Organic compounds and organic light-emitting devices

Abstract

This invention provides organic compounds with excellent luminescence efficiency and color purity. [Solution] An organic compound characterized by being represented by the general formula [1]. TIFF2026092656000052.tif5392 In the general formula [1], R1 to R 27 R is a hydrogen atom or various substituents. 21 and R 24 , and, R 22 and R 27 At least one of them may be bonded to form a ring. Ar is a substituted or unsubstituted aryl group. n is an integer between 1 and 5.

Description

[Technical Field]

[0001] This invention relates to organic compounds and organic light-emitting devices using the same. [Background technology]

[0002] An organic light-emitting element (hereinafter sometimes referred to as an "organic electroluminescent element" or "organic EL element") is an electronic element having a pair of electrodes and an organic compound layer placed between these electrodes. By injecting electrons and holes from this pair of electrodes, excitons of the light-emitting organic compound in the organic compound layer are generated, and when these excitons return to the ground state, the organic light-emitting element emits light.

[0003] Recent advances in organic light-emitting devices are remarkable, enabling low drive voltage, diverse emission wavelengths, fast response times, and miniaturization and weight reduction of light-emitting devices.

[0004] Regarding the improvement of the efficiency of light-emitting devices, devices using high-efficiency materials such as phosphorescent materials and delayed fluorescence materials have been reported.

[0005] As compounds created to date, Patent Document 1 describes Compound 1-a below. Patent Document 2 describes Compound 2-a below. These compounds are based on acenaphtho[1,2-k]benzo[e]acephenanthlene as their basic structure.

[0006] [ka] [Prior art documents] [Patent Documents]

[0007] [Patent Document 1] Japanese Patent Publication No. 2010-270103 [Patent Document 2] International Publication No. 2017 / 146192 [Overview of the Initiative] [Problems that the invention aims to solve]

[0008] However, compound 1-a has a structure that makes it difficult for the compounds to orient themselves horizontally, so there is room for improvement in terms of luminescence efficiency. Also, compound 2-a has a long conjugation length, so there is room for improvement in terms of color purity.

[0009] This invention has been made in view of the above problems, and its purpose is to provide an organic compound with excellent luminescence efficiency and color purity. [Means for solving the problem]

[0010] The organic compound according to the present invention is characterized by being represented by the general formula [1].

[0011] [ka]

[0012] In the general formula [1], R1 to R 27 Each of these is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted amino group, and a cyano group. 21 and R 24 , and, R 22 and R 27 At least one of them may be joined to form a ring.

[0013] Ar is a substituted or unsubstituted aryl group.

[0014] n is an integer between 1 and 5 (inclusive).

[0015] L is represented by General Formulas [2] to [7], or a combination thereof. When n is an integer of 2 or more, the plurality of Ls may be the same or different.

[0016]

Chemical Formula

[0017] In General Formulas [2] to [7], R 101 to R 138 、R a 、and R b are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aryl group. R a and R b may combine to form a ring. X is an oxygen atom or a sulfur atom. * is a bonding position.

Advantages of the Invention

[0018] According to the present invention, an organic compound excellent in luminous efficiency and color purity can be provided.

Brief Description of the Drawings

[0019] [Figure 1] (a) It is a schematic cross-sectional view showing an example of a pixel of a display device according to an embodiment of the present invention. (b) It is a schematic cross-sectional view of an example of a display device using an organic EL element according to an embodiment of the present invention. [Figure 2] It is a schematic diagram showing an example of a display device according to an embodiment of the present invention. [Figure 3] (a) It is a schematic diagram showing an example of an imaging device according to an embodiment of the present invention. (b) It is a schematic diagram showing an example of an electronic device according to an embodiment of the present invention. [Figure 4] (a) It is a schematic diagram showing an example of a display device according to an embodiment of the present invention. (b) It is a schematic diagram showing an example of a foldable display device. [Figure 5](a) A schematic diagram showing an example of a lighting device according to one embodiment of the present invention. (b) A schematic diagram showing an example of an automobile having a vehicle light fixture according to one embodiment of the present invention. [Figure 6] (a) A schematic diagram showing an example of a wearable device according to one embodiment of the present invention. (b) A schematic diagram showing an example of a wearable device according to one embodiment of the present invention, which includes an imaging device. [Figure 7] (a) A schematic diagram showing an example of an image forming apparatus according to one embodiment of the present invention. (b) A schematic diagram showing an example of an exposure light source for an image forming apparatus according to one embodiment of the present invention. (c) A schematic diagram showing an example of an exposure light source for an image forming apparatus according to one embodiment of the present invention. [Figure 8] This figure shows the transition dipole moment direction and emission direction of an organic compound. [Figure 9] This figure shows the HOMO orbital distributions of example compound A1 and comparative compound 2-a. [Figure 10] This figure shows the HOMO orbital distributions of example compounds A26, B42, and B22. [Modes for carrying out the invention]

[0020] In this specification, halogen atoms include, but are not limited to, fluorine, chlorine, bromine, iodine, astatine, and tennessine.

[0021] The alkyl group may be an alkyl group having 1 to 20 carbon atoms, or an alkyl group having 1 to 10 carbon atoms. Specifically, examples include, but are not limited to, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, secondary butyl group, octyl group, cyclohexyl group, tert-pentyl group, 3-methylpentan-3-yl group, 1-adamantyl group, and 2-adamantyl group.

[0022] The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms. Specifically, examples include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, an isopropyl group, a tertiary hydroxy group, a 2-ethyl octyloxy group, a benzyloxy group, etc.

[0023] A silyl group is a group in which a silicon atom has a hydrogen atom or a substituent. The substituent may be a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The substituted or unsubstituted alkyl group on the silicon atom may be a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. The substituted or unsubstituted aryl group on the silicon atom may be a substituted or unsubstituted aryl group having 6 to 10 carbon atoms. The silyl group may be a trialkylsilyl group or a triarylsilyl group. Specifically, examples include, but are not limited to, trimethylsilyl group and triphenylsilyl group.

[0024] The aryl group may be an aryl group having 6 to 20 carbon atoms, an aryl group having 6 to 18 carbon atoms, or an aryl group having 6 to 12 carbon atoms. Specifically, examples include, but are not limited to, phenyl, biphenyl, naphthyl, phenanthrenyl, triphenylenyl, indenyl, terphenyl, fluorenyl, pyrenyl, anthranyl, perilenyl, chrysenyl, and fluoranthenyl groups.

[0025] The heteroaryl group may be a heteroaryl group having 3 to 24 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms. Specifically, examples include, but are not limited to, pyridyl, pyrimidyl, pyrazyl, triazyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, carbazolyl, acridinyl, and phenanthrolyl groups.

[0026] The amino group may be a substituted amino group substituted with an alkyl group or an aryl group, and may be a substituted amino group substituted with an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 12 carbon atoms. Specifically, examples include, but are not limited to, N-methylamino group, N-ethylamino group, N,N-dimethylamino group, N,N-diethylamino group, N-methyl-N-ethylamino group, N-benzylamino group, N-methyl-N-benzylamino group, N,N-dibenzyloamino group, anilino group, N,N-diphenylamino group, N,N-dinaphthylamino group, N,N-difluorenylamino group, N-phenyl-N-tolylamino group, N,N-ditolylamino group, N-methyl-N-phenylamino group, N,N-dianisorylamino group, N-mesityl-N-phenylamino group, N,N-dimesitylamino group, N-phenyl-N-(4-tert-butylphenyl)amino group, N-phenyl-N-(4-trifluoromethylphenyl)amino group, N-piperidyl group, etc.

[0027] Examples of aryloxy groups include, but are not limited to, phenoxy groups.

[0028] Examples of heteroaryloxy groups include, but are not limited to, thienyloxy groups.

[0029] Examples of substituents that the alkyl, alkoxy, amino, aryloxy, silyl, aryl, heteroaryl, and heteroaryloxy groups may further have include, but are not limited to, deuterium, alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl groups, aralkyl groups such as benzyl groups, aryl groups such as phenyl and biphenyl groups, heterocyclic groups such as pyridyl and pyrrolyl groups, amino groups such as dimethylamino, diethylamino, dibenzylamino, diphenylamino, and ditolylamino groups, alkoxy groups such as methoxy, ethoxy, and propoxy groups, aryloxy groups such as phenoxy groups, halogen atoms such as fluorine, chlorine, bromine, and iodine, and cyano groups.

[0030] In this specification, the basic skeleton refers to the acenaphtho[1,2-k]benzo[e]acephenanthrene skeleton.

[0031] (1)Organic compounds The organic compound according to this embodiment is characterized by being represented by the general formula [1].

[0032] [ka]

[0033] ≪R 1 ~R 27 ≫ In the general formula [1], R1 to R 27 Each of these is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted amino group, and a cyano group.

[0034] R1 to R 27Each of these may be independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. Also, R1 to R 27 Each of these may be independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 12 carbon atoms. Also, R1 to R 27 Each of these may be independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and a phenyl group. Specifically, R1 to R 27 Each of these may be independently selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a CD3 group, an ethyl group, an iso-propyl group, a tert-butyl group, C(CH3)2(C2H5), C(CH3)(C2H5)2, a phenyl group, a phenyl group having a cyclohexyl group, and a biphenyl group. Also, R1 to R 27 Each of these may be independently selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a CD3 group, an iso-propyl group, a tert-butyl group, C(CH3)2(C2H5), C(CH3)(C2H5)2, and a phenyl group. Also, R1 to R 27 Each of these may be independently selected from the group consisting of a hydrogen atom, a methyl group, an iso-propyl group, a tert-butyl group, C(CH3)(C2H5)2, and a phenyl group.

[0035] R1 to R 27 At least one of them may be an atom other than a hydrogen atom. Also, R1, R3, R5, R 11 , R 14 , R 16 , R 18 , R 24 , and R 27 At least one of them may be an atom other than a hydrogen atom, and R1, R3, R5, R 14 , R 16 , R 18 , R 24 , and R 27At least one of them may be something other than a hydrogen atom. In one aspect of the present invention, R1, R5, R 14 , and R 18 At least one of these substituents may be a substituent other than a hydrogen atom, in which case the substituent other than a hydrogen atom may be a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and from the viewpoint of molecular weight, it is preferable that it is an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms. Specifically, it is preferable that it be a methyl group or a phenyl group.

[0036] Furthermore, in one aspect of the present invention, R3 and R 16 At least one of these substituents may be a substituent other than a hydrogen atom, and in this case, the substituent other than a hydrogen atom may be a substituted or unsubstituted alkyl group. From the viewpoint of molecular weight, it is preferable that the alkyl group has 1 to 6 carbon atoms. Specifically, it is preferable that it be a methyl group, a tert-butyl group, or C(CH3)(C2H5)2.

[0037] Furthermore, in one aspect of the present invention, R 24 and R 27 At least one of these atoms may be a hydrogen atom, and in this case, the substituents other than the hydrogen atom may be substituted or unsubstituted alkyl groups, and from the viewpoint of molecular weight, they are preferably alkyl groups having 1 to 4 carbon atoms. Specifically, they are preferably methyl groups.

[0038] Furthermore, R 21 and R 24 , and, R 22 and R 27 At least one of them may be joined to form a ring, which is preferably of general formula [1a] or [1b].

[0039] [ka]

[0040] In general formula [1a], Y is a chalcogen atom, preferably an oxygen atom or a sulfur atom.

[0041] In the general formula [1b], R 28 and R 29 Each of these is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted amino group, and a cyano group. 28 and R 29 They may combine to form a ring.

