Organic compound and organic light-emitting device

Abstract

To provide an organic compound with high efficiency and superior durability.SOLUTION: The present invention provides an organic compound represented by formula [3]. In the formula, Ar11 to Ar18 each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.SELECTED DRAWING: None

Description

Technical Field

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

Background Art

[0002] An organic light-emitting device (sometimes referred to as an organic electroluminescence device or an organic EL device) is an electronic device having a pair of electrodes and an organic compound layer disposed between these electrodes. By injecting electrons and holes from these pair of electrodes, excitons of a light-emitting organic compound in the organic compound layer are generated, and when the excitons return to the ground state, the organic light-emitting device emits light. The recent progress of organic light-emitting devices is remarkable, and its features include low driving voltage, various emission wavelengths, high-speed responsiveness, and the ability to make the light-emitting device thinner and lighter. By the way, the creation of compounds suitable for organic light-emitting devices has been actively carried out until now. This is because in providing a high-performance organic light-emitting device, the creation of a compound having excellent element lifetime characteristics is important. As compounds created so far, indolocarbazole derivative 1-a is described in Patent Document 1, and indolocarbazole derivatives 1-b and 1-c are described in Patent Document 2.

[0003]

Chemical Formula

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0005] However, for the organic light-emitting device examples containing compound 1-a described in Patent Document 1 and the organic light-emitting device examples containing compounds 1-b and 1-c described in Patent Document 2, further improvement in both luminous efficiency and durability characteristics is desired. The present invention has been made in view of the above problems, and an object thereof is to provide an organic compound and an organic light-emitting device having high efficiency and excellent durability characteristics.

Means for Solving the Problems

[0006] The organic compound according to the present invention is characterized by being represented by the following general formula [1] or [2].

[0007]

Chemical formula

Effects of the Invention

[0008] According to the present invention, when the organic compound according to the present invention is used in an organic light-emitting device, an organic light-emitting device excellent in device lifetime can be provided.

Brief Description of the Drawings

[0009]

Figure 1

Figure 2

Figure 3

Figure 4

Figure 5

Figure 6

Figure 7

Figure 8

Figure 9

Embodiments for Carrying Out the Invention

[0010] (1) Organic compound The organic compound of this embodiment is a compound represented by the following general formula [1] or [2].

[0011]

Chemical formula

[0012] <R 1 to R 7 > In general formulas [1] and [2], R 1 to R 7 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a cyano group, and a substituted or unsubstituted alkoxy group.

[0013] R 1 to R 5 At least one of them, preferably at least one of R 3 to R 5 More preferably, at least one of R 5 is preferably a group selected from a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. Also, R 6 , R 7 is preferably a substituted or unsubstituted aryl group, and more preferably a substituted or unsubstituted phenyl group.

[0014] Examples of the halogen atom include, but are not limited to, fluorine, chlorine, bromine, iodine, astatine, tennessine, etc.

[0015] The alkyl group may be an alkyl group having 1 to 20 carbon atoms. Examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, a tertiary butyl group, a secondary butyl group, an octyl group, a cyclohexyl group, a tertiary pentyl group, a 3-methylpentan-3-yl group, a 1-adamantyl group, a 2-adamantyl group, etc.

[0016] The aryl group may be an aryl group having 6 to 20 carbon atoms. Examples of the aryl group include, but are not limited to, a phenyl group, a naphthyl group, an indenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a phenanthryl group, a triphenylenyl group, a pyrenyl group, an anthranyl group, a perylenyl group, a chrysenyl group, a fluoranthenyl group, etc.

[0017] The heterocyclic group may be a heteroaryl group having 3 to 20 carbon atoms. Examples of the heterocyclic group include, but are not limited to, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a carbazolyl group, an acridinyl group, a phenanthrolyl group, etc.

[0018] Examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triphenylsilyl group, etc.

[0019] Examples of the amino group include, but are not limited to, an N-methylamino group, an N-ethylamino group, an N,N-dimethylamino group, an N,N-diethylamino group, an N-methyl-N-ethylamino group, an N-benzylamino group, an N-methyl-N-benzylamino group, an N,N-dibenzylamino group, an anilino group, an N,N-diphenylamino group, an N,N-dinaphthylamino group, an N,N-difluorenylamino group, an N-phenyl-N-tolylamino group, an N,N-ditolylamino group, an N-methyl-N-phenylamino group, an N,N-dianisolyamino group, an N-mesityl-N-phenylamino group, an N,N-dimesitylamino group, an N-phenyl-N-(4-tert-butylphenyl)amino group, an N-phenyl-N-(4-trifluoromethylphenyl)amino group, an N-piperidyl group, a carbazolyl group, an acridinyl group, a trimethylamino group, a triphenylamino group, etc.

[0020] The alkoxy group may be an alkoxy group having 1 to 10 carbon atoms. Examples of the alkoxy group include, but are not limited to, methoxy group, ethoxy group, propoxy group, isopropoxy group, tertiary butoxy group, 2-ethyl-octyloxy group, benzyloxy group and the like.

[0021] Examples of the substituent that the alkyl group, aryl group, heterocyclic group, silyl group, amino group, alkoxy group may further have include, but are not limited to, deuterium, alkyl groups such as methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, tertiary butyl group, aralkyl groups such as benzyl group, aryl groups such as phenyl group, biphenyl group, heterocyclic groups such as pyridyl group, pyrrolyl group, amino groups such as dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, ditolylamino group, alkoxy groups such as methoxy group, ethoxy group, propoxy group, aryloxy groups such as phenoxy group, halogen atoms such as fluorine, chlorine, bromine, iodine, cyano group and the like.

[0022] <Ar 1 to Ar 4 > In General Formulas [1] and [2], Ar 1 to Ar 4 each independently represents any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. Also, Ar 1 to Ar 4 each preferably independently represents any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. Further, Ar 1 to Ar 4 more preferably each independently represents any one of a hydrogen atom and a substituted or unsubstituted aryl group, and even more preferably each independently represents any one of a hydrogen atom and a substituted or unsubstituted phenyl group.

[0023] Ar 1 bonded to different phenylene rings, Ar2 each other, Ar 3 each other, Ar 4 each other may be the same or different.

[0024] Examples of the alkyl group, aryl group, heterocyclic group, and substituents that these may further have include, for example, R 1 to R 7 and the groups described above, but are not limited thereto.

[0025] <x 1 , x 2 > In General Formulas [1] and [2], one of x 1 , x 2 represents an N atom and the other represents a C atom.

[0026] <n> In general formulas [1] and [2], n represents an integer of 2 or more, preferably an integer of 2 or more and 4 or less.

[0027] Adjacent phenylene groups may be bonded to form a ring. Examples of the compound in which adjacent phenylene groups are bonded to form a ring include, but are not limited to, compounds represented by general formula [6] or [7] described later.

[0028] <Preferred compound> Preferred organic compounds according to this embodiment are shown below, but this embodiment is not limited thereto.

[0029] [Organic compounds represented by general formulas [3] to [5]]

Chemical formula

[0030] In general formula [3], Ar 11 to Ar 18 each independently represents any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

[0031]

Chemical formula

[0032] In general formula [4], Ar 11 to Ar 22 each independently represents any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

[0033]

Chemical formula

[0034] In general formula [5], Ar 11 to Ar 26 Each independently represents any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

[0035] In General Formulas [3] to [5], Ar 11 to Ar 26 Examples of the aryl group, heterocyclic group represented thereby, and substituents that these may further have include, but are not limited to, the groups described by R 1 to R 7 Ar 11 to Ar 26 Each is preferably independently any one of a hydrogen atom and a substituted or unsubstituted aryl group, and more preferably any one of a hydrogen atom, a substituted or unsubstituted phenyl group. Further, it is preferable that adjacent phenylene groups do not bond to form a ring.

[0036] [Organic compound represented by General Formulas [6] to [7]]

Chemical formula

[0037] In General Formula [6], R 8 , R 9 are each independently selected from the groups represented by any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. m represents 1 or 2.

[0038]

Chemical formula

[0039] In General Formula [7], R 8 , R 9 are each independently selected from the groups represented by any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. m represents 1 or 2.

[0040] In general formulas [6] to [7], R 8 , R 9 Examples of the alkyl group, aryl group, heterocyclic group represented by, and the substituent that these may further have include, for example, the groups described for R 1 to R 7 However, it is not limited to these. R 8 , R 9 are preferably a substituted or unsubstituted alkyl group, and more preferably a substituted or unsubstituted methyl group. Further, it is preferable that a phenylene group other than the phenylene group forming the fluorenylene skeleton does not combine with an adjacent phenylene group to form a ring.

[0041] <Feature> The organic compound represented by general formula [1] or [2] has the following features. (1-1) By all the phenylene groups constituting the linking group that links the indolocarbazole skeleton and the pyrimidine skeleton being bonded at the meta position, it has a high T 1 (lowest excited triplet energy), and since ΔST is small, it is excellent in high efficiency, low voltage, and durability. (1-2) Since the HOMO and LUMO orbits are separated, the stability against electrons is improved and it is excellent in durability. (1-3) By all the phenylene groups constituting the linking group that links the indolocarbazole skeleton and the pyrimidine skeleton being bonded at the meta position, it has a low HOMO level and is stable against oxygen, so it is excellent in durability. (1-4) Since the heterocycle bonded via the indolocarbazole skeleton and the linking group is a pyrimidyl group, the dipole moment is improved and it is excellent in durability. Hereinafter, these features will be described.

[0042] (1-1) By all the phenylene groups constituting the linking group that links the indolocarbazole skeleton and the pyrimidine skeleton being bonded at the meta position, it has a high T 1 (lowest excited triplet energy), and since ΔST is small, it is excellent in high efficiency, low voltage, and durability.

[0043] In inventing the organic compound according to the present embodiment, the inventors found that by bonding all the phenylene groups constituting the linking group that bonds the indolocarbazole skeleton and the pyrimidylidene skeleton at the meta-position, high T 1 is achieved and at the same time, ΔST becomes small.

