Organic metal complex and organic light-emitting element

Abstract

To provide an organic metal complex that emits red light with a high color purity.SOLUTION: For example, an organic metal complex B5 is synthesized by a reaction formula below.SELECTED DRAWING: None

Description

[Technical field]

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

[0002] An organic light-emitting element (also called an organic electroluminescence element (organic EL element)) is an electronic element having a pair of electrodes and an organic compound layer disposed between the electrodes. By injecting electrons and holes from the pair of electrodes, excitons of a light-emitting organic compound in the organic compound layer are generated, and when the excitons return to the ground state, the organic light-emitting element emits light. Recent progress in organic light-emitting devices has been remarkable, including low driving voltage, diverse emission wavelengths, high-speed response, and the possibility of making light-emitting devices thinner and lighter. In addition, the sRGB and AdobeRGB standards are used to represent the color reproduction range of displays, and materials that can reproduce these have been in demand. Recently, however, BT-2020 has been cited as a standard that will further expand the color reproduction range. Currently, the use of phosphorescence has been proposed as an attempt to improve the luminous efficiency of organic EL elements. In theory, organic EL elements using phosphorescence are expected to have about four times the luminous efficiency of those using fluorescence. Therefore, phosphorescent organometallic complexes have been actively created up to now. This is because the creation of organometallic complexes with excellent luminous properties is important in providing high-performance organic light-emitting elements. As an organometallic complex that has been created so far, the following compound 1-a is described in Patent Document 1.

[0003] [ka] [Prior art documents] [Patent documents]

[0004] [Patent Document 1] JP 2009-114137 A Summary of the Invention [Problem to be solved by the invention]

[0005] The organic light-emitting device using the compound described in Patent Document 1 is capable of emitting light with good luminous efficiency and color purity, but further improvements are required in terms of the high color purity, high efficiency, and high durability required for BT-2020. The present invention has been made in view of the above problems, and an object of the present invention is to provide an organometallic complex that emits red light with high color purity. [Means for solving the problem]

[0006] The organometallic complex according to one embodiment of the present invention is An organometallic complex represented by the following general formula [1]: Ir(L) m (L') n [1] In formula [1], Ir is iridium. L and L' each represent a different bidentate ligand. m is 1 or 2, and m+n=3. Substructure Ir(L) m is a partial structure represented by the following general formula [2-1] or [2-2].

[0007] [ka] In formula [2-1], R1 to R3 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. However, when at least one of R1 to R3 is not a hydrogen atom or a deuterium atom, and two of R1 to R3 are hydrogen atoms or deuterium atoms, the other of R1 to R3 is a substituted or unsubstituted secondary or higher alkyl group. Adjacent R1 to R3 may be bonded to each other to form a ring. R4 to R 14 are each independently selected from 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 silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted allyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, and a cyano group. 14 may be bonded to each other to form a ring. In formula [2-2], R 15 ~R 17 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. 15 ~R 17 At least one of the atoms is not a hydrogen atom or a deuterium atom, and R 15 ~R 17 If two of are hydrogen or deuterium atoms, R 15 ~R 17 The other of the R is a substituted or unsubstituted secondary or higher alkyl group. 15 ~R 17 may be bonded to each other to form a ring. R 18 ~R 30are each independently selected from 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 silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted allyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, and a cyano group. 18 ~R 30 may be bonded to each other to form a ring. L' is a bidentate ligand represented by the following general formula [3] or [4].

[0008] [ka] In formula [3], R 41 ~R 43 are each independently selected from a hydrogen atom, a deuterium atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. 41 ~R 43 may be bonded to each other to form a ring. In formula [4], R 32 ~R 39 are each independently selected from a hydrogen atom, a deuterium atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted allyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. 32 ~R 39 may be bonded to each other to form a ring. Effect of the Invention

[0009] According to the present invention, it is possible to provide an organometallic complex capable of emitting red light with high efficiency and high color purity. [Brief description of the drawings]

[0010] [Figure 1] FIG. 2 is a diagram showing optimized structures and half-widths of emission spectra of example compounds and comparative compounds. [Diagram 2] FIG. 2 is a diagram showing optimized structures and half-widths of emission spectra of example compounds and comparative compounds. [Diagram 3] FIG. 1 is a diagram showing the ratio of EQE (external quantum efficiency) between an example compound and a comparative compound, and the ratio of luminance degradation rate due to continuous driving. [Figure 4] 1A is a schematic cross-sectional view showing an example of a pixel of a display device according to one embodiment of the present invention, and FIG. 1B is a schematic cross-sectional view showing an example of a display device using an organic light-emitting element according to one embodiment of the present invention. [Diagram 5] FIG. 1 is a schematic diagram illustrating an example of a display device according to an embodiment of the present invention. [Figure 6] 1A is a schematic diagram illustrating an example of an imaging device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram illustrating an example of an electronic device according to an embodiment of the present invention. [Figure 7] 1A is a schematic diagram illustrating an example of a display device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram illustrating an example of a foldable display device. [Figure 8] 1A is a schematic diagram showing an example of an illumination device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram showing an example of a moving body having a vehicle lamp according to an embodiment of the present invention. [Figure 9] 1A is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram showing another example of a wearable device according to an embodiment of the present invention. [Figure 10] 1A is a schematic diagram illustrating an example of an image forming apparatus according to an embodiment of the present invention, and FIG. 1B is a schematic diagram illustrating an example of an exposure light source of the image forming apparatus according to an embodiment of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0011] <Organometallic Complexes> The organometallic complex according to this embodiment is represented by the following general formula [1].

[0012] Ir(L) m (L') n [1]

[0013] In formula [1], Ir is iridium. L and L' each represent a different bidentate ligand. m is 1 or 2, and m+n=3. When there are a plurality of L or L', the plurality of L' or L' may be the same or different. In addition, in the organometallic complex according to another embodiment, the ligands coordinated to the iridium metal may be different from each other. For example, it may be an organometallic complex having a partial structure shown in general formula [2-1] or [2-2], and having a ligand shown in general formula [3] and a ligand shown in general formula [4].

[0014] <Substructure Ir(L) m > Substructure Ir(L) m is a partial structure represented by the following general formula [2-1] or [2-2].

[0015] [ka]

[0016] [R1 to R3, R 15 ~R 17 ] In formula [2-1], R1 to R3 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. However, when at least one of R1 to R3 is not a hydrogen atom or a deuterium atom, and two of R1 to R3 are hydrogen atoms or deuterium atoms, the other of R1 to R3 is a substituted or unsubstituted secondary or higher alkyl group. At least two of R1 to R3 are preferably not a hydrogen atom or a deuterium atom, and are preferably substituted or unsubstituted alkyl groups.

[0017] In formula [2-2], R 15 ~R 17 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. 15 ~R 17 At least one of the atoms is not a hydrogen atom or a deuterium atom, and R 15 ~R 17 If two of are hydrogen or deuterium atoms, R 15 ~R 17 The other of R is a substituted or unsubstituted secondary or higher alkyl group. 15 ~R 18 At least two of the groups are preferably not hydrogen atoms or deuterium atoms, and are preferably substituted or unsubstituted alkyl groups.

[0018] The alkyl group is preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an i-pentyl group, a tert-pentyl group, a neopentyl group, a 3-pentyl group, an n-hexyl group, and a cyclohexyl group. Of these, a methyl group, an i-propyl group, and a tert-butyl group are more preferred.

[0019] Specific examples of the alkoxy group include a methoxy group, an ethoxy group, an i-propoxy group, an n-butoxy group, and a tert-butoxy group, with a methoxy group being preferred.

[0020] Examples of the silyl group include, but are not limited to, a trimethylsilyl group and a triphenylsilyl group.

[0021] Specific examples of the aryl group include a phenyl group, a naphthyl group, a phenanthryl group, an anthryl group, a fluorenyl group, a biphenylenyl group, an acenaphthylenyl group, a chrysenyl group, a pyrenyl group, a triphenylenyl group, a picenyl group, a fluoranthenyl group, a perylenyl group, a naphthacenyl group, a biphenyl group, and a terphenyl group. Among these, a phenyl group, a naphthyl group, a fluorenyl group, or a biphenyl group is preferable, and a phenyl group is more preferable.

[0022] Specific examples of the heteroaryl group include a thienyl group, a pyrrolyl group, a pyrazinyl group, a pyridyl group, an indolyl group, a quinolyl group, an isoquinolyl group, a naphthyridinyl group, an acridinyl group, a phenanthrolinyl group, a carbazolyl group, a benzo[a]carbazolyl group, a benzo[b]carbazolyl group, a benzo[c]carbazolyl group, a phenazinyl group, a phenoxazinyl group, a phenothiazinyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzofuranyl group, a dibenzofuranyl group, an oxazolyl group, and an oxadiazolyl group.

[0023] The substituents that may be further substituted by the alkyl group, alkoxy group, silyl group, aryl group, and heteroaryl group are not particularly limited, and examples thereof include alkyl groups such as deuterium atom, fluorine atom, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, i-pentyl group, tert-pentyl group, neopentyl group, n-hexyl group, and cyclohexyl group; methoxy group, ethoxy group, i-propoxy group, n-butoxy group, and tert-butoxy group. Alkoxy groups; 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-dibenzylamino 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-dianisolylamino group, N-mesityl-N-phenylamino group amino groups such as arylamino group, N,N-dimesitylamino group, N-phenyl-N-(4-tert-butylphenyl)amino group, and N-phenyl-N-(4-trifluoromethylphenyl)amino group; aryl groups such as phenyl group, naphthyl group, phenanthryl group, anthryl group, fluorenyl group, biphenylenyl group, acenaphthylenyl group, chrysenyl group, pyrenyl group, triphenylenyl group, picenyl group, fluoranthenyl group, perylenyl group, naphthacenyl group, biphenyl group, and terphenyl group; aryl groups such as thienyl group, pyrrolyl group, pyrazinyi group, Examples of the heterocyclic groups include a phenyl group, a pyridyl group, an indolyl group, a quinolyl group, an isoquinolyl group, a naphthyridinyl group, an acridinyl group, a phenanthrolinyl group, etc., a carbazolyl group, a benzo[a]carbazolyl group, a benzo[b]carbazolyl group, a benzo[c]carbazolyl group, a phenazinyl group, a phenoxazinyl group, a phenothiazinyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzofuranyl group, a dibenzofuranyl group, an oxazolyl group, an oxadiazolyl group, etc.; a cyano group, a trifluoromethyl group, a thiol group, etc. The hydrogen atoms of these optional substituents may be replaced with deuterium atoms.

[0024] Substituents that the alkyl group, alkoxy group, silyl group, aryl group and heteroaryl group may further have are preferably a deuterium atom, a methyl group, an i-propyl group, a tert-butyl group, a methoxy group, an N,N-dimethylamino group, an N,N-diphenylamino group, a phenyl group, a naphthyl group, a fluorenyl group, a biphenyl group and a terphenyl group, and particularly preferably a deuterium atom, a methyl group, an i-propyl group, a tert-butyl group and a phenyl group.

