Organic compound and organic light-emitting device

Abstract

The organic compound is characterized by being represented by formula (1). In formula (1), rings A to C are each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 50 carbon atoms (inclusive) and a substituted or unsubstituted heterocyclic group having 3 to 50 carbon atoms (inclusive). 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.

Description

Technical Field

[0001] This invention relates to organic compounds and organic light-emitting devices containing such organic compounds. Background Technology

[0002] Organic light-emitting devices (hereinafter also referred to as "organic electroluminescent devices" or "organic EL devices") are electronic devices that each include a pair of electrodes and an organic compound layer disposed between these electrodes. Electrons and holes are injected from the electrode pair into the organic compound layer to generate excitons of the light-emitting organic compound in the organic compound layer, and the organic light-emitting device emits light when the excitons return to the ground state.

[0003] To date, active development has been undertaken of compounds suitable for organic light-emitting devices. Patent document 1 discloses compound Ref-1 as a compound having an indolocarbazole skeleton.

[0004] [Chemical Formula 1]

[0005]

[0006] Existing technical documents

[0007] Patent documents

[0008] Patent Document 1: International Publication No. WO 2019 / 111971 Summary of the Invention

[0009] The problem the invention aims to solve

[0010] However, the compounds specifically described in Patent Document 1 are those in which, when the central benzene in each indolocarbazole skeleton has a substituent, the substituent is an aryl or an aryl group having an alkyl group. Therefore, there is room for improvement in the oxidative stability of the above compounds.

[0011] In view of the above problems, the present invention has been made, and its object is to provide an organic compound with excellent oxidative stability.

[0012] Solution for solving the problem

[0013] The organic compounds according to the present invention are represented by formula (1).

[0014] [Chemical Formula 2]

[0015]

[0016] In formula (1), rings A to C are each independently selected from the group consisting of substituted or unsubstituted aryl groups having 6 or more but less than 50 carbon atoms and substituted or unsubstituted heterocyclic groups having 3 or more but less than 50 carbon atoms. When any of rings A to C has 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.

[0017] 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.

[0018] n is an integer greater than or equal to 1.

[0019] The effects of the invention

[0020] According to the present invention, organic compounds with excellent oxidative stability can be provided. Attached Figure Description

[0021] Figure 1A This is a schematic cross-sectional view illustrating an example of pixels in a display device according to an embodiment of the present invention.

[0022] Figure 1B This is a schematic cross-sectional view of an example of a display device including an organic EL device according to an embodiment of the present invention.

[0023] Figure 2 This is a schematic diagram of an example of a display device according to an embodiment of the present invention.

[0024] Figure 3A This is a schematic diagram of an example of a camera device according to an embodiment of the present invention.

[0025] Figure 3B This is a schematic diagram of an example of an electronic device according to an embodiment of the present invention.

[0026] Figure 4A This is a schematic diagram of an example of a display device according to an embodiment of the present invention.

[0027] Figure 4B This is a schematic diagram of an example of a foldable display device according to an embodiment of the present invention.

[0028] Figure 5A This is a schematic diagram of an example of a lighting device according to an embodiment of the present invention.

[0029] Figure 5B This is a schematic diagram of an example of a car including an automotive lighting unit according to an embodiment of the present invention.

[0030] Figure 6AThis is a schematic diagram illustrating an example of a wearable device according to an embodiment of the present invention.

[0031] Figure 6B This is a schematic diagram of an example of a wearable device according to an embodiment of the present invention, the wearable device including a camera device.

[0032] Figure 7A This is a schematic diagram of an example of an image forming apparatus according to an embodiment of the present invention.

[0033] Figure 7B This is a schematic diagram of an example of an exposure light source for an image forming apparatus according to an embodiment of the present invention.

[0034] Figure 7C This is a schematic diagram of an example of an exposure light source for an image forming apparatus according to an embodiment of the present invention.

[0035] Figure 8 This is a diagram illustrating the HOMO and LUMO orbital distributions of compounds A-1, A-2, Ref-4, and Ref-5. Detailed Implementation

[0036] In this specification, examples of halogen atoms include, but are not limited to, fluorine, chlorine, bromine, and iodine atoms.

[0037] Alkyl groups can have one or more but less than 20 carbon atoms, one or more but less than 10 carbon atoms, or one or more but less than 4 carbon atoms. Specific examples include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, octyl, cyclohexyl, tert-pentanyl, 3-methylpentan-3-yl, 1-adamantyl, and 2-adamantyl.

[0038] The aryl group can have 6 or more but less than 50 carbon atoms, 6 or more but less than 20 carbon atoms, 6 or more but less than 14 carbon atoms, or 6 or more but less than 12 carbon atoms. Specific examples include, but are not limited to, phenyl, naphthyl, indene, biphenyl, terphenyl, fluorenyl, phenanthrene, triphenylene, pyrene, anthracene, peryl, phenanthrene, and fluoranthracene.

[0039] Heterocyclic groups can have 3 or more but less than 50 carbon atoms, 3 or more but less than 20 carbon atoms, 3 or more but less than 17 carbon atoms, or 3 or more but less than 12 carbon atoms. Specific examples include, but are not limited to, pyridinyl, pyrazinyl, triazinyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, carbazoleyl, acridineyl, and phenanthrolinel.

[0040] The amino group can be a substituted amino group substituted with an alkyl or aryl group, and can be a substituted amino group substituted with an alkyl group having one or more but less than four carbon atoms or an aryl group having six or more but less than twelve carbon atoms. Specific examples include, but are not limited to, N-methylamino, N-ethylamino, N,N-dimethylamino, N,N-diethylamino, N-methyl-N-ethylamino, N-benzylamino, N-methyl-N-benzylamino, N,N-dibenzylamino, aniline, N,N-diphenylamino, N,N-dinaphthylamino, N,N-difluorenylamino, N-phenyl-N-tolylamino, N,N-xylylamino, N-methyl-N-phenylamino, N,N-dianisoleylamino, N-methyl-N-phenylamino, N,N-tris(triphenylamino), N-phenyl-N-(4-tert-butylphenyl)amino, N-phenyl-N-(4-trifluoromethylphenyl)amino, and N-piperidinyl.

[0041] Alkoxy groups can have one or more but fewer than 10 carbon atoms, or one or more but fewer than 4 carbon atoms. Specific examples include, but are not limited to, methoxy, ethoxy, propoxy, 2-ethyl-octoxy, and benzyloxy.

[0042] Specific examples of aryloxy groups are phenoxy groups, but not limited to them.

[0043] Specific examples of heteroaryloxy groups are thiophenoxy groups, but not limited to them.

[0044] Specific examples of silanes include, but are not limited to, trimethylsilane and triphenylsilane.

[0045] Examples of substituents that may be further included in alkyl, alkoxy, amino, aryloxy, silyl, aryl, and heterocyclic groups include, but are not limited to, halogen atoms such as fluorine, chlorine, bromine, and iodine; alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl; alkoxy such as methoxy, ethoxy, and propoxy; amino such as dimethylamino, diethylamino, dibenzylamino, diphenylamino, and xylylamino; aryloxy such as phenoxy; aryl such as phenyl and biphenyl; heterocyclic groups such as pyridyl and pyrroleyl; and cyano.

[0046] (1) Organic compounds

[0047] First, the organic compounds according to the present invention will be described.

[0048] The organic compounds according to the present invention are organic compounds represented by formula (1).

[0049] [Chemical Formula 3]

[0050]

[0051] In formula (1), rings A to C are each independently selected from the group consisting of substituted or unsubstituted aryl groups having 6 or more but less than 50 carbon atoms and substituted or unsubstituted heterocyclic groups having 3 or more but less than 50 carbon atoms.

[0052] When any of the rings A to C has 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.

[0053] When any of rings A to C has a substituent, the substituent can be an alkyl, aryl, amino, or heterocyclic group, and preferably an alkyl, aryl, or heterocyclic group. Specifically, the substituent can be an alkyl group having one or more but four or fewer carbon atoms, an aryl group having six or more but fourteen or fewer carbon atoms, or a heterocyclic group having three or more but twelve or fewer carbon atoms. More specifically, the substituent can be methyl, isopropyl, tert-butyl, phenyl, phenyl having a tert-butyl group, phenyl having a methyl group, or dibenzofuranyl. The amino group can be diphenylamino, and any phenyl group in diphenylamino can include an alkyl group having one or more but four or fewer carbon atoms. The alkyl group can specifically be isopropyl or tert-butyl.

[0054] Each of rings A to C can be a substituted or unsubstituted aryl group having 6 or more but less than 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 3 or more but less than 17 carbon atoms.

[0055] Specifically, ring A can be a benzene skeleton, a naphthalene skeleton, or a fluorene skeleton, and can be either a benzene skeleton or a naphthalene skeleton. Each ring B can be a benzene skeleton, a benzofuran skeleton, or a benzothiophene skeleton, and can be either a benzene skeleton or a benzofuran skeleton. Each ring C can be a benzene skeleton, a benzofuran skeleton, or a benzothiophene skeleton, and can be either a benzene skeleton or a benzofuran skeleton.

[0056] 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. EWG can be an aryl group having at least one electron-withdrawing group and having 6 or more but less than 20 carbon atoms, or a heterocyclic group having at least one or more electron-withdrawing groups and having 3 or more but less than 17 carbon atoms.

[0057] Here, the electron-withdrawing group is trifluoromethyl, trichloromethyl, nitro, cyano, aldehyde, ketone, ester, carboxylic acid, sulfonyl, sulfonic acid, pyridyl, triazine, or a halogen atom, etc. Preferably, the Hammett substituent constant of the electron-withdrawing group is 0.01 or more and 0.70 or less. More specifically, the electron-withdrawing group is preferably trifluoromethyl, cyano, or a fluorine atom.

[0058] A bipyridyl group is defined as a structure in which the pyridyl group, as a heterocyclic group, has another pyridyl group that acts as an electron-withdrawing group. Similarly, a benzyl nitrile group is defined as a structure in which the phenyl group, as an aryl group, has a cyano group that acts as an electron-withdrawing group.

[0059] n is an integer greater than or equal to 1. The possible values ​​of n are defined by the structure of ring A. For example, when ring A has a benzene skeleton, n is 1 or 2. When ring B has a naphthalene skeleton, n is an integer greater than or equal to 1 and less than or equal to 4.