[0044] Here, the calculated values of S 1 and T 1 for the exemplary compounds A1 and B2, which are organic compounds according to the present embodiment, and the comparative compounds 1-a and 1-b, and the ΔST calculated from these are shown in Table 1. Note that the comparative compound 1-a is a compound described in Patent Document 1, and the comparative compound 1-b is a compound described in Patent Document 2.

[0045] In addition, the above calculations were performed using molecular orbital calculations. The calculation method of the molecular orbital calculation method used the density functional theory (DFT), which is currently widely used. The functional was B3LYP, and the basis function was 6-31G * was used. The molecular orbital calculation method was carried out using Gaussian09 (Gaussian09, Revision C.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2010.).

[0046] [Table 1]

[0047] From Table 1, the T of exemplary compounds A1 and B2 1 is both 2.83 eV. On the other hand, the T of comparative compound 1-a 1 is 2.58 eV, and the T of comparative compound 1-b 1 is 2.75 eV. For exemplary compounds A1 and B2 in which all the phenylene groups constituting the linking group connecting the indolocarbazole skeleton and the pyrimidyl skeleton are meta-linked, the T 1 is 0.3 eV higher than that of comparative compound 1-a whose linking group is a dibenzothiophene ring. In comparative compound 1-b whose structure is closer to that of the compound of the present embodiment than comparative compound 1-a, one of the three phenylene groups constituting the linking group has a para-linked structure. It can be seen that for exemplary compounds A1 and B2, the T 1 is 0.08 eV higher.

[0048] Also, regarding ΔST, exemplary compounds A1 and B2 are the smallest, and in particular, when compared with comparative compound 1-b having similar values of S 1 it can be seen that ΔST is smaller.

[0049] Here, the effect due to the small ΔST will be explained. A phosphorescent light-emitting device is an organic light-emitting device that uses T 1 energy for light emission. As a host material used in the light-emitting layer of an organic light-emitting device, it is preferable to have a T 1 energy higher than that of the light-emitting material that emits phosphorescence. This is because when T 1 is high, the energy transfer efficiency to the guest molecules is high, so the device efficiency is improved, and the exciton lifetime is shortened, improving the device durability.

[0050] On the other hand, for an organic compound, when the T 1 energy becomes high, the S 1 energy also tends to become high. A high S 1 energy means a large bandgap.

[0051] In this specification, the band gap indicates the energy difference between HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital).

[0052] When the band gap of the host material of the light-emitting layer is large, the injectability of holes and electrons from the peripheral layer into the light-emitting layer decreases. This leads to an increase in the voltage of the device and a decrease in the device lifetime due to unnecessary charge accumulation, which is not preferable. On the other hand, when the band gap of the host material of the light-emitting layer is small, the injectability of holes and electrons from the peripheral layer into the light-emitting layer improves. As a result, it is possible to reduce the voltage of the device and the decrease in the device lifetime due to unnecessary charge accumulation, which is preferable. Therefore, as the host material used in the light-emitting layer of the organic light-emitting device, an organic compound with high T 1 energy and low S 1 energy, that is, a small ΔST, is preferable.

[0053] Since the compound of this embodiment has a small ΔST, while it is a design with high T 1 it can control the size of S 1 and is a material that can achieve both high efficiency and low voltage.

[0054] (1-2) The separation of the HOMO and LUMO orbits improves the stability against electrons and provides excellent durability.

[0055] The organic compound of this embodiment can be used in the hole transport layer, electron blocking layer, light-emitting layer, and other functional layers of the organic light-emitting device, and can be preferably used as the host of the light-emitting layer in particular. Furthermore, due to the characteristic of high T 1 of the organic compound of the present invention, it can be preferably used as the host of the light-emitting layer in a system that uses a triplet excited state such as phosphorescence or delayed fluorescence for light emission.

[0056] Since the organic compound of this embodiment has an indolocarbazole skeleton, T 1 It has high binding stability and high hole transport performance. On the other hand, since the indolocarbazole skeleton is unstable with respect to electrons, it is preferable that there is an LUMO orbital distribution at a site different from the indolocarbazole skeleton. The organic compound of this embodiment has a pyrimidine skeleton having electron transporting properties. And by bonding the phenylene group constituting the linking group with the indolocarbazole skeleton at the meta position, the LUMO orbital can be distributed only in the pyrimidine skeleton, and the indolocarbazole skeleton can be distributed only in the HOMO orbital.

[0057] Fig. 1 shows the results of visualizing the HOMO and LUMO orbital distributions of the exemplary compound A1 and the comparative compound 1-a of this embodiment by the same calculation method as described above. Also, as the device durability, the luminance degradation rate ratio of the examples using each compound as the host of the organic light-emitting device is shown in Fig. 1 with the device using the comparative compound 1-a as 1.0.

[0058] As shown in Fig. 1, it can be seen that in the exemplary compound A1, only the HOMO orbital is distributed at the site of the indolocarbazole skeleton, and the LUMO orbital is distributed in the pyrimidine skeleton. On the other hand, in the comparative compound 1-a, it can be seen that the LUMO orbital is distributed not only in the pyrimidine skeleton but also in the indolocarbazole skeleton. As a result, the comparative compound 1-a becomes unstable with respect to electrons, so the durability of the device is inferior, and the exemplary compound A1 has separated HOMO and LUMO orbitals, so it has excellent durability.

[0059] (1-3) Since all the phenylene groups constituting the linking group that binds the indolocarbazole skeleton and the pyrimidine skeleton are bonded at the meta position, it has a low HOMO level and is stable with respect to oxygen, so it has excellent durability.

[0060] First, a low HOMO level indicates a level far from the vacuum level. On the other hand, a high HOMO level indicates a level close to the vacuum level.

[0061] As a comparative object, Comparative Compound 1-b, which has a structure closer to that of Exemplary Compound B2 of the present embodiment, was selected. For these two compounds, the calculated values of HOMO, LUMO, and S 1 obtained by the same calculation method as above are shown in Table 2. In addition, as device durability, the luminance degradation rate ratio of the examples using each compound as the host of the organic light-emitting device, when the device using Comparative Compound 1-b is set to 1.0, is shown in Table 2.

[0062]

Table 2

[0063] From Table 2, it can be seen that Exemplary Compound B2 and Comparative Compound 1-b have similar LUMO levels, but the HOMO of Exemplary Compound B2 is 0.16 eV lower. Since the oxidation reaction by oxygen is more likely to be affected as the HOMO level is higher, the compounds of the present embodiment with a lower HOMO level are more stable against oxygen, and as a result, they have excellent durability.

[0064] The differences in the HOMO and LUMO levels can be seen by visualizing the orbital distributions by the same method as above. The results are shown in Figure 2.

[0065] As shown in Figure 2, there is no difference in the orbital distribution of LUMO between the two compounds, but in the orbital distribution of HOMO, Exemplary Compound B2 is localized in the indolocarbazole skeleton. On the other hand, in Comparative Compound 1-b, the HOMO orbitals are distributed up to the two phenylene groups bonded at the para position to the indolocarbazole skeleton. As a result, in Comparative Compound 1-b, by conjugating with the phenylene group bonded at the para position in the linking group, the HOMO orbitals become higher.

[0066] Unlike Comparative Compound 1-b, Exemplary Compound B2 has a structure in which all the phenylene groups of the linking group are bonded at the meta position, and the π-conjugation of the phenylene group is interrupted. Therefore, the distribution of HOMO can be localized in the indolocarbazole skeleton to keep the HOMO level low.

[0067] By having a heterocyclic ring bonded via a linking group to the (1-4) indolocarbazole skeleton be a pyrimidyl group, the dipole moment is improved and the durability is excellent.

[0068] In inventing the organic compound represented by general formula [1] or [2], the present inventors focused on the terminal unit of the molecule (the unit bonded via a linking group to the indolocarbazole skeleton) and the permanent dipole moment.

[0069] Compounds in the organic layer of an organic light-emitting device, particularly in the light-emitting layer, repeatedly transition between the ground state and the excited state during the light-emitting process of the organic light-emitting device. In particular, in an organic phosphorescent light-emitting device, it is important to control the triplet excited state (T 1 ) that accounts for 75% of the excited state. For example, it is necessary to efficiently promote energy transfer from the host molecule's T 1 to the guest molecule and efficiently emit light from the guest molecule. If the energy transfer efficiency is poor, the generated excitation energy has an increased probability of being used for reactions with adjacent molecules, leading to deterioration of the durability characteristics due to the generation of quencher molecules.

[0070] The process of energy transfer from the host molecule's T 1 to the guest molecule is known to occur by Dexter energy transfer. In order to improve the efficiency of Dexter energy transfer, it is important to bring the distance between the host molecule and the guest molecule as close as possible. For this purpose, by arranging a heterocyclic ring that preferably interacts with the metal atom (e.g., iridium atom) of the guest molecule at the end of the molecule, the intermolecular interaction with the guest molecule can be increased and the intermolecular distance can be reduced.

[0071] Since Ir complexes, Pt complexes, etc. are for highly polar guest molecules, in order to enhance the interaction with these molecules, it is preferable for the host molecule to have a high permanent dipole moment to increase the polarity. Since a heterocyclic ring has heteroatoms in its skeleton, it has the characteristics of large polarization and high polarity. As a result of intensive studies, the inventors have found that a pyrimidyl group is suitable as the heterocyclic ring possessed by the terminal portion of the molecule located on the side opposite to the indolocarbazole skeleton in order to reduce the intermolecular distance between the host molecule and the guest molecule.

[0072] Table 3 shows the values of the permanent dipole moment calculated by molecular orbital calculations for the exemplary compound A1 and exemplary compound E1 of this embodiment and the comparative compound 1-c described in Patent Document 2. Further, as device durability, the luminance degradation rate ratio of the examples using each compound as the host of the organic light-emitting device is shown in Table 3 with the device using the comparative compound 1-c as 1.0.