[0042] R 28 and R 29 It is preferable that each of the following is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, and a substituted or unsubstituted alkyl group; more preferably that each of the following is independently selected from a hydrogen atom, a deuterium atom, a fluorine atom, and a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms; and even more preferably that each of the following is independently selected from a hydrogen atom, a deuterium atom, and a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms.

[0043] In general formulas [1a] and [1b], ** represents the bonding position with general formula [1].

[0044] R 21 and R 24 , and, R 22 and R 27 The ring formed by the bonding of at least one of the elements may be an aromatic hydrocarbon ring having 5 to 10 carbon atoms or a heteroaromatic ring having 4 to 10 carbon atoms. Specifically, the ring preferably forms a 6-membered ring, and more preferably a benzene ring. 28 and R 29 The same applies to the rings formed by the bonding of these elements.

[0045] ≪Ar≫ In general formula [1], Ar is a substituted or unsubstituted aryl group. From the viewpoint of molecular weight, Ar is preferably a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, more preferably a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and even more preferably an aryl group having 6 to 10 carbon atoms. Specifically, it may be a phenyl group, a naphthyl group, a biphenyl group, a triphenylene group, or a phenanthrene group. Preferably, it is a phenyl group, a naphthyl group, or a biphenyl group, which may have a tert-butyl group as a substituent. Even more preferably, it may be a phenyl group or a naphthyl group.

[0046] When Ar has a substituent, the substituent may be a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. From the viewpoint of molecular weight, it is preferably a deuterium atom or an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably an alkyl group having 1 to 4 carbon atoms. Specifically, it may be a deuterium atom, a phenyl group, a naphthyl group, a biphenyl group, a triphenylene group, or a phenanthrene group, which are preferably a methyl group, a tert-butyl group, a C(CH3)(C2H5)2 group, a cyclopentyl group, a cyclohexyl group, or an adamantyl group. More preferably a tert-butyl group or a cyclohexyl group. More preferably a tert-butyl group.

[0047] Furthermore, when Ar has a substituent, it is preferable that the substituent is introduced at the ortho position relative to L in general formula [1].

[0048] ≪L≫ In general formula [1], L is one of general formulas [2] through [7], or a combination thereof. For example, when L is a combination of general formulas [2] and [3], then n, as described later, is 2.

[0049] [ka]

[0050] In general formulas [2] through [7], R 101 ~R 138 , R a , and R b X is independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aryl group. X is an oxygen atom or a sulfur atom. * indicates the bond position.

[0051] R a and R b This may be an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms, specifically a methyl group or a phenyl group. From the viewpoint of molecular weight, a methyl group is more preferred.

[0052] R a and R b These may bond to form a ring. This ring may be a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heteroaromatic ring, or a substituted or unsubstituted aromatic hydrocarbon ring. Specifically, R a and R b These may combine to form a fluorene skeleton. In other words, when L is general formula [6], general formula [6] may be a spirofluorene skeleton.

[0053] L may be one of the general formulas [2] through [7], one of the general formulas [2], or a combination of general formulas [2] and [3], one of the general formulas [2] through [7], or one of the general formulas [2], one of the general formulas [2], one of the general formulas [2], one of the general formulas [3], one of the general formulas [4], or one of the general formulas [2]. In this case, X may be an oxygen atom.

[0054] Also, R 101 ~R 138This may be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 2 carbon atoms. Specifically, it may be a hydrogen atom, a methyl group, a CD3 group, or an ethyl group, or a hydrogen atom, a methyl group, or an ethyl group.

[0055] ≪n≫ In the general formula [1], n is an integer between 1 and 5. A larger value of n indicates better molecular orientation, while a smaller value indicates better sublimation. Therefore, it is preferable that n is between 1 and 3.

[0056] Next, a method for synthesizing the organic compound according to this embodiment will be described. The organic compound according to this embodiment is synthesized, for example, according to the reaction scheme shown below.

[0057] [ka]

[0058] As shown in the synthesis scheme described above, the organic compounds according to this embodiment are synthesized using the compounds shown in (a) to (c) below as raw materials. (a) Asenaphthenequinone derivative (E1) (b) Dibenzyl ketone derivative (E2) (c) Long-chain aromatic hydrocarbon derivatives (E3) Here, by appropriately introducing substituents to the compounds shown in (a) to (c) above, R1 to R in formula (1) 27 One of these will be substituted for a hydrogen atom with a predetermined group other than a hydrogen atom. Furthermore, by changing E1 to E3 in the above synthesis scheme, various organic compounds can be synthesized. However, the synthesis method is not limited to these.

[0059] Next, the organic compound according to this embodiment will be described. The organic compound according to this embodiment has the following configuration and therefore exhibits excellent luminescence efficiency and color purity. In this specification, the emission wavelength of blue emission with excellent color purity refers to emission in which the peak of the emission spectrum in a dilute toluene solution is 430 nm or more and less than 460 nm. (1-1) Because the basic skeleton has multiple aryl groups in the direction of the long axis, the horizontal orientation is improved. (1-2) Because benzene is directly bonded along the long axis of the basic skeleton, π conjugation is difficult to extend. The following will explain these in detail. (1-1) Because the basic skeleton has multiple aryl groups in the direction of the long axis, the horizontal orientation is improved. As a result of diligent research, the inventors have found that by having multiple aryl groups in the direction of the long axis of the basic skeleton, the horizontal orientation can be improved, and the effect of improving luminescence efficiency can be obtained.

[0060] The horizontal orientation of an organic compound can be expressed by a statistical parameter called the Pz value. A Pz value of 0 indicates that the organic compound is arranged parallel to the substrate, while a Pz value of 1 indicates that the organic compound is arranged perpendicular to the substrate. Therefore, a smaller Pz value is preferable because it indicates improved horizontal orientation of the organic compound.

[0061] Figure 8 shows the transition dipole moment direction and emission direction for the organic compound according to the present invention and a comparative compound. As shown in Figure 8, the light emitted from the organic compound is extracted in a direction substantially perpendicular to the intramolecular transition dipole moment (a factor that determines the direction and intensity of the electric field of emission). In the organic compound according to this embodiment, the intramolecular transition dipole moment is in the direction of the long axis of the basic skeleton. Therefore, by orienting the organic compound according to this embodiment horizontally with respect to the substrate, the intramolecular transition dipole moment can also be oriented horizontally with respect to the substrate. As a result, the light emitted from the organic compound can be extracted in a direction substantially perpendicular to the substrate. For these reasons, by improving the horizontal orientation of the organic compound according to this embodiment, an organic compound with excellent luminescence efficiency can be obtained.

[0062] To clarify the relationship between the horizontal orientation and luminous efficiency of organic compounds, the Pz values ​​and luminous efficiency of the organic compound according to this embodiment and a comparative compound were measured and compared. The results are shown in Table 1. The Pz values ​​were obtained by fabricating a film with the same configuration as the luminescent layer on quartz glass using vacuum deposition, and measuring the thin film using Hamamatsu Photonics' "Molecular Orientation Characteristic Measurement Device C14234-01". The luminous efficiency is a relative value with the luminous efficiency of Comparative Example 2 set to 1.0.

[0063] [Table 1]

[0064] Table 1 shows that the Pz values ​​of the organic compounds according to this embodiment were 0.03 and 0.05, respectively, which are smaller than the Pz values ​​of comparative compounds 1-a and 1-b. It is thought that the organic compounds according to this embodiment exhibited smaller Pz values ​​because they have substituents along the long axis of the basic skeleton. As a result of the smaller Pz values, the horizontal orientation of the organic compounds improved, leading to improved light extraction efficiency and thus excellent luminescence efficiency.

[0065] On the other hand, comparative compound 1-a has a structure in which one benzene ring is bonded to the long axis and one to the uniaxial axis of the organic compound. Comparative compound 1-b has a structure in which multiple aryl groups (benzene rings) are bonded to the uniaxial axis of the organic compound, but only one benzene ring is bonded to the long axis. Since these compounds do not have multiple aryl groups in the long axis direction of the organic compound, they exhibit a larger Pz value compared to the organic compound according to this embodiment. Therefore, the organic compound according to this embodiment exhibits higher horizontal orientation and thus higher luminescence efficiency compared to the comparative compounds.

[0066] Therefore, we found that the organic compound according to the present invention exhibits a small Pz value by bonding multiple aryl groups along the long axis of the organic compound, indicating that the horizontal orientation of the basic skeleton is improved.

[0067] (1-2) Because benzene is directly bonded along the long axis of the basic skeleton, π conjugation is difficult to extend. In this embodiment, the organic compound has benzene directly bonded along the long axis of the basic skeleton, which makes it difficult for π-conjugation to extend. As a result, the organic compound in this embodiment can produce blue light emission with excellent color purity.

[0068] As described above, in order to lower the Pz value, the organic compound according to this embodiment has multiple aryl groups substituted in the long axis direction, which is the direction of the transition dipole moment of the basic skeleton, but this also leads to the elongation of π conjugation. Since the elongation of π conjugation causes the emission wavelength of the organic compound to become longer, it is necessary to reduce the elongation of π conjugation in order to obtain blue emission with excellent color purity. Therefore, the inventors have found that by directly bonding benzene in the long axis direction of the basic skeleton, it is possible to reduce the elongation of π conjugation while improving the horizontal orientation of the basic skeleton.

[0069] Table 2 shows the emission wavelengths and Pz values ​​of the organic compounds according to this embodiment and comparative compound 2-a. Figure 9 shows the HOMO distribution of these compounds.

[0070] [Table 2]

[0071] Table 2 shows that organic compound A1 according to the present invention exhibits a Pz value equal to or greater than that of comparative compound 2-a, and emits blue light with a shorter wavelength than comparative compound 2-a. This is thought to be because the direct bonding of benzene to the basic skeleton reduced the extension of π-conjugation. For example, referring to Figure 9, in example compound A1, π-conjugation extends to the basic skeleton and to the phenyl group directly bonded to the basic skeleton, and the π-conjugation is broken between the phenyl group and the naphthyl group. In contrast, in comparative compound 2-a, π-conjugation extends to the basic skeleton and to the naphthyl group directly bonded to the basic skeleton. Therefore, the organic compound according to this embodiment can suppress the extension of π-conjugation compared to comparative compound 2-a. As a result, the emission wavelength of the organic compound according to the present invention is about 11 nm shorter than that of comparative compound 2-a. Therefore, the organic compound according to this embodiment can emit blue light with excellent color purity.

[0072] Furthermore, substituents bonded to substituents directly bonded to the basic skeleton do not participate in the elongation of π-conjugation, so such substituents may be fused polycyclic substituents.

[0073] The electron orbital distribution described above was visualized using molecular orbital calculations. The molecular orbital calculation method used was the widely adopted Density Functional Theory (DFT). The functional used was B3LYP, and the basis set was 6-31G*.For example, the fuel-control system is based on Gaussian09(Gaussian09,RevisionC.01,MJFrisch,GWTrucks,HBSchlegel,GEScuseria, MARobb, JRCheeseman, G. Scalmani, V. Barone, B. Mennucci, G. Petersson, H. Nakatsuji, M. Caricato, X. Li, HPHratch ian, AFIzmaylov, J. Bloino, G. Zheng, JLSonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, [ PMC free article ] [ PubMed ] Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J. Montgomery, Jr., Peralta J. Ogliaro, Bearpark M., JJHeyd ,E.Brothers,KNKudin,VNStaroverov,T.Keith,R.Kobayashi,J.Normand,K.Raghavachari,A.Rendell,JCBurant,S SIyengar, J. Thomas, M. Cossi, N. Rega, JMMillam, M. Klene, JEKnox, JBCross, V. Bakken, C. Adamo, J. Jaramillo, R. Go mperts,REStratmann,O.Yazyev,AJAustin,R.Cammi,C.Pomelli,JWOchterski,RLMartin,K.Morokuma,VGZakrzewsk i,GAVoth,P.Salvador,JJDannenberg,S.Dapprich,ADDaniels,O.Farkas,JBForesman,JVOrtiz,JCioslowski,and DJFox,Gaussian,Inc.,Wallingford CT,2010.) In addition, a scientifically-defined scientific study was conducted.