[0025] Adjacent R1 to R3 may be bonded to each other to form a ring, and adjacent R 15 ~R 17 may be bonded to each other to form a ring. Specifically, for example, adjacent R1 to R3 or adjacent R 15 ~R 17 may be bonded to each other to form a cycloalkyl group such as a cyclohexyl group.

[0026] [R4 to R 14 , R 18 ~R 30 ] In formula [2-1], R4 to R 14 are each independently selected from 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 silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted allyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, and a cyano group. R5 is preferably not a hydrogen atom or a deuterium atom, and is preferably the same group as -CR1(R2)(R3).

[0027] In formula [2-2], R 18 ~R 30are each independently selected from 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 silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted allyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, and a cyano group. 19 is preferably not a hydrogen atom or a deuterium atom, -CR 15 (R 16 )(R 17 ) is preferably the same group as

[0028] R4 to R 14 , R 18 ~R 30 The alkyl group, alkoxy group, silyl group, aryl group, and heteroaryl group represented by the formula: 15 ~R 17 Examples of the above-mentioned methods are the same as those described above.

[0029] Specific examples of the amino group include 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-dibenzylamino 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-dianisolylamino group, N-mesityl-N-phenylamino group, N,N-dimesitylamino group, N-phenyl-N-(4-tertiary butylphenyl)amino group, and N-phenyl-N-(4-trifluoromethylphenyl)amino group. Among these, N,N-dimethylamino group or N,N-diphenylamino group is preferred.

[0030] Examples of aryloxy groups include, but are not limited to, phenoxy and naphthoxy groups.

[0031] Examples of heteroaryloxy groups include, but are not limited to, furanyloxy groups and thienyloxy groups.

[0032] R4 to R 14 , R 18 ~R 30 The alkyl group, alkoxy group, silyl group, amino group, allyl group, aryl group, heteroaryl group, aryloxy group, and heteroaryloxy group represented by the formula (I) may further have a substituent, which may be R1 to R3, R 15 ~R 17 Examples of the above-mentioned methods are the same as those described above.

[0033] Adjacent R4 to R 14 may be bonded to each other to form a ring, and adjacent R 18 ~R 30 may be bonded to each other to form a ring. Bonding to each other to form a ring means that the ring formed by bonding adjacent R to each other and the ring to which the adjacent R are bonded form a condensed ring. The ring formed by bonding R to each other may be an aromatic ring.

[0034] <L’> L' is a bidentate ligand represented by the following general formula [3] or [4].

[0035] [ka]

[0036] [R 41 ~R 43 ] In formula [3], R 41 ~R 43 are each independently selected from a hydrogen atom, a deuterium atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. 41 ~R 43is preferably a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group. 41 ~R 43 may be bonded to each other to form a ring.

[0037] R 41 ~R 43 The alkyl group, alkoxy group, amino group, aryl group, and heteroaryl group represented by the formula: 15 ~R 17 , R4 to R 14 , R 18 ~R 30 The substituents which the alkyl group, the alkoxy group, the amino group, the aryl group, and the heteroaryl group may further have include R1 to R3, R 15 ~R 17 Examples of the above-mentioned methods are the same as those described above.

[0038] [R 32 ~R 39 ] In formula [4], R 32 ~R 39 are each independently selected from a hydrogen atom, a deuterium atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.

[0039] R 32 ~R 39 The alkyl group, alkoxy group, amino group, aryl group, and heteroaryl group represented by the formula: 15 ~R 17 , R4 to R 14 , R 18 ~R 30 The substituents which may be further substituted by the alkyl group, the alkoxy group, the amino group, the allyl group, the aryl group, and the heteroaryl group are the same as those described above. 15 ~R 17Examples of the above-mentioned methods are the same as those described above.

[0040] Adjacent R 32 ~R 39 may be bonded to each other to form a ring. 14 , R 18 ~R 30 This is as explained above.

[0041] <Synthesis method> Next, a method for synthesizing the organometallic complex according to this embodiment will be described. The organometallic complex according to this embodiment can be synthesized, for example, according to the reaction scheme 1 or 2 shown below.

[0042] [ka]

[0043] [ka]

[0044] In the synthesis schemes 1 and 2, the organometallic complex according to this embodiment is synthesized as (c) or (d) via the states shown in (a) and (b) below. (a) Ligand derivative (F3) (b) Dichlorodimer derivative (F4) (c) Acetylacetone derivative ligand complex (F5) (d) ppy derivative ligand complex (F7) In addition, in the synthesis schemes 1 and 2, various example compounds can be synthesized by changing F1, F2, F5, and F6, respectively.

[0045] The method for synthesizing the organometallic complex according to this embodiment is not limited to the above synthesis scheme, and may be any known method using various synthesis reagents.

[0046] <Characteristics> In inventing the organometallic complex represented by the general formula [1], the present inventors focused on the type and position of the substituents of the ligands of the organometallic complex.

[0047] The organometallic complex according to this embodiment has a bulky substituent at the ortho position of the bonding position of the benzene ring of the main ligand L with Ir (hereinafter, sometimes simply referred to as the "ortho position of the benzene ring of the main ligand L"), and is therefore a stable compound that emits red light with high efficiency and high color purity.

[0048] The properties of the organometallic complex according to the present embodiment will be described below with reference to comparative compounds having a structure similar to that of the organometallic complex according to the present embodiment. Specifically, the properties of the exemplary compound CC1 of the present invention will be described with reference to the comparative compounds 1-a and 2-a shown below.

[0049] [ka]

[0050] Here, the comparative compound 1-a is a compound that does not have a substituent at the ortho position of the benzene ring of the main ligand L. The comparative compound 2-a is a compound that has a methyl group at the ortho position of the benzene ring of the main ligand L, that is, R 15 ~R 17 In contrast, the exemplary compound CC1 has an isopropyl group at the ortho position of the benzene ring of the main ligand L, that is, R 15 ~R 17 is a compound in which one of the groups is a hydrogen atom and the other two are methyl groups.

[0051] (1) The vibration of the main ligand L is suppressed, and the half-width of the emission spectrum is narrow. The present inventors have found that the vibration of the main ligand L is suppressed by having a bulky substituent at the ortho position of the benzene ring of the main ligand L, thereby narrowing the half-width of the emission spectrum.

[0052] Even if the maximum peak wavelength of the emission spectrum is the same, the half width is narrowed, thereby improving color purity. In this embodiment, the half width with high color purity means that the half width of the emission spectrum in a dilute solution is less than 40 nm.

[0053] The skeleton of benzoisoquinoline, naphthoisoquinoline, etc., which constitutes the main ligand L, exhibits good red emission by itself. However, it is difficult to satisfy the color purity of red emission in BT-2020 by itself. Therefore, in addition to this basic characteristic, an attempt was made to obtain red emission with high color purity by narrowing the half-width of the emission spectrum. Preferably, in the CIE coordinate, the X coordinate is 0.68 or more and the Y coordinate is 0.33 or less. By using these materials with high color purity, a light-emitting element that satisfies the color purity of red emission in BT-2020 can be obtained.

[0054] Here, the inventors compared the half-width of the emission spectrum of the comparative compound 1-a, the comparative compound 2-a, and the exemplary compound CC1. The results are shown in FIG. 1. The emission wavelength was measured by photoluminescence (PL) measurement of a diluted toluene solution at room temperature and an excitation wavelength of 350 nm using a Hitachi F-4500. In addition, in order to explain this phenomenon, the figure of the optimized structure calculation result by MM2 of Chem3D is also shown.

[0055] As shown in FIG. 1, the half-width of the comparative compound 1-a is as wide as 65 nm, and the color purity is low. The half-width of the comparative compound 2-a, which has a methyl group at the ortho position of the benzene ring of the main ligand L, is 41 nm, and the color purity is improved, but the desired color purity is not achieved. On the other hand, the exemplary compound CC1, which has a bulky isopropyl group at the ortho position of the benzene ring of the main ligand L, has a half-width of 34 nm, which is a desired high color purity region characteristic, and therefore exhibits a long-wavelength red emission color suitable for the red color of the display standard such as BT-2020.

[0056] The present inventors have found that by introducing a bulky substituent into the ortho position of the benzene ring of the main ligand L in the comparative compound 1-a, the half-width of the emission spectrum becomes narrower.

[0057] As shown in the optimized structure diagram in Figure 1, the comparative compound 1-a does not have a substituent at the ortho position of the benzene ring of the main ligand L, so the main ligand plane including the naphthoisoquinoline skeleton can vibrate freely. Therefore, many vibrational levels are generated, and the emission spectrum becomes broad.

[0058] In the comparative compound 2-a, a methyl group is introduced at the ortho position of the benzene ring of the main ligand L, and the vibration of the main ligand plane including the naphthoisoquinoline skeleton is slightly restricted due to the effect of steric hindrance. Therefore, the vibration level is decreased and the emission spectrum is narrowed, but the desired color purity is still not achieved.

[0059] In the example compound CC1, an isopropyl group is introduced at the ortho position of the benzene ring of the main ligand L, and the effect of the steric hindrance is enormous, and the vibration of the main ligand plane including the naphthoisoquinoline skeleton is considerably restricted. Therefore, it was found that the vibration level is significantly reduced and the desired narrow emission spectrum can be obtained.

[0060] The organometallic complex of this embodiment is represented by the formula [2-1] or [2-2], where R1 to R3 or R 15 ~R 17 When two of R1 to R3 are hydrogen atoms or deuterium atoms, R 15 ~R 17 The other of R1 to R3 or R 15 ~R 17 At least two of the groups are preferably not hydrogen atoms or deuterium atoms. These points will be described below with reference to FIG.

[0061] FIG. 2 shows the optimized structures and half-widths of the emission spectra for comparative compound 3-a having an ethyl group at the ortho position of the benzene ring of main ligand L, exemplary compound C1 having an isobutyl group, and exemplary compound CC1 having an isopropyl group.

[0062] Here, the comparative compound 3-a has an ethyl group at the ortho position of the benzene ring of the main ligand L, i.e., R 15 ~R 17 In contrast, the exemplary compound C1 has an isobutyl group at the ortho position of the benzene ring of the main ligand L, i.e., R 15 ~R 17 In addition, as described above, the exemplary compound CC1 has an isopropyl group at the ortho position of the benzene ring of the main ligand L, that is, R 15 ~R 17 is a compound in which one of the groups is a hydrogen atom and the other two are methyl groups.

[0063] As shown in Figure 2, R in formula [2-2] 15 ~R 17 In the comparative compound 3-a, in which two of the substituents are hydrogen atoms and the remaining one is a methyl group, the vibration of the main ligand L plane cannot be sufficiently suppressed, and the emission spectrum is not sufficiently narrowed.