[0060] Formula (1) can be represented by the following formula (2) or (3). Formula (2) is a compound in which ring A in formula (1) has a benzene skeleton. Formula (3) is a compound in which ring A in formula (1) has a naphthalene skeleton.

[0061] [Chemical Formula 4]

[0062]

[0063] In equation (2), R 1 To R 16 Each is independently selected from the group consisting of hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted silyl group, substituted or unsubstituted amino group, and 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 、or R 13 and R 14 They can form a ring together. R is preferred. 3 and R 4 Together they form a ring, and R 10 and R 11 Together they form a ring. R is preferred. 5 and R 6 Together they form a ring, and R 12 and R 13Together, they form a ring. Each ring thus formed can be a substituted or unsubstituted aryl group having 6 or more but less than 12 carbon atoms, or a substituted or unsubstituted heterocyclic group having 3 or more but less than 12 carbon atoms. Specifically, each ring thus formed can be a substituted or unsubstituted benzofuran skeleton or a substituted or unsubstituted benzothiophene skeleton. The condition is R. 15 and R 16 At least one of them is an electron-withdrawing group, an aryl group having at least one or more electron-withdrawing groups, or a heterocyclic group having at least one or more electron-withdrawing groups.

[0064] In formula (2), when the organic compound according to the invention has substituents, R 3 R 4 R 5 R 6 R 10 R 11 R 12 and R 13 Any of the elements in R can have substituents. 3 R 6 R 10 and R 13 Or R 3 and R 10 R 4 and R 11 and R 5 and R 12 Any pair in the middle can have substituents.

[0065] In equation (3), R 21 To R 38 Each is independently selected from the group consisting of hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted silyl group, substituted or unsubstituted amino group, and 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 、or R33 and R 34 They can form a ring together. R is preferred. 23 and R 24 Together they form a ring, and R 30 and R 31 Together they form a ring. R is preferred. 25 and R 26 Together they form a ring, and R 32 and R 33 Together, they form a ring. Each ring thus formed can be a substituted or unsubstituted aryl group having 6 or more but less than 12 carbon atoms, or a substituted or unsubstituted heterocyclic group having 3 or more but less than 12 carbon atoms. Specifically, each ring thus formed can be a substituted or unsubstituted benzofuran skeleton or a substituted or unsubstituted benzothiophene skeleton. The condition is R. 35 To R 38 At least one of them is an electron-withdrawing group, an aryl group having at least one or more electron-withdrawing groups, or a heterocyclic group having at least one or more electron-withdrawing groups.

[0066] In formula (3), when the organic compound according to the invention has substituents, R 23 R 24 R 25 R 26 R 30 R 31 R 32 and R 33 Any of the elements in R can have substituents. 23 R 26 R 30 and R 33 Or R 23 and R 30 R 24 and R 31 and R 25 and R 32 Any pair in can have substituents.

[0067] The properties of the organic compounds according to the present invention will now be described.

[0068] In the organic compounds according to the invention, 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, resulting in a low highest occupied molecular orbital (HOMO) (farther from the vacuum level). Therefore, the organic compounds according to the invention exhibit excellent oxidative stability.

[0069] 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, a molecular orbital calculation software developed by Gaussian, Inc. (Gaussian 16, Revision C.01, MJ Frisch et al., Gaussian, Inc., Wallingford, CT, 2019). The keywords used are B3LYP / 6-31G*. The results are shown in Table 1.

[0070] [Table 1]

[0071]

[0072] As can be seen from Table 1, the HOMO values ​​of compounds A-1 and A-2, which are examples of organic compounds according to the present invention, are -5.25 eV and -5.29 eV, respectively, while the HOMO value of compound Ref-1, which is a comparative compound, is -5.11 eV. This is considered to be because the organic compounds according to the present invention have electron-withdrawing groups. Therefore, compared with the HOMO value of compound Ref-1, the organic compounds according to the present invention are organic compounds with excellent oxidative stability.

[0073] The organic compounds according to the invention have at least one of an electron-withdrawing group, an aryl group having an electron-withdrawing group, and a heterocyclic group having an electron-withdrawing group, and thus can achieve the effects according to the invention. The HOMO values ​​of compounds A-2, A-3, A-4, and A-5, which are examples of organic compounds according to the invention, and compounds Ref-2 and Ref-3, which are comparative compounds, were determined using the above-described calculation method. The results are shown in Table 2.

[0074] [Table 2]

[0075]

[0076] As can be seen from Table 2, the organic compounds according to the present invention exhibit lower HOMO values ​​than comparative compounds Ref-2 and Ref-3. The organic compounds according to the present invention have 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, thus achieving the effects according to the present invention.

[0077] In the organic compounds according to the present invention, 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; therefore, the full width at half maximum (FWHM) of the emission spectrum should exhibit a small value.

[0078] Patent document 1 describes the following compounds Ref-4 and Ref-5. These are compounds in which each ring B in formula (1) includes an aryl group having an electron-withdrawing group.

[0079] [Chemical Formula 5]

[0080]

[0081] The organic compound according to the present invention differs from compounds Ref-4 and Ref-5 in that 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. Therefore, the organic compound according to the present invention is expected to exhibit superior color purity compared to compounds Ref-4 and Ref-5.

[0082] Using Gaussian 16, a molecular orbital calculation software manufactured by Gaussian, Inc. (Gaussian 16, Revision C.01, MJ Frisch et al., Gaussian, Inc., Wallingford, CT, 2019), the HOMO and LUMO orbital distributions of compounds A-1 and A-2, which are examples of organic compounds according to the present invention, and the HOMO and LUMO orbital distributions of compounds Ref-4 and Ref-5, which are comparative compounds, were visualized. In this calculation, the isosurface value (electron density isosurface) was set to 0.02. The results are shown in... Figure 8 middle.

[0083] like Figure 8 As shown, the HOMO and LUMO orbital distributions of compounds A-1 and A-2, which are examples of organic compounds according to the present invention, are respectively located in the middle of the structure represented by formula (1). In contrast, differences were observed between the HOMO and LUMO orbital distributions of compounds Ref-4 and Ref-5 respectively (by... Figure 8 (Outlined by the black dashed circle). In other words, compared with the organic compounds according to the present invention, the overlap between the HOMO orbital distributions and LUMO orbital distributions of compounds Ref-4 and Ref-5 is small.

[0084] Generally, when the overlap between the HOMO and LUMO orbital distributions is small, structural relaxation between the excited and ground states increases, thus the emission spectrum tends to broaden. On the other hand, when the overlap between the HOMO and LUMO orbital distributions is large, structural relaxation between the excited and ground states can be suppressed, thus the emission spectrum tends to be sharper.

[0085] Therefore, compared to comparative compounds Ref-4 and Ref-5, the organic compounds according to the present invention are expected to exhibit sharp emission spectra. In other words, the organic compounds according to the present invention are expected to exhibit excellent color purity.

[0086] A more preferred embodiment of the organic compound according to the present invention will now be described.

[0087] In the organic compounds according to the invention, in formula (1), the EWG is preferably an aryl group having at least one electron-withdrawing group. The oscillator intensities of compounds A-1, A-4, and A-6, which are examples of organic compounds according to this embodiment, were calculated using Gaussian 16, a molecular orbital calculation software developed by Gaussian, Inc. (Gaussian16, Revision C.01, MJ Frisch et al., Gaussian, Inc., Wallingford, CT, 2019). The keywords used are B3LYP / 6-31G*. The results are shown in Table 3.

[0088] [Table 3]

[0089]

[0090] As can be seen from Table 3, the oscillator strength of compound A-1 is higher than that of compounds A-4 and A-6.

[0091] Here, the relationship between oscillator strength and quantum yield (luminescence efficiency) is described. As described in paragraph

[0262] of Japanese Patent Application Publication No. 2020-47930 and paragraph

[0035] of Japanese Patent Application Publication No. 2022-46999, compounds with high oscillator strength are known to exhibit high quantum yield (luminescence efficiency).

[0092] Therefore, in the organic compound according to the invention, from the viewpoint of quantum yield (luminescence efficiency), the EWG in formula (1) is preferably an aryl group having at least one electron-withdrawing group.

[0093] In the organic compounds according to the invention, when the EWG in formula (1) is an aryl group having at least one electron-withdrawing group, the aryl group preferably has a benzene skeleton. This is because the oscillator strength exhibits a higher value compared to the case where the aryl group having at least one electron-withdrawing group has a naphthalene skeleton. The oscillator strengths of compounds A-1 and A-7, which are examples of organic compounds according to this embodiment, were determined using the same calculation method as in Table 3. The results are shown in Table 4.

[0094] [Table 4]

[0095]

[0096] Table 4 shows that compound A-1 exhibits a higher oscillator strength than compound A-7. As mentioned above, high oscillator strength is known to lead to high quantum yield (luminescence efficiency). Therefore, from the viewpoint of quantum yield (luminescence efficiency), an aryl group having at least one electron-withdrawing group is preferably a benzene skeleton.

[0097] In the organic compounds according to the invention, when the EWG in formula (1) is an aryl group having at least one electron-withdrawing group and the aryl group is a benzene skeleton, the electron-withdrawing group is preferably bonded to the meta or para position relative to ring A. This is because, in this case, the organic compounds according to this embodiment exhibit higher oscillator strength. The oscillator strengths of compounds A-1, A-2, and A-8, which are examples of organic compounds according to this embodiment, were determined using the same calculation method as in Table 3. The results are shown in Table 5.

[0098] [Table 5]

[0099]

[0100] Table 5 shows that compounds A-1 and A-2 exhibit higher oscillator strength than compound A-8. As mentioned above, high oscillator strength is known to lead to high quantum yield (luminescence efficiency). Therefore, from the viewpoint of quantum yield (luminescence efficiency), when the EWG in formula (1) is an aryl group having at least one electron-withdrawing group and the aryl group is a benzene skeleton, the electron-withdrawing group is preferably bonded to the meta or para position relative to ring A.