[0074] For the reasons stated above, the organic compound according to the present invention has multiple aryl groups in the longitudinal direction relative to the basic skeleton, thus improving horizontal orientation. Furthermore, because the aryl group directly bonded to the basic skeleton is a phenyl group, the elongation of π-conjugation can be reduced. Therefore, the organic compound according to the present invention exhibits excellent color purity and luminescence efficiency.

[0075] Furthermore, the organic compound according to this embodiment preferably has the following configuration.

[0076] (1-3)R 24 and R 27 At least one of them is a substituted or unsubstituted alkyl group. (1-4) R1, R5, R 14 , and R 18 At least one of them is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. (1-5) Ar, R3, and R 16 At least one of them has a secondary alkyl group or a tertiary alkyl group. The following describes these configurations.

[0077] (1-3)R 24 and R 27 At least one of them is a substituted or unsubstituted alkyl group. The organic compound according to this embodiment is R 24 and R 27 Preferably, at least one of the alkyl groups is substituted or unsubstituted. This configuration further suppresses the π-conjugation, resulting in shorter emission wavelengths. As a result, the organic compound according to this embodiment exhibits blue emission with excellent color purity.

[0078] In the organic compound according to this embodiment, R 24 and R 27At least one of them is preferably an alkyl group having 1 to 6 carbon atoms, and more preferably an alkyl group having 1 to 4 carbon atoms. Specifically, it may be a methyl group, a CD3 group, an ethyl group, an iso-propyl group, or a tert-butyl group, and may be a methyl group or a CD3 group, and may be a methyl group. Also, R 24 and R 27 It is preferable that the alkyl group is substituted or unsubstituted.

[0079] Table 3 shows the emission wavelengths and Pz values ​​of exemplary organic compounds A26, B42, and B22 according to this embodiment. Figure 10 shows the orbital distribution of the HOMO of these compounds.

[0080] [Table 3]

[0081] From Table 3, it was found that the emission wavelengths of the exemplary organic compounds A26, B42, and B24 according to this embodiment are different. Referring to the HOMO orbital distribution shown in Figure 10, R 24 and R 27 In example compound A26, where R is a methyl group, the orbital distribution of the HOMO extends only to the basic skeleton, and R 27 In example compound B42, where R is a methyl group, the orbital distribution of the HOMO extends to the basic skeleton and the phenyl group directly bonded to the basic skeleton. On the other hand, R 24 and R 27 In example compound B22, where the atom is a hydrogen atom, the orbital distribution of the HOMO extends not only to the basic skeleton and the phenyl group directly bonded to the basic skeleton, but also to phenyl groups further bonded to those phenyl groups.

[0082] This is R 24 and R 27Since at least one of them is a substituted or unsubstituted alkyl group, the basic skeleton and the substituents attached to the basic skeleton are arranged so as to be twisted, and thus the orbital distribution of the HOMO is difficult to spread. As a result, the organic compound according to this embodiment exhibits bluer light emission with a shorter wavelength while maintaining the Pz value, and thus is an organic compound having excellent color purity.

[0083] (1-4)R1, R5, R 14 , and R 18 At least one of them is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group In the organic compound according to this embodiment, it is preferable that at least one of R1, R5, R 14 , and R 18 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. By having this configuration, intermolecular stacking between organic compounds can be more suppressed, so that sublimability can be improved. In addition, suppression of intermolecular stacking can also suppress concentration quenching, so that the luminescence quantum efficiency (PLQY) can be improved.

[0084] In particular, improvement of sublimability is important in terms of increasing the purity of the organic compound. Generally, when an organic compound is used in an organic light-emitting device, impurities are removed by performing sublimation purification. Therefore, an organic compound having excellent sublimability can obtain a higher purity organic compound by sublimation purification. As a result, during device driving, element degradation due to impurities can be further reduced, so it is preferable that the sublimation margin temperature shows a large value. In addition, since the sublimability of the organic compound is excellent, decomposition of the organic compound can be reduced during sublimation purification or evaporation, which is preferable. The sublimation margin temperature is the difference between the decomposition temperature of the organic compound and the sublimation temperature (the temperature at which sublimation starts) of the organic compound. The decomposition temperature of the organic compound can be defined as the temperature at which the degree of vacuum deteriorates.

[0085] Table 4 shows the sublimation margin temperatures and element durability ratios of C8, C5, C56, and B22, which are organic compounds according to this embodiment.

[0086]

Table 4

[0087] From Table 4, it was found that for exemplary compounds C8, C5, and C56 in which at least one of R1, R5, R 14 , and R 18 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, the sublimation margin temperature showed a higher value than that of exemplary compound B19 in which R1, R5, R 14 , and R 18 are hydrogen atoms. As a result, exemplary compounds C8, C5, and C56 showed better durability compared to exemplary compound B22.

[0088] The basic skeleton of the organic compound according to the present invention has a highly planar structure and is a structure that easily undergoes intermolecular stacking. Therefore, when at least one of R1, R5, R 14 , and R 18 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, these substituents can sufficiently cover the basic skeleton. As a result, the effect of suppressing intermolecular stacking becomes greater, so the sublimation margin temperature also increases, and it is considered that the device durability is also excellent.

[0089] Also, for the organic compound according to the present embodiment, when at least one of R1, R5, R 14 , and R 18 is a substituted or unsubstituted alkyl group, it shows a lower Pz value, which is preferable. When the Pz values of exemplary compounds C4 and C7 were measured by the above-described method, the values were 0.05 and 0.06, respectively. It was found that when at least one of R1, R5, R 14 , and R 18 is a substituted or unsubstituted alkyl group, the horizontal alignment property is improved. This is because when at least one of R1, R5, R 14 , and R 18The fact that at least one of them is a substituted or unsubstituted alkyl group makes it easier for it to interact with the basic skeleton, which is thought to have led to improved horizontal orientation of the organic compound according to this embodiment. For the reasons above, the organic compound according to this embodiment is R1, R5, R 14 , and R 18 Preferably, at least one of them is a substituted or unsubstituted alkyl group.

[0090] (1-5) Ar, R3, and R 16 At least one of them has a secondary alkyl group or a tertiary alkyl group. The organic compound according to this embodiment is Ar, R3, and R 16 Having at least one of the molecules a secondary or tertiary alkyl group further suppresses intermolecular stacking, thus reducing concentration quenching. As a result, the organic compound according to this embodiment is an organic compound with excellent PLQY. Examples of secondary or tertiary alkyl groups include iso-propyl groups and tert-butyl groups, and these alkyl groups are preferred because they have a bulky structure.

[0091] Secondary alkyl groups and tertiary alkyl groups are linked via aryl and heteroaryl groups, resulting in Ar, R3, and R 16 They may be bonded to each other. Also, from the viewpoint of molecular weight, Ar, R3, and R 16 Preferably, at least one of them is a secondary alkyl group or a tertiary alkyl group, more preferably an iso-propyl group or a tert-butyl group, and more preferably a tert-butyl group.

[0092] Table 5 shows the PLQY and Pz values ​​of D9 and B19, which are organic compounds according to this embodiment. PLQY was measured by vacuum deposition on quartz glass in a ratio of 99% by weight of one type of host material and 1% by weight of the guest material (organic compound according to this embodiment), and then measuring the PLQY of the thin film using Hamamatsu Photonics' "Absolute PL Quantum Yield Measurement Device".

[0093] [Table 5]

[0094] From Table 5, Ar, R3, and R 16 PLQY of exemplary compound D9, which has a tert-butyl group that is a tertiary alkyl group, is Ar, R3, and R 16 Compared to example compound B22, which has a hydrogen atom, it showed higher values. This is because Ar, R3, and R 16 This is thought to be because the bulky alkyl group suppresses intermolecular stacking. Therefore, the organic compound according to this embodiment contains Ar, R3, and R 16 Since at least one of them has a secondary or tertiary alkyl group, it has excellent PLQY properties.

[0095] Specific examples of organic compounds according to the present invention are shown below. However, the present invention is not limited to these. Structural isomers of the following compounds are also included as exemplary compounds.

[0096] [ka]

[0097] [ka]

[0098] [ka]

[0099] [ka]

[0100] [ka]

[0101] [ka]

[0102] [ka]

[0103] [ka]

[0104] [ka]

[0105] [ka]

[0106] [ka]

[0107] [ka]

[0108] Among the example compounds listed above, the compounds in group A are R 24 and R 27 These are compounds in which the atom is either a hydrogen atom or a deuterium atom. Therefore, compounds belonging to group A emit longer wavelength light than other organic compounds according to the present invention and exhibit particularly excellent durability.

[0109] Among the example compounds listed above, those belonging to group B are R 24 and R 27The compound has at least one alkyl group. Among the phenyl groups directly bonded to the basic skeleton, having a substituent in the ortho position relative to the basic skeleton causes the phenyl group to twist relative to the basic skeleton, making it difficult for the π-conjugation to extend. As a result, compounds belonging to group B exhibit the effect of shorter emission wavelengths and blue emission with higher color purity.

[0110] Of the example compounds listed above, those belonging to group C are R1, R5, R in the general formula [1]. 14 , R 18 At least one of these molecules has a substituent. As a result, the basic skeleton twists relative to the phenyl group bonded along its short axis, reducing intermolecular stacking and improving sublimation properties. Therefore, compounds belonging to group C exhibit superior device durability.

[0111] Of the example compounds listed above, those belonging to group D have R3, R in the general formula [1]. 16 It has a bulky substituent on either , or Ar. Therefore, intermolecular stacking is reduced, and when a compound belonging to group D is used as a guest material in the light-emitting layer, concentration quenching can be suppressed, resulting in an improved PLQY.

[0112] (2) Organic light-emitting element Next, an organic light-emitting element according to one embodiment of the present invention will be described. The organic light-emitting element according to one embodiment of the present invention has a first electrode, a second electrode, and an organic compound layer disposed between these electrodes. One of the first electrode and the second electrode is an anode and the other is a cathode. In the organic light-emitting element according to this embodiment, the organic compound layer may be a single layer or a laminate consisting of multiple layers, as long as it has a light-emitting layer. The organic compound according to the present invention may be contained in the organic compound layer, and preferably it is contained in the light-emitting layer. Here, if the organic compound layer is a laminate consisting of multiple layers, the organic compound layer may have a hole injection layer, a hole transport layer, an electron blocking layer, a hole-exciton blocking layer, an electron transport layer, an electron injection layer, etc., in addition to the light-emitting layer. The light-emitting layer may be a single layer or a laminate consisting of multiple layers. If there are multiple light-emitting layers, a charge generation layer may be provided between the light-emitting layers. The charge generation layer may be composed of a compound whose LUMO (Lowest Unoccupied Molecular Orbital) energy level is lower than that of the hole transport layer, and the LUMO energy level of the charge generation layer may be lower than that of the HOMO energy level of the hole transport layer. Here, the HOMO and LUMO energy levels of the organic compound layer may be those of the organic compound with the largest weight ratio in the organic compound layer.

