in the general formula

[0101] , and the group having an azine skeleton is a group represented by the general formulas

[0102] to

[0104] . That is, the nitrogen atom in the group having an azine skeleton is arranged in a direction that does not form a hydrogen bond with the basic skeleton. Table 5 is a table comparing the emission wavelengths and reduction potentials of the exemplary compounds of this embodiment and comparative compounds having different positions of the nitrogen atom.

[0158] [Table 5]

[0159] From Table 5, it can be seen that the exemplary compound D13 of this embodiment has a shorter wavelength and a larger reduction potential than the comparative compound 1-A. This effect is as described above. On the other hand, it can be seen that the comparative compound 1-B having a group with an azine skeleton has a longer maximum emission wavelength but does not have a larger reduction potential. These differences can be explained as follows.

[0160] First, in the comparative compound 1-B, the nitrogen atom in the group having the azine skeleton is arranged on the side of the basic skeleton, and the lone pair on the nitrogen atom forms hydrogen bonds with the 10th and 20th positions on the basic skeleton, increasing the planarity. As a result, it is considered that the band gap narrows due to the increase in the π-conjugated system of the entire molecule, and the maximum emission wavelength becomes longer. Normally, when the band gap narrows, the HOMO becomes higher and the LUMO shifts to a lower direction. However, in the comparative compound 1-B, the lone pair on the nitrogen atom is arranged in a direction to form a hydrogen bond with the hydrogen atom on the basic skeleton, so it is considered that both the HOMO and LUMO work in the direction of increasing. Note that a high HOMO / LUMO means that each orbital is closer to the vacuum level, and a low HOMO / LUMO means that each orbital is farther from the vacuum level.

[0161] This is because the lone pair on the nitrogen atom acts in the direction of donating electrons from the lone pair on the nitrogen atom to the hydrogen atom on the basic skeleton through hydrogen bonds due to hydrogen bonds between the lone pair on the nitrogen atom. Therefore, contrary to the nature of the original electron-withdrawing group, electrons are donated to the basic skeleton, so that both the HOMO and LUMO shift in the higher direction. In other words, the tendency of the LUMO to be lowered as the band gap narrows is countered by the electron-donating effect via hydrogen bonds. As a result, it can be seen that the maximum emission wavelength becomes longer and the reduction potential does not increase, shifting in the opposite direction to the purpose of this embodiment.

[0162] As described above, the organic compound according to the present embodiment is a compound having the above properties (3) to (4), and therefore is an organic compound that exhibits blue light emission with high color purity, has a large electron-accepting property, and is chemically stable. By using this, an organic light-emitting device that exhibits blue light emission with high efficiency, high element durability, and high color purity can be obtained.

[0163] Specific examples of the organic compound according to this embodiment are shown below, but this embodiment is not limited to these.

[0164] [ka]

[0165] [ka]

[0166] [ka]

[0167] [ka]

[0168] [ka]

[0169] Among the above-mentioned exemplary compounds, those belonging to group D are compounds having an azine skeleton represented by the formulae

[0105] to

[0109] introduced therein. They can combine high electron accepting properties with blue light emission of high color purity.

[0170] On the other hand, among the above example compounds, those belonging to group E are compounds into which a group having an azine skeleton represented by the formulae

[0110] to

[0118] has been introduced. Since the number of nitrogen atoms per group having an azine skeleton introduced is lower than that of group D, the electron accepting property is alleviated, but Tg is improved with an increase in molecular weight, and it is possible to combine high heat resistance with blue light emission with good color purity.

[0171] In addition, among the above exemplary compounds, F Those belonging to this group are compounds having an azine skeleton represented by the formulae

[0119] to

[0124] introduced therein. These compounds can have both high heat resistance and high electron accepting property.

[0172] <Organic light-emitting element> Next, the organic light-emitting device of this embodiment will be described. The organic light-emitting device of this embodiment has at least a pair of electrodes, an anode and a cathode, 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 consisting of multiple layers as long as it has a light-emitting layer. Here, when the organic compound layer is a laminate consisting of multiple layers, the organic compound layer may have a hole injection layer, a hole transport layer, an electron blocking layer, a hole exciton blocking layer, an electron transport layer, an electron injection layer, etc. in addition to the light-emitting layer. The light-emitting layer may be a single layer or a laminate consisting of multiple layers.

[0173] 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 contained in any of the above-mentioned light-emitting layer, hole injection layer, hole transport layer, electron blocking layer, hole exciton blocking layer, electron transport layer, electron injection layer, etc. The organic compound according to the present embodiment is preferably contained in the light-emitting layer.

[0174] In the organic light-emitting device of this embodiment, when the organic compound according to this embodiment is contained in the light-emitting layer, the light-emitting layer may be a layer consisting of only the organic compound according to this embodiment, or may be a layer consisting of the organic compound according to this embodiment and other compounds. Here, when the light-emitting layer is a layer consisting of the organic compound according to this embodiment and other compounds, the organic compound according to this embodiment may be used as a host of the light-emitting layer or as a guest. It may also be used as an assist material that can be contained in the light-emitting layer. Here, the host is a compound having the largest mass ratio among the compounds constituting the light-emitting layer. Also, the guest is a compound having a smaller mass ratio than the host among the compounds constituting the light-emitting layer, and is a compound that is responsible for the main emission. Also, the assist material is a compound having a smaller mass ratio than the host among the compounds constituting the light-emitting layer, and assists the emission of the guest. The assist material is also called a second host.

[0175] When the organic compound according to this embodiment is used as a guest in the light-emitting layer, the concentration of the guest is preferably from 0.01% by mass to 20% by mass, and more preferably from 0.1% by mass to 5% by mass, based on the entire light-emitting layer.

[0176] In addition, when the organic compound according to the present embodiment is used as a guest in the light-emitting layer, it is preferable to use a material having a higher LUMO than the organic compound according to the present embodiment (a material having a LUMO closer to the vacuum level) as a host. This is because the organic compound according to the present embodiment can accept more electrons supplied to the host in the light-emitting layer by using a material having a higher LUMO than the organic compound according to the present embodiment as a host. In particular, the organic compound represented by the general formula

[0101] has a high electron-accepting property, i.e., a low LUMO, so that the organic compound according to the present embodiment can accept more electrons supplied to the host in the light-emitting layer by using a material having a higher LUMO than the organic compound represented by the general formula

[0101] as a host.

[0177] The present inventors have conducted various studies and found that when the organic compound according to this embodiment is used as a host or guest of the light-emitting layer, particularly as a guest of the light-emitting layer, an element that exhibits high efficiency and high luminance light output and is extremely durable can be obtained. This light-emitting layer may be a single layer or multiple layers, and it is also possible to mix the light emitted by the light-emitting layer with the blue light-emitting color of this embodiment by including a light-emitting material having another light-emitting color. The multiple layers refer to a state in which the light-emitting layer and another light-emitting layer are laminated. In this case, the light-emitting color of the organic light-emitting element is not limited to blue. More specifically, it may be white or an intermediate color. In the case of white, the other light-emitting layer emits a color other than blue, that is, red or green. In addition, the film is formed by deposition or coating. Details of this will be described in detail in the examples below.

[0178] The organic compound according to this embodiment can be used as a constituent material of an organic compound layer other than the light-emitting layer constituting the organic light-emitting device of this embodiment. Specifically, it may be used as a constituent material of an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, a hole blocking layer, etc. In this case, the emission color of the organic light-emitting device is not limited to blue. More specifically, it may be white or a neutral color.

[0179] In addition to the organic compound according to the present embodiment, conventionally known low-molecular-weight and high-molecular-weight hole-injecting or hole-transporting compounds, host compounds, light-emitting compounds, electron-injecting or electron-transporting compounds, etc. may be used together as necessary. Examples of these compounds are given below.

[0180] As the hole injection transport material, a material having high hole mobility is preferable so that the injection of holes from the anode can be easily performed and the injected holes can be transported to the light emitting layer. In addition, a material having a high glass transition temperature is preferable so as to reduce deterioration of the film quality such as crystallization in the organic light emitting device. 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 material is also preferably used in the electron blocking layer. Specific examples of compounds used as the hole injection transport material are shown below, but of course, the present invention is not limited to these.

[0181] [ka]

[0182] Examples of luminescent materials mainly involved in luminescence function include organic compounds represented by the general formula [1], as well as condensed ring compounds (e.g., fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, organoaluminum complexes such as tris(8-quinolinolato)aluminum, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, and polymer derivatives such as poly(phenylenevinylene) derivatives, poly(fluorene) derivatives, and poly(phenylene) derivatives. Specific examples of compounds used as luminescent materials are shown below, but are of course not limited to these.

[0183] [ka]

[0184] Examples of the light-emitting layer host or light-emitting assist material contained in the light-emitting layer include aromatic hydrocarbon compounds or derivatives thereof, as well as carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organic aluminum complexes such as tris(8-quinolinolato)aluminum, organic beryllium complexes, etc. Specific examples of compounds used as the light-emitting layer host or light-emitting assist material contained in the light-emitting layer are shown below, but the present invention is not limited to these.

