Organic compound

Abstract

To provide a novel organic metal complex.SOLUTION: An organic metal complex is an Ir complex having a structure represented by general formula (G-1) that includes a 1H-naphtho[1,2-d]imidazole skeleton as a ligand. Among the N in the 1H-naphtho[1,2-d]imidazole skeleton, the N that is not bonded to Ir is bonded to a substituted or unsubstituted aryl group. In general formula (G-1), R1 to R10 each independently represent a hydrogen, a C1-6 alkyl group, a substituted or unsubstituted C3-7 cycloalkyl group, a substituted or unsubstituted C6-25 aryl group, or an electron withdrawing group, and Ar represents a substituted or unsubstituted C6-25 aryl group.SELECTED DRAWING: Figure 1

Description

Technical Field

[0001] One aspect of the present invention relates to novel organic compounds. In particular, it relates to an organometallic complex containing a 1H-naphtho[1,2-d imidazole skeleton in the ligand. Or, it relates to a light-emitting element, a light-emitting device, an electronic device, and a lighting device containing the organometallic complex.

[0002] Note that one aspect of the present invention is not limited to the above technical field. One aspect of the present invention relates to an article, a method, or a manufacturing method. In particular, one aspect of the present invention relates to an organic compound, a light-emitting element, a light-emitting device a lighting device, and a manufacturing method thereof. Also, one aspect of the present invention relates to a novel synthesis method of an organometallic complex containing a 1H-naph tho[1,2-d]imidazole skeleton in the ligand. Therefore, more specifically, as one aspect of the present invention disclosed in this specification, there is a method for manufacturing a light-emitting element, a light-emitting device, a display device, an electronic device, and a lighting device containing the organometallic complex, which can be cited as an example.

Background Art

[0003] The practical application of light-emitting elements (organic EL elements) using electroluminescence (EL) of organic compounds is progressing. The basic configuration of these light-emitting elements is that an organic compound layer (EL layer) containing a light-emitting material is sandwiched between a pair of electrodes. By applying a voltage to this element to inject carriers and utilizing the recombination energy of the carriers, light emission from the light-emitting material can be obtained.

[0004] Since such light-emitting elements are self-luminous, when used as pixels of a display, they have advantages such as high visibility and no need for a backlight, and are flat panel display elements. ​​​​​​​​​ is suitable as. In addition, a display using such a light-emitting element can be manufactured to be thin and lightweight. This is also a great advantage. Moreover, it is also characterized by a very fast response speed.

[0005] In addition, since these light-emitting elements can form a light-emitting layer continuously in two dimensions, light emission in a planar shape can be obtained. This is a characteristic that is difficult to obtain with point light sources typified by incandescent bulbs and LEDs, or linear light sources typified by fluorescent lamps. Also, since light emission from organic compounds can be made to emit light without including ultraviolet light by selecting materials, it has high utility value as a surface light source that can be applied to lighting and the like.

[0006] As described above, displays and lighting devices using organic EL elements are suitable for various electronic devices. Therefore, research and development are being advanced to obtain light-emitting elements with better efficiency and device lifetime. In recent years, since phosphorescent light-emitting elements can obtain higher light-emitting efficiency than fluorescent light-emitting elements, the development of phosphorescent materials has been actively carried out (see, for example, Patent Document 1).

Prior Art Documents

Patent Documents

[0007]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0008] Although the development of phosphorescent materials showing excellent characteristics as reported in the above-mentioned Patent Document 1 is progressing, the development of new materials showing even better characteristics is desired. In particular, high efficiency and high It is desirable to develop reliable blue and green phosphorescent materials.

[0009] In view of the above, an object of one embodiment of the present invention is to provide a novel organometallic complex. In one aspect of the present invention, a novel 1H-naphtho[1,2-d]imidazole skeleton-containing compound is provided. Another object of the present invention is to provide an organic metal complex having a high quantum yield. Another object of the present invention is to provide an organometallic complex having high emission efficiency. Another object of the present invention is to provide a light-emitting element having a long lifetime. Another object of the present invention is to provide a light-emitting element having good color purity. Another object of the present invention is to provide an optical element that emits light with a low driving voltage. The object is to provide an element.

[0010] In another embodiment of the present invention, a light-emitting element, a light-emitting device, and an electronic device each having high reliability are provided. Another object of the present invention is to provide a light-emitting element with low power consumption. It is an object of the present invention to provide a light emitting device, a light emitting device, and an electronic device.

[0011] The description of these problems does not preclude the existence of other problems. The embodiment does not necessarily have to solve all of these problems. The above will become apparent from the description in the specification, drawings, claims, etc. It is possible to extract other issues from the descriptions in the patent, claims, etc. [Means for solving the problem]

[0012] One aspect of the present invention is a ligand having a 1H-naphtho[1,2-d]imidazole skeleton, It is an organometallic complex having a structure represented by the general formula (G-1).

[0013]

Chem.

[0014] In the general formula (G-1), R 1 to R 10 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or an electron-withdrawing group, and Ar represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. group, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted carbon number of 6 to 25 aryl groups or electron-withdrawing groups, and Ar represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

[0015] Also, another aspect of the present invention is an organometallic complex having a structure represented by the following general formula (G-2). body.

[0016]

Chem.

[0017] In the general formula (G-2), R 1 to R 15 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted carbon number of 6 to 25 aryl groups or electron-withdrawing groups, and Ar represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

[0018] Also, another aspect of the present invention is an organometallic complex having a structure represented by the following general formula (G-3). body.

[0019]

Chem.

[0020] In the general formula (G-3), R 11 , R13 and R 15 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms , a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or an electron-withdrawing group.

[0021] In another aspect of the present invention, there is an organometallic complex having a structure represented by the following general formula (G-4).

[0022]

Chemical formula

[0023] In general formula (G-4), R 13 represents hydrogen or an electron-withdrawing group.

[0024] In another aspect of the present invention, there is an organometallic complex having a structure represented by the following general formula (G-5).

[0025]

Chemical formula

[0026] In general formula (G-5), R 15 represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms .

[0027] In the above configuration, it is preferable that general formula (G-1) is represented by general formula (G-6).

[0028]

Chemical formula

[0029] ​​In the above structure, it is preferable that general formula (G-2) is represented by general formula (G-7).

[0030]

Chem.

[0031] In the above structure, it is preferable that general formula (G-3) is represented by general formula (G-8).

[0032]

Chem.

[0033] In the above structure, it is preferable that general formula (G-4) is represented by general formula (G-9).

[0034]

Chem.

[0035] In the above structure, it is preferable that general formula (G-5) is represented by general formula (G-10).

[0036]

Chem.

[0037] In the above structure, it is preferable that general formula (G-1) is represented by general formula (G-11).

[0038]

Chem.

[0039] In general formula (G-11), L represents a monoanionic ligand, and n represents 1 or 2.

[0040] In the above structure, it is preferable that general formula (G-2) is represented by general formula (G-12).

[0041]

Chem.

[0042] In general formula (G-12), L represents a monoanionic ligand, and n represents 1 or 2.

[0043] In the above configuration, it is preferable that general formula (G-3) is represented by general formula (G-13).

[0044]

Chem.

[0045] In general formula (G-13), L represents a monoanionic ligand, and n represents 1 or 2.

[0046] In the above configuration, it is preferable that general formula (G-4) is represented by general formula (G-14).

[0047]

Chem.

[0048] In general formula (G-14), L represents a monoanionic ligand, and n represents 1 or 2.

[0049] In the above configuration, it is preferable that general formula (G-5) is represented by general formula (G-15).

[0050]

Chem.

[0051] In general formula (G-15), L represents a monoanionic ligand, and n represents 1 or 2.

[0052] In general formulas (G-3), (G-8) and (G-13), R 11 and R 15each is independently a hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cyclo alkyl group having 3 to 7 carbon atoms, and R 13 is preferably hydrogen or an electron-withdrawing group.

[0053] Further, in the above configuration, it is preferable that the electron-withdrawing group is any one of a halogeno group, a cyano group, and a trifluoromethyl group or the like.

[0054] Further, in the above configuration, it is preferable that the alkyl group is a branched-chain alkyl group having 3 to 6 carbon atoms or the like.

[0055] Further, in the above configuration, the monoanionic ligand is a monoanionic bidentate chelate ligand having a β-diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, a monoanionic bidentate chelate ligand having a phenolic hydroxyl group, or a monoanionic bidentate chelate ligand in which both of the two coordination elements are nitrogen, or a bidentate ligand that forms a metal-carbon bond with iridium by cyclometalation, and is preferably the like. Further, in the above configuration, the monoanionic ligand is preferably any one of the following general formulas (L1) to (L9 ). In the general formulas (L1) to (L9), R

[0056] to R

[0057]

Chemical formula

[0058] to R 21 to R 86 are each independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a halogeno group, a vinyl group, a cyano group, a substituted or or an unsubstituted haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, and represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. Further, A to A 1 to A 13 each independently represent nitrogen, or an sp hybridized carbon bonded to hydrogen, or an sp 2 hybridized carbon having a substituent. The substituent represents any one of an alkyl group having 1 to 6 carbon atoms, a halogeno group, a haloalkyl group having 1 to 6 carbon atoms, or a phenyl group. 2 Further, another aspect of the present invention is any one of the organic compounds represented by the following structural formulas (100) to (103).

[0059] Also, another aspect of the present invention is a light-emitting device having an EL layer between a pair of electrodes, the EL layer containing the organic compound described in each of the above configurations. The organic compound is preferably contained in the light-emitting layer in the EL layer.

[0060]

Chemical formula

[0061] In addition, the light-emitting device in each of the above configurations has an EL layer between an anode and a cathode. Further, the EL layer preferably has at least a light-emitting layer. Furthermore, the EL layer may include a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, or other functional layers.

[0062] Note that the light-emitting device in each of the above configurations has an EL layer between the anode and the cathode. Also, the EL layer preferably has at least a light-emitting layer. Further, the EL layer may include a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, or other functional layers.

[0063] In addition, another aspect of the present invention is a display device having at least one of the light-emitting device in each of the above configurations and a color filter or a transistor. Another aspect of the present invention is the above An electronic device having a display device and at least one of a housing or a touch sensor. Also Another aspect of the present invention is a lighting device having a light-emitting element of each of the above configurations and at least one of a housing or a touch sensor. Also, one aspect of the present invention includes not only a light-emitting device having a light-emitting element but also an electronic device having a light-emitting device within the scope. Therefore, the light-emitting device in this specification refers to an image display device or a light source (including a lighting device). Also, a display module in which a connector such as an FPC (Flexible Printed Circuit) or a TCP (Tape Carrier Package) is attached to a light-emitting element, a display module provided with a printed wiring board at the tip of the TCP, or a display module in which an IC (integrated circuit) is directly mounted on a light-emitting element by a COG ( Chip On Glass) method is also an aspect of the present invention.

Advantages of the Invention

[0064]

[0065] ​​​​​​​​​​​​​Alternatively, according to another aspect of the present invention, a highly reliable light-emitting element, a light-emitting device, and an electronic device can be provided. Alternatively, according to another aspect of the present invention, a light-emitting element, a light-emitting device, and an electronic device with low power consumption can be provided respectively. Alternatively, according to another aspect of the present invention, a light-emitting element, a light-emitting device, and an electronic device with low power consumption can be provided respectively. Note that the description of these effects does not prevent the existence of other effects. Note that one aspect of the present invention does not necessarily need to have all of these effects. Note that other effects can be clearly obtained from the descriptions in the specification, drawings, claims, etc., and it is possible to extract these other effects from the descriptions in the specification, drawings, claims, etc.

[0066] Note that the description of these effects does not prevent the existence of other effects. Note that one aspect of the present invention does not necessarily need to have all of these effects. Note that other effects can be clearly obtained from the descriptions in the specification, drawings, claims, etc., and it is possible to extract these other effects from the descriptions in the specification, drawings, claims, etc. Note that the description of these effects does not prevent the existence of other effects. Note that one aspect of the present invention does not necessarily need to have all of these effects. Note that other effects can be clearly obtained from the descriptions in the specification, drawings, claims, etc., and it is possible to extract these other effects from the descriptions in the specification, drawings, claims, etc. Note that the description of these effects does not prevent the existence of other effects. Note that one aspect of the present invention does not necessarily need to have all of these effects. Note that other effects can be clearly obtained from the descriptions in the specification, drawings, claims, etc., and it is possible to extract these other effects from the descriptions in the specification, drawings, claims, etc. Note that the description of these effects does not prevent the existence of other effects. Note that one aspect of the present invention does not necessarily need to have all of these effects. Note that other effects can be clearly obtained from the descriptions in the specification, drawings, claims, etc., and it is possible to extract these other effects from the descriptions in the specification, drawings, claims, etc.

BRIEF DESCRIPTION OF THE DRAWINGS

[0067]

Figure 1

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Figure 4

Figure 5

Figure 6

Figure 7

Figure 8

Figure 9

Figure 10

Figure 11

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Figure 19

Figure 20

Figure 21

Figure 22

Figure 23

Figure 24

Figure 25

Figure 26

Figure 27

Figure 28

Figure 29

Figure 30

Figure 31

Embodiments for Carrying Out the Invention

[0068] Hereinafter, embodiments of the present invention will be described. However, the present invention can be implemented in many different aspects, and it is easily understood by those skilled in the art that the form and details thereof can be variously changed without departing from the spirit and scope of the present invention. Therefore, the present invention should not be construed as being limited to the description contents of the present embodiment. It can be carried out, and it is easily understood by those skilled in the art that the form and details can be variously changed without departing from the spirit and scope of the present invention. Accordingly, it is not to be construed as being limited to the description contents of the present embodiment. Note that in each drawing described in this specification, the sizes and thicknesses of the anode, EL layer, intermediate layer, cathode, etc. may be exaggerated for clarity of explanation. Therefore, each component is not necessarily limited to its size, nor is it limited to the relative size between components.

[0069] In addition, in this specification and the like, ordinal numbers such as first, second, and third are used for convenience and do not indicate the order of steps or the vertical and horizontal positional relationships. Therefore, for example they are not limited to their sizes, nor are they limited to the relative sizes between components. Note that in each drawing described in this specification, the sizes and thicknesses of the anode, EL layer, intermediate layer, cathode, etc. may be exaggerated for clarity of explanation. Therefore, each component is not necessarily limited to its size, nor is it limited to the relative size between components.

[0070] Further, in this specification and the like, ordinal numbers such as first, second, and third are used for convenience and do not indicate the order of steps or the vertical and horizontal positional relationships. Therefore, for example they are not limited to their sizes, nor are they limited to the relative sizes between components. The term "first" can be appropriately replaced with "second", "third", etc. for explanation. In addition, the ordinal numbers described in this specification and the like may not match the ordinal numbers used to specify an aspect of the present invention.

[0071] In the configuration of the present invention described in this specification and the like, the same reference numerals are commonly used for the same parts or parts having similar functions among different drawings, and the repeated description thereof is omitted. In addition, when referring to parts having similar functions, the hatching patterns may be the same and may not be particularly labeled with reference numerals.

[0072] It should be noted that the terms "film" and "layer" may be interchangeable depending on the case or situation. For example, the term "conductive layer" may be changed to the term "conductive film". Or, for example, the term "insulating film" may be changed to the term "insulating layer".

[0073] (Embodiment 1) In this embodiment, an organometallic complex of an aspect of the present invention will be described below.

[0074] The organometallic complex of an aspect of the present invention has a structure represented by the following general formula (G-1).

[0075] [Chemical formula]

[0076] In the general formula (G-1), R 1 to R 10 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted carbon number of ​​​​​​represents an aryl group or an electron-withdrawing group having 6 to 25 carbon atoms, and Ar represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

[0077] The organometallic complex of one aspect of the present invention has a 1H-naphtho[1,2-d]imidazole skeleton in the ligand. By adopting such a configuration, when the organometallic complex is applied to a light-emitting device, a light-emitting device with good luminous efficiency and / or reliability can be obtained.

[0078] The ligand of the organometallic complex of one aspect of the present invention has a structure in which a benzene ring is further condensed to the benzene ring of the benzimidazole skeleton. By adopting such a structure, the stability of the molecule can be improved, and a light-emitting device with good reliability can be obtained. In addition, an organometallic complex with good photoluminescence quantum yield can be obtained.

[0079] Further, by bonding a substituted or unsubstituted aryl group having 6 to 25 carbon atoms to the 1-position of the 1H-naphtho[1,2-d]imidazole skeleton, the stability and sublimability of the molecule are improved compared to the case where a hydrogen atom or an alkyl group is bonded to the 1-position. Therefore, a light-emitting device with good reliability can be obtained. In addition, when an organic EL device is manufactured using the vacuum evaporation method, the organic compound of one aspect of the present invention can be preferably used.

[0080] <Condensation position of imidazole skeleton and naphthalene skeleton> In addition, the 1H-naphtho[1,2-d]imidazole skeleton of the organometallic complex of one aspect of the present invention can be regarded as a structure in which a naphthalene skeleton is condensed to an imidazole skeleton. Here, when the naphthalene skeleton has a structure condensed at the a-position of the imidazole skeleton, an Ir complex having the structure shown in the following general formula (I-1) can be considered as an example. When the naphthalene skeleton has a structure condensed at the a-position of the imidazole skeleton, an Ir complex having the structure shown in the following general formula (I-1) can be considered as an example. I-1)

[0081]

Chem.

[0082] In general formula (I-1), R 1 to R 7 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms , a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

[0083] The structure represented by general formula (I-1) has a structure in which the imidazole skeleton bonded to Ir and the benzene skeleton bonded to Ir are condensed with each other. This structure tends not to have a high quantum yield . Also, since the imidazole skeleton bonded to Ir and the benzene skeleton bonded to Ir are condensed , it is expected to emit light at a longer wavelength compared to the case where they are not condensed. Therefore, it is expected to be an unsuitable skeleton for blue and green phosphorescent materials, which are particularly in demand for development .

[0084] On the other hand, the 1H-naphtho[1,2-d]imidazole skeleton of the organometallic complex of one aspect of the present invention has a structure in which a naphthalene skeleton is condensed at the d-position of the imidazole skeleton. Here, when a naphthalene skeleton is condensed at the d-position of the imidazole skeleton, 1H-naphtho [1,2-d]imidazole skeleton and 1H-naphtho[2,1-d]imidazole skeleton are considered due to the difference in the condensation position . The influence of these differences in condensed carbon on the quantum yield was investigated by molecular orbital calculations . .

[0085] <Example of net charge calculation> In this calculation example, the 1H-naphtho[1,2-d]imidazole skeleton, which is one aspect of the present invention, was used Using the organometallic complex as a model, Compound-A, and as a comparison, 1H-naphtho Compound-B with an organometallic complex having a 2,1-d]imidazole skeleton as a model The calculation example of the lowest triplet excited state (T 1 state) of is specifically exemplified. Compound- The structures of A and Compound-B are shown below. In Compound-A, the benzene ring of a shown in the structural formula is condensed on the side opposite to Ir when viewed from the N (nitrogen) bonded to Ir On the other hand, in Compound-B, the benzene ring of b shown in the structural formula is condensed on the same side as Ir when viewed from the N (nitrogen) bonded to Ir . When a 1H-naphtho[2,1-d]imidazole skeleton is used as a ligand of the Ir complex, it has a structure in which a benzene ring is condensed in the same orientation as Compound-B .

[0086]

Chemical formula

[0087] For the molecular orbital calculations, the Gaussian09 program was used. The functional was B3PW9 1, and structural optimization and vibrational calculations were performed. The basis function used was LANL2DZ for Ir and 6-311G for the other elements .

[0088] The net charge on Ir in the optimized structure obtained by the calculation was 0.30 for Compound-A, whereas it was calculated to be 0.20 for Compound-B .

[0089] As a result, the net charge of Ir in Compound-A was found to be significantly higher than that in Compound-B . Metal-Ligand Charge Transfer (ML CT) is the 5d orbital of Ir and the π of the ligand* is a transition that contributes. One of the factors for high MLCT properties is that the net charge of Ir in the excited state is high. Therefore, Compound-A using the organometallic complex which is one aspect of the present invention as a model has higher MLCT properties in the excited state than Compound- B. It is known that there is a correlation between MLCT properties and the quantum yield of phosphorescent materials and it is expected that a higher MLCT property leads to a higher luminescence quantum yield. Thus, it was found that the organic compound of one aspect of the present invention has a high luminescence quantum yield.

[0090] In Compound-B, the benzene ring represented by b in the structural formula exists in a direction that causes steric hindrance with Ir. Therefore, in Compound-B, it is expected that the bond distance between Ir and N ( nitrogen) of the imidazole skeleton becomes long. Therefore, it is considered that the net charge on Ir becomes small in Compound-B as described above. 1H-Naphtho[2,1-d] imidazole skeleton-containing Ir complex also has a benzene ring represented by b in the structural formula, so it is considered that the net charge is small in the same way as Compound-B. On the other hand, the benzene ring represented by a in the structural formula of Compound-A does not cause steric hindrance with Ir. Therefore, it is considered that a result of a larger net charge than Compound-B was obtained.

[0091] Based on the above, when considering an organometallic complex having a structure in which a naphthalene skeleton is condensed to an imidazole skeleton, an organometallic complex with good luminescence quantum yield can be obtained by using a 1H-naphtho[1,2-d]imidazole skeleton.

[0092] The aryl group having 6 to 25 carbon atoms is preferably a substituted or unsubstituted phenyl group. By having such a structure, the organometallic complex of one aspect of the present invention can be synthesized inexpensively and easily. Therefore, the general formula (G-1) preferably has a structure represented by the following general formula (G-2). By having such a structure, the organometallic complex of one aspect of the present invention can be synthesized inexpensively and easily. Therefore, the general formula (G-1) preferably has a structure represented by the following general formula (G-2). Therefore, the general formula (G-1) preferably has a structure represented by the following general formula (G-2). .

[0093] [Chemical formula]

[0094] In the general formula (G-2), R 1 to R 15 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or an electron-withdrawing group. each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or an electron-withdrawing group. each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or an electron-withdrawing group.

[0095] Further, the organometallic complex of one aspect of the present invention has a structure represented by the following general formula (G-3).

[0096] [Chemical formula]

[0097] In the general formula (G-3), R 11 , R 13 and R 15 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or an electron-withdrawing group. each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or an electron-withdrawing group.

[0098] In the general formulas (G-2) and (G-3), at least one of R 11 and R 15 is preferably an alkyl group having 1 to 6 carbon atoms. By having such a structure, a material having good sublimability Since it can be used, the material utilization efficiency can be increased when manufacturing a light-emitting element by vacuum evaporation method. Moreover, R 11 and R 15 When at least one of the phenyl group to which is bonded and R 11 and R 15 is an alkyl group having 1 to 6 carbon atoms, due to steric hindrance of the alkyl group harm, the dihedral angle formed by the phenyl group and the 1H-naphtho[1,2-d]imidazole skeleton becomes large. Therefore, since the conjugation between the phenyl group and the 1H-naphtho[1,2-d]imidazole skeleton is difficult to spread, the emission wavelength can be shortened. Further, it is more preferable that the alkyl group is a branched-chain alkyl group having 3 to 7 carbon atoms. By being a branched-chain alkyl group group, the above-described effect can be more easily obtained. Examples of the branched-chain alkyl group include an isopropyl group, an isobutyl group, and a tertiary butyl group. Therefore, the organometallic complex according to one embodiment of the present invention has a structure represented by the following general formula (G-4).

[0099] In general formula (G-4), R .

[0100]

Chemical formula

[0101] In general formula (G-4), R 13 represents hydrogen or an electron-withdrawing group.

[0102] In general formula (G-4), when R 13 is hydrogen, it is preferable because the synthesis becomes easy. Moreover, when R 13 is an electron-withdrawing group, the LUMO (Lowest Unoccupied Molecular Orbital, also referred to as the lowest unoccupied molecular orbital) level of the organometallic complex and and The HOMO (Highest Occupied Molecular Orbital, also referred to as the highest occupied orbital) level can be lowered. Therefore, when an organometallic complex is used in a light-emitting device, while maintaining the hole injection property, the electron injection property can be enhanced, and the luminous efficiency can be improved. In addition, it can be expected to enhance the CT (Charge Transfer) property, and the spectral width is expected to become wider. Therefore, a light-emitting device with high color rendering can be fabricated.

[0103] In addition, the organometallic complex of one embodiment of the present invention is an organometallic complex represented by the following general formula (G-5). It is as follows.

[0104]

Chemical formula

[0105] In the general formula (G-5), R 15 represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. It is as described above.