[0113] Here, the HOMO energy level and LUMO energy level are described as "higher" the closer they are to the vacuum level. When the LUMO energy level of the charge generation layer is lower than the HOMO energy level of the hole transport layer, it means that the LUMO energy level of the charge generation layer is further from the vacuum level than the HOMO energy level of the hole transport layer.

[0114] In this specification, the HOMO energy level and LUMO energy level can be calculated using molecular orbital calculations.

[0115] In this specification, the HOMO energy level and LUMO energy level can also be calculated using the ionization potential and band gap. The HOMO energy level can be estimated by measuring the ionization potential. The ionization potential can be measured using a measuring device such as AC-3 after dissolving the compound to be measured in a solvent such as toluene or after creating a vapor-deposited film of the compound on a substrate such as glass. The band gap can be measured by dissolving the compound to be measured in a solvent such as toluene and irradiating it with excitation light. The band gap can be measured by measuring the absorption edge of the absorption spectrum of the excitation light. Alternatively, the compound to be measured can be vapor-deposited on a substrate such as glass and irradiated with excitation light. The measurement can be performed by measuring the absorption edge of the absorption spectrum of the vapor-deposited film that absorbs the excitation light.

[0116] The LUMO energy level can be calculated using the band gap and ionization potential. By subtracting the ionization potential from the band gap, the LUMO energy level can be estimated.

[0117] The LUMO energy level can also be estimated from the reduction potential. For example, the one-electron reduction potential can be estimated using cyclic volmetry (CV) measurement. CV measurements are performed, for example, in a 0.1 M tetrabutylammonium perchlorate DMF solution with an Ag / Ag reference electrode. + The measurement can be performed using Pt as the counter electrode and glassy carbon as the working electrode. The LUMO energy level can be estimated by adding the difference of -4.8 eV between the reduction potential of the obtained compound and the reduction potential of ferrocene to the obtained compound.

[0118] In an organic light-emitting element according to one embodiment of the present invention, if the organic compound according to the present invention is included in the light-emitting layer, the light-emitting layer may consist only of the organic compound according to the present invention, or it may consist of the organic compound according to the present invention and other compounds. Here, if the light-emitting layer consists of the organic compound according to the present invention and other compounds, the organic compound according to the present invention may be used as a host material for the light-emitting layer, or as a guest material. It may also be used as an assist material that can be included in the light-emitting layer. Here, the host material is also called the "host" or "first compound," and is the compound with the largest mass ratio among the compounds constituting the light-emitting layer. The guest material is also called the "guest," "dopant material," "dopant," or "third compound," and is a compound with a smaller mass ratio than the host among the compounds constituting the light-emitting layer, and is the compound that is primarily responsible for light emission. For this reason, the guest material is sometimes also called the light-emitting material. The assist material is also called the "assist" or "second compound," and is a compound with a smaller mass ratio than the host material among the compounds constituting the light-emitting layer, and assists the light emission of the guest material. The assist material is also called the second host.

[0119] Here, let S1(H) be the lowest singlet excitation energy of the host material, S1(D) be the lowest singlet excitation energy of the guest material, and S1(A) be the lowest singlet excitation energy of the assist material. The guest material may be considered to be an organic compound according to the present invention. In this case, it is preferable that the organic light-emitting device according to this embodiment satisfies S1(H)>S1(D) or S1(H)>S1(A)>S1(D). By satisfying the above relationship between the lowest singlet excitation energy of the compound included in the organic light-emitting device according to this embodiment, excitons can be efficiently transferred to the guest material, resulting in an organic light-emitting device with superior luminescence efficiency.

[0120] When the organic compound according to the present invention is used as a guest material for the light-emitting layer, the concentration of the guest material may be 0.01% by mass or more and less than 50% by mass relative to the entire light-emitting layer, preferably 0.01% by mass or more and 20% by mass or less, more preferably 0.01% by mass or more and 10% by mass or less, and even more preferably 0.01% by mass or more and 5% by mass or less.

[0121] When the light-emitting layer further contains an assisting material, the assisting material may be 1% by mass or more and less than 50% by mass of the entire light-emitting layer, and is preferably 10% by mass or more and less than 50% by mass. The guest may be 0.01% by mass or more and 20% by mass or less, and is preferably 0.01% by mass or more and 5% by mass or less.

[0122] The inventors have conducted various studies and found that when the organic compound according to the present invention is used as a host material or guest material for the light-emitting layer, particularly as a guest material for the light-emitting layer, a device can be obtained that exhibits high efficiency, high brightness, and extremely high durability. This light-emitting layer may be a single layer or a multi-layer, and it is also possible to mix the light emission with the blue light emission of this embodiment by including a light-emitting material having another light emission color. A multi-layer means a state in which one light-emitting layer and another light-emitting layer are stacked. In this case, the light emission color of the organic light-emitting element is not limited to blue. More specifically, it may be white or an intermediate color. In the case of white, the other light-emitting layer emits a color other than blue, i.e., red or green. Furthermore, the film is formed by vapor deposition or coating. Details of this will be explained in detail in the examples described later.

[0123] The organic compound according to the present invention can be used as a constituent material for organic compound layers other than the light-emitting layer constituting the organic light-emitting device according to this embodiment. Specifically, it may be used as a constituent material for electron transport layers, electron injection layers, hole transport layers, hole injection layers, hole blocking layers, etc. In this case, the light-emitting color of the organic light-emitting device is not limited to blue. More specifically, it may be white light or an intermediate color.

[0124] (3) Other compounds In addition to the organic compounds according to the present invention, conventionally known low-molecular-weight and high-molecular-weight hole-implanting or hole-transporting compounds, host materials, luminescent compounds, electron-injecting or electron-transporting compounds, etc., can be used together as needed. Examples of these compounds are listed below.

[0125] As hole-implantation transport materials, materials with high hole mobility are preferred to facilitate hole injection from the anode and to transport the injected holes to the light-emitting layer. Furthermore, materials with a high glass transition temperature are preferred to reduce film quality degradation such as crystallization in organic light-emitting devices. Examples of low-molecular-weight and high-molecular-weight materials with hole-implantation transport properties include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. Moreover, the above-mentioned hole-implantation transport materials are also suitably used in electron-blocking layers. Specific examples of compounds used as hole-implantation transport materials are shown below, but are not limited to these.

[0126] [ka]

[0127] Guest materials primarily involved in luminescence include organic compounds represented by the general formula [1], as well as fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, organoaluminum complexes such as tris(8-quinolinolate)aluminum, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, and polymer derivatives such as poly(phenylenevinylene) derivatives, poly(fluorene) derivatives, and poly(phenylene) derivatives. Specific examples of compounds used as luminescent materials are shown below, but are not limited to these.

[0128] [ka]

[0129] Examples of host or assist materials included in the luminescent layer include aromatic hydrocarbon compounds or their derivatives, as well as carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organoaluminum complexes such as tris(8-quinolinolate)aluminum, and organoberylium complexes. Specific examples of compounds used as luminescent layer hosts or luminescence assist materials are shown below, but are not limited to these.

[0130] [ka]

[0131] Among EM1 to EM40, the host material may be a hydrocarbon compound having a condensed polycyclic hydrocarbon group. Specifically, these are EM1 to EM12 and EM16 to EM27.

[0132] As electron-transporting materials, any material capable of transporting electrons injected from the cathode to the light-emitting layer can be arbitrarily selected, taking into consideration the balance with the hole mobility of the hole-transporting material. Examples of materials with electron-transporting properties include oxadiazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organoaluminum complexes, and fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the above electron-transporting materials are also suitably used in the hole-blocking layer. Specific examples of compounds used as electron-transporting materials are shown below, but are of course not limited to these.

[0133] [ka]

[0134] Electron-injectable materials can be arbitrarily selected from those that allow for easy electron injection from the cathode, taking into consideration the balance with hole injection properties. Organic compounds include n-type dopants and reducing dopants. Examples include alkali metal compounds such as lithium fluoride, lithium complexes such as lithium quinolinol, benzimidazolidene derivatives, imidazolidene derivatives, fluvalene derivatives, and acridine derivatives.

[0135] (4) Configuration of organic light-emitting element The following describes the components that make up the organic light-emitting element of this embodiment.

[0136] An organic light-emitting element is provided on a substrate by forming an insulating layer, a first electrode, an organic compound layer, and a second electrode. A protective layer, a color filter, a microlens, etc., may be provided on the second electrode. If a color filter is provided, a planarization layer may be provided between it and the protective layer. The planarization layer can be made of acrylic resin or the like. The same applies when a planarization layer is provided between the color filter and the microlens.

[0137] [substrate] Examples of substrates include quartz, glass, silicon wafers, resins, and metals. The substrate may also be equipped with switching elements such as transistors and wiring, and an insulating layer may be provided on top of them. The insulating layer can be made of any material that allows for the formation of contact holes between it and the first electrode, while ensuring insulation from wiring that is not connected. For example, resins such as polyimide, silicon oxide, and silicon nitride can be used.

[0138] [electrode] A pair of electrodes can be used. This pair consists of a first electrode and a second electrode. Specifically, the pair of electrodes may be an anode and a cathode. When an electric field is applied in the direction in which the organic light-emitting element emits light, the electrode with the higher potential is the anode, and the other is the cathode. Alternatively, the electrode that supplies holes to the light-emitting layer can be the anode, and the electrode that supplies electrons can be the cathode.

[0139] The anode material should ideally have a high work function. For example, elemental metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten, or mixtures containing these, or alloys combining them, as well as metal oxides such as tin oxide, zinc oxide, indium oxide, tin-indium oxide (ITO), and zinc-indium oxide can be used. Conductive polymers such as polyaniline, polypyrrole, and polythiophene can also be used.

[0140] These electrode materials may be used individually or in combination of two or more types. Furthermore, the anode may consist of a single layer or multiple layers.

[0141] When used as a reflective electrode, materials such as chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys or laminates thereof can be used. These materials can also function as reflective films without serving as electrodes. Furthermore, when used as a transparent electrode, oxide transparent conductive layers such as indium tin oxide (ITO) or indium zinc oxide can be used, but are not limited to these. Photolithography techniques can be used to form the electrodes.

[0142] Materials with a low work function are preferred for the cathode. Examples include alkali metals such as lithium, alkaline earth metals such as calcium, and elemental metals or mixtures containing aluminum, titanium, manganese, silver, lead, and chromium. Alternatively, alloys combining these elemental metals can also be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper, and zinc-silver can be used. Metal oxides such as indium tin oxide (ITO) can also be used. These electrode materials may be used individually or in combination of two or more. The cathode may also be a single-layer or multi-layer structure. Among these, silver is preferred, and a silver alloy is even more preferred to reduce silver aggregation. The alloy ratio is not important as long as silver aggregation is reduced. For example, the ratio of silver to other metals may be 1:1, 3:1, etc.

[0143] The cathode may be a top-emission element using an oxide conductive layer such as ITO, or a bottom-emission element using a reflective electrode such as aluminum (Al), and is not particularly limited. The method for forming the cathode is not particularly limited, but using DC and AC sputtering methods is more preferable because it provides good film coverage and makes it easier to reduce resistance.

[0144] [Organic compound layer] The organic compound layer may be formed as a single layer or as multiple layers. If there are multiple layers, they may be called a hole injection layer, a hole transport layer, an electron blocking layer, an emissive layer, a hole blocking layer, an electron transport layer, or an electron injection layer, depending on their function. The organic compound layer is mainly composed of organic compounds, but may also contain inorganic atoms and inorganic compounds. For example, it may contain copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, etc. The organic compound layer may be placed between the first electrode and the second electrode, or it may be placed in contact with the first electrode and the second electrode.

