Organic compound and organic light-emitting element

Abstract

To provide an organic compound excellent in oxidation stability.SOLUTION: The organic compound is represented by formula (1), where rings A to C are each independently selected from the group consisting of substituted or unsubstituted C6-50 aryl groups and substituted or unsubstituted C3-50 heterocyclic groups; EWG is an electron-withdrawing group, an aryl group having at least one electron-withdrawing group, or a heterocyclic group having at least one or more electron-withdrawing groups; and n is an integer of 1 or more.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 (hereinafter sometimes referred to as an "organic electroluminescence element" or "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 into the organic compound layer, excitons of the light-emitting organic compound in the organic compound layer are generated, and when the excitons return to the ground state, the organic light-emitting element emits light.

[0003] Incidentally, up to now, there have been active efforts to create compounds suitable for organic light-emitting devices. Patent Document 1 describes compound Ref-1 as a compound having an indolocarbazole skeleton.

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

[0005] [Patent Document 1] International Publication No. 2019 / 111971 Summary of the Invention [Problem to be solved by the invention]

[0006] However, the compound specifically described in Patent Document 1 is a compound in which, when the central benzene in the indolocarbazole skeleton has a substituent, the substituent is an aryl group or an aryl group having an alkyl group, and therefore the oxidation stability of the compound leaves room for improvement.

[0007] The present invention has been made in view of the above problems, and an object of the present invention is to provide an organic compound having excellent oxidation stability. [Means for solving the problem]

[0008] The organic compound according to the present invention is characterized by being represented by formula (1).

[0009] [ka]

[0010] In formula (1), ring A to ring C are each independently selected from the group consisting of substituted or unsubstituted aryl groups having from 6 to 50 carbon atoms and substituted or unsubstituted heterocyclic groups having from 3 to 50 carbon atoms. When ring A to ring C have a substituent, the substituent is a deuterium atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, a heteroaryloxy group, a silyl group, an amino group, or a cyano group.

[0011] EWG is an electron-withdrawing group, an aryl group having at least one electron-withdrawing group, or a heterocyclic group having at least one or more electron-withdrawing groups.

[0012] n is an integer of 1 or greater. Effect of the Invention

[0013] According to the present invention, it is possible to provide an organic compound having excellent oxidation stability. [Brief description of the drawings]

[0014] [Figure 1] 1A is a schematic cross-sectional view showing an example of a pixel of a display device according to one embodiment of the present invention, and FIG. 1B is a schematic cross-sectional view showing an example of a display device using an organic EL element according to one embodiment of the present invention. [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] 1A is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention, the wearable device having an imaging device. [Figure 7] 1A is a schematic diagram showing an example of an image forming apparatus according to an embodiment of the present invention, FIG. 1B is a schematic diagram showing an example of an exposure light source of the image forming apparatus according to an embodiment of the present invention, and FIG. 1C is a schematic diagram showing an example of an exposure light source of the image forming apparatus according to an embodiment of the present invention. [Figure 8] FIG. 2 shows the HOMO orbital distribution and the LUMO orbital distribution of Compound A-1, Compound A-2, Compound Ref-4, and Compound Ref-5. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0015] In this specification, examples of halogen atoms include, but are not limited to, fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0016] The alkyl group may have from 1 to 20 carbon atoms, from 1 to 10 carbon atoms, or from 1 to 4 carbon atoms. Specific examples 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 tertiary pentyl group, a 3-methylpentan-3-yl group, a 1-adamantyl group, and a 2-adamantyl group.

[0017] The aryl group may have 6 to 50 carbon atoms, 6 to 20 carbon atoms, 6 to 14 carbon atoms, or 6 to 12 carbon atoms. Specific examples include, but are not limited to, a phenyl group, a naphthyl group, an indenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a phenanthryl group, a triphenylenyl group, a pyrenyl group, an anthranyl group, a perylenyl group, a chrysenyl group, and a fluoranthenyl group.

[0018] The heterocyclic group may have 3 to 50 carbon atoms, 3 to 20 carbon atoms, 3 to 17 carbon atoms, or 3 to 12 carbon atoms. Specific examples include, but are not limited to, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a carbazolyl group, an acridinyl group, and a phenanthrolyl group.

[0019] The amino group may be a substituted amino group substituted with an alkyl group or an aryl group, and may be a substituted amino group substituted with an alkyl group having from 1 to 4 carbon atoms or an aryl group having from 6 to 12 carbon atoms. Specific examples include 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, but are not limited to these.

[0020] The alkoxy group may have from 1 to 10 carbon atoms, or from 1 to 4 carbon atoms. Specific examples include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, a 2-ethyl-octyloxy group, and a benzyloxy group.

[0021] Specific examples of the aryloxy group include, but are not limited to, a phenoxy group.

[0022] Specific examples of the heteroaryloxy group include, but are not limited to, a thienyloxy group.

[0023] Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group and a triphenylsilyl group.

[0024] Examples of the substituent that the above alkyl group, alkoxy group, amino group, aryloxy group, silyl group, aryl group, and heterocyclic group may further have include halogen atoms such as fluorine, chlorine, bromine, and iodine; alkyl groups such as methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, and tertiary butyl group; alkoxy groups such as methoxy group, ethoxy group, and propoxy group; amino groups such as dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, and ditolylamino group; aryloxy groups such as phenoxy group; aryl groups such as phenyl group and biphenyl group; heterocyclic groups such as pyridyl group and pyrrolyl group; and cyano group, but are not limited to these.

[0025] (1)Organic compounds First, the organic compound according to the present invention will be described.

[0026] The organic compound according to the present invention is an organic compound represented by formula (1).

[0027] [ka]

[0028] In formula (1), rings A to C are each independently selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 50 carbon atoms and substituted or unsubstituted heterocyclic groups having 3 to 50 carbon atoms.

[0029] When ring A to ring C have a substituent, the substituent is a deuterium atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, a heteroaryloxy group, a silyl group, an amino group, or a cyano group.

[0030] When ring A to ring C have a substituent, the substituent may be an alkyl group, an aryl group, an amino group, or a heterocyclic group, and is preferably an alkyl group, an aryl group, or a heterocyclic group. Specifically, the substituent may be an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 14 carbon atoms, or a heterocyclic group having 3 to 12 carbon atoms. More specifically, the substituent may be a methyl group, an isopropyl group, a tert-butyl group, a phenyl group, a phenyl group having a tert-butyl group, a phenyl group having a methyl group, or a dibenzofuranyl group. The amino group may be a diphenylamino group, and the phenyl group in the diphenylamino group may have an alkyl group having 1 to 4 carbon atoms. Specifically, the alkyl group may be an isopropyl group or a tert-butyl group.

[0031] Ring A to Ring C may be a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 3 to 17 carbon atoms.

[0032] Specifically, ring A may be a benzene skeleton, a naphthalene skeleton, or a fluorene skeleton, and may be a benzene skeleton or a naphthalene skeleton. Ring B may be a benzene skeleton, a benzofuran skeleton, or a benzothiophene skeleton, and may be a benzene skeleton or a benzofuran skeleton. Ring C may be a benzene skeleton, a benzofuran skeleton, or a benzothiophene skeleton, and may be a benzene skeleton or a benzofuran skeleton.

[0033] The EWG is an electron-withdrawing group, an aryl group having at least one electron-withdrawing group, or a heterocyclic group having at least one or more electron-withdrawing groups. The EWG can be an aryl group having from 6 to 20 carbon atoms having at least one electron-withdrawing group, or a heterocyclic group having from 3 to 17 carbon atoms having at least one electron-withdrawing group.

[0034] Here, the electron-withdrawing group is a trifluoromethyl group, a trichloromethyl group, a nitro group, a cyano group, an aldehyde group, a ketone group, an ester group, a carboxylic acid group, a sulfonyl group, a sulfonic acid group, a pyridyl group, a triazinyl group, a halogen atom, etc. Among these, the electron-withdrawing group preferably has a Hammett's substituent constant of 0.01 or more and 0.70 or less, and more specifically, is preferably a trifluoromethyl group, a cyano group, or a fluorine atom.

[0035] On the other hand, a bipyridyl group is defined as a structure in which a pyridyl group, which is a heterocyclic group, has a pyridyl group, which is an electron-withdrawing group.Similarly, a benzonitrile group is defined as a structure in which a phenyl group, which is an aryl group, has a cyano group, which is an electron-withdrawing group.

[0036] n is an integer of 1 or more. The possible values ​​of n are defined by the structure of ring A. For example, when ring A is a benzene skeleton, n is 1 or 2, and when ring B is a naphthalene skeleton, n is an integer of 1 to 4.

[0037] Formula (1) may be a structure represented by the following formula (2) or formula (3). Formula (2) is a compound in which ring A in formula (1) is a benzene skeleton. Formula (3) is a compound in which ring A in formula (1) is a naphthalene skeleton.