[0185] [ka]

[0186] The electron transporting material can be arbitrarily selected from those capable of transporting electrons injected from the cathode to the light-emitting layer, and is selected in consideration of the balance with the hole mobility of the hole transporting material. Examples of materials having electron transporting properties include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organic aluminum complexes, and condensed ring compounds (e.g., fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the above electron transporting materials are also preferably used in the hole blocking layer. Specific examples of compounds used as electron transporting materials are shown below, but are of course not limited to these.

[0187] [ka]

[0188] <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, and the like may be provided on the cathode. When a color filter is provided, a planarizing layer may be provided between the protective layer and the color filter. The planarizing layer may be made of acrylic resin or the like.

[0189] [substrate] Examples of the substrate include quartz, glass, silicon wafer, resin, and metal. In addition, 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, any material can be used as long as it can form a contact hole to ensure electrical continuity between the anode and the wiring and can ensure insulation from wiring that is not connected. For example, resin such as polyimide, silicon oxide, silicon nitride, etc. can be used.

[0190] [electrode] A pair of electrodes can be used. The pair of electrodes may be an anode and a cathode. When an electric field is applied in the direction in which the organic light-emitting element emits light, the electrode with a higher potential is the anode, and the other is the cathode. It can also be said that the electrode that supplies holes to the light-emitting layer is the anode, and the electrode that supplies electrons is the cathode.

[0191] The material constituting the anode should have as large a work function as possible. For example, metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, tungsten, etc., mixtures containing these metals, alloys combining these metals, metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide can be used. Conductive polymers such as polyaniline, polypyrrole, and polythiophene can also be used.

[0192] These electrode materials may be used alone or in combination of two or more kinds. The anode may be composed of one layer or multiple layers.

[0193] When used as a reflective electrode, for example, chromium, aluminum, silver, titanium, tungsten, molybdenum, or an alloy or laminate of these can be used. When used as a transparent electrode, a transparent conductive layer of oxide such as indium tin oxide (ITO) or indium zinc oxide can be used, but is not limited to these. Photolithography technology can be used to form the electrode.

[0194] On the other hand, the material for the cathode should have a small work function. Examples of the material include alkali metals such as lithium, alkaline earth metals such as calcium, aluminum, titanium, manganese, silver, lead, chromium, and other metals or mixtures containing these metals. Alternatively, alloys combining these metals can be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper, zinc-silver, and the like can be used. Metal oxides such as indium tin oxide (ITO) can also be used. These electrode materials may be used alone or in combination of two or more types. The cathode may have a single layer structure or a multi-layer structure. Among these, it is preferable to use silver, and it is even more preferable to use a silver alloy to reduce the aggregation of silver. As long as the aggregation of silver can be reduced, the ratio of the alloy is not important. For example, it may be 1:1.

[0195] The cathode may be a top-emission element using an oxide conductive layer such as ITO, or a bottom-emission element using a reflective electrode such as aluminum (Al), and is not particularly limited. The method for forming the cathode is not particularly limited, but it is more preferable to use a direct current or alternating current sputtering method, etc., since the film coverage is good and the resistance can be easily reduced.

[0196] [Protective layer] A protective layer may be provided on the cathode. For example, by bonding glass provided with a moisture absorbent on the cathode, it is possible to suppress the intrusion of water and the like into the organic compound layer and suppress the occurrence of display defects. In another embodiment, a passivation film such as silicon nitride may be provided on the cathode to suppress the intrusion of water and the like into the organic compound layer. For example, after the cathode is formed, the device may be transported to another chamber without breaking the vacuum, and a silicon nitride film having a thickness of 2 μm may be formed by the CVD method to serve as a protective layer. A protective layer may be provided using the atomic deposition method (ALD method) after the film formation by the CVD method.

[0197] [Color Filter] A color filter may be provided on the protective layer. For example, a color filter taking into consideration the size of the organic light-emitting element may be provided on another substrate and then bonded to the substrate on which the organic light-emitting element is provided, or a color filter may be patterned on the protective layer described above using a photolithography technique. The color filter may be made of a polymer.

[0198] [Planarization layer] A planarizing layer may be provided between the color filter and the protective layer. The planarizing layer may be made of an organic compound, and may be a low molecular weight or a high molecular weight compound, but is preferably a high molecular weight compound.

[0199] The planarization layer may be provided above and below the color filter, and may be made of the same or different materials.Specific examples of the materials include polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, and urea resin.

[0200] [Opposite substrate] The flattening layer may have a counter substrate on it. The counter substrate is called a counter substrate because it is provided at a position corresponding to the aforementioned substrate. The material of the counter substrate may be the same as that of the aforementioned substrate.

[0201] [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 one embodiment of the present invention are formed by the method shown below.

[0202] The organic compound layer constituting the organic light-emitting device according to one embodiment of the present invention can be formed by dry processes such as vacuum deposition, ionization deposition, sputtering, plasma, etc. Alternatively, instead of the dry process, a wet process can be used in which a layer is formed by dissolving the compound in an appropriate solvent and applying a known coating method (e.g., spin coating, dipping, casting, LB method, inkjet method, etc.).

[0203] Here, when the layer is formed by a vacuum deposition method or a solution coating method, crystallization is unlikely to occur and the layer has excellent stability over time. When the layer is formed by a coating method, the layer can be formed by combining with a suitable binder resin.

[0204] Examples of the binder resin include, but are not limited to, polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, and urea resin.

[0205] These binder resins may be used alone or in combination as homopolymers or copolymers, and may further include known additives such as plasticizers, antioxidants, and ultraviolet absorbers, if necessary.

[0206] <Use of the organic light-emitting device according to one embodiment of the present invention> The organic light-emitting device according to an embodiment of the present invention can be used as a component of a display device or a lighting device, and can also be used as an exposure light source for an electrophotographic image forming device, a backlight for a liquid crystal display device, a light-emitting device having a white light source and a color filter, etc.

[0207] The display device may be an image information processing device having an image input unit that inputs image information from an area CCD, a linear CCD, a memory card, etc., an information processing unit that processes the input information, and displays the input image on a display unit. The display device may have a plurality of pixels, and at least one of the plurality of pixels may have the organic light-emitting element of this embodiment and a transistor connected to the organic light-emitting element.

[0208] The display unit of the imaging device or inkjet printer may have a touch panel function. The driving method of the touch panel function may be an infrared type, a capacitance type, a resistive film type, or an electromagnetic induction type, and is not particularly limited. The display device may be used in the display unit of a multifunction printer.

[0209] Next, the display device according to the present 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 element and a TFT element connected to the organic light-emitting element. The TFT element is an example of an active element.

[0210] 1 includes a substrate 11 such as glass and a moisture-proof film 12 for protecting a TFT element or an organic compound layer provided thereon. Reference numeral 13 denotes a metal gate electrode. Reference numeral 14 denotes a gate insulating film, and reference numeral 15 denotes a semiconductor layer.

[0211] 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. An anode 21 constituting an organic light emitting element 26 and the source electrode 17 are connected via a contact hole 20.

[0212] The method of electrical connection between the electrodes (anode 21, cathode 23) included in the organic light-emitting element 26 and the electrodes (source electrode 17, drain electrode 16) included in the TFT element 18 is not limited to the embodiment shown in Fig. 1. In other words, it is sufficient that either the anode 21 or the cathode 23 is electrically connected to either the source electrode 17 or the drain electrode 16 of the TFT element 18.

[0213] 1, the organic compound layer 22 is illustrated as a single layer, but the organic compound layer 22 may be a multi-layer structure. A first protective layer 24 and a second protective layer 25 are provided on the cathode 23 to reduce deterioration of the organic light-emitting element 26.

[0214] In the display device 10 of FIG. 1, transistors are used as switching elements, but MIM elements may be used instead as switching elements.

[0215] The transistors used in the display device 10 of Fig. 1 are not limited to transistors using single crystal silicon wafers, but may be thin film transistors having an active layer on an insulating surface of a substrate. Examples of the active layer include single crystal silicon, amorphous silicon, non-single crystal silicon such as microcrystalline silicon, and non-single crystal oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Thin film transistors are also called TFT elements.

[0216] The transistors included in the display device 10 of Fig. 1 may be formed in a substrate such as a Si substrate. Here, "formed in a substrate" means that the substrate itself such as a Si substrate is processed to produce the transistors. In other words, having a transistor in a substrate can be seen as the substrate and the transistor being integrally formed.

[0217] The organic light-emitting element according to this embodiment has its emission brightness controlled by a TFT, which is an example of a switching element, and by providing the organic light-emitting element on a plurality of surfaces, an image can be displayed based on the emission brightness of each element. The switching element according to this embodiment is not limited to a TFT, and may be a transistor formed of low-temperature polysilicon or an active matrix driver formed on a substrate such as a Si substrate. On the substrate may also be within the substrate. Whether to provide a transistor within the substrate or to use a TFT is selected according to the size of the display unit. For example, if the size is about 0.5 inches, it is preferable to provide the organic light-emitting element on a Si substrate.