[0106] By introducing a cyano group, which is an electron-withdrawing group, at the 4-position of the phenyl group bonded to the 1-position of 1H-naphtho[1,2-d]imidazole, a light-emitting device with good luminous efficiency can be fabricated. In addition, a light-emitting device with high color rendering can be fabricated. It is as described above.

[0107] In addition, the organometallic complex of one embodiment of the present invention is an organometallic complex represented by the following general formula (G-6). It is as follows.

[0108]

Chemical formula

[0109] In the general formula (G-6), R 1 to R 10 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or an electron-withdrawing group, and Ar represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

[0110] The organometallic complex represented by the general formula (G-6) represents a tris complex in which all three ligands of the organometallic complex are the same ligand among the organometallic complexes represented by the general formula (G-1). The tris complex of the organometallic complex is preferred because of its good luminous efficiency and reliability.

[0111] In addition, the organometallic complex of one embodiment of the present invention is an organometallic complex represented by the following general formula (G-7).

[0112]

Chemical formula

[0113] In the general formula (G-7), R 1 to R 15 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or an electron-withdrawing group.

[0114] The organometallic complex represented by the general formula (G-7) represents a tris complex in which all three ligands of the organometallic complex are the same ligand among the organometallic complexes represented by the general formula (G-2). The tris complex of the organometallic complex is preferred because of its good luminous efficiency and reliability.

[0115] In addition, the organometallic complex of one embodiment of the present invention is an organometallic complex represented by the following general formula (G-8). There is.

[0116]

Chemical formula

[0117] In the general formula (G-8), R 11 , R 13 and R 15 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or an electron-withdrawing group. of an alkyl group, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or an electron-withdrawing group. represents an alkyl group, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or an electron-withdrawing group.

[0118] The organometallic complex represented by the general formula (G-8) represents a tris complex in which all three ligands of the organometallic complex are the same ligand among the organometallic complexes represented by the general formula (G-3). There is. The organometallic complex of the tris complex is preferable because of its good luminous efficiency and reliability. There is. The organometallic complex of the tris complex is preferable because of its good luminous efficiency and reliability.

[0119] In addition, the organometallic complex of one embodiment of the present invention is an organometallic complex represented by the following general formula (G-9). There is.

[0120]

Chemical formula

[0121] In the general formula (G-9), R 13 represents hydrogen or an electron-withdrawing group.

[0122] The organometallic complex represented by the general formula (G-9) represents a tris complex in which all three ligands of the organometallic complex are the same ligand among the organometallic complexes represented by the general formula (G-4). There is. The organometallic complex of the tris complex is preferable because of its good luminous efficiency and reliability. There is. The organometallic complex of the tris complex is preferable because of its good luminous efficiency and reliability.

[0123] Also, the organometallic complex of one embodiment of the present invention is an organometallic complex represented by the following general formula (G-10). It is as follows.

[0124] [Chemical formula]

[0125] In the general formula (G-10), R 15 represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl having 6 to 25 carbon atoms groups.

[0126] The organometallic complex represented by the general formula (G-10) represents a tris complex in which all three ligands of the organometallic complex are the same ligand among the organometallic complexes represented by the general formula (G-5). That is, the organometallic complex of the tris form is preferred because it has good luminous efficiency and reliability.

[0127] Also, the organometallic complex of one embodiment of the present invention is an organometallic complex represented by the following general formula (G-11). It is as follows.

[0128] [Chemical formula]

[0129] In the general formula (G-11), R 1 to R 10 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or an electron-withdrawing group, Ar represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, L represents a monoanionic ligand, and n represents 1 or 2. ​

[0130] The organometallic complex represented by the general formula (G-11) represents a heterocomplex, which is an organometallic complex having two or more ligands among the organometallic complexes represented by the general formula (G-1). The organometallic complex of the heterocomplex is preferable because the emission color and sublimability can be adjusted by selecting the combination of the ligands. Moreover, the organometallic complex of one aspect of the present invention is an organometallic complex represented by the following general formula (G-12).

[0131]

[0132]

Chemical formula

[0133] In the general formula (G-12), R 1 to R 15 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or an electron-withdrawing group, L represents a monoanionic ligand, and n represents 1 or 2.

[0134] The organometallic complex represented by the general formula (G-12) represents a heterocomplex, which is a metal complex having two or more ligands among the organometallic complexes represented by the general formula (G-2). The organometallic complex of the heterocomplex is preferable because the emission color and sublimability can be adjusted by selecting the combination of the ligands.

[0135] Moreover, the organometallic complex of one aspect of the present invention is an organometallic complex represented by the following general formula (G-13).

[0136]

Chemical formula

[0137] In general formula (G-13), R 11 , R 13 and R 15 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or un substituted aryl group having 6 to 25 carbon atoms or an electron-withdrawing group, L represents a monoanionic ligand position, and n represents 1 or 2.

[0138] The organometallic complex represented by general formula (G-13) represents a heterocomplex, which is a metal complex having two or more ligands among the organometallic complexes represented by general formula (G-3). The organometallic complex of the heterocomplex is preferable because the emission color and sublimability can be adjusted by selecting the combination of ligands.

[0139] Further, the organometallic complex of one aspect of the present invention is an organometallic complex represented by the following general formula (G-14).

[0140]

Chemical formula

[0141] In general formula (G-14), R 13 represents hydrogen or an electron-withdrawing group, L represents a monoanionic ligand position, and n represents 1 or 2.

[0142] The organometallic complex represented by general formula (G-14) represents a heterocomplex, which is a metal complex having two or more ligands among the organometallic complexes represented by general formula (G-4). The organometallic complex of the heterocomplex is preferable because the emission color and sublimability can be adjusted by selecting the combination of ligands. ​​​​​​​

[0143] Further, the organometallic complex of one aspect of the present invention is an organometallic complex represented by the following general formula (G-15). It is as follows.

[0144] [Chemical formula]

[0145] In general formula (G-15), R 15 represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, L represents a monoanionic ligand, and n represents 1 or 2.

[0146] The organometallic complex represented by general formula (G-15) represents a heterocomplex, which is a metal complex having two or more ligands among the organometallic complexes represented by general formula (G-5). The organometallic complex of the heterocomplex is preferable because the emission color and sublimability can be adjusted by selecting the combination of ligands.

[0147] Further, among general formulas (G-11) to (G-15), the monoanionic ligand represented by L is preferably a monoanionic bidentate chelate ligand having a β-diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, a monoanionic bidentate chelate ligand having a phenolic hydroxyl group, or a monoanionic bidentate chelate ligand in which both coordination elements are nitrogen, or a bidentate ligand that forms a metal-carbon bond with iridium by cyclometalation. Specifically, it is preferably any one of the following general formulas (L1) to (L9).

[0148] [Chemical formula] ​​​​​​​​​​

[0149] In general formulas (L1) to (L9), R 21 to R 86 each independently represents hydrogen or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a halogeno group, a vinyl group, a cyano group, a substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. Further, A to A each independently represents nitrogen, or an sp hybridized carbon atom bonded to hydrogen, or an sp hybridized carbon atom having a substituent, and the substituent represents any one of an alkyl group having 1 to 6 carbon atoms, a halogeno group, a haloalkyl group having 1 to 6 carbon atoms, or a phenyl group. 1 to A 13 each independently represents nitrogen, or an sp hybridized carbon atom bonded to hydrogen, or an sp 2 hybridized carbon atom having a substituent, and the substituent represents any one of an alkyl group having 1 to 6 carbon atoms, a halogeno group, a haloalkyl group having 1 to 6 carbon atoms, or a phenyl group. 2 hybridized carbon atom having a substituent, and the substituent represents any one of an alkyl group having 1 to 6 carbon atoms, a halogeno group, a haloalkyl group having 1 to 6 carbon atoms, or a phenyl group. represents, and the substituent represents any one of an alkyl group having 1 to 6 carbon atoms, a halogeno group, a haloalkyl group having 1 to 6 carbon atoms, or a phenyl group. Here, the hetero-type organometallic complex has a plurality of types of ligands, but it is preferable that the HOMO and LUMO of the organometallic complex are distributed among the same type of ligands. In the case of such a configuration, an organometallic complex having particularly good luminous efficiency can be obtained. Therefore, in general formulas (G-11) to (G-

[0150] 15), it is particularly preferable that L is (L8) or (L9). The organometallic complex of one aspect of the present invention has an imidazole skeleton which is a 5-membered ring. Therefore, it is preferable that L also has a structure having a 5-membered ring skeleton. With such a configuration, the HOMO and LUM O of the organometallic complex are likely to be distributed among the same ligands. Here, the hetero-type organometallic complex has a plurality of types of ligands, but it is preferable that the HOMO and LUMO of the organometallic complex are distributed among the same type of ligands. In the case of such a configuration, an organometallic complex having particularly good luminous efficiency can be obtained. Therefore, in general formulas (G-11) to (G- 15), it is particularly preferable that L is (L8) or (L9). The organometallic complex of one aspect of the present invention has an imidazole skeleton which is a 5-membered ring. Therefore, it is preferable that L also has a structure having a 5-membered ring skeleton. With such a configuration, the HOMO and LUM O of the organometallic complex are likely to be distributed among the same ligands. O of the organometallic complex are likely to be distributed among the same ligands. O of the organometallic complex are likely to be distributed among the same ligands.

[0151] <Examples of substituents> In general formulas (G-1) to (G-15), R 1 to R15 represents, for example, hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or an electron-withdrawing group. Examples of the alkyl group include, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, an n-hexyl group, etc., and examples of the cyclo alkyl group include, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc., and examples of the aryl group include a phenyl group, a naphthyl group, a biphenyl group, a fluorenyl group, a spirofluorenyl group, etc. Examples of the electron-withdrawing group include a halogeno group, a cyano group, a nitro group, a carbonyl group, a haloalkyl group and, as the haloalkyl group, specifically, a trifluoromethyl group, etc. can be mentioned. More specifically, for example, groups represented by the following structural formulas (R-1) to (R-43) can be mentioned. In particular, a halogeno group, a cyano group, and a trifluoromethyl group are preferable because they have a large electron-withdrawing property and high stability. Note that the groups represented by R 1 to R 4 and R 5 to R 13 are not limited to these.

[0152] [Chemical formula]

[0153] At this time, when R 1 to R 10 are hydrogen, the organometallic complex of one aspect of the present invention can be synthesized simply and inexpensively. It is electrochemically stable and has good reliability, which is preferable. Also, other than hydrogen When it is a substituent, the heat resistance of the organometallic complex of one aspect of the present invention can be improved.( When it is an alkyl group or a cycloalkyl group as in (R-2) to (R-15), the solubility in an organic solvent becomes good, so that the purification of the organometallic complex of one aspect of the present invention can be easily carried out.( As in (R-16), (R-22) to (R-28), (R-31) and (R-32), an aryl group having no alkyl group or cycloalkyl group is electrochemically stable and reliable and has good properties.(

[0154] In general formulas (G-1), (G-6) and (G-11), or as a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, for example, a phenyl group, a naphthyl group, a biphenyl group , a fluorenyl group, a spirofluorenyl group and the like can be mentioned. Specifically, the groups represented by the following structural formulas( (Ar-1) to (Ar-25) can be applied. The group represented by Ar is not limited to these. Further, it may have a substituent.(

[0155]

Chemical formula

[0156] In general formulas (L1) to (L9), R 21 to R 86 are each independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a halogeno group, a vinyl group, a cyano group, a substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. The alkyl group and For example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, an n-hexyl group, etc. can be mentioned. As the halogeno group, a fluoro group, a chloro group, a bromo group, an iodo group can be mentioned. As the vinyl group, a vinyl group, a vinyl acetate group can be mentioned. As the haloalkyl group, a trifluoromethyl group, a pentafluoroethyl group, a trichloromethyl group can be mentioned. As the alkoxy group, a methoxy group, an ethoxy group, a phenoxy group can be mentioned. As the alkylthio group, a propylthio group, a butylthio group can be mentioned. As the aryl group, a phenyl group, a naphthyl group, a biphenyl group, a fluorenyl group, etc. can be mentioned. More specifically, for example, groups represented by the following structural formulas (R-50) to (R-95) can be mentioned. Note that the groups represented by R to R are not limited to these. For example, a methoxy group, an ethoxy group, a phenoxy group can be mentioned. As the alkylthio group, a propylthio group, a butylthio group can be mentioned. As the aryl group, a phenyl group, a naphthyl group, a biphenyl group, a fluorenyl group, etc. can be mentioned. More specifically, for example, groups represented by the following structural formulas (R-50) to (R-95) can be mentioned. Note that the groups represented by R to R are not limited to these. For example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, an n-hexyl group, etc. can be mentioned. As the cycloalkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, etc. can be mentioned. As the aryl group, a phenyl group, a naphthyl group, a biphenyl group, a fluorenyl group, etc. can be mentioned. More specifically, for example, groups represented by the following structural formulas (R-50) to (R-95) can be mentioned. Note that the groups represented by R to R 21 to R 86 are not limited to these. In addition, in the above general formulas (G1) to (G15), when Ar, R

[0157]

Chemical formula

[0158] to R 1 to R 15 and R 21 to R 86 further have substituents, the substituents can include an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. As the alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert -butyl group, an n-hexyl group, etc. can be mentioned. As the cycloalkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert -butyl group, an n-hexyl group, etc. can be mentioned. As the cycloalkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, etc. can be mentioned. The aryl group can be a phenyl group, a naphthyl group, a biphenyl group, a fluorenyl group, etc. More specifically, for example, groups represented by the following structural formulas (R-50) to (R-95) can be mentioned. Note that the groups represented by R Examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc. Examples of the aryl group include a phenyl group, a naphthyl group, a fluorenyl group, etc. can be given as specific examples.

[0159] <Specific Examples of Compounds> Specific structures of the compounds represented by General Formulas (G-1) to (G-15) include the following organometallic complexes represented by Structural Formulas (100) to (123) and Structural Formulas (200) to (223). It should be noted that the organometallic complexes represented by General Formulas (G-1) to (G-15) are not limited to the following examples.

[0160]

Chemical Formula

[0161]

Chemical Formula

[0162]

Chemical Formula

[0163]

Chemical Formula

[0164]

Chemical Formula

[0165]

Chemical Formula

[0166]

Chemical Formula

[0167] Note that the organometallic complex in the present embodiment can be formed using methods such as vapor deposition method (including vacuum vapor deposition method), inkjet method, coating method, gravure printing method, and the like.

[0168] Note that the present embodiment can be appropriately combined with other embodiments.

[0169] (Embodiment 2)

[0170] In the present embodiment, an example of a method for synthesizing an organometallic complex according to one aspect of the present invention will be described.

[0171] ≪Synthesis method of 1H-naphtho[1,2-d]imidazole derivative represented by general formula (g-1) method≫ An example of the synthesis method of the 1H-naphtho[1,2-d]imidazole derivative represented by the following general formula (g-1) will be described. One aspect of the present invention having a structure represented by general formula (G-1) The organometallic complex has a 1H-naphtho[1,2-d]imidazole derivative represented by general formula (g-1) as a ligand. Therefore, by synthesizing an Ir complex using the 1H-naphtho[1, 2-d]imidazole derivative, as described later, an organometallic complex according to one aspect of the present invention can be synthesized.

[0172]

Chemical formula

[0173]

[0173] In general formula (g-1), R 1 to R 10 are each independently hydrogen, alkyl having 1 to 6 carbon atoms a group selected from a group consisting of a hydrogen atom, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and an electron-withdrawing group, and Ar represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. to 25 carbon atoms, or an electron-withdrawing group, and Ar represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

[0174] As shown in the following Scheme (S-1), an arylaldehyde compound or an arylcarbonyl chloride (M1) and an o-naphthalenediamine derivative (M2) in which the N-position is substituted with Ar react to obtain a 1H-naphtho[1,2-d]imidazole derivative represented by the general formula (g-1).

[0175] [Chemical formula]

[0176] In Scheme (S-1), R 1 to R 10 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or an electron-withdrawing group, and Ar represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. carbon atoms.

[0177] [Synthesis method of the organometallic complex represented by the general formula (G-6)] Next, an example of a method for synthesizing an organometallic complex having a structure represented by the general formula (G-1) will be described. Specifically, an example of a method for synthesizing an organometallic complex represented by the general formula (G-6) will be described.

[0178] As shown in the following Scheme (S-2), a 1H-naphtho[1, 2-d]imidazole derivative represented by the general formula (g-1) and an iridium metal compound containing a halogen (iridium chloride Hydrates, ammonium hexachloroiridate, etc.) or iridium organometallic complexation After mixing with a compound (acetylacetonato complex, diethyl sulfide complex, etc.), heat By doing so, an organometallic complex having a structure represented by the general formula (G-6) can be obtained . Further, this heating process may be carried out after dissolving the 1H-naphtho[1,2-d] imidazole derivative represented by the general formula (g-1), an iridium metal compound containing a halogen, or an iridium organo metal complex in an alcohol solvent (glycerol, ethylene glycol, 2-methoxyethanol -ol, 2-ethoxyethanol, etc.). In Scheme (S- 2), R 1 to R 10 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or an electron-withdrawing group, and Ar represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

[0179] [Chemical formula]

[0180] However, the method for synthesizing the organometallic complex of the present invention is not limited to Scheme (S-2) only .

[0181] [Synthesis method of organometallic complex represented by general formula (G-11)] Next, an example of the synthesis method of the organometallic complex represented by the general formula (G-11) among the synthesis methods of the organometallic complex containing the structure represented by the general formula (G-1) will be described.

[0182] As shown in the following Scheme (S-3), 1H-naphtho[1, 2-d]imidazole derivative or L and an iridium compound containing halogen (iridium chloride, iridium bromide, iridium iodide, etc.) are heated in an inert gas atmosphere without a solvent or using an alcoholic solvent (glycerol, ethylene glycol, 2-methoxyethanol, 2-ethoxyethanol, etc.) alone or a mixed solvent of one or more alcoholic solvents and water, ) to obtain a binuclear complex (P1) of a 1H-naphtho[1,2-d]imidazole derivative, which is a kind of organometallic complex having a structure crosslinked by halogen, or a binuclear complex (P2) containing a monoanionic bidentate ligand. In Scheme (S-3), X represents a halogen atom, and R to R are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms 1 to 10 (S-3), X represents a halogen atom, and R an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or an electron-withdrawing group, and Ar represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

[0183] [Chemical formula]

[0184] Furthermore, as shown in the following Scheme (S-4), the binuclear complex (P1) or (P2) obtained in the above synthetic scheme (S-3) and a 1H-naphtho[1, 2-d]imidazole derivative or L represented by the general formula (g-1) are reacted in an inert gas atmosphere to obtain an organometallic complex according to one embodiment of the present invention represented by the general formula (G-11). Here, 2-d]imidazole derivative or L represented by the general formula (g-1) are reacted in an inert gas atmosphere to obtain an organometallic complex according to one embodiment of the present invention represented by the general formula (G-11). Here, by further irradiating the obtained organometallic complex with light or heat and further reacting it, geometric isomers are obtained. Isomers such as the body and optical isomers may be obtained, and these are also the present invention represented by the general formula (G-11) is an organometallic complex which is one aspect thereof. In Scheme (S-4), X represents a halogen atom, and R 1 to R 10 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 2 5 carbon atoms or an electron-withdrawing group, and Ar represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

[0185]

Chemical formula

[0186] However, the method for synthesizing the organometallic complex of the present invention is not limited to only Schemes (S-3) and (S-4). It is not defined.

[0187] (Embodiment 3) In this embodiment, a light-emitting device having an organometallic complex which is one aspect of the present invention will be described below with reference to FIG. 1 used.

[0188] <Configuration Example 1 of Light-Emitting Device> First, the configuration of the light-emitting device according to one aspect of the present invention will be described below with reference to FIGS. 1(A), (B), and (C). described below.

[0189] FIG. 1(A) is a cross-sectional schematic view of a light-emitting device 150 according to one aspect of the present invention.

[0190] The light-emitting device 150 has a pair of electrodes (electrode 101 and electrode 102), and an EL layer 100 provided between the pair of electrodes has. The EL layer 100 has at least a light-emitting layer 140 .

[0191] In addition, as shown in FIG. 1(A), the EL layer 100 has functional layers such as a hole injection layer 111, a hole transport layer 112, an electron transport layer 118, and an electron injection layer 119 in addition to the light emitting layer 140.

[0192] In this embodiment, of the pair of electrodes, electrode 101 is used as the anode and electrode 1 02 is used as the cathode for explanation. However, the configuration of the light emitting element 150 is not limited thereto. That is, electrode 101 may be used as the cathode, electrode 102 may be used as the anode, and the lamination of each layer between the electrodes may be in the reverse order. That is, from the anode side, the hole injection layer 111, the hole transport layer 112, the light emitting layer 140, the electron transport layer 118, and the electron injection layer 119 may be laminated in this order.

[0193] Note that the configuration of the EL layer 100 is not limited to the configuration shown in FIG. 1(A), and may be a configuration having at least one selected from the hole injection layer 111, the hole transport layer 112, the electron transport layer 118, and the electron injection layer 119. Alternatively, the EL layer 100 may be a configuration having a functional layer that can reduce the injection barrier of holes or electrons, improve the transportability of holes or electrons, inhibit the transportability of holes or electrons, or suppress the quenching phenomenon by the electrode. Note that each functional layer may be a single layer or a configuration in which a plurality of layers are laminated.

[0194] The light emitting element 150 may contain an organometallic complex according to one aspect of the present invention in any layer of the EL layer 100. Note that the organometallic complex has a good quantum yield. Therefore, by using it as the guest material of the light emitting layer 140, a light emitting element with good luminous efficiency can be obtained.

[0195] Figure 1(B) is a schematic cross-sectional view showing an example of the light-emitting layer 140 shown in Figure 1(A). Figure 1( The light-emitting layer 140 shown in B) has a host material 141 and a guest material 142. Also , the host material 141 may be composed of a single organic compound, or may be a co-host system having organic compounds 141 _1 and organic compound 141_2. The organometallic complex of one aspect of the present invention can be preferably used as the guest material 142.

[0196] Also, as the guest material 142, a light-emitting organic material may be used. As the light-emitting organic material, materials that can emit fluorescence (hereinafter referred to as fluorescent materials) or materials that can emit phosphorescence (hereinafter also referred to as phosphorescent materials) can be mentioned. However, phosphorescent materials are preferred because of their high luminous efficiency. Therefore, the organometallic complex of one aspect of the present invention can be preferably used . In the following description, a configuration using a phosphorescent material as the guest material 142 will be described . Note that the guest material 142 may be read as a phosphorescent material.

[0197] When two types of host materials such as organic compounds 141_1 and organic compound 141_2 are used in the light-emitting layer as shown in Figure 1(B) (co-host system), generally, one type of electron-transporting material and one type of hole-transporting material are used for the two types of host materials. Such a configuration is preferable because the hole injection barrier between the hole transport layer 112 and the light-emitting layer 140 and the electron injection barrier between the electron transport layer 118 and the light-emitting layer 140 become small, and the driving voltage can be reduced. layer 140 become small, so that the driving voltage can be reduced, which is a preferable configuration.

[0198] <Light-emitting mechanism of the light-emitting element> Next, the light-emitting mechanism of the light-emitting layer 140 will be described below.

[0199] The organic compounds 141_1 and 141_2 contained in the host material 141 in the light-emitting layer 140 may form an exciplex (also referred to as an exciplex, exiplex, or Exciplex). Hereinafter, the case where the organic compounds 141_1 and 141_2 form an exciplex will be described. The correlation of the energy levels among the organic compound 141_1, the organic compound 141_2, and the guest material 142 in the light-emitting layer 140 is shown in Fig. 1(C). Note that the notations and symbols in Fig. 1(C) are as follows. Hereinafter, the organic compound 141_1 will be described as an electron-transporting material, and the organic compound 141_2 will be described as a hole-transporting material.

[0200] ·Host(141_1): Organic compound 141_1 (host material) ·Host(141_2): Organic compound 141_2 (host material) ·Guest(142): Guest material 142 (phosphorescent compound) ·S PH1 : S1 level of the organic compound 141_1 (host material) ·T PH1 : T1 level of the organic compound 141_1 (host material) ·S PH2 : S1 level of the organic compound 141_2 (host material) ·T PH2 : T1 level of the organic compound 141_2 (host material) ·S PG : S1 level of the guest material 142 (phosphorescent compound) ·T PG : T1 level of the guest material 142 (phosphorescent compound) ·S PE : S1 level of the exciplex ·T PE : T1 level of the exciplex

[0201] ​​​​​​Organic compound 141_1 and organic compound 141_2 form an exciplex, and the S 1 level (S PE ) and the T1 level (T PE ) are adjacent energy levels to each other (Figure 1( C) Route E 1 Refer to).