[0038] [ka]

[0039] In formula (2), R 1 ~R 16 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, and a cyano group. 1 and R 2 , R2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 12 and R 13 , R 13 and R 14 may be bonded to each other to form a ring. 3 and R 4 , and R 10 and R 11 are preferably bonded to each other to form a ring. 5 and R 6 , and R 12 and R 13 are preferably bonded to each other to form a ring. The ring may be a substituted or unsubstituted aryl group having 6 to 12 carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 12 carbon atoms. Specifically, it may be a substituted or unsubstituted benzofuran skeleton or a substituted or unsubstituted benzothiophene skeleton. However, R 15 and R 16 At least one of is an electron-withdrawing group, an aryl group having at least one electron-withdrawing group, or a heterocyclic group having at least one electron-withdrawing group.

[0040] In formula (2), when the organic compound according to the present invention has a substituent, R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 , R 13 may have a substituent, R 3 , R 6 , R 10 , and R 13 , or R 3 and R 10, or R 4 and R 11 , or R 5 and R 12 Either pair may have a substituent.

[0041] In formula (3), R 21 ~R 38 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, and a cyano group. 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 26 and R 27 , R 28 and R 29 , R 29 and R 30 , R 30 and R 31 , R 32 and R 33 , R 33 and R 34 may be bonded to each other to form a ring. 23 and R 24 , and R 30 and R 31 are preferably bonded to each other to form a ring. 25 and R 26 , and R 32 and R 33 are preferably bonded to each other to form a ring. The ring may be a substituted or unsubstituted aryl group having 6 to 12 carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 12 carbon atoms. Specifically, it may be a substituted or unsubstituted benzofuran skeleton or a substituted or unsubstituted benzothiophene skeleton. However, R 35 ~R 38At least one of is an electron-withdrawing group, an aryl group having at least one electron-withdrawing group, or a heterocyclic group having at least one electron-withdrawing group.

[0042] In formula (3), when the organic compound according to the present invention has a substituent, R 23 , R 24 , R 25 , R 26 , R 30 , R 31 , R 32 , R 33 may have a substituent, R 23 , R 26 , R 30 , and R 33 , or R 23 and R 30 , or R 24 and R 31 , or R 25 and R 32 Either pair may have a substituent.

[0043] Next, the characteristics of the organic compound according to the present invention will be described.

[0044] In the organic compound according to the present invention, the ring A in formula (1) has an electron-withdrawing group, an aryl group having an electron-withdrawing group, or a heterocyclic group having an electron-withdrawing group, so that the HOMO (Highest Occupied Molecular Orbital) is low (far from the vacuum level). As a result, the organic compound according to the present invention has excellent oxidation stability.

[0045] Here, the HOMO values ​​of compounds A-1 and A-2, which are examples of organic compounds according to the present invention, and compound Ref-1, which is a comparative compound, were calculated using Gaussian 16 (Gaussian 16, Revision C.01, MJ Frisch, et al, Gaussian, Inc., Wallingford CT, 2019.), a molecular orbital calculation software manufactured by Gaussian, USA. B3LYP / 6-31G* was used as the keyword. The results are shown in Table 1.

[0046] [Table 1]

[0047] From Table 1, the HOMO of the compounds A-1 and A-2, which are examples of the organic compounds according to the present invention, is -5.25 eV and -5.29 eV, respectively, whereas the HOMO of the comparative compound, compound Ref-1, is -5.11 eV. This is considered to be because the organic compounds according to the present invention have an electron-withdrawing group. Therefore, compared with the HOMO of compound Ref-1, the organic compounds according to the present invention are organic compounds with excellent oxidation stability.

[0048] In addition, the organic compound according to the present invention can obtain the effects of the present invention by having at least one of an electron-withdrawing group, an aryl group having an electron-withdrawing group, or a heterocyclic group having an electron-withdrawing group. Using the above-mentioned calculation method, the HOMO values ​​of compounds A-2, A-3, and A-4, which are examples of the organic compound according to the present invention, and compounds Ref-2 and Ref-3, which are comparative compounds, were calculated. The results are shown in Table 2.

[0049] [Table 2]

[0050] As shown in Table 2, the organic compound according to the present invention exhibited a lower HOMO value than the comparative compounds Ref-2 and Ref-3. Therefore, the organic compound according to the present invention can obtain the effects of the present invention by having at least one of an electron-withdrawing group, an aryl group having an electron-withdrawing group, or a heterocyclic group having an electron-withdrawing group.

[0051] In addition, the organic compound according to the present invention is expected to exhibit a smaller half-width of the emission spectrum, since ring A in formula (1) has an electron-withdrawing group, an aryl group having an electron-withdrawing group, or a heterocyclic group having an electron-withdrawing group.

[0052] Patent Document 1 describes the following compounds Ref-4 and Ref-5, which are compounds in which ring B in formula (1) has an aryl group having an electron-withdrawing group.

[0053] [ka]

[0054] The organic compound according to the present invention is different from the compounds Ref-4 and Ref-5 in that the ring A in the formula (1) has an electron-withdrawing group, an aryl group having an electron-withdrawing group, or a heterocyclic group having an electron-withdrawing group. Therefore, the organic compound according to the present invention is expected to have a superior color purity to the compounds Ref-4 and Ref-5.

[0055] The HOMO orbital distribution and the LUMO orbital distribution of the compounds A-1 and A-2, which are examples of the organic compounds according to the present invention, and the compounds Ref-4 and Ref-5, which are comparative compounds, were depicted using Gaussian 16 (Gaussian 16, Revision C.01, MJ Frisch, et al, Gaussian, Inc., Wallingford CT, 2019.), which is a molecular orbital calculation software manufactured by Gaussian, Inc., USA. At this time, the value of the isoelectron density surface (Isosurface Value) was set to 0.02. The results are shown in FIG. 8.

[0056] As shown in Fig. 8, the HOMO orbital distribution and the LUMO orbital distribution of the compounds A-1 and A-2, which are examples of the organic compounds according to the present invention, are distributed at the center of the structure represented by formula (1). On the other hand, there is a difference between the HOMO orbital distribution and the LUMO orbital distribution of the comparative compounds Ref-4 and Ref-5 (black dotted circle in Fig. 8). In other words, the overlap between the HOMO orbital distribution and the LUMO orbital distribution of the comparative compounds Ref-4 and Ref-5 is small compared to the organic compounds according to the present invention.

[0057] In general, when the overlap between the HOMO orbital distribution and the LUMO orbital distribution is small, the structural relaxation between the excited state and the ground state increases, and the emission spectrum tends to be broad. On the other hand, when the overlap between the HOMO orbital distribution and the LUMO orbital distribution is large, the structural relaxation between the excited state and the ground state can be suppressed, and the emission spectrum tends to be sharp.

[0058] Therefore, the organic compound according to the present invention is expected to have a sharper emission spectrum than the comparative compounds Ref-4 and Ref-5, i.e., to have a better color purity.

[0059] More preferred embodiments of the organic compound according to the present invention will now be described.

[0060] Among the organic compounds according to the present invention, in formula (1), it is preferable that EWG is an aryl group having at least one electron-withdrawing group. The oscillator strengths of compounds A-1, A-4, and A-6, which are examples of organic compounds according to this embodiment, were determined using Gaussian 16 (Gaussian 16, Revision C.01, MJ Frisch, et al, Gaussian, Inc., Wallingford CT, 2019.), which is a molecular orbital calculation software manufactured by Gaussian, USA. B3LYP / 6-31G* was used as the keyword. The results are shown in Table 3.

[0061] [Table 3]

[0062] From Table 3, it is seen that the oscillator strength of compound A-1 is greater than that of compounds A-4 and A-6.

[0063] Here, the relationship between oscillator strength and quantum yield (luminescence efficiency) will be described. As described in paragraph

[0262] of JP 2020-47930 and paragraph

[0035] of JP 2022-46999, it is known that compounds with high oscillator strength exhibit high quantum yield (luminescence efficiency).

[0064] Therefore, among the organic compounds according to the present invention, it is preferable that EWG in formula (1) is an aryl group having at least one electron-withdrawing group from the viewpoint of quantum yield (luminous efficiency).

[0065] In addition, among the organic compounds according to the present invention, when EWG in formula (1) is an aryl group having at least one electron-withdrawing group, the aryl group is preferably a benzene skeleton. This is because the oscillator strength is higher than when the aryl group having at least one electron-withdrawing group is a naphthalene skeleton. The oscillator strengths of compounds A-1 and A-7, which are examples of the organic compounds according to this embodiment, were calculated using the same calculation method as in Table 3. The results are shown in Table 4.

[0066] [Table 4]

[0067] From Table 4, it was found that Compound A-1 exhibits a higher oscillator strength than Compound A-7. As described above, it is known that a high oscillator strength leads to a high quantum yield (luminous efficiency). Therefore, from the viewpoint of quantum yield (luminous efficiency), it is preferable that the aryl group having at least one electron-withdrawing group is a benzene skeleton.