[0218] 2 is a schematic diagram showing an example of a display device according to the present embodiment. The display device 1000 may have a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008 between an upper cover 1001 and a lower cover 1009. Flexible printed circuits FPC1002 and 1004 are connected to the touch panel 1003 and the display panel 1005. 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, and may be provided in a different position if the display device is a portable device.

[0219] The display device according to the present embodiment may be used as a display unit of a photoelectric conversion device such as an imaging device having an optical unit with a plurality of lenses and an imaging element that receives light that has passed through the optical unit. The imaging device may have a display unit that displays information acquired by the imaging element. The display unit may be a display unit exposed to the outside of the imaging device or a display unit disposed within a viewfinder. The imaging device may be a digital camera or a digital video camera.

[0220] 3(a) is a schematic diagram showing an example of an 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 a display device according to this embodiment. In this case, the display device may display not only an image to be captured, but also environmental information, imaging instructions, and the like. The environmental information may include the intensity of external light, the direction of external light, the moving speed of the subject, the possibility that the subject will be blocked by an obstruction, and the like.

[0221] Since the timing suitable for imaging is short, it is better to display information as soon as possible. Therefore, it is preferable to use a display device using the organic light-emitting element of this embodiment. This is because the organic light-emitting element has a fast response speed. A display device using an organic light-emitting element can be used more preferably than a liquid crystal display device, which requires a high display speed.

[0222] The imaging device 1100 has an optical section (not shown). The optical section has multiple lenses, and forms an image on an imaging element housed in a housing 1104. The focal points of the multiple lenses can be adjusted by adjusting their relative positions. This operation can also be performed automatically.

[0223] The display device according to this embodiment may have color filters having red, green, and blue colors, the red, green, and blue colors being arranged in a delta arrangement.

[0224] The display device according to the present embodiment may be used as a display unit of an electronic device such as a mobile terminal. In this case, the display device may have both a display function and an operation function. Examples of the mobile terminal include a mobile phone such as a smartphone, a tablet, and a head-mounted display.

[0225] 3(b) is a schematic diagram showing an example of an electronic device according to this embodiment. The electronic device 1200 has a display unit 1201, an operation unit 1202, and a housing 1203. The housing 1203 may have a circuit, a printed circuit board having the circuit, a battery, and a communication unit. The operation unit 1202 may be a button or a touch panel type reaction unit. The operation unit may be a biometric recognition unit that recognizes a fingerprint to perform unlocking or the like. An electronic device having a communication unit may be called a communication device.

[0226] FIG. 4 is a schematic diagram showing an example of a display device according to the present embodiment. FIG. 4(a) shows a display device such as a television monitor or a PC monitor. The display device 1300 has a frame 1301 and a display unit 1302. The light-emitting device according to the present embodiment may be used for the display unit 1302. The display device 1300 has the frame 1301 and a base 1303 that supports the display unit 1302. The base 1303 is not limited to the form shown in FIG. 4(a). The lower side of the frame 1301 may also serve as the base. The frame 1301 and the display unit 1302 may be curved. The radius of curvature may be 5000 mm or more and 6000 mm or less.

[0227] 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 bendable, and is a so-called foldable display device. The display device 1310 has a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may have the light-emitting device according to the present embodiment. The first display unit 1311 and the second display unit 1312 may be one display unit without a joint. 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 the first and second display units may display one image.

[0228] FIG. 5(a) is a schematic diagram showing an example of a lighting device according to the present embodiment. The lighting device 1400 may have a housing 1401, a light source 1402, a circuit board 1403, an optical filter 1404 that transmits light emitted by the light source 1402, and a light diffusion unit 1405. The light source 1402 may have an organic light-emitting element according to the present embodiment. The optical filter 1404 may be a filter that improves the color rendering of the light source. The light diffusion unit 1405 can effectively diffuse the light of the light source, such as for lighting up, and deliver the light over a wide range. The optical filter 1404 and the light diffusion unit 1405 may be provided on the light emission side of the lighting. If necessary, a cover may be provided on the outermost part.

[0229] The lighting device is, for example, a device that illuminates a room. The lighting device may emit white light, natural white light, or any other color from blue to red. It may have a dimming circuit that adjusts the light intensity. The lighting device may have the organic light-emitting element of this embodiment and a power supply circuit connected thereto. The power supply circuit is a circuit that converts AC voltage into DC voltage. Moreover, white has a color temperature of 4200K, and natural white has a color temperature of 5000K. The lighting device may have a color filter.

[0230] The lighting device according to the present embodiment may also include a heat dissipation section that dissipates heat from within the device to the outside, and examples of the heat dissipation section include metals with high specific heat, liquid silicon, and the like.

[0231] 5B is a schematic diagram of an automobile, which is an example of a moving body according to this embodiment. The automobile has tail lamps, which are an example of a lamp. The automobile 1500 has tail lamps 1501, and may be configured to turn on the tail lamps when braking or the like is performed.

[0232] The tail lamp 1501 may have an organic light-emitting element according to this embodiment. The tail lamp 1501 may have a protective member for protecting the organic light-emitting element. The protective member may be made of any material as long as it has a certain degree of strength and is transparent, but is preferably made of polycarbonate or the like. Polycarbonate may be mixed with a furandicarboxylic acid derivative, an acrylonitrile derivative, or the like.

[0233] The automobile 1500 may have a body 1503 and a window 1502 attached thereto. The window 1502 may be a transparent display unless it is a window for checking the front and rear of the automobile. The transparent display may have an organic light-emitting element according to this embodiment. In this case, the constituent materials of the electrodes and the like of the organic light-emitting element are made of transparent members.

[0234] The moving body according to the present embodiment may be a ship, an aircraft, a drone, or the like. The moving body may have a body and a lamp provided on the body. The lamp may emit light to indicate the position of the body. The lamp has the organic light-emitting element according to the present embodiment.

[0235] As described above, by using a device using the organic light-emitting element according to this embodiment, it is possible to achieve a display with good image quality and stability even over a long period of time. EXAMPLES

[0236] The present invention will be described below with reference to examples, but the present invention is not limited to these.

[0237] [Example 1 (Synthesis of Exemplary Compound A1)]

[0238] [ka]

[0239] (1) Synthesis of compound H3 The following reagents and solvents were placed in a 500 ml recovery flask. Compound H1: 7.23g (25.1mmol) Compound H2: 5.00g (22.8mmol) Pd(PPh3)4: 790 mg (1.14 mmol) Sodium carbonate: 9.66 g (91.2 mmol) Toluene: 200 ml Ethanol: 100ml Water: 100ml Next, the reaction solution was heated to 90°C under a nitrogen stream and stirred at this temperature (90°C) for 5 hours. After the reaction was completed, the mixture was extracted with toluene and water, concentrated, and purified by silica gel column chromatography (heptane:toluene = 1:1), and then dispersed and washed with methanol to obtain 5.5 g (yield: 80%) of white compound H3.

[0240] (2) Synthesis of compound H4 The following reagents and solvents were placed in a 200 ml recovery flask. (Methoxymethyl)triphenylphosphonium chloride: 12.8g (41.5mmol) Tetrahydrofuran: 50 ml Next, the following reagents were slowly added dropwise to the reaction solution at room temperature under a nitrogen stream. Potassium t-butoxide [1.0M solution in tetrahydrofuran] Next, the reaction solution was stirred at this temperature (room temperature) for 1 hour, and the following mixed solution was slowly added dropwise at room temperature. Compound H3: 5.0g (16.6mmol) Tetrahydrofuran: 50 ml After the reaction was completed, the mixture was extracted with toluene and water, concentrated, and purified by silica gel column chromatography (heptane:toluene=1:1). After that, the mixture was dispersed and washed with methanol to obtain 4.48 g (yield: 82%) of white compound H4.

[0241] (3) Synthesis of compound H5 The following reagents and solvents were placed in a 200 ml recovery flask. Compound H4: 4.00 g (12.1 mmol) Dichloromethane: 100 ml Next, the reaction solution was cooled to 0° C. under a nitrogen stream, and the following reagents were added dropwise. Methanesulfonic acid: 1.75 g (18.2 mmol) Next, the reaction solution was stirred at room temperature for 3 hours. After the reaction was completed, 50 ml of methanol was added and stirred at 0° C. for 30 minutes. After that, the mixture was filtered and washed with water and methanol to obtain 3.09 g (yield: 86%) of white compound H5.

[0242] (4) Synthesis of compound H6 The following reagents and solvents were placed in a 500 ml recovery flask. Compound H5: 3.00g (10.1mmol) Bispinacolborane: 10.3g (40.4mmol) Pd(dba)2: 580 mg (1.01 mmol) P(Cy)3: 850 mg (3.03 mmol) Potassium acetate: 3.96 mg (40.4 mmol) Orthoxylene: 300ml Next, the reaction solution was heated to 150° C. under a nitrogen stream and stirred at this temperature (150° C.) for 7 hours. After the reaction was completed, the solution was filtered through Celite, concentrated, and dispersed and washed with heptane to obtain 3.93 g (yield: 81%) of white compound H6.