[0202] When organic compound 141_1 receives an electron and organic compound 141_2 receives a hole, an exciplex is rapidly formed. Alternatively, when one of them is in an excited state, it rapidly interacts with the other to form an exciplex. Therefore, most of the excitons in the light-emitting layer 140 exist as an exciplex. The excitation energy level (S PE or T PE ) of the exciplex is lower than the S1 levels (S and S PH1 and S PH2 ) of the host materials (organic compound 141_1 and organic compound 141_2) that form the exciplex. Thus, it becomes possible to form the excited state of host material 141 with a lower excitation energy. As a result, the driving voltage of the light-emitting device can be lowered . Note that it is also possible that organic compound 141_1 receives a hole and organic compound 141_2 receives an electron to form an exciplex.

[0203] Then, by transferring the energies of both (S PE ) and (T PE ) of the exciplex to the T1 level of the guest material 142 (phosphorescent compound), light emission can be obtained (Figure 1(C) Route E 2 , E 3 Refer to).

[0204] Note that the T1 level (T PE ) of the exciplex is lower than the T1 level (T PG ) of the guest material 142 It is preferably large. By doing so, the singlet excitation energy and the triplet excitation energy of the generated exciplex can be transferred from the S1 level (S ) and the T1 level (T PE ) of the exciplex to the T1 level (T PE ) of the guest material 142. Furthermore, in order to efficiently transfer the excitation energy from the exciplex to the guest material 142, PG ) of the guest material 142.

[0205] In addition, in order to efficiently transfer the excitation energy from the exciplex to the guest material 142, the T1 level (T PE ) of the exciplex is preferably equal to or smaller than the T1 levels (T ) of the organic compounds 141_1 and 141_2 that form the exciplex. By this, quenching of the triplet excitation energy of the exciplex by each organic compound (organic compound 141_1 and organic compound 141_2) is less likely to occur, PH1 and energy transfer from the exciplex to the guest material 142 occurs efficiently. PH2 ) of each organic compound (organic compound 141_1 and organic compound 141_2).

[0206]

[0207] In addition, when the combination of the organic compound 141_1 and the organic compound 141_2 is a combination of a compound having hole transportability and a compound having electron transportability, the carrier balance can be easily controlled by the mixing ratio. Specifically, the range of the compound having hole transportability: the compound having electron transportability = 1:9 to 9:1 (weight ratio) is preferable. Furthermore, since the carrier balance can be easily controlled by having the above configuration, the control of the carrier recombination region can also be easily performed.

[0207] Note that the processes of the above-described route E 2 , E 3 are referred to as ExTET (Exc It may be referred to as “iplex-Triplet Energy Transfer” That is to say, there is an excitation energy supply from an exciplex to the guest material 142 in the light-emitting layer 140 Note that in this case, it is not necessarily required that PE the reverse intersystem crossing efficiency from T PE to S is high nor is it necessary that the light emission quantum yield from S PE is high. Therefore, a wide range of materials can be selected In addition, by using ExTET, a light-emitting device with good luminous efficiency, reduced driving voltage, and good reliability can be obtained

[0208] The combination of the organic compound 141_1 and the organic compound 141_2 only needs to be a combination capable of forming an exciplex, but it is preferable that one has a HOMO level lower than the HOMO level of the other and has a LUMO level lower than the LUMO level of the other

[0209] <Material> Next, the details of the components of the light-emitting device according to one embodiment of the present invention will be described below

[0210] ≪Light-emitting layer≫ In the light-emitting layer 140, the host material 141 is present in the largest amount by weight, and the guest material 142 is dispersed in the host material 141. When the guest material 142 is a phosphorescent compound, the T1 level of the host material 141 (organic compound 141_1 and organic compound 141_2) of the light-emitting layer 140 is preferably higher than the T1 level of the guest material (guest material 142) of the light-emitting layer

[0211] The organic compound 141_1 is preferably a compound having a nitrogen-containing six-membered heteroaromatic ring skeleton Specific examples include a pyridine skeleton, a diazine skeleton (pyrazine skeleton, pyrimidine skeleton​​​​​ , and compounds having a pyridazine skeleton and a triazine skeleton. These salts Examples of the compound having a basic nitrogen-containing heteroaromatic ring skeleton include pyridine derivatives, bipyridine derivatives, pyrimidine derivatives, triazine derivatives, quinoxaline derivatives, dibenzo quinoxaline derivatives, phenanthroline derivatives, purine derivatives, and other compounds. In addition, as the organic compound 141_1, a material with higher electron transportability than hole (electron transport material) can be used, and it is preferably a material having an electron mobility of 1×10 cm -6 / Vs or more. 2

[0212] Specifically, for example, heteroaromatic ring compounds having a pyridine skeleton such as bathophenanthroline (abbreviation: Bphen), bathocuproine (abbreviation: BCP), and 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDB TPDBq-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3- yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2- 3'-(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]qui noxaline (abbreviation: 2mCzBPDBq), 2-[4-(3,6-diphenyl-9H-ca rbazol-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPD Bq-III), 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f ,h]quinoxaline (abbreviation: 7mDBTPDBq-II), and 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBT ,h]quinoxaline (abbreviation: 6mDBT PDBq-II), and 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBT (PDBq-II), (2-[3-(3,9'-bi-9H-carbazol-9-yl)phenyl) dibenzo[f,h]quinoxaline)(abbreviation: 2mCzCzPDBq), 4,6-bis [3-(phenanthren-9-yl)phenyl]pyrimidine(abbreviation: 4,6mPnP2 Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine(abbreviation: 4 ,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazol-9-yl) phenyl]pyrimidine(abbreviation: 4,6mCzP2Pm) and other heteroaromatic compounds having a diazine skeleton, and 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)- 9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 9-[3-(4,6-diphenyl-1,3,5-tri azine-2-yl)phenyl]-9'-phenyl-2,3'-bi-9H-carbazole( abbreviation: mPCCzPTzn-02) and other heteroaromatic compounds having a triazine skeleton, and 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine(abbreviation: 35 DCzPPy), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene(abbreviation: TmPyPB) and other heteroaromatic compounds having a pyridine skeleton can also be used. Among the above described heteroaromatic compounds, heteroaromatic compounds having a triazine skeleton, a diazine (pyrimidine, pyrazine, pyridazine) skeleton, or a pyridine skeleton are stable, reliable and preferable. In addition, heteroaromatic compounds having such a skeleton have high electron transportability and contribute to reducing the driving voltage. Also, poly(2,5-pyridinediyl)(abbreviation: PPy), poly [(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5- Poly[(9,9-dioctylfluorene-2,7-diyl)] (abbreviation: PF-Py), poly[(9,9-dioctylfluorene-2,7-di yl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy) and other polymer compounds can also be used. The substances described here mainly have an electron mobility of 1×10 -6 c m 2 / Vs or higher. As long as the substance has higher electron transportability than holes, substances other than the above can be used.

[0213] As the organic compound 141_2, a compound having a nitrogen-containing five-membered heteroaromatic ring skeleton or a tertiary amine skeleton is preferable. Specifically, compounds having a pyrrole skeleton or an aromatic amine skeleton can be mentioned. For example, indole derivatives, carbazole derivatives, triarylamine derivatives and the like can be mentioned. In addition, as the nitrogen-containing five-membered heteroaromatic ring skeleton, an imidazole skeleton, a triazole skeleton, and a tetrazole skeleton can be mentioned. Further, as the organic compound 141_2, a material having higher hole transportability than electrons (hole transport material) can be used, and it is preferably a material having a hole mobility of 1×10 cm / Vs or higher. Further, the hole transport material may be a polymer compound. -6 cm 2

[0214] As these materials with high hole transportability, specifically, as aromatic amine compounds, N, N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DT DPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), N,N'-bis{4-[bis(3-methylphenyl amino)phenyl]phenylamine, N,N'-bis{4-[bis(3-methylphenyl ​​​{[4-(Diphenylamino)phenyl]amino}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'- diamine (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)- N-phenylamino]benzene (abbreviation: DPA3B), etc. can be mentioned. .

[0215] Also, as the carbazole derivatives, specifically, 3-[N-(4-diphenylamino phenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA1 ), 3,6-bis[N-(4-diphenylaminophenyl)-N-phenylamino]-9 -phenylcarbazole (abbreviation: PCzDPA2), 3,6-bis[N-(4-diphenyl laminophenyl)-N-(1-naphthyl)amino]-9-phenylcarbazole (abbreviation : PCzTPN2), 3-[N-(9-phenylcarbazol-3-yl)-N-phenyl amino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N- (9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarb azole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarb azole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) etc. can be mentioned.

[0216] Also, as the carbazole derivatives, among others, 4,4'-di(N-carbazolyl)biphe nyl (abbreviation: CBP), 1,3,5-tris[4-(N-carbazolyl)phenyl]ben zene (abbreviation: TCPB), 9-[4-(10-phenyl-9-anthryl)phenyl]- 9H-carbazole (abbreviation: CzPA), 1,4-bis[4-(N-carbazolyl)phenyl]phe Nile]-2,3,5,6-tetraphenylbenzene, etc. can be used.

[0217] Also, N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl -9H-carbazole-3-amine (abbreviation: CzA1PA), 4-(10-phenyl- 9-anthryl)triphenylamine (abbreviation: DPhPA), 4-(9H-carbazole -9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)f enyl]-9H-carbazole-3-amine (abbreviation: PCAPA), N,9-diphenyl -N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H- carbazole-3-amine (abbreviation: PCAPBA), N,9-diphenyl-N-(9,1 0-diphenyl-2-anthryl)-9H-carbazole-3-amine (abbreviation: 2PCA PA), 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9 H-carbazole (abbreviation: PCzPA), 3,6-diphenyl-9-[4-(10-phe nyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), N, N,N’,N’,N’’,N’’,N’’’,N’’’-octaphenyldibenzog, p]chrysene-2,7,10,15-tetraamine (abbreviation: DBC1), etc. can be used.

[0218] Also, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriph enylamine) (abbreviation: PVTPA), poly[N-(4-{N’-[4-(4-diphenyl [[Amino)phenyl]phenyl-N'-phenylamino}phenyl]methacrylamide]( Abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis (phenyl)benzidine](abbreviation: Poly-TPD), etc., can also be used be done.

[0219] Furthermore, as materials with high hole transport properties, for example, 4,4'-bis[N-(1-naphthyl yl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD) or N,N'- bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4, 4'-diamine (abbreviation: TPD), 4,4',4''-tris(carbazol-9-yl )triphenylamine (abbreviation: TCTA), 4,4',4''-tris[N-(1-naph thyl)-N-phenylamino]triphenylamine (abbreviation: 1'-TNATA), 4,4 ',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDAT A), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino] triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(spiro-9,9' -bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), 4 -phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluorene-9-yl)triphe nylamine (abbreviation: mBPAFLP), N-(9,9-dimethyl-9H-fluorene-2 -yl)-N-{9,9-dimethyl-2-[N'-phenyl-N'-(9,9-dimethyl -9H-fluorene-2-yl)amino]-9H-fluorene-7-yl}phenylamine N-(abbreviation: DFLADFL), N-(9,9-dimethyl-2-diphenylamino-9H- fluorene-7-yl)diphenylamine (abbreviation: DPNF), 2-[N-(4-diphe nylaminophenyl)-N-phenylamino]spiro-9,9'-bifluorene (abbreviation: DPASF), 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9- phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1B P), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''- (9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBN BB), 4-phenyldiphenyl-(9-phenyl-9H-carbazol-3-yl)a mine (abbreviation: PCA1BP), N,N'-bis(9-phenylcarbazol-3-yl) -N,N'-diphenylbenzene-1,3-diamine (abbreviation: PCA2B), N,N', N''-triphenyl-N,N',N''-tris(9-phenylcarbazol-3-yl l)benzene-1,3,5-triamine (abbreviation: PCA3B), N-(4-bipheny l)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9-phenyl-9H-carb azole-3-amine (abbreviation: PCBiF), N-(1,1'-biphenyl-4-yl) -N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-di methyl-9H-fluorene-2-amine (abbreviation: PCBBiF), 9,9-dimethyl-N -phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]f Loren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl -9H-carbazol-3-yl)phenyl]spiro-9,9'-bifluorene-2-a mine (abbreviation: PCBASF), 2-[N-(9-phenylcarbazol-3-yl)-N -phenylamino]spiro-9,9'-bifluorene (abbreviation: PCASF), 2,7-bis [N-(4-diphenylaminophenyl)-N-phenylamino]-spiro-9,9' -bifluorene (abbreviation: DPA2SF), N-[4-(9H-carbazol-9-yl) phenyl]-N-(4-phenyl)phenylaniline (abbreviation: YGA1BP), N,N' -bis[4-(carbazol-9-yl)phenyl]-N,N'-diphenyl-9,9- dimethylfluorene-2,7-diamine (abbreviation: YGA2F) and other aromatic amine compounds etc. can be used. Also, 3-[4-(1-naphthyl)-phenyl]-9-phen yl-9H-carbazole (abbreviation: PCPN), 3-[4-(9-phenanthryl)-phe nyl]-9-phenyl-9H-carbazole (abbreviation: PCPPn), 3,3'-bis(9 -phenyl-9H-carbazole) (abbreviation: PCCP), 1,3-bis(N-carbazolyl yl)benzene (abbreviation: mCP), 3,6-bis(3,5-diphenylphenyl)-9-phe nylcarbazole (abbreviation: CzTP), 3,6-di(9H-carbazol-9-yl) -9-phenyl-9H-carbazole (abbreviation: PhCzGI), 2,8-di(9H-carb azole-9-yl)-dibenzothiophene (abbreviation: Cz2DBT) and other amine compounds, carbazole compounds etc. can be used. Among the above-mentioned compounds, pyrrole skeletons, Compounds having an aromatic amine skeleton are preferred as they are stable and have good reliability. Further, the compounds having such a skeleton have high hole transporting properties and contribute to reducing the driving voltage. Compounds having such a skeleton have high hole transporting properties and contribute to reducing the driving voltage.

[0220] Also, as the organic compound 141_2, compounds having a nitrogen-containing five-membered heteroaromatic ring skeleton such as an imidazole skeleton, a triazole skeleton, and a tetrazole skeleton can be used. Specifically, for example, 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 9-[4-(4,5-diphenyl-4H-1,2,4-triazol-3-yl)phenyl]-9H-carbazole (abbreviation: CzTAZ1), 2,2’,2’’-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), etc. can be used. Compounds having such a skeleton have high hole transporting properties and contribute to reducing the driving voltage. Specifically, for example, 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 9-[4-(4,5-diphenyl-4H-1,2,4-triazol-3-yl)phenyl]-9H-carbazole (abbreviation: CzTAZ1), 2,2’,2’’-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), etc. can be used. 9-[4-(4,5-diphenyl-4H-1,2,4-triazol-3-yl)phenyl]-9H-carbazole (abbreviation: CzTAZ1), 9-[4-(4,5-diphenyl-4H-1,2,4-triazol-3-yl)phenyl]-9H-carbazole (abbreviation: CzTAZ1), 2,2’,2’’-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2,2’,2’’-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), etc. can be used. 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), etc. can be used.

[0221] In the light-emitting layer 140, as the guest material 142, an organometallic complex of an aspect of the present invention can be preferably used. Since the organometallic complex of an aspect of the present invention has a high quantum yield, a light-emitting device with good luminous efficiency can be obtained. Further, in the case of a light-emitting device having a plurality of light-emitting units like the light-emitting device 250 described later, it is preferable to use the organic compound of an aspect of the present invention in the light-emitting layer of one light-emitting unit. There is no particular limitation on the guest material used in other light-emitting units, but as the fluorescent compound, anthracene derivatives, tetracene derivatives, chrysene derivatives, phenanthrene derivatives, pyrene derivatives, perylene derivatives, stilbene derivatives, etc. In the light-emitting layer 140, as the guest material 142, an organometallic complex of an aspect of the present invention can be preferably used. Since the organometallic complex of an aspect of the present invention has a high quantum yield, a light-emitting device with good luminous efficiency can be obtained. Further, in the case of a light-emitting device having a plurality of light-emitting units like the light-emitting device 250 described later, it is preferable to use the organic compound of an aspect of the present invention in the light-emitting layer of one light-emitting unit. There is no particular limitation on the guest material used in other light-emitting units, but as the fluorescent compound, anthracene derivatives, tetracene derivatives, chrysene derivatives, phenanthrene derivatives, pyrene derivatives, perylene derivatives, stilbene derivatives, etc. In the light-emitting layer 140, as the guest material 142, an organometallic complex of an aspect of the present invention can be preferably used. Since the organometallic complex of an aspect of the present invention has a high quantum yield, a light-emitting device with good luminous efficiency can be obtained. Further, in the case of a light-emitting device having a plurality of light-emitting units like the light-emitting device 250 described later, it is preferable to use the organic compound of an aspect of the present invention in the light-emitting layer of one light-emitting unit. There is no particular limitation on the guest material used in other light-emitting units, but as the fluorescent compound, anthracene derivatives, tetracene derivatives, chrysene derivatives, phenanthrene derivatives, pyrene derivatives, perylene derivatives, stilbene derivatives, etc. In the case of a light-emitting device having a plurality of light-emitting units like the light-emitting device 250 described later, it is preferable to use the organic compound of an aspect of the present invention in the light-emitting layer of one light-emitting unit. There is no particular limitation on the guest material used in other light-emitting units, but as the fluorescent compound, anthracene derivatives, tetracene derivatives, chrysene derivatives, phenanthrene derivatives, pyrene derivatives, perylene derivatives, stilbene derivatives, etc. In the case of a light-emitting device having a plurality of light-emitting units like the light-emitting device 250 described later, it is preferable to use the organic compound of an aspect of the present invention in the light-emitting layer of one light-emitting unit. There is no particular limitation on the guest material used in other light-emitting units, but as the fluorescent compound, anthracene derivatives, tetracene derivatives, chrysene derivatives, phenanthrene derivatives, pyrene derivatives, perylene derivatives, stilbene derivatives, etc. There is no particular limitation on the guest material used in other light-emitting units, but as the fluorescent compound, anthracene derivatives, tetracene derivatives, chrysene derivatives, phenanthrene derivatives, pyrene derivatives, perylene derivatives, stilbene derivatives, etc. There is no particular limitation on the guest material used in other light-emitting units, but as the fluorescent compound, anthracene derivatives, tetracene derivatives, chrysene derivatives, phenanthrene derivatives, pyrene derivatives, perylene derivatives, stilbene derivatives, etc. Body, acridone derivative, coumarin derivative, phenoxazine derivative, phenothiazine derivative etc. are preferable, and for example, the following substances can be used.

[0222] Specifically, 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2 ,2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl -9-anthryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2 BPy), N,N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoro ren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn) , N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H -fluorene-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMem FLPAPrn), N,N'-bis[4-(9-phenyl-9H-fluorene-9-yl )phenyl]-N,N'-bis(4-tert-butylphenyl)pyrene-1,6-dia mine (abbreviation: 1,6tBu-FLPAPrn), N,N'-diphenyl-N,N'-bis [4-(9-phenyl-9H-fluorene-9-yl)phenyl]-3,8-dicyclohe xylpyrene-1,6-diamine (abbreviation: ch-1,6FLPAPrn), N,N'-b is[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbe ne-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl) -4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA) , 4-(9H-carbazol-9-yl)-4'-(9,10-diphenyl-2-anth Ril) triphenylamine (abbreviation: 2YGAPPA), N, 9-diphenyl-N-[4- (10-phenyl-9-anthryl) phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra(tert-butyl)perylene (abbreviation: TBP), 4-(10-phenyl-9-anthryl)-4’-(9-phenyl- 9H-carbazole-3-yl)triphenylamine (abbreviation: PCBAPA), N,N’ ’-(2-tert-butylanthracene-9,10-diyl-di-4,1-phenylene) bis[N,N’,N’-triphenyl-1,4-phenylenediamine] (abbreviation: DPAB PA), N, 9-diphenyl-N-[4-(9,10-diphenyl-2-anthryl)f enyl]-9H-carbazole-3-amine (abbreviation: 2PCAPPA), N-[4-(9 ,10-diphenyl-2-anthryl) phenyl]-N,N’,N’-triphenyl-1 ,4-phenylenediamine (abbreviation: 2DPAPPA), N,N,N’,N’,N’’,N ’’,N’’’,N’’’-octaphenyldibenzo[g,p]chrysene-2,7,10 ,15-tetraamine (abbreviation: DBC1), coumarin 30, N-(9,10-diphenyl -2-anthryl)-N, 9-diphenyl-9H-carbazole-3-amine (abbreviation: 2 PCAPA), N-[9,10-bis(1,1’-biphenyl-2-yl)-2-anth ryl]-N, 9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCABPh A), N-(9,10-diphenyl-2-anthryl)-N,N’,N’-triphenyl -1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(1,1 ’-biphenyl-2-yl)-2-anthryl]-N,N’,N’-triphenyl-1, 4-Phenylenediamine (abbreviation: 2DPABPhA), 9,10-bis(1,1'-biphenyl-2-yl)-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), Coumarin 6, Coumarin 545T -phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), Coumarin 6, Coumarin 545T -phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), Coumarin 6, Coumarin 545T -phenylanthracen-9-amine (abbreviation: DPhAPhA), Coumarin 6, Coumarin 545T , N,N'-diphenylquinacridone (abbreviation: DPQd), Rubrene, 2,8-di-tert-butyl-5,11-bis(4-tert-butylphenyl)-6,12-diphenyltetracene (abbreviation: TBRb), Nile Red, 5,12-bis(1,1'-biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BPT), 2-(2-{2- [4-(dimethylamino)phenyl]ethenyl}-6-methyl-4H-pyran-4-ylidene)propanedinitrile (abbreviation: DCM1), 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N '-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTI) -diphenyltetracene (abbreviation: BPT), 2-(2-{2- [4-(dimethylamino)phenyl]ethenyl}-6-methyl-4H-pyran-4-ylidene)propanedinitrile (abbreviation: DCM1), 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N '-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTI) ,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl -4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N ',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methyl phenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p -mPhAFD), 2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl -2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl )ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTI) , 2-{2-tert-butyl-6-[2-(1,1,7,7-tetramethyl-2,3, 6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl] -4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTB), 2-(2, 6-bis{2-[4-(dimethylamino)phenyl]ethenyl}-4H-pyran-4-i lidene)propanedinitrile (abbreviation: BisDCM), 2-{2,6-bis[2-(8- methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H -benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}p ropanedinitrile (abbreviation: BisDCJTM), 5,10,15,20-tetraphenyl bisbenzo[5,6]indeno[1,2,3-cd:1’,2’,3’-lm]perylene , etc.

[0223] Phosphorescent compounds that can be used as guest materials include iridium, rhodium, or platinum-based organometallic complexes, or metal complexes. Among them, organoiridium complexes , for example, iridium-based orthometal complexes are preferred. Ligands for orthometalation include 4H-triazole ligands, 1H-triazole ligands, imidazole ligands, pyridine ligands, pyrimidine ligands, pyrazine ligands, or isoquinoline ligands, etc. can be mentioned. Examples of metal complexes include platinum complexes having porphyrin ligands.