[0064] On the other hand, R in Equation [2-2] 15 ~R 17 In the example compound C1, two of which are hydrogen atoms and the other is an isopropyl group, the ortho-position substituent of the benzene ring of the main ligand L is bulkier than that of the comparative compound 3-a. Therefore, the example compound C1 can suppress the vibration of the plane of the main ligand L, and the emission spectrum is narrowed.

[0065] Furthermore, R in formula [2-2] 15 ~R 17In example compound CC1, one of which is a hydrogen atom and the other two are methyl groups, the periphery of the carbon atom directly bonded to the ortho position of the benzene ring of the main ligand L is bulkier than in example compound C1. Therefore, example compound CC1 can further suppress the vibration of the plane of the main ligand L, and the emission spectrum is further narrowed.

[0066] As described above, the organometallic complex according to this embodiment can emit red light with high color purity.

[0067] (2) The central metal atom, iridium, is protected, and the increased intermolecular distance suppresses TTA, improving device efficiency and durability. The inventors have found that by having a bulky substituent at the ortho position of the benzene ring of the main ligand L, the Ir atom, which is the central metal atom, is protected and the TTA is suppressed by increasing the intermolecular distance, thereby improving the device efficiency and durability.

[0068] FIG. 3 shows the ratio of EQE (external quantum efficiency) of the red light-emitting device described in the Examples below and the ratio of the luminance degradation rate due to continuous driving for Comparative Compound 1-a, Comparative Compound 2-a, and Exemplary Compound CC1.

[0069] The present inventors have found the following: That is, a bulky substituent is present in the ortho position of the benzene ring of the main ligand L, so that a substituent unit is present in the vicinity of the Ir atom. This protects the Ir atom, expands the intermolecular distance during thin film formation, suppresses TTA (triplet exciton-triplet exciton annihilation), and improves the EQE and durability of the organic light-emitting device.

[0070] In the organic light-emitting device, the organometallic complex of the present embodiment can be suitably used as a light-emitting material, and is usually used by doping it into a host material at a concentration of about several percent. In this case, it is preferable that the organometallic complex, which is the light-emitting material, is uniformly dispersed in the thin film constituting the light-emitting layer, and that the distance between the organometallic complexes is large. This will be explained.

[0071] In an organic light-emitting device, it is preferable that excitons obtained by recombination of holes and electrons in the light-emitting layer are efficiently emitted from the light-emitting material. Here, when recombination occurs, singlet and triplet excitons are generated in a ratio of 1:3. Since triplet excitons have a long excitation life, it is preferable to efficiently emit light before they are used in processes other than light emission. One of the processes other than light emission is TTA. This causes the generation of singlet excitons due to collision between triplet excitons and triplet excitons, and deactivation from transition to a higher excited state. In addition, this TTA is significantly affected by the distance between molecules, and the probability increases exponentially as the distance becomes closer.

[0072] In the light-emitting layer, the organometallic complex, which is the light-emitting material, has the lowest excitation energy, so triplet excitons tend to exist on the organometallic complex. In other words, the closer the organometallic complexes are to each other, the more likely they are to experience energy loss and degradation due to TTA. In other words, this leads to a decrease in efficiency and a deterioration in durability.

[0073] The present inventors attempted to introduce bulky substituents in order to increase the distance between Ir complexes, particularly between Ir atoms, in the light-emitting layer film.

[0074] As shown in Figure 3, the comparative compound 1-a does not have a substituent at the ortho position of the benzene ring of the main ligand L, so there is a space near the Ir atom, which makes it easier for the distance between molecules to become short in a thin film.

[0075] In the comparative compound 2-a, a methyl group is introduced at the ortho position of the benzene ring of the main ligand L, and the vicinity of the Ir atom is slightly protected by the effect of steric hindrance, so the distance between the molecules is larger than that of the comparative compound 1-a.

[0076] On the other hand, in the example compound CC1, an isopropyl group is introduced at the ortho position of the benzene ring of the main ligand L, and the effect of steric hindrance is enormous, and the vicinity of the Ir atom is protected by a substituent unit. As a result, the distance between molecules in the thin film is large, reducing the TTA and achieving high efficiency and durability.

[0077] As described above, the organometallic complex of this embodiment has a bulky substituent at the ortho position of the benzene ring of the main ligand L, which increases the intermolecular distance. As a result, when used as a light-emitting material for an organic light-emitting device, TTA can be suppressed and excellent device efficiency and driving durability can be achieved.

[0078] (3) Sublimation properties are improved. The organometallic complex of this embodiment is a compound having a bulky substituent at the ortho position of the benzene ring of the main ligand L. This reduces intermolecular interactions. If the intermolecular interactions are reduced, the sublimability increases.

[0079] The improvement of sublimability enables the high purification of materials by sublimation purification and the preparation of organic light-emitting devices by vapor deposition. This makes it possible to reduce impurities contained in the organic light-emitting device, and to reduce the deterioration of the luminous efficiency and the driving durability caused by impurities. In addition, the reduction of concentration quenching is preferable from the viewpoint of improving the luminous efficiency of the organic light-emitting device.

[0080] (4) Other characteristics In the organometallic complex according to the present embodiment, concentration quenching can be reduced by providing a halogen atom, a deuterium atom, an alkyl group, an allyl group, an aryl group, or a silyl group in the basic skeleton. Furthermore, by these substitutions, a compound can be obtained that has improved sublimability during sublimation and improved solvent solubility when used for coating.

[0081] In the organometallic complex according to the present embodiment, the basic skeleton may be provided with a heteroatom-containing substituent, i.e., a halogen atom, an alkoxy group, an amino group, a heteroaryl group, an aryloxy group, a heteroaryloxy group, or a cyano group, which can provide more electron donating and electron withdrawing effects to the ligand and the Ir atom. These substituents can more easily provide a compound with an adjusted emission wavelength.

[0082] <Example> Specific examples of the organometallic complex according to the present invention are shown below, but the present invention is not limited to these.

[0083]

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[0096] Compounds in group A have the partial structure Ir(L) m is represented by formula [2-1], two of R1 to R3 are hydrogen atoms or deuterium atoms, the remaining is a secondary or higher alkyl group, and L' is represented by formula [3]. The compounds in group A are compounds with higher solubility and sublimability among the organometallic complexes according to the present invention.

[0097] Compounds in the AA group have the partial structure Ir(L) m is represented by formula [2-1], two of R1 to R3 are not hydrogen atoms or deuterium atoms, and L' is represented by formula [3]. The compounds in the AA group are compounds that have a narrower half-width and higher sublimability among the organometallic complexes according to the present invention.

[0098] Compounds in group B have the substructure Ir(L) m is represented by formula [2-1], two of R1 to R3 are hydrogen atoms or deuterium atoms, the remaining is a secondary or higher alkyl group, and L' is represented by formula [4]. Compounds in group B are highly stable compounds among the organometallic complexes according to the present invention.

[0099] Compounds in the BB group have the substructure Ir(L) m is represented by the formula [2-1], two of R1 to R3 are not hydrogen atoms or deuterium atoms, and L' is represented by the formula [4]. The BB group compounds are highly stable compounds among the organometallic complexes according to the present invention.

[0100] Compounds in group C have the substructure Ir(L) m is shown in formula [2-2], and R 15 ~R 17 In the organometallic complexes, two of the groups are hydrogen atoms or deuterium atoms, and the other is a secondary or higher alkyl group, and L' is represented by the formula [3]. The compounds in group C are compounds that have longer wavelength emission and are highly soluble among the organometallic complexes according to the present invention.

[0101] Compounds in the CC group have the substructure Ir(L) m is shown in formula [2-2], and R 15 ~R 17 In the organometallic complexes according to the present invention, two of the L' are not hydrogen atoms or deuterium atoms, and L' is represented by the formula [3]. The compounds in the CC group are compounds that have longer wavelength emission, narrow half-widths, and high color purity, among the organometallic complexes according to the present invention.

[0102] Compounds in group D have the substructure Ir(L) m is shown in formula [2-2], and R 15 ~R 17 Two of the groups are hydrogen atoms or deuterium atoms, and the other is a secondary or higher alkyl group, and L' is an organometallic complex represented by formula [4]. The compounds in group D are, among the organometallic complexes according to the present invention, compounds that have longer wavelength emission and are highly stable.

[0103] Compounds in the DD group have the substructure Ir(L) m is shown in formula [2-2], and R 15 ~R 17 In the organometallic complexes of the present invention, two of the L' are not hydrogen atoms or deuterium atoms, and L' is represented by the formula [4]. The compounds in the DD group are highly stable compounds that have longer wavelength emission among the organometallic complexes of the present invention.

[0104] Compounds in group E have the substructure Ir(L) m is shown in formula [2-2], and R 25 and R 26 forms a benzene ring, and R 15 ~R 17The compounds in group E are organometallic complexes in which two of the atoms are not hydrogen or deuterium, and L' is represented by the formula [3]. m is shown in formula [2-1], and R9 and R 10 The compounds in group E are organometallic complexes having a naphthalene ring formed by the formula (I). Among the organometallic complexes according to the present invention, the compounds in group E are compounds having high oscillator strength and high efficiency.

[0105] Among the organometallic complexes of the present invention, the AA group and the CC group are preferred because they are compound groups with narrower half-widths.Furthermore, among the organometallic complexes of the present invention, the CC group is a compound having a narrower half-width, long wavelength emission, and red emission with higher color purity.

[0106] The organometallic complex according to the present invention is a compound that exhibits light emission suitable for red light emission. Therefore, by using the organometallic complex according to the present invention as a constituent material of an organic light-emitting device, it is possible to obtain an organic light-emitting device having good light-emitting properties and excellent durability.

[0107] <Organic light-emitting element> The organic light-emitting device of this embodiment has at least a first electrode, a second electrode, and an organic compound layer disposed between these electrodes. One of the first electrode and the second electrode is an anode, and the other is a cathode. In the organic light-emitting device of this embodiment, the organic compound layer may be a single layer or a laminate consisting of multiple layers as long as it has a light-emitting layer. Here, when the organic compound layer is a laminate consisting of multiple layers, the organic compound layer may have a hole injection layer, a hole transport layer, an electron blocking layer, a hole exciton blocking layer, an electron transport layer, an electron injection layer, etc. in addition to the light-emitting layer. The light-emitting layer may be a single layer or a laminate consisting of multiple layers.

[0108] In the organic light-emitting device of the present embodiment, at least one layer of the organic compound layer contains the organometallic complex according to the present embodiment. Specifically, the organometallic complex according to the present embodiment is contained in any one of the above-mentioned light-emitting layer, hole injection layer, hole transport layer, electron blocking layer, hole-exciton blocking layer, electron transport layer, electron injection layer, etc. The organometallic complex according to the present embodiment is preferably contained in the light-emitting layer.