[0243] (5) Synthesis of compound H7 The following reagents and solvents were placed in a 500 ml recovery flask. Compound H6: 3.8g (7.91mmol) NCS: 5.28 g (39.6 mmol) Methanesulfonic acid: 227 mg (2.37 mmol) DMF: 380ml Next, the reaction solution was heated to 65°C under a nitrogen stream and stirred at this temperature (65°C) for 7 hours. After the reaction was completed, the solution was filtered. After purifying the solution by silica gel column chromatography (toluene), it was dispersed and washed with heptane to obtain 2.17g (yield: 50%) of white compound H7.

[0244] (6) Synthesis of compound H9 The following reagents and solvents were placed in a 200 ml recovery flask. Compound H7: 2.00g (3.64mmol) Compound H8: 4.17g (14.6mmol) PdCl2(PPh3)2: 128 mg (0.18 mmol) Sodium carbonate: 1.54 g (14.6 mmol) DMSO: 100ml Next, the reaction solution was heated to 90°C under a nitrogen stream and stirred at this temperature (90°C) for 5 hours. After the reaction was completed, 100 ml of methanol was added and stirred at room temperature for 30 minutes. Then, it was filtered. After purifying the product by silica gel column chromatography (heptane:chlorobenzene=3:1), it was dispersed and washed with methanol to obtain 1.24 g (yield: 48%) of white compound H9.

[0245] (7) Synthesis of compound H10 The following reagents and solvents were placed in a 100 ml recovery flask. Compound H9: 1.00g (1.41mmol) Pd(dba)2: 81 mg (0.14 mmol) P(Cy)3: 119 mg (0.42 mmol) Potassium acetate: 415 mg (4.23 mmol) DMAc: 50ml Next, the reaction solution was heated to 170°C under a nitrogen stream and stirred at this temperature (170°C) for 2 hours. After the reaction was completed, the mixture was filtered. By dispersing and washing the mixture with heptane / toluene, 523 mg (yield: 68%) of dark green compound H10 was obtained.

[0246] (8) Synthesis of Example Compound A1 The following reagents and solvents were placed in a 200 ml recovery flask. Compound H10: 100mg (0.18mmol) Compound H11: 229mg (1.08mmol) Pd(OAc)2: 4 mg (0.02 mmol) s-phos: 18 mg (0.05 mmol) Potassium carbonate: 149 g (1.08 mmol) DMSO: 10ml Next, the reaction solution was heated to 100°C under a nitrogen stream and stirred at this temperature (100°C) for 6 hours. After the reaction was completed, 100 ml of methanol was added and stirred at room temperature for 30 minutes. Then, it was filtered. After purifying the product by silica gel column chromatography (chlorobenzene), it was dispersed and washed with heptane / toluene to obtain 76 mg of yellow exemplary compound A1 (yield: 52%).

[0247] 1 x 10 of example compound A1 -5 The emission spectrum of the toluene solution in mol / L was measured by photoluminescence at an excitation wavelength of 350 nm using a Hitachi F-4500, and a spectrum with a maximum intensity at 444 nm was obtained.

[0248] Incidentally, mass spectrometry of the exemplary compound A1 was carried out using a MALDI-TOF-MS (Autoflex LRF manufactured by Bruker). [MALDI-TOF-MS] Measured value: m / z=809 Calculated value: C 62 H 32 O2=809

[0249] [Example 2 (Synthesis of Exemplary Compound A2)] Except for changing the raw material H1 to the raw material H12 in the above scheme and changing the raw material H2 to the raw material H13 in the following scheme, the exemplary compound A2 was synthesized with reference to Example 1. The actual measured value of the mass spectrometry measured in the same manner as in Example 1 was m / z=809.

[0250] [ka]

[0251] [Example 3 (Synthesis of Exemplary Compound A3)]

[0252] [ka]

[0253] (1) Synthesis of compound H18 Intermediate H18 was synthesized in the same manner as in Example 1, except that raw materials H1 and H2 were changed to the above H16 and H17, respectively.

[0254] (2) Synthesis of compound H20 The following reagents and solvents were placed in a 500 ml recovery flask. Compound H18: 3.6g (10.0mmol) Sodium ethanethiolate H19: 3.36g (40.0mmol) DMF: 280ml Next, the reaction solution was heated to 60°C under a nitrogen stream and stirred at this temperature for 7 hours. After the reaction was completed, an aqueous solution of ammonium chloride was added and filtered. This was dispersed and washed with 100 ml of water to obtain 2.46 g (yield: 75%) of white compound H20.

[0255] (3) Synthesis of compound H21 The following reagents and solvents were placed in a 500 ml recovery flask. Compound H20: 2.4g (7.29mmol) Pyridine: 3.5 ml Methylene chloride: 240 ml Next, 4.78 ml (29.1 mmol) of trifluoromethanesulfonic anhydride was added dropwise to the reaction solution under ice cooling, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, 200 ml of ice water was added, and the organic layer was extracted. The organic layer was concentrated and purified by silica gel column chromatography (toluene, heptane mixture), to obtain 3.54 g (yield: 82%) of white compound H21.

[0256] (4) Synthesis of compound H22 The following reagents and solvents were placed in a 500 ml recovery flask. Compound H21: 3.5g (6.37mmol) Bispinacolborane: 9.71g (38.2mmol) Pd(dppf)2Cl2: 453 mg (0.637 mmol) Potassium acetate: 2.50 g (25.5 mmol) Dioxane: 200ml Next, the reaction solution was heated to 100° C. under a nitrogen stream and stirred at this temperature for 7 hours. After the reaction was completed, the solution was filtered through Celite, concentrated, and dispersed and washed with heptane to obtain 3.18 g (yield: 91%) of gray compound H22.

[0257] (5) Synthesis of compound H23 The following reagents and solvents were placed in a 200 ml recovery flask. Compound H22: 2.00g (2.83mmol) Compound H8: 2.43g (8.48mmol) Pd(PPh3)2Cl2: 199 mg (0.28 mmol) Sodium carbonate: 1.80 g (17.0 mmol) DMSO: 100ml Next, the reaction solution was heated to 90°C under a nitrogen stream and stirred at this temperature for 5 hours. After the reaction was completed, 100 ml of water was added and stirred at room temperature for 30 minutes. Then, it was filtered. After purifying the product by silica gel column chromatography (heptane:chlorobenzene mixture), it was dispersed and washed with methanol to obtain 0.76 g (yield: 38%) of yellow compound H23.

[0258] (6) Synthesis of compound H24 The following reagents and solvents were placed in a 100 ml recovery flask. Compound H23: 0.75g (1.06mmol) Pd(PPh3)2Cl2: 77 mg (0.11 mmol) DBU: 5.0ml DMAc: 50ml Next, the reaction solution was heated to 170°C under a nitrogen stream and stirred at this temperature (170°C) for 2 hours. After the reaction was completed, the mixture was filtered. By dispersing and washing the mixture with heptane / toluene, 417 mg (yield: 72%) of dark green compound H24 was obtained.

[0259] (7) Synthesis of Example Compound A3 The following reagents and solvents were placed in a 300 ml recovery flask. Compound H24: 300mg (0.55mmol) Compound H11:466mg(2.20mmol) Pd(OAc)2: 4 mg (0.02 mmol) s-phos: 18 mg (0.05 mmol) Potassium phosphate: 0.458g (2.16mmol) Xylene: 150 ml Water: 15ml Next, the reaction solution was heated to 120°C under a nitrogen stream and stirred at this temperature for 7 hours. After the reaction was completed, the mixture was filtered. After purifying the mixture by silica gel column chromatography (toluene), it was dispersed and washed with heptane to obtain 227 mg (yield: 51%) of yellow exemplary compound A3.

[0260] Example compound A3 1 x 10 -5 The emission spectrum of the toluene solution in mol / L was measured by photoluminescence at an excitation wavelength of 350 nm using a Hitachi F-4500, and a spectrum with maximum intensity at 445 nm was obtained.

[0261] Mass spectrometry was also performed using MALDI-TOF-MS (Bruker Autoflex LRF). [MALDI-TOF-MS] Measured value: m / z=809 Calculated value: C 62 H 32 O2=809

[0262] [Examples 4 to 21 (Synthesis of Exemplary Compounds)] As shown in Tables 6 to 8, for the exemplary compounds shown in Examples 4 to 21, the exemplary compounds were synthesized in the same manner as in Examples 1 to 3, except that the raw materials H1, H12, and H16 in Examples 1 to 3 were changed to raw material 1, the raw materials H2, H13, and H17 to raw material 2, the raw material H8 to raw material 3, and the raw material H11 to raw material 4. The actual measured values: m / z of the mass spectrometry results measured in the same manner as in Examples 1 to 3 are also shown.