[0101] In the organic compounds according to the invention, the electron-withdrawing groups are preferably trifluoromethyl, cyano, or fluorine atoms. This is because these electron-withdrawing groups have moderately strong electron-withdrawing properties, resulting in greater overlap between the HOMO and LUMO orbital distributions. As a result, the organic compounds according to this embodiment are expected to exhibit smaller full width at half maximum (FWHM). In other words, the organic compounds according to this embodiment are expected to be organic compounds with excellent color purity.

[0102] Specific examples of organic compounds according to the present invention are described below. However, the invention is not limited thereto.

[0103] [Chemical Formula 6]

[0104]

[0105] [Chemical Formula 7]

[0106]

[0107] [Chemical Formula 8]

[0108]

[0109] [Chemical Formula 9]

[0110]

[0111] [Chemical Formula 10]

[0112]

[0113] [Chemical Formula 11]

[0114]

[0115] [Chemical Formula 12]

[0116]

[0117] [Chemical Formula 13]

[0118]

[0119] [Chemical Formula 14]

[0120]

[0121] [Chemical Formula 15]

[0122]

[0123] [Chemical Formula 16]

[0124]

[0125] [Chemical Formula 17]

[0126]

[0127] [Chemical Formula 18]

[0128]

[0129] [Chemical Formula 19]

[0130]

[0131] [Chemical Formula 20]

[0132]

[0133] [Chemical Formula 21]

[0134]

[0135] [Chemical Formula 22]

[0136]

[0137] [Chemical Formula 23]

[0138]

[0139] [Chemical Formula 24]

[0140]

[0141] [Chemical Formula 25]

[0142]

[0143] [Chemical Formula 26]

[0144]

[0145] [Chemical Formula 27]

[0146]

[0147] [Chemical Formula 28]

[0148]

[0149] [Chemical Formula 29]

[0150]

[0151] [Chemical Formula 30]

[0152]

[0153] (2) Organic light-emitting devices

[0154] An organic light-emitting device according to an embodiment of the present invention will now be described. The organic light-emitting device according to an embodiment of the present invention includes 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 of this embodiment, the organic compound layer may be formed from a single layer or a multilayer stack comprising multiple layers, as long as it contains a light-emitting layer. The organic compound according to the present invention may be contained in the organic compound layer, and preferably in the light-emitting layer. When the organic compound layer is formed from a multilayer stack comprising multiple layers, in addition to the light-emitting layer, the organic compound layer may also include a hole (positive hole) injection layer, a hole transport layer, an electron blocking layer, a hole / exciton blocking layer, an electron transport layer, and an electron injection layer, etc. The light-emitting layer may be formed from a single layer or a multilayer stack comprising multiple layers. In the case of providing multiple light-emitting layers, a charge-generating layer may be disposed between the light-emitting layers. The charge-generating layer may be made of a compound having a LUMO energy level lower than the lowest unoccupied molecular orbital (LUMO) 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 and LUMO energy levels of the organic compound layer can be the HOMO and LUMO energy levels of the organic compound with the largest weight ratio in the organic compound layer.

[0155] Here, the HOMO and LUMO levels are described as being "higher" the closer they are to the vacuum level. The fact that the LUMO level of the charge generation layer is lower than the HOMO level of the hole transport layer indicates that the LUMO level of the charge generation layer is further away from the vacuum level than the HOMO level of the hole transport layer.

[0156] In this specification, the HOMO and LUMO energy levels can be calculated using molecular orbital calculations. Molecular orbital calculations can be performed using density functional theory (DFT) with, for example, B3LYP functionals and 6-31G* basis sets. Molecular orbital calculations can be performed, for example, using Gaussian 09 (Gaussian 09, Revision C.01, MJ Frisch, GW Trucks, HB Schlegel, GE Scuseria, MA Robb, JR Cheeseman, G.Scalmani, V. Barone, B. Mennucci, GA Petersson, H. Nakatsuji, M. Caricato, X.Li, HP Hratchian, AF Izmaylov, J. Bloino, G. Zheng, JL Sonnenberg, M.Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y.Honda, O. Kitao, H. Nakai, T. Vreven, JA Montgomery, Jr., JE Peralta, F.Ogliaro, M. Bearpark, JJ Heyd, E. Brothers, KN ​​Kudin, VN Staroverov, T.Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, JC Burant, SS Iyengar, J. Tomasi, M. Cossi, N. Rega, JM Millam, M. Klene, JE Knox, JB Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, RE Stratmann, O.Yazyev, AJ Austin, R. Cammi, C. Pomelli, JW Ochterski, RL Martin, K.Morokuma, VG Zakrzewski, GA Voth, P. Salvador, JJ(Dannenberg, S. Dapprich, AD Daniels, O. Farkas, JB Foresman, JV Ortiz, J. Cioslowski, and DJ Fox, Gaussian, Inc., Wallingford CT, 2010)

[0157] In this specification, HOMO and LUMO energy levels can be calculated using ionization potential and band gap. HOMO energy levels can be estimated by measuring the ionization potential. The ionization potential can be measured using a measuring device such as an AC-3 after dissolving the compound to be measured in a solvent such as toluene, or after forming a vapor-deposited film of the compound to be measured on a substrate such as glass. The band gap can be measured by dissolving the compound to be measured in a solvent such as toluene and performing a measurement thereunder with excitation light. The band gap can be determined by measuring the absorption edge in the absorption spectrum of the excitation light. Alternatively, the measurement can be performed by vapor-depositing the compound to be measured on a substrate such as glass and irradiating the vapor-deposited film with excitation light. In this measurement, the band gap is determined by measuring the absorption edge in the absorption spectrum obtained when the vapor-deposited film absorbs the excitation light.

[0158] The LUMO level can be calculated using the band gap and ionization potential values. The LUMO level can be estimated by subtracting the ionization potential from the band gap.

[0159] The LUMO level can also be estimated from the reduction potential. For example, the single-electron reduction potential can be estimated using cyclic voltammetry (CV) measurements. CV measurements can be performed, for example, in a 0.1 M tetrabutylammonium perchlorate solution in DMF using an Ag / Ag electrode as a reference electrode. + The LUMO level is determined by using Pt as the counter electrode and glassy carbon as the working electrode. The LUMO level can be estimated by adding -4.8 eV to the difference between the reduction potential of ferrocene and the reduction potential of the obtained compound.

[0160] In an organic light-emitting device according to an embodiment of the present invention, when the organic compound according to the present invention is included in the light-emitting layer, the light-emitting layer may be a layer made solely of the organic compound according to the present invention, or it may be a layer made of the organic compound according to the present invention and another compound. Here, when the light-emitting layer is a layer made of the organic compound according to the present invention and another compound, the organic compound according to the present invention may be used as a host material in the light-emitting layer, as a guest material, or as an auxiliary material that may be included in the light-emitting layer. Here, the host material is also referred to as the "host" or "first compound," and is the compound having the largest mass ratio among the compounds constituting the light-emitting layer. The guest material is also referred to as the "guest," "dopant material," "dopant," or "third compound." The guest material is a compound having a smaller mass ratio than the host material among the compounds constituting the light-emitting layer, and is the compound that mainly contributes to light emission. Therefore, the guest material is sometimes also referred to as the light-emitting material. The auxiliary material is also referred to as the "auxiliary" or "second compound." The auxiliary material is a compound having a smaller mass ratio than the host material among the compounds constituting the light-emitting layer and contributing to the light emission of the guest material. The auxiliary material is also referred to as the second host.

[0161] Here, the lowest excitation singlet state energy of the host material is denoted as S1(H), the lowest excitation singlet state energy of the guest material is denoted as S1(D), and the lowest excitation singlet state energy of the auxiliary material is denoted as S1(A). The guest material can be considered as an organic compound according to the present invention. In this case, the organic light-emitting device according to this embodiment preferably satisfies S1(H)>S1(D) or S1(H)>S1(A)>S1(D). When the lowest excitation singlet state energy of the compound contained in the organic light-emitting device according to this embodiment satisfies the above relationship, excitons can be effectively transferred to the guest material, thereby providing an organic light-emitting device with high luminous efficiency.

[0162] When the organic compound according to the invention is used as the guest material in the light-emitting layer, the concentration of the guest material relative to the whole light-emitting layer can be more than 0.01% by mass and less than 50% by mass, and preferably more than 0.01% by mass and less than 10% by mass, more preferably more than 0.01% by mass and less than 5% by mass.

[0163] When the light-emitting layer further includes auxiliary materials, the auxiliary materials can be 1% or more and less than 50% by mass relative to the total light-emitting layer, and preferably 10% or more and less than 50% by mass. The object can be 0.01% or more and less than 20% by mass, and preferably 0.01% or more and less than 5% by mass.

[0164] The inventors have conducted various studies and discovered that when the organic compound according to the invention is used as a host or guest material in the light-emitting layer, and particularly when used as a guest material in the light-emitting layer, a device exhibiting high efficiency, high brightness, and extremely high durability of light output can be obtained. The light-emitting layer can be a single layer or can include multiple light-emitting layers, and can also be mixed with the blue light emission color of this embodiment by including another light-emitting material, emitting light of a different color from that other light-emitting material. The term "multiple light-emitting layers" refers to a state in which one light-emitting layer and another light-emitting layer are stacked. In this case, the light emission color of the organic light-emitting device is not limited to blue. More specifically, the light emission color can be white or an intermediate color. In the case of white, the other light-emitting layer emits a color other than blue, i.e., red or green. Furthermore, the film can be formed by film-forming methods such as vapor deposition or coating. Details will be described in detail in the embodiments described later.

[0165] The organic compounds according to the present invention can be used as constituent materials of organic compound layers other than the light-emitting layer constituting the organic light-emitting device of this embodiment. Specifically, the organic compounds can be used as constituent materials of electron transport layers, electron injection layers, hole transport layers, hole injection layers, or hole blocking layers, etc. In this case, the emission color of the organic light-emitting device is not limited to blue. More specifically, the emission color can be white emission or intermediate colors.

[0166] (3) Other compounds

[0167] Here, in addition to the organic compounds according to the invention, conventionally known low and high molecular weight hole injection or hole transport compounds, host materials, luminescent compounds, electron injection or electron transport compounds, etc., may be used together as needed. Examples of these compounds are described below.