[0109] In the organic light-emitting device of this embodiment, when the organometallic complex according to this embodiment is contained in the light-emitting layer, the light-emitting layer may be a layer consisting of only the organometallic complex according to this embodiment, or may be a layer consisting of the organometallic complex according to this embodiment and other compounds. Here, when the light-emitting layer is a layer consisting of the organometallic complex according to this embodiment and other compounds, the organometallic complex according to this embodiment may be used as a host of the light-emitting layer or as a guest. It may also be used as an assist material that can be contained in the light-emitting layer. Here, the host is a compound having the largest mass ratio among the compounds constituting the light-emitting layer. The guest is a compound having a smaller mass ratio than the host among the compounds constituting the light-emitting layer, and is a compound that is responsible for the main emission. The assist material is a compound having a smaller mass ratio than the host among the compounds constituting the light-emitting layer, and assists the emission of the guest. The assist material is also called a second host.

[0110] When the organic compound according to this embodiment is used as a guest in the light-emitting layer, the concentration of the guest is preferably from 0.01% by mass to 20% by mass, and more preferably from 0.1% by mass to 10% by mass, based on the entire light-emitting layer.

[0111] The present inventors have conducted various studies and found that when the organometallic complex according to this embodiment is used as a host or guest of the light-emitting layer, particularly as a guest of the light-emitting layer, an element that exhibits high efficiency and high luminance light output and is extremely durable can be obtained. The light-emitting layer may be a single layer or multiple layers, and it is also possible to mix the light emitted by the light-emitting layer with the red light emitted by the present embodiment by including a light-emitting material having another light-emitting color. Multiple layers means a state in which the light-emitting layer and another light-emitting layer are laminated. In this case, the light-emitting color of the organic light-emitting element is not limited to red. 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 red, that is, blue or green. Furthermore, a third light-emitting layer that emits blue light and a charge-generating layer may be provided between the light-emitting layer or the laminated light-emitting layer in this embodiment and the first or second electrode. The charge-generating layer exhibits the function of a tandem element, and the electrons generated from the charge-generating layer and the holes injected from the first electrode are charge-recombined to generate excitons, and the holes generated from the charge-generating layer and the electrons injected from the second electrode are charge-recombined to form excitons. For this reason, the internal quantum efficiency is doubled. For example, a white light emitting element can be provided by forming a tandem element having a yellow light emitting layer in which a red light emitting layer and a green light emitting layer made of the light emitting layer of this embodiment are laminated, and a blue light emitting layer.

[0112] The method for forming the organic compound layer is not particularly limited, and the organic compound layer can be formed by, for example, deposition, coating, etc. Details of this will be described in detail in the examples below.

[0113] The organometallic complex according to this embodiment can be used as a constituent material of an organic compound layer other than the light-emitting layer constituting the organic light-emitting device of this embodiment. Specifically, it may be used as a constituent material of an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, a hole blocking layer, etc. In this case, the emission color of the organic light-emitting device is not limited to red. More specifically, it may be white light or an intermediate color.

[0114] <Other compounds> Here, in addition to the organometallic complex according to the present embodiment, conventionally known low molecular weight and high molecular weight hole injecting or hole transporting compounds, host compounds, light emitting compounds, electron injecting or electron transporting compounds, etc. may be used together as necessary. Examples of these compounds are given below.

[0115] As the hole injection transport material, a material having high hole mobility is preferable so that the injection of holes from the anode can be easily performed and the injected holes can be transported to the light emitting layer. In addition, a material having a high glass transition temperature is preferable so as to suppress deterioration of the film quality such as crystallization in the organic light emitting device. Examples of low molecular weight and high molecular weight materials having hole injection transport performance include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. Furthermore, the above hole injection transport material is also preferably used in the electron blocking layer. Specific examples of compounds used as the hole injection transport material are shown below, but of course, the present invention is not limited to these.

[0116] [ka]

[0117] Examples of luminescent materials mainly involved in the luminescence function include, in addition to the organometallic complex of this embodiment, condensed ring compounds (e.g., fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, organoaluminum complexes such as tris(8-quinolinolato)aluminum, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, and polymer derivatives such as poly(phenylenevinylene) derivatives, poly(fluorene) derivatives, and poly(phenylene) derivatives. Specific examples of compounds used as luminescent materials are shown below, but are of course not limited to these.

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[0120] Examples of the host or emission assist material contained in the emission layer include aromatic hydrocarbon compounds or derivatives thereof, as well as carbazole derivatives, azine derivatives, xanthone derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organic aluminum complexes such as tris(8-quinolinolato)aluminum, organic beryllium complexes, etc. Specific examples of compounds used as the host or emission assist material are shown below, but are of course not limited to these.

[0121] [ka]

[0122] The electron transporting material can be arbitrarily selected from those capable of transporting electrons injected from the cathode to the light-emitting layer, and is selected in consideration of the balance with the hole mobility of the hole transporting material. Examples of materials having electron transporting properties include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organic aluminum complexes, and condensed ring compounds (e.g., fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the above electron transporting materials are also preferably used in the hole blocking layer. Specific examples of compounds used as electron transporting materials are shown below, but are of course not limited to these.

[0123] [ka]

[0124] The electron injection material can be selected from those that can easily inject electrons from the cathode, and is selected in consideration of the balance with hole injection properties. Organic compounds include n-type dopants and reducing dopants. For example, compounds containing alkali metals such as lithium fluoride, lithium complexes such as lithium quinolinol, benzimidazolidene derivatives, imidazolidene derivatives, fulvalene derivatives, and acridine derivatives can be used in combination with the above electron transport materials.

[0125] <Configuration of organic light-emitting element> The organic light-emitting element is provided by forming an insulating layer, a first electrode, an organic compound layer, and a second electrode on a substrate. A protective layer, a color filter, a microlens, etc. may be provided on the second electrode. When a color filter is provided, a planarizing layer may be provided between the protective layer. The planarizing layer may be made of acrylic resin, etc. The same applies when a planarizing layer is provided between the color filter and the microlens.

[0126] [substrate] Examples of the substrate include quartz, glass, silicon wafer, resin, and metal. In addition, a switching element such as a transistor and wiring may be provided on the substrate, and an insulating layer may be provided thereon. As the insulating layer, any material can be used as long as it can form a contact hole so that wiring can be formed between the first electrode and the insulating layer, and insulation from wiring that is not connected can be ensured. For example, resin such as polyimide, silicon oxide, silicon nitride, etc. can be used.

[0127] [electrode] A pair of electrodes can be used. The pair of electrodes may be an anode and a cathode. When an electric field is applied in the direction in which the organic light-emitting element emits light, the electrode with a higher potential is the anode, and the other is the cathode. It can also be said that the electrode that supplies holes to the light-emitting layer is the anode, and the electrode that supplies electrons is the cathode.

[0128] The material constituting the anode should have as large a work function as possible. For example, metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, tungsten, etc., mixtures containing these metals, alloys combining these metals, metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide can be used. Conductive polymers such as polyaniline, polypyrrole, and polythiophene can also be used.

[0129] These electrode materials may be used alone or in combination of two or more kinds. The anode may be composed of one layer or multiple layers.

[0130] When used as a reflective electrode, for example, chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys or laminates thereof can be used. The above materials can also function as a reflective film without serving as an electrode. When used as a transparent electrode, a transparent conductive layer of oxide such as indium tin oxide (ITO) or indium zinc oxide can be used, but is not limited to these. Photolithography technology can be used to form the electrode.

[0131] On the other hand, the material for the cathode should have a small work function. Examples of the material include alkali metals such as lithium, alkaline earth metals such as calcium, aluminum, titanium, manganese, silver, lead, chromium, and other metals or mixtures containing these metals. Alternatively, alloys combining these metals can be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper, zinc-silver, and the like can be used. Metal oxides such as indium tin oxide (ITO) can also be used. These electrode materials may be used alone or in combination of two or more types. The cathode may have a single layer structure or a multi-layer structure. Among these, it is preferable to use silver, and it is even more preferable to use a silver alloy to reduce the aggregation of silver. As long as the aggregation of silver can be reduced, the ratio of the alloy is not important. For example, the ratio of silver to other metals may be 1:1, 3:1, and the like.

[0132] The cathode may be a top-emission element using an oxide conductive layer such as ITO, or a bottom-emission element using a reflective electrode such as aluminum (Al), and is not particularly limited. The method for forming the cathode is not particularly limited, but it is more preferable to use a direct current or alternating current sputtering method, etc., since the film coverage is good and the resistance can be easily reduced.

[0133] [Organic compound layer] The organic compound layer may be formed as a single layer or as multiple layers. When the organic compound layer has multiple layers, it may be called a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, or an electron injection layer depending on its function. The organic compound layer is mainly composed of an organic compound, but may contain inorganic atoms or inorganic compounds. For example, it may contain copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, or the like. The organic compound layer may be disposed between the first electrode and the second electrode, or may be disposed in contact with the first electrode and the second electrode.

[0134] The organic compound layers (hole injection layer, hole transport layer, electron blocking layer, light emitting layer, hole blocking layer, electron transport layer, electron injection layer, etc.) constituting the organic light emitting device according to one embodiment of the present invention are formed by the method shown below.

[0135] The organic compound layer constituting the organic light-emitting device according to one embodiment of the present invention can be formed by dry processes such as vacuum deposition, ionization deposition, sputtering, plasma, etc. Alternatively, instead of the dry process, a wet process can be used in which a layer is formed by dissolving the compound in an appropriate solvent and applying a known coating method (e.g., spin coating, dipping, casting, LB method, inkjet method, etc.).

[0136] Here, when the layer is formed by a vacuum deposition method or a solution coating method, crystallization is unlikely to occur and the layer has excellent stability over time. When the layer is formed by a coating method, the layer can be formed by combining with a suitable binder resin.

[0137] Examples of the binder resin include, but are not limited to, polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, and urea resin.

[0138] These binder resins may be used alone as homopolymers or copolymers, or in combination of two or more kinds. If necessary, known additives such as plasticizers, antioxidants, and ultraviolet absorbers may be used in combination.

[0139] [Protective layer] A protective layer may be provided on the second electrode. For example, by bonding glass provided with a moisture absorbent on the second electrode, it is possible to reduce the intrusion of water and the like into the organic compound layer and reduce the occurrence of display defects. In another embodiment, a passivation film such as silicon nitride may be provided on the second electrode to reduce the intrusion of water and the like into the organic compound layer. For example, after the second electrode is formed, it may be transported to another chamber without breaking the vacuum, and a silicon nitride film having a thickness of 2 μm may be formed by the CVD method to serve as a protective layer. A protective layer may be provided using an atomic deposition method (ALD method) after the film is formed by the CVD method. The material of the film formed by the ALD method is not limited, and may be silicon nitride, silicon oxide, aluminum oxide, etc. Silicon nitride may be further formed by the CVD method on the film formed by the ALD method. The film formed by the ALD method may have a smaller thickness than the film formed by the CVD method. Specifically, it may be 50% or less, or even 10% or less.