[0263] [Table 6]

[0264] [Table 7]

[0265] [Table 8]

[0266] [Example 22 (Synthesis of Exemplary Compound C14)]

[0267] [ka]

[0268] (1) Synthesis of compound H26 The following reagents and solvents were placed in a 300 ml recovery flask. Compound H24: 300mg (0.55mmol) Compound H25: 211mg (0.55mmol) Pd(OAc)2: 4 mg (0.02 mmol) s-phos: 18 mg (0.05 mmol) Potassium phosphate: 0.229 g (1.08 mmol) Xylene: 150 ml Water: 15ml Next, the reaction solution was heated to 120°C under a nitrogen stream and stirred at this temperature for 3 hours. After the reaction was completed, the mixture was filtered. After purifying the mixture by silica gel column chromatography (toluene), it was dispersed and washed with heptane to obtain 148 mg of compound H26 (yield: 35%).

[0269] (2) Synthesis of Example Compound C14 The following reagents and solvents were placed in a 100 ml recovery flask. Compound H26: 140mg (0.18mmol) Compound H27: 129mg (0.36mmol) Pd(OAc)2: 2 mg (0.01 mmol) s-phos: 9 mg (0.25 mmol) Potassium phosphate: 0.114g (0.54mmol) Xylene: 70ml Water: 7ml Next, the reaction solution was heated to 120°C under a nitrogen stream and stirred at this temperature for 5 hours. After the reaction was completed, the mixture was filtered. After purifying the mixture by silica gel column chromatography (toluene), it was dispersed and washed with heptane to obtain 74 mg (yield: 43%) of yellow exemplary compound C14.

[0270] Exemplary compound C14 was subjected to mass spectrometry using MALDI-TOF-MS (Autoflex LRF, manufactured by Bruker). [MALDI-TOF-MS] Measured value: m / z=962 Calculated value: C 58 H 34 O2Se=962

[0271] [Example 23 (Synthesis of Exemplary Compound D1)]

[0272] [ka]

[0273] (1) Synthesis of compound M3 The following reagents and solvents were placed in a 500 ml recovery flask. Compound M1: 7.23g (25.1mmol) Compound M2: 5.00g (22.8mmol) Pd(PPh3)4: 790 mg (1.14 mmol) Sodium carbonate: 9.66 g (91.2 mmol) Toluene: 200 ml Ethanol: 100ml Water: 100ml Next, the reaction solution was heated to 90°C under a nitrogen stream and stirred at this temperature (90°C) for 5 hours. After the reaction was completed, the mixture was extracted with toluene and water, concentrated, and purified by silica gel column chromatography (heptane:toluene = 1:1), and then dispersed and washed with methanol to obtain 5.5 g (yield: 80%) of white compound M3.

[0274] (2) Synthesis of compound M4 The following reagents and solvents were placed in a 200 ml recovery flask. (Methoxymethyl)triphenylphosphonium chloride: 12.8g (41.5mmol) Tetrahydrofuran: 50 ml Next, the following reagents were slowly added dropwise to the reaction solution at room temperature under a nitrogen stream. Potassium t-butoxide [1.0M solution in tetrahydrofuran] Next, the reaction solution was stirred at this temperature (room temperature) for 1 hour, and the following mixed solution was slowly added dropwise at room temperature. Compound M3: 5.0g (16.6mmol) Tetrahydrofuran: 50 ml After the reaction was completed, the mixture was extracted with toluene and water, concentrated, and purified by silica gel column chromatography (heptane:toluene=1:1). After dispersion and washing with methanol, 4.48 g of white compound M4 was obtained (yield: 82%).

[0275] (3) Synthesis of compound M5 The following reagents and solvents were placed in a 200 ml recovery flask. Compound M4: 4.00g (12.1mmol) Dichloromethane: 100 ml Next, the reaction solution was cooled to 0° C. under a nitrogen stream, and the following reagents were added dropwise. Methanesulfonic acid: 1.75 g (18.2 mmol) Next, the reaction solution was stirred at room temperature for 3 hours. After the reaction was completed, 50 ml of methanol was added and stirred at 0° C. for 30 minutes. After that, the mixture was filtered and washed with water and methanol to obtain 3.09 g (yield: 86%) of white compound M5.

[0276] (4) Synthesis of compound M6 The following reagents and solvents were placed in a 500 ml recovery flask. Compound M5: 3.00g (10.1mmol) Bispinacolborane: 10.3g (40.4mmol) Pd(dba)2: 580 mg (1.01 mmol) P(Cy)3: 850 mg (3.03 mmol) Potassium acetate: 3.96 mg (40.4 mmol) Orthoxylene: 300ml Next, the reaction solution was heated to 150° C. under a nitrogen stream and stirred at this temperature (150° C.) for 7 hours. After the reaction was completed, the solution was filtered through Celite, concentrated, and dispersed and washed with heptane to obtain 3.93 g (yield: 81%) of a white compound M6.

[0277] (5) Synthesis of compound M7 The following reagents and solvents were placed in a 500 ml recovery flask. Compound M6: 3.8g (7.91mmol) NCS: 5.28 g (39.6 mmol) Methanesulfonic acid: 227 mg (2.37 mmol) DMF: 380ml Next, the reaction solution was heated to 65°C under a nitrogen stream and stirred at this temperature (65°C) for 7 hours. After the reaction was completed, the solution was filtered. After purifying the solution by silica gel column chromatography (toluene), it was dispersed and washed with heptane to obtain 2.17 g (yield: 50%) of a white compound M7.

[0278] (6) Synthesis of compound M9 The following reagents and solvents were placed in a 200 ml recovery flask. Compound M7: 2.00g (3.64mmol) Compound M8: 4.17g (14.6mmol) PdCl2(PPh3)2: 128 mg (0.18 mmol) Sodium carbonate: 1.54 g (14.6 mmol) DMSO: 100ml Next, the reaction solution was heated to 90°C under a nitrogen stream and stirred at this temperature (90°C) for 5 hours. After the reaction was completed, 100 ml of methanol was added and stirred at room temperature for 30 minutes. It was then filtered. After purifying the product by silica gel column chromatography (heptane:chlorobenzene=3:1), it was dispersed and washed with methanol to obtain 1.24 g (yield: 48%) of white compound M9.

[0279] (7) Synthesis of compound M10 The following reagents and solvents were placed in a 100 ml recovery flask. Compound M9: 1.00 g (1.41 mmol) Pd(dba)2: 81 mg (0.14 mmol) P(Cy)3: 119 mg (0.42 mmol) Potassium acetate: 415 mg (4.23 mmol) DMAc: 50ml Next, the reaction solution was heated to 170°C under a nitrogen stream and stirred at this temperature (170°C) for 2 hours. After the reaction was completed, the mixture was filtered. By dispersing and washing the mixture with heptane / toluene, 523 mg (yield: 68%) of a dark green compound M11 was obtained.

[0280] (8) Synthesis of Example Compound D1 The following reagents and solvents were placed in a 200 ml recovery flask. Compound M10: 200mg (0.36mmol) Compound M11: 221mg (1.80mmol) Pd(OAc)2: 8 mg (0.04 mmol) s-phos: 36 mg (0.10 mmol) Potassium carbonate: 298 g (2.16 mmol) DMSO: 20ml Next, the reaction solution was heated to 100°C under a nitrogen stream and stirred at this temperature (100°C) for 6 hours. After the reaction was completed, 100 ml of methanol was added and stirred at room temperature for 30 minutes. Then, it was filtered. After purifying the product by silica gel column chromatography (chlorobenzene), it was dispersed and washed with heptane / toluene to obtain 146 mg (yield: 65%) of yellow exemplary compound D1.

[0281] 1 x 10 of example compound D1 -5 The emission spectrum of the toluene solution in mol / L was measured by photoluminescence at an excitation wavelength of 350 nm using a Hitachi F-4500, and a spectrum with a maximum intensity at 444 nm was obtained.

[0282] Incidentally, mass spectrometry of the exemplary compound D1 was carried out using a MALDI-TOF-MS (Autoflex LRF manufactured by Bruker). [MALDI-TOF-MS] Measured value: m / z=630 Calculated value: C 48 H 26 N2=630

[0283] [Example 24 (Synthesis of Exemplary Compound D2)] Except for changing the raw material M1 to the raw material M12 in the above scheme and changing the raw material M2 to the raw material M13 in the following scheme, the exemplary compound D2 was synthesized in the same manner as in Example 23. The actual measured value of the mass spectrometry measured in the same manner as in Example 23 was m / z=630.

[0284] [ka]

[0285] [Example 25 (Synthesis of Exemplary Compound D3)]

[0286] [ka]

[0287] (1) Synthesis of compound M18 Intermediate M18 was synthesized in the same manner as in Example 23, except that M1 was changed to the above M16 and M2 was changed to the above M17.

