Organic compound and organic light-emitting element

Abstract

To provide an organic light-emitting element with superior color purity and durability.SOLUTION: One ligand L1 having a naphtho[2,1-f]isoquinoline skeleton and a tricyclic or polycyclic ring A bound thereto and two ligands L2 having a phenylpyridine skeleton are introduced into a molecule to form an iridium complex having superior color purity and thermal stability, and the iridium complex is incorporated as a guest into a light-emitting layer to produce an organic light-emitting element having superior color purity and durability.SELECTED DRAWING: None

Description

Technical Field

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

Background Art

[0002] An organic light-emitting device (hereinafter sometimes referred to as an "organic electroluminescence device" or an "organic EL device") is an electronic device having a pair of electrodes and an organic compound layer disposed between these electrodes. By injecting electrons and holes from these pair of electrodes, excitons of a light-emitting organic compound in the organic compound layer are generated, and when the excitons return to the ground state, the organic light-emitting device emits light. The recent progress of organic light-emitting devices is remarkable, and it can be mentioned that low driving voltage, various emission wavelengths, high-speed responsiveness, and thinning and weight reduction of light-emitting devices are possible. By the way, the creation of compounds suitable for organic light-emitting devices has been actively carried out until now. This is because the creation of compounds with excellent element lifetime characteristics is important in providing high-performance organic light-emitting devices. As the compounds created so far, the following iridium complexes are described in Patent Document 1.

[0003]

Chemical Formula

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0005] Patent Document 1 discloses the use of an iridium complex as a light-emitting material in the light-emitting layer of an organic light-emitting device, but further improvement in color purity and thermal stability is desired. The present invention has been made in view of the above problems, and an object thereof is to provide an organic compound excellent in color purity and thermal stability, and an organic light-emitting element excellent in color purity and durability characteristics using the same.

Means for Solving the Problems

[0006] The organic compound of the present invention is characterized by being represented by the following general formula [1]. Ir(L1)(L2)2 [1] 〔In the above general formula [1], the partial structure Ir(L1) is represented by the following general formula [1-1], and the partial structure Ir(L2)2 is represented by the following general formula [1-2].

[0007]

Chemical formula

[0008]

Chemical formula

Effects of the Invention

[0009] According to the present invention, an organic compound excellent in color purity and thermal stability can be provided. Further, by using the organic compound of the present invention as a light-emitting material of a light-emitting layer, an organic light-emitting device excellent in color purity and durability characteristics can be provided.

Brief Description of Drawings

[0010]

Figure 1

Figure 2

Figure 3

Figure 4

Figure 5

Figure 6

Figure 7

Embodiments for Carrying Out the Invention

[0011] Hereinafter, embodiments of the present invention will be described. The present invention is not limited to the following description, and it will be easily understood by those skilled in the art that its form and details can be variously changed without departing from the gist and scope of the present invention. That is, the present invention should not be construed as being limited by the following description.

[0012] 〔Organic Compound〕 First, the organic compound of the present invention will be described. The organic compound of the present invention is a compound represented by the following general formula [1]. Ir(L1)(L2)2 [1] In the above general formula [1], the partial structure Ir(L1) is represented by the following general formula [1-1], and the partial structure Ir(L2)2 is represented by the following general formula [1-2], respectively.

[0013]

Chemical Formula

[0014]

Chemical Formula

[0015] In the above general formula [1-1], ring A is selected from substituted or unsubstituted condensed rings of three or more rings. R1 to R 10 , and R 11 to R 18 in the above general formula [1-2] 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 aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, and a cyano group. R1 to R 10 , and R 11 to R 18 may be such that adjacent Rs are bonded to each other to form a ring. The two ligands L2 may have different structures from each other.

[0016] Examples of the condensed ring having three or more rings constituting ring A include, but are not limited to, a fluorene ring, an anthracene ring, a phenanthrene ring, a fluoranthene ring, a pyrene ring, a chrysene ring, a benzo[c]phenanthrene ring, a benzo[a]fluorene ring, a benzo[b]fluorene ring, a benzo[c]fluorene ring, a triphenylene ring, a perylene ring, an acridine ring, a phenanthroline ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzo[b]naphtho[1,2-d]furan ring, a benzo[b]naphtho[2,3-d]furan ring, a benzo[b]naphtho[2,1-d]furan ring, a benzo[b]naphtho[1,2-d]thiophene ring, a benzo[b]naphtho[2,3-d]thiophene ring, a benzo[b]naphtho[2,1-d]thiophene ring, an indolo[3,2,1-jk]carbazole ring, and the like. Among these, a fluorene ring, a phenanthrene ring, a dibenzofuran ring, a dibenzothiophene ring, and a carbazole ring are preferable.

[0017] At least one of R1 to R 10 in general formula [1-1], and at least one of R 11 to R 18 in general formula [1-2] are preferably selected from a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, and a cyano group.

[0018] Preferred examples of the halogen atom include fluorine, chlorine, bromine, iodine, and the like.

[0019] Examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a tert-butyl group, an iso-butyl group, a sec-butyl group, an octyl group, a dodecyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, and the like. Among these, a methyl group and a tert-butyl group are preferable.

[0020] Examples of the alkoxy group include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, a 2-ethyl-octyloxy group, a benzyloxy group, and the like.

[0021] Examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triphenylsilyl group, and the like.

[0022] Examples of the aryl group include, but are not limited to, a phenyl group, a naphthyl group, an indenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, an anthracenyl group, a phenanthryl group, a fluoranthenyl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a perylenyl group, and the like. Among these, a phenyl group, a biphenyl group, and a terphenyl group are preferable.

[0023] Examples of the heterocyclic group include, but are not limited to, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, a triazolyl group, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a quinolyl group, an acridinyl group, a phenanthrolinyl group, a dibenzofuranyl group, a dibenzothienyl group, and the like. Among these, a pyridyl group, a pyrimidyl group, a pyrazyl group, and a triazyl group are preferable. The heterocyclic group is preferably a heteroaryl group and is preferably a group bonded by a carbon atom.

[0024] Examples of the amino group include, but are not limited to, N-methylamino group, N-ethylamino group, N,N-dimethylamino group, N,N-diethylamino group, N-methyl-N-ethylamino group, N-benzylamino group, N-methyl-N-benzylamino group, N,N-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-dianisorylamino group, N-mesityl-N-phenylamino group, N,N-dimesitylamino group, N-phenyl-N-(4-tert-butylphenyl)amino group, N-phenyl-N-(4-trifluoromethylphenyl)amino group, N-piperidyl group, carbazolyl group, etc.

[0025] Examples of the aryloxy group and heteroaryloxy group include, but are not limited to, phenoxy group, thienyloxy group, etc.

[0026] Examples of the substituents that the tricyclic or higher condensed ring, alkyl group, alkoxy group, silyl group, aryl group, heterocyclic group, amino group, aryloxy group, heteroaryloxy group may further have include, but are not limited to, deuterium atom; halogen atoms such as fluorine, chlorine, bromine, iodine; alkyl groups such as methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, tert-butyl group; alkoxy groups such as methoxy group, ethoxy group, propoxy group; amino groups such as dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, ditolylamino group; aryloxy groups such as phenoxy group; aromatic hydrocarbon groups such as phenyl group, biphenyl group; heterocyclic groups such as pyridyl group, pyrrolyl group; cyano group, hydroxy group, thiol group, etc.

[0027] Also, the two ligands L2 may have different structures from each other.

[0028] The organic compound of the present invention is an iridium complex composed of a ligand L1 having a structure in which a naphtho[2,1-f]isoquinoline skeleton and a ring A which is a condensed ring of 3 or more rings are bonded, and a ligand L2 having a phenylpyridine skeleton. In the organic compound of the present invention, there is 1 L1 in the molecule and 2 L2s in the molecule, and by doing so, color purity and thermal stability can be achieved at a high level. Furthermore, when the organic compound of the present invention is used as a light-emitting material in the light-emitting layer of an organic light-emitting device, excellent durability characteristics can be achieved. The mechanism of its action effect will be described in detail below.

[0029] <Ring A> In general formula [1-1], ring A is a condensed ring bonded to the naphtho[2,1-f]isoquinoline skeleton and affects the phosphorescence characteristics of the organic compound represented by general formula [1]. Here, ring A is selected from substituted or unsubstituted condensed rings of 3 or more rings. By doing so, the organic compound represented by general formula [1] produces red phosphorescence with good color purity. Here, the red color in the present invention is light having a maximum peak wavelength of the emission spectrum of 590 nm or more and 640 nm or less. Furthermore, it is preferable that the red color with high color purity is 630 nm or more.

[0030] Here, in order to obtain red emission with higher color purity, ring A is preferably selected from a substituted or unsubstituted fluorene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted dibenzothiophene ring, and a substituted or unsubstituted carbazole ring.

[0031] As an index of the emission color, there are (X, Y) chromaticity coordinates in the CIE color system. In the NTSC standard, (0.670, 0.330) is the primary red point, and in BT.2020, (0.708, 0.292) is the primary red point. The larger the X value of the chromaticity coordinates and the smaller the Y value, the higher the red purity and the easier it is to improve the coverage rate. In the light-emitting layer of an organic light-emitting device, the light-emitting material tends to aggregate and the color purity deteriorates more than in solution. Therefore, as high-color-purity red, it is preferable that X is 0.69 or more and Y is 0.31 or less in solution.