[0145] The organic compound layers constituting the organic light-emitting element according to this embodiment (hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, electron injection layer, etc.) are formed by the method shown below.

[0146] The organic compound layer constituting the organic light-emitting element according to this embodiment can be formed using dry processes such as vacuum deposition, ionization deposition, sputtering, or plasma deposition. Alternatively, a wet process can be used instead of a dry process, in which the organic compound is dissolved in a suitable solvent and the layer is formed by a known coating method (e.g., spin coating, dipping, casting, LB method, inkjet method, etc.).

[0147] By forming layers using methods such as vacuum deposition or solution coating, crystallization is less likely to occur, resulting in excellent stability over time. Furthermore, when forming films using coating methods, it is possible to combine the film with an appropriate binder resin.

[0148] Examples of the binder resins mentioned above include, but are not limited to, polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenolic resin, epoxy resin, silicone resin, and urea resin.

[0149] Furthermore, these binder resins may be used individually as homopolymers or copolymers, or as a mixture of two or more types. Additionally, known additives such as plasticizers, antioxidants, and UV absorbers may be used in combination as needed.

[0150] [Protective layer] A protective layer may be provided on the cathode. For example, by bonding glass with a desiccant to the cathode, the intrusion of water and other substances into the organic compound layer can be reduced, thereby reducing the occurrence of display defects. In another embodiment, a passivation film such as silicon nitride may be provided on the cathode to reduce the intrusion of water and other substances into the organic compound layer. For example, after forming the cathode, it may be transported to another chamber without breaking the vacuum and a silicon nitride film with a thickness of 2 μm may be formed by the CVD method to serve as a protective layer. A protective layer may also be provided using atomic deposition (ALD) after film formation by the CVD method. The material of the film formed by the ALD method is not limited, but may be silicon nitride, silicon oxide, aluminum oxide, etc. Silicon nitride may be further formed on the film formed by the ALD method by the CVD method. The film formed by the ALD method may have a smaller film thickness than the film formed by the CVD method. Specifically, the film thickness of the film formed by the ALD method may be 50% or less, or even 10% or less, of the film thickness of the film formed by the CVD method.

[0151] [Color Filter] A color filter may be provided on top of the protective layer. For example, a color filter that takes into account the size of the organic light-emitting element may be provided on a separate substrate and bonded to the substrate on which the organic light-emitting element is provided, or a color filter may be patterned on the protective layer as described above using photolithography technology. The color filter may be made of polymer.

[0152] [Planarization layer] A planarizing layer may be provided between the color filter and the protective layer. The planarizing layer is provided to reduce the unevenness of the layer below. It may also be called a material resin layer without limiting its purpose. The planarizing layer may be composed of an organic compound, which may be low molecular weight or high molecular weight, but high molecular weight is preferred.

[0153] The planarization layer may be provided above or below the color filter, and its constituent materials may be the same or different. Specifically, examples include polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenolic resin, epoxy resin, silicone resin, urea resin, etc.

[0154] [Microlens] The organic light-emitting element according to this embodiment may have an optical element such as a microlens on the light-emitting side. The microlens may be made of acrylic resin, epoxy resin, or the like. The microlens may be used to increase the amount of light extracted from the organic light-emitting element and to control the direction of the extracted light. The microlens may have a hemispherical shape. If it has a hemispherical shape, among the tangents that are tangent to the hemisphere, there is a tangent that is parallel to the insulating layer, and the point of contact between that tangent and the hemisphere is the vertex of the microlens. The vertex of the microlens can be similarly determined in any cross-sectional view. That is, among the tangents that are tangent to the semicircle of the microlens in the cross-sectional view, there is a tangent that is parallel to the insulating layer, and the point of contact between that tangent and the semicircle is the vertex of the microlens.

[0155] Furthermore, the midpoint of a microlens can also be defined. In the cross-section of a microlens, a line segment can be imagined from the point where one arc shape begins to the point where another arc shape begins, and the midpoint of this line segment can be called the midpoint of the microlens. The cross-section used to determine the vertices and midpoints may be a cross-section perpendicular to the insulating layer.

[0156] [Opposite substrate] A counter substrate may be provided on the planarized layer. The counter substrate is called a counter substrate because it is provided in a position corresponding to the aforementioned substrate. The constituent material of the counter substrate may be the same as that of the aforementioned substrate. The counter substrate may be the second substrate if the aforementioned substrate is referred to as the first substrate.

[0157] [Pixel circuit] The light-emitting device may have a pixel circuit connected to a light-emitting element. The pixel circuit may be an active-matrix type that independently controls the light emission of a first light-emitting element and a second light-emitting element. The active-matrix type circuit may be voltage-programmed or current-programmed. The drive circuit has a pixel circuit for each pixel. The pixel circuit may have a light-emitting element, a transistor that controls the light emission brightness 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 brightness, and a transistor for connecting to GND without going through the light-emitting element.

[0158] 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.

[0159] The slope of the current-voltage characteristics of the transistors constituting the pixel circuit can 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 using the so-called Vg-Ig characteristic.

[0160] The transistors that make up the pixel circuit are transistors connected to light-emitting elements, such as the first light-emitting element.

[0161] [Pixels] The organic light-emitting device has multiple pixels. Each pixel has subpixels that emit light of a different color from the others. The subpixels may each have, for example, RGB light-emitting colors.

[0162] A pixel emits light in a region also called the pixel aperture. This region is the same as the first region. The pixel aperture may be 15 μm or less, or 5 μm or more. More specifically, it may be 11 μm, 9.5 μm, 7.4 μm, 6.4 μm, etc.

[0163] The distance between subpixels may be 10 μm or less, specifically 8 μm, 7.4 μm, or 6.4 μm.

[0164] Pixels can take on known arrangements in a plan view. For example, they may be in a stripe arrangement, delta arrangement, pentile arrangement, or Bayer arrangement. The shape of subpixels in a plan view may be any known shape. For example, rectangles, rhombuses, hexagons, etc. Of course, even if it is not a precise shape, if it is close to a rectangle, it is included in the category of rectangles. The shape of subpixels and the pixel arrangement can be used in combination.

[0165] (5) Applications of the organic light-emitting element according to this embodiment The organic light-emitting element according to this embodiment can be used as a component of an image display device, a display device, or a lighting device. Other applications include a display unit for an image display device having a display unit and a housing on which the display unit is provided, an exposure light source for an electrophotographic image forming apparatus, a backlight for a liquid crystal display device, and a light-emitting device having a color filter in a white light source.

[0166] The display device may also be an image information processing device that has an image input unit for receiving image information from an area CCD, linear CCD, memory card, etc., an information processing unit for processing the input information, and displays the input image on the display unit.

[0167] Furthermore, the display unit of the imaging device or inkjet printer may have a touch panel function. The driving method for this touch panel function may be infrared, capacitive, resistive, or electromagnetic induction, and is not particularly limited. The display device may also be used as the display unit of a multifunction printer.

[0168] Next, the display device according to this embodiment will be described with reference to the drawings.

[0169] Figure 1 is a schematic cross-sectional view showing an example of a display device having an organic light-emitting element and a transistor connected to this organic light-emitting element. The transistor is an example of an active element. The transistor may also be a thin-film transistor (TFT).

[0170] Figure 1(a) shows an example of a pixel, which is a component of the display device according to this embodiment. The pixel has sub-pixels 10. The sub-pixels are divided into 10R, 10G, and 10B based on their light emission. The light 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 has a reflective electrode 2 which is a first electrode, an insulating layer 3 covering the end of the reflective electrode 2, an organic compound layer 4 covering the first electrode and the insulating layer, a transparent electrode 5, a protective layer 6, and a color filter 7 on an interlayer insulating layer 1.

[0171] The interlayer insulating layer 1 may have transistors and capacitive elements placed in the layer below or inside it. The transistor and the first electrode may be electrically connected via a contact hole or the like (not shown).

[0172] The insulating layer 3 is also called the bank or pixel isolation layer. It covers the edge of the first electrode and surrounds the first electrode. The portion without the insulating layer is in contact with the organic compound layer 4 and becomes the light-emitting region.

[0173] The organic compound layer 4 includes a hole injection layer 41, a hole transport layer 42, a first light-emitting layer 43, a second light-emitting layer 44, and an electron transport layer 45.

[0174] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0175] The protective layer 6 reduces the penetration of moisture into the organic compound layer. Although the protective layer is shown as a single layer, it may consist of multiple layers. Each layer may contain an inorganic compound layer and an organic compound layer.

[0176] The color filters 7 are classified into 7R, 7G, and 7B according to their color. The color filters may be formed on a planarization film (not shown). The color filters may also have a resin protective layer (not shown). Alternatively, the color filters may be formed on a protective layer 6, or they may be bonded together after being placed on an opposing substrate such as a glass substrate.

[0177] The display device 100 in Figure 1(b) shows an organic light-emitting element 26 and a TFT 18 as an example of a transistor. A substrate 11 made of glass, silicon, or the like is provided, with an insulating layer 12 on top of it. An active element 18 such as a TFT is placed on the insulating layer, and the gate electrode 13, gate insulating film 14, and semiconductor layer 15 of the active element are arranged therein. The active element 18 is also composed of a semiconductor layer 15, a drain electrode 16, and a source electrode 17. An insulating film 19 is provided on top of the active element 18. The anode 21 and the source electrode 17 that constitute the organic light-emitting element 26 are connected via a contact hole 20 provided in the insulating film.

[0178] Note that the method of electrical connection between the electrodes (anode, cathode) included in the organic light-emitting element 26 and the electrodes (source electrode, drain electrode) included in the TFT is not limited to the configuration shown in Figure 1(b). In other words, it is sufficient if either the anode or cathode is electrically connected to either the source electrode or the drain electrode of the TFT. TFT refers to a thin-film transistor.

[0179] In the display device 100 shown in Figure 1(b), the organic compound layer is depicted as a single layer, but the organic compound layer 22 may consist of multiple layers. A first protective layer 24 and a second protective layer 25 are provided on the cathode 23 to reduce the degradation of the organic light-emitting element.

[0180] In the display device 100 shown in Figure 1(b), a transistor is used as the switching element, but other switching elements may be used instead.

[0181] Furthermore, the transistor used in the display device 100 in Figure 1(b) is not limited to a transistor using a single-crystal silicon wafer, but may also be a thin-film transistor having an active layer on an insulating surface of the substrate. Examples of active layers 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. Thin-film transistors are also called TFT elements.

[0182] The transistors included in the display device 100 in Figure 1(b) may be formed within a substrate such as a Si substrate. Here, "formed within a substrate" means that the transistors are manufactured by processing the substrate itself, such as a Si substrate. In other words, having transistors within a substrate can be seen as the substrate and transistors being formed as a single unit.

[0183] The organic light-emitting element according to this embodiment has its luminescence controlled by a TFT, which is an example of a switching element, and by providing multiple organic light-emitting elements on the surface, an image can be displayed using the luminescence of each element. The switching element according to this embodiment is not limited to a TFT, but may also be a transistor made of low-temperature polysilicon, or an active matrix driver formed on a substrate such as a Si substrate. "On the substrate" can also mean "within the substrate." Whether to provide a transistor within the substrate or to use a TFT is selected depending on the size of the display area; for example, if the size is about 0.5 inches, it is preferable to provide the organic light-emitting element on a Si substrate.