[0288] (2) Synthesis of compound M20 The following reagents and solvents were placed in a 500 ml recovery flask. Compound M18: 3.6g (10.0mmol) Sodium ethanethiolate M19: 3.36g (40.0mmol) DMF: 280ml Next, the reaction solution was heated to 60°C under a nitrogen stream and stirred at this temperature for 7 hours. After the reaction was completed, an aqueous solution of ammonium chloride was added and filtered. This was dispersed and washed with 100 ml of water to obtain 2.46 g (yield: 75%) of white compound M20.

[0289] (3) Synthesis of compound M21 The following reagents and solvents were placed in a 500 ml recovery flask. Compound M20: 2.4g (7.29mmol) Pyridine: 3.5 ml Methylene chloride: 240 ml Next, 4.78 ml (29.1 mmol) of trifluoromethanesulfonic anhydride was added dropwise to the reaction solution under ice cooling, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, 200 ml of ice water was added, and the organic layer was extracted. The organic layer was concentrated and purified by silica gel column chromatography (toluene, heptane mixture), to obtain 3.54 g (yield: 82%) of white compound M21.

[0290] (4) Synthesis of compound M22 The following reagents and solvents were placed in a 500 ml recovery flask. Compound M21: 3.5g (6.37mmol) Bispinacolborane: 9.71g (38.2mmol) Pd(dppf)2Cl2: 453 mg (0.637 mmol) Potassium acetate: 2.50 g (25.5 mmol) Dioxane: 200ml Next, the reaction solution was heated to 100° C. under a nitrogen stream and stirred at this temperature for 7 hours. After the reaction was completed, the solution was filtered through Celite, concentrated, and dispersed and washed with heptane to obtain 3.18 g (yield: 91%) of a gray compound M22.

[0291] (5) Synthesis of compound M23 The following reagents and solvents were placed in a 200 ml recovery flask. Compound M22: 2.00g (2.83mmol) Compound M8: 2.43g (8.48mmol) Pd(PPh3)2Cl2: 199 mg (0.28 mmol) Sodium carbonate: 1.80 g (17.0 mmol) DMSO: 100ml Next, the reaction solution was heated to 90°C under a nitrogen stream and stirred at this temperature for 5 hours. After the reaction was completed, 100 ml of water was added and stirred at room temperature for 30 minutes. Then, it was filtered. After purifying the product by silica gel column chromatography (heptane:chlorobenzene mixture), it was dispersed and washed with methanol to obtain 0.76 g (yield: 38%) of yellow compound M23.

[0292] (6) Synthesis of compound M24 The following reagents and solvents were placed in a 100 ml recovery flask. Compound M23: 0.75g (1.06mmol) Pd(PPh3)2Cl2: 77 mg (0.11 mmol) DBU: 5.0ml DMAc: 50ml Next, the reaction solution was heated to 170°C under a nitrogen stream and stirred at this temperature (170°C) for 2 hours. After the reaction was completed, the mixture was filtered. This was dispersed and washed with heptane / toluene to obtain 417 mg (yield: 72%) of dark green compound M24.

[0293] (7) Synthesis of Example Compound D3 The following reagents and solvents were placed in a 300 ml recovery flask. Compound M24: 300mg (0.55mmol) Compound M11: 271mg (2.20mmol) Pd(OAc)2: 4 mg (0.02 mmol) s-phos: 18 mg (0.05 mmol) Potassium phosphate: 0.458g (2.16mmol) Xylene: 150 ml Water: 15ml Next, the reaction solution was heated to 120°C under a nitrogen stream and stirred at this temperature for 7 hours. After the reaction was completed, the mixture was filtered. After purifying the mixture by silica gel column chromatography (toluene), it was dispersed and washed with heptane to obtain 211 mg (yield: 61%) of a yellow exemplary compound D3.

[0294] 1 x 10 of example compound D3 -5 The emission spectrum of the toluene solution in mol / L was measured by photoluminescence at an excitation wavelength of 350 nm using a Hitachi F-4500, and a spectrum with maximum intensity at 444 nm was obtained.

[0295] Mass spectrometry was also performed using MALDI-TOF-MS (Bruker Autoflex LRF). [MALDI-TOF-MS] Measured value: m / z=630 Calculated value: C 48 H 26 N2=630

[0296] [Examples 26 to 36 (Synthesis of Exemplary Compounds)] As shown in Tables 9 to 10, for the exemplary compounds shown in Examples 26 to 36, the exemplary compounds were synthesized in the same manner as in Examples 23 to 25, except that the raw materials M1, M12, and M16 in Examples 23 to 25 were changed to raw material 1, the raw materials M2, M13, and M17 to raw material 2, the raw material M8 to raw material 3, and the raw material M11 to raw material 4. The actual measured values: m / z of the mass spectrometry results measured in the same manner as in Examples 23 to 25 are also shown.

[0297] [Table 9]

[0298] [Table 10]

[0299] [Example 37 (Synthesis of Exemplary Compound D22)]

[0300] [ka]

[0301] (1) Synthesis of compound M25 The following reagents and solvents were placed in a 500 ml recovery flask. Compound M24: 556mg (1.01mmol) Bispinacolborane: 1.03g (4.04mmol) Pd(dba)2: 58 mg (0.10 mmol) P(Cy)3: 85 mg (0.30 mmol) Potassium acetate: 392 mg (4.04 mmol) Orthoxylene: 300ml Next, the reaction solution was heated to 150° C. under a nitrogen stream and stirred at this temperature (150° C.) for 7 hours. After the reaction was completed, the solution was filtered through Celite, concentrated, and dispersed and washed with heptane to obtain 404 mg (yield: 55%) of a gray compound M25.

[0302] (2) Synthesis of Example Compound D22 The following reagents and solvents were placed in a 200 ml recovery flask. Compound M25: 200mg (0.27mmol) Compound M26: 87mg (1.80mmol) Pd(OAc)2: 8 mg (0.04 mmol) s-phos: 36 mg (0.10 mmol) Potassium carbonate: 298 g (2.16 mmol) DMSO: 50ml Next, the reaction solution was heated to 100°C under a nitrogen stream and stirred at this temperature (100°C) for 6 hours. After the reaction was completed, 100 ml of methanol was added and stirred at room temperature for 30 minutes. Then, it was filtered. After purifying the product by silica gel column chromatography (chlorobenzene), it was dispersed and washed with heptane / toluene to obtain 103 mg (yield: 60%) of yellow exemplary compound D22. Example compound D22 1 x 10 -5 The emission spectrum of the toluene solution in mol / L was measured by photoluminescence at an excitation wavelength of 350 nm using a Hitachi F-4500, and a spectrum with a maximum intensity at 442 nm was obtained.

[0303] [Example 38 (Synthesis of Exemplary Compound D23)]

[0304] [ka]

[0305] The following reagents and solvents were placed in a 200 ml recovery flask. Compound M25: 200mg (0.27mmol) Compound M26: 43mg (0.27mmol) Pd(OAc)2: 8 mg (0.04 mmol) s-phos: 36 mg (0.10 mmol) Potassium carbonate: 298 g (2.16 mmol) DMSO: 50ml

[0306] Next, the reaction solution was heated to 100° C. under a nitrogen stream and stirred at this temperature (100° C.) for 3 hours. Next, after cooling to room temperature, the following reagents were added. Compound M28: 93mg (0.54mmol) Pd(OAc)2: 8 mg (0.04 mmol) s-phos: 36 mg (0.10 mmol) Potassium carbonate: 298 g (2.16 mmol)

[0307] Next, the reaction solution was heated to 100°C under a nitrogen stream and stirred at this temperature (100°C) for 6 hours. After the reaction was completed, 100 ml of methanol was added and stirred at room temperature for 30 minutes. Then, it was filtered. After purifying the product by silica gel column chromatography (chlorobenzene), it was dispersed and washed with heptane / toluene to obtain 17 mg (yield: 10%) of yellow exemplary compound D23.

[0308] Mass spectrometry was also performed using MALDI-TOF-MS (Bruker Autoflex LRF). [MALDI-TOF-MS] Measured value: m / z=647 Calculated value: C 47 H 26 N4=647

[0309] [Examples 39 to 48 (Synthesis of Exemplary Compounds)] As shown in Tables 11 and 12, for the exemplary compounds shown in Examples 39 to 48, the exemplary compounds were synthesized in the same manner as in Examples 37 and 38, except that the raw material M25 in Example 37 was changed to raw material 5, the raw material M26 in Examples 37 and 38 was changed to raw material 6, and the raw material M28 in Example 38 was changed to raw material 7. In addition, the actual measured values: m / z of the mass spectrometry results measured in the same manner as in Examples 23 to 25 are shown.

[0310] [Table 11]

[0311] [Table 12]

[0312] [Example 49] In this example, an organic EL element having a bottom emission structure was fabricated 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 successively formed on a substrate.