[0068] In addition, among the organic compounds according to the present invention, when EWG in formula (1) is an aryl group having at least one electron-withdrawing group and the aryl group is a benzene skeleton, it is preferable that the electron-withdrawing group is bonded to the meta or para position relative to the ring A. This is because, in this case, the organic compound according to the present embodiment shows a higher oscillator strength. Using the same calculation method as in Table 3, the oscillator strengths of compounds A-1, A-2, and A-8, which are examples of the organic compound according to the present embodiment, were calculated. The results are shown in Table 5.

[0069] [Table 5]

[0070] From Table 5, it was found that Compound A-1 and Compound A-2 exhibit higher oscillator strength than Compound A-8. As described above, it is known that a high oscillator strength leads to a high quantum yield (luminous efficiency). Therefore, from the viewpoint of quantum yield (luminous efficiency), when EWG in Formula (1) is an aryl group having at least one electron-withdrawing group and the aryl group is a benzene skeleton, it is preferable that the electron-withdrawing group is bonded to the meta position or para position with respect to the ring A.

[0071] In addition, among the organic compounds according to the present invention, it is preferable that the electron-withdrawing group is a trifluoromethyl group, a cyano group, or a fluorine atom. This is because these electron-withdrawing groups have a moderate strength of electron-withdrawing property, so that the overlap between the HOMO orbital distribution and the LUMO orbital distribution becomes larger. As a result, the organic compound according to this embodiment is expected to be an organic compound with a smaller half-width. In other words, the organic compound according to this embodiment is expected to be an organic compound with superior color purity.

[0072] Specific examples of the organic compound according to the present invention are shown below, but the present invention is not limited to these.

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[0098] (2) Organic light-emitting element Next, an organic light-emitting device according to one embodiment of the present invention will be described. The organic light-emitting device according to one embodiment of the present invention has a first electrode, a second electrode, and an organic compound layer disposed between these electrodes. One of the first electrode and the second electrode is an anode, and the other is a cathode. In the organic light-emitting device according to this embodiment, the organic compound layer may be a single layer or a laminate consisting of multiple layers as long as it has a light-emitting layer. The organic compound according to the present invention may be included in the organic compound layer, and is preferably included in the 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. When the light-emitting layer is a multiple layer, a charge generation layer may be included between the light-emitting layers. The charge generating layer may be composed of a compound having a LUMO (Lowest Unoccupied Molecular Orbital) energy level lower than the LUMO energy level of the hole transport layer, and the LUMO energy level of the charge generating layer may be lower than the HOMO energy level of the hole transport layer. Here, the HOMO energy level and the LUMO energy level of the organic compound layer may be the HOMO energy level and the LUMO energy level of the organic compound having the largest weight ratio in the organic compound layer.

[0099] Here, the closer the HOMO energy level and the LUMO energy level are to the vacuum level, the higher they are described as being. The LUMO energy level of the charge generating layer being lower than the HOMO energy level of the hole transporting layer means that the LUMO energy level of the charge generating layer is farther from the vacuum level than the HOMO energy level of the hole transporting layer.

[0100] In this specification, the HOMO energy level and the LUMO energy level can be calculated by molecular orbital calculation. The molecular orbital calculation may be performed by density functional theory (DFT) or the like, using B3LYP as the functional and 6-31G* as the basis function.Gaussian09(Gaussian09,RevisionC.01,MJFrisch,GWTrucks,HBSchlegel,GEScuseria,MARobb, JRCheeseman,G.Scalmani,V.Barone,B.Mennucci,GAPetersson,H.Nakatsuji,M.Caricato,X.Li,HPHratchian,AF Izmailov,J.Bloino,G.Zheng,JLSonnenberg,M.Hada,M.Ehara,K.Toyota,R.Fukuda,J.Hasegawa,M.Ishida,T.Nak ajima,Y.Honda,O.Kitao,H.Nakai,T.Vreven,JAMontgomery,Jr.,JEPeralta,F.Ogliaro,M.Bearpark,JJHeyd,E.B rothers,KNKudin,VNStaroverov,T.Keith,R.Kobayashi,J.Normand,K.Raghavachari,A.Rendell,JCBurant,SSIy engar,J.Tomasi,M.Cossi,N.Rega,JMMillam,M.Klene,JEKnox,JBCross,V.Bakken,J.Adamo,J.Jaramillo,R.Gomp erts,RESstratmann,O.Yazyev,AJAustin,R.Cammi,J.Pomelli,JWOchterski,RLMartin,K.Morokuma,VGZakrzewski,GAVoth,P.Salvador,JJDannenberg,S.Dapprich,ADDaniels,O.Farkas,JBForesman,JVOrtizski,J.Condizski DJFox,Gaussian,Inc.,Wallingford CT,2010.)

[0101] The HOMO energy level and the LUMO energy level in this specification can be calculated using the ionization potential and the band gap. The HOMO energy level can be estimated by measuring the ionization potential. The ionization potential can be measured by dissolving the compound to be measured in a solvent such as toluene or by forming a deposition film of the compound to be measured on a substrate such as glass, and then using a measuring device such as AC-3. The band gap can be measured by dissolving the compound to be measured in a solvent such as toluene and applying excitation light. The band gap can be measured by measuring the absorption edge of the absorption spectrum of the excitation light. Alternatively, the compound to be measured can be measured by depositing the compound to be measured on a substrate such as glass and applying excitation light to the deposition film. The band gap can be measured by measuring the absorption edge of the absorption spectrum where the deposition film absorbs the excitation light.

[0102] The LUMO energy level can be calculated using the band gap and the ionization potential: subtracting the ionization potential from the band gap gives the LUMO energy level.

[0103] The LUMO energy level can also be estimated from the reduction potential. For example, the one-electron reduction potential is estimated using cyclic volmetry (CV) measurements. CV measurements can be performed, for example, in a DMF solution of 0.1 M tetrabutylammonium perchlorate, using an Ag / Ag+ reference electrode, a Pt counter electrode, and a glassy carbon working electrode. The LUMO energy level can be estimated by adding the difference between the reduction potential of the obtained compound and the reduction potential of ferrocene, which is -4.8 eV.

[0104] In the organic light-emitting device according to one embodiment of the present invention, when the organic compound according to the present invention is contained in the light-emitting layer, the light-emitting layer may be a layer consisting of only the organic compound according to the present invention, or may be a layer consisting of the organic compound according to the present invention and other compounds. Here, when the light-emitting layer is a layer consisting of the organic compound according to the present invention and other compounds, the organic compound according to the present invention may be used as a host material of the light-emitting layer, or may be used as a guest material. It may also be used as an assist material that can be contained in the light-emitting layer. Here, the host material is also called "host" or "first compound", and is a compound having the largest mass ratio among the compounds constituting the light-emitting layer. The guest material is also called "guest", "dopant material", "dopant", or "third compound", and 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. Therefore, the guest material may also be called a light-emitting material. The assist material is also called "assist" or "second compound", and is a compound having a smaller mass ratio than the host material among the compounds constituting the light-emitting layer, and assists the emission of the guest material. The assist material is also called a second host.

[0105] Here, the lowest excited singlet energy of the host material is S1(H), the lowest excited singlet energy of the guest material is S1(D), and the lowest excited singlet energy of the assist material is S1(A). The guest material may be regarded as an organic compound according to the present invention. In this case, it is preferable that the organic light-emitting device according to this embodiment satisfies S1(H)>S1(D) or S1(H)>S1(A)>S1(D). When the lowest excited singlet energy of the compound contained in the organic light-emitting device according to this embodiment satisfies the above relationship, excitons can be efficiently transferred to the guest material, resulting in an organic light-emitting device with better luminous efficiency.

[0106] When the organic compound according to the present invention is used as a guest material in the light-emitting layer, the concentration of the guest material may be from 0.01% by mass to less than 50% by mass, preferably from 0.01% by mass to 10% by mass, and more preferably from 0.01% by mass to 5% by mass, based on the total mass of the light-emitting layer.

[0107] When the light-emitting layer further contains an assist material, the assist material may be present in an amount of 1% by mass or more and less than 50% by mass, and preferably 10% by mass or more and less than 50% by mass, based on the total amount of the light-emitting layer. The guest may be present in an amount of 0.01% by mass or more and 20% by mass or less, and preferably 0.01% by mass or more and 5% by mass or less.

[0108] The present inventors have conducted various studies and found that when the organic compound according to the present invention is used as a host material or guest material of the light-emitting layer, particularly as a guest material of the light-emitting layer, an element that exhibits high efficiency and high luminance light output and is extremely durable can be obtained. The light-emitting layer may be a single layer or multiple layers, and by including a light-emitting material having another light-emitting color, it is possible to mix the light emitted with the blue light-emitting color of this embodiment. Multiple layers means 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 explained in detail in the examples described below.