[0073]

Table 3

[0074] Exemplary compounds A1, E1 and comparative compound 1-c all have a high T because the phenylene groups are bonded at the meta position. 1 However, unlike the compounds of this embodiment, the comparative compound 1-c has a triazine skeleton at the terminal portion, so that the dipole moment is low. Different from the pyrimidine skeleton, the triazine skeleton has nitrogen atoms arranged isotropically in the six-membered ring, so this skeleton has a low dipole moment. On the other hand, the pyrimidine skeleton has a high dipole moment because the nitrogen atoms are arranged anisotropically in the six-membered ring. Therefore, since the compounds of this embodiment have a pyrimidine skeleton at the terminal portion, the dipole moment of the whole molecule is improved, so that the polarity of the molecule becomes high. As a result, the interaction with the guest molecule becomes large, efficient energy transfer occurs from the host to the guest, and the durability is improved.

[0075] Furthermore, the organic compound of this embodiment preferably has the following characteristics. (1-5)R 1 or even R 5 At least one of them is a group other than a hydrogen atom, thereby having excellent sublimability.

[0076] In General Formula [1] or [2], when at least one of R 1 or even R 5 is a group other than a hydrogen atom, the symmetry of the molecule decreases and the crystallinity of the molecule decreases, so the sublimation temperature decreases. In addition, since the overlap between the condensed rings in the molecule can be suppressed, the crystallization of the molecule can be suppressed. Therefore, in the organic compound according to the present embodiment, at least one of R 1 or even R 5 is a group other than a hydrogen atom, that is, a group selected from a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a cyano group, and a substituted or unsubstituted alkoxy group. It is preferable that at least one of R 1 or even R 5 is a group selected from a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. When having a group other than a hydrogen atom, it is preferable to have a substituent on the highly planar indolocarbazole skeleton. Specifically, it is preferable that at least one of R 3 R 4 R 5 is a group other than a hydrogen atom, and particularly preferably R 5 is a group other than a hydrogen atom.

[0077] In addition, the group other than a hydrogen atom is preferably a group having a bulkier structure than a hydrogen atom. Specifically, it is preferably a deuterium atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms, and more preferably a methyl group, a tert-butyl group, or a substituted or unsubstituted phenyl group.

[0078] In particular, when having an alkyl group as a group other than a hydrogen atom, the organic compound according to the present embodiment can further suppress the overlap between indolocarbazole skeletons between molecules, and thus is preferable because it has excellent sublimability and excellent film properties. Similarly, when having an aryl group as a group other than a hydrogen atom, especially when having it at the position of R 5 it becomes a steric hindrance group, and the overlap between indolocarbazole skeletons can be further suppressed, so it has excellent sublimability and excellent film properties, and is preferable. Incidentally, even if an aryl group is present at the position of R 5 it does not conjugate with the HOMO orbital, so the HOMO level does not increase and the stability against oxygen remains unchanged and is stable.

[0079] <Specific Examples> Specific examples of the organic compound according to the present embodiment are shown below. However, the present embodiment is not limited thereto.

[0080]

Chemical Formula

[0081]

Chemical Formula

[0082]

Chemical Formula

[0083]

Chemical Formula

[0084]

Chemical Formula

[0085]

Chemical Formula

[0086] [Chemistry]

[0087] [Chemistry]

[0088] [Chemistry]

[0089] [Chemistry]

[0090] [Chemistry]

[0091] [Chemistry]

[0092] [Chemistry]

[0093] [Chemistry]

[0094] [Chemistry]

[0095] [Chemistry]

[0096] [Chemistry]

[0097]

Chem.

[0098] Exemplary compounds belonging to Group A are the compounds represented by n = 2 in formula [1] (compounds represented by formula [3]). Since the compounds in Group A have a small molecular weight and a low sublimation temperature, they have the effect of increasing the margin between the sublimation temperature and the decomposition temperature.

[0099] Exemplary compounds belonging to Group B are the compounds represented by n = 3 in formula [1] (compounds represented by formula [4]). Since they have three phenylene groups bonded at the meta position as the linking group, they have relatively high thermal stability and are characterized by a high T 1 having a high value.

[0100] Exemplary compounds belonging to Group C are the compounds represented by n = 4 in formula [1] (compounds represented by formula [5]). Since they have four phenylene groups bonded at the meta position as the linking group, the rotation sites increase, resulting in a bent structure of the whole molecule and a characteristic that the distance between molecules becomes long. As a result, intermolecular stacking can be avoided, and thus they are excellent in amorphous properties.

[0101] Exemplary compounds belonging to Group D are the compounds represented by formula [6]. As the linking group connecting the indolocarbazole skeleton and the pyrimidine skeleton, having a fluorenylene skeleton in addition to the phenylene group reduces some rotation sites and rigidifies the molecule, which is characterized by an improvement in thermal stability.

[0102] Exemplary compounds belonging to Group E are the compounds represented by n = 2 to 4 in formula [2]. In formula [2], since the indolocarbazole skeleton and the phenylene group of the linking group are bonded at the ortho position, the indolocarbazole skeleton bends with respect to the phenylene group regardless of the number of phenylene groups, resulting in a characteristic that the distance between molecules becomes long. As a result, intermolecular stacking can be avoided, and thus they are excellent in amorphous properties.

[0103] Exemplary compounds belonging to Group F are compounds represented by formula [7]. Similar to Group E, they have a structure in which the indolocarbazole skeleton is bent with respect to the phenylene group. Furthermore, similar to Group D, they are characterized in that some of the rotating sites are reduced to rigidify the molecule and improve the thermal stability.

[0104] (2) Organic light-emitting device Next, the organic light-emitting device of the present embodiment will be described. The organic light-emitting device of the present embodiment has at least 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 the present embodiment, the organic compound layer may be a single layer or a laminate composed of a plurality of layers as long as it has a light-emitting layer. Here, when the organic compound layer is a laminate composed of a plurality of layers, the organic compound layer may have, in addition to the light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole-exciton blocking layer, an electron transport layer, an electron injection layer, etc. The light-emitting layer may be a single layer or a laminate composed of a plurality of layers.

[0105] In the organic light-emitting device of the present embodiment, at least one layer of the organic compound layer contains the organic compound according to the present embodiment. Specifically, the organic compound according to the present embodiment is included in any one of the above-described light-emitting layer, hole injection layer, hole transport layer, electron blocking layer, hole-exciton blocking layer, electron transport layer, electron injection layer, etc. The organic compound according to the present embodiment is preferably included in the light-emitting layer.

[0106] In the organic light-emitting device of the present embodiment, when the organic compound according to the present embodiment is included in the light-emitting layer, the light-emitting layer may be a layer composed only of the organic compound according to the present embodiment, or may be a layer composed of the organic compound according to the present embodiment and other compounds. The light-emitting layer preferably has the organic compound according to the present embodiment and a phosphorescent compound or a hole-transporting compound. Here, when the light-emitting layer is a layer composed of the organic compound according to the present embodiment and other compounds, the organic compound according to the present embodiment may be used as a host of the light-emitting layer, or may be used as a guest. It may also be used as an assist material that can be included in the light-emitting layer. Here, the host is the compound having the largest mass ratio among the compounds constituting the light-emitting layer. The guest is a compound having a mass ratio smaller than that of the host among the compounds constituting the light-emitting layer and is a compound responsible for main emission. The assist material is a compound having a mass ratio smaller than that of the host among the compounds constituting the light-emitting layer and assisting the emission of the guest. Incidentally, the assist material is also called a second host. The guest material can also be called the first compound, and the assist material can be called the second compound. The T 1 of the second compound is preferably 1 equal to or higher than that of the first compound.

[0107] When the organic compound according to the present embodiment is used as a host material of the light-emitting layer, the concentration of the host material is preferably 50% by mass or more and 99% by mass or less, and more preferably 70% by mass or more and 99% by mass or less with respect to the entire light-emitting layer. Further, even when the host material is used at 99% by mass with respect to the entire light-emitting layer, the compound of the present embodiment is a material that is difficult to crystallize, so that it has excellent luminous efficiency and durability. This is due to the structural characteristics of the organic compound according to the present embodiment. Since all the phenylene groups constituting the linking group connecting the indolocarbazole skeleton and the pyrimidine skeleton are bonded at the meta position, the whole molecule has a bent structure. Therefore, the distance between molecules becomes long, and the compound is difficult to aggregate. Even when the organic light-emitting device is driven, crystal grain boundaries associated with molecular aggregation are less likely to occur, and a light-emitting device having excellent luminous efficiency and element lifetime can be provided.

[0108] In addition, the organic compound according to this embodiment may be used as an assist material. An assist material is one that complements the carrier transport property of the host material and plays a role in promoting the injection and movement of carriers into the light-emitting layer. When used as an assist material, it can be used in an amount of 30% by mass or more and 50% by mass or less. In this case, the film properties of the light-emitting layer can also be improved.

[0109] The inventors of the present invention have conducted various studies and found that when the organic compound according to this embodiment is used as the host material or assist material of the light-emitting layer, particularly as the host material of the light-emitting layer, an element can be obtained that exhibits high luminous efficiency, high-brightness light output, and extremely high durability. This light-emitting layer may be a single layer or a multilayer. By making the emission color of this embodiment, for example, blue light emission, and including a light-emitting material having another emission color, it is also possible to mix colors. A multilayer means a state in which a light-emitting layer and another light-emitting layer are laminated. In this case, the emission color of the organic light-emitting device is not limited to blue. More specifically, it may be white or an intermediate color. In the case of white, another light-emitting layer emits a color other than blue, that is, red or green. Also, the film formation method is film formation by evaporation or coating film formation. Details of this will be described in detail in the examples described later.

[0110] The organic compound according to this embodiment can be used as a constituent material of an organic compound layer other than the light-emitting layer constituting the organic light-emitting device of this embodiment. Specifically, it may be used as a constituent material of an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, a hole blocking layer, etc. In this case, the emission color of the organic light-emitting device is not limited to blue. More specifically, it may be white light emission or an intermediate color.

[0111] <Other compounds> In addition to the organic compound according to this embodiment, conventionally known low-molecular and high-molecular hole injection compounds or hole transport compounds, host compounds, light-emitting compounds, electron injection compounds, or electron transport compounds, etc. can be used together as needed. Examples of these compounds are given below.