[0224] Substances having an emission peak in blue or green, for example, tris{2-[5-(2 -methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazolo -yl-κN2]phenyl-κC}iridium(III) (abbreviation: [Ir(mp ptz-dmp) 3 )、tris(5-methyl-3,4-diphenyl-4H-1,2,4 -triazolato)iridium(III) (abbreviation: [Ir(Mptz) 3 )、tris[4 -(3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triaz olato]iridium(III) (abbreviation: [Ir(iPrptz-3b) 3 )、tris[3 -(5-biphenyl)-5-isopropyl-4-phenyl-4H-1,2,4-triaz olato]iridium(III) (abbreviation: [Ir(iPr5btz) 3 )、such as organometallic iridium complexes having a 4H- triazole skeleton, and tris[3-methyl-1-(2- methylphenyl)-5-phenyl-1H-1,2,4-triazolato]iridium(II I) (abbreviation: [Ir(Mptz1-mp) 3 )、tris(1-methyl-5-phenyl- 3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir (Prptz1-Me) 3 )、such as organometallic iridi um complexes having a 1H-triazole skeleton, and fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl -1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpmi) 3 )、 tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phena nthridinato]iridium(III) (abbreviation: [Ir(dmpimpt-Me) 3 ) of such as organometallic iridium complexes having an imidazole skeleton, and bis[2-(4’,6’- Difluorophenyl)pyridinato-N,C 2’ Iridium(III)tetrakis(1- Pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophen Ryl)pyridinato-N,C 2’ Iridium(III)picolinate (abbreviation: FIrpic ), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N, C 2’}Iridium(III)picolinate (abbreviation: [Ir(CF 3 ppy) 2 (pic )]), bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ Iri dium(III)acetylacetonate (abbreviation: [FIr(acac)]) and other organometallic iridium complexes having a phenylpyridine derivative with an electron- withdrawing group as a ligand can be mentioned. Among the above, organometallic iridium complexes having a nitrogen-containing five-membered heteroaromatic ring skeleton such as a 4H-triazole skeleton, a 1H-triazole skeleton, and an imi dazole skeleton are particularly preferable because they have high triplet excitation energy and are also excellent in reliability and luminescence efficiency. In addition, examples of substances having a luminescence peak in green or yellow include, for example, tris(4-methyl

[0225] -6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm) 3 ), tris(4-t-butyl-6-phenylpyrimidinato)iridium(III) (abbreviation :[Ir(tBuppm) ), (acetylacetonato)bis(6-methyl-4-phe 3 nylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm) (acac)] 2 ), etc. ​), (acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidinato) Iridium(III) (abbreviation: [Ir(tBuppm) 2 (acac)]), (acetyl acetonato)bis[4-(2-norbornyl)-6-phenylpyrimidinato]iridium (III) (abbreviation: [Ir(nbppm) 2 (acac)]), (acetylacetonato) bis[5-methyl-6-(2-methylphenyl)-4-phenylpyrimidinato]irid ium(III) (abbreviation: [Ir(mpmppm) 2 (acac)]), (acetylacetona to)bis{4,6-dimethyl-2-[6-(2,6-dimethylphenyl)-4-pyrimidi nyl-κN3]phenyl-κC}iridium(III) (abbreviation: [Ir(dmppm-d mp) 2 (acac)]), (acetylacetonato)bis(4,6-diphenylpyrimidi nato)iridium(III) (abbreviation: [Ir(dppm) 2 (acac)]), such as pi ridinium complexes having a limidine skeleton, and (acetylacetonato)bis(3,5 -dimethyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr -Me) 2 (acac)]), (acetylacetonato)bis(5-isopropyl-3-me thyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-iP r) 2 (acac)]), such as organometallic iridium complexes having a pyrazine skeleton, and tri (2-phenylpyridinato-N,C 2’ )iridium(III) (abbreviation: [Ir(pp y) 3 ), bis(2-phenylpyridinato-N,C 2’Iridium(III) acetyl acetonate (abbreviation: [Ir(ppy) 2 (acac)]), bis(benzo[h]quin olinato)iridium(III) acetylacetonate (abbreviation: [Ir(bzq) 2 (ac ac)]), tris(benzo[h]quinolinato)iridium(III) (abbreviation: [Ir( bzq) 3 )), tris(2-phenylquinolinato-N,C 2’ )iridium(III) (abbreviation: [Ir(pq) 3 ), bis(2-phenylquinolinato-N,C 2’ )irid ium(III) acetylacetonate (abbreviation: [Ir(pq) 2 (acac)]), such as organometallic iridium complexes having a pyridine skeleton, bis(2,4-diphenyl-1,3- oxazolato-N,C 2’ )iridium(III) acetylacetonate (abbreviation: [Ir (dpo) 2 (acac)]), bis{2-[4’-(perfluorophenyl)phenyl pyridinato-N,C 2’}iridium(III) acetylacetonate (abbreviation: [Ir (p-PF-ph) 2 (acac)]), bis(2-phenylbenzothiazolato-N,C 2’ )iridium(III) acetylacetonate (abbreviation: [Ir(bt) 2 (acac )]), in addition to organometallic iridium complexes such as tris(acetylacetonato)(monophenanthro line)terbium(III) (abbreviation: [Tb(acac) 3 (Phen)]), and rare earth metal complexes such as the above-mentioned ones can be mentioned. Among the above-mentioned ones, organometallic iri The indium complex is particularly preferred because it is outstandingly excellent in reliability and luminous efficiency.

[0226] In addition, examples of the substance having a light emission peak in yellow or red include (diisobutyryl methanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(II I) (abbreviation: [Ir(5mdppm) 2 (dibm)]), bis[4,6-bis(3-me thylphenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm) 2 (dpm)]), bis[4,6-di(naphthalen-1-yl) pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(d1n pm) 2 (dpm)]) and other organometallic iridium complexes having a pyrimidine skeleton, or ( acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III )(abbreviation: [Ir(tppr) 2 (acac)]), bis(2,3,5-triphenylpy razinato)(dipivaloylmethanato)iridium(III) (abbreviation: Ir(tppr) 2 (dpm)), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)qui noxalinato]iridium(III) (abbreviation: [Ir(Fdpq) 2 (acac)]) and other organometallic iridium complexes having a pyrazine skeleton, or tris(1-phenylisoqui linato-N,C 2’ )iridium(III) (abbreviation: [Ir(piq) 3 ), bis(1 -phenylisoquinolinato-N,C 2’ )iridium(III) acetylacetonate( abbreviation: [Ir(piq) 2(acac)])-containing organometallic iridium complexes, in addition to 2,3,7,8,12,13,17,18-octaethyl-21H,2 3H-porphyrin platinum(II) (abbreviation: [PtOEP])-like platinum complexes, and tris (1,3-diphenyl-1,3-propanedionato)(monophenanthroline) europium (III) (abbreviation: [Eu(DBM) 3 (Phen)]), tris[1-(2-ten yl)-3,3,3-trifluoroacetonato](monophenanthroline) europium (III) (abbreviation: [Eu(TTA) 3 (Phen)])-like rare earth metal complexes are included among them. Among the above-mentioned ones, the organometallic iridium complex having a pyrimidine skeleton is particularly preferable because of its excellent reliability and luminescence efficiency. In addition, the organometallic iridium complex having a pyrazine skeleton can obtain red luminescence with good chromaticity.

[0227] Organic compounds having a benzofuropyridine skeleton or a benzothienopyridine skeleton have a high T 1 level, so they can be suitably used as a host material for a light-emitting layer using a substance that can convert triplet excitation energy into luminescence as a light-emitting material. Therefore, as the light-emitting material contained in the light-emitting layer 140, any material that can convert triplet excitation energy into luminescence is preferable. As the material that can convert the triplet excitation energy into luminescence, in addition to the above-mentioned phosphorescent compounds, thermally activated delayed fluorescence (TADF) materials are included. Therefore, the part described as a phosphorescent compound may be read as a thermally activated delayed fluorescence material. Note that thermally activated delayed fluorescence ​​A fluorescent material has a small energy difference between the triplet excited energy level and the singlet excited energy level, and has the function of converting energy from the triplet excited state to the singlet excited state by reverse intersystem crossing . Therefore, upconversion (reverse intersystem crossing) from the triplet excited state to the singlet excited state is possible with a small amount of thermal energy, and efficient light emission (fluorescence) from the singlet excited state can be exhibited. Further, as conditions for efficiently obtaining thermally activated delayed fluorescence, the energy difference between the triplet excited energy level and the singlet excited energy level is preferably greater than 0 eV and 0.2 eV or less, more preferably greater than 0 eV and 0.1 eV or less.

[0228] When the thermally activated delayed fluorescence material is composed of one kind of material, for example, the following materials can be used.

[0229] First, fullerenes and their derivatives, acridine derivatives such as proflavine, eosin, etc. can be mentioned. Also, metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd), etc. can be mentioned. Examples of the metal-containing porphyrin include protoporphyrin- tin fluoride complex (SnF (Proto IX)), mesoporphyrin- tin fluoride complex (SnF 2 (Meso IX)), hematoporphyrin- tin fluoride complex (Sn 2 (Hemato IX)), coproporphyrin tetramethyl ester- tin fluoride complex (SnF 2 (Copro III-4Me)), octaethylporphyrin- tin fluoride complex (SnF 2 (Copro III-4Me)), octaethylporphyrin- tin fluoride complex (SnF ​2 (OEP)), etioporphyrin-tin fluoride complex (SnF 2 (E tio I)), octaethylporphyrin-platinum chloride complex (PtCl 2 OEP), etc. are exemplified. can be mentioned.

[0230] In addition, as a thermally activated delayed fluorescence material composed of a single material, heteroaromatic compounds having a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring can also be used. Specifically 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[2, 3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ ), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carb zol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 2-[4-(10H-phenoxazin-10-yl)phenyl]- 4,6-diphenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4-( 5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5-dip enyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-dimeth yl-9H-acridin-10-yl)-9H-xanthene-9-one (abbreviation: ACRXT N), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulf hone (abbreviation: DMAC-DPS), 10-phenyl-10H,10’H-spiro[acri dine-9,9’-anthracene]-10’-one (abbreviation: ACRSA), etc. can be mentioned. The heteroaromatic compound has a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring, so It is preferable to have high electron transport property and hole transport property. Among them, having a π-electron deficient heteroaromatic ring In the skeleton having, a diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton), or A triazine skeleton is preferable because it is stable and has good reliability. Also, among the skeletons having a π-electron rich heteroaromatic ring, an acridine skeleton, a phenoxazine skeleton, a thiophene skeleton, A furan skeleton, and a pyrrole skeleton are stable and have good reliability, so it is preferable to have any one or more selected from among these skeletons. As the pyrrole skeleton, indole Skeleton, carbazole skeleton, and 3-(9-phenyl-9H-carbazol-3-yl)-9H-carbazole skeleton are particularly preferable. Note that a substance in which a π-electron rich heteroaromatic ring and a π Electron-deficient heteroaromatic rings are directly bonded, the donor property of the π-electron rich heteroaromatic ring and the acceptor property of the π Electron-deficient heteroaromatic rings are both strong, and the difference between the energy level of the singlet excited state and the Energy level of the triplet excited state is small, so it is particularly preferable.

[0231]

[0232] In the light emitting layer 140, it may have a material other than the host material 141 and the guest material 142.

[0232] The material that can be used for the light emitting layer 140 is not particularly limited, but for example, anthracene Derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives, condensed polycyclic aromatic compounds such as dibenzo[g, p]chrysene derivatives, etc., specifically, 9,10-diphenylanthracene (abbreviation: DPAnth), 6,12-dimethoxy-5,11-diphenyl Chrysene, 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: D ​(PPA), 9,10-bis(2-naphthyl)anthracene (abbreviation: DNA), 2-tert -butyl-9,10-bis(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9, 9'-bianthryl (abbreviation: BANT), 9,9'-(stilbene-3,3'-diyl) diphenanthrene (abbreviation: DPNS), 9,9'-(stilbene-4,4'-diyl)di phenanthrene (abbreviation: DPNS2), 1,3,5-tri(1-pyrenyl)benzene (abbreviation : TPB3), etc. can be mentioned. Also, from among these and known substances, one or more substances having a singlet excitation energy level or a triplet excitation energy level higher than the excitation energy level of the guest material 142 may be selected and used.

[0233] Further, for example, a compound having a heteroaromatic ring skeleton such as an oxadiazole derivative can be used in the light-emitting layer 1 40. Specifically, for example, 2-(4-biphenylyl)-5-(4 -tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1 ,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole- 2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxa diazole-2-yl)phenyl]-9H-carbazole (abbreviation: CO11), 4, 4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) and other heteroaromatic compounds can be mentioned.

[0234] Further, a metal complex having a heteroaromatic ring (for example, a zinc and aluminum-based metal complex) etc. can be used in the light-emitting layer 140. For example, a quinoline ligand, a benzoquinoline ligand, Examples of the metal complex include an oxazole ligand or a thiazole ligand. Specifically for example, tris(8-hydroxyquinolinato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-hydroxyquinolinato)aluminum(III) (abbreviation: Almq 3 ) , bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeB q 2 ), bis(2-methyl-8-hydroxyquinolinato)(4-phenylphenolato)aluminum (III) (abbreviation: BAlq), bis(8-hydroxyquinolinato)zinc(II) (abbreviation: Zn q), etc. Metal complexes having a quinoline skeleton or a benzoquinoline skeleton are exemplified. Also in addition, bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: Z nPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: Z nBTZ), etc., metal complexes having an oxazole-based or a thiazole-based ligand can also be used .

[0235] Note that the light-emitting layer 140 can also be composed of two or more layers. For example, when the first light-emitting layer and the second light-emitting layer are laminated in order from the hole transport layer side to form the light-emitting layer 140, a substance having hole transporting property is used as the host material of the first light-emitting layer, and a substance having electron transporting property is used as the host material of the second light-emitting layer . There is also a configuration in which a substance having hole transporting property is used as the host material of the first light-emitting layer and a substance having electron transporting property is used as the host material of the second light-emitting layer . Also, the light-emitting materials of the first light-emitting layer and the second light-emitting layer may be the same material or different materials, and may be materials having a function of emitting light of the same color , or may be materials having a function of emitting light of different colors. A light-emitting material having a function of emitting light of different colors from each other is provided in the two light-emitting layers By using each of them, a plurality of light emissions can be obtained simultaneously. In particular, it is preferable to select a light-emitting material to be used in each light-emitting layer so that the light emissions exhibited by the two-layer light-emitting layer become white. For the light emission exhibited by , it is preferable to select a light-emitting material to be used in each light-emitting layer so that it becomes white.

[0236] Note that the light-emitting layer 140 can be formed by methods such as a vapor deposition method (including a vacuum vapor deposition method), an inkjet method, a coating method, and gravure printing. In addition to the materials described above, it may also have an inorganic compound or a polymer compound (such as an oligomer, a dendrimer, a polymer, etc.) such as a quantum dot. For the light emission exhibited by , it is preferable to select a light-emitting material to be used in each light-emitting layer so that it becomes white. Note that the light-emitting layer 140 can be formed by methods such as a vapor deposition method (including a vacuum vapor deposition method), an inkjet method, a coating method, and gravure printing. In addition to the materials described above, it may also have an inorganic compound or a polymer compound (such as an oligomer, a dendrimer, a polymer, etc.) such as a quantum dot. It may also have an inorganic compound or a polymer compound (such as an oligomer, a dendrimer, a polymer, etc.) such as a quantum dot.

[0237] ≪Hole Injection Layer≫ The hole injection layer 111 has a function of promoting hole injection by reducing the hole injection barrier from one of the pair of electrodes (electrode 101 or electrode 102), and is formed by, for example, a transition metal oxide, a phthalocyanine derivative, or an aromatic amine. Examples of the transition metal oxide include molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide. Examples of the phthalocyanine derivative include phthalocyanine and metal phthalocyanine. Examples of the aromatic amine include benzidine derivatives and phenylenediamine derivatives. Polymer compounds such as polythiophene and polyaniline can also be used, and for example, poly(ethylenedioxythiophene) / poly(styrenesulfonic acid), which is a self-doped polythiophene, is a representative example. For the light emission exhibited by , it is preferable to select a light-emitting material to be used in each light-emitting layer so that it becomes white. The hole injection layer 111 has a function of promoting hole injection by reducing the hole injection barrier from one of the pair of electrodes (electrode 101 or electrode 102), and is formed by, for example, a transition metal oxide, a phthalocyanine derivative, or an aromatic amine. Examples of the transition metal oxide include molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide. Examples of the phthalocyanine derivative include phthalocyanine and metal phthalocyanine. Examples of the aromatic amine include benzidine derivatives and phenylenediamine derivatives. Polymer compounds such as polythiophene and polyaniline can also be used, and for example, poly(ethylenedioxythiophene) / poly(styrenesulfonic acid), which is a self-doped polythiophene, is a representative example. Examples of the transition metal oxide include molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide. Examples of the phthalocyanine derivative include phthalocyanine and metal phthalocyanine. Examples of the aromatic amine include benzidine derivatives and phenylenediamine derivatives. Polymer compounds such as polythiophene and polyaniline can also be used, and for example, poly(ethylenedioxythiophene) / poly(styrenesulfonic acid), which is a self-doped polythiophene, is a representative example. Polymer compounds such as polythiophene and polyaniline can also be used, and for example, poly(ethylenedioxythiophene) / poly(styrenesulfonic acid), which is a self-doped polythiophene, is a representative example. For the light emission exhibited by , it is preferable to select a light-emitting material to be used in each light-emitting layer so that it becomes white.

[0238] As the hole injection layer 111, a layer having a composite material of a hole-transporting material and a material exhibiting electron-accepting properties with respect to the hole-transporting material can also be used. Alternatively, a laminate of a layer containing a material exhibiting electron-accepting properties and a layer containing a hole-transporting material may be used. Between these materials, in a steady state or during an electric As the hole injection layer 111, a layer having a composite material of a hole-transporting material and a material exhibiting electron-accepting properties with respect to the hole-transporting material can also be used. Alternatively, a laminate of a layer containing a material exhibiting electron-accepting properties and a layer containing a hole-transporting material may be used. Between these materials, in a steady state or during an electric current, a charge transfer may occur between them. It is possible to transfer charges in the presence of a boundary. As materials exhibiting electron accepting properties, there are organic acceptors such as quinodimethane derivatives, chloranil derivatives, hexaazatriphenylene derivatives, etc. Specific examples include compounds having an electron-withdrawing group (halogen group or cyano group), such as 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F -TCNQ), chloranil, 2,3,6,7, 10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN). Furthermore, transition metal oxides, for example, oxides of metals from Group 4 to Group 8, can be used. 4 Specifically, they are vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, rhenium oxide, etc. Among them, molybdenum oxide is preferred because it is stable even in the air, has low hygroscopicity, and is easy to handle. For the hole transporting material, a material with higher hole transporting property than electrons can be used, and it is preferably a material having a hole mobility of 1 × 10 cm / Vs or more. Specifically, aromatic amines, carbazole derivatives, aromatic hydrocarbons, stilbene derivatives, etc., which were mentioned as hole transporting materials that can be used in the light emitting layer 140, can be used.

[0239] Moreover, the hole transporting material may be a polymer compound. × 10 -6 cm 2 / Vs or more. Specifically, aromatic amines, carbazole derivatives, aromatic hydrocarbons, stilbene derivatives, etc., which were mentioned as hole transporting materials that can be used in the light emitting layer 140, can be used. Moreover, the hole transporting material may be a polymer compound.

[0240] In addition, other hole transporting materials include aromatic hydrocarbons. For example, 2-tert -butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 2- tert-Butyl-9,10-di(1-naphthyl)anthracene, 9,10-bis(3, 5-diphenylphenyl)anthracene (abbreviation: DPPA), 2-tert-butyl-9 ,10-bis(4-phenylphenyl)anthracene (abbreviation: t-BuDBA), 9,1 0-di(2-naphthyl)anthracene (abbreviation: DNA), 9,10-diphenylanthra cene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation: t-BuAn th), 9,10-bis(4-methyl-1-naphthyl)anthracene (abbreviation: DMNA) 、2-tert-butyl-9,10-bis[2-(1-naphthyl)phenyl]anthracene ne, 9,10-bis[2-(1-naphthyl)phenyl]anthracene, 2,3,6,7- tetramethyl-9,10-di(1-naphthyl)anthracene, 2,3,6,7-tetram hyl-9,10-di(2-naphthyl)anthracene, 9,9'-bianthryl, 10,1 0'-diphenyl-9,9'-bianthryl, 10,10'-bis(2-phenylphenyl yl)-9,9'-bianthryl, 10,10'-bis[(2,3,4,5,6-penta enyl)phenyl]-9,9'-bianthryl, anthracene, tetracene, rubrene, perylene, 2,5,8,11-tetra(tert-butyl)perylene and the like can be mentioned. Furthermore, pentacene, coronene, etc. can also be used. Thus, it is more preferable to use an aromatic hydrocarbon having a hole mobility of 1×10 -6 cm 2 / Vs or more and having 14 to 42 carbon atoms.

[0241] Note that the aromatic hydrocarbon may have a vinyl skeleton. An aromatic having a vinyl group Examples of the group of hydrocarbons include, for example, 4,4'-bis(2,2-diphenylvinyl)biphenyl (abbreviation: DPVBi), 9,10-bis[4-(2,2-diphenylvinyl)phenyl] anthracene (abbreviation: DPVPA), etc.

[0242] Also, 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]f enyl}dibenzofuran (abbreviation: mmDBFFLBi-II), 4,4',4''-(ben zene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II), 1,3,5-tri(dibenzothiophen-4-yl)-benzene (abbreviation: DBT3P-I I), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl) phenyl]dibenzothiophene (abbreviation: DBTFLP-III), 4-[4-(9-phe nyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbre viation: DBTFLP-IV), 4-[3-(triphenylene-2-yl)phenyl]diben zothiophene (abbreviation: mDBTPTp-II), etc., such as thiophene compounds, furan compounds, f luorene compounds, triphenylene compounds, phenanthrene compounds, etc., can be used. Among the above-mentioned compounds, compounds having a pyrrole skeleton, a furan skeleton, a thiophene skeleton, or an aromatic amine skeleton are stable and have good reliability, and are preferable. Also, the compounds having such a skeleton have high hole-transporting properties and contribute to reducing the driving voltage.

[0243] <<Hole-transporting layer>> The hole-transporting layer 112 is a layer containing a hole-transporting material, and the hole-transporting materials exemplified as the material of the hole-injecting layer 111 can be used. The hole-transporting layer 112 is provided on the hole-injecting layer 111 and Since it has a function of transporting the injected holes to the light-emitting layer 140, the HOM of the hole injection layer 111 preferably has a HOMO level that is the same as or close to the O level.

[0244] Also, it is preferably a substance having a hole mobility of 1×10 -6 cm 2 / Vs or more. However, as long as it is a substance with higher hole transportability than electrons, substances other than these may be used. . Note that the layer containing a substance with high hole transportability may be not only a single layer, but also two or more layers of the layers made of the above substances stacked. .

[0245] ≪Electron transport layer≫ The electron transport layer 118 has a function of transporting the electrons injected from the other of the pair of electrodes (electrode 101 or electrode 102) through the electron injection layer 119 to the light-emitting layer 140. As the electron transport material , a material with higher electron transportability than holes can be used, and it is preferably a material having an electron mobility of 1×10 -6 cm 2 / Vs or more. As the compound (material having electron transportability) that easily accepts electrons, a π-electron deficient type heteroaromatic compound such as a nitrogen-containing heteroaromatic compound or a metal complex can be used. As other specific examples, the pyridine derivatives, bipyridine derivatives mentioned as the electron transport materials that can be used for the light-emitting layer 1 40, pyrimidine derivatives, triazine derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, phenanthroline derivatives, triazole derivatives, benzimidazole derivatives, ox adiazole derivatives, etc. can be mentioned. Also, it is preferably a substance having an electron mobility of 1×10 / Vs or more. Note that it is a substance with higher electron transportability than holes. -6 cm 2 / Vs or more. Otherwise, substances other than those described above may be used as the electron transport layer. Also, the electron transport layer 118 may be not only a single layer but also two or more layers of the above substances stacked.

[0246] In addition, metal complexes having a heteroaromatic ring are exemplified. For example, metal complexes having a quinoline ligand, a benzoquinoline ligand, an oxazole ligand, or a thiazole ligand are exemplified. Specifically, for example, tris(8-quinolinolato)aluminum(III) (abbreviation :Alq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq 3 ), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) ( 2 ) (abbreviation: BeBq ), bis(2-methyl-8-quinolinolato)(4-phenylphenolato 2 )aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) ) (abbreviation: Znq), etc., metal complexes having a quinoline skeleton or a benzoquinoline skeleton are exemplified. In addition, metal complexes having an oxazole-based or thiazole-based ligand such as bis[2-(2-benzoxazolyl)phenolato]zinc(II ) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II ) (abbreviation: ZnBTZ), etc. can also be used. In addition, a layer for controlling the movement of electron carriers may be provided between the electron transport layer 118 and the light-emitting layer 140. This is a layer in which a small amount of a substance having high electron trap properties is added to a material having high electron transport properties as described above, and by suppressing the movement of electron carriers, it becomes possible to adjust the carrier balance. Such a configuration is such that the electron transport property of the electron transport material is positive.