[0140] [Color Filter] A color filter may be provided on the protective layer. For example, a color filter taking into consideration the size of the organic light-emitting element may be provided on another substrate and then bonded to the substrate on which the organic light-emitting element is provided, or a color filter may be patterned on the protective layer described above using a photolithography technique. The color filter may be made of a polymer.

[0141] [Planarization layer] A planarization layer may be provided between the color filter and the protective layer. The planarization layer is provided for the purpose of reducing unevenness of the layer below. It may also be called a material resin layer without limiting the purpose. The planarization layer may be composed of an organic compound, and may be either a low molecular weight or a high molecular weight, but is preferably a high molecular weight.

[0142] The planarization layer may be provided above and below the color filter, and may be made of the same or different materials.Specific examples of the materials include polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, and urea resin.

[0143] [Microlens] The organic light-emitting element or the organic light-emitting device may have an optical member 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 intended to increase the amount of light extracted from the organic light-emitting element or the organic light-emitting device and to control the direction of the extracted light. The microlens may have a hemispherical shape. When the microlens has a hemispherical shape, among the tangents to the hemisphere, there is a tangent that is parallel to the insulating layer, and the tangent and the hemisphere are the vertices of the microlens. The vertex of the microlens can be determined in the same manner in any cross-sectional view. That is, among the tangents to the semicircle of the microlens in the cross-sectional view, there is a tangent that is parallel to the insulating layer, and the tangent and the semicircle are the vertices of the microlens.

[0144] It is also possible to define the midpoint of the microlens. In the cross section of the microlens, a line segment is imaginary from a point where an arc shape ends to a point where another arc shape ends, and the midpoint of the line segment can be called the midpoint of the microlens. The cross section for determining the vertex and midpoint may be a cross section perpendicular to the insulating layer.

[0145] [Opposite substrate] A counter substrate may be provided on the planarization layer. The counter substrate is called a counter substrate because it is provided at a position corresponding to the aforementioned substrate. The constituent material of the counter substrate may be the same as that of the aforementioned substrate. When the aforementioned substrate is a first substrate, the counter substrate may be a second substrate.

[0146] [Pixel circuit] An organic light-emitting device having an organic light-emitting element may have a pixel circuit connected to the organic light-emitting element. The pixel circuit may be an active matrix type that controls the emission of the first light-emitting element and the second light-emitting element independently. The active matrix type circuit may be a voltage programming circuit or a current programming circuit. The drive circuit has a pixel circuit for each pixel. The pixel circuit may have a light-emitting element, a transistor that controls the emission luminance of the light-emitting element, a transistor that controls the emission timing, a capacitance that holds the gate voltage of the transistor that controls the emission luminance, and a transistor for connecting to GND without going through the light-emitting element.

[0147] The light emitting device has a display region and a peripheral region arranged around the display region. The display region has a pixel circuit, and the peripheral region has a display control circuit. The mobility of a transistor constituting the pixel circuit may be smaller than the mobility of a transistor constituting the display control circuit. The slope of the current-voltage characteristic of the transistor constituting the pixel circuit may be smaller than the slope of the current-voltage characteristic of the transistor constituting the display control circuit. The slope of the current-voltage characteristic can be measured by the so-called Vg-Ig characteristic. The transistor constituting the pixel circuit is a transistor connected to a light emitting element, such as a first light emitting element.

[0148] [Pixels] An organic light emitting device having an organic light emitting element may have a plurality of pixels, each of which has sub-pixels that emit different colors, for example, each of which may have one of the RGB emission colors.

[0149] The pixel emits light in an area also called the pixel aperture. This area is the same as the first area. The pixel aperture may be 15 μm or less, or 5 μm or more. More specifically, it may be 11 μm, 9.5 μm, 7.4 μm, 6.4 μm, etc. The distance between the subpixels may be 10 μm or less, more specifically, it may be 8 μm, 7.4 μm, 6.4 μm.

[0150] The pixels may have a known arrangement in plan view. For example, they may be a stripe arrangement, a delta arrangement, a pentile arrangement, or a Bayer arrangement. The shape of the subpixels in plan view may be any known shape. For example, they may be a rectangle, a quadrangle such as a diamond, or a hexagon. Of course, if the shape is not an exact figure but is close to a rectangle, it is included in the rectangle. The shape of the subpixels and the pixel arrangement may be used in combination.

[0151] <Applications of organic light-emitting devices> The organic light-emitting device according to the present embodiment can be used as a component of a display device or a lighting device, and can also be used as an exposure light source for an electrophotographic image forming device, a backlight for a liquid crystal display device, a light-emitting device having a white light source and a color filter, etc.

[0152] The display device may be an image information processing device having an image input unit for inputting image information from an area CCD, a linear CCD, a memory card, or the like, an information processing unit for processing the input information, and displaying the input image on a display unit. The display device may have a plurality of pixels, at least one of which may have the organic light-emitting element of this embodiment and an active element such as a transistor connected to the organic light-emitting element. In this case, the substrate may be a semiconductor substrate such as silicon, and the transistor may be a MOSFET formed on the substrate. The image display device has an input unit for inputting image information and a display unit for outputting an image, and the display unit has the display device of this embodiment.

[0153] The display unit of the imaging device or inkjet printer may have a touch panel function. The driving method of the touch panel function may be an infrared type, a capacitance type, a resistive film type, or an electromagnetic induction type, and is not particularly limited. The display device may be used in the display unit of a multifunction printer.

[0154] Next, the display device according to the present embodiment will be described with reference to the drawings. Fig. 4 is a schematic cross-sectional view showing an example of a display device having an organic light-emitting element and a transistor connected to the organic light-emitting element. The transistor is an example of an active element. The transistor may be a thin film transistor (TFT).

[0155] FIG. 4(a) shows an example of a pixel, which is a component of the display device according to this embodiment. The pixel has sub-pixels 10. The sub-pixels are divided into 10R, 10G, and 10B according to their light emission. The emitted light color may be distinguished by the wavelength emitted from the light-emitting layer, or the light emitted from the sub-pixels may be selectively transmitted or color-converted by a color filter or the like. Each sub-pixel 10 has a reflective electrode, which is a first electrode 2, on an interlayer insulating layer 1, an insulating layer 3 covering the edge of the first electrode 2, an organic compound layer 4 covering the first electrode 2 and the insulating layer 3, a transparent electrode, which is a second electrode 5, a protective layer 6, and a color filter 7.

[0156] A transistor and a capacitor may be disposed below or inside the interlayer insulating layer 1. The transistor and the first electrode 2 may be electrically connected via a contact hole or the like (not shown).

[0157] The insulating layer 3 is also called a bank or a pixel separation film. It covers the ends of the first electrodes 2 and is disposed so as to surround the first electrodes 2. The portions where the insulating layer 3 is not disposed are in contact with the organic compound layer 4 and become light-emitting regions.

[0158] The organic compound layer 4 has a hole injection layer 41 , a hole transport layer 42 , a first light emitting layer 43 , a second light emitting layer 44 , and an electron transport layer 45 .

[0159] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0160] The protective layer 6 reduces the penetration of moisture into the organic compound layer 4. The protective layer 6 is illustrated as being a single layer, but may be a multi-layer. Each layer may be an inorganic compound layer and an organic compound layer.

[0161] The color filters 7 are divided into 7R, 7G, and 7B according to their colors. The color filters 7 may be formed on a planarization film (not shown). Also, a resin protective layer (not shown) may be provided on the color filters 7. Also, the color filters 7 may be formed on the protective layer 6. Alternatively, the color filters 7 may be provided on an opposing substrate such as a glass substrate and then bonded thereto.

[0162] The display device 100 in Fig. 4(b) has an organic light-emitting element 26 and a TFT 18, which is an example of a transistor. A substrate 11 made of glass, silicon, or the like, and an insulating layer 12 are provided thereon. An active element such as the TFT 18 is disposed on the insulating layer 12, and a gate electrode 13 of the active element, a gate insulating film 14, and a semiconductor layer 15 are provided. The TFT 18 has a drain electrode 16 and a source electrode 17. An insulating film 19 is provided on the top of the TFT 18. An anode 21 constituting the organic light-emitting element 26 and the source electrode 17 are connected via a contact hole 20 provided in the insulating film 19.

[0163] The electrical connection between the electrodes (anode 21, cathode 23) included in the organic light-emitting element 26 and the electrodes (source electrode 17, drain electrode 16) included in the TFT 18 is not limited to the embodiment shown in Fig. 4(b). In other words, it is sufficient that either the anode 21 or the cathode 23 is electrically connected to either the source electrode 17 or the drain electrode 16 of the TFT 18.

[0164] 4(b), the organic compound layer 22 is illustrated as a single layer, but the organic compound layer 22 may be a multi-layer. A first protective layer 24 and a second protective layer 25 are provided on the cathode 23 to reduce deterioration of the organic light-emitting element 26.

[0165] In the display device 100 of FIG. 4(b), transistors are used as switching elements, but other switching elements such as MIM elements may be used instead.

[0166] The transistor used in the display device 100 of Fig. 4(b) is not limited to a thin film transistor having an active layer on an insulating surface of a substrate, but may be a transistor using a single crystal silicon wafer. Examples of the active layer include single crystal silicon, amorphous silicon, non-single crystal silicon such as microcrystalline silicon, and non-single crystal oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Thin film transistors are also called TFT elements.

[0167] The transistors included in the display device 100 of Fig. 4(b) may be formed in a substrate such as a Si substrate. Here, "formed in a substrate" means that the substrate itself such as a Si substrate is processed to produce the transistors. In other words, having a transistor in a substrate can be seen as the substrate and the transistor being integrally formed.

[0168] The organic light-emitting element according to this embodiment has its light emission brightness controlled by a TFT, which is an example of a switching element, and by providing the organic light-emitting element on a plurality of surfaces, an image can be displayed based on the respective light emission brightnesses. The switching element according to this embodiment is not limited to a TFT, and may be a transistor formed of low-temperature polysilicon, or an active matrix driver formed on a substrate such as a Si substrate. On the substrate may also be within the substrate. Whether to provide a transistor within the substrate or to use a TFT is selected according to the size of the display unit. For example, if the size is about 0.5 inches, it is preferable to provide the organic light-emitting element on a Si substrate.

[0169] 5 is a schematic diagram showing an example of a display device according to the present embodiment. The display device 1000 may have a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008 between an upper cover 1001 and a lower cover 1009. Flexible printed circuits FPC1002 and 1004 are connected to the touch panel 1003 and the display panel 1005. A transistor is printed on the circuit board 1007. The battery 1008 may not be provided if the display device is not a portable device, and may be provided in a different position if the display device is a portable device.

[0170] The display device according to this embodiment may have color filters having red, green, and blue colors, the red, green, and blue colors being arranged in a delta arrangement.

[0171] The display device according to the present embodiment may be used as a display unit of a mobile terminal. In this case, the display device may have both a display function and an operation function. Examples of the mobile terminal include mobile phones such as smartphones, tablets, and head-mounted displays.