[0313] First, an ITO film was formed on a glass substrate, and an ITO electrode (anode) was formed by carrying out 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 formed in this manner was used as an ITO substrate in the following process. Next, vacuum deposition was carried out by resistance heating in a vacuum chamber, and an organic EL layer and an electrode layer shown in Table 13 were successively formed on the ITO substrate. At this time, the electrode area of ​​the opposing electrodes (metal electrode layer, cathode) was set to 3 mm2. 2 It was made so that:

[0314] [Table 13]

[0315] The characteristics of the obtained element were measured and evaluated. The maximum emission wavelength of the light-emitting element was 445 nm, the maximum external quantum efficiency (EQE) was 5.9%, and blue light was emitted with a chromaticity of (X, Y) = (0.15, 0.06). Specifically, the current-voltage characteristics were measured using a Hewlett-Packard Microammeter 4140B, and the luminance was measured using a Topcon BM7. Furthermore, the current density was 80 mA / cm. 2 A continuous driving test was performed at 100 hours, and the time when the luminance degradation rate reached 5% (LT95) was measured. The measurement results are shown in Table 14.

[0316] [Examples 50 to 62, Comparative Example 1, Comparative Example 2] An organic light-emitting device was produced in the same manner as in Example 49, except that the compounds were appropriately changed to those shown in Table 14. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 49. The measurement results are shown in Table 14.

[0317] [Table 14]

[0318] From Table 14, the 5% degradation life (LT95) of Comparative Example 1 using Comparative Compound 1-a described in Patent Document 1 and Comparative Example 2 using Comparative Compound 1-b is 80 hours or less, which is poorer than the durability of the blue light-emitting element of this example. On the other hand, the element using the organic compound of this embodiment showed good durability. This is because the compound according to this embodiment has a benzochalcogenophene derivative group, has high electron acceptance, and is highly stable against electric charges.

[0319] Moreover, the external quantum efficiency of Comparative Example 1 was 5% or less, which was poorer than the luminous efficiency of the blue light-emitting device of this example. On the other hand, the device using the organic compound of this embodiment showed high-efficiency blue light-emitting characteristics. This is because the compound according to this embodiment has a benzochalcogenophene derivative group and can reduce concentration quenching in a thin film state.

[0320] [Example 63] In this example, an organic EL element having a top-emission structure was produced in which an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a first emitting layer, a second emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode were successively formed on a substrate.

[0321] A 40 nm thick laminated film of Al and Ti was formed on a glass substrate by sputtering, and then patterned using photolithography to form an anode. At this time, the electrode area of ​​the opposing electrode (metal electrode layer, cathode) was 3 mm2. 2 Next, the substrate with the cleaned electrodes and the material were attached to a vacuum deposition device (manufactured by ULVAC), and a 1.3 × 10 -4 Pa(1×10 -6 After evacuating to a pressure of 1000 psi (1000 mPa), the device was cleaned with UV / ozone. After that, each layer was formed in the layer configuration shown in Table 15, and finally, the device was sealed in a nitrogen atmosphere.

[0322] [Table 15]

[0323] The characteristics of the obtained element were measured and evaluated. The obtained element exhibited good white light emission. Furthermore, the initial luminance was 1000 cd / m 2 The brightness degradation rate after 100 hours was measured. The results are shown in Table 16.

[0324] [Examples 64 to 68, Comparative Example 3] An organic light-emitting device was produced in the same manner as in Example 63, except that the compounds shown in Table 16 were appropriately changed. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 63. The measurement results are shown in Table 16.

[0325] [Table 16]

[0326] From Table 16, the organic light-emitting device using the comparative compound 1-a had a luminance degradation rate of 23%. This is because when the comparative compound is used as a guest, the reduction potential is small and the electron-accepting property is insufficient, resulting in poor chemical stability. On the other hand, the device using the organic compound of this embodiment showed good durability. This is because the compound according to this embodiment has a benzochalcogenophene derivative group, has high electron-accepting property, and is highly stable against electric charges.

[0327] As described above, the organic compound according to the present embodiment has excellent electron accepting properties due to a large reduction potential, and has high luminous efficiency due to reduced concentration quenching, and is capable of emitting blue light with good color purity. Therefore, when the organic compound according to the present embodiment is used in an organic light-emitting device, the device has excellent luminous efficiency and driving durability.

[0328] [Example 69] In this example, an organic EL element having a bottom emission structure was fabricated 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 successively formed on a substrate.

[0329] First, an ITO film was formed 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 formed in this manner was used as an ITO substrate in the following process. Next, vacuum deposition was performed by resistance heating in a vacuum chamber to continuously form an organic EL layer and an electrode layer shown in Table 17 on the ITO substrate. At this time, the electrode area of ​​the opposing electrodes (metal electrode layer, cathode) was set to 3 mm2. 2 It was made so that:

[0330] [Table 17]

[0331] The characteristics of the obtained element were measured and evaluated. The maximum emission wavelength of the light-emitting element was 447 nm, the maximum external quantum efficiency (EQE) was 5.9%, and blue light emission with chromaticity of (X, Y) = (0.15, 0.08) was obtained. Specifically, the current-voltage characteristics were measured with a Hewlett-Packard Microammeter 4140B, and the emission luminance was measured with a Topcon BM7. Furthermore, the current density was 100 mA / cm. 2 A continuous driving test was conducted at 400 rpm, and the time (LT95) at which the brightness degradation rate reached 5% was measured, which was found to be over 100 hours.

[0332] [Examples 70 to 81, Comparative Example 4, Comparative Example 5] An organic light-emitting device was produced in the same manner as in Example 69, except that the compounds were appropriately changed to those shown in Table 18. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 69. The measurement results are shown in Table 18.

[0333] [Table 18]

[0334] From Table 18, the 5% degradation lifespan of Comparative Example 4 and Comparative Example 5 is 100 hours or less, and durability characteristics are poor, but the 5% degradation lifespan of the element using the organic compound according to this embodiment exceeds 100 hours. Moreover, in Comparative Example 4 and Comparative Example 5, the chromaticity coordinates are (0.14, 0.13) and (0.14, 0.15), respectively, and it can be seen that the color reproduction range of the Example is wider than that of the sRGB color reproduction range. This is due to the compound of the present invention emitting blue light at a shorter wavelength. The element using the organic compound according to the present invention shows good blue light emission characteristics and durability characteristics.

[0335] [Example 82] In this example, an organic EL element having a top-emission structure was produced in which an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a first emitting layer, a second emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode were successively formed on a substrate.

[0336] A 40 nm thick Ti film was formed on a glass substrate by sputtering, and then patterned using photolithography to form an anode. At this time, the electrode area of ​​the opposing electrode (metal electrode layer, cathode) was 3 mm2. 2 Next, the substrate with the cleaned electrodes and the material were attached to a vacuum deposition device (manufactured by ULVAC), and a 1.3 × 10 -4 Pa(1×10 -6 After evacuating to a pressure of 1000 psi (1000 mPa), the device was cleaned with UV / ozone. After that, each layer was formed in the layer configuration shown in Table 19, and finally, the device was sealed in a nitrogen atmosphere.

[0337] [Table 19]

[0338] The characteristics of the obtained element were measured and evaluated. The obtained element exhibited good white light emission. Furthermore, the initial luminance was 1000 cd / m 2 The brightness degradation rate after 100 hours was measured, and the result was 14%.

[0339] [Examples 83 to 89, Comparative Example 6] An organic light-emitting device was produced in the same manner as in Example 82, except that the compounds were appropriately changed to those shown in Table 20. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 82. The measurement results are shown in Table 20.

[0340] [Table 20]

[0341] As shown in Table 20, the luminance degradation rate was 25% in Comparative Example 6 using Comparative Compound 1-A. This is because when the Comparative Compound is used as a guest, the reduction potential is shallow and the electron accepting property is insufficient, resulting in poor chemical stability.

[0342] As described above, the organic compound according to the present invention is a compound that exhibits light emission suitable for blue light emission and has high chemical stability. Therefore, by using the organic compound according to the present invention as a constituent material of an organic light-emitting device, an organic light-emitting device having good light-emitting characteristics and excellent durability can be obtained. [Explanation of symbols]

[0343] 10: display device, 11: substrate, 12: moisture-proof film, 13: gate electrode, 14: gate insulating film, 15: semiconductor layer, 16: drain electrode, 17: source electrode, 18: TFT element, 19: insulator Insulating film, 20: contact hole, 21: anode, 22: organic compound layer, 23: cathode, 24: First protective layer, 25: second protective layer, 26: organic light-emitting element