[0032] Table 1 and 2 show the phosphorescence peak wavelengths and chromaticities calculated from the phosphorescence spectra of Exemplary Compound A-1 of the organic compound of the present invention and Comparative Compounds 1 to 7 that do not fall under the organic compound of the present invention in a toluene-diluted solution. Exemplary Compound A-1 and Comparative Compounds 3 and 4 have a ligand in which naphtho[2,1-f]isoquinoline and 9,9-dimethylfluorene are bonded, and have a chromaticity exceeding the red color of the NTSC standard, and thus can be suitably used for an organic light-emitting element for display applications. In contrast, Comparative Compounds 1 and 2 having a ligand in which benzo[f]isoquinoline and 9,9-dimethylfluorene are bonded had a chromaticity comparable to that of the red color of the NTSC standard. Further, Comparative Compound 5 having a ligand in which naphtho[2,1-f]isoquinoline and a benzene ring are bonded had a chromaticity inferior to that of the red color of the NTSC standard, and Comparative Compound 6 having a ligand in which naphtho[2,1-f]isoquinoline and a naphthalene ring which is a condensed ring of two rings are bonded had a chromaticity comparable to that of the red color of the NTSC standard. On the other hand, Comparative Compound 7 having a ligand in which naphtho[2,1-f]isoquinoline and a benzene ring are bonded and an acetylacetone ligand had a chromaticity slightly inferior to that of the red color of the NTSC standard. Incidentally, the phosphorescence spectrum was measured with a fluorescence spectrophotometer (F-4500, manufactured by Hitachi, Ltd.) after preparing a toluene solution of 1×10 -6 mol·dm -3 of each compound and performing nitrogen bubbling for 3 minutes.

[0033]

Table 1

[0034]

Table 2

[0035] <Ligand L1> The organic compound of the present invention has a ligand L1 having a naphtho[2,1-f]isoquinoline skeleton and a ligand L2 having a phenylpyridine skeleton as ligands for an iridium atom. While ligand L1 is a site that governs the luminescence properties, due to its high planarity, it becomes a factor that reduces sublimability due to stacking between molecules. Therefore, from the viewpoint of sublimability, it is preferable that only one ligand L1 exists in the molecule and two ligands L2 exist.

[0036] Table 3 shows the sublimation start temperature Ts [°C], decomposition temperature Td [°C], and the difference ΔT (=Td - Ts) [°C] between them for the exemplary compound A-1 of the organic compound of the present invention and Comparative Compounds 1 to 4 and 7 that do not correspond to the organic compound of the present invention. The larger ΔT is, the less likely decomposition occurs during the sublimation process such as sublimation purification or vapor deposition film formation, and the less likely the device performance deteriorates due to decomposition products. Among the compounds in Table 2, the ΔT values of the exemplary compound A-1 and Comparative Compound 1 are large, and they are preferable because they have excellent thermal stability. Next, Comparative Compounds 2 and 7 are applicable to the sublimation process, but since ΔT is small, there is a risk of decomposition depending on the heating state. For Comparative Compounds 3 and 4, decomposition occurred before the start of sublimation, so they are materials that cannot be used in the sublimation process and are not preferable.

[0037] In addition, the measurements of Ts and Td were performed using a thermogravimetric differential thermal analyzer (manufactured by Bruker). Specifically, -4 Under a vacuum on the order of 10 Pa, the sample was heated stepwise at a constant temperature every 10 °C from 300 °C to 420 °C for 10 minutes, and the temperature at which weight loss started was defined as Ts, and the temperature at which the decrease in vacuum due to thermal decomposition started was defined as Td. Here, the heating rate when raising the temperature to 300 °C is 10 °C / min, and the heating rate when raising the temperature by 10 °C each above 300 °C is 1 °C / min.

[0038]

Table 3

[0039] From the above results, in order to achieve both high color purity and high thermal stability, it is preferable to use an organic compound having one ligand L1 in the molecule in which a naphtho[2,1-f]isoquinoline skeleton and a ring A of three or more rings are bonded, and two ligands L2 each consisting of a phenylpyridine skeleton.

[0040] The following are examples of the specific structural formulas of the organic compounds of the present invention, but the present invention is not limited thereto.

[0041]

Chemical formula

[0042]

Chemical formula

[0043]

Chemical formula

[0044]

Chemical formula

[0045]

Chemical formula

[0046]

Chemical formula

[0047]

Chemical formula

[0048]

Chemical formula

[0049] [Chemistry]

[0050] [Chemistry]

[0051] [Chemistry]

[0052] [Chemistry]

[0053] [Chemistry]

[0054] Compounds belonging to Group A are compounds in which ring A, which is a substituted or unsubstituted condensed ring of three or more rings, is an aryl group. Compounds belonging to Group A are more thermally stable because ring A consists of a stable aryl group, which is preferable. That is, Group A is a group of compounds having even higher durability performance when used in an organic light-emitting device.

[0055] Compounds belonging to Group B are compounds in which ring A, which is a substituted or unsubstituted condensed ring of three or more rings, is a heterocyclic group. Compounds belonging to Group B can obtain various phosphorescence spectrum peak wavelengths due to the electronic effect of heteroatoms because ring A consists of a heterocyclic group, which is preferable. Therefore, Group B is a group of compounds that can achieve a desired color purity when used in an organic light-emitting device.

[0056] Compounds belonging to Group C are compounds having a substituent on at least the naphtho[2,1-f]isoquinoline skeleton. Compounds belonging to Group C are preferable because they have a wide range of phosphorescence characteristics and sublimability. That is, Group C is a group of compounds having good color purity and higher durability performance when used in an organic light-emitting device.

[0057] The compounds belonging to Group D are compounds having substituents at least on ligand L2. The compounds belonging to Group D can suppress aggregation and improve sublimability, which is preferable. That is, Group D is a group of compounds having good color purity and even higher durability performance when used in an organic light-emitting device.

[0058] 〔Organic Light-Emitting Device〕 The organic light-emitting device of the present invention has a pair of electrodes and an organic compound layer disposed between the pair of electrodes, and the organic compound layer contains the organic compound of the present invention. Preferably, the organic compound layer has a light-emitting layer, the light-emitting layer has the organic compound of the present invention, and more preferably, the organic compound of the present invention is used as the first organic compound and further contains a second organic compound.

[0059] As a specific device configuration of the organic light-emitting device of the present invention, a multilayer device configuration in which an electrode layer and an organic compound layer shown in the following (a) to (f) are sequentially laminated on a substrate can be mentioned. In any device configuration, the organic compound layer always contains a light-emitting layer having a light-emitting material. (a) Anode / Light-Emitting Layer / Cathode (b) Anode / Hole Transport Layer / Light-Emitting Layer / Electron Transport Layer / Cathode (c) Anode / Hole Transport Layer / Light-Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode (d) Anode / Hole Injection Layer / Hole Transport Layer / Light-Emitting Layer / Electron Transport Layer / Cathode (e) Anode / Hole Injection Layer / Hole Transport Layer / Light-Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode (f) Anode / Hole Transport Layer / Electron Blocking Layer / Light-Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Cathode However, these device configuration examples are only very basic device configurations, and the device configuration is not limited to these. For example, an insulating layer, an adhesive layer or an interference layer can be provided at the interface between the electrode and the organic compound layer, the electron transport layer or the hole transport layer is composed of two layers having different ionization potentials, the light-emitting layer is composed of two layers having different light-emitting materials, etc. A variety of layer configurations can be adopted.

[0060] Also, the light-emitting layer may be a single layer or a multiple layer. The multiple layer means a state where a light-emitting layer and another light-emitting layer are stacked. For example, a light-emitting layer containing the organic compound of the present invention as a guest molecule and a host molecule, and another light-emitting layer that emits a color different from the light-emitting color emitted by this light-emitting layer may be stacked. In this case, the light-emitting color may be white or an intermediate color.

[0061] In the device configurations shown in the above (a) to (f), the configuration of (f) is preferable because it has both an electron blocking layer and a hole blocking layer. That is, in (f) having an electron blocking layer and a hole blocking layer, both carriers of holes and electrons can be surely confined in the light-emitting layer, so that an organic light-emitting device with no carrier leakage and high luminous efficiency can be obtained.

[0062] As a light extraction mode (device form) of the light output from the light-emitting layer, a so-called bottom emission method of extracting light from the electrode on the substrate side may be used, or a so-called top emission method of extracting light from the opposite side of the substrate may be used. Also, a double-sided extraction method of extracting light from both the substrate side and the opposite side of the substrate can be adopted.

[0063] In the organic light-emitting device of the present invention, the organic compound of the present invention is preferably included in the light-emitting layer among the organic compound layers. At this time, the compounds included in the light-emitting layer have different uses depending on the content concentration in the light-emitting layer. Specifically, depending on the content concentration in the light-emitting layer, they are divided into a main component and a sub-component.

[0064] The compound that becomes the main component is the compound with the largest mass ratio (content concentration) among the compound group included in the light-emitting layer, and is also called a host. The host is a compound that exists as a matrix around the light-emitting material in the light-emitting layer, and mainly undertakes the transport of carriers to the light-emitting material and the supply of excitation energy to the light-emitting material.

[0065] In addition, the compound serving as a sub-component is a compound other than the main component, and depending on the function of the compound, it can be called a guest (dopant), a luminescence assist material, or a charge injection material. A guest, which is one type of sub-component, is a compound (luminescent material) that is mainly responsible for luminescence within the light-emitting layer. A luminescence assist material, which is one type of sub-component, is a compound that assists the luminescence of the guest, and is a compound with a mass ratio (content concentration) within the light-emitting layer that is smaller than that of the host. The luminescence assist material is also called a second host due to its function.