[0168] As hole injection / transport materials, materials that promote hole injection from the anode and have high hole mobility, enabling the injected holes to be transported to the light-emitting layer, are preferred. Materials with high glass transition temperatures are preferred to suppress crystallization of organic compounds in organic light-emitting devices. Examples of low-molecular-weight and high-molecular-weight materials with hole injection / transport capabilities include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. The aforementioned hole injection / transport materials are also suitably used in electron blocking layers. When forming a hole injection layer by coating, a mixture of poly(ethylenedioxythiophene) and poly(styrene sulfonate) (PEDOT: PSS), commonly used as hole injection materials, can be used. Specific examples of compounds used as hole injection / transport materials are described below, but of course, the compounds are not limited thereto.

[0169] [Chemical Formula 31]

[0170]

[0171] Among the hole injection / transport materials described above, HT16 to HT18 can reduce the driving voltage when used in the layer in contact with the anode. HT16 is widely used in organic light-emitting devices. HT2 to HT7, HT10, HT12, and HT22 to HT28 can be used in organic compound layers adjacent to HT16. Hole-transporting polymers such as poly(phenylenevinylene) (PPV), polyfluorene (PF), polyvinylcarbazole (PVK), and their derivatives can also be used. Furthermore, inorganic insulating layers made of, for example, SiO2 or SiN, or organosilicon polymers (e.g., siloxanes) can also be used. Additionally, multiple materials can be used in a single organic compound layer.

[0172] Examples of luminescent materials primarily involved in luminescence include donor-acceptor type organic compounds, boron-containing complexes, indole-carbazole fused-ring compounds and fused-ring compounds (e.g., fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetraphenylene derivatives, anthracene derivatives, and rubrene), quinacridone derivatives, coumarin derivatives, stilbene derivatives, organoaluminum complexes (e.g., tris(8-quinolino)aluminum), iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, and polymer derivatives, such as poly(phenylenevinylene) derivatives, poly(fluorene) derivatives, and poly(phenylene) derivatives. Furthermore, when forming the luminescent layer by coating, high molecular weight compounds with luminescent properties are primarily used. This is because, compared to low molecular weight compounds, high molecular weight compounds are highly amorphous and less likely to crystallize. Specific examples of materials used include high molecular weight compounds such as poly(phenylenevinylene) (PPV), polyfluorene (PF), polyvinylcarbazole (PVK), and their derivatives.

[0173] The following describes specific examples of compounds that can be used as luminescent materials, but of course, the compounds are not limited thereto.

[0174] [Chemical Formula 32]

[0175]

[0176] [Chemical Formula 33]

[0177]

[0178] The following describes specific examples of compounds used as the host in the luminescent layer or as emission-assisted dopant contained in the luminescent layer, but of course, the compounds are not limited thereto.

[0179] [Chemical Formula 34]

[0180]

[0181] In EM1 to EM47, the host material can be a hydrocarbon compound having fused polycyclic hydrocarbon groups. Specific examples include EM1 to EM26, EM46, and EM47.

[0182] As an electron transport material, any material capable of transporting electrons injected from the cathode to the light-emitting layer can be selected, taking into account factors such as the balance with the hole mobility of the hole transport material. Examples of materials capable of transporting electrons include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organoaluminum complexes, and fused-ring compounds (e.g., fluorene derivatives, naphthalene derivatives, thionyl derivatives, and anthracene derivatives). These electron transport materials are also suitable for hole blocking layers.

[0183] The following section provides specific examples of compounds used as electron transport materials, but of course, the compounds are not limited to these.

[0184] [Chemical Formula 35]

[0185]

[0186] Electron-injection materials can be freely selected from materials into which electrons can be easily injected from the cathode, taking into account, for example, a balance with hole injection properties. As organic compounds, n-type dopants and reducing dopants are also included. Examples include alkali metal-containing compounds, such as lithium fluoride, lithium complexes such as lithium quinolinate, benzimidazole derivatives, imidazole derivatives, fullerene derivatives, and acridine derivatives.

[0187] It can also be used in combination with the aforementioned electronic transmission materials.

[0188] (4) Structure of organic light-emitting devices

[0189] The components constituting the organic light-emitting device of this embodiment will be described below.

[0190] An organic light-emitting device includes an insulating layer, a first electrode, an organic compound layer, and a second electrode located above a substrate. A protective layer, a color filter, a microlens, etc., can be disposed above the second electrode. When a color filter is provided, a planarization layer can be disposed between the color filter and the protective layer. The planarization layer can be made of an acrylic resin, etc. The same applies when a planarization layer is disposed between the color filter and the microlens.

[0191] [Substrate]

[0192] Examples of substrates include quartz, glass, silicon wafers, resins, and metals. The substrate may include switching elements such as transistors, wiring, and an insulating layer thereon. Any material can be used for the insulating layer, as long as contact holes can be formed in a manner that allows the wiring to couple to the first electrode and ensures insulation from unconnected wiring. For example, resins such as polyimide, silicon oxide, or silicon nitride can be used.

[0193] [electrode]

[0194] As electrodes, a pair of electrodes can be used. This pair of electrodes is a first electrode and a second electrode. Specifically, the pair of electrodes can be an anode and a cathode. When an electric field is applied in the direction of light emission from the organic light-emitting device, the electrode with the higher potential is the anode, and the other is the cathode. Alternatively, the electrode that supplies holes to the light-emitting layer is the anode, and the electrode that supplies electrons is the cathode.

[0195] The material constituting the anode preferably has the highest possible work function. Examples of usable materials include elemental metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten, mixtures thereof, alloys thereof, and metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide. Additionally, conductive polymers such as polyaniline, polypyrrole, and polythiophene can also be used.

[0196] These electrode materials can be used alone or in combination of two or more. The anode can be formed from a single layer or multiple layers.

[0197] When the electrode is used as a reflective electrode, materials such as chromium, aluminum, silver, titanium, tungsten, molybdenum, their alloys, or laminates thereof can be used. These materials can also be used as reflective films that do not function as electrodes. When the electrode is used as a transparent electrode, a transparent conductive oxide layer made of, for example, indium tin oxide (ITO) or indium zinc oxide can be used; however, the electrode is not limited to these. The electrode can be formed using photolithography.

[0198] Materials with a low work function are preferred as constituent materials of the cathode. Examples include elemental metals, such as alkali metals like lithium, alkaline earth metals like calcium, aluminum, titanium, manganese, silver, lead, and chromium, as well as mixtures containing them. Alternatively, alloys made by combining these elemental metals can also be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper, zinc-silver, etc., can be used. Metal oxides, such as indium tin oxide (ITO), can also be used. These electrode materials can be used alone or in combination of two or more. The cathode can have a single-layer or multi-layer structure. In particular, silver is preferred. To reduce silver aggregation, silver alloys are more preferred. Any alloy ratio can be used, as long as it reduces silver aggregation. The ratio of silver to another metal can be, for example, 1:1 or 3:1.

[0199] A top-emitting device can be provided using a cathode formed from a conductive oxide layer, such as ITO. A bottom-emitting device can be provided using a cathode formed from a reflective electrode, such as aluminum (Al). There are no particular limitations on the cathode. There are no particular limitations on the method used to form the cathode, but DC sputtering or AC sputtering methods are more preferred because they provide good film coverage and thus facilitate the reduction of resistance.

[0200] [Organic compound layer]

[0201] The organic compound layer can be formed as a single layer or multiple layers. When multiple layers are present, they can be named according to their function as a hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, or electron injection layer. The organic compound layer is mainly made of organic compounds and may contain inorganic atoms and inorganic compounds. For example, each organic compound layer may contain, for example, copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, or zinc. The organic compound layer can be disposed between the first electrode and the second electrode and can be configured to contact the first electrode and the second electrode.

[0202] The organic compound layer (e.g., hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, or electron injection layer) included in the organic light-emitting device according to this embodiment is formed by the following method.

[0203] For the organic compound layer included in the organic light-emitting device according to this embodiment, a dry process, such as vacuum evaporation, ionization evaporation, sputtering, or plasma processing, can be used. Alternatively, instead of a dry process, a wet process can be used, in which the material is dissolved in a suitable solvent and then a film is formed by a known coating method (e.g., spin coating, dip coating, casting, LB technology, or inkjet printing).

[0204] When the layer is formed by methods such as vacuum evaporation or solution coating, crystallization is unlikely to occur, and excellent stability over time is achieved. In the case of film formation by coating, the film can also be formed in combination with a suitable binder resin.

[0205] Examples of adhesive resins include, but are not limited to, polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenolic resin, epoxy resin, silicone resin, and urea resin.

[0206] These adhesive resins can be used alone as homopolymers or copolymers, or in combination as a mixture of two or more. Furthermore, additives, such as known plasticizers, antioxidants, and UV absorbers, can be used as needed.

[0207] [Protective Layer]

[0208] A protective layer can be disposed on the cathode. For example, glass with a desiccant can be bonded to the cathode to reduce, for example, water ingress into the organic compound layer, thereby reducing the occurrence of display defects. In another embodiment, a passivation film made of, for example, silicon nitride can be disposed on the cathode to reduce, for example, water ingress into the organic compound layer. For example, after the cathode is formed, the substrate can be transferred to another chamber without breaking the vacuum, and a silicon nitride film with a thickness of 2 μm can be formed by CVD to form a protective layer. After film deposition by CVD, the protective layer can be formed by atomic layer deposition (ALD). Examples of materials for the layer formed by ALD include, but are not limited to, silicon nitride, silicon oxide, and aluminum oxide. Silicon nitride can be deposited on the layer formed by ALD by CVD. The film formed by ALD can have a smaller thickness than the film formed by CVD. Specifically, the thickness of the film formed by ALD can be less than 50% of the thickness of the film formed by CVD, or even less than 10%.

[0209] [Color Filter]

[0210] Color filters can be disposed on a protective layer. For example, considering the size of the organic light-emitting device (OLED), the color filter can be disposed on another substrate and attached to the substrate on which the OLED is disposed. The color filter can be formed by patterning on the protective layer using photolithography. The color filter can be made of a polymer.

[0211] [Planning Layer]

[0212] A planarization layer can be disposed between the color filter and the protective layer. The planarization layer is provided to reduce the unevenness of the underlying layer. The planarization layer can be referred to as a material resin layer, without limiting its purpose. The planarization layer can be made of organic compounds, and can have low or high molecular weight compounds, with high molecular weight compounds being preferred.