Claims

1. An organic compound represented by the following general formula [1]: 【Chemistry 1】 In the general formula [1], R 1 From R 18 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a silyl group, and a group represented by any one of the following general formulae [2] to [3] and [102] to [104], with the proviso that at least one of them is a group represented by any one of the following general formulae [2] to [3] and [102] to [104]. The group represented by any one of the following general formulas [2] to [3] is R 19 From R 32 and a group represented by any of the following general formulae [102] to [104] is a group bonded at the position indicated by *. 【Chemistry 2】 In the general formulas [2] and [3], R 19 From R 32 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, and a silyl group. 19 From R 32 may form a ring with the adjacent group. X is independently selected from an oxygen atom, a sulfur atom, a selenium atom, and a tellurium atom. 【Chemistry 3】 (In the general formula [102], X 1 ~X 3 represents a hydrogen atom or a carbon atom having a substituent Y, or a nitrogen atom which constitutes a ring, and at least one of them is a nitrogen atom. The substituent Y is a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, and a silyl group. When there are a plurality of carbon atoms having the substituent Y, the substituents Y may be the same or different. R 105 ~R 106 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. 【Chemistry 4】 (In the general formula [103], X 4 ~X 7 represents a hydrogen atom or a carbon atom having a substituent Y, or a nitrogen atom which constitutes a ring, and at least one of them is a nitrogen atom. The substituent Y is a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, and a silyl group. When there are a plurality of carbon atoms having the substituent Y, the substituents Y may be the same or different. R 107 ~R 109 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. 【Chemistry 5】 (In the general formula [104], X 8 ~X 12 represents a hydrogen atom or a carbon atom having a substituent Y, or a nitrogen atom which constitutes a ring, and at least one of them is a nitrogen atom. The substituent Y is a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, and a silyl group. When there are a plurality of carbon atoms having the substituent Y, the substituents Y may be the same or different. R 110 ~R 111 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

2. The organic compound according to claim 1, characterized in that the group represented by any one of the general formulas [2] to [3] and [102] to [104] is a group represented by any one of the general formulas [2] to [3].

3. 3. The organic compound according to claim 1, wherein the number of groups represented by any one of the general formulae [2] to [3] and [102] to [104] is 1 or more and 4 or less.

4. The organic compound according to any one of claims 1 to 3, characterized in that the number of groups represented by any one of the general formulae [2] to [3] and [102] to [104] is 1 or more and 2 or less.

5. The R 3 , R 4 , R 7 , R 8 , R 9 , R 12 , R 13 , R 16 , R 17 , R 18 The organic compound according to any one of claims 1 to 4, characterized in that at least one of the above is a group represented by any one of general formulas [2] to [3] and [102] to [104].

6. The R 7 , R 8 , R 9 , R 16 , R 17 , R 18 The organic compound according to any one of claims 1 to 5, characterized in that at least one of the above is a group represented by any one of general formulas [2] to [3] and [102] to [104].

7. The group represented by any one of the general formulas [2] and [3] is R 22 , R 23 , R 29 The organic compound according to any one of claims 1 to 6, characterized in that the group is bonded at any one of the positions listed below.

8. 8. The organic compound according to claim 1, wherein the group represented by any one of the general formulas [2] and [3] is either a dibenzofuranyl group or a dibenzothiophenyl group.

9. The R 1 From R 18 are each independently selected from a hydrogen atom and a group represented by any one of general formulas [2] to [3] and [102] to [104]. The organic compound according to any one of claims 1 to 8,

10. The R 1 , R 6 , R 10 , R 15 10. The organic compound according to claim 1, wherein: is a hydrogen atom.

11. The R 3 , R 4 , R 12 , R 13 11. The organic compound according to claim 1, wherein: is a hydrogen atom.

12. The R 7 , R 9 , R 16 and R 18 12. The organic compound according to claim 1, wherein: is a hydrogen atom.

13. The organic compound described in claim 1, characterized in that the group represented by any one of the general formulas [2] to [3] and [102] to [104] is the group represented by the general formula [102].

14. The organic compound described in claim 13, characterized in that the group represented by the general formula [102] is a group represented by the following general formulas [105] to [109]. 【Chemistry 5-1】 (In general formulas [105] to [109], R 112 to R 127 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.)

15. The organic compound according to claim 1, characterized in that the group represented by the general formula [103] or [104] is a group represented by the following general formulas [110] to [118]. 【Chemistry 5-2】 (In general formulas [110] to [118], R 128 to R 181 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.)

16. The organic compound according to claim 1, characterized in that the group represented by the general formula [103] or [104] is a group represented by the following general formulas [119] to [124]. 【Chemistry 5-3】 (In general formulas [119] to [124], R 182 to R 211 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.)

17. An organic compound represented by the following general formula [101]: 【Chemistry 6】 (In general formula [101], at least one of the positions indicated by *1 to *6 is bonded to a group having an azine skeleton represented by the following general formulas [102] to [104] at the position indicated by *. When a plurality of groups having an azine skeleton represented by the general formulas [102] to [104] are bonded, the groups having an azine skeleton represented by the general formulas [102] to [104] may be the same or different. R 101 ~R 104 are each independently selected from a hydrogen atom, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aryloxy group. 【Chemistry 7】 (In the general formula [102], X 1 ~X 3 represents a hydrogen atom or a carbon atom having a substituent Y, or a nitrogen atom which constitutes a ring, and at least one of them is a nitrogen atom. The substituent Y is a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, and a silyl group. When there are a plurality of carbon atoms having the substituent Y, the substituents Y may be the same or different. R 105 ~R 106 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. 【Chemistry 8】 (In the general formula [103], X 4 ~X 7 represents a hydrogen atom or a carbon atom having a substituent Y, or a nitrogen atom which constitutes a ring, and at least one of them is a nitrogen atom. The substituent Y is a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, and a silyl group. When there are a plurality of carbon atoms having the substituent Y, the substituents Y may be the same or different. R 107 ~R 109 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. 【Chemistry 9】 (In the general formula [104], X 8 ~X 12 represents a hydrogen atom or a carbon atom having a substituent Y, or a nitrogen atom which constitutes a ring, and at least one of them is a nitrogen atom. The substituent Y is a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, and a silyl group. When there are a plurality of carbon atoms having the substituent Y, the substituents Y may be the same or different. R 110 ~R 111 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

18. The organic compound according to claim 17, characterized in that a group having an azine skeleton represented by any two of the positions indicated by *1 to *6 is bonded to the general formulas [102] to [104].

19. The organic compound according to claim 17 or 18, characterized in that the group bonded to at least one of the positions indicated by *1 to *6 is a group having an azine skeleton represented by the general formula [102].

20. 20. The organic compound according to claim 19, wherein the group having an azine skeleton represented by the general formula [102] is a group represented by any one of the following general formulae [105] to [109]. 【Chemistry 10】 (In the general formulae [105] to [109], R 112 ~R 127 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

21. The organic compound according to claim 17 or 18, characterized in that the group bonded to at least one of the positions indicated by *1 to *6 is a group having an azine skeleton represented by the general formula [103] or [104].

22. The organic compound according to claim 21, characterized in that the group having an azine skeleton represented by the general formula [103] or [104] is a group represented by the following general formulas [110] to [118]. 【Chemistry 11】 (In the general formulae [110] to [118], R 128 ~R 181 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

23. The organic compound according to claim 21, characterized in that the group having an azine skeleton represented by the general formula [103] or [104] is a group represented by the following general formulas [119] to [124]. 【Chemistry 12】 (In the general formulae [119] to [124], R 182 ~R 211 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

24. The group having an azine skeleton represented by the general formula [103] or [104] is 6 ~X 7 is the carbon atom, or 12 The organic compound according to claim 21, characterized in that: is a group in which the carbon atom is.

25. The R 101 ~R 104 25. The organic compound according to claim 17, wherein: is a hydrogen atom.

26. The R 101 ~R 104 The organic compound according to any one of claims 17 to 24, characterized in that: is a group that does not have a lone pair of electrons.

27. An anode and a cathode, an organic compound layer disposed between the anode and the cathode, 27. An organic light-emitting device, wherein at least one of the organic compound layers comprises the organic compound according to claim 1.

28. 28. The organic light-emitting device according to claim 27, wherein the layer having the organic compound is a light-emitting layer.

29. 29. The organic light-emitting device according to claim 27, which emits blue light.

30. 30. The organic light-emitting device according to claim 28, further comprising another light-emitting layer disposed in a stacked manner with the light-emitting layer, the other light-emitting layer emitting light of a color different from the color of light emitted by the light-emitting layer.

31. The organic light-emitting device according to claim 30, which emits white light.

32. 32. A display device comprising a plurality of pixels, at least one of the plurality of pixels comprising the organic light-emitting element according to claim 27 and a transistor connected to the organic light-emitting element.

33. an optical unit having a plurality of lenses, an image sensor that receives light that has passed through the optical unit, and a display unit that displays an image captured by the image sensor; 32. A photoelectric conversion device, comprising: a display section comprising the organic light-emitting element according to claim 27.

34. 32. An electronic device comprising: a display unit having the organic light-emitting element according to claim 27; a housing in which the display unit is provided; and a communication unit provided in the housing and configured to communicate with an external device.

35. 32. An illumination device comprising: a light source having the organic light-emitting element according to claim 27; and a light diffusion section or an optical filter that transmits light emitted by the light source.

36. 32. A moving body comprising: a lighting device having the organic light-emitting element according to claim 27; and a body on which the lighting device is provided.

37. A photoconductor and an exposure light source for exposing the photoconductor, 32. An image forming apparatus, comprising: an exposure light source comprising the organic light emitting element according to claim 27.

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