[0109] The organic compound according to the present invention can be used as a constituent material of an organic compound layer other than the light-emitting layer constituting the organic light-emitting device according to the present embodiment. Specifically, it may be used as a constituent material of an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, a hole blocking layer, etc. In this case, the emission color of the organic light-emitting device is not limited to blue. More specifically, it may be white light or an intermediate color.

[0110] (3) Other compounds In addition to the organic compound according to the present invention, conventionally known low-molecular-weight and high-molecular-weight hole-injecting or hole-transporting compounds, host materials, light-emitting compounds, electron-injecting or electron-transporting compounds, etc. may be used together as necessary. Examples of these compounds are given below.

[0111] As the hole injection transport material, a material having a 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, in order to suppress the crystallization of the organic compound in the organic light emitting device, a material having a high glass transition temperature is preferable. Examples of low molecular weight and high molecular weight materials having hole injection transport performance include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. Furthermore, the above hole injection transport material is also preferably used for the electron blocking layer. In addition, when the hole injection layer is prepared by a coating method, a mixture of polyethylenedioxythiophene and polystyrenesulfonic acid (PEDOT:PSS), which is generally used as a hole injection material, may be used. 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.

[0112] [ka]

[0113] Among the hole injection transport materials, HT16 to HT18 can reduce the driving voltage by using them in a layer in contact with the anode. HT16 is widely used in organic light emitting devices. HT2 to HT7, HT10, HT12, HT22 to HT28 may be used in an organic compound layer adjacent to HT16. Hole transporting polyphenylenevinylene (PPV), polyfluorene (PF), polyvinylcarbazole (PVK), and polymer compounds such as derivatives thereof may be used. In addition to these, for example, inorganic insulating layers such as SiO2 and SiN, and organic silicon polymers such as siloxane may be used. Also, a plurality of materials may be used in one organic compound layer.

[0114] The luminescent materials mainly involved in the luminescence function include donor-acceptor type organic compounds, boron-containing complexes, indocarbazole fused ring compounds, fused ring compounds (e.g. fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, organoaluminum complexes such as tris(8-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. When preparing the luminescent layer by coating method, polymer compounds having luminescence properties are mainly used. This is because polymer compounds have high amorphous properties and are less likely to crystallize than low molecular weight systems. Specific examples of materials that can be used include polymer compounds such as polyphenylenevinylene (PPV), polyfluorene (PF), polyvinylcarbazole (PVK), and derivatives of these.

[0115] Specific examples of compounds that can be used as the light-emitting material are shown below, but the present invention is not limited to these.

[0116] [ka]

[0117] [ka]

[0118] [ka]

[0119] Specific examples of compounds that can be used as the light-emitting layer host or light-emitting assist dopant contained in the light-emitting layer are shown below, but the present invention is not limited to these.

[0120] [ka]

[0121] The host material of EM1 to EM47 may be a hydrocarbon compound having a condensed polycyclic hydrocarbon group, specifically, EM1 to EM26, EM46, and EM47.

[0122] 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-mentioned electron transporting materials are also suitable for use in hole blocking layers.

[0123] Specific examples of compounds usable as the electron transporting material are shown below, but the present invention is not limited to these.

[0124] [ka]

[0125] The electron injection material can be selected from those that can easily inject electrons from the cathode, taking into consideration the balance with hole injection properties. Organic compounds include n-type dopants and reducing dopants. Examples include compounds containing alkali metals such as lithium fluoride, lithium complexes such as lithium quinolinol, benzimidazolidene derivatives, imidazolidene derivatives, fulvalene derivatives, and acridine derivatives.

[0126] It can also be used in combination with the above-mentioned electron transport material.

[0127] (4) Structure of organic light-emitting element Hereinafter, the components constituting the organic light-emitting device of this embodiment will be described.

[0128] The organic light-emitting element is provided by forming an insulating layer, a first electrode, an organic compound layer, and a second electrode on a substrate. A protective layer, a color filter, a microlens, etc. may be provided on the second electrode. When a color filter is provided, a planarizing layer may be provided between the protective layer. The planarizing layer may be made of acrylic resin, etc. The same applies when a planarizing layer is provided between the color filter and the microlens.

[0129] [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 so that wiring can be formed between the first electrode and the insulating layer, and insulation from wiring that is not connected can be ensured. For example, resin such as polyimide, silicon oxide, silicon nitride, etc. can be used.

[0130] [electrode] A pair of electrodes can be used. The pair of electrodes is a first electrode and a second electrode. Specifically, the pair of electrodes may be an anode and a cathode. When an electric field is applied in the direction in which the organic light-emitting element emits light, the electrode with 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.

[0131] 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, and tungsten, mixtures containing these metals, alloys combining these metals, and 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.

[0132] 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.

[0133] When used as a reflective electrode, for example, chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys or laminates thereof can be used. The above materials can also function as a reflective film without serving as an electrode. 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.

[0134] 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, the ratio of silver to other metals may be 1:1, 3:1, and the like.

[0135] 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.

[0136] [Organic compound layer] The organic compound layer may be formed as a single layer or as multiple layers. When the organic compound layer has multiple layers, it may be called 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, etc., depending on its function. The organic compound layer is mainly composed of an organic compound, but may also contain inorganic atoms and inorganic compounds. For example, it may contain copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, etc. The organic compound layer may be disposed between the first electrode and the second electrode, or may be disposed in contact with the first electrode and the second electrode.

[0137] 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 this embodiment are formed by the method described below.

[0138] The organic compound layer constituting the organic light-emitting element according to this embodiment can be formed by a dry process such as a vacuum deposition method, an ionization deposition method, a sputtering method, a plasma method, etc. Alternatively to 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.).

[0139] Here, by forming a layer by a vacuum deposition method, a solution coating method, etc., crystallization is unlikely to occur, and the layer has excellent stability over time. When forming a film by a coating method, the film can be formed by combining with an appropriate binder resin.

[0140] 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.

[0141] 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.

[0142] [Protective layer] A protective layer may be provided on the cathode. For example, by bonding glass provided with a moisture absorbent on the cathode, the intrusion of water and the like into the organic compound layer can be reduced, and the occurrence of display defects can be reduced. In another embodiment, a passivation film such as silicon nitride may be provided on the cathode to reduce the intrusion of water and the like into the organic compound layer. For example, after forming the cathode, the cathode 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 form a protective layer. A protective layer may be provided using an atomic deposition method (ALD method) after the film is formed by the CVD method. The material of the film formed by the ALD method is not limited, and may be silicon nitride, silicon oxide, aluminum oxide, etc. Silicon nitride may be further formed by the CVD method on the film formed by the ALD method. The film formed by the ALD method may have a smaller thickness than the film formed by the CVD method. Specifically, the film formed by the ALD method may have a thickness of 50% or less, or even 10% or less, of the film formed by the CVD method.

[0143] [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.

[0144] [Planarization layer] A planarization layer may be provided between the color filter and the protective layer. The planarization layer is provided for the purpose of reducing unevenness of the layer below. It may also be called a material resin layer without limiting the purpose. The planarization layer may be composed of an organic compound, and may be either a low molecular weight or a high molecular weight, but is preferably a high molecular weight.

[0145] 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.

[0146] [Microlens] The organic light-emitting element according to this embodiment may have an optical member such as a microlens on the light emission side. The microlens may be made of acrylic resin, epoxy resin, or the like. The microlens may be intended to increase the amount of light extracted from the organic light-emitting element and control the direction of the extracted light. The microlens may have a hemispherical shape. When the microlens has a hemispherical shape, among the tangents to the hemisphere, there is a tangent that is parallel to the insulating layer, and the tangent and the hemisphere are the vertices of the microlens. The vertex of the microlens can be determined in the same manner in any cross-sectional view. That is, among the tangents to the semicircle of the microlens in the cross-sectional view, there is a tangent that is parallel to the insulating layer, and the tangent and the semicircle are the vertices of the microlens.

[0147] It is also possible to define the midpoint of the microlens. In the cross section of the microlens, a line segment is imaginary from the point where the shape of a circular arc starts to the point where the shape of another circular arc starts, and the midpoint of the line segment can be called the midpoint of the microlens. The cross section for determining the vertex and midpoint may be a cross section perpendicular to the insulating layer.

[0148] [Opposite substrate] A counter substrate may be provided on the planarization layer. The counter substrate is called a counter substrate because it is provided at a position corresponding to the aforementioned substrate. The constituent material of the counter substrate may be the same as that of the aforementioned substrate. When the aforementioned substrate is a first substrate, the counter substrate may be a second substrate.

[0149] [Pixel circuit] The light emitting device may have a pixel circuit connected to the light emitting element. The pixel circuit may be an active matrix type that controls the emission of the first light emitting element and the second light emitting element independently. The active matrix type circuit may be a voltage programming circuit or a current programming circuit. The drive circuit has a pixel circuit for each pixel. The pixel circuit may have a light emitting element, a transistor that controls the emission luminance of the light emitting element, a transistor that controls the emission timing, a capacitance that holds the gate voltage of the transistor that controls the emission luminance, and a transistor for connecting to GND without going through the light emitting element.