[0066] The concentration of the host is preferably 50% by weight or more and 99% by weight or less, more preferably 70% by weight or more and 99% by weight or less, based on the total amount of the constituent materials of the light-emitting layer. The concentration of the guest is 0.01% by mass or more and less than 50% by mass, preferably 0.1% by mass or more and 20% by mass or less, based on the total amount of the constituent materials of the light-emitting layer. From the viewpoint of reducing concentration quenching, the concentration of the guest is particularly preferably 10% by mass or less. The concentration of the luminescence assist material is 0.1% by mass or more and less than 50% by mass, preferably 1% by mass or more and less than 50% by mass, based on the total amount of the constituent materials of the light-emitting layer.

[0067] The guest may be uniformly contained throughout the layer in which the host forms the matrix, or may be contained with a concentration gradient. Further, the guest may be partially contained in a specific region within the layer, such that the light-emitting layer has a region that contains only the host without the guest.

[0068] In the present invention, an embodiment in which the organic compound of the present invention is contained as a guest in the light-emitting layer is preferred. Thus, the light-emitting layer contains a second organic compound as the host, and may further contain a third organic compound (second host) for the purpose of assisting the transfer of excitons and carriers.

[0069] (1) First organic compound The first organic compound is preferably a guest, and is preferably the organic compound of the present invention.

[0070] (2) Second organic compound The second organic compound is preferably a host. Examples of the host material include, in addition to aromatic hydrocarbon compounds or their derivatives, carbazole derivatives, azine derivatives, xanthone derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, and organoaluminum complexes such as tris(8-quinolinolato)aluminum, and organoberyllium complexes.

[0071] Among these, materials having a carbazole skeleton, materials having a triphenylene ring as a skeleton, and materials having a dibenzothiophene skeleton are preferred. This is because these materials have high electron-donating and electron-withdrawing properties, making it easy to adjust the HOMO (highest occupied molecular orbital) level and LUMO (lowest unoccupied molecular orbital) level. When these host materials are combined with the organic compound of the present invention, a good carrier balance can be achieved.

[0072] Specific examples of the organic compound used as the host material contained in the light-emitting layer are shown below, but of course, the present invention is not limited thereto. Among the following specific examples, the materials having a carbazole skeleton, which are preferred as host materials, are EM32 to EM38. Also, the materials having a triphenylene ring as a skeleton, which are preferred as host materials, are EM10 to EM14, EM32, and EM39. Also, the materials having a dibenzothiophene skeleton, which are preferred as host materials, are EM13, EM14, and EM28.

[0073]

Chemical formula

[0074]

Chemical formula

[0075]

Chemical formula

[0076] (3) The third organic compound (second host, light-emitting assist material) As the second light-emitting layer host or light-emitting assist material contained in the light-emitting layer of the organic light-emitting device of the present invention, a third organic compound may be contained. Examples of the third organic compound include the host materials and phosphorescent organometallic complexes exemplified as specific examples of the second organic compound.

[0077] Specific examples of the phosphorescent organometallic complexes used as the light-emitting assist material include iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, and the like.

[0078] From the viewpoint of the light-emission quantum yield, more preferably, the light-emitting assist material is an organometallic complex represented by the following general formula [2]. M(L) m (L’) n [2] In the above general formula [2], M is selected from iridium and platinum.

[0079] L and L’ each represent a different bidentate ligand, and when there are a plurality of L or L’, they may be the same or different from each other.

[0080] m is selected from integers of 1 or more and 3 or less, and n is selected from integers of 0 or more and 2 or less. However, when M is iridium, m + n = 3, and when M is platinum, m + n = 2.

[0081] The partial structure M(L) m is represented by the following general formula [2-1], and the partial structure M(L) n is represented by the following general formula [2-2].

[0082]

Chemical formula

[0083]

Chemical formula

[0084] R in the general formula [2-1]21 up to R 28 and R in general formula [2-2] 39 up to R 41 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 aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, and a cyano group. Further, R 21 up to R 28 and R 39 up to R 41 may be such that adjacent Rs are bonded to each other to form a ring.

[0085] Examples of the halogen atom include, but are not limited to, fluorine, chlorine, bromine, iodine, etc. Among these, a fluorine atom is preferable.

[0086] Examples of the alkyl group include, but are not limited to, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, tert-butyl group, sec-butyl group, octyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, etc.

[0087] Examples of the alkoxy group include, but are not limited to, methoxy group, ethoxy group, propoxy group, 2-ethyl-octyloxy group, benzyloxy group, etc.

[0088] Examples of the silyl group include, but are not limited to, trimethylsilyl group, triphenylsilyl group, etc.

[0089] Examples of the aryl group include, but are not limited to, phenyl group, naphthyl group, indenyl group, biphenyl group, terphenyl group, fluorenyl group, phenanthryl group, fluoranthenyl group, triphenylenyl group, etc.

[0090] Examples of the heterocyclic group include, but are not limited to, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazolyl group, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a carbazolyl group, an acridinyl group, a phenanthrolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, etc. The heterocyclic group is preferably a heteroaryl group and preferably a group bonded by a carbon atom.

[0091] Examples of the amino group include, but are not limited to, an N-methylamino group, an N-ethylamino group, an N,N-dimethylamino group, an N,N-diethylamino group, an N-methyl-N-ethylamino group, an N-benzylamino group, an N-methyl-N-benzylamino group, an N,N-dibenzylamino group, an anilino group, an N,N-diphenylamino group, an N,N-dinaphthylamino group, an N,N-difluorenylamino group, an N-phenyl-N-tolylamino group, an N,N-ditolylamino group, an N-methyl-N-phenylamino group, an N,N-dianisorylamino group, an N-mesityl-N-phenylamino group, an N,N-dimesitylamino group, an N-phenyl-N-(4-tert-butylphenyl)amino group, an N-phenyl-N-(4-trifluoromethylphenyl)amino group, an N-piperidyl group, a carbazolyl group, etc.

[0092] Examples of the aryloxy group and the heteroaryloxy group include, but are not limited to, a phenoxy group, a thienyloxy group, etc.

[0093] Examples of substituents that an alkyl group, an alkoxy group, a silyl group, an aryl group, a heterocyclic group, an amino group, an aryloxy group, or a heteroaryloxy group may further have include, for example, a deuterium atom; a halogen atom such as fluorine, chlorine, bromine, or iodine; an alkyl group such as a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, or a tert-butyl group; an alkoxy group such as a methoxy group, an ethoxy group, or a propoxy group; an amino group such as a dimethylamino group, a diethylamino group, a dibenzylamino group, a diphenylamino group, or a ditolylamino group; an aryloxy group such as a phenoxy group; an aromatic hydrocarbon group such as a phenyl group or a biphenyl group; a heterocyclic group such as a pyridyl group or a pyrrolyl group; a cyano group, a hydroxy group, a thiol group, etc., but are not limited thereto.

[0094] Also, adjacent R 21 to R 28 , preferably, adjacent R 21 to R 24 or adjacent R 25 to R 28 may be bonded to each other to form a ring. Adjacent R 21 to R 28 being bonded to each other to form a ring means that the ring formed by the bonding of R 21 and R 22 , R 22 and R 23 , R 23 and R 24 condenses with the benzene ring to which R 21 to R 24 is bonded to form a fused ring, or the ring formed by the bonding of R 25 and R 26 , R 26 and R 27 , R 27 and R 28 condenses with the pyridine ring to which R 25 to R 28 is bonded to form a fused ring. The ring formed by the bonding of adjacent R 21 to R 28 may be an aromatic ring.

[0095] Among the organometallic complexes represented by the general formula [2], the partial structure M(L) m is preferably an organometallic complex having a condensed ring of 3 or more rings. This is because the planarity is improved by the condensed ring skeleton of 3 or more rings, the energy transfer from the host molecule is promoted, leading to higher efficiency and improved durability. Examples of the condensed ring of 3 or more rings include a phenanthrene ring, a triphenylene ring, a benzofluorene ring, a dibenzofuran ring, a dibenzothiophene ring, a benzonaphthofuran ring, a benzonaphthothiophene ring, a benzoisoquinoline ring, a naphthoisoquinoline ring, and the like.

[0096] Also, in the general formula [2-1], R 22 , R 23 , R 26 , R 27 is preferably at least one of a substituted or unsubstituted aryl group and a substituted or unsubstituted heterocyclic group. This is because the planarity of the organometallic complex is improved as described above.

[0097] The following shows more preferred general formulas of the partial structure M(L) represented by the general formula [2-1] m , but is not limited thereto. In the general formulas shown below, the coordination bond is indicated by a straight line, a dotted line or an arrow.

[0098]

Chemical formula

[0099]

Chemical formula

[0100] In the above general formulas [Ir-5] to [Ir-8], [Ir-15] to [Ir-16], X' is selected from an oxygen atom, a sulfur atom, a substituted or unsubstituted carbon atom, and a substituted or unsubstituted nitrogen atom.

[0101] The general formulas [Ir-2] to [Ir-8] have adjacent R 21 to R 24are bonded to each other to form a ring. General formulas [Ir-9] to [Ir-16] represent that adjacent R 25 to R 28 are bonded to each other to form a ring. Also, general formulas [Ir-3] to [Ir-8] represent that at least one of R 21 to R 24 is a phenyl group or a naphthyl group and forms a ring with an adjacent group. General formulas [Ir-11] to [Ir-16] represent that at least one of R 25 to R 28 is a phenyl group or a naphthyl group and forms a ring with an adjacent group. Therefore, general formulas [Ir-3] to [Ir-8], [Ir-11] to [Ir-16] may or may not further have an aryl group or a heterocyclic group.