[0247] ​​​Problems that occur when the hole transporting property of the hole transporting material is significantly higher than that of the hole transporting material (e.g., shortening of device life). It is highly effective in suppressing

[0248] ≪Electron injection layer≫ The electron injection barrier at the interface between the electron injection layer 119 and the electrode 102 is reduced, thereby For example, Group 1 metals, Group 2 metals, or oxides thereof, halo In addition, the above-mentioned electron transport material and the corresponding A composite material of a material that exhibits electron donating properties to the electron donor can also be used. Examples of the metal include Group 1 metals, Group 2 metals, and oxides thereof. Specifically, lithium fluoride (LiF), sodium fluoride (NaF), and cesium fluoride (CsF), calcium fluoride (CaF 2 ), lithium oxide (LiO x ) etc. The alkali metals, alkaline earth metals, or compounds thereof can be used. Erbium fluoride (ErF 3 In addition, rare earth metal compounds such as An electride may be used for the electron injection layer 119. Examples of the electride include Examples include a substance in which a high concentration of electrons are added to a mixed oxide of calcium and aluminum. In addition, the electron injecting layer 119 may be formed using a substance that can be used in the electron transporting layer 118 .

[0249] In addition, the electron injection layer 119 is made of a composite material obtained by mixing an organic compound and an electron donor. Such composite materials may be made by adding electrons to an organic compound via an electron donor. In this case, the organic compound is , it is preferably a material excellent in transporting generated electrons. Specifically, for example, the substances (such as metal complexes and heteroaromatic compounds) constituting the electron transport layer 118 can be used . As the electron donor, any substance that shows electron-donating properties to organic compounds may be used. Specifically , alkali metals, alkaline earth metals, and rare earth metals are preferable, and examples include lithium, sodium , cesium, magnesium, calcium, erbium, ytterbium, etc. . Also, alkali metal oxides and alkaline earth metal oxides are preferable, and examples include lithium oxide, cal cium oxide, barium oxide, etc. Further, Lewis bases such as magnesium oxide can also be used. In addition, organic compounds such as tetrathiafulvalene (abbreviation: TTF) can also be used.

[0250] Note that the above-described light-emitting layer, hole injection layer, hole transport layer, electron transport layer, and electron injection layer can be formed by methods such as vapor deposition (including vacuum vapor deposition), inkjet method, coating method, gravure printing, etc. . Also, in addition to the above-described materials, inorganic compounds such as quantum dots and high molecular weight compounds (such as oligomers, dendrimers, and polymers) may be used for the above-described light-emitting layer, hole injection layer, hole transport layer, electron transport layer, and electron injection layer.

[0251] ≪Quantum Dots≫ Quantum dots are semiconductor nanocrystals with sizes ranging from several nm to several tens of nm, and are composed of about 1 × 10 3 to 1 × 10 6 atoms. Since quantum dots shift in energy depending on their size, even quantum dots composed of the same substance have different emission wavelengths depending on their size. Therefore, by changing the size of the quantum dots used, emission can be easily achieved. wavelength can be easily changed. The wavelength can be changed.

[0252] In addition, since quantum dots have a narrow peak width in the emission spectrum, it is possible to obtain light emission with good color purity. Furthermore, the theoretical internal quantum efficiency of quantum dots is said to be almost 100%, which is much higher than 25% of organic compounds that exhibit fluorescence emission and is equivalent to that of organic compounds that exhibit phosphorescence emission. From this, it is possible to obtain a light-emitting device with high luminous efficiency by using quantum dots as a light-emitting material. Moreover, since quantum dots, which are inorganic materials, are also excellent in their inherent stability, it is possible to obtain a preferable light-emitting device from the perspective of lifespan. From this, it is possible to obtain a light-emitting device with high luminous efficiency by using quantum dots as a light-emitting material. Moreover, since quantum dots, which are inorganic materials, are also excellent in their inherent stability, it is possible to obtain a preferable light-emitting device from the perspective of lifespan. From this, it is possible to obtain a light-emitting device with high luminous efficiency by using quantum dots as a light-emitting material. Moreover, since quantum dots, which are inorganic materials, are also excellent in their inherent stability, it is possible to obtain a preferable light-emitting device from the perspective of lifespan. From this, it is possible to obtain a light-emitting device with high luminous efficiency by using quantum dots as a light-emitting material. Moreover, since quantum dots, which are inorganic materials, are also excellent in their inherent stability, it is possible to obtain a preferable light-emitting device from the perspective of lifespan. can be obtained.

[0253] Examples of materials constituting quantum dots include Group 14 elements, Group 15 elements, Group 16 elements, compounds composed of plural Group 14 elements, compounds of elements belonging to Group 4 to Group 14 and Group 16 elements, compounds of Group 2 elements and Group 16 elements, compounds of Group 13 elements and Group 15 elements, compounds of Group 13 elements and Group 17 elements, compounds of Group 14 elements and Group 15 elements, compounds of Group 11 elements and Group 17 elements, iron oxides, titanium oxides, chalcogenide spinels, semiconductor clusters, and the like. Examples of materials constituting quantum dots include Group 14 elements, Group 15 elements, Group 16 elements, compounds composed of plural Group 14 elements, compounds of elements belonging to Group 4 to Group 14 and Group 16 elements, compounds of Group 2 elements and Group 16 elements, compounds of Group 13 elements and Group 15 elements, compounds of Group 13 elements and Group 17 elements, compounds of Group 14 elements and Group 15 elements, compounds of Group 11 elements and Group 17 elements, iron oxides, titanium oxides, chalcogenide spinels, semiconductor clusters, and the like. Examples of materials constituting quantum dots include Group 14 elements, Group 15 elements, Group 16 elements, compounds composed of plural Group 14 elements, compounds of elements belonging to Group 4 to Group 14 and Group 16 elements, compounds of Group 2 elements and Group 16 elements, compounds of Group 13 elements and Group 15 elements, compounds of Group 13 elements and Group 17 elements, compounds of Group 14 elements and Group 15 elements, compounds of Group 11 elements and Group 17 elements, iron oxides, titanium oxides, chalcogenide spinels, semiconductor clusters, and the like. Examples of materials constituting quantum dots include Group 14 elements, Group 15 elements, Group 16 elements, compounds composed of plural Group 14 elements, compounds of elements belonging to Group 4 to Group 14 and Group 16 elements, compounds of Group 2 elements and Group 16 elements, compounds of Group 13 elements and Group 15 elements, compounds of Group 13 elements and Group 17 elements, compounds of Group 14 elements and Group 15 elements, compounds of Group 11 elements and Group 17 elements, iron oxides, titanium oxides, chalcogenide spinels, semiconductor clusters, and the like. Examples of materials constituting quantum dots include Group 14 elements, Group 15 elements, Group 16 elements, compounds composed of plural Group 14 elements, compounds of elements belonging to Group 4 to Group 14 and Group 16 elements, compounds of Group 2 elements and Group 16 elements, compounds of Group 13 elements and Group 15 elements, compounds of Group 13 elements and Group 17 elements, compounds of Group 14 elements and Group 15 elements, compounds of Group 11 elements and Group 17 elements, iron oxides, titanium oxides, chalcogenide spinels, semiconductor clusters, and the like. Examples of materials constituting quantum dots include Group 14 elements, Group 15 elements, Group 16 elements, compounds composed of plural Group 14 elements, compounds of elements belonging to Group 4 to Group 14 and Group 16 elements, compounds of Group 2 elements and Group 16 elements, compounds of Group 13 elements and Group 15 elements, compounds of Group 13 elements and Group 17 elements, compounds of Group 14 elements and Group 15 elements, compounds of Group 11 elements and Group 17 elements, iron oxides, titanium oxides, chalcogenide spinels, semiconductor clusters, and the like.

[0254] Specifically, cadmium selenide, cadmium sulfide, cadmium telluride, lead selenide, zinc oxide, zinc sulfide, zinc telluride, mercury sulfide, mercury selenide, mercury telluride, indium arsenide, indium phosphide, gallium arsenide, gallium phosphide, indium nitride, gallium nitride, indium antimonide, gallium antimonide, aluminum phosphide, arsenic Specifically, cadmium selenide, cadmium sulfide, cadmium telluride, lead selenide, zinc oxide, zinc sulfide, zinc telluride, mercury sulfide, mercury selenide, mercury telluride, indium arsenide, indium phosphide, gallium arsenide, gallium phosphide, indium nitride, gallium nitride, indium antimonide, gallium antimonide, aluminum phosphide, arsenic Specifically, cadmium selenide, cadmium sulfide, cadmium telluride, lead selenide, zinc oxide, zinc sulfide, zinc telluride, mercury sulfide, mercury selenide, mercury telluride, indium arsenide, indium phosphide, gallium arsenide, gallium phosphide, indium nitride, gallium nitride, indium antimonide, gallium antimonide, aluminum phosphide, arsenic Specifically, cadmium selenide, cadmium sulfide, cadmium telluride, lead selenide, zinc oxide, zinc sulfide, zinc telluride, mercury sulfide, mercury selenide, mercury telluride, indium arsenide, indium phosphide, gallium arsenide, gallium phosphide, indium nitride, gallium nitride, indium antimonide, gallium antimonide, aluminum phosphide, arsenic Aluminum, aluminum antimonide, lead selenide, lead telluride, lead sulfide, selenium Indium, indium telluride, indium sulfide, gallium selenide, arsenic sulfide, selenium Arsenic, tellurium arsenide, antimony sulfide, antimony selenide, antimony telluride, Bismuth sulfide, bismuth selenide, bismuth telluride, silicon, silicon carbide, germanium Tin, selenium, tellurium, boron, carbon, phosphorus, boron nitride, boron phosphide, boron arsenide Aluminum nitride, aluminum sulfide, barium sulfide, barium selenide, barium telluride, Calcium sulfide, calcium selenide, calcium telluride, beryllium sulfide, Beryllium selenide, beryllium telluride, magnesium sulfide, magnesium selenide, Germanium sulfide, germanium selenide, germanium telluride, tin sulfide, tin selenide Tin telluride, lead oxide, copper fluoride, copper chloride, copper bromide, copper iodide, copper oxide, copper selenide, acid Nickel oxide, cobalt oxide, cobalt sulfide, iron oxide, iron sulfide, manganese oxide, molybdenum sulfide Vanadium oxide, tungsten oxide, tantalum oxide, titanium oxide, zirconium oxide Silicon nitride, germanium nitride, aluminum oxide, barium titanate, selenium and zinc Lead and cadmium compounds, indium, arsenic and phosphorus compounds, cadmium, selenium and sulfur Compounds of cadmium, selenium and tellurium, indium, gallium and arsenic compounds Compounds of indium, gallium and selenium, indium, selenium and sulfur compounds, copper and indium Compounds of sulfur, and combinations thereof, etc. can be mentioned, but not limited to these. Also, so-called alloy-type quantum dots in which the composition is represented by an arbitrary ratio can be used For example, alloy-type quantum dots of cadmium, selenium and sulfur change the content ratio of the elements ​ Since the emission wavelength can be changed by making the change, it is one of the effective means for obtaining blue emission. It is one of them.

[0255] Examples of the quantum dot structure include core type, core-shell type, core-multiple shell type, etc., and any of them may be used. However, by forming a shell with another inorganic material having a wider band gap covering the core, defects and dangling bonds existing on the nanocrystal surface can be reduced. As a result, since the quantum efficiency of emission is greatly improved, it is preferable to use core-shell type or core-multiple shell type quantum dots. Examples of the shell material include zinc sulfide and zinc oxide.

[0256] In addition, since quantum dots have a high ratio of surface atoms, they have high reactivity and tend to agglomerate. Therefore, it is preferable that a protective agent is attached or a protective group is provided on the surface of the quantum dots. By attaching the protective agent or providing the protective group, agglomeration can be prevented and the solubility in a solvent can be increased. It is also possible to reduce the reactivity and improve the electrical stability. Examples of the protective agent (or protective group) include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, and polyoxyethylene oleyl ether, trialkylphosphines such as tripropylphosphine, tributylphosphine, trihexylphosphine, and trioctylphosphine, and polyoxyethylene alkyl phenyl ethers such as polyoxyethylene n-octyl phenyl ether and polyoxyethylene n-nonyl phenyl ether. Tellurides, tri(n-hexyl)amine, tri(n-octyl)amine, tri(n-decyl ) amines and other tertiary amines, tripropylphosphine oxide, tributylphosphine oxide, trihexylphosphine oxide, trioctylphosphine oxide, tride cylphosphine oxide and other organophosphorus compounds, polyethylene glycol dilaurate, po lyethylene glycol distearate and other polyethylene glycol diesters, also, organic nitrogen compounds such as nitrogen-containing aromatic compounds such as pyridine, lutidine, collidine, quinolines, etc. , aminoalkanes such as hexylamine, octylamine, decylamine, dodecylamine, tetradecylami ne, hexadecylamine, octadecylamine, etc., dialkyl sulfides such as dibutyl sulfi de, dialkyl sulfoxides such as dimethyl sulfoxide and dibutyl sulfoxide, organic sulfur compounds such as sulfur-containing aromatic compounds such as thiophene, palmi tic acid, stearic acid, oleic acid and other higher fatty acids, alcohols, sorbitan fatty acid es ters, fatty acid-modified polyesters, tertiary amine-modified polyurethanes, polyethylene im nes, etc. are exemplified.

[0257] Since the bandgap of quantum dots increases as their size decreases, the size is adjusted appropriately so that light of a desired wavelength can be obtained. As the size of the crystal decreases, the emission of the quantum dots shifts to the blue side, that is, to the high-energy side. Therefore, by changing the size of the quantum dots, the emission wavelength can be adjusted over the wavelength ranges of the ultraviolet region, visible region, and infrared region spectra. The size (diameter) of the quantum dots is usually preferably in the range of 0.5 nm to 20 nm, more preferably 1 nm to 10 nm, and is often used well. ​​​​​This is the case. Note that the narrower the size distribution of the quantum dots, the narrower the emission spectrum becomes , and emission with good color purity can be obtained. Further, the shape of the quantum dots is not particularly limited, and they may be spherical, rod-shaped, disk-shaped, or other shapes. Note that quantum rods, which are rod-shaped quantum dots, have the function of exhibiting light with directivity. Therefore, by using quantum rods as the light-emitting material , a light-emitting device with better external quantum efficiency can be obtained.

[0258] By the way, in many cases in an organic EL device, the light-emitting material is dispersed in a host material to suppress concentration quenching of the light-emitting material and improve the luminous efficiency. The host material needs to be a material having a singlet excitation energy level or a triplet excitation energy level higher than that of the light-emitting material . In particular, when a blue phosphorescent material is used as the light-emitting material, a host material having a triplet excitation energy level higher than that and excellent in terms of lifetime is required, and its development is extremely difficult . Here, since quantum dots can maintain the luminous efficiency even when forming the light-emitting layer only with quantum dots without using a host material , a preferable light-emitting device can be obtained from the viewpoint of lifetime also in this respect. When forming the light-emitting layer only with quantum dots, the quantum dots are preferably of a core- shell structure (including a core-multishell structure).

[0259] When using quantum dots as the light-emitting material of the light-emitting layer, the film thickness of the light-emitting layer is 3 nm to 100 n m, preferably 10 nm to 100 nm, and the content of the quantum dots in the light-emitting layer is 1 to 1 00 vol%. However, it is preferable to form the light-emitting layer only with quantum dots. Note that when forming a light-emitting layer in which the quantum dots are dispersed in a host as the light-emitting material, the host material Disperse quantum dots or dissolve the host material and quantum dots in a suitable liquid medium or disperse them and form them by a wet process (spin coating method, casting method, die coating method, blade coating method, roll coating method, inkjet method, printing method, spray coating method, curtain co ating method, Langmuir-Blodgett method, etc.). For the light-emitting layer using a phosphorescent light-emitting material in addition to the above wet process, a vacuum evaporation method can also be suitably used as well.

[0260] Examples of the liquid medium used in the wet process include ketones such as methyl ethyl ketone and cyclohe xanone, fatty acid esters such as ethyl acetate, halogenated hydrocarbons such as dichlorobenzene aromatic hydrocarbons such as toluene, xylene, mesitylene, cyclohexylbenzene, aliphatic hydrocarbons such as cyclohexane, decalin, dodecane, and organic solvents such as dimethylform amide (DMF) and dimethyl sulfoxide (DMSO) can be used.

[0261] ≪Pair of electrodes≫ The electrodes 101 and 102 have the function of the anode or cathode of the light-emitting device. The electrodes 101 and 102 can be formed using metals, alloys, conductive compounds, and mixtures or laminates thereof and the like.

[0262] It is preferable that one of the electrode 101 or the electrode 102 is formed of a conductive material having a function of reflecting light. Examples of the conductive material include aluminum (Al) or an alloy containing Al and the like. Examples of the alloy containing Al include an alloy containing Al and L (L represents one or more of titanium (Ti), neodymi um (Nd), nickel (Ni), and lanthanum (La)) and the like. Examples include alloys such as those containing Al and Ti, or alloys containing Al, Ni, and La. Aluminum has a low resistance value and a high light reflectivity. Also, aluminum is abundant in the earth's crust and is inexpensive, so the manufacturing cost of a light-emitting device using aluminum can be reduced. Further, an alloy containing one or more of silver (Ag), or Ag and N (where N represents yttrium (Y), Nd, magnesium (Mg), ytterbium (Yb), Al, Ti, gallium (Ga), zinc (Zn), indium (In), tungsten (W), manganese (Mn), tin (Sn), iron (Fe), Ni, copper (Cu), palladium (Pd), iridium (Ir ), or gold (Au)) may be used. Examples of alloys containing silver include alloys containing silver, palladium, and copper, alloys containing silver and copper, alloys containing silver and magnesium , alloys containing silver and nickel, alloys containing silver and gold, alloys containing silver and ytterbium , etc. Additionally, transition metals such as tungsten, chromium (Cr), molybdenum (Mo

[0263] Also, the light emission obtained from the light-emitting layer is extracted through one or both of the electrodes 101 and 102. Therefore, at least one of the electrodes 101 or 102 is preferably formed of a conductive material having a function of transmitting light. The conductive material has a visible light transmittance of 40% or more and 100% or less, preferably 60% or more and 100% or less, and its resistivity is 1×10 Ω·cm or less.

[0264] -2 Further, the electrodes 101 and 102 have a function of transmitting light and a function of reflecting light. ​​​It may be formed of a conductive material. As the conductive material, the reflectance of visible light is 20 % or more and 80% or less, preferably 40% or more and 70% or less, and its resistivity is 1×10 -2 Ω·cm or less. For example, it can be formed by using one or more of a conductive metal, alloy, conductive compound, etc. Specifically, for example, indium tin oxide (Indium Tin Oxide, hereinafter ITO), silicon or indium tin oxide containing silicon oxide (abbreviation: ITSO), indium oxide - zinc oxide (Indi um Zinc Oxide), indium tin oxide containing titanium, indium -titanium oxide, indium oxide containing tungsten oxide and zinc oxide, etc. of metal oxides can be used. In addition, a metal thin film having a degree of light transmission (preferably a thickness of 1 nm or more and 30 n m or less) can be used. As the metal, for example, Ag, or alloys such as Ag and Al, Ag and Mg, Ag and Au, Ag and Yb, etc. can be used.

[0265] In the present specification, etc., a material having a function of transmitting light may be any material having a function of transmitting visible light and having conductivity. For example, in addition to the oxide conductors represented by the above-mentioned ITO, it includes oxide semiconductors or organic conductors containing organic substances. Examples of organic conductors containing organic substances include composite materials formed by mixing an organic compound and an electron donor (donor), composite materials formed by mixing an organic compound and an electron acceptor (acceptor), etc. In addition, inorganic carbon-based materials such as graphene may be used. Also, the resistivity of the material is preferably 1×10 Ω·cm or less, more preferably 1×10 Ω·cm or less, and even more preferably 1×10 Ω·cm or less. Preferably, it is 1×10 5 Ω·cm or less, and more preferably 1×10 4 Ω·cm The following applies.

[0266] Also, by laminating a plurality of the above materials, one or both of the electrodes 101 and 102 may be formed.

[0267] Further, in order to improve the light extraction efficiency, in contact with an electrode having a function of transmitting light, a material having a refractive index higher than that of the electrode may be formed. Such a material may be any material having a function of transmitting visible light, and may or may not be a conductive material. For example, in addition to the above-described oxide conductors, oxide semiconductors and organic substances may be mentioned. Examples of organic substances include materials exemplified for the light emitting layer, hole injection layer, hole transport layer, electron transport layer, or electron injection layer. Also, inorganic carbon-based materials and metal thin films that allow light to pass through can also be used, and a plurality of layers of several nm to several tens of nm may be laminated.

[0268] When the electrode 101 or the electrode 102 functions as a cathode, it preferably has a material with a small work function (3.8 eV or less). For example, elements belonging to Group 1 or Group 2 of the periodic table (alkali metals such as lithium, sodium, cesium, alkaline earth metals such as calcium, strontium, barium, magnesium, etc.), alloys containing these elements (for example, Ag and Mg, Al and Li), rare earth metals such as europium (Eu), Yb, alloys containing these rare earth metals, aluminum, alloys containing silver, etc. can be used.

[0269] Also, when the electrode 101 or the electrode 102 is used as an anode, it is preferable to use a material with a large work function (4. 0 eV or more).

[0270] Further, the electrodes 101 and 102 may be a laminate of a conductive material having a function of reflecting light and a conductive material having a function of transmitting light. In that case, the electrodes 101 and 102 are preferably capable of adjusting the optical distance so as to resonate light of a desired wavelength from each light-emitting layer and enhance the light of the desired wavelength. The film formation methods of the electrodes 101 and 102 may be appropriately used, such as sputtering method, evaporation method, printing method, coating method , MBE (Molecular Beam Epitaxy) method, CVD method, pulsed laser deposition method , ALD (Atomic Layer Deposition) method, etc.

[0271] ≪Substrate≫ Also, the light-emitting element according to one aspect of the present invention may be manufactured on a substrate made of glass, plastic, etc. As the order of manufacturing on the substrate, the layers may be laminated in order from the electrode 101 side or in order from the electrode 102 side. As the substrate on which the light-emitting element according to one aspect of the present invention can be formed, for example, glass, quartz

[0272] , or plastic can be used. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), and examples include plastic substrates made of polycarbonate , polyarylate, etc. Also, a film,

[0273] an inorganic vapor deposition film, etc. can also be used. As long as it functions as a support in the manufacturing process of the light-emitting element and the optical element, other materials may be used. Alternatively, as long as it has a function of protecting the light-emitting element and the optical element, it may be used.

[0274] ​​​​​​​​​For example, in this specification or the like, a light-emitting element can be formed using various substrates. . The type of the substrate is not particularly limited. As an example of the substrate, a semiconductor substrate (e.g., a single-crystal substrate or a silicon substrate), an SOI substrate, a glass substrate, a quartz substrate, a plastic substrate, a metal substrate, a stainless-steel substrate, a substrate having a stainless-steel foil, a tungsten substrate, a substrate having a tungsten foil, a flexible substrate, a bonded film, a paper containing fibrous materials, or a base film and the like are available. As an example of the glass substrate, there are barium borosilicate glass, aluminoborosilicate glass, or soda-lime glass and the like. Examples of the flexible substrate, the bonded film, the base film and the like include the following. For example, plastics typified by polyethylene terephthalate (PET), polyethylene naphthalate (PEN) , polyethersulfone (PES), and polytetrafluoroethylene (PTFE) are available. Or, as an example, there are resins such as acrylic. Or there are, for example, polypropylene, polyester, polyvinyl fluoride, or polyvinyl chloride and the like. Or, as an example, there are polyamide, polyimide, aramid, epoxy, an inorganic vapor deposition film, or papers and the like.

[0275] Further, a flexible substrate may be used as the substrate, and a light-emitting element may be directly formed on the flexible substrate. Or, a release layer may be provided between the substrate and the light-emitting element. The release layer is used to separate from the substrate after partially or completely completing the light-emitting element thereon and to transfer it to another substrate. At this time, the light-emitting element can be transferred to a substrate with poor heat resistance or a flexible substrate. In addition, for the above-mentioned release layer, for example, a laminated structure of an inorganic film of a tungsten film and a silicon oxide film It is possible to use a configuration in which a resin film such as polyimide is formed on a substrate or the like.

[0276] That is, a light-emitting element is formed using a certain substrate, and then the light-emitting element is transferred to another substrate. The light-emitting element may be disposed on another substrate. As an example of the substrate to which the light-emitting element is transferred, in addition to the substrate described above, there are a cellophane substrate, a stone substrate, a wood substrate, a cloth substrate (including natural fibers (silk, cotton, hemp), synthetic fibers (nylon, polyurethane, polyester) or regenerated fibers (acetate tow, cupra, rayon, recycled polyester), etc.), a leather substrate, or a rubber substrate. By using these substrates, a light-emitting element that is difficult to break, a light-emitting element with high heat resistance, a light-emitting element with reduced weight, or a light-emitting element with reduced thickness can be obtained.