[0150] The light-emitting device has a display region and a peripheral region disposed around the display region. The display region has a pixel circuit, and the peripheral region has a display control circuit. The mobility of a transistor constituting the pixel circuit may be smaller than the mobility of a transistor constituting the display control circuit.

[0151] The slope of the current-voltage characteristic of the transistor that constitutes the pixel circuit may be smaller than the slope of the current-voltage characteristic of the transistor that constitutes the display control circuit. The slope of the current-voltage characteristic can be measured by the so-called Vg-Ig characteristic.

[0152] The transistor that constitutes the pixel circuit is a transistor that is connected to a light-emitting element, such as the first light-emitting element.

[0153] [Pixels] An organic light emitting device includes a plurality of pixels, each of which includes sub-pixels that emit different colors, for example, RGB colors.

[0154] The pixel emits light in an area called the pixel aperture. This area is the same as the first area. The pixel aperture may be 15 μm or less, or 5 μm or more. More specifically, it may be 11 μm, 9.5 μm, 7.4 μm, 6.4 μm, etc.

[0155] The distance between the subpixels may be 10 μm or less, and specifically, may be 8 μm, 7.4 μm, or 6.4 μm.

[0156] The pixels may have a known arrangement in plan view. For example, they may be a stripe arrangement, a delta arrangement, a pentile arrangement, or a Bayer arrangement. The shape of the subpixels in plan view may be any known shape. For example, they may be a rectangle, a quadrangle such as a diamond, or a hexagon. Of course, if the shape is not an exact figure but is close to a rectangle, it is included in the rectangle. The shape of the subpixels and the pixel arrangement may be used in combination.

[0157] (5) Uses of the organic light-emitting device according to this embodiment The organic light-emitting device according to the present embodiment 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.

[0158] 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.

[0159] 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.

[0160] Next, the display device according to the present embodiment will be described with reference to the drawings.

[0161] 1 is a schematic cross-sectional view showing an example of a display device having an organic light-emitting element and a transistor connected to the organic light-emitting element. The transistor is an example of an active element. The transistor may be a thin film transistor (TFT).

[0162] FIG. 1(a) shows an example of a pixel, which is a component of the display device according to this embodiment. The pixel has sub-pixels 10. The sub-pixels are divided into 10R, 10G, and 10B according to their light emission. The emitted light color may be distinguished by the wavelength emitted from the light-emitting layer, or the light emitted from the sub-pixel may be selectively transmitted or color-converted by a color filter or the like. Each sub-pixel has a reflective electrode 2, which is a first electrode, on an interlayer insulating layer 1, an insulating layer 3 covering the edge of the reflective electrode 2, an organic compound layer 4 covering the first electrode and the insulating layer, a transparent electrode 5, a protective layer 6, and a color filter 7.

[0163] A transistor and a capacitor may be disposed below or inside the interlayer insulating layer 1. The transistor and the first electrode may be electrically connected via a contact hole or the like (not shown).

[0164] The insulating layer 3 is also called a bank or a pixel separation film. It covers the edge of the first electrode and is disposed so as to surround the first electrode. The part where the insulating layer is not disposed contacts the organic compound layer 4 and becomes a light-emitting region.

[0165] The organic compound layer 4 has a hole injection layer 41 , a hole transport layer 42 , a first light emitting layer 43 , a second light emitting layer 44 , and an electron transport layer 45 .

[0166] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0167] The protective layer 6 reduces the penetration of moisture into the organic compound layer. Although the protective layer is illustrated as being a single layer, it may be a multi-layer. Each layer may be an inorganic compound layer and an organic compound layer.

[0168] The color filters 7 are divided into 7R, 7G, and 7B according to their colors. The color filters may be formed on a planarization film (not shown). A resin protective layer (not shown) may be provided on the color filters. The color filters may be formed on a protective layer 6. Alternatively, the color filters may be provided on an opposing substrate such as a glass substrate and then bonded to each other.

[0169] The display device 100 in FIG. 1(b) includes an organic light-emitting element 26 and a TFT 18 as an example of a transistor. A substrate 11 made of glass, silicon, or the like is provided with an insulating layer 12 on the substrate. An active element 18 such as a TFT is provided on the insulating layer, and a gate electrode 13, a gate insulating film 14, and a semiconductor layer 15 of the active element are provided. The active element 18 also includes a semiconductor layer 15, a drain electrode 16, and a source electrode 17. An insulating film 19 is provided on the active element 18. An anode 21 constituting the organic light-emitting element 26 and the source electrode 17 are connected via a contact hole 20 provided in the insulating film.

[0170] The electrical connection between the electrodes (anode, cathode) included in the organic light-emitting element 26 and the electrodes (source electrode, drain electrode) included in the TFT is not limited to the embodiment shown in Fig. 1(b). In other words, it is sufficient that either the anode or the cathode is electrically connected to either the TFT source electrode or the drain electrode. TFT stands for thin film transistor.

[0171] 1(b), the organic compound layer 22 is illustrated as a single layer, but may be a multi-layer organic compound layer 22. 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.

[0172] Although transistors are used as switching elements in the display device 100 of FIG. 1(b), other switching elements may be used instead.

[0173] The transistor used in the display device 100 of Fig. 1(b) is not limited to a transistor using a single crystal silicon wafer, but may be a thin film transistor 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.

[0174] The transistors included in the display device 100 of Fig. 1(b) 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.

[0175] The organic light-emitting element according to this embodiment has its light 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 respective light emission brightnesses. 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.

[0176] 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. The display panel 1005 may have an organic light-emitting element according to the present embodiment. The touch panel 1003 and the display panel 1005 are connected to flexible printed circuits FPC1002 and 1004, respectively. 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 even if the display device is a portable device.

[0177] 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.

[0178] The display device according to the present embodiment may be used as a display unit of 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 mobile phones such as smartphones, tablets, and head-mounted displays.

[0179] The display device according to the present embodiment may be used in a display unit of an imaging device having an imaging element that receives light. 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 may be a display unit disposed within a viewfinder. The imaging device may be a digital camera or a digital video camera.

[0180] 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 and the rear display 1102 may have an organic light-emitting element according to this embodiment. In this case, the viewfinder 1101 and the rear display 1102 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 a subject, the possibility that the subject will be blocked by an obstruction, and the like.

[0181] Since the timing suitable for capturing an image 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 according to this embodiment, because the organic light-emitting element has a fast response speed.

[0182] The imaging device 1100 may further include an optical section (not shown). The optical section may include a single lens or multiple lenses, which form an image on an imaging element housed in a housing 1104. The focus of the multiple lenses can be adjusted by adjusting their relative positions. This operation can also be performed automatically. The imaging device may be called a photoelectric conversion device. The photoelectric conversion device may include an imaging method that does not capture images sequentially, but detects the difference from the previous image, cuts out an image from an image that is always recorded, and the like.

[0183] FIG. 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 and performs unlocking or the like. An electronic device having a communication unit can also be called a communication device. The electronic device may further have a camera function by including a lens and an image sensor. An image captured by the camera function is displayed on the display unit. Examples of the electronic device include a smartphone and a notebook computer.

[0184] Fig. 4 is a schematic diagram showing an example of a display device according to this embodiment. Fig. 4(a) shows a display device such as a television monitor or a PC monitor. The display device 1300 has a housing 1301 and a display unit 1302. The organic light-emitting element according to this embodiment may be used in the display unit 1302.

[0185] The display device 1300 may have a housing 1301 and a base 1303 that supports a display unit 1302. The base 1303 is not limited to the form shown in Fig. 4(a). The bottom side of the housing 1301 may also serve as the base.

[0186] The housing 1301 and the display unit 1302 may be curved. The radius of curvature may be 5000 mm or more and 6000 mm or less.

[0187] 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 organic light-emitting element 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.

[0188] FIG. 5(a) is a schematic diagram showing an example of the lighting device according to the present embodiment. The lighting device 1400 may have a housing 1401, a light source 1402, and a circuit board 1403. The light source 1402 may have the organic light-emitting element according to the present embodiment. The lighting device 1400 may have an optical film 1404 to improve the color rendering of the light source. The lighting device 1400 may also have a light diffusion section 1405 to effectively diffuse the light of the light source. By having the light diffusion section 1405, the lighting device 1400 can deliver light to a wide range. The optical film 1404 and the light diffusion section 1405 may be provided on the light emission side of the lighting device. If necessary, a cover may be provided on the outermost part.