[0102] Substructure M(L) m Among the metal complexes represented by the above general formulas [Ir-1] to [Ir-16], more preferably, it is a metal complex having a fused ring of 3 rings or more as a ligand. Specifically, substructure M(L) m is a metal complex represented by the above general formulas [Ir-3] to [Ir-8], [Ir-11] to [Ir-16]. Specific examples thereof are shown below, but of course, it is not limited thereto.

[0103]

Chemical formula

[0104]

Chemical formula

[0105]

Chemical formula

[0106]

Chemical formula

[0107] [Chemistry]

[0108] [Chemistry]

[0109] [Chemistry]

[0110] [Chemistry]

[0111] [Chemistry]

[0112] [Chemistry]

[0113] [Chemistry]

[0114] [Chemistry]

[0115] [Chemistry]

[0116] [Chemistry]

[0117] [Chemistry]

[0118]

Chem.

[0119]

Chem.

[0120]

Chem.

[0121]

Chem.

[0122]

Chem.

[0123]

Chem.

[0124]

Chem.

[0125]

Chem.

[0126]

Chem.

[0127]

Chem.

[0128]

Chem.

[0129] [Chemistry]

[0130] [Chemistry]

[0131] [Chemistry]

[0132] [Chemistry]

[0133] [Chemistry]

[0134] [Chemistry]

[0135] Exemplary compounds belonging to Group AA have a partial structure M(L) m which is an organometallic complex represented by the general formula [Ir-4] and is a compound having at least a triphenylene ring in the ligand. Since these compounds consist of condensed rings with sp 2 hybrid orbitals, they are particularly excellent in stability.

[0136] Exemplary compounds belonging to Group BB to Group CC have a partial structure M(L) m which is an organometallic complex represented by the general formula [Ir-3] and is a compound having at least a phenanthrene ring in the ligand. Since these compounds consist of condensed rings with sp 2 hybrid orbitals, they are particularly excellent in stability.

[0137] Exemplary compounds belonging to group DD have the partial structure M(L) m which is an organometallic complex represented by general formulas [Ir-5] to [Ir-8], and is a compound having at least a dibenzofuran ring, a dibenzothiophene ring, a benzonaphthofuran ring, or a benzonaphthothiophene ring in the ligand. These compounds contain an oxygen atom or a sulfur atom in the condensed ring, and the rich lone pairs of electrons possessed by these atoms can enhance the charge transport property. Therefore, they are particularly compounds that are easy to adjust the carrier balance.

[0138] Exemplary compounds belonging to groups EE to GG have the partial structure M(L) m which is an organometallic complex represented by general formulas [Ir-6] to [Ir-8], and is a compound having at least a benzofluorene ring in the ligand. Since these compounds have a substituent at the 9-position of the fluorene ring in a direction perpendicular to the in-plane direction of the fluorene ring, the overlapping of the condensed rings can be particularly reduced. Therefore, they are particularly compounds with excellent sublimability.

[0139] Exemplary compounds belonging to group HH have the partial structure M(L) m which is an organometallic complex represented by general formulas [Ir-11] to [Ir-13], and is a compound having at least a benzoisoquinoline ring in the ligand. These compounds contain an N atom in the condensed ring, and the lone pairs of electrons and high electronegativity possessed by these atoms can enhance the charge transport property. Therefore, they are particularly compounds that are easy to adjust the carrier balance.

[0140] Exemplary compounds belonging to group II have the partial structure M(L) m which is an organometallic complex represented by general formula [Ir-14], and is a compound having at least a naphthoisoquinoline ring in the ligand. These compounds contain an N atom in the condensed ring, and the lone pairs of electrons and high electronegativity possessed by these atoms can enhance the charge transport property. Therefore, they are particularly compounds that are easy to adjust the carrier balance.

[0141] (4) Other compounds In the organic light-emitting device of the present invention, if necessary, conventionally known low-molecular and high-molecular hole injection compounds or hole transport compounds, light-emitting compounds, electron injection compounds or electron transport compounds, etc. can be used together. Examples of these compounds are given below.

[0142] As the hole injection and transport material, a material with a high hole mobility is preferable so as to facilitate the injection of holes from the anode and transport the injected holes to the light-emitting layer. Further, in order to reduce the deterioration of the film quality such as crystallization in the organic light-emitting device, a material with a high glass transition temperature (Tg) is preferable. Examples of low-molecular and high-molecular materials having hole injection and transport performance include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. Furthermore, the above hole injection and transport materials are also preferably used for the electron blocking layer. Specific examples of the compounds used as the hole injection and transport materials are shown below, but of course, they are not limited to these.

[0143] [Chemical formula]

[0144] In the light-emitting layer of the organic light-emitting device of the present invention, guest molecules may be contained in addition to the organic compound represented by the general formula [1]. Examples of guest molecules mainly related to the light-emitting function include condensed ring compounds (for example, 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(phenylene vinylene) derivatives, poly(fluorene) derivatives, and poly(phenylene) derivatives. Specific examples of the compounds used as the light-emitting materials are shown below, but of course, they are not limited to these.

[0145]

Chem.

[0146]

Chem.

[0147] As the electron transporting material, it can be arbitrarily selected from those capable of transporting electrons injected from the cathode to the light emitting layer, and is selected in consideration of the balance with the hole mobility of the hole transporting material. Examples of the material having electron transporting performance include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organic aluminum complexes, condensed ring compounds (for example, fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the above electron transporting material is also preferably used for the hole blocking layer. Specific examples of the compound used as the electron transporting material are shown below, but of course, it is not limited thereto.

[0148]

Chem.

[0149]

Chem.

[0150] (5) Structure of the organic light emitting device The organic light emitting device 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 planarization layer may be provided between the protective layer. The planarization layer can be composed of an acrylic resin or the like. The same applies when a planarization layer is provided between the color filter and the microlens.

[0151] [Substrate] Examples of the substrate include quartz, glass, silicon wafers, resins, metals, etc. Further, the substrate may be provided with switching elements such as transistors and wirings, and an insulating layer may be provided thereon. As the insulating layer, any material may be used as long as a contact hole can be formed so that a wiring can be formed between the insulating layer and the first electrode, and insulation from non-connected wirings can be ensured. For example, resins such as polyimide, silicon oxide, silicon nitride, etc. can be used.

[0152] [Electrode] A pair of electrodes can be used as the electrodes. The pair of electrodes may be an anode and a cathode. When an electric field is applied in the direction in which the organic light-emitting element emits light, the electrode with a higher potential is the anode, and the other is the cathode. Also, it can be said that the electrode that supplies holes to the light-emitting layer is the anode, and the electrode that supplies electrons is the cathode.

[0153] As the constituent material of the anode, those with as large a work function as possible are preferable. For example, simple metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, tungsten, etc., mixtures containing these, alloys combining these, metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide, etc. can be used. Also, conductive polymers such as polyaniline, polypyrrole, polythiophene, etc. can be used.

[0154] These electrode materials may be used alone or in combination of two or more. Also, the anode may be composed of a single layer or multiple layers.

[0155] When used as a reflective electrode, for example, chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys thereof, laminated materials, etc. can be used. With the above materials, it is also possible to function as a reflective film without having the role of an electrode. When used as a transparent electrode, oxide transparent conductive layers such as indium tin oxide (ITO) and indium zinc oxide can be used, but it is not limited thereto. For the formation of the electrode, photolithography technology can be used.

[0156] On the other hand, as the constituent material of the cathode, those with a small work function are preferable. For example, alkali metals such as lithium, alkaline earth metals such as calcium, single metals such as aluminum, titanium, manganese, silver, lead, chromium, or mixtures containing these can be mentioned. Alternatively, alloys combining these single metals can also be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper, zinc-silver, etc. can be used. The use of metal oxides such as indium tin oxide (ITO) is also possible. These electrode materials may be used alone or in combination of two or more. Also, the cathode may have a single-layer structure or a multi-layer structure. Among them, it is preferable to use silver, and in order to reduce the aggregation of silver, it is more preferable to use a silver alloy. As long as the aggregation of silver can be reduced, the ratio of the alloy does not matter. For example, silver: other metals may be 1:1, 3:1, etc.

[0157] 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. As the method for forming the cathode, although not particularly limited, the use of direct current and alternating current sputtering methods, etc. is more preferable because the film coverage is good and the resistance is easily reduced.

[0158] [Organic compound layer] The organic compound layer may be formed as a single layer or multiple layers. When there are multiple layers, depending on their functions, they may be referred to as a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. The organic compound layer is mainly composed of organic compounds, but may also contain inorganic atoms or inorganic compounds. For example, it may contain copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, etc. The organic compound layer may be disposed between the first electrode and the second electrode, and may also be arranged in contact with the first electrode and the second electrode.

[0159] The organic compound layer (such as a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc.) constituting the organic light-emitting device according to an embodiment of the present invention is formed by the method shown below.

[0160] For the organic compound layer constituting the organic light-emitting device according to an embodiment of the present invention, dry processes such as vacuum evaporation, ionization evaporation, sputtering, and plasma can be used. Instead of the dry process, a wet process of dissolving in an appropriate solvent and forming a layer by a known coating method (for example, spin coating, dipping, casting method, LB method, inkjet method, etc.) can also be used.