[0112] As a hole injection and transport material, a material with a high hole mobility is preferred, which facilitates the injection of holes from the anode and transports the injected holes to the light-emitting layer. Also, in order to suppress deterioration of the film quality such as crystallization in the organic light-emitting device, a material with a high glass transition temperature is preferred. Examples of low-molecular-weight and high-molecular-weight materials having hole injection and transport performance include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. Furthermore, the hole injection and transport material is also preferably used for the electron blocking layer. Specific examples of the compounds used as the hole injection and transport material are shown below, but of course, the present invention is not limited thereto.

[0113] [Chemical formula]

[0114] [Chemical formula]

[0115] [Chemical formula]

[0116] Among those listed as hole transport materials, HT16 to HT18 can reduce the driving voltage when used in the layer in contact with the anode. HT16 is widely used in organic light-emitting devices. HT2, HT3, HT4, HT5, HT6, HT10, HT12, and HT15 may be used in the organic compound layer adjacent to HT16. Also, a plurality of materials may be used in one organic compound layer.

[0117] As luminescent materials mainly related to the luminescence function, for example, condensed ring compounds (such as fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, organoaluminum complexes such as tris(8-hydroxyquinolato)aluminum, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, and polymer derivatives such as poly(phenylene vinylene) derivatives, poly(fluorene) derivatives, poly(phenylene) derivatives, etc. can be mentioned. Specific examples of the compounds used as luminescent materials are shown below, but of course, they are not limited to these.

[0118]

Chem.

[0119]

Chem.

[0120]

Chem.

[0121] As the host material or assist material contained in the light-emitting layer, in addition to the compounds of the present embodiment, for example, in addition to aromatic hydrocarbon compounds or their derivatives, carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organoaluminum complexes such as tris(8-hydroxyquinolato)aluminum, organoberyllium complexes, etc. can be mentioned. Specific examples of the compounds used as the light-emitting layer host or light-emitting assist material contained in the light-emitting layer are shown below, but of course, they are not limited to these.

[0122]

Chem.

[0123]

Chem.

[0124]

Chem.

[0125] As an assist material, a compound having a triphenylene skeleton or a carbazole skeleton and excellent hole transport properties is preferable. Among the above specific examples, EM10 to EM14 and EM32 to EM34 are preferable, and EM13 and EM14 are particularly preferable.

[0126] As the electron transport material, it can be arbitrarily selected from those capable of transporting electrons injected from the cathode to the light-emitting layer, and is selected in consideration of the balance with the hole mobility of the hole transport material. Examples of materials having electron transport performance include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organic aluminum complexes, condensed ring compounds (such as fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the electron transport material is also preferably used for the hole blocking layer. Specific examples of the compound used as the electron transport material are shown below, but of course, it is not limited to these.

[0127]

Chem.

[0128]

Chem.

[0129]

Chem.

[0130] As the electron injection material, it can be arbitrarily selected from those that enable easy electron injection from the cathode, and is selected in consideration of the balance with hole injection properties and the like. Organic compounds also include n-type dopants and reducing dopants. For example, compounds containing alkali metals such as lithium fluoride, lithium complexes such as lithium quinolinol, benzimidazolidene derivatives, imidazolidene derivatives, fulvalene derivatives, acridine derivatives, etc. can be mentioned. It can also be used in combination with the above-mentioned electron transport material.

[0131] <Configuration of Organic Light-Emitting Element> The organic light-emitting element is provided by forming a first electrode, an organic compound layer, and a second electrode on a substrate. An insulating layer may be provided on the substrate. A protective layer, a color filter, a microlens, etc. may be provided on the second electrode. When providing a color filter, a planarization layer may be provided between the protective layer. The planarization layer can be composed of an acrylic resin or the like. The same applies when providing a planarization layer between the color filter and the microlens. Either the first electrode or the second electrode may be the anode and the other may be the cathode.

[0132] [Substrate] Examples of the substrate include quartz, glass, silicon wafers, resins, metals, etc. Further, the substrate may be provided with a switching element such as a transistor and wiring thereon, and an insulating layer thereon. As the insulating layer, as long as a contact hole can be formed so that wiring can be formed between the first electrode and insulation from non-connected wiring can be ensured, the material is not limited. For example, resins such as polyimide, silicon oxide, silicon nitride, etc. can be used.

[0133] [Electrode] A pair of electrodes can be used for the electrodes. The pair of electrodes may be an anode and a cathode. When an electric field is applied in the direction in which the organic light-emitting element emits light, the electrode with a higher potential is the anode and the other is the cathode. Also, it can be said that the electrode that supplies holes to the light-emitting layer is the anode and the electrode that supplies electrons is the cathode.

[0134] As the constituent material of the anode, it is preferable to use a material with as large a work function as possible. For example, simple metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, tungsten, etc., mixtures containing these, alloys combining these, metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide, etc. can be used. Also, conductive polymers such as polyaniline, polypyrrole, polythiophene, etc. can be used.

[0135] These electrode materials may be used alone or in combination of two or more. Also, the anode may be composed of a single layer or multiple layers.

[0136] When used as a reflective electrode, for example, chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys thereof, laminated ones, etc. can be used. With the above materials, it is also possible to function as a reflective film without having the role of an electrode. Also, when used as a transparent electrode, oxide transparent conductive layers such as indium tin oxide (ITO), indium zinc oxide, etc. can be used, but it is not limited to these. For the formation of the electrode, photolithography technology can be used.

[0137] On the one hand, as the constituent material of the cathode, those with a small work function are preferable. For example, alkali metals such as lithium, alkaline earth metals such as calcium, simple metals such as aluminum, titanium, manganese, silver, lead, chromium, or mixtures containing these can be mentioned. Alternatively, alloys formed by combining these simple metals can also be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper, zinc-silver, etc. can be used. The use of metal oxides such as indium tin oxide (ITO) is also possible. These electrode materials may be used alone or in combination of two or more kinds. Also, the cathode may have a single-layer structure or a multi-layer structure. Among them, it is preferable to use silver, and in order to reduce the aggregation of silver, it is more preferable to use a silver alloy. As long as the aggregation of silver can be reduced, the ratio of the alloy does not matter. For example, silver: other metals may be 1:1, 3:1, etc.

[0138] The cathode may be a top-emission device using an oxide conductive layer such as ITO, or a bottom-emission device using a reflective electrode such as aluminum (Al), and is not particularly limited. As a method for forming the cathode, although not particularly limited, it is more preferable to use direct current and alternating current sputtering methods, etc., because the film coverage is good and the resistance is easily reduced.

[0139] [Organic compound layer] The organic compound layer may be formed as a single layer or as a plurality of layers. When having a plurality of layers, depending on its function, it may be called a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer. The organic compound layer is mainly composed of an organic compound, but may contain inorganic atoms or inorganic compounds. For example, it may have copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, etc. The organic compound layer may be disposed between the first electrode and the second electrode and may be arranged in contact with the first electrode and the second electrode.

[0140] The organic compound layers (such as hole injection layer, hole transport layer, electron blocking layer, light emitting layer, hole blocking layer, electron transport layer, electron injection layer, etc.) constituting the organic light emitting device according to an embodiment of the present invention are formed by the following method.

[0141] For the organic compound layers constituting the organic light emitting device according to an embodiment of the present invention, dry processes such as vacuum evaporation method, ionization evaporation method, sputtering, and plasma can be used. Instead of the dry process, a wet process can also be used in which the layer is formed by dissolving it in an appropriate solvent and using a known coating method (for example, spin coating method, casting method, microgravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic printing method, offset printing method, inkjet printing method, capillary coating method, nozzle coating method, LB method, etc.). Among them, the vacuum evaporation method, ionization evaporation method, inkjet printing method, nozzle coating method, etc. are suitable for manufacturing large-area organic light emitting devices.

[0142] When a layer is formed by the vacuum evaporation method, solution coating method, etc., crystallization and the like are less likely to occur and the stability over time is excellent. When forming a film by the coating method, a film can also be formed in combination with an appropriate binder resin.

[0143] Examples of the binder resin include, but are not limited to, polyvinyl carbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, urea resin, etc.

[0144] These binder resins may be used alone as a homopolymer or copolymer, or two or more of them may be mixed and used. Further, if necessary, additives such as known plasticizers, antioxidants, and ultraviolet absorbers may be used in combination.

[0145] The thickness of each layer in the organic light-emitting element is usually preferably 1 nm or more and 10 μm or less. In particular, the film thickness of the light-emitting layer of the organic compound layer is preferably 10 nm or more and 100 nm or less in order to obtain effective light-emitting characteristics.

[0146] [Protective layer] A protective layer may be provided on the second electrode. For example, by adhering glass provided with a moisture absorbent on the second electrode, the intrusion of water or the like into the organic compound layer can be reduced, and the occurrence of display defects can be reduced. Further, as another embodiment, a passivation film such as silicon nitride may be provided on the second electrode to reduce the intrusion of water or the like into the organic compound layer. For example, after forming the second electrode, it may be transported to another chamber without breaking the vacuum, and a silicon nitride film with a thickness of 2 μm may be formed by CVD method to serve as a protective layer. A protective layer using atomic layer deposition (ALD method) may be provided after the film formation by CVD method. The material of the film by ALD method is not limited, but may be silicon nitride, silicon oxide, aluminum oxide, etc. Silicon nitride may be further formed by CVD method on the film formed by ALD method. The film by ALD method may have a smaller film thickness than the film formed by CVD method. Specifically, it may be 50% or less, and further 10% or less.

[0147] [Color filter] A color filter may be provided on the protective layer. For example, a color filter considering the size of the organic light-emitting element may be provided on another substrate and bonded to the substrate provided with the organic light-emitting element, or the color filter may be patterned on the above-described protective layer using photolithography technology. The color filter may be composed of a polymer.

[0148] [Planarization layer] A planarization layer may be provided between the color filter and the protective layer. The planarization layer is provided for the purpose of reducing the unevenness of the underlying layer. Without limiting the purpose, it may be called a resin layer in some cases. The planarization layer may be composed of an organic compound, and may be a low molecule or a polymer, but a polymer is preferable.

[0149] The planarization layer may be provided above and below the color filter, and the constituent materials thereof may be the same or different. Specifically, examples include polyvinyl carbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicon resin, urea resin, and the like.