[0213] The planarization layer can be disposed above and below the color filter and can be composed of the same or different constituent materials. Specific examples include polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenolic resin, epoxy resin, silicone resin, and urea resin.

[0214] [Microlens]

[0215] The organic light-emitting device according to this embodiment may include optical components, such as microlenses, on the light-emitting side. Microlenses may be made of acrylic resin or epoxy resin, etc. Microlenses can be used to increase the amount of light emitted from the organic light-emitting device and control the direction of the emitted light. Microlenses may have a hemispherical shape. In the case of a hemispherical shape, there exists a tangent parallel to the insulating layer in the tangent of the hemisphere. The contact point tangent to the hemisphere is the vertex of the microlens. For any cross-sectional view, the vertex of the microlens can be determined in the same way. That is, in the semicircular tangent of the microlens in the cross-sectional view, there exists a tangent parallel to the insulating layer, and the contact point between the tangent and the semicircle is the vertex of the microlens.

[0216] The midpoint of a microlens can also be defined. In the cross-section of a microlens, when assuming a line segment is drawn from the starting point of one arc to the starting point of another arc, the midpoint of the line segment can be called the midpoint of the microlens. The cross-section that determines the vertex and midpoint can be a cross-section perpendicular to the insulating layer.

[0217] [Opposing substrate]

[0218] A counter substrate may be disposed on a planarization layer. The counter substrate is disposed at a position corresponding to the aforementioned substrate, and is therefore called a counter substrate. The counter substrate may be made of the same constituent material as the aforementioned substrate. When the aforementioned substrate is referred to as the first substrate, the counter substrate may be referred to as the second substrate.

[0219] [Pixel Circuit]

[0220] The light-emitting device may include pixel circuitry coupled to an organic light-emitting device. The pixel circuitry may be an active matrix type that independently controls the emission of light from a first light-emitting device and a second light-emitting device. The active matrix type circuitry may be voltage-programmable or current-programmable. The driving circuitry includes pixel circuitry for each pixel. The pixel circuitry may include a light-emitting device, a transistor controlling the brightness of emitted light from the light-emitting device, a transistor controlling the timing of light emission, a capacitor maintaining the gate voltage of the transistor to control the brightness of the emitted light, and a transistor connected to GND when the light-emitting device is not in use.

[0221] The light-emitting device includes a display area and a surrounding area disposed around the display area. The display area includes pixel circuitry, and the surrounding area includes display control circuitry. The mobility of the transistors contained in the pixel circuitry may be lower than that of the transistors contained in the display control circuitry.

[0222] The slope of the current-voltage characteristic of the transistor contained in the pixel circuit can be less than that of the current-voltage characteristic of the transistor contained in the display control circuit. The slope of the current-voltage characteristic can be measured using the so-called Vg-Ig characteristic.

[0223] The transistors contained in the pixel circuit are transistors coupled to light-emitting devices, such as the first light-emitting device.

[0224] [pixel]

[0225] An organic light-emitting device comprises multiple pixels. Each pixel includes subpixels configured to emit different colors from each other. Subpixels can have corresponding RGB emission colors.

[0226] Light is exposed from the pixel's region (also called the pixel aperture). This region is the same as the first region. The pixel aperture can be less than 15 μm or greater than 5 μm. More specifically, the pixel aperture can be, for example, 11 μm, 9.5 μm, 7.4 μm, or 6.4 μm.

[0227] The distance between subpixels can be less than 10 μm. Specifically, this distance can be 8 μm, 7.4 μm, or 6.4 μm.

[0228] Pixels can be arranged in a known pattern in a planar graph. For example, stripe patterns, delta patterns, PenTile matrix patterns, or Bayer patterns can be used. The shape of each sub-pixel in the planar graph can be any known shape. Examples include quadrilaterals such as rectangles and rhombuses, as well as hexagons. Of course, if a shape is close to a rectangle but not exactly the same shape, it is included within the rectangle. Sub-pixel shapes and pixel arrangements can be combined.

[0229] (5) Application of organic light-emitting devices according to this implementation plan

[0230] The organic light-emitting device according to this embodiment can be used as a component of display devices or lighting devices. Other applications include exposure light sources for electrophotographic image forming equipment, backlights for liquid crystal displays, and light-emitting devices including white light sources with color filters.

[0231] The display device may be an image information processing unit, which includes an image input unit that receives image information from an area CCD, a linear CCD, or a memory card, an information processing unit that processes the input information, and a display unit that displays the input image.

[0232] The display unit of a camera device or inkjet printer may have a touch panel function. The driving method for the touch panel function may be, but is not specifically limited to, infrared, electrostatic capacitive, resistive film, or electromagnetic induction methods. The display device can also be used in the display unit of a multifunction printer.

[0233] The display device according to this embodiment is described below with reference to the accompanying drawings.

[0234] Figure 1A and1B Each of the above is a schematic cross-sectional view illustrating an example of a display device including an organic light-emitting device and a transistor coupled to the organic light-emitting device. Each transistor is an example of an active element. The transistor may be a thin-film transistor (TFT).

[0235] Figure 1A An example of a pixel, which is a constituent element of a display device according to this embodiment, is shown. The pixel includes sub-pixels 10. Sub-pixels are divided into 10R, 10G, and 10B according to their emission characteristics. The emitted color can be distinguished by the wavelength of light emitted from the light-emitting layer. Light emitted from the sub-pixels can be selectively transmitted or color-converted using, for example, a color filter. Each sub-pixel includes a reflective electrode 2 serving as a first electrode located above the 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.

[0236] Transistors and capacitors can be disposed below or within interlayer insulating layer 1. Each transistor can be electrically coupled to a corresponding one of the first electrodes via, for example, a contact hole (not shown).

[0237] The insulating layer 3 is also referred to as a bank or pixel separation film. The insulating layer covers the edges of each first electrode and surrounds the first electrode. The portion not covered by the insulating layer is in contact with the organic compound layer 4 and serves as the light-emitting area.

[0238] The organic compound layer 4 includes 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.

[0239] The second electrode 5 can be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0240] Protective layer 6 reduces the penetration of moisture into the organic compound layer. Although the protective layer is shown as a single layer, it can be formed from multiple layers. Each layer can be an inorganic compound layer or an organic compound layer.

[0241] Color filters 7 are classified into 7R, 7G, and 7B according to their color. Color filters can be disposed on a planarization film (not shown). A resin protective layer (not shown) can be disposed on the color filters. Color filters can also be disposed on the protective layer 6. Optionally, color filters can be disposed on opposing substrates such as a glass substrate and then bonded.

[0242] Figure 1BThe illustrated display device 100 includes an organic light-emitting device 26 and a TFT 18 as examples of transistors. A substrate 11, made of, for example, glass or silicon, is provided, and an insulating layer 12 is disposed thereon. Active elements, such as the TFT 18, are arranged on the insulating layer. A gate electrode 13, a gate insulating film 14, and a semiconductor layer 15 are disposed for each active element. Each active element 18 also includes the semiconductor layer 15, a drain electrode 16, and a source electrode 17. The active elements 18 are covered by an insulating film 19. An anode 21 included in the organic light-emitting device 26 is coupled to the source electrode 17 through a contact hole 20 provided in the insulating film.

[0243] The electrical connection mode between the electrodes (anode and cathode) included in each organic light-emitting device 26 and the electrodes (source electrode and drain electrode) included in a corresponding TFT is not limited to... Figure 1B The pattern shown indicates that it is sufficient for either the anode or cathode to be electrically coupled to either the source or drain electrode of the TFT. TFT stands for Thin Film Transistor.

[0244] exist Figure 1B In the display device 100 shown, each organic compound layer is shown as a single layer; however, the organic compound layer 22 may be formed of multiple layers. A first protective layer 24 and a second protective layer 25 are disposed on the cathode 23 to reduce the degradation of the organic light-emitting device.

[0245] Although transistors are used as Figure 1B The switching element in the display device 100 shown may be replaced by other switching elements.

[0246] Figure 1B The transistors used in the illustrated display device 100 are not limited to transistors using a single-crystal silicon wafer, but can also be thin-film transistors comprising an active layer on an insulating surface of a substrate. Examples of active layers include single-crystal silicon, non-single-crystal silicon materials such as amorphous silicon and microcrystalline silicon, and non-single-crystal oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Thin-film transistors are also referred to as TFT elements.

[0247] Figure 1B The transistors in the display device 100 shown can be formed in a substrate such as a Si substrate. The phrase "formed in a substrate" indicates that the transistors are produced by processing a substrate such as a Si substrate. When a transistor is formed in a substrate, the substrate and the transistor can be considered to be formed integrally.

[0248] In the organic light-emitting device according to this embodiment, the brightness of the emitted light is controlled by a TFT element, which is an example of a switching element; therefore, images can be displayed at corresponding brightness levels by arranging multiple organic light-emitting devices in a plane. The switching element according to this embodiment is not limited to a TFT, but can also be a low-temperature polysilicon transistor or an active matrix driver formed on a substrate such as a Si substrate. The expression "on the substrate" can also be described as "in the substrate." The choice between forming transistors in the substrate and using TFTs depends on the size of the display unit. For example, when the display unit has a size of approximately 0.5 inches, the organic light-emitting device is preferably disposed on a Si substrate.

[0249] Figure 2 This is a schematic diagram illustrating an example of a display device according to this embodiment. The display device 1000 may include a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008, located between an upper cover 1001 and a lower cover 1009. The display panel 1005 may include an organic light-emitting device according to this embodiment. The touch panel 1003 and the display panel 1005 are coupled to flexible printed circuits (FPCs) 1002 and 1004, respectively. The circuit board 1007 includes printed transistors. Unless the display device is a portable device, the battery 1008 is not required. Even if the display device is a portable device, the battery 1008 may be located in different positions.

[0250] The display device according to this embodiment may include a color filter having red, green, and blue portions. In the color filter, the red, green, and blue portions may be arranged in a Δ configuration.

[0251] The display device according to this embodiment can be used as a display unit of a portable terminal. In this case, the display device can have both display and operation functions. Examples of portable terminals include mobile phones such as smartphones, tablet computers, and head-mounted displays.