[0161] Here, when forming a layer by a vacuum evaporation method, a solution coating method, etc., crystallization, etc. hardly occur and the stability over time is excellent. Also, when forming a film by a coating method, a film can be formed in combination with an appropriate binder resin. Examples of the binder resin include, but are not limited to, polyvinyl carbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, urea resin, etc. These binder resins may be used alone as a homopolymer or a copolymer, or two or more kinds may be mixed and used. Furthermore, additives such as known plasticizers, antioxidants, and ultraviolet absorbers may be used in combination as needed.

[0162] [Protective layer] A protective layer may be provided on the second electrode. For example, by adhering a glass provided with a moisture absorbent on the second electrode, the intrusion of water or the like into the organic compound layer can be reduced, and the occurrence of display defects can be reduced. Further, as another embodiment, a passivation film such as silicon nitride may be provided on the second electrode to reduce the intrusion of water or the like into the organic compound layer. For example, after forming the second electrode, it may be transferred to another chamber without breaking the vacuum, and a silicon nitride film with a thickness of 2 μm may be formed by CVD method to be used as a protective layer. A protective layer using atomic layer deposition (ALD method) may be provided after the film formation by CVD method. The material of the film by ALD method is not limited, but it may be silicon nitride, silicon oxide, aluminum oxide, etc. Silicon nitride may be further formed by CVD method on the film formed by ALD method. The film by ALD method may have a smaller film thickness than the film formed by CVD method. Specifically, it may be 50% or less, and further 10% or less.

[0163] [Color filter] A color filter may be provided on the protective layer. For example, a color filter considering the size of the organic light-emitting element may be provided on another substrate and bonded to the substrate provided with the organic light-emitting element, or the color filter may be patterned using photolithography technology on the protective layer shown above. The color filter may be composed of a polymer.

[0164] [Planarization layer] A planarization layer may be provided between the color filter and the protective layer. The planarization layer is provided for the purpose of reducing the unevenness of the underlying layer. Without limiting the purpose, it may be called a resin layer in some cases. The planarization layer may be composed of an organic compound, and may be a low molecule or a polymer, but a polymer is preferable. The planarization layer may be provided above and below the color filter, and the constituent materials thereof may be the same or different. Specifically, examples include polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, urea resin, and the like.

[0165] [Micro lens] The organic light-emitting element or the organic light-emitting device having the organic light-emitting element may have an optical member such as a micro lens on its light-emitting side. The micro lens can be made of acrylic resin, epoxy resin, or the like. The micro lens may be for the purpose of increasing the amount of light extracted from the organic light-emitting element or the organic light-emitting device and controlling the direction of the extracted light. The micro lens may have a hemispherical shape. When having a hemispherical shape, among the tangents in contact with the hemisphere, there is a tangent parallel to the insulating layer, and the contact point between the tangent and the hemisphere is the vertex of the micro lens. The vertex of the micro lens can be determined similarly in any cross-sectional view. That is, among the tangents in contact with the semi-circle of the micro lens in the cross-sectional view, there is a tangent parallel to the insulating layer, and the contact point between the tangent and the semi-circle is the vertex of the micro lens. Also, the midpoint of the micro lens can be defined. In the cross-section of the micro lens, a line segment from the point where the arc shape ends to the point where another arc shape ends is imagined, and the midpoint of the line segment can be called the midpoint of the micro lens. The cross-section for discriminating the vertex and the midpoint may be a cross-section perpendicular to the insulating layer.

[0166] [Counter substrate] A counter substrate may be provided on the planarization layer. Since the counter substrate is provided at a position corresponding to the aforementioned substrate, it is called a counter substrate. The constituent material of the counter substrate may be the same as that of the aforementioned substrate. When the aforementioned substrate is the first substrate, the counter substrate may be the second substrate.

[0167] [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 light emission of a plurality of light-emitting elements independently. The active matrix type circuit may be voltage programming or current programming. The driving circuit has a pixel circuit for each pixel. The pixel circuit may have a light-emitting element, a transistor that controls the light emission luminance of the light-emitting element, a transistor that controls the light emission timing, a capacitor that holds the gate voltage of the transistor that controls the light emission luminance, and a transistor for connecting to GND without passing through the light-emitting element.

[0168] The light-emitting device has a display area and a peripheral area arranged around the display area. The display area has a pixel circuit, and the peripheral area has a display control circuit. The mobility of the transistors constituting the pixel circuit may be smaller than the mobility of the transistors constituting the display control circuit. The slope of the current-voltage characteristics of the transistors constituting the pixel circuit may be smaller than the slope of the current-voltage characteristics of the transistors constituting the display control circuit. The slope of the current-voltage characteristics can be measured by so-called Vg-Ig characteristics. The transistors constituting the pixel circuit are transistors connected to a light-emitting element such as a first light-emitting element.

[0169] [Pixel] An organic light-emitting device having an organic light-emitting element may have a plurality of pixels. The pixels have sub-pixels that emit different colors from each other. The sub-pixels may have, for example, light emission colors of RGB respectively.

[0170] Light is emitted from a region also called a pixel aperture. The pixel aperture may be 15 μm or less and may be 5 μm or more. More specifically, it may be 11 μm, 9.5 μm, 7.4 μm, 6.4 μm, etc. The distance between sub-pixels may be 10 μm or less, and specifically may be 8 μm, 7.4 μm, 6.4 μm. In a plan view, the pixels can adopt known arrangement forms. For example, they may be in a stripe arrangement, a delta arrangement, a pentile arrangement, or a Bayer arrangement. The shape of the sub-pixels in a plan view can be any known shape. For example, it can be a quadrilateral such as a rectangle or a rhombus, a hexagon, etc. Of course, even if it is not an exact figure but a shape close to a rectangle, it is included in the rectangle. The shape of the sub-pixels and the pixel array can be used in combination.

[0171] (6) Device using an organic light-emitting element The organic light-emitting element of the present invention can be used as a constituent member of a display device or a lighting device. In addition, there are applications such as an exposure light source of an electrophotographic image forming device, a backlight of a liquid crystal display device, and a light-emitting device having a color filter for a white light source.

[0172] The display device may be an image information processing device having an image input unit for inputting image information from an area CCD, a linear CCD, a memory card, etc., having an information processing unit for processing the input information, and displaying the input image on a display unit. The display device has a plurality of pixels, and at least one of the plurality of pixels has the organic light-emitting element of the present invention and a transistor connected to the organic light-emitting element. At this time, the substrate may be a semiconductor substrate such as silicon, and the transistor may be a MOSFET formed on the substrate.

[0173] In addition, the display unit of an imaging device or an inkjet printer may have a touch panel function. The driving method of this touch panel function may be an infrared method, a capacitance method, a resistive film method, or an electromagnetic induction method, and is not particularly limited. Also, the display device may be used for the display unit of a multifunction printer.

[0174] Next, the display device according to this embodiment will be described with reference to the drawings. FIG. 1 is a schematic cross-sectional view showing an example of a display device having an organic light-emitting element and a transistor connected to this organic light-emitting element. The transistor is an example of an active element. The transistor may be a thin film transistor (TFT).

[0175] FIG. 1(a) shows an example of a pixel which is a component of the display device according to the present embodiment. The pixel has sub-pixels 10. The sub-pixels are divided into 10R, 10G, and 10B by their light emission. The emission 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 an end of the first electrode 2, an organic compound layer 4 covering the first electrode 2 and the insulating layer 3, a transparent electrode which is a second electrode 5, a protective layer 6, and a color filter 7.

[0176] A transistor and a capacitor element may be arranged in the lower layer 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).

[0177] The insulating layer 3 is also called a bank or a pixel isolation film. It covers an end of the first electrode 2 and is arranged surrounding the first electrode 2. A portion where the insulating layer 3 is not arranged is in contact with the organic compound layer 4 and becomes a light-emitting region.

[0178] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transmissive electrode.

[0179] The protective layer 6 reduces the penetration of moisture into the organic compound layer 4. The protective layer 6 is shown as a single layer, but may be a plurality of layers. There may be an inorganic compound layer and an organic compound layer for each layer.

[0180] The color filter 7 is divided into 7R, 7G, and 7B according to its color. The color filter 7 may be formed on a planarization film (not shown). Further, it may have a resin protective layer (not shown) on the color filter 7. Also, the color filter 7 may be formed on the protective layer 6. Or it may be bonded after being provided on a counter substrate such as a glass substrate.

[0181] The display device in Fig. 1(b) includes an organic light-emitting element 26 and a TFT 18 which is an example of a transistor. A substrate 11 such as glass or silicon has an insulating layer 12 provided thereon. Active elements such as the TFT 18 are arranged on the insulating layer 12, and a gate electrode 13, a gate insulating film 14, and a semiconductor layer 15 of the active element are provided. The TFT 18 has a drain electrode 16 and a source electrode 17. An insulating film 19 is provided on the TFT 18. The anode 21 constituting the organic light-emitting element 26 and the source electrode 17 are connected via a contact hole 20.

[0182] Note that the electrical connection method between the electrodes (anode 21, cathode 23) included in the organic light-emitting element 26 and the electrodes (source electrode 17, drain electrode 16) included in the TFT 18 is not limited to the mode shown in Fig. 1(b). That is, any one of the anode 21 or the cathode 23 and any one of the source electrode 17 or the drain electrode 16 of the TFT 18 may be electrically connected.

[0183] In the display device of Fig. 1(b), the organic compound layer 22 is illustrated as one layer, but the organic compound layer 22 may be a plurality of layers. A first protective layer 24 and a second protective layer 25 for reducing the deterioration of the organic light-emitting element 26 are provided on the cathode 23.

[0184] In the display device of Fig. 1(b), a transistor is used as a switching element, but other switching elements such as a MIM element may be used instead.