[0277] Further, on the substrate described above, for example, a field-effect transistor (FET) may be formed, and the light-emitting element 150 may be fabricated on an electrode electrically connected to the FET. Thereby, an active matrix type display device for controlling the driving of the light-emitting element 150 by the FET can be fabricated.

[0278] As described above, the configuration shown in this embodiment can be appropriately combined and used with other embodiments.

[0279] (Embodiment 4) In this embodiment, a light-emitting element having a configuration different from that of the light-emitting element shown in Embodiment 3 will be described below with reference to FIG. 2. In FIG. 2, portions having the same functions as the symbols shown in FIG. 1(A) are given the same hatch pattern, and the symbols may be omitted in some cases. Also, portions having the same functions are given the same reference numerals, and detailed descriptions thereof may be omitted in some cases. ​

[0280] <Configuration Example 2 of Light-Emitting Element> Figure 2 is a schematic cross-sectional view of the light-emitting element 250.

[0281] The light-emitting element 250 shown in Figure 2 has a plurality of light-emitting units (light-emitting unit 106 and light-emitting unit 108) between a pair of electrodes (electrode 101 and electrode 102). Any one of the plurality of light-emitting units preferably has the same configuration as the EL layer 100 shown in Figure 1(A). That is, the light-emitting element 150 shown in Figure 1(A) has one light-emitting unit, and the light-emitting element 250 preferably has a plurality of light-emitting units. In the light-emitting element 250, although electrode 101 functions as an anode and electrode 102 functions as a cathode in the following description, the configuration of the light-emitting element 250 may be reversed.

[0282] Also, in the light-emitting element 250 shown in Figure 2, the light-emitting unit 106 and the light-emitting unit 108 are stacked, and a charge generation layer 1 15 is provided between the light-emitting unit 106 and the light-emitting unit 108. The light-emitting unit 106 and the light-emitting unit 108 may have the same configuration or different configurations. For example, it is preferable to use a configuration similar to the EL layer 100 for the light-emitting unit 108.

[0283] Also, the light-emitting element 250 has a light-emitting layer 120 and a light-emitting layer 170. Further, in addition to the light-emitting layer 170, the light-emitting unit 106 has a hole injection layer 111, a hole transport layer 112, an electron transport layer 113, and an electron injection layer 114. In addition to the light-emitting layer 120, the light-emitting unit 108 has a hole injection layer 116, a hole transport layer 117, an electron transport layer 118, and an electron injection layer 11 9. ​​​​​​

[0284] The light-emitting element 250 is provided in any of the layers of the light-emitting unit 106 and the light-emitting unit 108. It is sufficient that the organic compound contains the organometallic complex according to one embodiment of the present invention. The layer is preferably the light-emitting layer 120 or the light-emitting layer 170 .

[0285] The charge generating layer 115 is formed by adding an acceptor material, which is an electron acceptor, to a hole transport material. Even if the structure is such that a donor substance, which is an electron donor, is added to the electron transport material, Also, both of these configurations may be laminated.

[0286] When the charge generating layer 115 contains a composite material of an organic compound and an acceptor substance, As the composite material, the composite material which can be used for the hole-injection layer 111 shown in Embodiment 3 is used. The organic compounds include aromatic amine compounds, carbazole compounds, aromatic carbon compounds, etc. Various compounds such as hydrogen and polymer compounds (oligomers, dendrimers, polymers, etc.) are used. As an organic compound, a hole mobility of 1×10 -6 cm 2 / Vs However, it is preferable to use a material having a higher hole transporting property than an electron transporting property. Other materials may be used as long as they are compatible with the organic compound and the acceptor material. The material has excellent carrier injection and transport properties, enabling low-voltage and low-current operation. In addition, the anode side surface of the light-emitting unit is in contact with the charge generating layer 115. In this case, the charge generating layer 115 also serves as a hole injection layer or a hole transport layer for the light emitting unit. Therefore, the light-emitting unit does not need to have a hole injection layer or a hole transport layer. This is also acceptable. Alternatively, when the surface on the cathode side of the light-emitting unit is in contact with the charge generation layer 115 the charge generation layer 115 can also serve as the electron injection layer or electron transport layer of the light-emitting unit and thus the light-emitting unit may be configured without an electron injection layer or an electron transport layer which is also acceptable.

[0287] Note that the charge generation layer 115 may be formed as a laminated structure combining a layer containing a composite material of an organic compound and an acceptor material and other layers formed of other materials. For example, it may be formed by combining a layer containing a composite material of an organic compound and an acceptor material and a layer containing one compound selected from electron-donating substances and a compound with high electron transport properties. Further, it may be formed by combining a layer containing a composite material of an organic compound and an acceptor material and a layer containing a transparent conductive film which is also acceptable. Note that the charge generation layer 115 sandwiched between the light-emitting unit 106 and the light-emitting unit 108 only needs to inject electrons into one light-emitting unit and holes into the other light-emitting unit when a voltage is applied between the electrode 101 and the electrode 102. For example, in FIG. 2, when a voltage is applied such that the potential of the electrode 1

[0288] 01 is higher than the potential of the electrode 102, the charge generation layer 115 injects electrons into the light-emitting unit 106 and holes into the light-emitting unit 108 which is also acceptable. Note that the charge generation layer 115 preferably has translucency with respect to visible light (specifically the transmittance of visible light with respect to the charge generation layer 115 is 40% or more) from the viewpoint of light extraction efficiency. Also, the charge generation layer 115 can function even if its conductivity is lower than that of a pair of electrodes (the electrode 101 and the electrode 102).

[0289] Note that the charge generation layer 115 preferably has translucency with respect to visible light (specifically the transmittance of visible light with respect to the charge generation layer 115 is 40% or more) from the viewpoint of light extraction efficiency. Also, the charge generation layer 115 can function even if its conductivity is lower than that of a pair of electrodes (the electrode 101 and the electrode 102).

[0290] By forming the charge generation layer 115 using the above-described material, an increase in the driving voltage in the case where the light-emitting layer is laminated can be suppressed.

[0291] In addition, in FIG. 2, the light-emitting element having two light-emitting units has been described, but the present invention can be similarly applied to a light-emitting element in which three or more light-emitting units are laminated. As shown in the light-emitting element 250, by arranging a plurality of light-emitting units between a pair of electrodes with a charge generation layer interposed therebetween, high-brightness light emission can be enabled while keeping the current density low, and a light-emitting element with a longer lifespan can be realized. Further, a light-emitting element with low power consumption can be realized.

[0292] In addition, in each of the above configurations, as the light-emitting colors exhibited by the guest materials used in the light-emitting unit 106 and the light-emitting unit 108, they may be the same as or different from each other. When the guest material has a function of emitting light of the same color in the light-emitting unit 106 and the light-emitting unit 108, the light-emitting element 250 is preferably a light-emitting element that exhibits a high light-emitting brightness at a low current value. Also, when the guest material has a function of emitting light of different colors in the light-emitting unit 106 and the light-emitting unit 108, the light-emitting element 250 is preferably a multi-color light-emitting element. In this case, since either one or both of the light-emitting layer 120 and the light-emitting layer 170 use a plurality of light-emitting materials having different emission wavelengths, the emission spectrum exhibited by the light-emitting element 250 is light in which emissions having different emission peaks are synthesized, so that the emission spectrum has at least two maximum values.

[0293] ​​​​​​​​​​The above configuration is also suitable for obtaining white light emission. By making the light of the light-emitting layer 120 and the light-emitting layer 170 complementary to each other, white light emission can be obtained. In particular, it is preferable to select a guest material so as to obtain white light emission with high color rendering properties, or light emission having at least red, green, and blue colors.

[0294] Further, in the case of a light-emitting element in which three or more light-emitting units are stacked, the emission colors exhibited by the guest materials used in each light-emitting unit may be the same as or different from each other. When there are a plurality of light-emitting units exhibiting light emission of the same color, these plurality of light-emitting units can emit light with high intensity at a low current value. Such a configuration can be suitably used for adjusting the emission color. In particular, it is suitable for the case where guest materials having different emission efficiencies and different emission colors are used. For example, in the case of having three layers of light-emitting units, two layers of light-emitting units having a fluorescent material of the same color and one layer of a light-emitting unit having a phosphorescent material exhibiting an emission color different from that of the fluorescent material are provided, whereby the emission intensities of fluorescence emission and phosphorescence emission can be adjusted. That is, the intensity of the emission color can be adjusted according to the number of light-emitting units. In the case of a light-emitting element having two layers of such fluorescence-emitting units and one layer of a phosphorescence-emitting unit, a light-emitting element containing two layers of a light-emitting unit containing a blue fluorescent material and one layer of a light-emitting unit containing a yellow phosphorescent material,

[0295] a light-emitting element having two layers of a light-emitting unit containing a blue fluorescent material and one layer of a light-emitting layer unit containing a red phosphorescent material and a green phosphorescent material, or a light-emitting element having two layers of a light-emitting unit containing a blue fluorescent material and one layer of a light-emitting layer unit containing a red phosphorescent material, a yellow phosphorescent material, and a green phosphorescent material, is preferable because white light emission can be efficiently obtained. is preferable because white light emission can be efficiently obtained. is preferable because white light emission can be efficiently obtained. is preferable because white light emission can be efficiently obtained.

[0296] Further, at least one of the light-emitting layer 120 or the light-emitting layer 170 may be further divided into layers, and different light-emitting materials may be contained in each of the divided layers. That is, at least one of the light-emitting layer 120 or the light-emitting layer 170 may be constituted by a plurality of layers of two or more layers. For example, when the first light-emitting layer and the second light-emitting layer are laminated in order from the hole transport layer side to form a light-emitting layer, a material having hole transport properties is used as the host material of the first light-emitting layer, and an electron transport layer is used as the host material of the second light-emitting layer. There are configurations such as using a material having properties. In this case, the light-emitting materials of the first light-emitting layer and the second light-emitting layer may be the same material or different materials, and may be materials having a function of emitting light of the same color or materials having a function of emitting light of different colors. By a configuration having a plurality of light-emitting materials having functions of emitting light of different colors, it is possible to obtain white light emission with high color rendering composed of three primary colors or four or more light-emitting colors. Further, it is preferable that the light-emitting layer of the light-emitting unit 108 has a phosphorescent compound. Among a plurality of units, by applying an organometallic complex according to one aspect of the present invention to at least one unit, it is possible to provide a light-emitting element having good luminous efficiency and reliability. It should be noted that this embodiment can be appropriately combined with other embodiments. (Embodiment 5) In this embodiment, a light-emitting device using the light-emitting element described in Embodiment 3 and Embodiment 4 will be described with reference to FIGS. 3(A) and 3(B).

[0297]

[0298]

[0299]

[0300] ​​​​​​​​​​ FIG. 3(A) is a top view showing a light-emitting device, and FIG. 3(B) is a cross-sectional view taken along line A-B and C-D of FIG. 3(A). This light-emitting device controls the light emission of a light-emitting element, and a drive circuit portion (source-side drive circuit) 601, a pixel portion 602, and a drive circuit portion (gate-side drive circuit) 603 shown by a dotted line are included. Further, 604 is a sealing substrate, 625 is a drying material, and 605 is a sealing material. The inside surrounded by the sealing material 605 is a space 607.

[0301] Note that the routing wiring 608 is a wiring for transmitting signals input to the source-side drive circuit 601 and the gate-side drive circuit 603, and receives a video signal, a clock signal, a start signal, a reset signal, etc. from an FPC (Flexible Printed Circuit) 609 which is an external input terminal. Although only the FPC is illustrated here, a printed wiring board (PWB: Printed Wiring Board) may be attached to this FPC. The light-emitting device in this specification includes not only the light-emitting device main body but also a state in which an FPC or a PWB is attached thereto.

[0302] Next, the cross-sectional structure of the above light-emitting device will be described with reference to FIG. 3(B). A drive circuit portion and a pixel portion are formed on an element substrate 610. Here, one pixel in the source-side drive circuit 601 which is a drive circuit portion and the pixel portion 602 is shown.

[0303] Note that the source-side drive circuit 601 is formed of a CMOS circuit in which an n-channel type TFT 623 and a p-channel type TFT 624 are combined. Further, the drive circuit may be formed of various CMOS circuits, P MOS circuits, and NMOS circuits. Also, in this embodiment, the drive circuit is provided on the substrate​​​​​ It shows the formed integrated driver, but this is not necessarily required, and the drive circuit can be formed externally instead of on the substrate.

[0304] Also, the pixel portion 602 is formed by pixels including a switching TFT 611, a current control 612, and a first electrode 613 electrically connected to its drain. Note that an insulator 614 is formed so as to cover the end portion of the first electrode 613. The insulator 614 can be formed by using a positive photosensitive resin film.

[0305] Also, in order to make the covering property of the film formed on the insulator 614 good, a surface having a curvature is formed at the upper end portion or the lower end portion of the insulator 614. For example, when photosensitive acrylic is used as the material of the insulator 614, it is preferable to provide a curved surface only at the upper end portion of the insulator 614. The radius of curvature of the curved surface is preferably 0.2 μm or more and 0.3 μm or less. Also, as the insulator 614, either a negative type or a positive type photosensitive material can be used.

[0306] An EL layer 616 and a second electrode 617 are respectively formed on the first electrode 613. Here, as the material used for the first electrode 613 that functions as an anode, it is desirable to use a material having a large work function. For example, an ITO film, an indium tin oxide film containing silicon, an indium oxide film containing 2 wt% or more and 20 wt% or less of zinc oxide, a titanium nitride film, a chromium film, a tungsten film, a Zn film, a Pt film, etc. In addition to single-layer films, a laminate of a titanium nitride film and a film mainly composed of aluminum, a three-layer structure of a titanium nitride film, a film mainly composed of aluminum, and a titanium nitride film can be used. Note that when a laminated structure is used, It also has low resistance, enables good ohmic contact, and can further function as an anode. This can be achieved.

[0307] In addition, the EL layer 616 is formed by various methods such as vapor deposition using a vapor deposition mask, inkjet method, spin coating method. As the material constituting the EL layer 616, a low molecular compound or a high molecular compound (including oligomers and dendrimers) may be used.

[0308] Furthermore, as the material used for the second electrode 617 formed on the EL layer 616 and functioning as a cathode, a material with a small work function (Al, Mg, Li, Ca, or their alloys and compounds, such as MgAg, MgIn, AlLi, etc.) is preferably used. When the light generated in the EL layer 616 passes through the second electrode 617, it is preferable to use a stacked layer of a thin metal film with a reduced thickness and a transparent conductive film (ITO, indium tin oxide containing 2 wt% or more and 20 wt% or less of zinc oxide, indium tin oxide containing silicon, zinc oxide (ZnO), etc.) as the second electrode 617. This is good.

[0309] Note that the light-emitting element 618 is formed by the first electrode 613, the EL layer 616, and the second electrode 617. The light-emitting element 618 preferably has the configurations of Embodiment 3 and Embodiment 4. Note that the pixel portion is formed of a plurality of light-emitting elements, and in the light-emitting device according to this embodiment, both a light-emitting element having the configurations described in Embodiment 3 and Embodiment 4 and a light-emitting element having other configurations may be included.

[0310] Furthermore, by bonding the sealing substrate 604 to the element substrate 610 with the sealing material 605, the element ​​​​​​A structure is provided in which a light-emitting element 618 is provided in a space 607 surrounded by a sub-substrate 610, a sealing substrate 604, and a sealing material 605. The space 607 is filled with a filling material and may be filled with a resin or a drying material or both, in addition to the case where an inert gas (such as nitrogen or argon) is filled.

[0311] Note that it is preferable to use an epoxy-based resin or glass frit for the sealing material 605. Also, these materials are desirably materials that do not transmit moisture and oxygen as much as possible. Further, as materials for the sealing substrate 604, in addition to a glass substrate or a quartz substrate, a plastic substrate made of FRP (Fiber R einforced Plastics), PVF (polyvinyl fluoride), polyester or acrylic can be used.

[0312] As described above, a light-emitting device using the light-emitting element described in Embodiment 3 and Embodiment 4 can be obtained.

[0313] <Configuration Example 1 of Light-Emitting Device> FIG. 4 shows an example of a light-emitting device in which a light-emitting element exhibiting white light emission is formed and a coloring layer (color f ilter) is formed as an example of a display device.

[0314] FIG. 4(A) shows a substrate 1001, an underlying insulating film 1002, a gate insulating film 1003, gate electrodes 1006, 1007, 1008, a first interlayer insulating film 1020, a second interlayer insulating film 1021 , a peripheral portion 1042, a pixel portion 1040, a driving circuit portion 1041, a first electrode 102 4W, 1024R, 1024G, 1024B of the light-emitting element, a partition wall 1026, an EL layer 1028, a light-emitting element The second electrode 1029 of the device, a sealing substrate 1031, a sealing material 1032, etc. are shown.

[0315] In addition, in FIGS. 4(A) and 4(B), a colored layer (red colored layer 1034R, green colored layer 10 34G, blue colored layer 1034B) is provided on a transparent substrate 1033. Further, a black layer ( black matrix) 1035 may be further provided. The transparent substrate 1033 provided with the colored layer and the black layer is aligned and fixed to the substrate 1001. Note that the colored layer and the black colored layer are covered with an overcoat layer 1036. In FIG. 4(A), there are a light-emitting layer through which light does not pass through the colored layer to the outside and a light-emitting layer through which light passes through the colored layers of each color to the outside. Since the light that does not pass through the colored layer is white and the light that passes through the colored layer is red, blue, or green, an image can be expressed by four-color pixels.

[0316] In FIG. 4(B), an example in which a red colored layer 1034R, a green colored layer 1034G, and a blue colored layer 103 4B) are formed between the gate insulating film 1003 and the first interlayer insulating film 1020 is shown. As shown in FIG. 4(B), the colored layer may be provided between the substrate 1001 and the sealing substrate 1031.

[0317] In addition, in the light-emitting device described above, a light-emitting device having a structure in which light is extracted from the side of the substrate 1001 on which the TFT is formed (bottom emission type) is used. However, a light-emitting device having a structure in which light is extracted from the side of the sealing substrate 1031 (top emission type) may be used.

[0318] <Configuration Example 2 of Light-Emitting Device> A cross-sectional view of a top emission type light-emitting device is shown in FIG. 5. In this case, a substrate 1001 that does not transmit light can be used. Until a connection electrode that connects the TFT and the anode of the light-emitting element is fabricated, it is formed in the same manner as the bottom emission type light-emitting device. Thereafter, a third interlayer ​​​​​​​​​ An insulating film 1037 is formed to cover the electrode 1022. This insulating film may serve as a planarization layer. The third interlayer insulating film 1037 can be formed using various materials in addition to the same material as the second interlayer insulating film 1021.

[0319] The first lower electrodes 1025W, 1025R, 1025G, and 1025B of the light-emitting element are anodes here, but they can also be cathodes. Also, in the case of a top emission type light-emitting device as shown in FIG. 5, the lower electrodes 1025W, 1025R, 1025G, and 1025B are preferably reflective electrodes. Note that the second electrode 1029 preferably has a function of reflecting light and a function of transmitting light. Further, a microcavity structure is preferably applied between the second electrode 1029 and the lower electrodes 1025W, 1025R, 1025G, and 1025B to have a function of amplifying light of a specific wavelength. The configuration of the EL layer 1028 is set to the configuration as described in Embodiment 3 and Embodiment 4, and an element structure capable of obtaining white light emission is adopted. In FIGS. 4(A), 4(B), and 5, as the configuration of the EL layer capable of obtaining white light emission, it may be realized by using a plurality of light-emitting layers or using a plurality of light-emitting units. Note that the configuration for obtaining white light emission is not limited to these.

[0320] In a top emission structure as shown in FIG. 5, sealing can be performed with a sealing substrate 1031 provided with coloring layers (red coloring layer 1034R, green coloring layer 1034G, blue coloring layer 1034B). A black layer (black matrix) is provided on the sealing substrate 1031 so as to be located between pixels.

[0321] A lix) 1030 may be provided. The colored layers (red colored layer 1034R, green colored layer 1 034G, blue colored layer 1034B) and the black layer (black matrix) 1030 may be covered by an overcoat layer. The sealing substrate 1031 is a substrate having translucency and is used.

[0322] Moreover, in this example, a case of performing full-color display with four colors of red, green, blue, and white is shown, but it is not particularly limited and full-color display may be performed with three colors of red, green, and blue. Also, full-color display may be performed with four colors of red, green, blue, and yellow

[0323] As described above, a light-emitting device using the light-emitting element described in Embodiment 3 and Embodiment 4 can be obtained.

[0324] In addition, this embodiment can be appropriately combined with other embodiments.

[0325] (Embodiment 6) In this embodiment, an electronic device according to one aspect of the present invention will be described.

[0326] Since one aspect of the present invention is a light-emitting element using an organic EL, an electronic device having a flat surface and good luminous efficiency and high reliability can be manufactured. Also, according to one aspect of the present invention, an electronic device having a curved surface and good luminous efficiency and high reliability can be manufactured. Further, by using the organic compound of one aspect of the present invention in the electronic device an electronic device having good luminous efficiency and high reliability can be manufactured.

[0327] Examples of the electronic device include a television device, a desktop or notebook personal computer, a monitor for computers, etc., a digital camera, a digital video camera ​​Mera, digital photo frame, mobile phone, portable game machine, portable information terminal, audio playback Devices, large game machines such as pachinko machines, and the like can be mentioned.

[0328] The portable information terminal 900 shown in FIGS. 6(A) and 6(B) includes a housing 901, a housing 902, a display unit 90 3, and a hinge portion 905 and the like.

[0329] The housing 901 and the housing 902 are connected by a hinge portion 905. The portable information terminal 900 can be unfolded as shown in FIG. 6(B) from the folded state (FIG. 6(A)). Thereby, it is excellent in portability when carried, and has excellent visibility due to a large display area when used.

[0330] A flexible display unit 903 is provided across the housing 901 and the housing 902 connected by the hinge portion 905 in the portable information terminal 900.

[0331] The light-emitting device manufactured using one aspect of the present invention can be used for the display unit 903. Thus, a portable information terminal having high reliability can be manufactured.

[0332] The display unit 903 can display at least one of document information, still images, moving images, etc. When document information is displayed on the display unit, the portable information terminal 900 can be used as an e-book terminal.

[0333] When the portable information terminal 900 is unfolded, the display unit 903 is held in a state with a large radius of curvature. For example, the display unit 903 is held including a portion curved with a radius of curvature of 1 mm or more and 50 mm or less, preferably 5 mm or more and 30 mm or less. A part of the display unit 903 is from the housing 901 to the housing Pixels are continuously arranged over the body 902, and a curved display can be performed.

[0334] The display unit 903 functions as a touch panel and can be operated by a finger, a stylus, etc. Yes.

[0335] The display unit 903 is preferably composed of a single flexible display. This enables continuous display without interruption between the housing 901 and the housing 902. It should be noted that a configuration in which a display is provided on each of the housing 901 and the housing 902 may also be possible. This enables continuous display without interruption between the housing 901 and the housing 902. It should be noted that a configuration in which a display is provided on each of the housing 901 and the housing 902 may also be possible. On each of the housing 901 and the housing 902, a configuration in which a display is provided may also be possible. Yes.

[0336] When the portable information terminal 900 is unfolded, the hinge portion 905 preferably has a locking mechanism so that the angle between the housing 901 and the housing 902 does not become larger than a predetermined angle. For example, the angle at which locking occurs (it cannot be opened further) is preferably 90 degrees or more and less than 180 degrees, and typically can be 90 degrees, 120 degrees, 135 degrees, 150 degrees, or 175 degrees, etc. This can enhance the convenience, safety, and reliability of the portable information terminal 900. When the hinge portion 905 has a locking mechanism, it is possible to prevent the display unit 903 from being damaged without applying excessive force to the display unit 903. Therefore, a highly reliable portable information terminal can be realized. For example, the angle at which locking occurs (it cannot be opened further) is preferably 90 degrees or more and less than 180 degrees, and typically can be 90 degrees, 120 degrees, 135 degrees, 150 degrees, or 175 degrees, etc. This can enhance the convenience, safety, and reliability of the portable information terminal 900. Preferably, it is, and typically, it can be such as 90 degrees, 120 degrees, 135 degrees, 150 degrees, or 175 degrees, etc. This can enhance the convenience, safety, and reliability of the portable information terminal 900. This can enhance the convenience, safety, and reliability of the portable information terminal 900. Yes.