[0150] [Micro lens] The organic light-emitting element may have an optical member such as a micro lens on its light-emitting side. The micro lens can be made of acrylic resin, epoxy resin, or the like. The micro lens may be for the purpose of increasing the amount of light extracted from the organic light-emitting element and controlling the direction of the extracted light. The micro lens may have a hemispherical shape. When having a hemispherical shape, among the tangents in contact with the hemisphere, there is a tangent parallel to the insulating layer, and the contact point between the tangent and the hemisphere is the vertex of the micro lens. The vertex of the micro lens can be determined in the same manner in any cross-sectional view. That is, among the tangents in contact with the semi-circle of the micro lens in the cross-sectional view, there is a tangent parallel to the insulating layer, and the contact point between the tangent and the semi-circle is the vertex of the micro lens.

[0151] Also, the midpoint of the micro lens can be defined. In the cross-section of the micro lens, a line segment from the point where the arc shape ends to the point where another arc shape ends is imagined, and the midpoint of the line segment can be called the midpoint of the micro lens. The cross-section for discriminating the vertex and the midpoint may be a cross-section perpendicular to the insulating layer.

[0152] [Counter substrate] A counter substrate may be provided on the planarization layer. Since the counter substrate is provided at a position corresponding to the aforementioned substrate, it is called a counter substrate. The constituent material of the counter substrate may be the same as that of the aforementioned substrate. When the aforementioned substrate is the first substrate, the counter substrate may be the second substrate.

[0153] [Pixel circuit] An organic light-emitting device having an organic light-emitting element may have a pixel circuit connected to the organic light-emitting element. The pixel circuit may be an active matrix type that independently controls light emission of a first light-emitting element and a second light-emitting element. The active matrix type circuit may be voltage programming or current programming. The driving circuit has a pixel circuit for each pixel. The pixel circuit may have a light-emitting element, a transistor that controls the light emission luminance of the light-emitting element, a transistor that controls the light emission timing, a capacitor that holds the gate voltage of the transistor that controls the light emission luminance, and a transistor for connecting to GND without passing through the light-emitting element.

[0154] The light-emitting device has a display area and a peripheral area arranged around the display area. The display area has a pixel circuit, and the peripheral area has a display control circuit. The mobility of the transistors constituting the pixel circuit may be smaller than the mobility of the transistors constituting the display control circuit. The slope of the current-voltage characteristics of the transistors constituting the pixel circuit may be smaller than the slope of the current-voltage characteristics of the transistors constituting the display control circuit. The slope of the current-voltage characteristics can be measured by so-called Vg-Ig characteristics. The transistors constituting the pixel circuit are transistors connected to a light-emitting element such as a first light-emitting element.

[0155] [Pixel] An organic light-emitting device having an organic light-emitting element may have a plurality of pixels. The pixels have sub-pixels that emit different colors from each other. The sub-pixels may have, for example, light emission colors of RGB respectively.

[0156] Light is emitted from a region called a pixel aperture in the pixel. This region is the same as the first region. The pixel aperture may be 15 μm or less and may be 5 μm or more. More specifically, it may be 11 μm, 9.5 μm, 7.4 μm, 6.4 μm, etc. The distance between sub-pixels may be 10 μm or less, and specifically may be 8 μm, 7.4 μm, 6.4 μm.

[0157] In a plan view, the pixels can take a known arrangement form. For example, it may be a stripe arrangement, a delta arrangement, a pentile arrangement, or a Bayer arrangement. The shape of the sub-pixels in a plan view can be any known shape. For example, it can be a quadrilateral such as a rectangle or a rhombus, a hexagon, etc. Of course, even if it is not an exact figure but has a shape close to a rectangle, it is included in the rectangle. The shape of the sub-pixels and the pixel array can be used in combination.

[0158] <Applications of the organic light-emitting element> The organic light-emitting element according to this embodiment can be used as a component of a display device or a lighting device. Additionally, there are applications such as an exposure light source of an electrophotographic image forming device, a backlight of a liquid crystal display device, and a light-emitting device having a color filter for a white light source.

[0159] The display device may be an image information processing device having an image input unit for inputting image information from an area CCD, a linear CCD, a memory card, etc., an information processing unit for processing the input information, and a display unit for displaying the input image. The display device may have a plurality of pixels, and at least one of the plurality of pixels may have the organic light-emitting element of this embodiment and active elements such as a transistor connected to the organic light-emitting element. At this time, the substrate may be a semiconductor substrate such as silicon, and the transistor may be a MOSFET formed on the substrate. The image display device has an input unit for inputting image information and a display unit for outputting an image, and the display unit has the display device of this embodiment.

[0160] Moreover, the display unit of an imaging device or an inkjet printer may have a touch panel function. The driving method of this touch panel function may be an infrared method, a capacitance method, a resistive film method, or an electromagnetic induction method, and is not particularly limited. Also, the display device may be used for the display unit of a multifunction printer.

[0161] Next, the display device according to this embodiment will be described with reference to the drawings. FIG. 3 is a cross-sectional schematic view showing an example of a display device having an organic light-emitting element and a transistor connected to the organic light-emitting element. The transistor is an example of an active element. The transistor may be a thin-film transistor (TFT).

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

[0163] A transistor and a capacitor element may be arranged in or under the interlayer insulating layer 1. The transistor and the first electrode 2 may be electrically connected via a contact hole or the like (not shown).

[0164] The insulating layer 3 is also called a bank or a pixel isolation film. It covers the end of the first electrode 2 and is arranged surrounding the first electrode 2. The portion where the insulating layer 3 is not arranged is in contact with the organic compound layer 4 and becomes a light-emitting region.

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

[0166] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transmissive electrode. The protective layer 6 reduces the penetration of moisture into the organic compound layer 4. Although the protective layer 6 is shown as a single layer, it may be a plurality of layers. Each layer may have an inorganic compound layer and an organic compound layer.

[0167] The color filter 7 is divided into 7R, 7G, and 7B according to its color. The color filter 7 may be formed on a planarization film (not shown). Further, a resin protection layer (not shown) may be provided on the color filter 7. Also, the color filter 7 may be formed on the protection layer 6. Alternatively, it may be bonded after being provided on a counter substrate such as a glass substrate.

[0168] The display device 100 in FIG. 3(b) has an organic light-emitting element 26 and a TFT 18 which is an example of a transistor. A substrate 11 such as glass or silicon and an insulating layer 12 are provided on the upper part thereof. Active elements such as the TFT 18 are arranged on the insulating layer 12, and a gate electrode 13, a gate insulating film 14, and a semiconductor layer 15 of the active element are provided. The TFT 18 has a drain electrode 16 and a source electrode 17. An insulating film 19 is provided on the upper part of the TFT 18. The anode 21 constituting the organic light-emitting element 26 and the source electrode 17 are connected via a contact hole 20 provided in the insulating film 19.

[0169] Note that the method of electrical connection between the electrodes (anode 21, cathode 23) included in the organic light-emitting element 26 and the electrodes (source electrode 17, drain electrode 16) included in the TFT 18 is not limited to the mode shown in FIG. 3(b). That is, any one of the anode 21 or the cathode 23 and any one of the source electrode 17 or the drain electrode 16 of the TFT 18 may be electrically connected.

[0170] In the display device 100 of FIG. 3(b), the organic compound layer 22 is illustrated as one layer, but the organic compound layer 22 may be a plurality of layers. A first protection layer 24 and a second protection layer 25 for reducing the deterioration of the organic light-emitting element 26 are provided on the cathode 23.

[0171] In the display device 100 of FIG. 3(b), a transistor is used as a switching element, but other switching elements such as a MIM element may be used instead.

[0172] In addition, the transistor used in the display device 100 of FIG. 3(b) is not limited to a thin film transistor having an active layer on the insulating surface of a substrate, and a transistor using a single crystal silicon wafer may also be used. Examples of the active layer include non-single crystal silicon such as single crystal silicon, amorphous silicon, and microcrystalline silicon, and non-single crystal oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Note that a thin film transistor is also called a TFT element.

[0173] The transistor included in the display device 100 of FIG. 3(b) may be formed in a substrate such as an Si substrate. Here, forming in the substrate means manufacturing a transistor by processing the substrate itself such as an Si substrate. That is, having a transistor in the substrate can also be regarded as the substrate and the transistor being integrally formed.

[0174] The organic light emitting element according to this embodiment has its emission luminance controlled by a TFT, which is an example of a switching element, and an image can be displayed by the respective emission luminances by providing the organic light emitting elements in a plurality of planes. Note that the switching element according to this embodiment is not limited to a TFT, and may be a transistor formed of low-temperature polysilicon or an active matrix driver formed on a substrate such as an Si substrate. "On the substrate" can also mean "in the substrate". Whether to provide a transistor in the substrate or use a TFT is selected according to the size of the display portion. For example, if the size is about 0.5 inches, it is preferable to provide the organic light emitting element on the Si substrate.

[0175] FIG. 4 is a schematic diagram showing an example of the display device according to the present embodiment. The display device 1000 may include a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008 between an upper cover 1001 and a lower cover 1009. The touch panel 1003 and the display panel 1005 are connected to flexible printed circuits FPC 1002 and 1004. Transistors are printed on the circuit board 1007. The battery 1008 may not be provided if the display device is not a portable device, or may be provided at another position even if it is a portable device.

[0176] The display device according to the present embodiment may include a color filter having red, green, and blue. The red, green, and blue of the color filter may be arranged in a delta array.

[0177] The display device according to the present embodiment may be used for a display unit of a portable terminal. In that case, it may have both a display function and an operation function. Examples of the portable terminal include mobile phones such as smartphones, tablets, and head-mounted displays.

[0178] The display device according to the present embodiment may be used for a display unit of an imaging device including an optical unit having a plurality of lenses and an imaging element that receives light that has passed through the optical unit. The imaging device may include a display unit that displays information acquired by the imaging element. Further, the display unit may be a display unit exposed to the outside of the imaging device or a display unit disposed in the viewfinder. The imaging device may be a digital camera or a digital video camera.