[0172] The display device according to the present embodiment may be used as a display unit of an imaging device having an optical unit with a plurality of lenses and an imaging element that receives light that has passed through the optical unit. The imaging device may have a display unit that displays information acquired by the imaging element. The display unit may be a display unit exposed to the outside of the imaging device, or may be a display unit disposed within a viewfinder. The imaging device may be a digital camera or a digital video camera.

[0173] 6(a) is a schematic diagram showing an example of an imaging device according to this embodiment. The imaging device 1100 may have a viewfinder 1101, a rear display 1102, an operation unit 1103, and a housing 1104. The viewfinder 1101 may have a display device according to this embodiment. In this case, the display device may display not only an image to be captured, but also environmental information, imaging instructions, and the like. The environmental information may include the intensity of external light, the direction of external light, the moving speed of the subject, the possibility that the subject will be blocked by an obstruction, and the like.

[0174] Since the timing suitable for imaging is short, it is better to display information as soon as possible. Therefore, it is preferable to use a display device using the organic light-emitting element of this embodiment. This is because the organic light-emitting element has a fast response speed. A display device using an organic light-emitting element can be used more preferably than a liquid crystal display device, which requires a high display speed.

[0175] The imaging device 1100 has an optical section (not shown). The optical section has a plurality of lenses, which form an image on an imaging element housed in a housing 1104. The focus of the plurality of lenses can be adjusted by adjusting their relative positions. This operation can also be performed automatically. The imaging device may be called a photoelectric conversion device. The photoelectric conversion device can include an imaging method that does not capture images sequentially, but detects the difference from the previous image, cuts out an image from an image that is always recorded, and the like.

[0176] FIG. 6(b) is a schematic diagram showing an example of an electronic device according to the present embodiment. The electronic device 1200 has a display unit 1201, an operation unit 1202, and a housing 1203. The housing 1203 may have a circuit, a printed circuit board having the circuit, a battery, and a communication unit. The operation unit 1202 may be a button or a touch panel type reaction unit. The operation unit 1202 may be a biometric recognition unit that recognizes a fingerprint and performs unlocking or the like. An electronic device having a communication unit can also be called a communication device. The electronic device 1200 may further have a camera function by including a lens and an image sensor. An image captured by the camera function is displayed on the display unit 1201. Examples of the electronic device 1200 include a smartphone and a notebook computer.

[0177] FIG. 7 is a schematic diagram showing an example of a display device according to the present embodiment. FIG. 7(a) shows a display device such as a television monitor or a PC monitor. The display device 1300 has a frame 1301 and a display unit 1302. The light-emitting element according to the present embodiment may be used in the display unit 1302. The display device 1300 has the frame 1301 and a base 1303 that supports the display unit 1302. The base 1303 is not limited to the form shown in FIG. 7(a). The lower side of the frame 1301 may also serve as the base. The frame 1301 and the display unit 1302 may be curved. The radius of curvature may be 5000 mm or more and 6000 mm or less.

[0178] FIG. 7(b) is a schematic diagram showing another example of the display device according to the present embodiment. The display device 1310 of FIG. 7(b) is configured to be bendable, and is a so-called foldable display device. The display device 1310 has a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may have a light-emitting element according to the present embodiment. The first display unit 1311 and the second display unit 1312 may be one display unit without a joint. The first display unit 1311 and the second display unit 1312 can be separated at the bending point. The first display unit 1311 and the second display unit 1312 may display different images, or the first and second display units may display one image.

[0179] FIG. 8(a) is a schematic diagram showing an example of a lighting device according to the present embodiment. The lighting device 1400 may have a housing 1401, a light source 1402, a circuit board 1403, an optical filter 1404 that transmits light emitted by the light source 1402, and a light diffusion unit 1405. The light source 1402 may have an organic light-emitting element according to the present embodiment. The optical filter 1404 may be a filter that improves the color rendering of the light source. The light diffusion unit 1405 can effectively diffuse the light of the light source, such as for lighting up, and deliver the light over a wide range. The optical filter 1404 and the light diffusion unit 1405 may be provided on the light emission side of the lighting. If necessary, a cover may be provided on the outermost part.

[0180] The lighting device is, for example, a device that illuminates a room. The lighting device may emit white, neutral white, or any other color from blue to red. It may have a dimming circuit that adjusts the light intensity and a color adjusting circuit that adjusts the emitted color. The lighting device may have the organic light-emitting element of this embodiment and a power supply circuit connected thereto. The power supply circuit is a circuit that converts AC voltage into DC voltage. Moreover, white has a color temperature of 4200K, and neutral white has a color temperature of 5000K. The lighting device may have a color filter.

[0181] The lighting device according to the present embodiment may also include a heat dissipation section that dissipates heat from within the device to the outside, and examples of the heat dissipation section include metals with high specific heat, liquid silicon, and the like.

[0182] 8(b) is a schematic diagram of an automobile, which is an example of a moving body according to this embodiment. The automobile has tail lamps, which are an example of a lamp. The automobile 1500 has tail lamps 1501, and may be configured to turn on the tail lamps when braking or the like is performed.

[0183] The tail lamp 1501 may have an organic light-emitting element according to this embodiment. The tail lamp 1501 may have a protective member for protecting the organic light-emitting element. The protective member may be made of any material as long as it has a certain degree of strength and is transparent, but is preferably made of polycarbonate or the like. Polycarbonate may be mixed with a furandicarboxylic acid derivative, an acrylonitrile derivative, or the like.

[0184] The automobile 1500 may have a body 1503 and a window 1502 attached thereto. The window 1502 may be a transparent display unless it is a window for checking the front and rear of the automobile. The transparent display may have an organic light-emitting element according to this embodiment. In this case, the constituent materials of the electrodes and the like of the organic light-emitting element are made of transparent members.

[0185] The moving body according to the present embodiment may be a ship, an aircraft, a drone, or the like. The moving body may have a body and a lamp provided on the body. The lamp may emit light to indicate the position of the body. The lamp has the organic light-emitting element according to the present embodiment.

[0186] An application example of the display device of each of the above-mentioned embodiments will be described with reference to Fig. 9. The display device can be applied to a system that can be worn as a wearable device such as smart glasses, HMD, and smart contacts. An image capturing and display device used in such an application example has an image capturing device capable of photoelectrically converting visible light, and a display device capable of emitting visible light.

[0187] Fig. 9(a) is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention. Using Fig. 9(a), glasses 1600 (smart glasses) according to one application example will be described. An imaging device 1602 such as a CMOS sensor or SPAD is provided on the front side of a lens 1601 of the glasses 1600. In addition, a display device according to each of the above-mentioned embodiments is provided on the back side of the lens 1601.

[0188] The glasses 1600 further include a control device 1603. The control device 1603 functions as a power source that supplies power to the image capture device 1602 and the display device. The control device 1603 also controls the operations of the image capture device 1602 and the display device. The lens 1601 is formed with an optical system for focusing light on the image capture device 1602.

[0189] FIG. 9(b) is a schematic diagram showing another example of a wearable device according to an embodiment of the present invention. Using FIG. 9(b), glasses 1610 (smart glasses) according to one application example will be described. The glasses 1610 have a control device 1612, and the control device 1612 is equipped with an imaging device corresponding to the imaging device 1602 in FIG. 9(a) and a display device. The lens 1611 is formed with an imaging device in the control device 1612 and an optical system for projecting light emitted from the display device, and an image is projected onto the lens 1611. The control device 1612 functions as a power source that supplies power to the imaging device and the display device, and controls the operations of the imaging device and the display device.

[0190] The control device 1612 may have a gaze detection unit that detects the gaze of the wearer. Infrared light may be used to detect the gaze. The infrared light emitting unit emits infrared light to the eyeball of the user gazing at the display image. The image capturing unit having a light receiving element detects the reflected light of the emitted infrared light from the eyeball to obtain an image of the eyeball. By providing a reduction means for reducing the light from the infrared light emitting unit to the display unit in a planar view, the deterioration of image quality is reduced. The gaze of the user to the display image is detected from the image of the eyeball obtained by capturing infrared light. Any known method can be applied to gaze detection using the image of the eyeball. As an example, a gaze detection method based on a Purkinje image due to reflection of irradiated light on the cornea can be used. More specifically, gaze detection processing based on a pupil-corneal reflex method is performed. Using the pupil-corneal reflex method, a gaze vector representing the direction (rotation angle) of the eyeball is calculated based on the image of the pupil and the Purkinje image included in the image of the eyeball, thereby detecting the gaze of the user.

[0191] A display device according to an embodiment of the present invention may have an imaging device having a light receiving element, and may control a display image of the display device based on the user's line of sight information from the imaging device. Specifically, the display device determines a first field of view area to which the user gazes and a second field of view area other than the first field of view area based on the line of sight information. The first field of view area and the second field of view area may be determined by a control device of the display device, or may be received from an external control device. In the display area of ​​the display device, the display resolution of the first field of view area may be controlled to be higher than the display resolution of the second field of view area. In other words, the resolution of the second field of view area may be lower than that of the first field of view area.

[0192] The display area includes a first display area and a second display area different from the first display area, and an area having a high priority is determined from the first display area and the second display area based on line-of-sight information. The first field of view area and the second field of view area may be determined by a control device of the display device, or may be determined by an external control device and received. The resolution of the area having a high priority may be controlled to be higher than the resolution of areas other than the area having a high priority. In other words, the resolution of an area having a relatively low priority may be lowered.

[0193] AI may be used to determine the first field of view area and the area with high priority. The AI ​​may be a model configured to estimate the angle of the line of sight and the distance to an object at the end of the line of sight from the image of the eyeball, using the image of the eyeball and the direction in which the eyeball in the image was actually looking as teacher data. The AI ​​program may be included in the display device, the imaging device, or an external device. If included in the external device, it is transmitted to the display device via communication.

[0194] When display control is performed based on visual recognition detection, the present invention is preferably applicable to smart glasses that further include an imaging device for capturing images of the outside world. The smart glasses can display captured outside information in real time.

[0195] FIG. 10(a) is a schematic diagram showing an example of an image forming apparatus according to an embodiment of the present invention. The image forming apparatus 40 is an electrophotographic image forming apparatus, and includes a photoconductor 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transfer unit 32, a transport roller 33, and a fixing unit 35. Light 29 is irradiated from the exposure light source 28, and an electrostatic latent image is formed on the surface of the photoconductor 27. The exposure light source 28 includes an organic light-emitting element according to this embodiment. The developing unit 31 includes a toner, etc. The charging unit 30 charges the photoconductor 27. The transfer unit 32 transfers the developed image to a recording medium 34. The transport roller 33 transports the recording medium 34. The recording medium 34 is, for example, paper. The fixing unit 35 fixes the image formed on the recording medium 34.