[0252] The display device according to this embodiment can be used as a display unit of a camera device, which includes an imaging device that receives light. The camera device may include a display unit that displays information acquired by the imaging device. The display unit may be an external display unit exposed to the camera device or a display unit disposed within a viewfinder. The camera device may be a digital camera or a digital camcorder.

[0253] Figure 3AThis is a schematic diagram illustrating an example of a camera device according to this embodiment. The camera device 1100 may include a viewfinder 1101, a rear display 1102, an operation unit 1103, and a housing 1104. The viewfinder 1101 and the rear display 1102 may include organic light-emitting devices according to this embodiment. In this case, in addition to the image to be captured, the viewfinder 1101 and the rear display 1102 may also display environmental information, imaging instructions, etc. Environmental information may include, for example, the intensity of external light, the direction of external light, the speed of movement of the object, and the likelihood that the object will be obscured by an obstacle.

[0254] The opportune moment for imaging is only a short period; therefore, it is best to display information as quickly as possible. Therefore, a display device including an organic light-emitting device according to this embodiment is preferred. This is because organic light-emitting devices have a fast response time.

[0255] The imaging device 1100 may also include an optical unit (not shown). The optical unit may include a single lens or multiple lenses and is configured to form an image on the imaging device within the housing 1104. The relative positions of the multiple lenses can be adjusted to adjust the focus. This operation can also be performed automatically. The imaging device may also be referred to as a photoelectric conversion device. Examples of image capture methods employed in a photoelectric conversion device may include methods for detecting differences from previous images and methods for segmenting images from continuously recorded images rather than capturing images sequentially.

[0256] Figure 3B This is a schematic diagram illustrating an example of an electronic device according to this embodiment. The electronic device 1200 includes a display unit 1201, an operation unit 1202, and a housing 1203. The housing 1203 may house circuitry, a printed circuit board including the circuitry, a battery, and a communication unit. The operation unit 1202 may be a button or touch panel type response unit. The operation unit may be a biometric unit that recognizes fingerprints to perform functions such as unlocking. An electronic device including a communication unit may also be called a communication device. The electronic device may also have camera functionality by including a lens and a camera device. Images captured by the camera functionality are displayed on the display unit. Examples of electronic devices include smartphones and laptop computers.

[0257] Figure 4A and Figure 4B Each is a schematic diagram illustrating an example of a display device according to this embodiment. Figure 4A A display device, such as a television monitor or a PC monitor, is shown. The display device 1300 includes a housing 1301 and a display unit 1302. The display unit 1302 may include an organic light-emitting device according to this embodiment.

[0258] The display device 1300 may include a base 1303 supporting the housing 1301 and the display unit 1302. The base 1303 is not limited to... Figure 4A As shown in the diagram. The lower side of the housing 1301 can also be used as a base.

[0259] The housing 1301 and the display unit 1302 can be curved. The radius of curvature can be greater than 5,000 mm and less than 6,000 mm.

[0260] Figure 4B This is a schematic diagram illustrating an example of a display device according to this embodiment. Figure 4B The illustrated display device 1310 is foldable and is a so-called foldable display device. The display device 1310 includes a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may include organic light-emitting devices according to this embodiment. The first display unit 1311 and the second display unit 1312 may be a single seamless display device. The first display unit 1311 and the second display unit 1312 may be separated from each other at the bending point. The first display unit 1311 and the second display unit 1312 may display different images from each other. Optionally, a single image may be displayed in the first and second display units.

[0261] Figure 5A This is a schematic diagram illustrating an example of a lighting device according to this embodiment. The lighting device 1400 may include a housing 1401, a light source 1402, and a circuit board 1403. The light source 1402 may include an organic light-emitting device according to this embodiment. The lighting device 1400 may include an optical film 1404 to improve the color rendering properties of the light source. The lighting device 1400 may also include a light diffusing unit 1405 to effectively diffuse light from the light source. When the lighting device 1400 includes the light diffusing unit 1405, the device can deliver light over a wide range. The optical film 1404 and the light diffusing unit 1405 may be disposed on the light-emitting side of the lighting device. A cover may be disposed on the outermost portion if necessary.

[0262] Lighting devices are, for example, devices that illuminate a room. Lighting devices can emit white, neutral white, or any color of light from blue to red. Lighting devices according to this embodiment may include lighting control circuitry to control them. Lighting devices according to this embodiment may also include a power supply circuit connected to the organic light-emitting device according to this embodiment. The power supply circuit may be a circuit that converts AC voltage to DC voltage. The color temperature of white light is 4200K, and the color temperature of neutral white light is 5000K. Lighting devices according to this embodiment may also include color filters.

[0263] The lighting device according to this embodiment may include a heat dissipation unit. The heat dissipation unit is configured to release heat from inside the device to the outside and uses materials with high thermal conductivity, such as metals and ceramics.

[0264] Figure 5B This is a schematic diagram of an automobile as an example of a moving body according to this embodiment. The automobile includes taillights, which are examples of lighting units. Automobile 1500 includes taillights 1501 and an automobile body 1503, and can be configured to illuminate the taillights when an operation such as braking is performed. The automobile body 1503 may also be referred to as the body. Automobile 1500 may include a window 1502 attached to the automobile body 1503. Taillights 1501 may include an organic light-emitting device according to this embodiment. The taillights may include a protective member to protect the light source. The protective member can be made of any material, as long as it has a certain degree of strength and is transparent. The protective member is preferably made of, for example, polycarbonate. Polycarbonate may be mixed with, for example, furan dicarboxylic acid derivatives or acrylonitrile derivatives.

[0265] Window 1502 can be a transparent display, unless it is a window used for inspecting areas at the front and rear of a vehicle. The transparent display may include an organic light-emitting device according to this embodiment. In this case, the constituent materials of the organic light-emitting device according to the invention, such as electrodes, are formed from transparent components.

[0266] The mobile body according to this embodiment includes one or both of a drive force generating unit configured to generate a driving force primarily used for the movement of the mobile body and a rotating body primarily used for the movement of the mobile body. The drive force generating unit may be an engine or motor, etc. The rotating body may be a tire, wheel, ship propeller, or aircraft propeller, etc. Specifically, the mobile body may be a bicycle, car, train, ship, airplane, or drone, etc. The mobile body may include a main body and an illumination unit attached to the main body. The illumination unit may emit light, making the position of the main body identifiable.

[0267] Reference Figure 6A and Figure 6B Examples of applications of the display device described in the above embodiments are given. The display device can be used in systems that can be worn as wearable devices, such as smart glasses, head-mounted displays, and smart contact lenses. Display devices available in wearable devices may include camera devices capable of photoelectric conversion of visible light and display devices capable of emitting visible light.

[0268] Figure 6A and Figure 6B Each is a schematic diagram illustrating an example of glasses (smart glasses) according to this embodiment. (Refer to...) Figure 6AThe glasses 1600 (smart glasses) are described. The glasses 1600 includes a display unit on the rear side of a lens 1601. The display unit may include an organic light-emitting device according to the present invention. Additionally, a camera device 1602, such as a CMOS sensor or a SPAD, may be disposed on the front side of the lens 1601.

[0269] The glasses 1600 also include a control unit 1603. The control unit 1603 acts as a power supply to the camera device 1602 and the display unit. The control unit 1603 controls the operation of the camera device 1602 and the display unit. The lens 1601 includes an optical system for focusing light from the camera device 1602 and the display unit.

[0270] Reference Figure 6B Glasses 1610 (smart glasses) are described. Glasses 1610 includes a control unit 1612. The control unit 1612 is equipped with a display device including an organic light-emitting device according to the invention. The control unit 1612 may also include a camera device equivalent to a camera device 1602. A lens 1611 is provided with an optical system for projecting light emitted from the control unit 1612, and an image is projected onto the lens 1611. The control unit 1612 acts as a power supply for powering the camera device and the display device, and controls the operation of the camera device and the display device. The control unit may include a gaze detection unit for detecting the wearer's gaze. Infrared radiation can be used for gaze detection. An infrared light emitting unit emits infrared light toward the eyeball of a user gazing at the displayed image. The image of the eyeball is captured by a camera unit including a light receiving element that detects infrared light reflected from the eyeball in the emitted infrared light. Image quality degradation is reduced by providing a light reduction unit that reduces light from the infrared light emitting unit to the display unit when viewed in a planar view.

[0271] The control unit 1612 detects the user's gaze at the displayed image from an eye image captured using infrared light. Any known method can be used for gaze detection using captured eye images. As an example, a gaze detection method based on Purkinje images of the reflection of illumination light on the cornea can be used.

[0272] More specifically, the gaze detection process is performed based on the pupil-corneal reflection method. Using the pupil-corneal reflection method, the user's gaze is detected by generating a gaze vector representing the direction (rotation angle) of the eyeball based on the pupil image and the Purkinje image contained in the captured eyeball image.

[0273] The display device according to this embodiment may include a camera device having a light receiving element, and may control the image displayed on the display device based on the user's gaze information from the camera device.

[0274] Specifically, in a display device, a first field of view and a second field of view, different from the first field of view, are determined based on gaze information. The first and second field of view can be determined by the control unit of the display device, or by receiving information determined by an external control unit. Within the display area of ​​the display device, the display resolution of the first field of view can be controlled to be higher than that of the second field of view. That is, the resolution of the second field of view can be lower than that of the first field of view.

[0275] The display area includes a first field of view and a second field of view, which is different from the first field of view. Based on gaze information, a higher-priority region is determined from the first and second field of view. The first and second field of view can be determined by the control unit of the display device, or by receiving information determined by an external control unit. The resolution of the higher-priority region can be controlled to be higher than the resolution of all other regions. In other words, the resolution of relatively low-priority regions can be lower.

[0276] Artificial intelligence (AI) can be used to determine primary and high-priority fields of view. AI can be a model constructed to estimate the distance from the image of the eye to a target object located in the gaze direction, using images of the eye and the actual gaze direction within the image as teaching data. AI can be incorporated into a display device, a camera device, or an external device. When the external device includes AI, smart glasses that also include a camera device for capturing external images are preferably used. The smart glasses can display the captured external information in real time.