[0189] The lighting device is, for example, a device that illuminates a room. The lighting device may emit white light, neutral white light, or any other color from blue to red. The lighting device according to this embodiment may have a dimming circuit that dims these colors. The lighting device according to this embodiment may also have a power supply circuit that is connected to the organic light-emitting element according to this embodiment. The power supply circuit may be a circuit that converts AC voltage to DC voltage. Furthermore, white is a color temperature of 4200K, and neutral white is a color temperature of 5000K. The lighting device according to this embodiment may further have a color filter.

[0190] The lighting device according to this embodiment may also include a heat dissipation section that dissipates heat from within the device to the outside, and may be made of a material having a high thermal conductivity, such as metal or ceramic.

[0191] FIG. 5(b) is a schematic diagram of an automobile, which is an example of a moving body according to this embodiment. The automobile has a tail lamp, which is an example of a lamp. The automobile 1500 has a tail lamp 1501 and a vehicle body 1503, and may be in a form in which the tail lamp is turned on when the brakes are operated. The vehicle body 1503 may also be called a machine body. The automobile 1500 may have a window 1502 attached to the vehicle body 1503. The tail lamp 1501 may have an organic light-emitting element according to this embodiment. The tail lamp may have a protective member that protects the light source. 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. A furandicarboxylic acid derivative, an acrylonitrile derivative, or the like may be mixed into the polycarbonate.

[0192] The window 1502 may be a transparent display other than the window for checking the front and rear of the vehicle. The transparent display may have the 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 according to the present invention are made of transparent materials.

[0193] The moving body according to this embodiment includes one or both of a driving force generating unit that generates a driving force mainly used for moving the moving body, and a rotating body mainly used for moving the moving body. The driving force generating unit may be an engine, a motor, etc. The rotating body may be a tire, a wheel, a screw of a ship, a propeller of an aircraft, etc. Specifically, it may be a bicycle, a car, a train, a ship, an aircraft, a drone, etc. The moving body may have a body and a lamp provided on the body. The lamp may emit light so that the position of the body is known.

[0194] An application example of the display device of each of the above-mentioned embodiments will be described with reference to Fig. 6. The display device can be applied to a system that can be worn as a wearable device such as smart glasses, a head-mounted display, or a smart contact lens. A display device that can be used in a wearable device may have an imaging device capable of photoelectrically converting visible light, and a display device capable of emitting visible light.

[0195] FIG. 6 is a schematic diagram showing an example of glasses (smart glasses) according to this embodiment. Glasses 1600 (smart glasses) will be described with reference to FIG. 6(a). The glasses 1600 have a display unit on the rear side of a lens 1601. The display unit may have an organic light-emitting element according to the present invention. Furthermore, an imaging device 1602 such as a CMOS sensor or a SPAD may be provided on the front side of the lens 1601.

[0196] The glasses 1600 further include a control device 1603. The control device 1603 functions as a power source that supplies power to the image capture device 1602 and the display unit. The control device 1603 also controls the operations of the image capture device 1602 and the display unit. The lens 1601 is formed with an optical system for collecting light from the image capture device 1602 and the display unit.

[0197] The glasses 1610 (smart glasses) will be described with reference to FIG. 6(b). The glasses 1610 have a control device 1612, and the control device 1612 is provided with a display device having an organic light-emitting element according to the present invention. The control device 1612 may further have an imaging device corresponding to the imaging device 1602. An optical system for projecting light emitted from the control device 1612 is formed in the lens 1611, and an image is projected onto the lens 1611. The control device 1612 functions as a power source that supplies power to the imaging device and the display device, and controls the operation of the imaging device and the display device. The control device may have a line-of-sight detection unit that detects the line of sight of the wearer. Infrared light may be used for the detection of the line of sight. The infrared light emitting unit emits infrared light to the eyeball of a user gazing at a display image. Of the emitted infrared light, the imaging unit having a light receiving element detects the reflected light from the eyeball, thereby obtaining an image of the eyeball. By having a reduction means for reducing the light from the infrared light emitting unit to the display unit in a planar view, the deterioration of image quality is reduced.

[0198] The control device 1612 detects the user's line of sight with respect to the displayed image from the captured image of the eyeball obtained by capturing infrared light. Any known method can be applied to the line of sight detection using the captured image of the eyeball. As an example, a line of sight detection method can be used based on the Purkinje image formed by the reflection of irradiated light on the cornea.

[0199] More specifically, the gaze detection process is based on the pupil-corneal reflex method. Using the pupil-corneal reflex method, a gaze vector that represents the direction (rotation angle) of the eyeball is generated based on the pupil image and Purkinje image included in the captured image of the eyeball, thereby detecting the user's gaze.

[0200] The display device according to this embodiment may have an imaging device having a light receiving element, and may control the display image of the display device based on information about the user's line of sight from the imaging device.

[0201] Specifically, the display device determines a first field of view area to which the user gazes and a second field of view area other than the first field of view area based on the line-of-sight information. The first field of view area and the second field of view area may be determined by a control device of the display device, or may be received from an external control device. In the display area of ​​the display device, the display resolution of the first field of view area may be controlled to be higher than the display resolution of the second field of view area. In other words, the resolution of the second field of view area may be lower than that of the first field of view area.

[0202] The display area has a first field of view area and a second field of view area different from the first field of view area, and a high priority area is determined from the first field of view area and the second field of view area based on line-of-sight information. The first field of view area and the second field of view area may be determined by a control device of the display device, or may be determined by an external control device and received. The resolution of the high priority area may be controlled to be higher than the resolution of areas other than the high priority area. In other words, the resolution of an area with a relatively low priority may be lowered.

[0203] In addition, AI may be used to determine the first field of view area or the field of view area with high priority. The AI ​​may be a model configured to estimate the angle of the line of sight and the distance to the object at the end of the line of sight from the image of the eyeball, using the image of the eyeball and the direction in which the eyeball in the image was actually looking as teacher data. The AI ​​may be included in the display device, the imaging device, or an external device. When the external device has AI, it can be preferably applied to smart glasses further including an imaging device that captures images of the outside. The smart glasses can display captured external information in real time.

[0204] FIG. 7(a) is a schematic diagram showing an example of an image forming apparatus according to the present embodiment. The image forming apparatus 40 is an electrophotographic image forming apparatus, and includes a photoconductor 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transfer unit 32, a transport roller 33, and a fixing unit 35. Light 29 is irradiated from the exposure light source 28, and an electrostatic latent image is formed on the surface of the photoconductor 27. The exposure light source 28 may include an organic light-emitting element according to the present embodiment. The developing unit 31 includes a toner, etc. The charging unit 30 charges the photoconductor 27. The transfer unit 32 transfers the developed image to a storage medium 34. The transport roller 33 transports the recording medium 34. The recording medium 34 is, for example, paper. The fixing unit 35 fixes the image formed on the recording medium 34.

[0205] 7(b) and 7(c) are diagrams showing the exposure light source 28, and are schematic diagrams showing a state in which a plurality of light-emitting sections 36 are arranged on a long substrate. Arrow 37 indicates the column direction in which the organic light-emitting elements are arranged. This column direction is the same as the direction of the axis about which the photoconductor 27 rotates. This direction can also be called the long axis direction of the photoconductor 27. FIG. 7(b) shows a form in which the light-emitting sections 36 are arranged along the long axis direction of the photoconductor 27. FIG. 7(c) shows a form different from FIG. 7(b), in which the light-emitting sections 36 are alternately arranged in the column direction in each of the first column and the second column. The first column and the second column are arranged at different positions in the row direction. In the first column, a plurality of light-emitting sections 36 are arranged at intervals. In the second column, the light-emitting sections 36 are located at positions corresponding to the intervals between the light-emitting sections 36 in the first column. That is, a plurality of light-emitting sections 36 are also arranged at intervals in the row direction. The arrangement in FIG. 7(c) can also be described as a grid-like arrangement, a houndstooth arrangement, or a checkerboard pattern.

[0206] 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

[0207] The present invention will be described below with reference to examples, although the present invention is not limited thereto.

[0208] [Example 1 (Synthesis of Compound A-1)] Compound A-1 was synthesized according to the following synthetic route.

[0209] [ka]

[0210] Intermediate 1 (0.300 g), (3-cyanophenyl)boronic acid (0.225 g), Pd2(dba)3 (0.014 g), XPhos (0.015 g), sodium carbonate (0.240 g), toluene (45 mL), tetrahydrofuran (45 mL), and water (15 mL) were added and stirred at 80° C. for 16 hours. The mixture was extracted with toluene and purified using an organic solvent GPC column (JAIGEL-2H-40 manufactured by Japan Analytical Industry Co., Ltd., eluent: chloroform), to obtain 238 mg of compound A-1 as a yellow powder. The liquid obtained by adding THF to this yellow powder was subjected to mass spectrometry by UPLC (Ultra High Performance Liquid Chromatography)-MS and identified (m / z=830.435, C 60 H 54 N4).

[0211] [Example 2 (Synthesis of Compound A-2)] Compound A-2 was synthesized according to the following synthetic route.