[0196] 10(b) and 10(c) are diagrams showing the exposure light source 28, and are schematic diagrams showing a state in which a plurality of light-emitting sections 36 are arranged on a long substrate. Arrow 37 is a direction parallel to the axis of the photoconductor, and represents the column direction in which the organic light-emitting elements are arranged. This column direction is the same as the axis direction about which the photoconductor 27 rotates. This direction can also be called the long axis direction of the photoconductor 27. FIG. 10(b) shows a form in which the light-emitting sections 36 are arranged along the long axis direction of the photoconductor 27. FIG. 10(c) shows a form different from FIG. 10(b), in which the light-emitting sections 36 are alternately arranged in the column direction in each of the first column and the second column. The first column and the second column are arranged at different positions in the row direction. In the first column, a plurality of light-emitting sections 36 are arranged at intervals. In the second column, the light-emitting sections 36 are located at positions corresponding to the intervals between the light-emitting sections 36 in the first column. That is, a plurality of light-emitting sections 36 are also arranged at intervals in the row direction. The arrangement in FIG. 10(c) can also be described as a grid-like arrangement, a houndstooth arrangement, or a checkerboard pattern.

[0197] As described above, by using a device using the organic light-emitting element according to this embodiment, it is possible to achieve a display with good image quality and stability even over a long period of time.

[0198] ≪Included components≫ The disclosure of this embodiment includes the following configuration. (Configuration 1) An organometallic complex represented by the following general formula [1]: Ir(L) m (L') n [1] In formula [1], Ir is iridium. L and L' each represent a different bidentate ligand. m is 1 or 2, and m+n=3. Substructure Ir(L) m is a partial structure represented by the general formula [2-1] or [2-2]. In formula [2-1], R1 to R3 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. However, when at least one of R1 to R3 is not a hydrogen atom or a deuterium atom, and two of R1 to R3 are hydrogen atoms or deuterium atoms, the other of R1 to R3 is a substituted or unsubstituted secondary or higher alkyl group. Adjacent R1 to R3 may be bonded to each other to form a ring. R4 to R 14 are each independently selected from 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 silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted allyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, and a cyano group. 14 may be bonded to each other to form a ring. In formula [2-2], R 15 ~R 17 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. 15 ~R17 At least one of the atoms is not a hydrogen atom or a deuterium atom, and R 15 ~R 17 If two of are hydrogen or deuterium atoms, R 15 ~R 17 The other of the R is a substituted or unsubstituted secondary or higher alkyl group. 15 ~R 17 may be bonded to each other to form a ring. R 18 ~R 30 are each independently selected from 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 silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted allyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, and a cyano group. 18 ~R 30 may be bonded to each other to form a ring. L' is a bidentate ligand represented by the general formula [3] or [4]. In formula [3], R 41 ~R 43 are each independently selected from a hydrogen atom, a deuterium atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. 41 ~R 43 may be bonded to each other to form a ring. In formula [4], R 32 ~R 39 are each independently selected from a hydrogen atom, a deuterium atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted allyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. 32 ~R 39 may be bonded to each other to form a ring.

[0199] (Configuration 2) Said partial structure Ir(L) m is a partial structure represented by the general formula [2-1]. (Configuration 3) 3. The organometallic complex according to claim 2, wherein at least two of R1 to R3 are not hydrogen atoms or deuterium atoms. (Configuration 4) 4. The organometallic complex according to claim 3, wherein at least two of R1 to R3 are substituted or unsubstituted alkyl groups. (Configuration 5) Said partial structure Ir(L) m is a partial structure represented by the general formula [2-2]. (Configuration 6) R 15 ~R 18 At least two of the above are not hydrogen atoms or deuterium atoms. (Configuration 7) R 15 ~R 18 7. The organometallic complex according to claim 6, wherein at least two of the groups are substituted or unsubstituted alkyl groups. (Configuration 8) The R5 and the R 19 The organometallic complex according to any one of structures 1 to 7, wherein is not a hydrogen atom or a deuterium atom.

[0200] (Configuration 9) An organic light-emitting device comprising: a first electrode, a second electrode; and an organic compound layer disposed between the first electrode and the second electrode, the organic compound layer comprising a layer containing the organometallic complex according to any one of Structures 1 to 8. (Configuration 10) 10. The organic light-emitting device according to configuration 9, wherein the layer containing the organometallic complex is a light-emitting layer. (Configuration 11) 11. The organic light-emitting device according to claim 10, which emits red light. (Configuration 12) 12. The organic light-emitting element according to claim 10, further comprising another light-emitting layer disposed in a stacked manner with the light-emitting layer, the another light-emitting layer emitting a color different from the color of light emitted by the light-emitting layer. (Configuration 13) 13. The organic light-emitting device according to claim 12, which emits white light.

[0201] (Configuration 14) A display device comprising a plurality of pixels, at least one of the plurality of pixels comprising an organic light-emitting element according to any one of structures 9 to 13 and an active element connected to the organic light-emitting element. (Configuration 15) 15. The display device according to configuration 14, comprising a color filter. (Configuration 16) An input unit for inputting image information and a display unit for outputting an image, 16. An image display device, wherein the display unit comprises the display device according to configuration 14 or 15. (Configuration 17) an optical unit having a plurality of lenses, an image sensor that receives light that has passed through the optical unit, and a display unit that displays an image captured by the image sensor; 14. A photoelectric conversion device, wherein the display section comprises the organic light-emitting element according to any one of configurations 9 to 13. (Configuration 18) The device has a housing, a communication unit that communicates with the outside, and a display unit, 14. An electronic device, wherein the display unit is an organic light-emitting element as defined in any one of configurations 9 to 13. (Configuration 19) 14. An illumination device comprising: a light source having the organic light-emitting element according to any one of configurations 9 to 13; and a light diffusion section or an optical filter that transmits light emitted by the light source. (Configuration 20) The drone has a body and a lighting device provided on the body, The lighting device is a moving object having an organic light-emitting element according to any one of configurations 9 to 13. (Configuration 21) A photoconductor and an exposure light source that irradiates the photoconductor with light, 14. An image forming apparatus, wherein the exposure light source has the organic light-emitting element according to any one of configurations 9 to 13. EXAMPLES

[0202] The present invention will be described below with reference to examples, but the present invention is not limited to these.

[0203] [Example 1 (Synthesis of Exemplary Compound AA1)] [ka]

[0204] (1) Synthesis of compound G3 The following reagents and solvents were placed in a 500 ml recovery flask. Compound G1: 1.1g (5.15mmol) Compound G2: 1.0g (4.68mmol) Pd(Ph3)4: 162 mg (0.14 mmol) Na2CO3 aqueous solution (10%): 1.0g / 10ml water Toluene: 20 ml Ethanol: 10ml Next, the reaction solution was heated to 90° C. under a nitrogen stream and stirred at this temperature (90° C.) for 5 hours. After the reaction was completed, the mixture was extracted with toluene and water, concentrated, and purified by silica gel column chromatography (toluene), to obtain 1.1 g of compound G3 (yield: 70%).

[0205] (2) Synthesis of compound G4 After degassing a mixed solvent of 2-ethoxyethanol (40 ml) and water (10 ml), 226 mg (0.64 mmol) of iridium(III) chloride hydrate was added and stirred at room temperature for 30 minutes. Then, 0.44 g (1.28 mmol) of G3 was added, heated to 120 degrees, and stirred for 10 hours. After cooling, water was added, filtered, and washed with water and methanol. This was dried to obtain 0.51 g (90% yield) of red solid G4.

[0206] (3) Synthesis of Example Compound AA1 After degassing the 2-ethoxyethanol (10 ml) solvent, 0.18 g (0.10 mmol) of G4 and 50 mg (0.50 mmol) of G5 were added and stirred at room temperature for 30 minutes. Then, 69 mg (0.65 mmol) of sodium carbonate was added, heated to 120 degrees and stirred for 7 hours. After cooling, water was added, filtered, and washed with water and methanol. After purifying this by silica gel column chromatography (dichloromethane), 40 mg (yield: 37%) of exemplary compound AA1 was obtained.

[0207] In addition, mass spectrometry of the example compound AA1 was carried out using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker). [MALDI-TOF-MS] Measured value: m / z=968 Calculated value: C 55 H 55 IrN2O2=968

[0208] [Examples 2 to 51 (Synthesis of Exemplary Compounds)] Exemplary compounds were synthesized in the same manner as in Example 1, except that raw materials G1, G2, and G5 in Example 1 were replaced with raw materials 1, 2, and 3 shown in Tables 1 to 8, respectively. The actual measured values: m / z of the mass spectrometry results measured in the same manner as in Example 1 are also shown.

[0209] [Table 1]

[0210] [Table 2]

[0211] [Table 3]

[0212] [Table 4]

[0213] [Table 5]

[0214] [Table 6]

[0215] [Table 7]

[0216] [Table 8]

[0217] [Example 52 (Synthesis of Exemplary Compound B5)] [ka]

[0218] 100 ml of dichloromethane was added to 1.0 g (0.93 mmol) of G6, and the mixture was degassed with nitrogen. Then, 503 mg (1.96 mmol) of silver trifluoromethanesulfonate dissolved in 10 ml of methanol was added dropwise and stirred at room temperature for 8 hours. Then, the mixture was filtered (through Celite), washed with dichloromethane, and concentrated to obtain a yellow solid.

[0219] Next, 10 ml of diethylene glycol dimethyl ether was added to the obtained yellow solid and 170 mg (0.47 mmol) of G7, and the mixture was heated and stirred at 170° C. for 7 hours. After cooling, water was added, the mixture was filtered, and washed with water and methanol. After purifying the mixture by silica gel column chromatography (dichloromethane), 32 mg (yield: 8%) of exemplary compound B5 was obtained.

[0220] In the same manner as in Example 1, mass spectrometry of Example Compound B5 was carried out. [MALDI-TOF-MS] Measured value: m / z=1079 Calculated value: C 49 H 44 IrN3=867

[0221] [Examples 53 to 69 (Synthesis of Exemplary Compounds)] (1) Examples 53 and 62 A dichlorodimer derivative (a compound corresponding to G4) was synthesized in the same manner as in Example 1, except that raw materials G1 and G2 in Example 1 were changed to raw materials 1 and 2 shown in Tables 9 and 11, respectively. Furthermore, an example compound was synthesized in the same manner as in Example 52, except that raw material G6 in Example 52 was changed to the obtained dichlorodimer derivative, and raw material G7 was changed to raw material 5 shown in Tables 9 and 11. The actual measured value: m / z of the mass spectrometry result measured in the same manner as in Example 52 is also shown.

[0222] (2) Examples 54 to 61, 63 to 69 Exemplary compounds were synthesized in the same manner as in Example 52, except that raw materials G6 and G7 in Example 52 were replaced with raw materials 4 and 5 shown in Tables 9 to 12, respectively. The actual measured values: m / z of the mass spectrometry results measured in the same manner as in Example 52 are also shown.