[0277] Figure 7A This is a schematic diagram of an example of the image forming apparatus of this embodiment. The image forming apparatus 40 is an electrophotographic image forming apparatus, including a photoreceptor 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transfer unit 32, a transport roller 33, and a fixing unit 35. Light 29 is irradiated from the exposure light source 28 to form an electrostatic latent image on the surface of the photoreceptor 27. The exposure light source 28 may include an organic light-emitting device according to this embodiment. The developing unit 31 contains, for example, a toner. The charging unit 30 charges the photoreceptor 27. The transfer unit 32 transfers the developed image to a recording medium 34. The transport roller 33 transports the recording medium 34. The recording medium 34 is, for example, paper. The fixing unit 35 fixes the image formed on the recording medium 34.

[0278] Figure 7B and 7CEach section illustrates the exposure light source 28 and provides a schematic diagram of the plurality of light-emitting portions 36 arranged on the long substrate. Arrows 37 each indicate the row direction of the organic light-emitting devices. The row direction is the same as the direction of the axis of rotation of the photoreceptor 27. This direction can also be referred to as the long axis direction of the photoreceptor 27. Figure 7B The arrangement in which the light-emitting portion 36 is arranged along the long axis of the photoreceptor 27 is shown. Figure 7C and Figure 7B The difference lies in that the light-emitting portions 36 are arranged alternately in the row direction in the first and second rows. The first and second rows are located at different positions in the column direction. In the first row, multiple light-emitting portions 36 are spaced apart. The second row has light-emitting portions 36 at positions corresponding to the positions between the light-emitting portions 36 in the first row. In other words, multiple light-emitting portions 36 are also spaced apart in the column direction. Figure 7C The arrangement in the middle can also be described as, for example, grid arrangement, staggered arrangement, or checkered pattern.

[0279] As described above, a device including an organic light-emitting device according to this embodiment can achieve a stable display with good image quality even over a long period of time.

[0280] Example

[0281] The invention will now be described through examples. However, the invention is not limited thereto.

[0282] [Example 1 (Synthesis of Compound A-1)]

[0283] Compound A-1 was synthesized according to the following synthetic route.

[0284] [Chemical Formula 36]

[0285]

[0286] 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 the mixture was stirred at 80 °C for 16 hours. The reaction mixture was extracted with toluene, and the crude product was purified by an organic solvent GPC column (JAIGEL-2H-40, Nippon Analytical Industry Co., Ltd.; eluent: chloroform) to give compound A-1 (238 mg) as a yellow powder. THF was added to the yellow powder, and the resulting solution was analyzed by ultra-high performance liquid chromatography (UPLC)-MS, resulting in the identification of the compound (m / z = 830.435, C). 60 H 54 N4).

[0287] [Example 2 (Synthesis of Compound A-2)]

[0288] Compound A-2 was synthesized according to the following synthetic route.

[0289] [Chemical Formula 37]

[0290]

[0291] 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 the mixture was stirred at 150 °C for 16 hours. The reaction mixture was extracted with toluene, and the crude product was purified by an organic solvent GPC column (JAIGEL-2H-40, Nippon Analytical Industry Co., Ltd.; eluent: chloroform) to give compound A-2 (288 mg) as a yellow powder. THF was added to the yellow powder, and the resulting solution was analyzed by ultra-high performance liquid chromatography (UPLC)-MS, resulting in the identification of the compound (m / z = 830.435, C). 60 H 54 N4).

[0292] [Example 3 (Preparation and Evaluation of Organic Light-Emitting Devices)]

[0293] In Example 3, compound A-1 was used as a guest material in the light-emitting layer. An organic light-emitting device was prepared by the following method, comprising 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 disposed on a substrate in the following order.

[0294] An ITO film with a thickness of 100 nm was formed on a glass substrate using sputtering to serve as the anode. The resulting substrate was used as a transparent conductive support substrate (ITO substrate). The glass substrate with the ITO film was subsequently ultrasonically cleaned with acetone and isopropanol (IPA), washed with boiling IPA, and dried. Following this, the glass substrate was subjected to UV-ozone cleaning. The glass substrate treated in this manner was used as a transparent conductive support substrate.

[0295] Next, in 10 -5 In a vacuum chamber, resistance heating is used to sequentially deposit 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 via vacuum evaporation, with an electrode area of ​​3 mm². 2 This is achieved through a specific method. The layer structure is described below.

[0296] [Table 6]

[0297]

[0298] To prevent the organic light-emitting device from deteriorating due to moisture adsorption, the resulting structure was covered with a protective glass plate in a dry air atmosphere and sealed with an acrylic resin adhesive. The organic light-emitting device was thus fabricated as described above.

[0299] The characteristics of the obtained organic light-emitting devices were measured and evaluated. The organic light-emitting devices were tested at 10 mA / cm². 2 The external quantum yield (EQE) at the current density is 4.46%.

[0300] In addition, at 20mA / cm 2 A continuous operation test was performed using a current density to measure the time (LT80) when the brightness decay percentage reached 20% from the initial brightness. When the time when the brightness decay percentage reached 20% in Comparative Example 1 was defined as 1.0, the relative value of LT80 in this embodiment was 2.41.

[0301] The full width at half maximum (FWHM) of the emission spectrum was determined to be 29 nm.

[0302] In this embodiment, the measuring instruments are as follows: Specifically, the current-voltage characteristics are measured using a DC voltage-current source / monitor 6253 manufactured by ADC Corporation, and the luminance is measured using a spectroradiometer SR-LEDW from Topcon Corporation.

[0303] [Example 4 and Comparative Example 1 (Preparation and Evaluation of Organic Light-Emitting Devices)]

[0304] The organic light-emitting device of Example 4 was prepared in the same manner as in Example 3, except that compound A-1 was replaced with compound A-2. The organic light-emitting device of Comparative Example 1 was prepared in the same manner as in Example 3, except that compound A-1 was replaced with compound Ref-1. The characteristics of the organic light-emitting devices thus prepared were measured and evaluated in the same manner as in Example 3. The results are shown in Table 7.

[0305] [Table 7]

[0306]

[0307] As shown in Table 7, the organic compounds according to the present invention exhibit superior device lifetime compared to the comparative compound Ref-1. This is believed to be because the organic compounds according to the present invention have electron-withdrawing groups and therefore have lower HOMO levels (i.e., further from vacuum levels). Furthermore, the organic compounds according to the present invention exhibit smaller full width at half maximum (FWHM) than the comparative compound Ref-1.

[0308] In summary, the organic compounds according to the present invention are organic compounds with excellent oxidative stability. Therefore, when the organic compounds according to the present invention are used in organic light-emitting devices, organic light-emitting devices with excellent device lifetimes can be provided. Furthermore, when an organic compound according to the present invention with excellent oscillator strength is used in an organic light-emitting device, an organic light-emitting device with excellent quantum yield (luminous efficiency) can be provided. Moreover, when an organic compound according to the present invention with excellent color purity is used in an organic light-emitting device, an organic semiconductor emitting light with even better color purity can be provided.

[0309] The present invention may also have the following structure.

[0310] (Construction 1)

[0311] An organic compound represented by formula (1).

[0312] [Chemical Formula 38]

[0313]

[0314] In formula (1), rings A to C are each independently selected from the group consisting of substituted or unsubstituted aryl groups having 6 or more but less than 50 carbon atoms and substituted or unsubstituted heterocyclic groups having 3 or more but less than 50 carbon atoms. When any of rings A to C has a substituent, the substituent is a deuterium atom, alkyl, aryl, heterocyclic group, silyl, amino, or cyano.

[0315] 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.

[0316] n is an integer greater than or equal to 1.

[0317] (Construction 2)

[0318] The organic compound described in Construction 1, wherein, in Formula (1), the electron-withdrawing group is trifluoromethyl, trichloromethyl, nitro, cyano, aldehyde, ketone, ester, carboxylic acid, sulfonyl, sulfonic acid, pyridyl, triazine, or a halogen atom.

[0319] (Construction 3)

[0320] Construct the organic compound described in 1 or 2, wherein, in formula (1), the electron-withdrawing group is a trifluoromethyl, cyano, or fluorine atom.

[0321] (Construction 4)

[0322] Construct an organic compound according to any one of 1 to 3, wherein, in formula (1), EWG is an aryl group having at least one electron-withdrawing group and having 6 or more and 20 or less carbon atoms, or a heterocyclic group having at least one or more electron-withdrawing groups and having 3 or more and 17 or less carbon atoms.

[0323] (Construction 5)

[0324] Construct an organic compound according to any one of 1 to 4, wherein the aryl group contained in EWG in formula (1) is benzene.

[0325] (Construction 6)

[0326] Construct an organic compound according to any one of 1 to 5, wherein, in formula (1), rings A to C are each a substituted or unsubstituted aryl group having 6 or more and 20 or less carbon atoms and a substituted or unsubstituted heterocyclic group having 3 or more and 17 or less carbon atoms.

[0327] (Construction 7)

[0328] Construct an organic compound according to any one of 1 to 6, wherein, in formula (1), ring A is a benzene skeleton or a naphthalene skeleton, and n is an integer greater than 1 and less than 4.

[0329] (Construction 8)

[0330] Construct an organic compound according to any one of 1 to 7, wherein, in formula (1), each ring B is a benzene skeleton, a benzofuran skeleton, or a benzothiophene skeleton.

[0331] (Construction 9)

[0332] Construct an organic compound according to any one of 1 to 8, wherein, in formula (1), each ring C is a benzene skeleton, a benzofuran skeleton, or a benzothiophene skeleton.

[0333] (Construction 10)

[0334] An organic compound represented by formula (2) or (3).

[0335] [Chemical Formula 39]

[0336]

[0337] In equation (2), R 1 To R16 Each is independently selected from the group consisting of hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted silyl group, substituted or unsubstituted amino group, and 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 、or R 13 and R 14 They can form a cycle together, provided that R 15 and R 16 At least one of them is an electron-withdrawing group, an aryl group having at least one or more electron-withdrawing groups, or a heterocyclic group having at least one or more electron-withdrawing groups.

[0338] In equation (3), R 21 To R 38 Each is independently selected from the group consisting of hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted silyl group, substituted or unsubstituted amino group, and 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 、or R 33 and R 34They can form a cycle together, provided that R 35 To R 38 At least one of them is an electron-withdrawing group, an aryl group having at least one or more electron-withdrawing groups, or a heterocyclic group having at least one or more electron-withdrawing groups.