[0179] FIG. 5(a) is a schematic diagram showing an example of an imaging device according to the present embodiment. The imaging device 1100 may include a viewfinder 1101, a rear display 1102, an operation unit 1103, and a housing 1104. The viewfinder 1101 may include a display device according to the present embodiment. In that case, the display device may display not only the image to be captured but also environmental information, imaging instructions, and the like. The environmental information may include the intensity of external light, the direction of external light, the speed at which the subject moves, the possibility that the subject is blocked by an obstacle, and the like.

[0180] Since the timing suitable for imaging is only a short period of time, it is better to display information as soon as possible. Therefore, it is preferable to use the display device using the organic light emitting element of the present embodiment. This is because the organic light emitting element has a high response speed. The display device using the organic light emitting element requires a high display speed, and these devices can be more suitably used than a liquid crystal display device.

[0181] The imaging device 1100 has an optical unit (not shown). The optical unit has a plurality of lenses and forms an image on an imaging element housed in the housing 1104. The plurality of lenses can adjust the focus by adjusting their relative positions. This operation can also be performed automatically. The imaging device may be called a photoelectric conversion device. The photoelectric conversion device may include, as imaging methods, a method of detecting the difference from a previous image instead of sequentially imaging, a method of cutting out from an image that is always recorded, and the like.

[0182] FIG. 5(b) is a schematic diagram showing an example of an electronic device according to the present embodiment. The electronic device 1200 includes a display unit 1201, an operation unit 1202, and a housing 1203. The housing 1203 may include a circuit, a printed circuit board having the circuit, a battery, and a communication unit. The operation unit 1202 may be a button or a reaction unit of a touch panel system. The operation unit 1202 may be a biometric recognition unit that recognizes a fingerprint and performs unlocking or the like. An electronic device having a communication unit can also be called a communication device. The electronic device 1200 may further have a camera function by including a lens and an imaging device. An image captured by the camera function is displayed on the display unit 1201. Examples of the electronic device 1200 include a smartphone and a notebook computer.

[0183] FIG. 6 is a schematic diagram showing an example of a display device according to the present embodiment. FIG. 6(a) shows a display device such as a TV monitor or a PC monitor. The display device 1300 has a frame 1301 and a display unit 1302. The light-emitting element according to the present embodiment may be used for the display unit 1302. The display device 1300 has a frame 1301 and a base 1303 that supports the display unit 1302. The base 1303 is not limited to the form shown in FIG. 6(a). The lower side of the frame 1301 may also serve as the base. Further, the frame 1301 and the display unit 1302 may be curved. The radius of curvature may be 5000 mm or more and 6000 mm or less.

[0184] FIG. 6(b) is a schematic diagram showing another example of the display device according to the present embodiment. The display device 1310 in FIG. 6(b) is configured to be foldable and is a so-called foldable display device. The display device 1310 includes a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may have the light-emitting element according to the present embodiment. The first display unit 1311 and the second display unit 1312 may be a single seamless display device. The first display unit 1311 and the second display unit 1312 can be separated at the bending point. The first display unit 1311 and the second display unit 1312 may display different images, or may display one image together with the first and second display units.

[0185] FIG. 7(a) is a schematic diagram showing an example of the lighting device according to the present embodiment. The lighting device 1400 may include a housing 1401, a light source 1402, a circuit board 1403, an optical filter 1404 that transmits light emitted by the light source 1402, and a light diffusing portion 1405. The light source 1402 may include an organic light emitting element according to the present embodiment. The optical filter 1404 may be a filter that improves the color rendering property of the light source. The light diffusing portion 1405 can effectively diffuse the light of the light source, such as lighting up, and deliver the light to a wide range. The optical filter 1404 and the light diffusing portion 1405 may be provided on the light emitting side of the illumination. If necessary, a cover may be provided on the outermost side.

[0186] The lighting device is, for example, a device that illuminates an interior. The lighting device may emit any color from white, day white, or other blue to red. It may have a dimming circuit for dimming them or a color mixing circuit for mixing the emission colors. The lighting device may include the organic light emitting element of the present embodiment and a power supply circuit connected thereto. The power supply circuit is a circuit that converts an AC voltage into a DC voltage. The lighting device may include an inverter circuit. Also, white means a color temperature of 4200K and day white means a color temperature of 5000K. The lighting device may include a color filter.

[0187] Further, the lighting device according to the present embodiment may include a heat radiating portion. The heat radiating portion releases the heat inside the device to the outside of the device, and examples thereof include a metal having a high specific heat and liquid silicon.

[0188] FIG. 7(b) is a schematic diagram of an automobile, which is an example of a moving body according to the present embodiment. The automobile has a tail lamp, which is an example of a lamp. The automobile 1500 may have a tail lamp 1501 and may be configured to turn on the tail lamp when a braking operation or the like is performed.

[0189] The tail lamp 1501 may have the organic light-emitting element according to this embodiment. The tail lamp 1501 may have a protective member for protecting the organic light-emitting element. The protective member has a certain degree of strength and may be made of any material as long as it is transparent, but is preferably made of polycarbonate or the like. A phthalic acid derivative, an acrylonitrile derivative, or the like may be mixed into the polycarbonate.

[0190] The vehicle 1500 may have a vehicle body 1503 and a window 1502 attached thereto. The window 1502 may be a transparent display as long as it is not a window for checking the front and rear of the vehicle. The transparent display may have the organic light-emitting element according to this embodiment. In this case, constituent materials such as electrodes of the organic light-emitting element are made of transparent members.

[0191] The moving body according to this embodiment may be a ship, an aircraft, a drone, or the like. The moving body may have a fuselage and a lighting fixture provided on the fuselage. The lighting fixture may emit light for notifying the position of the fuselage. The lighting fixture has the organic light-emitting element according to this embodiment.

[0192] Referring to FIG. 8, application examples of the display device of each of the above embodiments will be described. The display device can be applied to a system that can be worn as a wearable device such as, for example, smart glasses, an HMD, or smart contacts. The imaging display device used in such an application example has an imaging device capable of photoelectrically converting visible light and a display device capable of emitting visible light.

[0193] FIG. 8(a) is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention. Using FIG. 8(a), glasses 1600 (smart glasses) according to one application example will be described. An imaging device 1602 such as a CMOS sensor or a SPAD is provided on the front surface side of the lens 1601 of the glasses 1600. Further, on the back surface side of the lens 1601, the display device of each of the above-described embodiments is provided.

[0194] The glasses 1600 further include a control device 1603. The control device 1603 functions as a power source that supplies power to the imaging device 1602 and the display device. Also, the control device 1603 controls the operations of the imaging device 1602 and the display device. An optical system for condensing light onto the imaging device 1602 is formed in the lens 1601.

[0195] FIG. 8(b) is a schematic diagram showing another example of the wearable device according to an embodiment of the present invention. Using FIG. 8(b), glasses 1610 (smart glasses) according to one application example will be described. The glasses 1610 have a control device 1612, and an imaging device corresponding to the imaging device 1602 in FIG. 8(a) and a display device are mounted on the control device 1612. An optical system for the imaging device within the control device 1612 and for projecting light emitted from the display device is formed in the lens 1611, and an image is projected onto the lens 1611. The control device 1612 functions as a power source that supplies power to the imaging device and the display device, and controls the operations of the imaging device and the display device.

[0196] The control device 1612 may have a gaze detection unit that detects the wearer's gaze. Infrared rays may be used for gaze detection. The infrared light emitting unit emits infrared light toward the eyes of the user who is gazing at the display image. An imaging unit having a light receiving element detects the reflected light of the emitted infrared light from the eyes, thereby obtaining an imaging image of the eyes. By having a reducing means for reducing the light from the infrared light emitting unit to the display unit in a plan view, a decrease in image quality is reduced. The user's gaze with respect to the display image is detected from the imaging image of the eyes obtained by imaging the infrared light. Any known method can be applied to gaze detection using the imaging image of the eyes. As an example, a gaze detection method based on a Purkinje image by reflection of irradiation light on the cornea can be used. More specifically, gaze detection processing based on the pupil corneal reflection method is performed. Based on the image of the pupil and the Purkinje image included in the imaging image of the eyes using the pupil corneal reflection method, a gaze vector representing the orientation (rotation angle) of the eyes is calculated, thereby detecting the user's gaze.

[0197] A display device according to an embodiment of the present invention includes an imaging device having a light receiving element, and may control a display image of the display device based on user's line-of-sight information from the imaging device. Specifically, the display device determines, based on the line-of-sight information, a first field-of-view region that the user is gazing at and a second field-of-view region other than the first field-of-view region. The first field-of-view region and the second field-of-view region may be determined by a control device of the display device, or the display device may receive those determined by an external control device. In the display area of the display device, the display resolution of the first field-of-view region may be controlled to be higher than the display resolution of the second field-of-view region. That is, the resolution of the second field-of-view region may be made lower than that of the first field-of-view region.

[0198] Further, the display area has a first display area and a second display area different from the first display area, and based on the line-of-sight information, a region with a higher priority is determined from the first display area and the second display area. The first field-of-view region and the second field-of-view region may be determined by a control device of the display device, or the display device may receive those determined by an external control device. The resolution of the region with a higher priority may be controlled to be higher than the resolution of the region other than the region with a higher priority. That is, the resolution of the region with a relatively lower priority may be made lower.

[0199] Note that AI may be used to determine the first field-of-view region or the region with a higher priority. AI may be a model configured to estimate the angle of the line of sight and the distance to the object at the tip of the line of sight from an image of the eyeball, using the image of the eyeball and the direction in which the eyeball in the image is actually looking as teacher data. The AI program may be possessed by the display device, the imaging device, or an external device. When an external device possesses it, it is transmitted to the display device via communication.

[0200] When performing display control based on visual recognition detection, it is preferably applicable to smart glasses further having an imaging device for imaging the outside. The smart glasses can display the imaged external information in real time.

[0201] FIG. 9(a) is a schematic diagram showing an example of an image forming apparatus according to an embodiment of the present invention. The image forming apparatus 40 is an electrophotographic image forming apparatus, and includes a photoreceptor 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transferrer 32, a conveyance roller 33, and a fixing unit 35. Light 29 is irradiated from the exposure light source 28, and an electrostatic latent image is formed on the surface of the photoreceptor 27. This exposure light source 28 has an organic light emitting element according to the present embodiment. The developing unit 31 has toner or the like. The charging unit 30 charges the photoreceptor 27. The transferrer 32 transfers the developed image onto a recording medium 34. The conveyance roller 33 conveys the recording medium 34. The recording medium 34 is, for example, paper. The fixing unit 35 fixes the image formed on the recording medium 34.