[0184] FIG. 2 is a schematic diagram showing an example of a display device according to the present embodiment. The display device 1000 may have a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008 between an upper cover 1001 and a lower cover 1009. The display panel 1005 may have an organic light-emitting element according to the present embodiment. The touch panel 1003 and the display panel 1005 are respectively 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.

[0185] The display device according to the present embodiment may have a color filter having red, green, and blue. The color filter may have the red, green, and blue arranged in a delta array.

[0186] 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.

[0187] The display device according to the present embodiment may be used for a display unit of an imaging device having an imaging element that receives light. The imaging device may have a display unit that displays information acquired by the imaging element. Further, the display unit may be a display unit exposed outside the imaging device or a display unit disposed in a finder. The imaging device may be a digital camera or a digital video camera.

[0188] Figure 3(a) is a schematic diagram showing an example of an imaging device according to this embodiment. The imaging device 1100 may include a viewfinder 1101, a rear display 1102, an operating unit 1103, and a housing 1104. The viewfinder 1101 and the rear display 1102 may have organic light-emitting elements according to this embodiment. In that case, the viewfinder 1101 and the rear display 1102 may display not only the image to be captured, but also environmental information, imaging instructions, etc. Environmental information may include the intensity of ambient light, the direction of ambient light, the speed at which the subject is moving, the possibility of the subject being obscured by an obstacle, etc.

[0189] Since the optimal timing for imaging is very short, it is best to display the information as quickly as possible. Therefore, it is preferable to use a display device using the organic light-emitting element according to this embodiment, because organic light-emitting elements have a fast response speed.

[0190] The imaging device 1100 may further include an optical section (not shown). The lenses in the optical section may be one or more, and they form an image on the image sensor housed in the housing 1104. The focus can be adjusted by adjusting the relative positions of the multiple lenses. This operation can also be performed automatically. The imaging device may also be called a photoelectric converter. The photoelectric converter may not capture images sequentially, but may include methods of capturing images such as detecting the difference from the previous image or extracting from an image that is always being recorded.

[0191] Figure 3(b) is a schematic diagram showing an example of an electronic device according to this embodiment. The electronic device 1200 has a display unit 1201, an operation unit 1202, and a housing 1203. The housing 1203 may have a circuit, a printed circuit board having the circuit, a battery, and a communication unit. The operation unit 1202 may be a button or a touch panel type response unit. The operation unit may also be a biometric recognition unit that recognizes fingerprints to unlock or otherwise perform actions. An electronic device having a communication unit can also be called a communication device. The electronic device may further have a camera function by including a lens and an image sensor. Images captured by the camera function are displayed on the display unit. Examples of electronic devices include smartphones and laptop computers.

[0192] Figure 4 is a schematic diagram showing an example of a display device according to this embodiment. Figure 4(a) is a display device such as a television monitor or a PC monitor. The display device 1300 has a housing 1301 and a display unit 1302. An organic light-emitting element according to this embodiment may be used in the display unit 1302.

[0193] The display device 1300 may have a housing 1301 and a base 1303 that supports the display unit 1302. The base 1303 is not limited to the form shown in Figure 4(a). The lower edge of the housing 1301 may also serve as the base.

[0194] Furthermore, the housing 1301 and the display unit 1302 may be curved. Their radius of curvature may be between 5000 mm and 6000 mm.

[0195] Figure 4(b) is a schematic diagram showing another example of the display device according to this embodiment. The display device 1310 in Figure 4(b) is configured to be foldable and is a so-called foldable display device. The display device 1310 has a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may have organic light-emitting elements according to this embodiment. The first display unit 1311 and the second display unit 1312 may be a single display device without seams. The first display unit 1311 and the second display unit 1312 can be separated by a bending point. The first display unit 1311 and the second display unit 1312 may each display different images, or the first and second display units may together display a single image.

[0196] Figure 5(a) is a schematic diagram showing an example of a lighting device according to this embodiment. The lighting device 1400 may have a housing 1401, a light source 1402, and a circuit board 1403. The light source 1402 may have an organic light-emitting element according to this embodiment. The lighting device 1400 may have an optical film 1404 to improve the color rendering of the light source. The lighting device 1400 may also have a light diffusion section 1405 to effectively diffuse the light from the light source. The lighting device 1400 having a light diffusion section 1405 allows light to be delivered over a wide area. The optical film 1404 and the light diffusion section 1405 may be provided on the light-emitting side of the lighting. A cover may be provided on the outermost part as needed.

[0197] The lighting device is, for example, a device for illuminating a room. The lighting device may emit white light, daylight white light, or any other color from blue to red. The lighting device according to this embodiment may have a dimming circuit for adjusting the brightness of these colors. The lighting device according to this embodiment may also have a power supply circuit connected to the organic light-emitting element according to this embodiment. The power supply circuit may be a circuit that converts AC voltage to DC voltage. White light has a color temperature of 4200K, and daylight white light has a color temperature of 5000K. The lighting device according to this embodiment may further have a color filter.

[0198] Furthermore, the lighting device according to this embodiment may have a heat dissipation section. The heat dissipation section releases heat from inside the device to the outside, and examples include metals, ceramics, and the like with high thermal conductivity.

[0199] Figure 5(b) is a schematic diagram of an automobile, which is an example of a mobile body according to this embodiment. The automobile has a taillight, which is an example of a lighting device. The automobile 1500 has a taillight 1501 and a body 1503, and the taillight may illuminate when the brakes are applied or the like. The body 1503 can also be called the machine body. The automobile 1500 may have a window 1502 attached to the body 1503. The taillight 1501 may have an organic light-emitting element according to this embodiment. The taillight may have a protective member to protect the light source. The protective member has a reasonably high strength and can be made of any material as long as it is transparent, but it is preferably made of polycarbonate or the like. A franciocarboxylic acid derivative, an acrylonitrile derivative, or the like may be mixed with the polycarbonate.

[0200] Window 1502 may be a transparent display if it is not a window for checking the front and rear of the vehicle. The transparent display may have an organic light-emitting element according to this embodiment. In this case, the constituent materials such as electrodes of the organic light-emitting element according to the present invention are made of transparent material.

[0201] Furthermore, as shown in Figure 5(c), the automobile 1500 includes a steering wheel 1504 for controlling the direction of movement of the moving body, a display unit 1505 mounted on the vehicle body 1503 for displaying a map, the position of the moving body, the direction of turns, etc. The display unit 1505 may have an organic light-emitting element according to this embodiment.

[0202] The mobile body according to this embodiment includes a drive force generating unit that generates a driving force mainly used for the movement of the mobile body, and one or both of a rotating body mainly used for the movement of the mobile body. The drive force generating unit may be an engine, a motor, etc. The rotating body may be a tire, a wheel, a ship's propeller, etc. Specifically, it may be a bicycle, an automobile, a train, a ship, an aircraft, a drone, etc. The mobile body may have a body and a light fixture or display unit provided on the body. The light fixture may emit light to indicate the position of the body.

[0203] Referencing Figure 6, examples of applications of the display devices of each embodiment described above will be explained. The display device can be applied to systems that can be worn as wearable devices, such as smart glasses, head-mounted displays, and smart contact lenses. A display device that can be used in a wearable device may have an imaging device capable of photoelectric conversion of visible light and a display device capable of emitting visible light.

[0204] Figure 6 is a schematic diagram showing an example of eyeglasses (smart glasses) according to this embodiment. The eyeglasses 1600 (smart glasses) will be explained using Figure 6(a). The eyeglasses 1600 has a display unit on the back side of the lens 1601. The display unit may have an organic light-emitting element according to the present invention. Furthermore, an imaging device 1602 such as a CMOS sensor or SPAD may be provided on the front side of the lens 1601.

[0205] The eyeglasses 1600 further include a control device 1603. The control device 1603 functions as a power supply that provides power to the imaging device 1602 and the display unit. The control device 1603 also controls the operation of the imaging device 1602 and the display unit. The lens 1601 has an optical system formed therein for focusing light from the imaging device 1602 and the display unit.

[0206] Using FIG. 6(b), the glasses 1610 (smart glasses) will be described. The glasses 1610 have a control device 1612, and a display device having an organic light-emitting element according to the present invention is provided in the control device 1612. The control device 1612 may further have an imaging device corresponding to the imaging device 1602. An optical system for projecting light emitted from the control device 1612 is formed in the lens 1611, and an image is projected onto the lens 1611. The control device 1612 functions as a power source for supplying power to the imaging device and the display device, and controls the operations of the imaging device and the display device. The control device may have a line-of-sight detection unit that detects the line of sight of the wearer. The detection of the line of sight may use infrared rays. The infrared light-emitting unit emits infrared rays to the eyeball of the user who is gazing at the display image. Among the emitted infrared light, an imaging image of the eyeball is obtained by the imaging unit having a light-receiving element detecting the reflected light from the eyeball. By having a reduction means for reducing the light from the infrared light-emitting unit to the display unit in a plan view, the degradation of the image quality is reduced.

[0207] From the imaging image of the eyeball obtained by imaging the infrared light, the control device 1612 detects the user's line of sight with respect to the display image. Any known method can be applied to the line-of-sight detection using the imaging image of the eyeball. As an example, a line-of-sight detection method based on the Purkinje image by the reflection of the irradiation light on the cornea can be used.

[0208] More specifically, a line-of-sight detection process based on the pupil corneal reflection method is performed. Using the pupil corneal reflection method, a line-of-sight vector representing the orientation (rotation angle) of the eyeball is produced based on the image of the pupil and the Purkinje image included in the imaging image of the eyeball, whereby the user's line of sight is detected.

[0209] The display device according to the present embodiment has an imaging device having a light-receiving element, and may control the display image of the display device based on the user's line-of-sight information from the imaging device.

[0210] Specifically, the display device determines a first field of view that the user is fixated on, and a second field of view other than the first field of view, based on gaze information. The first and second field of view may be determined by the display device's control unit, or they may be determined by an external control unit and received by the display device. Within the display area of ​​the display device, the display resolution of the first field of view may be controlled to be higher than that of the second field of view. In other words, the resolution of the second field of view may be lower than that of the first field of view.

[0211] Furthermore, the display area has a first field of view and a second field of view different from the first field of view, and based on gaze information, a higher priority area is determined from the first and second field of view. The first and second field of view areas may be determined by the control device of the display device, or they may be determined by an external control device and received. The resolution of the higher priority area may be controlled to be higher than the resolution of the areas other than the higher priority area. In other words, the resolution of areas with relatively lower priority may be set lower.

[0212] AI may be used to determine the first field of view and the field of view with higher priority. The AI ​​may be a model configured to estimate the angle of gaze and the distance to the target object at the end of the line of sight from the image of the eye, using the image of the eye and the direction the eye was actually looking in the image as training data. The AI ​​may be included in the display device, the imaging device, or an external device. If the external device includes the AI, it can preferably be applied to smart glasses that further include an imaging device for capturing images of the outside. The smart glasses can display the captured external information in real time.

[0213] Figure 7(a) is a schematic diagram showing an example of an image forming apparatus according to this embodiment. 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 transfer unit 32, a transport roller 33, and a fuser 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 may have an organic light-emitting element according to this embodiment. The developing unit 31 has toner or the like. The charging unit 30 charges the photoreceptor 27. The transfer unit 32 transfers the developed image to a storage medium 34. The transport roller 33 transports the recording medium 34. The recording medium 34 is, for example, paper. The fuser 35 fixes the image formed on the recording medium 34.