[0185] Also, the transistor used in the display device 100 of Fig. 1(b) is not limited to a thin-film transistor having an active layer on an insulating surface of a substrate, and a transistor using a single-crystalline silicon wafer may also be used. Examples of the active layer include non-single-crystalline silicon such as single-crystalline silicon, amorphous silicon, and microcrystalline silicon, and non-single-crystalline oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Note that a thin-film transistor is also called a TFT element.

[0186] The transistor included in the display device of FIG. 1(b) may be formed within a substrate such as a Si substrate. Here, forming within the substrate means fabricating the transistor by processing the substrate itself such as a Si substrate. That is, having a transistor within the substrate can also be regarded as the substrate and the transistor being integrally formed.

[0187] The organic light-emitting element according to the present embodiment has its emission luminance controlled by a TFT which is an example of a switching element, and an image can be displayed by the respective emission luminances by providing a plurality of organic light-emitting elements in a plane. Note that the switching element according to the present 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" can also mean within the substrate. Whether to provide a transistor within the substrate or use a TFT is selected according to the size of the display portion. For example, if the size is about 0.5 inches, it is preferable to provide the organic light-emitting element on the Si substrate.

[0188] FIG. 2 is a schematic diagram showing an example of the display device according to the present embodiment. The display device 1000 may include a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008 between an upper cover 1001 and a lower cover 1009. The touch panel 1003 and the display panel 1005 are connected to flexible printed circuits FPC 1002 and 1004. 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, or may be provided at another position even if it is a portable device.

[0189] The display device according to the present embodiment may have a color filter having red, green, and blue. The red, green, and blue of the color filter may be arranged in a delta array.

[0190] The display device according to this embodiment may be used for the display unit of a mobile terminal. In that case, it may have both a display function and an operation function. Examples of the mobile terminal include mobile phones such as smartphones, tablets, head-mounted displays, and the like.

[0191] The display device according to this embodiment may be used for the 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. Further, the display unit may be a display unit exposed to the outside of the imaging device or a display unit disposed within the viewfinder. The imaging device may be a digital camera or a digital video camera.

[0192] FIG. 3(a) is a schematic diagram showing an example of the 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 the display device according to this embodiment. In that case, the display device may display not only the image to be captured but also environmental information, imaging instructions, and the like. The environmental information may include the intensity of external light, the direction of external light, the speed at which the subject moves, the possibility that the subject is shielded by an obstacle, and the like. Since the timing suitable for imaging is a very short time, it is better to display information as soon as possible. Therefore, it is preferable to use the display device using the organic light-emitting element of the present invention. This is because the organic light-emitting element has a fast response speed. The display device using the organic light-emitting element can be used more preferably than a liquid crystal display device.

[0193] The imaging device 1100 has an optical unit (not shown). The optical unit has a plurality of lenses and forms an image on an imaging element housed in the housing 1104. The plurality of lenses can adjust the focus by adjusting their relative positions. This operation can also be performed automatically. The imaging device may be called an optoelectronic conversion device. The optoelectronic conversion device may include, as imaging methods, a method of detecting the difference from a previous image instead of sequentially imaging, a method of cutting out from an image that is always recorded, and the like.

[0194] FIG. 3(b) is a schematic diagram showing an example of an electronic device according to the present embodiment. The electronic device 1200 includes a display unit 1201, an operation unit 1202, and a housing 1203. The housing 1203 may include a circuit, a printed circuit board having the circuit, a battery, and a communication unit. The operation unit 1202 may be a button or a reaction unit of a touch panel method. The operation unit 1202 may be a biometric recognition unit that recognizes a fingerprint and performs unlocking or the like. An electronic device having a communication unit can also be called a communication device. The electronic device 1200 may further have a camera function by including a lens and an imaging device. An image captured by the camera function is displayed on the display unit 1201. Examples of the electronic device 1200 include a smartphone and a notebook computer.

[0195] FIG. 4 is a schematic diagram showing an example of a display device according to the present embodiment. FIG. 4(a) shows a display device such as a TV monitor or a PC monitor. The display device 1300 has a frame 1301 and a display unit 1302. The organic light-emitting element of the present invention is used for the display unit 1302. The display device 1300 has a frame 1301 and a base 1303 that supports the display unit 1302. The base 1303 is not limited to the form of FIG. 4(a). The lower side of the frame 1301 may also serve as the base. Further, the frame 1301 and the display unit 1302 may be curved. The radius of curvature may be 5000 mm or more and 6000 mm or less.

[0196] Figure 4(b) is a schematic diagram showing another example of the display device according to the present embodiment. The display device 1310 in Figure 4(b) is configured to be foldable and is a so-called foldable display device. The display device 1310 includes a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 have the organic light-emitting element of the present invention. The first display unit 1311 and the second display unit 1312 may be a single seamless display device. The first display unit 1311 and the second display unit 1312 can be separated at the bending point. The first display unit 1311 and the second display unit 1312 may display different images respectively, or may display a single image together with the first and second display units.

[0197] Figure 5(a) is a schematic diagram showing an example of the lighting device according to the present embodiment. The lighting device 1400 may include a housing 1401, a light source 1402, a circuit board 1403, an optical filter 1404 that transmits the light emitted by the light source 1402, and a light diffusing portion 1405. The light source 1402 has the organic light-emitting element of the present invention. The optical filter 1404 may be a filter that improves the color rendering property of the light source. The light diffusing portion 1405 can effectively diffuse the light of the light source, such as lighting up, and deliver the light to a wide range. The optical filter 1404 and the light diffusing portion 1405 may be provided on the light-emitting side of the lighting. If necessary, a cover may be provided on the outermost part.

[0198] The lighting device is, for example, a device for lighting a room. The lighting device may emit any color from white, day white, or other colors from blue to red. It may have a dimming circuit for dimming them or a color mixing circuit for mixing the emission colors. The lighting device has the organic light-emitting element of the present invention and a power supply circuit connected thereto. The power supply circuit is a circuit that converts an AC voltage into a DC voltage. Also, white has a color temperature of 4200K and day white has a color temperature of 5000K. The lighting device may have a color filter. In addition, the lighting device according to the present embodiment may have a heat radiating portion. The heat radiating portion releases the heat inside the device to the outside of the device, and examples thereof include metals with high specific heat and liquid silicone.

[0199] FIG. 5(b) is a schematic diagram of an automobile which is an example of a moving body according to the present embodiment. The automobile has a tail lamp which is an example of a lighting device. The automobile 1500 may have a tail lamp 1501 and may be configured to turn on the tail lamp when a braking operation or the like is performed.

[0200] The tail lamp 1501 may have the organic light emitting element of the present invention. The tail lamp 1501 may have a protective member for protecting the organic light emitting element. The protective member has a certain degree of high strength and may be made of any material as long as it is transparent, but is preferably made of polycarbonate or the like. A phthalic acid derivative, an acrylonitrile derivative or the like may be mixed with the polycarbonate.

[0201] The automobile 1500 may have a vehicle body 1503 and a window 1502 attached thereto. The window 1502 may be a transparent display as long as it is not a window for checking the front and rear of the automobile. The transparent display has the organic light emitting element of the present invention. In this case, the constituent materials such as the electrodes of the organic light emitting element are made of transparent members.

[0202] 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 fuselage and a lighting device provided on the fuselage. The lighting device may emit light for notifying the position of the fuselage. The lighting device has the organic light emitting element of the present invention.

[0203] With reference to FIG. 6, application examples of the display device of each of the above embodiments will be described. The display device can be applied to a system wearable as a wearable device such as smart glasses, an HMD, or smart contacts. The imaging display device used in such an application example has an imaging device capable of photoelectrically converting visible light and a display device capable of emitting visible light.

[0204] FIG. 6(a) is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention. Using FIG. 6(a), glasses 1600 (smart glasses) according to one application example will be described. An imaging device 1602 such as a CMOS sensor or a SPAD is provided on the front surface side of the lens 1601 of the glasses 1600. Also, a display device of each of the above-described embodiments is provided on the back surface side of the lens 1601.

[0205] The glasses 1600 further include a control device 1603. The control device 1603 functions as a power source that supplies power to the imaging device 1602 and the display device. Also, the control device 1603 controls the operations of the imaging device 1602 and the display device. An optical system for condensing light onto the imaging device 1602 is formed in the lens 1601.

[0206] FIG. 6(b) is a schematic diagram showing another example of a wearable device according to an embodiment of the present invention. Using FIG. 6(b), glasses 1610 (smart glasses) according to one application example will be described. The glasses 1610 have a control device 1612, and an imaging device corresponding to the imaging device 1602 in FIG. 6(a) and a display device are mounted on the control device 1612. An optical system for projecting light emitted from the imaging device and the display device is formed in the lens 1611, and an image is projected onto the lens 1611. The control device 1612 functions as a power source that supplies power to the imaging device and the display device, and controls the operations of the imaging device and the display device.

[0207] The control device 1612 may have a gaze detection unit that detects the wearer's gaze. The detection of the gaze may use infrared rays. The infrared light emitting unit emits infrared light toward the eyes of the user who is gazing at the display image. By detecting the reflected light of the emitted infrared light from the eyes with an imaging unit having a light receiving element, an imaging image of the eyes can be obtained. By having a reducing means for reducing the light from the infrared light emitting unit to the display unit in a plan view, a decrease in image quality is reduced. The gaze of the user with respect to the display image is detected from the imaging image of the eyes obtained by imaging the infrared light. Any known method can be applied to the gaze detection using the imaging image of the eyes. As an example, a gaze detection method based on the Purkinje image by the reflection of the irradiation light on the cornea can be used. More specifically, gaze detection processing based on the corneal reflection method is performed. Using the corneal reflection method, a gaze vector representing the orientation (rotation angle) of the eyes is calculated based on the image of the pupil and the Purkinje image included in the imaging image of the eyes, whereby the gaze of the user is detected.