[0202] FIGS. 9(b) and 9(c) are diagrams showing the exposure light source 28, and are schematic diagrams showing a state in which a plurality of light emitting portions 36 are arranged on a long substrate. An arrow 37 is a direction parallel to the axis of the photoreceptor, and represents the column direction in which the organic light emitting elements are arranged. This column direction is the same as the direction of the axis around which the photoreceptor 27 rotates. This direction can also be referred to as the major axis direction of the photoreceptor 27. FIG. 9(b) shows a form in which the light emitting portions 36 are arranged along the major axis direction of the photoreceptor 27. FIG. 9(c) shows a form different from that of FIG. 9(b), in which the light emitting portions 36 are alternately arranged in the column direction in each of the first column and the second column. The first column and the second column are arranged at different positions in the row direction. In the first column, a plurality of light emitting portions 36 are arranged at intervals. The second column has light emitting portions 36 at positions corresponding to the intervals between the light emitting portions 36 in the first column. That is, also in the row direction, a plurality of light emitting portions 36 are arranged at intervals. The arrangement in FIG. 9(c) can also be described as, for example, a state of being arranged in a grid pattern, a state of being arranged in a staggered grid, or a checkered pattern.

[0203] As described above, by using the apparatus using the organic light emitting element according to the present embodiment, it is possible to obtain a good image quality and a stable display even for a long-time display. Further, by using the apparatus using the organic light emitting element according to the present embodiment, it is possible to achieve both good visibility outdoors with a high-efficiency and high-brightness light output and power-saving display.

[0204] <<Included Structures>> The disclosure of this embodiment includes the following structures. (Structure 1) An organic compound characterized by being represented by General Formula [1] or [2]. In General Formulas [1] and [2], R 1 to R 7 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a cyano group, and a substituted or unsubstituted alkoxy group. Ar 1 to Ar 4 each independently represents any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. x 1 , x 2 One of them represents an N atom and the other represents a C atom. n represents an integer of 2 or more, and adjacent phenylene groups may be bonded to form a ring. (Structure 2) The organic compound according to Structure 1, wherein at least one of the above R 1 to R 5 is a group selected from a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. (Structure 3) The organic compound according to Structure 2, wherein at least one of the above R 3 to R 5 is a group selected from a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. (Structure 4) The organic compound according to Structure 3, wherein the above R 5 is a group selected from a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

[0205] (Constitution 5) The organic compound according to any one of Constitutions 1 to 4, characterized in that it is represented by the following general formula [3]. In the general formula [3], Ar 11 to Ar 18 each independently represents any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. (Constitution 6) The organic compound according to any one of Constitutions 1 to 4, characterized in that it is represented by the following general formula [4]. In the general formula [4], Ar 11 to Ar 22 each independently represents any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. (Constitution 7) The organic compound according to any one of Constitutions 1 to 4, characterized in that it is represented by the following general formula [5]. In the general formula [5], Ar 11 to Ar 26 each independently represents any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. (Constitution 8) The organic compound according to any one of Constitutions 1 to 4, characterized in that it is represented by the following general formula [6]. In the general formula [6], R 8 , R 9 are each independently selected from the groups represented by any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. m represents 1 or 2. (Constitution 9) The organic compound according to any one of Constitutions 1 to 4, characterized in that it is represented by the following general formula [7]. In the general formula [7], R 8 , R 9 It is independently selected from groups represented by any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. m represents 1 or 2.

[0206] (Configuration 10) In an organic light-emitting device having a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, at least one layer of the organic compound layer contains the organic compound according to any one of Configurations 1 to 9. An organic light-emitting device characterized by the above. (Configuration 11) The organic compound layer has a light-emitting layer, and the light-emitting layer has the organic compound. The organic light-emitting device according to Configuration 10, characterized by the above. (Configuration 12) The light-emitting layer further has a phosphorescent compound. The organic light-emitting device according to Configuration 11, characterized by the above. (Configuration 13) The light-emitting layer further has a hole-transporting compound. The organic light-emitting device according to Configuration 12, characterized by the above. (Configuration 14) It further has another light-emitting layer disposed laminated with the light-emitting layer, and the other light-emitting layer emits light of a color different from the light-emitting color emitted by the light-emitting layer. The organic light-emitting device according to Configuration 11 or 12, characterized by the above. (Configuration 15) The organic light-emitting device according to Configuration 14, characterized by emitting white light.

[0207] (Configuration 16) It has a plurality of pixels, and at least one of the plurality of pixels has an organic light-emitting device according to any one of Configurations 10 to 15 and a transistor connected to the organic light-emitting device. A display device characterized by the above. (Configuration 17) It has an optical unit having a plurality of lenses, an imaging element that receives light that has passed through the optical unit, and a display unit that displays an image captured by the imaging element. The photoelectric conversion device is characterized in that the display unit has the organic light-emitting element described in any one of Configurations 10 to 15. (Configuration 18) An electronic device, comprising: a display unit having the organic light-emitting element described in any one of Configurations 10 to 15; a housing provided with the display unit; and a communication unit provided in the housing and communicating with the outside. (Configuration 19) An illumination device, comprising: a light source having the organic light-emitting element described in any one of Configurations 10 to 15; and a light diffusing unit or an optical filter that transmits light emitted by the light source. (Configuration 20) A moving body, comprising: a lighting fixture having the organic light-emitting element described in any one of Configurations 10 to 15; and a body provided with the lighting fixture. (Configuration 21) An image forming apparatus, comprising: a photoreceptor; and an exposure light source that exposes the photoreceptor, wherein the exposure light source has the organic light-emitting element described in any one of Configurations 10 to 15.

Examples

[0208] Hereinafter, the present invention will be described by way of examples. However, the present invention is not limited thereto.

[0209] [Example 1 (Synthesis of Exemplary Compound A1)]

Chemical formula

[0210] (1) Synthesis of Compound M3 The following reagents and solvents were charged into a 3 L eggplant flask. Compound M1: 71.1 g (425 mmol) Compound M2: 98.0 g (468 mmol) Sodium tert-butoxide: 61.3 g (638 mmol) Dehydrated DMAc: 1.4 L Next, the reaction solution was heated to 100 °C under a nitrogen stream and stirred at this temperature (100 °C) for 1 hour. After completion of the reaction, it was poured into 1.5 L of water and extracted twice with 1.5 L of ethyl acetate. The combined organic layers were washed with 1.0 L of saturated brine and dried over anhydrous sodium sulfate. This solution was concentrated to obtain 218 g of a white-brown solid. This solid was dispersed and washed with 600 mL of ethanol at about 5 °C and then dried under reduced pressure at 80 °C to obtain 127 g (yield 84%) of a white solid compound M3.

[0211] (2) Synthesis of compound M4 A 3 L eggplant flask was charged with the following reagents and solvents. Compound M3: 126 g (353 mmol) 1,8-Diazabicyclo[5.4.0]undec-7-ene: 161 g (353 mmol) Dehydrated DMAc: 1.8 L Next, after degassing the reaction solution, 7.44 g (10.6 mmol) of bis(triphenylphosphine)palladium(II) dichloride was added. This reaction solution was stirred overnight at an internal temperature of 130 °C and further stirred at 140 °C for 2 hours, and then disappearance of the starting compound M3 was confirmed. After allowing this brown suspension to cool, it was poured into 3.0 L of water, and the precipitated grayish-white solid was collected by filtration. This solid was dispersed and washed with 1.0 L of methanol, and after drying, 97 g of a grayish-white solid was obtained. This grayish-white solid was filtered through silica gel (SiO 2 : 400 g, NH-SiO 2 : 200 g, developing solvent: toluene at about 80 °C), and then concentrated to obtain 96 g of a white solid. Further, this white solid was heated and suspended and washed with 600 mL of ethanol, then collected by filtration and dried under reduced pressure at 80 °C to obtain 86 g (yield 88%) of a white solid compound M4.

[0212] (3) Synthesis of compound M5 A 2 L eggplant flask was charged with the following reagents and solvents. Compound M4: 40.0 g (145 mmol) Bis(pinacolato)diboron: 10.3 g (319 mmol) Pd(OAc) 2 : 1.60 g (7.23 mmol) s-phos: 8.90 g (21.8 mmol) Potassium acetate: 35.6 g (363 mmol) Toluene: 800 mL Next, the reaction solution was heated to 110 °C under a nitrogen stream and stirred at this temperature (110 °C) for 2 hours. After completion of the reaction, it was cooled to an internal temperature of 55 °C, filtered while hot through celite, concentrated, washed twice by dispersion with 500 mL of methanol, and dried under reduced pressure to obtain 39 g (yield: 73%) of white compound M5.

[0213] (4) Synthesis of compound M7 A 2 L eggplant flask was charged with the following reagents and solvents. Compound M5: 35 g (95.3 mmol) Compound M6: 25 g (93.4 mmol) Pd(PPh 3 ) 4 : 1.07 g (0.93 mmol) Sodium carbonate: 14.9 g (140 mmol) Toluene: 500 ml Ethanol: 250 ml Water: 250 ml Next, the reaction solution was heated to 75 °C under a nitrogen stream and stirred at this temperature (75 °C) for 3 hours. After completion of the reaction, extraction was performed with toluene and water, then 75 g of silica gel was added to the filtrate and stirred at room temperature for 1 hour, the silica gel was filtered off, and the filtrate was concentrated. 75 g of toluene and 150 g of heptane were added to the concentrated slurry for recrystallization, and this was repeated twice. After drying under reduced pressure, 31 g (yield: 77%) of white compound M7 was obtained.