[0214] Figures 7(b) and 7(c) are diagrams showing the exposure light source 28, schematic diagrams showing how multiple light-emitting units 36 are arranged on a long substrate. Arrows 37 indicate the direction of the column in which the organic light-emitting elements are arranged. This column direction is the same as the direction of the axis of rotation of the photoreceptor 27. This direction can also be called the long axis direction of the photoreceptor 27. Figure 7(b) shows a configuration in which the light-emitting units 36 are arranged along the long axis direction of the photoreceptor 27. Figure 7(c) is a different configuration from Figure 7(b), in which the light-emitting units 36 are arranged alternately in the column direction in the first and second columns. The first and second columns are located at different positions in the row direction. In the first column, multiple light-emitting units 36 are arranged with intervals between them. In the second column, light-emitting units 36 are located at positions corresponding to the intervals between the light-emitting units 36 in the first column. That is, multiple light-emitting units 36 are also arranged with intervals between them in the row direction. The arrangement in Figure 7(c) can also be described as a grid pattern, a houndstooth pattern, or a checkerboard pattern.

[0215] As described above, by using the device employing the organic light-emitting element according to this embodiment, stable display with good image quality is possible even during long-term display. [Examples]

[0216] The present invention will be described below with reference to examples. However, the present invention is not limited to these examples.

[0217] [Example 1 (Synthesis of Exemplary Compound A12)] The acenaphtho[1,2-k]benzo[e]acephenanthlene skeleton was synthesized according to the following synthesis procedure, with reference to the synthesis procedure described in Patent Document 1.

[0218] [ka]

[0219] (1) Synthesis of compound E3 The following reagents and solvents were placed in a 100 ml round-bottom flask. Compound E1: 2.00g (7.66mmol) Compound E2: 1.69g (8.04mmol) Ethanol: 40ml Next, 556 mg (8.43 mmol) of 85% sodium hydroxide was dissolved in 10 ml of ethanol, and this solution was added dropwise to the round-bottom flask at room temperature. After the addition was complete, the flask was heated to 40°C under a nitrogen stream and stirred for 10 hours. After the reaction was complete, water was added to the reaction solution, filtered, and washed with water and methanol to obtain 3.07 g (yield: 92%) of the dark green compound E3.

[0220] (2) Synthesis of compound E5 The following reagents and solvents were placed in a 100 ml round-bottom flask. Compound E3: 3.00g (6.89mmol) Compound E4: 1.98g (7.58mmol) Isoamyl nitrite: 1.02 ml (7.58 mmol) Toluene: 50ml Next, the reaction solution was heated to 105°C under a nitrogen stream and stirred for 2 hours. Furthermore, 669 mg (2.56 mmol) of compound E4 and 0.34 ml (2.56 mmol) of isoamyl nitrite were added to the reaction solution and stirred for 2 hours. After the reaction was complete, the solution was extracted with toluene and water, concentrated, purified by silica gel column chromatography (heptane:toluene = 4:1), and then dispersed and washed with heptane / ethanol to obtain 1.41 g (yield: 47%) of the yellow compound E5.

[0221] [ka]

[0222] (3) Synthesis of compound E8 The following reagents and solvents were placed in a 300 ml round-bottom flask. Compound E6: 2.00g (16.4mmol) Compound E7: 5.89g (16.4mmol) Toluene: 60ml Ethanol: 30ml 10% sodium carbonate aqueous solution: 30 ml Tetrakis(triphenylphosphine)palladium: 94.7 mg (0.82 mmol) Next, the reaction solution was heated to 90°C under a nitrogen stream and stirred for 2 hours. After the reaction was complete, the solution was extracted with toluene, concentrated, and purified by silica gel column chromatography (heptane:toluene mixture) to obtain 5.51 g of colorless compound E8 (yield: 87%).

[0223] (4) Synthesis of compound E10 The following reagents and solvents were placed in a 200 ml round-bottom flask. Compound E8: 2.00 g (6.47 mmol) Compound E9: 1.64g (6.47mmol) Pd(OAc)2: 72.6 mg (0.32 mmol) SPhos: 63.4 mg (0.65 mmol) KOAc: 3.32g (33.9mmol) Toluene: 60ml Next, the reaction solution was heated to 90°C under a nitrogen atmosphere and stirred for 3 hours. After the reaction was complete, the solution was extracted with toluene, concentrated, and purified by silica gel column chromatography (toluene) to obtain 1.73 g of colorless compound E10 (yield: 75%).

[0224] [ka]

[0225] (5) Synthesis of compound A12 The following reagents and solvents were placed in a 100 ml round-bottom flask. Compound E5: 0.5g (0.82mmol) Compound E10:0.29g(0.83mmol) Pd(OAc)2: 9.20 mg (0.04 mmol) SPhos: 33.6 mg (0.082 mmol) KOAc: 0.40g (4.10 mmol) Toluene: 20ml Next, the reaction solution was heated to 90°C under a nitrogen stream and stirred for 3 hours. After the reaction was complete, the solution was extracted with toluene, concentrated, and purified by silica gel column chromatography (heptane:toluene mixture) to obtain 0.34 g of yellow compound A11 (yield: 55%).

[0226] The example compound A11 was subjected to mass spectrometry using MALDI-TOF-MS (Bruker Autoflex LRF).

[0227] [MALDI-TOF-MS] Measured value: m / z = 756 Calculated value: C 60 H 36 =756 (Synthesis of example compound D27)

[0228] [ka]

[0229] (6) Synthesis of compound E13 The following reagents and solvents were placed in a 300 ml three-necked flask. Compound E11: 10.00g (0.05mol) Compound E12: 13.2g (0.06mol) 1,2-Dimethoxyethane: 100 ml 2M sodium carbonate aqueous solution: 40 ml Tetrakis(triphenylphosphine)palladium: 2.88g (5.0 mmol) Next, the reaction solution was heated to 90°C under a nitrogen atmosphere and stirred for 7 hours. After the reaction was complete, the solution was extracted with toluene and then concentrated to obtain 18.8 g of compound E13 (yield: 95%).

[0230] (7) Synthesis of compound E14 The following reagents and solvents were placed in a 500 ml three-necked flask. Compound E13: 13.00 g (0.03 mol) Compound E9: 15.6g (0.06mol) Pd(OAc)2: 0.90g (0.4 mmol) SPhos: 0.49g (1.2 mmol) KOAc: 3.32g (0.12mol) Toluene: 300ml Next, the reaction solution was heated to 90°C under a nitrogen stream and stirred for 5 hours. After the reaction was complete, the solution was filtered through silica gel and washed with toluene to obtain 12.8 g of compound E14 (yield: 88%).

[0231] [ka]

[0232] (8) Synthesis of compound E16 The following reagents and solvents were placed in a 500 ml three-necked flask. Compound E15: 2.00g (2.78mmol) Compound E14: 2.04 g (4.17 mmol) Toluene: 100ml 2M sodium carbonate solution: 10 ml Tetrakis(triphenylphosphine)palladium: 0.19g (0.14 mmol) Next, the reaction solution was heated to 90°C under a nitrogen stream and stirred for 15 hours. After the reaction was complete, it was filtered through silica gel and washed with toluene. Then, it was concentrated, washed with methanol, and filtered to obtain 1.89 g of the yellow compound E16 (yield: 68%).

[0233] [ka]

[0234] (9) Synthesis of compound E17 The reagents and solvents listed below were placed in a 500 ml three-necked flask. The reaction was carried out under a nitrogen atmosphere. (Methoxymethyl)triphenylphosphonium chloride: 0.48g (2.53 mmol) THF (dehydration): 75mL Next, 1.0 M / L t-BuOK / THF: 0.28 g (2.53 mmol) / 2.53 mM THF was added and the mixture was stirred for 2 hours.

[0235] Next, a solution of compound E15: 1.69 g (1.69 mmol) in THF (anhydrous): 75 mL was added, and the mixture was heated and stirred for 2 hours.

[0236] After quenching with water, the mixture was extracted with toluene. The organic layer was concentrated, and the resulting residue was purified by silica gel column chromatography (heptane:toluene mixture). The resulting solid was suspended and washed with methanol, and filtered to obtain 1.56 g of the yellow compound E16 (yield: 90%).

[0237] [ka]

[0238] (10) Synthesis of compound D27 The reagents and solvents listed below were placed in a 500 ml three-necked flask. The reaction was carried out under a nitrogen atmosphere. Compound E16: 1.5g (1.5mmol) Dichloromethane: 50ml 0.14 g (1.5 mmol) of methanesulfonic acid was added dropwise, and the mixture was stirred for 1 hour. After quenching with aqueous sodium bicarbonate solution, the mixture was extracted with dichloromethane. The organic layer was concentrated and purified by silica gel chromatography (heptane:toluene mixture). The resulting solid was washed with methanol suspension and filtered to obtain 1.14 g (yield: 76%) of the yellow compound A10.

[0239] The example compound A10 was subjected to mass spectrometry using MALDI-TOF-MS (Bruker Autoflex LRF).

[0240] [MALDI-TOF-MS] Measured value: m / z = 997 Calculated value: C 78 H 60 =997 [Examples 2 to 63 (Synthesis of Exemplary Compounds)] As shown in Table 6, the exemplary compounds shown in Examples 2 to 62 were synthesized in the same manner as in Example 1, except that raw material E5 in Example 1 was replaced with raw material 1, and raw material E10 was replaced with raw material 2.

[0241] Furthermore, the measured values ​​(m / z) of the mass spectrometry results, measured in the same manner as in Example 1, are shown.

[0242] [Table 6-1]

[0243] [Table 6-2]

[0244] [Table 6-3]

[0245] [Table 6-4]

[0246] [Table 6-5]

[0247] [Table 6-6]

[0248] [Table 6-7]

[0249] [Table 6-8]

[0250] [Table 6-9]

[0251] [Table 6-10]

[0252] [Example 64] In this embodiment, an organic EL element with a bottom emission structure was fabricated on a substrate, in which an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an emissive layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode were sequentially formed.

[0253] First, an ITO film was deposited on a glass substrate, and an ITO electrode (anode) was formed by applying a desired patterning process. At this time, the film thickness of the ITO electrode was set to 100 nm. The substrate on which the ITO electrode was formed in this way was used as the ITO substrate in the following steps. Next, the organic compound layer and electrode layer shown in Table 7 were continuously deposited on the ITO substrate by vacuum deposition using resistance heating in a vacuum chamber. At this time, the electrode area of ​​the opposing electrodes (metal electrode layer, cathode) was 3 mm². 2 I made it so that it would be like that.

[0254] [Table 7]

[0255] The characteristics of the obtained elements were measured and evaluated. The maximum current efficiency of the light-emitting element was 1.1, compared to the efficiency ratio of Comparative Example 1, which was set to 1.0. The luminance of the light-emitting element was 1000 cd / m². 2 The emission spectrum of Comparative Example 1 was found to be 460 nm. Specifically, the current-voltage characteristics were measured using a Hewlett-Packard 4140B microammeter, and the luminescence intensity was measured using a Topcon BM7.

[0256] [Examples 65 to 87, Comparative Example 1 and Comparative Example 2] In Examples 65 to 87, Comparative Example 1, and Comparative Example 2, organic light-emitting devices were fabricated in the same manner as in Example 64, except that the compounds shown in Table 8 were appropriately changed. The characteristics of the obtained devices were measured and evaluated in the same manner as in Example 64. The measurement results are shown in Table 8.