[0212] [ka]

[0213] Intermediate 1 (0.400 g), (4-cyanophenyl)boronic acid (0.600 g), Pd(dppf)CH2Cl2 (0.033 g), sodium carbonate (0.323 g), toluene (100 mL), dioxane (100 mL), and water (30 mL) were added and stirred at 150 ° C for 16 hours. Extraction with toluene and purification with an organic solvent GPC column (JAIGEL-2H-40 manufactured by Japan Analytical Industry Co., Ltd., eluent: chloroform) were performed to obtain 288 mg of compound A-2 as a yellow powder. The liquid obtained by adding THF to this yellow powder was subjected to mass analysis by UPLC (Ultra High Performance Liquid Chromatography)-MS and identified (m / z = 830.435, C 60 H 54 N4).

[0214] [Example 3 (Fabrication and Evaluation of Organic Light-Emitting Device)] In Example 3, Compound A-1 was used as a guest material in the light-emitting layer. An organic light-emitting device having 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, and a cathode provided in this order on a substrate was produced by the method described below.

[0215] A glass substrate was used as a transparent conductive support substrate (ITO substrate) by forming a 100 nm thick ITO film as an anode on the glass substrate by sputtering. Next, the glass substrate with the ITO film was ultrasonically cleaned with acetone and isopropyl alcohol (IPA) in sequence, then boiled and cleaned with IPA, and then dried. Next, it was cleaned with UV / ozone. The glass substrate thus treated was used as a transparent conductive support substrate.

[0216] Next, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and a metal electrode layer are formed on the hole injection layer, -5 The electrodes were continuously formed by vacuum deposition using resistance heating in a vacuum chamber at 3 Pa. 2 The layer structure is shown below.

[0217] [Table 6]

[0218] Next, in order to prevent the organic light emitting device from deteriorating due to moisture absorption, the device was covered with a protective glass plate in a dry air atmosphere and sealed with an acrylic resin adhesive. In this manner, an organic light emitting device was obtained.

[0219] The characteristics of the obtained organic light-emitting device were measured and evaluated. 2 The external quantum efficiency (EQE) of the organic light-emitting device at this temperature was 4.46%.

[0220] Furthermore, the current density is 20mA / cm 2 A continuous driving test was performed at 100° C., and the time (LT80) at which the luminance degradation rate reached 20% from the initial luminance was measured. When the time at which the luminance degradation rate reached 20% in Comparative Example 1 was taken as 1.0, the relative value of LT80 in this example was 2.41.

[0221] The half-width of the emission spectrum was also determined to be 29 nm.

[0222] In this embodiment, the measuring device was a DC voltage / current source / monitor 6253 manufactured by ADC Corporation to measure the current-voltage characteristics, and a spectroradiometer SR-LEDW manufactured by Topcon Corporation to measure the luminance.

[0223] [Example 4, Comparative Example 1 (Fabrication and Evaluation of Organic Light-Emitting Device)] An organic light-emitting device was prepared in the same manner as in Example 3 except that compound A-1 was changed to compound A-2, and this was designated as Example 4. In addition, an organic light-emitting device was prepared in the same manner as in Example 3 except that compound A-1 was changed to compound Ref-1, and this was designated as Comparative Example 1. The characteristics of the prepared organic light-emitting device were measured and evaluated in the same manner as in Example 3. The results are shown in Table 7.

[0224] [Table 7]

[0225] From Table 7, the organic compound according to the present invention showed a superior element life compared to the comparative compound Ref-1. This is believed to be because the organic compound according to the present invention has an electron-withdrawing group, making the HOMO lower (farther from the vacuum level). In addition, the organic compound according to the present invention showed a smaller half-width than the comparative compound Ref-1.

[0226] From the above, the organic compound according to the present invention is an organic compound having excellent oxidation stability. Therefore, by using the organic compound according to the present invention in an organic light-emitting element, an organic light-emitting element having excellent element life can be provided. Furthermore, by using an organic compound having excellent oscillator strength among the organic compounds according to the present invention in an organic light-emitting element, an organic light-emitting element having excellent quantum yield (luminous efficiency) can be provided. Furthermore, by using an organic compound having excellent color purity among the organic compounds according to the present invention in an organic light-emitting element, an organic semiconductor that emits light having even more excellent color purity can be provided.

[0227] The present invention can also have the following configuration.

[0228] (Configuration 1) An organic compound represented by formula (1):

[0229] [ka]

[0230] In formula (1), rings A to C are each independently selected from the group consisting of substituted or unsubstituted aryl groups having from 6 to 50 carbon atoms and substituted or unsubstituted heterocyclic groups having from 3 to 50 carbon atoms. When rings A to C have a substituent, the substituent is a deuterium atom, an alkyl group, an aryl group, a heterocyclic group, a silyl group, an amino group, or a cyano group.

[0231] EWG is an electron-withdrawing group, an aryl group having at least one electron-withdrawing group, or a heterocyclic group having at least one or more electron-withdrawing groups.

[0232] n is an integer of 1 or greater.

[0233] (Configuration 2) In the formula (1), the electron-withdrawing group is a trifluoromethyl group, a trichloromethyl group, a nitro group, a cyano group, an aldehyde group, a ketone group, an ester group, a carboxylic acid group, a sulfonyl group, a sulfonic acid group, a pyridyl group, a triazinyl group, or a halogen atom.

[0234] (Configuration 3) 3. The organic compound according to claim 1, wherein in formula (1), the electron-withdrawing group is a trifluoromethyl group, a cyano group, or a fluorine atom.

[0235] (Configuration 4) In the formula (1), EWG is an aryl group having 6 to 20 carbon atoms and at least one electron-withdrawing group, or a heterocyclic group having 3 to 17 carbon atoms and at least one electron-withdrawing group.

[0236] (Configuration 5) 5. The organic compound according to any one of structures 1 to 4, wherein in formula (1), the aryl group possessed by the EWG is benzene.

[0237] (Configuration 6) In the formula (1), rings A to C are a substituted or unsubstituted aryl group having 6 to 20 carbon atoms and a substituted or unsubstituted heterocyclic group having 3 to 17 carbon atoms.

[0238] (Configuration 7) 7. The organic compound according to any one of structures 1 to 6, wherein in formula (1), ring A is a benzene skeleton or a naphthalene skeleton, and n is an integer of 1 or more and 4 or less.

[0239] (Configuration 8) 8. The organic compound according to any one of structures 1 to 7, wherein in formula (1), ring B is a benzene skeleton, a benzofuran skeleton, or a benzothiophene skeleton.

[0240] (Configuration 9) 9. The organic compound according to any one of structures 1 to 8, wherein in formula (1), ring C is a benzene skeleton, a benzofuran skeleton, or a benzothiophene skeleton.

[0241] (Configuration 10) An organic compound represented by formula (2) or (3):

[0242] [ka]

[0243] In formula (2), R 1 ~R 16 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, and a cyano group. 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 8 and R 9 , R 9 and R 10 , R 10 and R11 , R 12 and R 13 , R 13 and R 14 may be bonded to each other to form a ring. 15 and R 16 At least one of is an electron-withdrawing group, an aryl group having at least one electron-withdrawing group, or a heterocyclic group having at least one electron-withdrawing group.

[0244] In formula (3), R 21 ~R 38 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, and a cyano group. 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 26 and R 27 , R 28 and R 29 , R 29 and R 30 , R 30 and R 31 , R 32 and R 33 , R 33 and R 34 may be bonded to each other to form a ring. 35 ~R 38 At least one of is an electron-withdrawing group, an aryl group having at least one electron-withdrawing group, or a heterocyclic group having at least one electron-withdrawing group.

[0245] (Configuration 11) 11. The organic compound according to claim 10, wherein in formulas (2) and (3), the electron-withdrawing group is a trifluoromethyl group, a trichloromethyl group, a nitro group, a cyano group, an aldehyde group, a ketone group, an ester group, a carboxylic acid group, a sulfonyl group, a sulfonic acid group, a pyridyl group, a triazinyl group, or a halogen atom.

[0246] (Configuration 12) 12. The organic compound according to claim 10, wherein in the formulas (2) and (3), the electron-withdrawing group is a trifluoromethyl group, a cyano group, or a fluorine atom.

[0247] (Configuration 13) 13. An organic compound according to any one of structures 10 to 12, characterized in that in formulas (2) and (3), the ring is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 12 carbon atoms.

[0248] (Configuration 14) 14. The organic compound according to any one of structures 10 to 13, wherein in the formulas (2) and (3), the ring is a substituted or unsubstituted benzofuran skeleton, or a substituted or unsubstituted benzothiophene skeleton.

[0249] (Configuration 15) A first electrode and a second electrode, an organic compound layer disposed between the first electrode and the second electrode, The organic light-emitting device, wherein the organic compound layer comprises the organic compound according to any one of the first to fourteenth aspects.