[0223] [Table 9]

[0224] [Table 10]

[0225] [Table 11]

[0226] [Table 12]

[0227] [Examples 70 to 71, Comparative Examples 1 to 4 (Emission Spectra)] 1×10 of exemplified compounds AA1 and CC1 and comparative compounds 1-b, 2-b, 1-a, and 2-a -5 The emission spectrum of the toluene solution at mol / L was measured. The measurement was performed using a Hitachi F-4500 to measure the emission peak wavelength and half-width of photoluminescence at an excitation wavelength of 350 nm. The half-width was evaluated according to the following criteria. The results are shown in Table 13. The comparative compound 1-b is compound 1-a described in Patent Document 1. AA rank: 35nm or less A rank: over 35nm and under 40nm B rank: 40nm or more and less than 60nm C rank: 60nm or more

[0228] [Table 13]

[0229] As shown in Table 13, the emission wavelength is determined by the partial structure Ir(L) m is more preferred than the exemplary compound AA1 represented by the general formula [2-1], m However, the exemplary compound CC1 represented by the general formula [2-2] is preferable because it exhibits longer wavelength emission and has higher color purity.

[0230] Regarding the half-width, the comparative compounds that do not have a bulky substituent at the ortho-position of the benzene ring of the main ligand L are ranked B and C, whereas the exemplary compounds that have a bulky substituent at the same position are ranked A or higher, indicating high color purity.

[0231] [Example 72] An organic light-emitting device of bottom emission type structure was produced by sequentially forming an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode on a substrate.

[0232] First, an ITO film was formed on a glass substrate, and the desired patterning process was performed to form an ITO electrode (anode). At this time, the film thickness of the ITO electrode was set to 100 nm. The substrate on which the ITO electrode was formed was used as an ITO substrate in the following process. Next, a 1.33×10 -4 The organic compound layer and the electrode layer shown in Table 14 were successively formed on the ITO substrate by vacuum deposition using resistance heating in a vacuum chamber at 1000 Pa. Note that at this time, the electrode area of ​​the opposing electrode (metal electrode layer, cathode) was 3 mm 2 It was made so that:

[0233] [Table 14]

[0234] The characteristics of the obtained element were measured and evaluated. Table 15 shows the half-width of the emission spectrum of the light-emitting element, the maximum external quantum efficiency (EQE), and the current density at 100 mA / cm 2 The results of the measurement of the time when the brightness degradation rate reached 5% in a continuous driving test are shown below.

[0235] The half width was evaluated based on the following criteria, with the half width of Comparative Example 5 taken as 1. AA rank: 0.5 or less A rank: over 0.5 and below 0.7 B rank: over 0.7 and 1.0 or less C rank: Above 1.0

[0236] As for the maximum external quantum efficiency (EQE) and the time when the luminance degradation rate reached 5%, the measured value ratio is shown when the measured value of Comparative Example 5 is set to 1.0.

[0237] In this example, the measuring device was a microammeter 4140B manufactured by Hewlett-Packard Company to measure the current-voltage characteristics, and a BM7 manufactured by Topcon Corporation to measure the luminance.

[0238] [Examples 73 to 105, Comparative Examples 5 to 6] An organic light-emitting device was produced in the same manner as in Example 72, except that the compounds were appropriately changed to those shown in Tables 15 to 17. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 72. The results are shown in Tables 15 to 17.

[0239] [Table 15]

[0240] [Table 16]

[0241] [Table 17]

[0242] As shown in Tables 15 to 17, the half widths of Comparative Example 5 and Comparative Example 6 were C rank and B rank, respectively. On the other hand, the half widths of the Examples were narrow and were AA rank or A rank, and red light emission with high color purity was shown. This is because the organometallic complex according to this embodiment has a bulky substituent at the ortho position of the benzene ring of the main ligand L, thereby suppressing the molecular vibration of the main ligand L. In addition, since the organometallic complex according to this embodiment has a bulky substituent at the ortho position of the benzene ring of the main ligand L, the distance between the molecules is increased, thereby suppressing TTA, and the luminance deterioration rate was improved compared to the organic light-emitting device of the comparative example using the comparative compound.

[0243] The present invention is not limited to the above-described embodiments, and various modifications and variations can be made without departing from the spirit and scope of the present invention. Therefore, the following claims are appended to apprise the public of the scope of the present invention. [Explanation of symbols]

[0244] 1: interlayer insulating layer, 2: first electrode, 3: insulating layer, 4: organic compound layer, 5: second electrode, 6: protective layer, 7: color filter, 10: subpixel, 11: substrate, 12: insulating layer, 13: gate electrode, 14: gate insulating film, 15: semiconductor layer, 16: drain electrode, 17: source electrode, 18: TFT, 19: insulating film, 20: contact hole, 21: anode, 22: organic compound layer, 23: cathode, 24: first protective layer, 25: second protective layer, 26: organic light-emitting element, 100: display device

Claims

1. An organometallic complex represented by the following general formula [1]: Ir(L) m (L') n [1] In formula [1], Ir is iridium. L and L' each represent a different bidentate ligand. m is 2 and m+n=3. Substructure Ir(L) m is a partial structure represented by the following general formula [2-1] or [2-2]. 【Chemistry 1】 In formula [2-1], R 1 ~R 3 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. 1 ~R 3 At least one of R is not a hydrogen atom or a deuterium atom. 1 ~R 3 When two of R are hydrogen atoms or deuterium atoms, 1 ~R 3 The other of the R is a substituted or unsubstituted secondary or higher alkyl group. 1 ~R 3 may be bonded to each other to form a ring. R 4 ~R 14 are each independently selected from 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 silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted allyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, and a cyano group. 4 ~R 14 may be bonded to each other to form a ring. In formula [2-2], R 15 ~R 17 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. 15 ~R 17 At least one of R is not a hydrogen atom or a deuterium atom. 15 ~R 17 When two of R are hydrogen atoms or deuterium atoms, 15 ~R 17 The other of the R is a substituted or unsubstituted secondary or higher alkyl group. 15 ~R 17 may be bonded to each other to form a ring. R 18 ~R 30 are each independently selected from 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 silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted allyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, and a cyano group. 18 ~R 30 may be bonded to each other to form a ring. L' is a bidentate ligand represented by the following general formula [3] or [4]. 【Chemistry 2】 In formula [3], R 41 ~R 43 are each independently selected from a hydrogen atom, a deuterium atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. 41 ~R 43 may be bonded to each other to form a ring. In formula [4], R 32 ~R 39 are each independently selected from a hydrogen atom, a deuterium atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted allyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. 32 ~R 39 may be bonded to each other to form a ring.

2. An organometallic complex represented by the following general formula [1]: Ir(L) m (L') n [1] In formula [1], Ir is iridium. L and L' each represent a different bidentate ligand. m is 1 or 2, and m+n=3. The partial structure Ir(L) m is a partial structure represented by the following general formula [2-1] or [2-2]. 【Chemistry 1-1】 In formula [2-1], R 1 to R 3 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. However, when at least one of R 1 to R 3 is not a hydrogen atom or a deuterium atom, and two of R 1 to R 3 are hydrogen atoms or deuterium atoms, the other of R 1 to R 3 is a substituted or unsubstituted secondary or higher alkyl group. Adjacent R 1 to R 3 may be bonded to each other to form a ring. R4 to R14 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted allyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, and a cyano group. Adjacent R4 to R14 may be bonded to each other to form a ring. In formula [2-2], R 15 to R 17 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. However, when at least one of R 15 to R 17 is not a hydrogen atom or a deuterium atom, and two of R 15 to R 17 are hydrogen atoms or deuterium atoms, the other of R 15 to R 17 is a substituted or unsubstituted secondary or higher alkyl group. Adjacent R 15 to R 17 may be bonded to each other to form a ring. R18 to R30 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted allyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, and a cyano group. Adjacent R18 to R30 may be bonded to each other to form a ring. L' is a bidentate ligand represented by the following general formula [3] or [4]. 【Chemistry 2-1】 In formula [3], R 41 to R 43 are each independently selected from a hydrogen atom, a deuterium atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. Adjacent R 41 to R 43 may be bonded to each other to form a ring. In formula [4], R32 to R39 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted allyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. Adjacent R32 to R39 may be bonded to each other to form a ring.

3. The partial structure Ir(L) m is a partial structure represented by the general formula [2-1].

4. The R 1 ~R 3 4. The organometallic complex according to claim 3, wherein at least two of the groups are not hydrogen atoms or deuterium atoms.

5. The R 1 ~R 3 5. The organometallic complex according to claim 4, wherein at least two of the groups are substituted or unsubstituted alkyl groups.

6. The partial structure Ir(L) m is a partial structure represented by the general formula [2-2].

7. The R 15 ~R 18 7. The organometallic complex according to claim 6, wherein at least two of the groups are not hydrogen atoms or deuterium atoms.

8. The R 15 ~R 18 8. The organometallic complex according to claim 7, wherein at least two of the groups are substituted or unsubstituted alkyl groups.

9. The R 5 , the R 19 3. The organometallic complex according to claim 1, wherein is not a hydrogen atom or a deuterium atom.

10. 3. An organic light-emitting device comprising: a first electrode; a second electrode; and an organic compound layer disposed between the first electrode and the second electrode, the organic compound layer comprising a layer containing the organometallic complex according to claim 1.

11. The organic light-emitting element according to claim 10, wherein the layer containing the organometallic complex is a light-emitting layer.

12. The organic light-emitting device according to claim 11, which emits red light.

13. 12. The organic light-emitting element according to claim 11, further comprising another light-emitting layer disposed in a stacked state with the light-emitting layer, the another light-emitting layer emitting light of a color different from the color of light emitted by the light-emitting layer.

14. The organic light-emitting device according to claim 13, which emits white light.

15. A display device comprising a plurality of pixels, at least one of the plurality of pixels comprising the organic light-emitting element according to claim 10 and an active element connected to the organic light-emitting element.

16. 16. The display device according to claim 15, further comprising a color filter.

17. an input unit for inputting image information and a display unit for outputting an image; An image display device, wherein the display unit comprises the display device according to claim 15.

18. an optical unit having a plurality of lenses, an image pickup element that receives light that has passed through the optical unit, and a display unit that displays an image picked up by the image pickup element; The photoelectric conversion device according to claim 10, wherein the display section comprises the organic light-emitting element according to claim 10.

19. The device has a housing, a communication unit that communicates with the outside, and a display unit, The electronic device according to claim 10, wherein the display unit is an organic light-emitting element.

20. 11. A lighting device comprising: a light source having the organic light-emitting element according to claim 10; and a light diffusion section or an optical filter that transmits light emitted by the light source.

21. A drone includes a body and a lighting fixture provided on the body, A moving body, wherein the lighting device comprises the organic light-emitting element according to claim 10.

22. a photosensitive member and an exposure light source that irradiates the photosensitive member with light, 11. An image forming apparatus, wherein the exposure light source comprises the organic light emitting element according to claim 10.

Images