[0214] (5) Synthesis of compound M8 A 2 L eggplant flask was charged with the following reagents and solvents. Compound M7: 30.0 g (70.1 mmol) Bis(pinacolato)borane: 39.2 g (154 mmol) Palladium(II) acetate: 0.79 g (3.51 mmol) SPhos: 4.32 g (10.5 mmol) Potassium acetate: 17.2 g (175 mmol) Toluene: 900 mL Next, the reaction solution was heated to 110 °C under a nitrogen stream and stirred at this temperature (110 °C) for 4 hours. After completion of the reaction, it was cooled to an internal temperature of 80 °C, hot filtration was carried out with celite, concentrated, dispersion washing was carried out twice with 500 mL of methanol, and after drying under reduced pressure, 27 g (yield: 75%) of white compound M8 was obtained.

[0215] (6) Synthesis of Exemplary Compound A1 The following reagents and solvents were charged into a 500 mL eggplant flask. Compound M8: 5.00 g (9.62 mmol) Compound M9: 2.57 g (9.62 mmol) Pd(OAc) 2 : 0.11 g (0.48 mmol) s-phos: 0.59 g (1.44 mmol) Tripotassium phosphate: 4.08 g (19.2 mmol) Toluene: 250 mL Water: 25 mL Next, the reaction solution was heated to 100 °C under a nitrogen stream and stirred at this temperature (100 °C) for 4 hours. After completion of the reaction, 100 mL of methanol was added, stirred at room temperature for 30 minutes, and then filtered. This was purified by silica gel column chromatography (chlorobenzene) and then dispersion washing was carried out with heptane / toluene to obtain 5.70 g (yield: 65%) of white exemplary compound A1.

[0216] Mass spectrometry was performed on the exemplary compound A1 using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker). [MALDI-TOF-MS] Measured value: m / z = 623 Calculated value: C 46 H 29 N 3 = 623

[0217] [Examples 2 to 26 (Synthesis of Exemplary Compounds)] As shown in Tables 4 to 9, exemplified compounds were synthesized in the same manner as in Example 1, except that raw material M1 of Example 1 was changed to raw material 1, raw material M2 to raw material 2, raw material M6 to raw material 3, and raw material M9 to raw material 4. Also shown are the measured values of m / z in the mass spectrometry results measured in the same manner as in Example 1.

[0218]

Table 4

[0219]

Table 5

[0220]

Table 6

[0221]

Table 7

[0222]

Table 8

[0223]

Table 9

[0224] [Example 27] An organic light-emitting device with a bottom emission structure in which an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode were sequentially formed on a substrate was fabricated.

[0225] First, ITO was deposited on a glass substrate, and an ITO electrode (anode) was formed by performing a desired patterning process. At this time, the film thickness of the ITO electrode was set to 100 nm. The substrate on which the ITO electrode was thus formed was used as an ITO substrate in the following steps. Next, 1.33×10 -4 Vacuum evaporation by resistance heating was carried out in a vacuum chamber of Pa, and an organic compound layer and an electrode layer shown in Table 10 were continuously formed on an ITO substrate. At this time, the electrode area of the opposing electrode (metal electrode layer, cathode) was 3 mm 2 was made to be.

[0226]

Table 10

[0227] For the obtained device, the characteristics of the device were measured and evaluated. The maximum external quantum efficiency (E.Q.E.) of the light-emitting device was 13%. Furthermore, a continuous drive test was carried out at a current density of 100 mA / cm 2 , and the time when the luminance degradation rate reached 5% was measured. When the time when the luminance degradation rate of Comparative Example 2 reached 5% was taken as 1.0, the luminance degradation rate ratio of this Example was 1.3. These results are shown in Table 11.

[0228] In this Example, the current-voltage characteristics were measured with a microammeter 4140B manufactured by Hewlett-Packard Company, and the emission luminance was measured with a BM7 manufactured by Topcon Corporation.

[0229] [Examples 28 to 41, Comparative Examples 1 to 3] An organic light-emitting device was fabricated in the same manner as in Example 27 except that the compound shown in Table 11 was appropriately changed. For the obtained device, the characteristics of the device were measured and evaluated in the same manner as in Example 27. The measurement results are shown in Table 11.

[0230]

Table 11

[0231] From Table 11, the maximum external quantum efficiencies (E.Q.E.) of Comparative Examples 1 to 2 were 10% and 11% respectively, and the light-emitting device according to this embodiment was superior in light-emitting efficiency. This is because the exemplary compound according to this embodiment has a high T as described in the above characteristic (1-1) 1 This is because it has [the relevant property]. Also, in all aspects, the light-emitting element according to this embodiment was superior in element lifetime to the comparative example. This is because the organic compound according to this embodiment satisfied the above-described features (1-2) to (1-4), resulting in improved durability.

[0232] [Example 42] An organic light-emitting element was fabricated in the same manner as in Example 27, except that the organic compound layer and the electrode layer shown in Table 12 were continuously formed.

[0233]

Table 12

[0234] For the obtained element, the characteristics of the element were measured and evaluated in the same manner as in Example 27. The maximum external quantum efficiency (E.Q.E.) of the light-emitting element was 15%. Further, when the time when the luminance degradation rate of Example 33 reached 5% was set to 1.0, the luminance degradation rate ratio of this example was 1.2. These results are shown in Table 13. In addition, the results of Example 33 are also shown in Table 13 for comparison.

[0235] [Examples 43 to 48] An organic light-emitting element was fabricated in the same manner as in Example 42, except that the compound shown in Table 13 was appropriately changed. For the obtained element, the characteristics of the element were measured and evaluated in the same manner as in Example 42. The measurement results are shown in Table 13. For comparison, the results of Example 33 are also shown in Table 13.

[0236]

Table 13

[0237] As shown in Table 13, when the compound of this embodiment is used together with an assist material, the maximum external quantum efficiency is improved by suppressing the leakage of holes and electrons to the layers around the light-emitting layer, and furthermore, the durability is improved by eliminating the carrier accumulation at the interface between the light-emitting layer and the surrounding layers.

[0238] As described above, by using the organic compound according to the present embodiment, a light-emitting device excellent in luminous efficiency and device lifetime can be provided.

Explanation of symbols

[0239] 1: Interlayer insulating layer, 2: First electrode, 3: Insulating layer, 4: Organic compound layer, 5: Second electrode, 6: Protection layer, 7: Color filter, 10: Sub-pixel, 11: Substrate, 12: Insulating layer, 13: Gate electrode, 14: Gate insulating film, 15: Semiconductor layer, 16: Drain electrode, 17: Source electrode, 18: TFT, 19: Insulating film, 20: Contact hole, 21: Anode, 22: Organic compound layer, 23: Cathode, 24: First protection layer, 25: Second protection layer, 26: Organic light-emitting device, 100: Display device< / n>

Claims

1. An organic compound characterized by being represented by the following general formula [1] or [2]. [Chemical 1] In general formulas [1] and [2], R 1 to R 7 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a cyano group, and a substituted or unsubstituted alkoxy group. Ar 1 to Ar 4 each independently represents any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. x 1 , x 2 One of them represents an N atom, and the other represents a C atom. n represents an integer of 2 or more, and adjacent phenylene groups may be bonded to form a ring.

2. Said R 1 to R 5 At least one of which is a group selected from a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, the organic compound according to claim 1.

3. Said R 3 to R 5 At least one of which is a group selected from a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. The organic compound according to claim 2, characterized in that.

4. Said R 5 is a group selected from a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, the organic compound according to claim 3.

5. The organic compound according to any one of Claims 1 to 4, characterized by being represented by the following general formula [3]. [Chemical 2] In general formula [3], Ar 11 to Ar 18 each independently represents any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

6. The organic compound according to any one of Claims 1 to 4, characterized by being represented by the following general formula [4]. 【Chemical Formula 3】 In general formula [4], Ar 11 to Ar 22 each independently represents any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

7. The organic compound according to any one of Claims 1 to 4, characterized by being represented by the following general formula [5]. 【Chemical Formula 4】 In general formula [5], Ar 11 to Ar 26 each independently represents any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

8. The organic compound according to any one of Claims 1 to 4, characterized by being represented by the following general formula [6]. [Chemical Formula 5] In the general formula [6], R 8 , R 9 is independently selected from the groups represented by any one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, respectively. m represents 1 or 2.

9. The organic compound according to any one of Claims 1 to 4, characterized by being represented by the following general formula [7]. 【Chemical Formula 6】 In the general formula [7], R 8 , R 9 is independently selected from the groups represented by any of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, respectively. m represents 1 or 2.

10. In an organic light-emitting device having a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, at least one layer of the organic compound layer contains the organic compound according to any one of Claims 1 to 4. An organic light-emitting device characterized by this.

11. The organic light-emitting device according to Claim 10, wherein the organic compound layer has a light-emitting layer, and the light-emitting layer has the organic compound.

12. The organic light-emitting device according to Claim 11, wherein the light-emitting layer further has a phosphorescent compound.

13. The organic light-emitting device according to Claim 12, wherein the light-emitting layer further has a hole-transporting compound.

14. The organic light-emitting device according to Claim 11, further having another light-emitting layer disposed laminated with the light-emitting layer, and the other light-emitting layer emits light of a color different from the light-emitting color emitted by the light-emitting layer.

15. The organic light-emitting device according to Claim 14, characterized by emitting white light.

16. A display device having a plurality of pixels, wherein at least one of the plurality of pixels has the organic light-emitting device according to Claim 10 and a transistor connected to the organic light-emitting device.

17. An optical unit having a plurality of lenses, an imaging element that receives light that has passed through the optical unit, and a display unit that displays an image captured by the imaging element. The photoelectric conversion device, wherein the display unit has the organic light-emitting device according to Claim 10.

18. An electronic device, comprising: a display unit having the organic light-emitting element according to claim 10; a housing provided with the display unit; and a communication unit provided in the housing and communicating with the outside.

19. An illumination device, comprising: a light source having the organic light-emitting element according to claim 10; and a light diffusing unit or an optical filter that transmits light emitted from the light source.

20. A moving body, comprising: a lighting fixture having the organic light-emitting element according to claim 10; and a body provided with the lighting fixture.

21. An image forming apparatus, comprising: a photoreceptor; and an exposure light source that exposes the photoreceptor, wherein the exposure light source has the organic light-emitting element according to claim 10.

Images