[0337] When the hinge portion 905 has a locking mechanism, it is possible to prevent the display unit 903 from being damaged without applying excessive force to the display unit 903. Therefore, a highly reliable portable information terminal can be realized. Yes.

[0338] The housing 901 and the housing 902 may have a power button, an operation button, an external connection port, a speaker, a microphone, etc. Yes.

[0339] A wireless communication module is provided in either the housing 901 or the housing 902, and It is possible to transmit and receive data via computer networks such as the Internet, LAN (Local Area Network), and Wi-Fi (registered trademark ).

[0340] The mobile information terminal 910 shown in Fig. 6(C) includes a housing 911, a display unit 912, operation buttons 913 , an external connection port 914, a speaker 915, a microphone 916, a camera 917, etc.

[0341] The light-emitting device manufactured using one aspect of the present invention can be used for the display unit 912. By doing so, a mobile information terminal can be manufactured with high yield.

[0342] The mobile information terminal 910 is provided with a touch sensor on the display unit 912. All operations such as making a call or inputting characters can be performed by touching the display unit 912 with a finger or a stylus, etc.

[0343] Also, by operating the operation buttons 913, it is possible to turn the power on and off and switch the type of image displayed on the display unit 912. For example, it is possible to switch from the mail creation screen to the main menu screen.

[0344] Further, by providing a detection device such as a gyro sensor or an acceleration sensor inside the mobile information terminal 910, it is possible to determine the orientation (portrait or landscape) of the mobile information terminal 910 and automatically switch the display orientation of the display unit 912. Also, the switching of the screen display orientation can be performed by touching the display unit 912, operating the operation buttons 913, or voice input using the microphone 916 and so on.

[0345] ​The mobile information terminal 910 has one or more functions selected from, for example, a telephone, a notebook, or an information browsing device, etc. Specifically, it can be used as a smartphone. The mobile information terminal 910 can execute various applications such as mobile phone, email, text browsing and creation, music playback, video playback, Internet communication, and games.

[0346] The camera 920 shown in FIG. 6(D) has a housing 921, a display unit 922, operation buttons 923, a shutter button 924, etc. Further, a detachable lens 926 is attached to the camera 920.

[0347] The light-emitting device manufactured using one aspect of the present invention can be used for the display unit 922. Thereby, a camera having high reliability can be manufactured.

[0348] Here, the camera 920 is configured such that the lens 926 can be removed from the housing 921 and replaced, but the lens 926 and the housing 921 may be integrated.

[0349] The camera 920 can capture a still image or a moving image by pressing the shutter button 924. In addition, the display unit 922 has a function as a touch panel, and it is also possible to capture an image by touching the display unit 922.

[0350] Note that the camera 920 can be separately equipped with a strobe device, a viewfinder, etc. Or, these may be incorporated in the housing 921.

[0351] FIG. 7(A) shows a wristwatch-type mobile information terminal 9200, and FIG. 7(B) shows a wristwatch-type mobile information terminal ​​​9201 is a perspective view showing each of them.

[0352] The mobile information terminal 9200 shown in Fig. 7(A) can execute various applications such as mobile phones, e-mails, text viewing and creation, music playback, Internet communication, computer games, etc. In addition, the display unit 9001 is provided with a curved display surface and can perform display along the curved display surface. In addition, the mobile information terminal 9200 can perform short-range wireless communication that complies with communication standards. For example, it can communicate with a wireless headset to make a hands-free call. In addition, the mobile information terminal 9200 has a connection terminal 9006 and can directly exchange data with other information terminals via a connector. In addition, charging can also be performed via the connection terminal 9006. Incidentally, the charging operation may be performed by wireless power supply without using the connection terminal 9006.

[0353] The mobile information terminal 9201 shown in Fig. 7(B) is different from the mobile information terminal shown in Fig. 7(A) in that the display surface of the display unit 9001 is not curved. In addition, the outer shape of the display unit of the mobile information terminal 9201 is non-rectangular (circular in Fig. 7(B)).

[0354] Figs. 7(C) to (E) are perspective views showing the foldable mobile information terminal 9202. Incidentally, Fig. 7(C) is a perspective view of the mobile information terminal 9202 in an unfolded state, and Fig. 7(D) is a perspective view of the mobile information terminal 9202 in a state changing from one of the unfolded state or the folded state to the other. Fig. 7(E) is a perspective view of the mobile information terminal 9202 in a folded state.

[0355] The mobile information terminal 9202 is excellent in portability when in a folded state, and when in a deployed state, it has an excellent display overview due to a wide display area without seams. The display unit 9001 of the mobile information terminal 9202 is supported by three housings 9000 connected by a hinge 9055. By bending between two housings 9000 via the hinge 9055, the mobile information terminal 9 202 can be reversibly deformed from a deployed state to a folded state. For example, the mobile information terminal 9202 can be bent with a radius of curvature of 1 mm or more and 150 mm or less.

[0356] FIG. 8(A) is a schematic diagram showing an example of a cleaning robot.

[0357] The cleaning robot 5100 has a display 5101 disposed on the upper surface, a plurality of cameras 5102 disposed on the side surface, a brush 5103, and operation buttons 5104. Although not shown, tires, suction ports, etc. are provided on the lower surface of the cleaning robot 5100. The cleaning robot 5100 is further provided with various sensors such as an infrared sensor, an ultrasonic sensor, an acceleration sensor, a piezo sensor, a light sensor, and a gyro sensor. In addition, the cleaning robot 5 100 is provided with wireless communication means.

[0358] The cleaning robot 5100 can move autonomously, detect dust 5120, and suck the dust from the suction port provided on the lower surface.

[0359] In addition, the cleaning robot 5100 can analyze an image captured by the camera 5102 and determine the presence or absence of obstacles such as walls, furniture, or steps. Also, when an object that is likely to get caught in the brush 5103 such as wiring is detected by image analysis, the rotation of the brush 5103 can be stopped. It is possible.

[0360] The display 5101 can display the remaining battery level, the amount of dust sucked, etc. It is also possible to display on the display 5101 the path traveled by the cleaning robot 5100. Further, the display 5101 may be a touch panel, and the operation buttons 5104 may be provided on the display 5101.

[0361] The cleaning robot 5100 can communicate with a portable electronic device 5140 such as a smartphone. The image captured by the camera 5102 can be displayed on the portable electronic device 5140. Therefore, the owner of the cleaning robot 5100 can know the state of the room even when away from home. Also, the display on the display 5101 can be confirmed using a portable electronic device such as a smartphone.

[0362] The light-emitting device according to one aspect of the present invention can be used for the display 5101.

[0363] The robot 2100 shown in FIG. 8(B) includes an arithmetic unit 2110, an illuminance sensor 2101, a microphone 2102, an upper camera 2103, a speaker 2104, a display 2105, a lower camera 2106, an obstacle sensor 2107, and a moving mechanism 2108. The microphone 2102 has a function of detecting the user's voice and environmental sounds, etc. Also, the speaker 2104 has a function of emitting sound. The robot 2100 can communicate with the user using the microphone 2102 and the speaker 2104.

[0364] It is possible.

[0365] The display 2105 has a function of displaying various information. The robot 2100 can display the information desired by the user on the display 2105. The display 2105 may be equipped with a touch panel. Further, the display 2105 may be a detachable information terminal, and by being installed at a fixed position of the robot 2100, charging and data transfer can be enabled.

[0366] The upper camera 2103 and the lower camera 2106 have a function of imaging the surroundings of the robot 2100. Also, the obstacle sensor 2107 can detect the presence or absence of obstacles in the traveling direction when the robot 210 0 travels using the moving mechanism 2108. The robot 21 00 can recognize the surrounding environment and move safely by using the upper camera 2103, the lower camera 2106, and the obstacle sensor 2107.

[0367] The light-emitting device according to one aspect of the present invention can be used for the display 2105.

[0368] FIG. 8(C) is a diagram showing an example of a goggle-type display. The goggle-type display includes, for example, a housing 5000, a display unit 5001, a speaker 5003 , an LED lamp 5004, operation keys 5005 (including a power switch or an operation switch) , connection terminals 5006, sensors 5007 (including functions for measuring force, displacement, position, speed, acceleration, angular velocity, rotation speed , distance, light, liquid, magnetism, temperature, chemical substances, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays), microphones 5008, a second display unit 5002, a support unit 5012, earphones 5013, etc.

[0369] The light-emitting device according to one aspect of the present invention can be used for the display unit 5001 and the second display unit 5002. It is possible.

[0370] Also, FIGS. 9(A) and (B) show a foldable portable information terminal 5150. The foldable portable information terminal 5150 has a housing 5151, a display area 5152, and a bending portion 5153. FIG. 9(A) shows the portable information terminal 5150 in an unfolded state. FIG. 9(B) shows the portable information terminal 5150 in a folded state. Despite having a large display area 5152, the portable information terminal 5150 can be folded into a compact and highly portable form.

[0371] The display area 5152 can be folded in half by the bending portion 5153. The bending portion 515 3 is composed of a stretchable member and a plurality of support members. When folding, the stretchable member extends, and the bending portion 5153 has a curvature radius of 2 mm or more, preferably 5 mm or more and is folded.

[0372] Note that the display area 5152 may be a touch panel (input / output device) equipped with a touch sensor (input device). The light-emitting device according to one aspect of the present invention can be used for the display area 5152. It is possible.

[0373] This embodiment can be appropriately combined with other embodiments.

[0374] (Embodiment 7) In this embodiment, an example of applying the light-emitting element according to one aspect of the present invention to various lighting devices will be described with reference to FIGS. 10 and 11. By using the light-emitting element which is one aspect of the present invention, a lighting device with good luminous efficiency and high reliability can be fabricated. It is possible.

[0375] The light-emitting element of one embodiment of the present invention can be fabricated over a flexible substrate to have a curved surface. It is possible to realize electronic devices and lighting devices having a light-emitting region.

[0376] In addition, a light-emitting device using a light-emitting element according to one embodiment of the present invention can be used for automobile lighting. For example, lighting can be installed on the windshield, ceiling, etc.

[0377] FIG. 10(A) shows a perspective view of one side of a multifunction terminal 3500, and FIG. 3 shows a perspective view of the other side of the multi-function terminal 3500. 2 incorporates a display unit 3504, a camera 3506, and lighting 3508. The light emitting device of the embodiment can be used for lighting 3508.

[0378] The light emitting device according to one embodiment of the present invention is used for the light source 3508, and the light source 3508 functions as a surface light source. Therefore, unlike point light sources such as LEDs, light with little directionality can be obtained. For example, when the lighting 3508 and the camera 3506 are used in combination, the lighting 3508 is turned on. The camera 3506 can capture the image by turning the light on or off. Because it functions as a surface light source, it is possible to take photos that look like they were taken under natural light. Cut.

[0379] The multifunction terminal 3500 shown in FIGS. 10(A) and 10(B) is similar to the multifunction terminal 3500 shown in FIGS. 7(A) to 7(C). As with the electronic device shown in FIG.

[0380] In addition, inside the housing 3502, a speaker, a sensor (force, displacement, position, speed, acceleration, angle Speed, rotational speed, distance, light, liquid, magnetism, temperature, chemical substances, sound, time, hardness, electric field, current, Voltage, power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays, including a function for measuring them things), and can have a microphone or the like. Also, inside the multifunctional terminal 3500, By providing a detection device having sensors for detecting inclination, such as a gyro and an acceleration sensor, the multi- functional terminal 3500 can determine its orientation (vertical or horizontal) and automatically switch the screen display of the display unit 3504.

[0381] The display unit 3504 can also function as an image sensor. For example, by touching the display unit 3 504 with a palm or finger and imaging palm prints, fingerprints, etc., personal authentication can be performed. Also, by using a backlight that emits near-infrared light or a light source for sensing that emits near-infrared light on the display unit 3504, finger veins, palm veins, etc. can also be imaged. Note that the light-emitting device according to an aspect of the present invention may be applied to the display unit 35 04.

[0382] FIG. 10(C) shows a perspective view of the anti-theft light 3600. The light 3600 has lighting 3608 on the outside of the housing 3602, and a speaker 3610 or the like is incorporated in the housing 3602. The light-emitting element according to an aspect of the present invention can be used for the lighting 3608.

[0383] The light 3600 can emit light, for example, by gripping, holding, or retaining the lighting 3608. Also, inside the housing 3602, an electronic circuit for controlling the light-emitting method of the light 3600 may be provided. As the electronic circuit, for example, a circuit that can emit light once or intermittently a plurality of times may be used, or a circuit that controls the current value of light emission to emit light may also be used, and by controlling the current value of light emission, It may also be a circuit capable of adjusting the amount of light. Also, a circuit may be incorporated such that a loud warning sound is output from the speaker 3610 simultaneously with the emission of light from the lighting 3608. It may also be incorporated into a circuit that outputs a loud warning sound from the speaker 3610 simultaneously with the emission of light from the lighting 3608.

[0384] Since the light 3600 can emit light in all directions, for example, it can direct light or intimidate with light and sound at a thug or the like. Also, the light 3600 may be equipped with a camera such as a digital still camera or a function having a photographing function. Since the light 3600 can emit light in all directions, for example, it can direct light or intimidate with light and sound at a thug or the like. Also, the light 3600 may be equipped with a camera such as a digital still camera or a function having a photographing function. It may also be equipped with a camera such as a digital still camera or a function having a photographing function.

[0385] FIG. 11 shows an example in which a light-emitting element is used as an indoor lighting device 8501. Since the light-emitting element can also be made larger in area, a large-area lighting device can also be formed. In addition, by using a housing having a curved surface, a lighting device 8502 having a curved light-emitting area can be formed. The light-emitting element shown in this embodiment is in the form of a thin film, and the degree of freedom in the design of the housing is high. Since the light-emitting element can also be made larger in area, a large-area lighting device can also be formed. In addition, by using a housing having a curved surface, a lighting device 8502 having a curved light-emitting area can be formed. The light-emitting element shown in this embodiment is in the form of a thin film, and the degree of freedom in the design of the housing is high. In addition, by using a housing having a curved surface, a lighting device 8502 having a curved light-emitting area can be formed. The light-emitting element shown in this embodiment is in the form of a thin film, and the degree of freedom in the design of the housing is high. In addition, by using a housing having a curved surface, a lighting device 8502 having a curved light-emitting area can be formed. The light-emitting element shown in this embodiment is in the form of a thin film, and the degree of freedom in the design of the housing is high. Therefore, lighting devices with various designs can be formed. Furthermore, a large-sized lighting device 8503 may be provided on the interior wall surface. Also, a touch sensor may be provided on the lighting devices 8501, 8502, 8503 to turn the power on or off. Therefore, lighting devices with various designs can be formed. Furthermore, a large-sized lighting device 8503 may be provided on the interior wall surface. Also, a touch sensor may be provided on the lighting devices 8501, 8502, 8503 to turn the power on or off. Therefore, lighting devices with various designs can be formed. Furthermore, a large-sized lighting device 8503 may be provided on the interior wall surface. Also, a touch sensor may be provided on the lighting devices 8501, 8502, 8503 to turn the power on or off.

[0386] Also, by using the light-emitting element on the surface side of the table, a lighting device 8504 having a function as a table can be obtained. In addition, by using the light-emitting element on a part of other furniture, a lighting device having a function as furniture can be obtained. Also, by using the light-emitting element on the surface side of the table, a lighting device 8504 having a function as a table can be obtained. In addition, by using the light-emitting element on a part of other furniture, a lighting device having a function as furniture can be obtained. Also, by using the light-emitting element on a part of other furniture, a lighting device having a function as furniture can be obtained.

[0387] As described above, a lighting device and an electronic device can be obtained by applying the light-emitting device according to one aspect of the present invention. Note that the applicable lighting devices and electronic devices are not limited to those shown in this embodiment, and can be applied to electronic devices in all fields. As described above, a lighting device and an electronic device can be obtained by applying the light-emitting device according to one aspect of the present invention. Note that the applicable lighting devices and electronic devices are not limited to those shown in this embodiment, and can be applied to electronic devices in all fields. As described above, a lighting device and an electronic device can be obtained by applying the light-emitting device according to one aspect of the present invention. Note that the applicable lighting devices and electronic devices are not limited to those shown in this embodiment, and can be applied to electronic devices in all fields.

[0388] The structure described in this embodiment may be used in appropriate combination with structures described in other embodiments. There can be. EXAMPLES

[0389] In this example, one of the organometallic complexes of the present invention shown in the structural formula (100) in the first embodiment is In one embodiment, tris{2-[1-(2,6-diisobutylphenyl)-1H-naphtho[1 ,2-d]imidazol-2-yl-κN 3 ]phenyl-κC}iridium(III)( Abbreviation: [Ir(pni-diBup) 3 ]) synthesis method is explained.

[0390] <Step 1: Synthesis of 2,6-diisobutylaniline> 2,6-Dichloroaniline 100g (617mmol), Isobutylboronic acid 230g (2256mmol), potassium phosphate tripotassium phosphate 479g (2256mmol), 2-dicyclo Hexylphosphino-2',6'-dimethoxybiphenyl (S-phos) 10g (24 .7 mmol) and 3000 mL of toluene were placed in a 5000 mL three-neck flask. The air in the flask was replaced with nitrogen, and the mixture was degassed by stirring while reducing the pressure inside the flask. Add 11 g (11.5 mmol) of bis(dibenzylideneacetone)dipalladium(0), The mixture was stirred at 120° C. for 12 hours under a nitrogen stream. After a predetermined time had elapsed, the resulting reaction solution was filtered by suction. The filtrate was purified by extraction with toluene. The product was purified by chromatography using a hexane:toluene ratio of 15:1 as the developing solvent. The obtained fraction was concentrated to obtain the target product, a black oil, 79 g, 62% yield. It was obtained in [Step 1]. The synthesis scheme of Step 1 is shown in the following formula (A-1).

[0391]

Chemical formula

[0392] <Step 2; Synthesis of 2-nitronaphthalene-1-trifluoromethanesulfonate> 35 g (182 mmol) of 2-nitro-1-naphthol and 500 mL of dehydrated dichloromethane , 51 mL (365 mmol) of triethylamine were placed in a 1000 mL three-necked flask, and the inside of the flask was purged with nitrogen and cooled to 0 °C. Here, trifluoromethanesulfonic anhydride (abbreviation: Tf 2 O) 40 mL (243 mmol) was added dropwise, and the mixture was stirred at 0 °C for 1 hour and then stirred at room temperature for 20 hours. After a predetermined time elapsed, 300 mL of water and 30 mL of 1 M hydrochloric acid were added to the obtained mixture . Then, this mixture was purified by extraction with dichloromethane. After that, it was purified by silica column chromatography. As the developing solvent, hexane:dichloro methane = 5:1 was used. The obtained fraction was concentrated to obtain 47 g of the desired yellow oily substance in a yield of 80%. The synthesis scheme of Step 2 is shown in the following formula (A-2). The synthesis scheme of Step 2 is shown in the following formula (A-2).

[0393]

Chemical formula

[0394] <Step 3; Synthesis of N-(2,6-diisobutylphenyl)-2-nitro-1-naphthalenamine> The synthesis of N-(2,6-diisobutylphenyl)-2-nitro-1-naphthalenamine> 30 g (146 mmol) of 2,6-diisobutylaniline synthesized in Step 1, and 47 g (1 46 mmol), 81 g (248 mmol) of cesium carbonate, and 750 mL of toluene were placed in a 200 0 mL three-necked flask. The inside of the flask was purged with nitrogen and stirred while the inside of the flask was under reduced pressure to degas this mixture. After degassing, 4.8 g (11.7 mmol) of S-phos and 2.7 g (2.9 mmol) of tris( (dibenzylideneacetone)dipalladium(0) were added, and the mixture was stirred at 130 °C for 28 hours under a nitrogen stream. After the predetermined time had elapsed, the resulting reaction mixture was purified by extraction with toluene . Thereafter, it was purified by silica column chromatography . Hexane:ethyl acetate = 15:1 was used as the eluent. The resulting fractions were concentrated to obtain 13 g of a yellow oil in a 23% yield. The synthesis scheme for Step 3 is shown in the following formula( A-3).

[0395] [Chemical formula]

[0396] [Step 4; Synthesis of N-(2,6-diisobutylphenyl)-1,2-naphthalenediamine] [ / Synthesis] 13 g (34 mmol) of N-(2,6-diisobutylphenyl)-2-nitro-1-naphth ylamine synthesized in Step 3, 6.1 mL (0.34 mol) of water, and 40 0 mL of ethanol were placed in a 1000 mL three-necked flask and stirred. 3 2 g (0.17 mol) of tin(II) chloride was added thereto, and the mixture was stirred at 80 °C for 5 hours under a nitrogen stream . After the predetermined time had elapsed , the resulting reaction mixture was poured into 500 mL of a 2 M aqueous sodium hydroxide solution and stirred at room temperature for 2 hours The solution was purified by extraction with chloroform. Subsequently, it was purified by silica column chromatography using hexane:ethyl acetate = 15:1 as the developing solvent. The resulting fraction was concentrated to obtain 9.5 g of the target black oily substance with a yield of 81%. The synthetic scheme for Step 4 is shown in the following formula (A-4).

[0397]

Chemical Structure

[0398] <Step 5; Synthesis of 1-(2,6-Diisobutylphenyl)-2-phenyl-1H-naphtho 1,2-d]imidazole (abbreviation: Hpni-diBup)> 9.5 g (27 mmol) of N-(2,6-diisobutylphenyl)-1,2-naphthalenediamine synthesized in Step 4, 100 mL of acetonitrile, and 2.9 g (27 mmol) of benzaldehyde were placed in a 300 mL eggplant flask and stirred at 100 °C for 6 hours. 0.044 g (0.274 mmol) of iron(III) chloride was added to this mixture and stirred at 100 °C for 16 hours. After the specified time had elapsed, the resulting reaction mixture was extracted with ethyl acetate, and 100 mL of toluene and 10 g of manganese(IV) oxide were added to the resulting oily substance and placed in a 300 mL eggplant flask and stirred at 130 °C for 7 hours. After the specified time had elapsed, the resulting reaction mixture was filtered through Celite (Wako Pure Chemical Industries, Ltd., catalog number: 537-02305) / Florisil (Wako Pure Chemical Industries, Ltd., catalog number: 066-05265) / aluminum oxide by suction filtration. The resulting filtrate was concentrated to obtain an oily substance. The obtained oily substance was purified by silica column chromatography using toluene as the developing solvent. The resulting fraction (Wako Pure Chemical Industries, Ltd., catalog number: 537-02305) / Florisil (Wako Pure Chemical Industries, Ltd., catalog number: 066-05265) / aluminum oxide by suction filtration. The resulting filtrate was concentrated to obtain an oily substance. The obtained oily substance was purified by silica column chromatography using toluene as the developing solvent. The resulting fraction was concentrated to obtain an oily substance. The obtained oily substance was purified by silica column chromatography using toluene as the developing solvent. The resulting fraction ​​It was concentrated to obtain 7.9 g of the target white solid with a yield of 66%. The synthesis scheme of Step 5 The key species is shown by the following formula (A-5).

[0399] [Chemical formula]

[0400] <Step 6; Di-μ-chloro-tetrakis{2-[1-(2,6-diisobutylphenyl )-1H-naphtho[1,2-d]imidazol-2-yl-κN 3 phenyl-κC} Diiridium(III) (abbreviation: [Ir(pni-diBup) 2 Cl] 2 ) synthesis> 3.3 g (7.7 mmol) of 1-(2,6-diisobutylphenyl)-2-phenyl-1H-naphtho[1,2-d]imidazole (abbreviation: Hpni-diBup) synthesized in Step 5, 1.6 g (3.7 mmol) of iridium chloride monohydrate, 30 mL of 2-ethoxyethanol, and 10 mL of water were placed in a 100 mL round-bottom flask, and the inside of the flask was purged with argon. This reaction vessel was irradiated with microwaves (2.45 GHz, 100 W) for 2 hours to carry out the reaction. After the reaction, the reaction solution was suction filtered to obtain 2.8 g of the target yellow solid with a yield of 69 %. The synthesis scheme of Step 6 is shown by the following formula (A-6).