[0208] The display device according to an embodiment of the present invention has an imaging device having a light receiving element, and may control the display image of the display device based on the gaze information of the user from the imaging device. Specifically, the display device determines a first visual field region that the user gazes at and a second visual field region other than the first visual field region based on the gaze information. The first visual field region and the second visual field region may be determined by the control device of the display device, or may receive those determined by an external control device. In the display area of the display device, the display resolution of the first visual field region may be controlled to be higher than the display resolution of the second visual field region. That is, the resolution of the second visual field region may be made lower than that of the first visual field region.

[0209] In addition, the display area has a first display area and a second display area different from the first display area, and based on the line-of-sight information, an area with a higher priority is determined from the first display area and the second display area. The first field of view area and the second field of view area may be determined by the control device of the display device, or may be received from an external control device. The resolution of the area with a higher priority may be controlled to be higher than the resolution of the areas other than the area with a higher priority. That is, the resolution of the area with a relatively lower priority may be lowered.

[0210] In addition, AI may be used to determine the first field of view area or the area with a higher priority. AI may be a model configured to estimate the angle of the line of sight and the distance to the target at the tip of the line of sight from the image of the eyeball using the image of the eyeball and the direction in which the eyeball of the image is actually looking as teacher data. The AI program may be possessed by the display device, the imaging device, or an external device. When an external device has it, it is transmitted to the display device via communication.

[0211] When performing display control based on visual recognition detection, it can be preferably applied to smart glasses further having an imaging device for imaging the outside. The smart glasses can display the captured external information in real time.

[0212] FIG. 7(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 has a photoreceptor 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transferrer 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 photoreceptor 27. This exposure light source 28 has the organic light emitting element of the present invention. The developing unit 31 has toner and the like. The charging unit 30 charges the photoreceptor 27. The transferrer 32 transfers the developed image to the 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.

[0213] Figures 7(b) and 7(c) are diagrams showing the exposure light source 28, and are schematic diagrams showing a state in which a plurality of light emitting portions 36 are arranged on a long substrate. Arrow 37 is a direction parallel to the axis of the photoreceptor, and represents the column direction in which the organic light emitting elements are arranged. This column direction is the same as the direction of the axis around which the photoreceptor 27 rotates. This direction can also be called the major axis direction of the photoreceptor 27. Figure 7(b) shows a form in which the light emitting portion 36 is arranged along the major axis direction of the photoreceptor 27. Figure 7(c) shows a form different from that of Figure 7(b), in which the light emitting portions 36 are alternately arranged in the column direction in each of the first column and the second column. The first column and the second column are arranged at different positions in the row direction. In the first column, a plurality of light emitting portions 36 are arranged at intervals. The second column has light emitting portions 36 at positions corresponding to the intervals between the light emitting portions 36 in the first column. That is, also in the row direction, a plurality of light emitting portions 36 are arranged at intervals. The arrangement in Figure 7(c) can also be described as, for example, a state of being arranged in a grid pattern, a state of being arranged in a staggered grid, or a checkered pattern. As described above, by using the device using the organic light emitting element according to the present embodiment, it is possible to obtain a good image quality and a stable display even for a long-time display.

[0214] 〔Included configurations〕 The disclosure of the present embodiment includes the following configurations. (Configuration 1) An organic compound characterized by being represented by the following general formula [1]. Ir(L1)(L2)2[1] 〔In the above general formula [1], the partial structure Ir(L1) is represented by the following general formula [1-1], and the partial structure Ir(L2)2 is represented by the following general formula [1-2], respectively.

[0215]

Chemical formula

[0216]

Chemical formula

[0217] In the above general formula [1-1], ring A is selected from substituted or unsubstituted condensed rings of three or more rings. R1 to R in the above general formula [1-1] 10 , and R in the above general formula [1-2] 11 to R 18 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 aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, and a cyano group. R1 to R 10 , and R 11 to R 18 may be such that adjacent Rs are bonded to each other to form a ring. The two ligands L2 may have different structures from each other. ]

[0218] (Configuration 2) The ring A is selected from a substituted or unsubstituted fluorene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted dibenzothiophene ring, and a substituted or unsubstituted carbazole ring. The organic compound according to Configuration 1, characterized in that. (Configuration 3) At least one of the above R1 to R 10 is selected from a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, and a cyano group. The organic compound according to Configuration 1 or 2, characterized in that. (Configuration 4) At least one of the above R 11 to R 18 is selected from a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, and a cyano group. The organic compound according to any one of Configurations 1 to 3, characterized in that.

[0219] (Configuration 5) An organic light-emitting device having a pair of electrodes and an organic compound layer disposed between the pair of electrodes, wherein the organic compound layer has an organic compound according to any one of Configurations 1 to 4. (Configuration 6) The organic compound layer has a light-emitting layer, and the light-emitting layer contains an organic compound according to any one of Configurations 1 to 4. The organic light-emitting device according to Configuration 5. (Configuration 7) The light-emitting layer contains an organic compound according to any one of Configurations 1 to 4 as a first organic compound and further contains a second organic compound. The organic light-emitting device according to Configuration 6. (Configuration 8) The second organic compound has at least one condensed ring selected from the group consisting of a triphenylene ring, a dibenzothiophene skeleton, and a carbazole skeleton. The organic light-emitting device according to Configuration 7. (Configuration 9) The organic light-emitting device according to any one of Configurations 6 to 8, further having another light-emitting layer disposed in a stacked manner with the light-emitting layer, and the other light-emitting layer emits light of a color different from the light-emitting color of the light-emitting layer. (Configuration 10) The organic light-emitting device according to Configuration 9, which emits white light.

[0220] (Configuration 11) A display device having a plurality of pixels, wherein at least one of the plurality of pixels has an organic light-emitting device according to any one of Configurations 5 to 10 and a transistor connected to the organic light-emitting device. (Configuration 12) An optoelectronic conversion device having 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, wherein the display unit has an organic light-emitting device according to any one of Configurations 5 to 10. (Configuration 13) An electronic device comprising: a display unit having an organic light-emitting element according to any one of Configurations 5 to 10; a housing provided with the display unit; and a communication unit provided in the housing and communicating with the outside. (Configuration 14) An illumination device comprising: a light source having an organic light-emitting element according to any one of Configurations 5 to 10; and a light diffusing unit or an optical filter that transmits light emitted from the light source. (Configuration 15) A moving body comprising: a lighting fixture having an organic light-emitting element according to any one of Configurations 5 to 10; and a body provided with the lighting fixture. (Configuration 16) An exposure light source of an electrophotographic image forming apparatus, characterized by having an organic light-emitting element according to any one of Configurations 5 to 10.

Example

[0221] Hereinafter, the present invention will be described by way of examples. Note that the present invention is not limited to these examples.

[0222] (Example 1) The exemplary compound A-1 and the comparative compounds 3 and 4 described in Table 1 above were synthesized according to the following reaction formula.

[0223]

Chemical formula

[0224] In the above reaction formula, Int-1 was synthesized according to (Synthesis of Intermediate 1-4) in JP-A-2014-141425, and Int-3 was synthesized according to (Example 1) in JP-T-2012-502046.

[0225] [Reaction Step 1 (Ligand L1: Synthesis of Intermediate Compound Int-2)] The following reagents and solvents were placed in a 50 mL eggplant flask. Int-1: 1.00 g (3.79 mmol) 2-(9,9-Dimethyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (manufactured by Tokyo Chemical Industry Co., Ltd.): 1.46 g (4.55 mmol) Sodium carbonate: 1.21 g (11.4 mmol) Tetrakis(triphenylphosphine)palladium(0): 0.219 g (0.190 mmol) Toluene: 10 mL Ion-exchanged water: 6 mL

[0226] The above reaction solution was heated to reflux with stirring for 18 hours under nitrogen. After completion of the reaction, it was cooled to room temperature, and the precipitated solid was collected by filtration. The obtained solid was purified by a silica gel column (chloroform:heptane = 3:1). The obtained white powder was dried in a vacuum dryer at 80 °C for 12 hours to obtain 1.34 g of Int-2 (yield 84%).

[0227] [Reaction Step 2 (Synthesis of Exemplary Compound A-1, Comparative Compound 3, and Comparative Compound 4)] The following reagents and solvents were charged into a 200 mL eggplant flask. Int-2: 1.30 g (3.08 mmol) Int-3: 1.10 g (1.54 mmol) Ethylene glycol: 8 mL Diethylene glycol dimethyl ether: 8 mL

[0228] The above reaction solution was heated to reflux with stirring for 3 hours under nitrogen. After completion of the reaction, it was cooled to room temperature, and the precipitated solid was collected by filtration. The obtained solid was purified by a silica gel column (toluene:heptane = 3:1), and a plurality of components were isolated and dried in a vacuum dryer at 80 °C for 12 hours. Next, analysis was performed by MALDI-TOF MS (matrix-assisted ionization-time of flight mass spectrometry) to identify each component. As a result, 0.440 g of Exemplary Compound A-1 (M + : 921.3, yield 31%), 0.256 g of Comparative Compound 3 (M + : 1187.4, yield 14%), and 0.112 g of Comparative Compound 4 (M +: 1453.5, yield 5.0%) was obtained.