[0250] (Configuration 16) the organic compound layer has a light-emitting layer, 16. The organic light-emitting device according to claim 15, wherein the light-emitting layer comprises the organic compound.

[0251] (Configuration 17) the light-emitting layer further comprises a first compound; 17. The organic light-emitting device according to claim 16, wherein the lowest excited singlet energy of the first compound is higher than the lowest excited singlet energy of the organic compound.

[0252] (Configuration 18) 18. The organic light-emitting device according to configuration 17, wherein the first compound is a hydrocarbon compound having a condensed polycyclic hydrocarbon group.

[0253] (Configuration 19) the light-emitting layer further comprises a second compound; The organic light-emitting element according to structure 17 or 18, characterized in that the lowest excited singlet energy of the second compound is higher than the lowest excited singlet energy of the organic compound and lower than the lowest excited singlet energy of the first compound.

[0254] (Configuration 20) 20. A display device comprising a plurality of pixels, at least one of which comprises an organic light-emitting element according to any one of structures 15 to 19 and a transistor connected to the organic light-emitting element.

[0255] (Configuration 21) An imaging element that receives light, and a display unit that displays an image captured by the imaging element, 20. A photoelectric conversion device, wherein the display section comprises the organic light-emitting element according to any one of configurations 15 to 19.

[0256] (Configuration 22) 20. An image display device comprising: a display section having the organic light-emitting element according to any one of configurations 15 to 19; and a housing in which the display section is provided.

[0257] (Configuration 23) 20. An electronic device comprising: a display unit having the organic light-emitting element according to any one of configurations 15 to 19; 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.

[0258] (Configuration 24) A wearable device comprising: a display unit having the organic light-emitting element according to any one of configurations 15 to 19; an optical system for concentrating light from the display unit; and a control device for controlling display of the display unit.

[0259] (Configuration 25) 20. A lighting device comprising: a light source having the organic light-emitting element according to any one of configurations 15 to 19; and a housing in which the light source is provided.

[0260] (Configuration 26) 20. A moving body comprising: a lighting fixture having the organic light-emitting element according to any one of configurations 15 to 19; and a body on which the lighting fixture is provided.

[0261] (Configuration 27) A photoconductor and an exposure light source for exposing the photoconductor, 20. An image forming apparatus, wherein the exposure light source has the organic light-emitting element according to any one of configurations 15 to 19. [Explanation of symbols]

[0262] 1 Interlayer insulation layer 2 reflective electrode 3. Insulation layer 4 Organic compound layer 5 Transparent electrode 6 Protective layer 7 Color Filters 10 subpixels 11 Substrate 12 Insulating layer 13 Gate electrode 14 Gate insulating film 15 Semiconductor layer 16 Drain electrode 17 Source electrode 18 Thin-film transistor 19 Insulating film 20 Contact Hole 21 Lower electrode 22 Organic compound layer 23 Upper electrode 24 First protective layer 25 Second protective layer 26 Organic light-emitting devices 27 Photoreceptor 28 Exposure light source 29 light 30 Charging section 31 Development section 32 Transcription section 33 Conveyor 34 Recording media 35 Fixing section 36 Light emitting part 37 A first direction parallel to the long axis of the photoconductor 40 Image forming device 100 display device 1000 display devices 1001 Top cover 1002 Flexible Printed Circuit 1003 Touch Panel 1004 Flexible Printed Circuit 1005 Display panel 1006 Frame 1007 Circuit Board 1008 Battery 1009 Lower cover 1100 Imaging device 1101 Viewfinder 1102 Rear display 1103 Operation section 1104 Case 1200 Electronic equipment 1201 Display section 1202 Operation unit 1203 Case 1300 display device 1301 Picture Frame 1302 Display section 1303 Foundation 1310 Display device 1311 First display section 1312 Second display section 1313 Case 1314 Bend Point 1400 Lighting Equipment 1401 Case 1402 Light source 1403 Circuit Board 1404 Optical film 1405 Light diffusion section 1500 Cars 1501 Tail lamp 1502 Window 1503 Body 1600 Smart Glasses 1601 Lens 1602 Imaging device 1603 Control device 1610 Smart Glasses 1611 Lens 1612 Control device

Claims

1. An organic compound represented by formula (1): 【Chemistry 1】 In formula (1), ring A to ring C are each independently selected from the group consisting of a substituted or unsubstituted aryl group having from 6 to 50 carbon atoms and a substituted or unsubstituted heterocyclic group having from 3 to 50 carbon atoms. When ring A to ring C have a substituent, the substituent is a deuterium atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, a heteroaryloxy group, a silyl group, an amino group, or a cyano group. EWG is an electron withdrawing group, an aryl group having at least one electron withdrawing group, or a heterocyclic group having at least one or more electron withdrawing groups. n is an integer of 1 or more.

2. The organic compound according to claim 1, characterized in that, in formula (1), the electron-withdrawing group is a trifluoromethyl group, a trichloromethyl group, a nitro group, a cyano group, an aldehyde group, a ketone group, an ester group, a carboxylic acid group, a sulfonyl group, a sulfonic acid group, a pyridyl group, a triazinyl group, or a halogen atom.

3. 2. The organic compound according to claim 1, wherein in formula (1), the electron-withdrawing group is a trifluoromethyl group, a cyano group, or a fluorine atom.

4. The organic compound according to claim 1, characterized in that, in formula (1), EWG is an aryl group having 6 to 20 carbon atoms and having at least one electron-withdrawing group, or a heterocyclic group having 3 to 17 carbon atoms and having at least one electron-withdrawing group.

5. 2. The organic compound according to claim 1, wherein, in formula (1), the aryl group possessed by EWG is benzene.

6. The organic compound according to claim 1, characterized in that, in formula (1), rings A to C are a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heterocyclic group having 3 to 17 carbon atoms.

7. 2. The organic compound according to claim 1, wherein in formula (1), ring A is a benzene skeleton or a naphthalene skeleton, and n is an integer of 1 or more and 4 or less.

8. 2. The organic compound according to claim 1, wherein in formula (1), ring B is a benzene skeleton, a benzofuran skeleton, or a benzothiophene skeleton.

9. 2. The organic compound according to claim 1, wherein, in formula (1), ring C is a benzene skeleton, a benzofuran skeleton, or a benzothiophene skeleton.

10. An organic compound represented by formula (2) or (3): 【Chemistry 2】 In formula (2), R １ ~R １６ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, and a cyano group. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ５ and R ６ , R ６ and R ７ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １２ and R １３ , R １３ and R １４ may be bonded to each other to form a ring. １５ and R １６ At least one of is an electron-withdrawing group, an aryl group having at least one electron-withdrawing group, or a heterocyclic group having at least one electron-withdrawing group. In formula (3), R ２１ ~R ３８ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, and a cyano group. ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２６ and R ２７ , R ２８ and R ２９ , R ２９ and R ３０ , R ３０ and R ３１ , R ３２ and R ３３ , R ３３ and R ３４ may be bonded to each other to form a ring. ３５ ~R ３８ At least one of is an electron-withdrawing group, an aryl group having at least one electron-withdrawing group, or a heterocyclic group having at least one electron-withdrawing group.

11. A first electrode and a second electrode; an organic compound layer disposed between the first electrode and the second electrode, The organic compound layer comprises the organic compound according to claim 1 .

12. the organic compound layer has a light-emitting layer, The organic light-emitting device according to claim 11 , wherein the light-emitting layer comprises the organic compound.

13. the light-emitting layer further comprises a first compound, The organic light-emitting element according to claim 12, wherein the lowest excited singlet energy of the first compound is higher than the lowest excited singlet energy of the organic compound.

14. The organic light-emitting device according to claim 13, wherein the first compound is a hydrocarbon compound having a condensed polycyclic hydrocarbon group.

15. the light-emitting layer further comprises a second compound; The organic light-emitting element according to claim 13, characterized in that the lowest excited singlet energy of the second compound is higher than the lowest excited singlet energy of the organic compound and lower than the lowest excited singlet energy of the first compound.

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

17. An imaging element that receives light, and a display unit that displays an image captured by the imaging element, The photoelectric conversion device, wherein the display section comprises the organic light-emitting element according to claim 11 .

18. 16. An image display device comprising: a display section having the organic light-emitting element according to claim 11; and a housing in which the display section is provided.

19. 16. An electronic device comprising: a display unit having the organic light-emitting element according to claim 11; 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.

20. 16. A wearable device comprising: a display unit having the organic light-emitting element according to claim 11; an optical system that collects light from the display unit; and a control device that controls display of the display unit.

21. A lighting device comprising: a light source having the organic light-emitting element according to claim 11; and a housing in which the light source is provided.

22. A moving body comprising: a lighting device having the organic light-emitting element according to claim 11; and a body on which the lighting device is provided.

23. A photoconductor and an exposure light source for exposing the photoconductor, 16. An image forming apparatus, comprising: an exposure light source comprising the organic light emitting element according to claim 11.

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