[0339] (Construction 11)

[0340] The organic compound described in Construction 10, wherein in each of Formulas (2) and (3), the electron-withdrawing group is trifluoromethyl, trichloromethyl, nitro, cyano, aldehyde, ketone, ester, carboxylic acid, sulfonyl, sulfonic acid, pyridyl, triazine, or a halogen atom.

[0341] (Construction 12)

[0342] Construct the organic compound described in 10 or 11, wherein in each of formulas (2) and (3), the electron-withdrawing group is a trifluoromethyl, cyano, or fluorine atom.

[0343] (Construction 13)

[0344] Construct an organic compound according to any one of 10 to 12, wherein in each of formulas (2) and (3), each ring is a substituted or unsubstituted aryl group having 6 or more but less than 12 carbon atoms or a substituted or unsubstituted heterocyclic group having 3 or more but less than 12 carbon atoms.

[0345] (Construction 14)

[0346] Construct an organic compound according to any one of 10 to 13, wherein in each of formulas (2) and (3), each ring is a substituted or unsubstituted benzofuran skeleton or a substituted or unsubstituted benzothiophene skeleton.

[0347] (Construction 15)

[0348] An organic light-emitting device includes a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, wherein the organic compound layer contains an organic compound as described in any one of constructions 1 to 14.

[0349] (Construction 16)

[0350] The organic light-emitting device described in construction 15, wherein the organic compound layer includes a light-emitting layer and the light-emitting layer contains the organic compound.

[0351] (Construction 17)

[0352] The organic light-emitting device described in construction 16 is further comprising a first compound, wherein the lowest excitation singlet energy of the first compound is higher than that of the organic compound.

[0353] (Construction 18)

[0354] The organic light-emitting device described in Construction 17, wherein the first compound is a hydrocarbon compound containing fused polycyclic hydrocarbon groups.

[0355] (Construction 19)

[0356] Construct the organic light-emitting device as described in 17 or 18, wherein the light-emitting layer further contains a second compound, the second compound having a minimum excitation singlet energy higher than the minimum excitation singlet energy of the organic compound and lower than the minimum excitation singlet energy of the first compound.

[0357] (Construction 20)

[0358] A display device includes a plurality of pixels, wherein at least one of the plurality of pixels includes an organic light-emitting device configured as described in any one of 15 to 19, and a transistor coupled to the organic light-emitting device.

[0359] (Construction 21)

[0360] A photoelectric conversion device includes a camera configured to receive light and a display unit configured to display an image captured by the camera, wherein the display unit includes an organic light-emitting device configured as described in any one of 15 to 19.

[0361] (Construction 22)

[0362] An image display device includes a display unit comprising an organic light-emitting device as described in any one of 15 to 19, and a housing on which the display unit is disposed.

[0363] (Construction 23)

[0364] An electronic device includes a display unit comprising an organic light-emitting device configured as described in any one of 15 to 19, a housing having the display unit disposed therein, and a communication unit disposed in the housing and configured to communicate with the outside.

[0365] (Construction 24)

[0366] A wearable device includes a display unit comprising an organic light-emitting device configured as described in any one of 15 to 19, an optical system configured to focus light from the display unit, and a control unit configured to control the display of the display unit.

[0367] (Construction 25)

[0368] A lighting device comprising a light source including an organic light-emitting device constructed as described in any one of 15 to 19, and a housing provided with the light source.

[0369] (Construction 26)

[0370] A mobile body includes an illumination unit comprising an organic light-emitting device constructed as described in any one of 15 to 19, and a body on which the illumination unit is disposed.

[0371] (Construction 27)

[0372] An image forming apparatus includes a photoreceptor and an exposure light source configured to expose the photoreceptor, wherein the exposure light source includes an organic light-emitting device configured as described in any one of 15 to 19.

[0373] This invention is not limited to the embodiments described above, and various changes and modifications can be made within the spirit and scope of this invention. Therefore, in order to inform the public of the scope of this invention, the following claims are made.

[0374] This application claims priority based on Japanese Patent Application No. 2023-145293, filed on September 7, 2023, the entire contents of which are incorporated herein by reference.

[0375] Explanation of reference numerals in the attached figures

[0376] 1 interlayer insulation layer

[0377] 2 Reflecting Electrodes

[0378] 3 insulation layers

[0379] 4 Organic compound layer

[0380] 5 transparent electrodes

[0381] 6 protective layers

[0382] 7 color filters

[0383] 10 sub-pixels

[0384] 11 substrate

[0385] 12 insulation layers

[0386] 13 gate electrodes

[0387] 14 gate insulating film

[0388] 15 semiconductor layers

[0389] 16 drain electrodes

[0390] 17 source electrodes

[0391] 18 Thin Film Transistors

[0392] 19 Insulating Film

[0393] 20 contact holes

[0394] 21 Lower electrode

[0395] 22 organic compound layers

[0396] 23 Upper Electrode

[0397] 24 First protective layer

[0398] 25 Second protective layer

[0399] 26 Organic Light-Emitting Devices

[0400] 27 Photoreceptors

[0401] 28 Exposure Light Source

[0402] 29 light

[0403] 30 charging units

[0404] 31 developing units

[0405] 32 transfer units

[0406] 33 Conveyor Units

[0407] 34 Recording Media

[0408] 35 fixing units

[0409] 36 light-emitting parts

[0410] 37. The first direction parallel to the long axis of the photoreceptor

[0411] 40 Image forming equipment

[0412] 100 display devices

[0413] 1000 display devices

[0414] 1001 top cover

[0415] 1002 Flexible Printed Circuit

[0416] 1003 Touch Panel

[0417] 1004 Flexible Printed Circuit

[0418] 1005 display panel

[0419] 1006 Framework

[0420] 1007 circuit board

[0421] 1008 battery

[0422] 1009 bottom cover

[0423] 1100 camera equipment

[0424] 1101 Viewfinder

[0425] 1102 rear monitor

[0426] 1103 Operation Unit

[0427] 1104 housing

[0428] 1200 electronic devices

[0429] 1201 display unit

[0430] 1202 Operating Unit

[0431] 1203 casing

[0432] 1300 display device

[0433] 1301 framework

[0434] 1302 display unit

[0435] 1303 base

[0436] 1310 display device

[0437] 1311 First Display Unit

[0438] 1312 Second Display Unit

[0439] 1313 housing

[0440] 1314 bending point

[0441] 1400 lighting equipment

[0442] 1401 housing

[0443] 1402 light source

[0444] 1403 circuit board

[0445] 1404 optical film

[0446] 1405 light diffuser unit

[0447] 1500 cars

[0448] 1501 taillights

[0449] Window 1502

[0450] 1503 Car Body

[0451] 1600 Smart Glasses

[0452] 1601 lens

[0453] 1602 camera equipment

[0454] 1603 control unit

[0455] 1610 Smart Glasses

[0456] 1611 lens

[0457] 1612 control unit

Claims

1. An organic compound represented by formula (1): in, In formula (1), rings A to C are each independently selected from the group consisting of substituted or unsubstituted aryl groups having 6 or more but less than 50 carbon atoms and substituted or unsubstituted heterocyclic groups having 3 or more but less than 50 carbon atoms. When any of rings A to C has 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 greater than or equal to 1.

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

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.

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

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

6. The organic compound according to claim 1, wherein, In formula (1), rings A to C are each a substituted or unsubstituted aryl group having 6 or more but less than 20 carbon atoms and a substituted or unsubstituted heterocyclic group having 3 or more but less than 17 carbon atoms.

7. The organic compound according to claim 1, wherein, In equation (1), ring A is a benzene skeleton or a naphthalene skeleton, and n is an integer greater than 1 and less than 4.

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

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

10. An organic compound represented by formula (2) or (3): in, In equation (2), R 1 To R 16 Each is independently selected from the group consisting of hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted silyl group, substituted or unsubstituted amino group, and cyano group, and R 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 、or R 13 and R 14 They can be arbitrarily combined to form a ring, provided that R 15 and R 16 At least one of them is an electron-withdrawing group, an aryl group having at least one or more electron-withdrawing groups, or a heterocyclic group having at least one or more electron-withdrawing groups, and In equation (3), R 21 To R 38 Each is independently selected from the group consisting of hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted silyl group, substituted or unsubstituted amino group, and cyano group, and R 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 、or R 33 and R 34 They can be arbitrarily combined to form a ring, provided that R 35 To R 38 At least one of them is an electron-withdrawing group, an aryl group having at least one or more electron-withdrawing groups, or a heterocyclic group having at least one or more electron-withdrawing groups.

11. An organic light-emitting device comprising a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, wherein the organic compound layer contains the organic compound according to claim 1.

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

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

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

15. The organic light-emitting device according to claim 13, wherein the light-emitting layer further comprises a second compound, the second compound having a minimum excitation singlet energy higher than the minimum excitation singlet energy of the organic compound and lower than the minimum excitation singlet energy of the first compound.

16. A display device comprising a plurality of pixels, wherein at least one of the plurality of pixels comprises an organic light-emitting device according to any one of claims 11 to 15, and a transistor coupled to said organic light-emitting device.

17. A photoelectric conversion device comprising an imaging device configured to receive light, and a display unit configured to display an image captured by the imaging device, wherein the display unit comprises an organic light-emitting device according to any one of claims 11 to 15.

18. An image display device comprising a display unit including an organic light-emitting device according to any one of claims 11 to 15, and a housing on which the display unit is disposed.

19. An electronic device comprising a display unit including an organic light-emitting device according to any one of claims 11 to 15, a housing having the display unit disposed therein, and a communication unit disposed in the housing and configured to communicate with the outside.

20. A wearable device comprising a display unit including an organic light-emitting device according to any one of claims 11 to 15, an optical system configured to focus light from the display unit, and a control unit configured to control the display of the display unit.

21. A lighting device comprising a light source including an organic light-emitting device according to any one of claims 11 to 15, and a housing provided with said light source.

22. A mobile body comprising an illumination unit including an organic light-emitting device according to any one of claims 11 to 15, and a body on which the illumination unit is disposed.

23. An image forming apparatus comprising a photoreceptor and an exposure light source configured to expose the photoreceptor, wherein the exposure light source comprises an organic light-emitting device according to any one of claims 11 to 15.

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