[0229] (Examples 2 to 8) Exemplary compounds B-2, C-7, D-3, D-4, D-5, D-7, and D-8 were synthesized.

[0230] [Reaction Step 1 (Ligand L1: Synthesis of Intermediate Compounds Int-4 to 10)] In Reaction Step 1 of Example 1, Int-1 and 2-(9,9-dimethyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane were changed to the naphtho[2,1-f]isoquinoline derivatives and boronic acid compounds or boronic acid ester compounds shown in Table 4, and Ligand L1 shown in Table 4 was synthesized in the same manner as Reaction Step 1 of Example 1, except for the change.

[0231] [Table 4]

[0232] Int-11 described in Table 4 was synthesized according to (Example 4) in JP-A-2014-141425. Also, Int-12 and 13 were synthesized in the same manner as the synthesis of Int-11, except that intermediate 4-3 (6-(tert-butyl)-2-naphthalenyl-1,1,1-trifluoromethanesulfonate) was changed to 6-bromo-2-naphthonitrile and 2-bromo-6-fluoronaphthalene, respectively.

[0233] [Reaction Step 2 (Synthesis of Exemplary Compounds)] In Reaction Step 2 of Example 1, Exemplary compounds shown in Tables 5 and 6 were synthesized in the same manner as Reaction Step 2 of Example 1, except that Int-2 and 3 were changed to Ligand L1 and triflate salts shown in Tables 5 and 6, respectively.

[0234] [Table 5]

[0235] [Table 6]

[0236] Int-14, 15, and 16 described in Tables 5 and 6 were synthesized in the same manner as in (Example 1: Synthesis of PPY Dimer) of JP-T-2012-502046, except that 2-phenylpyridine was changed to 4-(tert-butyl)-2-phenylpyridine, 4-(tert-butyl)-2-(3-(tert-butyl)phenyl)pyridine, and 4-(tert-butyl)-2-(4-(tert-butyl)phenyl)pyridine, respectively.

[0237] (Comparative Examples 1 and 2) The comparative compounds 1 and 2 described in Table 1 above were synthesized according to (Synthesis Examples 18 and 17) in JP-A-2014-127687, respectively.

[0238] (Comparative Examples 3 and 4) The comparative compounds 5 and 6 described in Table 2 above were synthesized. In Reaction Step 1 of Example 1, the comparative compounds 5 and 6 were synthesized in the same manner as Reaction Steps 1 and 2 of Example 1, except that 2-(9,9-dimethyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was changed to phenylboronic acid or 2-naphthaleneboronic acid.

[0239] (Comparative Example 5) The comparative compound 7 described in Table 2 above was synthesized according to (Example 5) in JP-A-2014-141425.

[0240] (Example 9) An organic light-emitting device having a bottom emission structure in which an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode were sequentially formed on a substrate was fabricated. First, an ITO film was formed on a glass substrate, and an ITO electrode (anode) was formed by performing a desired patterning process. At this time, the film thickness of the ITO electrode was set to 100 nm. The substrate on which the ITO electrode was thus formed was used as an ITO substrate in the following steps. Next, vacuum evaporation by resistance heating was performed in a vacuum chamber of 1.33×10 -4 Pa, and an organic compound layer and an electrode layer shown in Table 7 were continuously formed on the ITO substrate. At this time, the electrode area of the opposing electrode (metal electrode layer, cathode) was set to 3 mm 2 .

[0241] [Table 7]

[0242] The characteristics of the obtained device were measured and evaluated. The chromaticity coordinates calculated from the spectrum of the light-emitting device were (0.683, 0.315), and since the X value was higher and the Y value was lower than those of red (0.670, 0.330) of the NTSC standard, it can be said that the color purity was high.

[0243] Furthermore, a continuous drive test was performed at a current density of 100 mA / cm 2 , and the time when the luminance degradation rate reached 5% was measured. When the time when the luminance degradation rate of the device of Comparative Example 7 described later reached 5% was taken as the reference (1.0), the 5% luminance degradation time of this Example was expressed as a ratio and was 2.2. In this Example, specifically, the current-voltage characteristics were measured with a microammeter 4140B manufactured by Hewlett-Packard Company, and the emission luminance was measured with BM7 manufactured by Topcon Corporation.

[0244] (Examples 10 to 17, Comparative Examples 6, 7) An organic light-emitting device was fabricated in the same manner as in Example 9 except that the host and guest were appropriately changed to the compounds shown in Table 8. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 9. The measurement results are shown in Table 8. As an evaluation of color purity, an element that satisfied an X value higher and a Y value lower than those of red (0.670, 0.330) of the NTSC standard was marked with ○, and an element that did not satisfy was marked with ×.

[0245]

Table 8

[0246] (Example 18) An organic light-emitting device was fabricated in the same manner as in Example 9, except that the organic compound layer and the electrode layer shown in Table 9 were continuously formed.

[0247]

Table 9

[0248] For the obtained device, the characteristics of the device were measured and evaluated in the same manner as in Example 9. The chromaticity coordinates calculated from the spectrum of the light-emitting device were (0.682, 0.316), which had a higher X value and a lower Y value than those of red in the NTSC standard (0.670, 0.330), indicating high color purity. Furthermore, a continuous driving test was conducted at a current density of 100 mA / cm 2 and the time when the luminance degradation rate reached 5% was measured. When the time when the luminance degradation rate of Comparative Example 9 described later reached 5% was taken as the reference (1.0), the 5% luminance degradation time of this example was expressed as a ratio and was 2.6.

[0249] (Examples 19 to 28, Comparative Examples 8, 9) An organic light-emitting device was fabricated in the same manner as in Example 18, except that the compound shown in Table 10 was appropriately changed. For the obtained device, the characteristics of the device were measured and evaluated in the same manner as in Example 18. The measurement results are shown in Table 10.

[0250]

Table 10

[0251] As shown in Tables 8 and 10, by using the organic compound of the present invention as a light-emitting material in the light-emitting layer, an organic light-emitting device excellent in color purity and durability characteristics can be provided. Further, as shown in Table 10, by using a material having a triphenylene ring, a dibenzothiophene skeleton, and a carbazole skeleton as a host material, the lifetime characteristics of the device are improved.

Explanation of Reference Numerals

[0252] 2,21: First electrode, 8,26: Organic light-emitting device, 5,23: Second electrode, 18: Transistor, 27: Photoconductor, 28: Exposure light source, 1200: Electronic device, 1201, 1302, 1311, 1312: Display unit, 1203: Housing, 1300, 1310: Display device, 1400: Lighting device, 1402: Light source, 1404: Optical filter, 1405: Light diffusion unit

Claims

1. An organic compound characterized by being represented by the following general formula [1]. Ir(L 1 )(L 2 ) 2 [1] [In the above general formula [1], the partial structure Ir(L 1 ) is represented by the following general formula [1-1], and the partial structure Ir(L 2 ) 2 is represented by the following general formula [1-2], respectively. 【Chemical formula 1】 【Chemical formula 2】 In the above general formula [1-1], ring A is selected from substituted or unsubstituted condensed rings of three or more rings, R 1 to R 10 in the above general formula [1-1], and R 11 to R 18 in the above general formula [1-2] 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 aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, and a cyano group. R 1 to R 10 , and R 11 to R 18 may be such that adjacent Rs are bonded to each other to form a ring, The two ligands L 2 may have different structures from each other. ]

2. The organic compound according to claim 1, wherein the ring A is selected from a substituted or unsubstituted fluorene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted dibenzothiophene ring, and a substituted or unsubstituted carbazole ring.

3. The above R 1 to R 10At least one of them is selected from a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, and a cyano group. The organic compound according to claim 1.

4. Said R 11 to R 18 At least one of them is selected from a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, and a cyano group. The organic compound according to claim 1.

5. An organic light-emitting device having a pair of electrodes and an organic compound layer disposed between the pair of electrodes, wherein the organic compound layer has the organic compound according to claim 1. The organic light-emitting device.

6. The organic compound layer has a light-emitting layer, wherein the light-emitting layer contains the organic compound according to claim 1. The organic light-emitting device according to claim 5.

7. The light-emitting layer contains the organic compound according to claim 1 as a first organic compound and further contains a second organic compound. The organic light-emitting device according to claim 6.

8. The second organic compound has at least one condensed ring of a triphenylene ring, a dibenzothiophene skeleton, or a carbazole skeleton. The organic light-emitting device according to claim 7.

9. The organic light-emitting device according to claim 6, further having another light-emitting layer disposed in a stacked manner with the light-emitting layer, and the other light-emitting layer emits light of a color different from the light-emitting color of the light-emitting layer.

10. The organic light-emitting device according to claim 9, which emits white light.

11. A display device having a plurality of pixels, wherein at least one of the plurality of pixels has the organic light-emitting element according to claim 5 and a transistor connected to the organic light-emitting element.

12. An optoelectronic conversion device having an optical unit having a plurality of lenses, an imaging element that receives light that has passed through the optical unit, and a display unit that displays an image captured by the imaging element. The display unit has the organic light-emitting element according to claim 5.

13. An electronic device having a display unit having the organic light-emitting element according to claim 5, a housing in which the display unit is provided, and a communication unit provided in the housing and communicating with the outside.

14. An illumination device having a light source having the organic light-emitting element according to claim 5 and a light diffusing unit or an optical filter that transmits light emitted by the light source.

15. A moving body having a lighting fixture having the organic light-emitting element according to claim 5 and a body in which the lighting fixture is provided.

16. An exposure light source of an electrophotographic image forming apparatus, characterized by having the organic light-emitting element according to claim 5.

Images