[0257] A and B in the table are as follows: A: Emission wavelength is 455nm or less B: Emission wavelength is between 456nm and 460nm C: Emission wavelength of 460 nm or higher

[0258] [Table 8]

[0259] Table 8 shows that the organic light-emitting element according to the example exhibits superior luminescence efficiency and emission wavelength compared to the organic light-emitting element according to the comparative example. This is thought to be because by providing specific substituents along the long axis of the organic compound according to this embodiment, which is the guest material, it was possible to achieve both improved horizontal orientation and reduced π-conjugation elongation.

[0260] For the reasons stated above, the organic compound according to the present invention is an organic compound with excellent luminescence efficiency and color purity.

[0261] Furthermore, the present invention can also take the following configuration.

[0262] (Composition 1) An organic compound characterized by being represented by the general formula [1].

[0263] [ka]

[0264] In the general formula [1], R1 to R 27 Each of these is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted amino group, and a cyano group. 21 and R 24 , and, R 22 and R 27 At least one of them may be joined to form a ring.

[0265] Ar is a substituted or unsubstituted aryl group.

[0266] n is an integer between 1 and 5 (inclusive).

[0267] L is one of the general formulas [2] through [7], or a combination thereof. When n is an integer greater than or equal to 2, multiple Ls may be the same or different.

[0268] [ka]

[0269] In general formulas [2] through [7], R 101 ~R 138 , R a , and R b R is independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aryl group. a and R b These atoms may bond to form a ring. X is an oxygen atom or a sulfur atom. * indicates a bond position.

[0270] (Configuration 2) In the general formula [1], R1 to R 27 The organic compound according to configuration 1, characterized in that each of the elements is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.

[0271] (Composition 3) In general formula (1), R1 to R 27 The organic compound according to configuration 1 or 2, characterized in that each is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0272] (Composition 4) In general formula (1), R1 to R 27The organic compound is one of any three configurations, each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a CD3 group, an iso-propyl group, a tert-butyl group, C(CH3)2(C2H5), C(CH3)(C2H5)2, and a phenyl group.

[0273] (Composition 5) The organic compound according to any one of configurations 1 to 4, characterized in that, in general formula (1), Ar is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0274] (Composition 6) The organic compound according to any one of configurations 1 to 5, characterized in that, in general formula (1), Ar is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0275] (Composition 7) In general formula (1), R1, R3, R5, R 11 , R 14 , R 16 , R 18 , R 24 , and R 27 An organic compound according to any one of configurations 1 to 6, characterized in that at least one of them is a non-hydrogen atom.

[0276] (Composition 8) In general formula (1), R 24 and R 27 An organic compound according to any one of configurations 1 to 7, characterized in that at least one of them is a substituted or unsubstituted alkyl group.

[0277] (Composition 9) In general formula (1), R 24 and R 27 An organic compound according to any one of configurations 1 to 8, characterized in that the group is a methyl group.

[0278] (Composition 10) In general formula (1), R1, R5, R 14 , and R 18The organic compound according to any one of configurations 1 to 9, characterized in that at least one of them is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0279] (Composition 11) In general formula (1), R1, R5, R 14 , and R 18 An organic compound according to any one of configurations 1 to 10, characterized in that at least one of the members is a methyl group or a phenyl group.

[0280] (Composition 12) In general formula (1), R3 and R 16 An organic compound according to any one of configurations 1 to 11, characterized in that at least one of them is a substituted or unsubstituted alkyl group.

[0281] (Composition 13) The first electrode and the second electrode, An organic light-emitting element having an organic compound layer disposed between the first electrode and the second electrode, The organic light-emitting element is characterized in that the organic compound layer has an organic compound as described in any of configurations 1 to 12.

[0282] (Composition 14) The aforementioned organic compound layer has a light-emitting layer, The organic light-emitting element according to configuration 13, characterized in that the light-emitting layer has the organic compound.

[0283] (Composition 15) The light-emitting layer further comprises the first compound, The organic light-emitting element according to configuration 14, characterized in that the lowest singlet excitation energy of the first compound is higher than the lowest singlet excitation energy of the organic compound.

[0284] (Composition 16) The organic light-emitting element according to configuration 15, characterized in that the first compound comprises a hydrocarbon compound.

[0285] (Composition 17) The light-emitting layer further comprises a second compound, The organic light-emitting element according to configuration 15 or 16, characterized in that the lowest excited singlet energy of the second compound is higher than the lowest excited singlet energy of the organic compound and lower than the lowest excited singlet energy of the first compound.

[0286] (Composition 18) A display device having a plurality of pixels, wherein at least one of the plurality of pixels comprises an organic light-emitting element according to any one of configurations 13 to 17 and a transistor connected to the organic light-emitting element.

[0287] (Composition 19) It has an image sensor that receives light and a display unit that displays the image captured by the image sensor, The photoelectric conversion device is characterized in that the display unit has an organic light-emitting element as described in any of configurations 13 to 17.

[0288] (Composition 20) An image display device characterized by comprising a display unit having an organic light-emitting element as described in any of configurations 13 to 17, and a housing on which the display unit is provided.

[0289] (Composition 21) An electronic device comprising: a display unit having an organic light-emitting element as described in any of configurations 13 to 17; a housing on which the display unit is provided; and a communication unit provided in the housing for communicating with the outside.

[0290] (Composition 22) A wearable device comprising: a display unit having an organic light-emitting element as described in any of configurations 13 to 17; an optical system for focusing light from the display unit; and a control device for controlling the display of the display unit.

[0291] (Composition 23) A lighting device characterized by comprising a light source having an organic light-emitting element as described in any of configurations 13 to 17, and a housing on which the light source is provided.

[0292] (Composition 24) A mobile body characterized by comprising a lamp having an organic light-emitting element as described in any of configurations 13 to 17, and a body on which the lamp is provided. [Explanation of symbols]

[0293] Single-layer insulating layer 2 reflective electrode 3. Insulating layer 4 Organic compound layer 5 Transparent electrode 6 Protective layer 7 Color Filters 10 subpixels 11 circuit boards 12 Insulating layer 13 gates 14 Gate insulating film 15 Semiconductor layer 16 Drain electrode 17 Source electrodes 18 Thin-film transistors 19 Insulating film 20 contact holes 21 Lower electrode 22 Organic compound layer 23 Upper electrode 24 First protective layer 25 Second protective layer 26 Organic light-emitting diodes 27 Photoreceptor 28 Exposure light source 29 light 30 Charged parts 31. Developing Department 32 Transfer section 33 Conveying section 34 Recording media 35 Fixing section 36 Light-emitting part 37. First direction parallel to the long axis of the photoreceptor. 40 Image forming apparatus 100 display device 1000 display devices 1001 Top cover 1002 Flexible Printed Circuits 1003 Touch Panel 1004 Flexible Printed Circuit 1005 Display Panel 1006 Frame 1007 Circuit board 1008 Battery 1009 Lower cover 1100 Imaging device 1101 Viewfinder 1102 Rear display 1103 Operation section 1104 cabinet 1200 Electronic equipment 1201 Display section 1202 Operation unit 1203 enclosure 1300 display device 1301 Picture frame 1302 Display section 1303 Base 1310 Display device 1311 First display section 1312 Second display section 1313 cabinet 1314 Inflection point 1400 Lighting devices 1401 cabinet 1402 Light source 1403 Circuit board 1404 Optical Film 1405 Light Diffusion Section 1500 cars 1501 Taillight 1502 Window 1503 Body 1600 Smart Glasses 1601 Lens 1602 Imaging device 1603 Control device 1610 Smart Glasses 1611 Lens 1612 Control device

Claims

1. An organic compound characterized by being represented by general formula [1]. 【Chemistry 1】 In general formula [1], R １ ~R ２７ Each of these is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted amino group, and a cyano group. ２１ and R ２４ , and, R ２２ and R ２７ At least one of them may be joined to form a ring. Ar is a substituted or unsubstituted aryl group. n is an integer between 1 and 5 (inclusive). L is one of the general formulas [2] through [7], or a combination thereof. When n is an integer greater than or equal to 2, multiple Ls may be the same or different. 【Chemistry 2】 In general formulas [2] to [7], R １０１ to R １３８ , R ａ , and R ｂ are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aryl group. R ａ and R ｂ may combine to form a ring. X is an oxygen atom or a sulfur atom. * is the bonding position.

2. In general formula [1], R １ ~R ２７ The organic compound according to claim 1, characterized in that each of the members is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.

3. In general formula (1), R １ ~R ２７ The organic compound according to claim 1, characterized in that each of the following is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

4. In general formula (1), R １ ~R ２７ This consists of a hydrogen atom, a deuterium atom, a methyl group, and CD. ３ group, iso-propyl group, tert-butyl group, C(CH ３ ) ２ (C ２ H ５ ), C (CH ３ ) (C ２ H ５ ) ２ The organic compound according to claim 1, which is independently selected from the group consisting of a phenyl group and a phenyl group.

5. The organic compound according to claim 1, characterized in that in general formula (1), Ar is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

6. The organic compound according to claim 1, characterized in that in general formula (1), Ar is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

7. In general formula (1), R １ , R ３ , R ５ , R １１ , R １４ , R １６ , R １８ , R ２４ , and R ２７ The organic compound according to claim 1, characterized in that at least one of them is a non-hydrogen atom.

8. In general formula (1), R ２４ and R ２７ The organic compound according to claim 1, characterized in that at least one of them is a substituted or unsubstituted alkyl group.

9. In general formula (1), R ２４ and R ２７ The organic compound according to claim 1, characterized in that is a methyl group.

10. In general formula (1), R １ , R ５ , R １４ , and R １８ The organic compound according to claim 1, characterized in that at least one of them is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

11. In general formula (1), R １ , R ５ , R １４ , and R １８ The organic compound according to claim 1, characterized in that at least one of them is a methyl group or a phenyl group.

12. In general formula (1), R ３ and R １６ The organic compound according to claim 1, characterized in that at least one of them is a substituted or unsubstituted alkyl group.

13. The first electrode and the second electrode, An organic light-emitting element having an organic compound layer disposed between the first electrode and the second electrode, The organic light-emitting element is characterized in that the organic compound layer has the organic compound described in claim 1.

14. The aforementioned organic compound layer has a light-emitting layer, The organic light-emitting element according to claim 13, characterized in that the light-emitting layer has the organic compound.

15. The light-emitting layer further comprises the first compound, The organic light-emitting element according to claim 14, characterized in that the lowest singlet excitation energy of the first compound is higher than the lowest singlet excitation energy of the organic compound.

16. The organic light-emitting element according to claim 15, characterized in that the first compound comprises a hydrocarbon compound.

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

18. A display device having a plurality of pixels, wherein at least one of the plurality of pixels comprises an organic light-emitting element according to any one of claims 13 to 17 and a transistor connected to the organic light-emitting element.

19. It has an image sensor that receives light and a display unit that displays the image captured by the image sensor, The photoelectric conversion device is characterized in that the display unit has an organic light-emitting element as described in any one of claims 13 to 17.

20. An image display device comprising a display unit having an organic light-emitting element as described in any one of claims 13 to 17, and a housing on which the display unit is provided.

21. An electronic device comprising: a display unit having an organic light-emitting element as described in any one of claims 13 to 17; a housing on which the display unit is provided; and a communication unit provided in the housing for communicating with the outside.

22. A wearable device comprising: a display unit having an organic light-emitting element as described in any one of claims 13 to 17; an optical system for focusing light from the display unit; and a control device for controlling the display of the display unit.

23. A lighting device comprising a light source having an organic light-emitting element as described in any one of claims 13 to 17, and a housing on which the light source is provided.

24. A mobile body comprising a lamp having an organic light-emitting element as described in any one of claims 13 to 17, and a body on which the lamp is provided.

Images