[0401] [Chemical formula]

[0402] <Step 7; Tris{2-[1-(2,6-diisobutylphenyl)-1H-naphtho 1,2-d]imidazol-2-yl-κN 3 phenyl-κC}iridium(III) (Abbreviation: [Ir(pni-diBup) 3 ) synthesis> Di-μ-chloro-tetrakis{2-[1-(2,6-diiso butylphenyl)-1H-naphtho[1,2-d]imidazol-2-yl-κN 3 phen yl-κC}diiridium(III) (abbreviation: [Ir(pni-diBup) 2 Cl] 2 ) 2.0 g (0.92 mmol), 150 mL of dichloromethane were placed in a 500 mL three-necked flask and stirred under a nitrogen stream. A mixed solution of 0. 72 g (2.8 mmol) of silver trifluoromethanesulfonate and 150 mL of methanol was added dropwise, and the mixture was stirred in the dark for 3 days . After the reaction for a predetermined time, the reaction mixture was passed through celite and filtered. The obtained filtrate was concentrated to obtain 2.7 g of a yellow solid. 2.7 g of the obtained solid, 50 mL of ethanol, and 1-(2,6-diisobutylphenyl)-2-phenyl-1H-naphtho [1,2-d]imidazole (abbreviation: Hpni-diBup) 1.6 g (3.7 mmo l) synthesized by the method of Step 5 were placed in a 500 mL eggplant flask and heated under reflux for 20 hours under a nitrogen stream. After the reaction for a predetermined time , the reaction mixture was suction filtered to obtain a solid. The obtained solid was dissolved in dichloromethane and suction filtered through celite / neutral silica / celite. The obtained filtrate was concentrated to obtain a solid . The obtained solid was purified by silica column chromatography. The developing solvent was , dichloromethane:hexane = 1:3. The obtained fraction was concentrated to obtain a solid . The obtained solid was recrystallized from ethyl acetate / hexane to obtain 1.1 g of a solid, with a yield of 40% . The synthesis scheme is shown in the following formula (A-7).

[0403] [Chemical formula]

[0404] 1.1 g of the obtained solid was purified by sublimation using the train sublimation method. The sublimation purification was carried out under the conditions of a pressure of 2.6 Pa and an argon flow rate of 10.5 mL / min. The obtained solid was heated at 340 °C for 41 hours. After sublimation purification, 0.93 g of a yellow solid was obtained with a recovery rate of 88%.

[0405] Proton NMR ( 1 1H-NMR) measurement of the yellow solid obtained above was performed. The values obtained are shown below. Also, 1 the 1H-NMR chart is shown in Figure 12. From Figure 12, it was found that [Ir(pni-diBup) 3 , which is an organometallic complex of one aspect of the present invention, was obtained. 3

[0406] 1 1H-NMR. δ(CD 2 Cl 2 ): 0.15 (d, 9H), 0.39 - 0.42 (m, 18H), 0.59 (d, 9H), 1.27 - 1.35 (m, 3H), 1.78 - 1.8 6 (m, 3H), 1.93 - 2.02 (m, 6H), 2.33 (d, 6H), 6.35 - 6.40 (m, 6H), 6.56 - 6.61 (m, 6H), 7.04 - 7.07 (m, 6 H), 7.16 (t, 3H), 7.25 (d, 3H), 7.30 (t, 3H), 7.40 (d, 3H), 7.48 (d, 3H), 7.63 (t, 3H), 7.73 (d, 3H).

[0407] Subsequently, the ultraviolet-visible absorption spectrum (hereinafter simply referred to as 3 "absorption spectrum") and emission spectrum of the [Ir(pni-diBup) solution were measured. For the measurement of the absorption spectrum, , using an ultraviolet-visible spectrophotometer (V550 model manufactured by JASCO Corporation, Japan), [Ir(pni-di Bup) 3 in a deoxygenated dichloromethane solution (0.0089 mmol / L) was placed in a quartz cell and measured at room temperature. Also, for the measurement of the emission spectrum and the emission quantum yield, an absolute PL quantum yield measurement device (C11347-01 manufactured by Hamamatsu Photonics K.K.) was used, and in a glove box (LABstarM13(1250 / 780) manufactured by BRIGHT Co., Ltd.), a deoxygenated dichloromethane solution (0.0089 mmol / L) was placed in a quartz cell sealed and measured at room temperature. The measurement results of the obtained absorption spectrum and emission spectrum are shown in Fig. 13. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and the emission intensity. Note that the absorption spectrum shown in Fig. 13 is the result obtained by subtracting the absorption spectrum measured with only dichloromethane in the quartz cell from the absorption spectrum measured with a deoxygenated dichloromethane solution in the quartz cell.

[0408] As shown in Fig. 13, the iridium complex [Ir(pni-diBup) 3 has emission peaks at 500 and 53 6 nm, and green emission was observed from the deoxygenated dichloromethane solution.

[0409] Also, when the emission quantum yield at an excitation wavelength of 450 nm in the deoxygenated dichloromethane solution was measured , it was found to be very high at 98%.

Example

[0410] In this example, an organometallic complex of one aspect of the present invention shown as structural formula (101) in Embodiment 1, bis{2-[1-(2,6-diisobutylphenyl)-1H-naphtho[1 ​​​​​ ,2-d]imidazol-2-yl-κN 3 phenyl-κC}[2-(4-methyl-5 -phenyl-2-pyridyl-κN 2 )phenyl-κC]iridium(III) (abbreviation: Ir(pni-diBup) 2 (mdppy)]) will be described regarding its synthesis method.

[0411] <Step 1; Bis{2-[1-(2,6-diisobutylphenyl)-1H-naphtho[1 ,2-d]imidazol-2-yl-κN 3 phenyl-κC}[2-(4-methyl-5 -phenyl-2-pyridyl-κN 2 )phenyl-κC]iridium(III) (abbreviation: Ir(pni-diBup) 2 (mdppy)]) synthesis Di-μ-chloro-tetrakis[2-(4-methyl-5-phenyl-2-pyridinyl-κN )phenyl-κC]diiridium(III) (abbreviation: [Ir(mdppy) 2 Cl] 2 ) 1.3 g (0.9 mmol) and 180 mL of dichloromethane were placed in a 500 mL three-necked flask and stirred under a nitrogen stream. To this mixed solution was added dropwise a mixed solution of 0.7 g of silver trifluoromethanesulfonate (2.7 mmol) and 35 mL of methanol, and the mixture was stirred for 18 hours in the dark. After the reaction for the predetermined time, the reaction mixture was passed through celite and filtered. The obtained filtrate was concentrated, and 1.9 g of a yellow solid was obtained. 1.9 g of the obtained yellow solid, 30 mL of methanol, ethanol 30 mL, and 1.6 g (3.6 mmol) of Hpni-diBup were placed in a 300 mL eggplant flask and heated under reflux for 23 hours under a nitrogen stream. After the reaction for the predetermined time, the reaction mixture was suction filtered , after removing the insoluble matter, the filtrate was concentrated to obtain a solid. 60 mL of 1-butanol was added to the obtained solid and heated under reflux for 22 hours under a nitrogen stream. After reacting for a predetermined time, the reaction mixture was suction filtered to obtain a solid. The obtained solid was purified by silica column chromatography. The developing solvent used was a mixed solvent of hexane:dichloromethane = 3:1. The obtained fraction was concentrated to obtain a solid. The obtained solid was recrystallized from ethyl acetate / hexane, and 0.20 g of the target yellow solid was obtained with a yield of 9%. The synthesis scheme is shown in the following formula (B-1).

[0412]

Chemical formula

[0413] 0.19 g of the obtained solid was purified by sublimation using the train sublimation method. The sublimation purification was performed by heating the obtained solid at 320 °C for 18 hours under the conditions of a pressure of 2.5 Pa and an argon flow rate of 10.3 mL / min. After sublimation purification, 0.14 g of a yellow solid was obtained with a recovery rate of 72%.

[0414] 1H-NMR measurement of the yellow solid obtained above was 1 performed. The values obtained are shown below. Also, 1 the 1H-NMR chart is shown in FIG. 14. From FIG. 14, it was found that [Ir(pni-diBup) (mdppy)], which is an organometallic complex of one aspect of the present invention, was obtained. 2 (mdppy)] was obtained.

[0415] 1 1H-NMR.δ(CD 2 Cl 2 ): 0.09 - 0.15 (m, 9H), 0.29 - 0. 34 (m, 9H), 0.40 (t, 1H), 0.45 (d, 3H), 0.51 (d, 3H ​​), 1.18 - 1.24 (m, 1H), 1.34 - 1.49 (m, 1H), 1.70 - 1 .78 (m, 1H), 1.88 - 2.09 (m, 6H), 2.17 - 2.25 (m, 2H ), 2.51 (s, 3H), 6.30 - 6.40 (m, 3H), 6.48 (t, 1H), 6.61 - 6.52 (m, 3H), 6.64 - 6.69 (m, 2H), 6.74 - 6.7 9 (m, 2H), 6.83 (t, 1H), 6.93 - 7.01 (m, 3H), 7.08 ( t, 1H), 7.13 - 7.25 (m, 8H), 7.34 - 7.51 (m, 6H), 7. 57 - 7.73 (m, 4H), 7.87 (d, 1H), 7.94 (s, 1H), 8.31 (s, 1H).

[0416] Subsequently, the deoxygenated dichloromethane solution of [Ir(pni - diBup) 2 (mdppy)] (0.0073 mmol / L) was measured for its absorption spectrum, emission spectrum, and emission quantum yield . The measurement was carried out in the same manner as in Example 1. The measurement results of the absorption spectrum and emission spectrum are shown in Figure 15.

[0417] As shown in Figure 15, the iridium complex [Ir(pni - diBup) 2 (mdppy)] has an emission peak at 530 nm, and green emission was observed from the deoxygenated dichloromethane solution.

[0418] Also, when the emission quantum yield at an excitation wavelength of 450 nm in the deoxygenated dichloromethane solution (0.0073 mmol / L) was measured, it was found to be very high at 98%.

Example

[0419] In this example, the organometallic of one aspect of the present invention shown as structural formula (102) in Embodiment 1 Tris{2-[1-(4-cyano-2-isobutylphenyl)-1H-naphth [1,2-d]imidazol-2-yl-κN}phenyl-κC}iridium(II 3 I)(abbreviation: [Ir(pni-iBuCNp) ) synthesis method will be described. 3 will be described.

[0420] <Step 1; Synthesis of 4-amino-3-isobutylbenzonitrile> 75 g (492 mmol) of 4-amino-3-chlorobenzonitrile, isobutylboronic acid 90 g (886 mmol), tripotassium phosphate 188 g (886 mmol), 2-dicy clohexylphosphino-2’,6’-dimethoxybiphenyl (S-phos) 4.0 g (9.8 mmol), 2400 mL of toluene were placed in a 5000 mL three-necked flask, and the flask interior was purged with nitrogen, stirred while reducing the pressure inside the flask, and the mixture was degassed. After degassing, 4.5 g (4.9 mmol) of tris(dibenzylideneacetone)dipalladium(0) was added and stirred at 120 °C for 20 hours under a nitrogen stream. After a predetermined time elapsed, the obtained reaction solution was filtered by suction. The obtained filtrate was purified by extraction using toluene. Then, it was purified by silica gel column chromatography. Toluene was used as the eluent. The obtained fraction was concentrated to obtain 59 g of the target brown oil with a yield of 69%. The synthesis scheme of Step 1 is shown in the following formula (C-1).

[0421]

Chemical formula

[0422] <Step 2; 3-Isobutyl-4-[N-(2-nitronaphthyl)amino]benzonitrile Synthesis of riluzole> 30 g (170 mmol) of 4-amino-3-isobutylbenzonitrile synthesized in Step 1, 45 g (141 mmol) of 2-nitronaphthalene-1-trifluoromethanesulfonate, 78 g (240 mmol) of cesium carbonate, and 750 mL of toluene were placed in a 2000 mL three-necked flask. The inside of the flask was purged with nitrogen, the inside of the flask was stirred under reduced pressure, and the mixture was degassed. After degassing, 4.6 g (11 mmol) of 2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl (S-phos), 2.6 g (2.8 mmol) of tris(dibenzylideneacetone)dipalladium(0) were added, and the mixture was stirred at 130 °C for 24 hours under a nitrogen stream. After the lapse of the predetermined time, the resulting reaction mixture was purified by extraction with toluene. Thereafter, it was purified by silica column chromatography. Hexane:ethyl acetate = 10:1 was used as the developing solvent. The obtained fraction was concentrated to obtain 40 g of the desired yellow oily substance in a yield of 82%. The synthesis scheme of Step 2 is shown in the following formula (C-2).

[0423]

Chemical formula

[0424] <Step 3; Synthesis of 3-isobutyl-4-[N-(1,2-naphthalenediamine)]benzonitrile> 40 g (115 mmol) of 3-isobutyl-4-[N-(2-nitronaphthyl)amino]benzonitrile synthesized in Step 2, 21 mL (1.2 mol) of water, and 1350 mL of ethanol were placed in a 3000 mL three-necked flask and stirred. Tin(II) chloride 1 ​​​​​​​​09 g (0.58 mol) was added, and the mixture was stirred at 80 °C for 6 hours under a nitrogen stream. After the predetermined time elapsed, the resulting reaction mixture was poured into 500 mL of 2 M aqueous sodium hydroxide solution and stirred at room temperature for 2 hours. The precipitated precipitate was collected by suction filtration, washed with chloroform, and a filtrate was obtained. The obtained filtrate was purified by extraction with chloroform. Then, hexane was added to the obtained solid and suction filtration was carried out to obtain 32 g of a white solid in a yield of 88%. The synthesis scheme of Step 3 is shown in the following formula (C-3).

[0425] <Chemical formula>

[0426] <Step 4; Synthesis of 1-(4-cyano-2-isobutylphenyl)-2-phenyl-1H-naphtho[1,2-d]imidazole (abbreviation: Hpni-iBuCNp)>[[]] 32 g (101 mmol) of 3-isobutyl-4-[N-(1,2-naphthalenediamine)]benzonitrile synthesized in Step 3, 400 mL of acetonitrile, and 11 g (101 mmol) of benzaldehyde were placed in a 1000 mL three-necked flask and stirred at 100 °C for 6 hours. To this mixture, 0.16 g (1.0 mmol) of iron(III) chloride was added, and the mixture was stirred at 100 °C for 16 hours. After the predetermined time elapsed, the resulting reaction mixture was extracted with ethyl acetate. Then, the obtained solid was purified by silica column chromatography. The developing solvent was first toluene, and then a mixed solvent of toluene:ethyl acetate = 18:1 was used. The obtained fraction was concentrated to obtain a solid. Ethyl acetate was added to the obtained solid and suction filtration was carried out to obtain 14 g of a white solid as the target product in a yield of 34%. The synthesis of Step 4 ​​​​​​​​The scheme is shown in the following formula (C-4).

[0427]

Chemical formula

[0428] <Step 5; Tris{2-[1-(4-cyano-2-isobutylphenyl)-1H-naphtho [1,2-d]imidazol-2-yl-κN 3 phenyl-κC}iridium(I II)(abbreviation: [Ir(pni-iBuCNp) 3 ) synthesis> 1-(4-Cyano-2-isobutylphenyl)-2-phenyl -1H-naphtho[1,2-d]imidazole 3.8 g (9.5 mmol) synthesized by the method of Step 4 and tris(acetylacetonato)iridium(III) 0.93 g (1.9 mmol) were placed in a reaction vessel equipped with a three-way cock and heated at 250 °C for 40 hours. Dichloromethane was added to the obtained reaction mixture to remove insoluble substances. The obtained filtrate was concentrated to obtain a solid. The obtained solid was purified by silica column chromatography. Dichloromethane was used as the developing solvent. The obtained fraction was concentrated to obtain a solid. The obtained solid was recrystallized from ethyl acetate / heptane to obtain 0.3 g of a yellow solid in a yield of 10%. This synthetic scheme is shown in the following formula (

[0429] C-5).

[0429]

Chemical formula

[0430] The mass (MS) of the yellow solid obtained above was measured. The ESI-MS measurement results of the obtained compound are shown below. ESI-MS [M+H +=1394.51 (Exact Mass =1393.51). From this, the organometallic complex of one embodiment of the present invention represented by the above structural formula (102), [Ir(pni-iBuCNp) 3 was found to be obtained.

[0431] Subsequently, the absorption spectrum and emission spectrum of the dichloromethane deoxygenated solution (0.013 mmol / L) of [Ir(pni-iBuCNp) 3 obtained above were measured. The measurement was carried out in the same manner as in Example 1. The absorption spectrum and emission spectrum are shown in Fig. 16. As shown in Fig. 16, the iridium complex [Ir(pni-iBuCNp)

[0432] has emission peaks at 509, 5 3 44 nm, and green emission was observed from the dichloromethane deoxygenated solution.

Example

[0433] In this example, the organometallic complex of one embodiment of the present invention shown as structural formula (103) in Embodiment 1, tris{2-[1-(4-cyano-2,6-diisobutylphenyl)-1H -naphtho[1,2-d]imidazol-2-yl-κN 3 phenyl-κC}iridium (III) (abbreviation: [Ir(pni-diBuCNp) 3 ) will be described.

[0434] <Step 1; Synthesis of 4-amino-3,5-diisobutylbenzonitrile> 58 g (310 mmol) of 4-amino-3,5-diisobutylbenzonitrile, 117 g (1145 mmol) of isobutylboronic acid, 243 g (1145 mm of tripotassium phosphate ol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-p hos) 6.4 g (15.5 mmol), 1500 ml of toluene were placed in a 3000 mL three-neck reaction vessel, the inside of the flask was purged with nitrogen, and the mixture was stirred while reducing the pressure inside the flask. This mixture was degassed. After degassing, 5.7 g (6 .2 mmol) of tris(dibenzylideneacetone)dipalladium(0) was added, and the mixture was stirred at 130 °C for 12 hours under a nitrogen stream. To the resulting reaction solution toluene was added, and the mixture was suction filtered through celite. The resulting filtrate was purified by extraction with toluene. Subsequently, it was purified by silica column chromatography. The developing solvent used was toluene. The resulting fraction was concentrated to obtain 69 g of the target yellow oily substance in a yield of 96%. The synthetic scheme of Step 1 is shown in the following formula (D-1).

[0435]

Chemical formula

[0436] <Step 2; Synthesis of 3,5-diisobutyl-4-[N-(2-nitronaphthyl)amino]ben zonitrile> 28 g (121 mmol) of 4-amino-3,5-diisobutylbenzonitrile synthesized in Step 1, 39 g (12 1 mmol) of 2-nitronaphthalene-1-trifluoromethanesulfonate, 67 g (205 mmol) of cesium carbonate, and 750 mL of toluene were placed in a 2000 mL three-neck flask, the inside of the flask was purged with nitrogen, and the mixture was stirred while reducing the pressure inside the flask. This mixture was degassed. After degassing, 4.0 g (9.7 mmol) of 2-dicyclohexylphosphino-2',6'-dimeth oxybiphenyl (S-phos), tris(dibenzylidene Add 2.2 g (2.4 mmol) of bis(acetone)dipalladium(0), and stir at 130 °C for 40 hours under a nitrogen stream. After the predetermined time has elapsed, subject the obtained reaction mixture to extraction with toluene for purification. Then, purify by silica column chromatography. The developing solvent used was hexane:ethyl acetate = 10:1. Concentrate the obtained fraction to obtain 4.5 g of the target orange solid in a yield of 9%. The synthetic scheme of Step 2 is shown in the following formula (D -2). -2).

[0437]

Chemical formula

[0438] <Step 3; Synthesis of 3,5 - Diisobutyl - 4 - [N - (1,2 - naphthalenediamine)] benzonitrile> > Add 4.5 g (11 mmol) of 3,5 - diisobutyl - 4 - [N - (2 - nitronaphthyl)amino benzonitrile synthesized in Step 2, 2 mL (110 mmol) of water, and 130 mL of ethanol to a 500 mL three - necked flask and stir. Add 10.4 g (55 mmol) of tin(II) chloride to this mixture, and stir at 80 °C for 7.5 hours under a nitrogen stream. After the predetermined time has elapsed, pour the obtained reaction mixture into 100 mL of 2 M aqueous sodium hydroxide solution and stir at room temperature for 2 hours . Filter the precipitated precipitate by suction filtration, wash with chloroform to obtain a filtrate. Extract the obtained filtrate with chloroform. Then, concentrate the obtained extraction solution to obtain 4.1 g of the target black oily substance in a yield of 99%. The synthetic scheme of Step 3 is shown in the following formula (D - 3). formula (D - 3). formula (D - 3). formula (D - 3).

[0439]

Chemical formula

[0440] <Step 4; 1-(4-Cyano-2,6-diisobutylphenyl)-2-phenyl-1 H-naphtho[1,2-d]imidazole (abbreviation: Hpni-diBuCNp) synthesis> 4.2 g (11 mmol) of 3,5-diisobutyl-4-[N-(1,2-naphthalenediamine )]benzonitrile synthesized in Step 3, 50 mL of acetonitrile, and 1.2 g (11 mmol) of benzaldehyde were placed in a 500 mL three-necked flask and stirred at 100 °C for 8 hours To this mixture, 18 mg (0.11 mmol) of iron(III) chloride was added and stirred at 100 °C for 29 hours. After a predetermined time had elapsed, the resulting reaction mixture was purified by extraction with ethyl acetate Thereafter, the resulting solid was purified by silica column chromatography As the developing solvent, toluene was first used, and then a mixed solvent of toluene:ethyl acetate = 20:1 was used. The obtained fractions were concentrated to obtain 2.9 g of the target black oily substance in a yield of 58%. The synthetic scheme of Step 4 is shown in the following formula (D-4).

[0441]

Chemical formula

[0442] <Step 5; Tris{2-[1-(4-cyano-2,6-diisobutylphenyl)-1 H-naphtho[1,2-d]imidazol-2-yl-κN 3 phenyl-κC}iridium (III) (abbreviation: [Ir(pni-diBuCNp) 3 ) synthesis> 1-(4-Cyano-2,6-diisobutylphenyl)-synthesized by the method of Steps 1 to 4 2-Phenyl-1H-naphtho[1,2-d]imidazole 2.9 g (6.3 mmol), tris(acetylacetonato)iridium(III) 0.62 g (1.3 mmol) were placed in a reaction vessel equipped with a three-way cock and heated at 250 °C for 56 hours. The resulting reaction mixture was filtered after adding toluene to remove insoluble substances. The obtained filtrate was concentrated, and a solid was obtained. The obtained solid was purified by silica column chromatography. The developing solvent used was toluene. The obtained fractions were concentrated to obtain a solid. The obtained solid was recrystallized from ethyl acetate / hexane to obtain 0.33 g of a yellow solid in a yield of 16%. The synthetic scheme is shown in the following formula D-5).

[0443]

Chemical formula

[0444] 0.32 g of the obtained solid was purified by sublimation using the train sublimation method. The sublimation purification was performed by heating at 345 °C for 17 hours under the conditions of a pressure of 2.5 Pa and an argon flow rate of 10.4 mL / min. After sublimation purification, 0.10 g was obtained at a recovery rate of 31%.

[0445] The 1 1H-NMR of the yellow solid obtained above was measured. The values obtained are shown below. Also, 1 the 1H-NMR chart is shown in Fig. 17. From Fig. 17, it was found that the organometallic complex of one embodiment of the present invention, [Ir(pni-diBuCNp) 3 was obtained.

[0446] 1 1H-NMR. δ (ppm from CH 2 Cl 2 ),(CD 2 Cl2 ): -0.38 (d, 3H), -0.13--0.06 (m, 9H), 0.35 (d, 3H), 0.41 -0.45 (m, 6H), 0.54 - 0.57 (m, 6H), 0.62 - 0.65 (m, 6H), 0.70 (d, 3H), 1.14 - 1.23 (m, 1H), 1.27 - 1.35 (m, 1H), 1.40 - 1.49 (m, 1H), 1.50 - 1.57 (m, 1H), 1 .60 - 1.66 (m, 2H), 1.71 - 1.90 (m, 4H), 2.06 - 2.15 (m, 2H), 2.22 - 2.31 (m, 4H), 2.33 - 2.42 (t, 2H), 6 .32 - 6.39 (m, 3H), 6.53 - 6.85 (m, 12H), 6.96 (t, 2 H), 7.06 (d, 1H), 7.10 - 7.37 (m, 9H), 7.66 - 7.83( m, 9H).

[0447] Subsequently, the absorption spectrum, emission spectrum, and emission quantum yield of a deoxygenated dichloromethane solution of [Ir(pni - diBuCNp) 3 (0.00 84 mmol / L) were measured. The measurement results of the absorption spectrum and emission spectrum are shown in Fig. 18.

[0448] As shown in Fig. 18, the iridium complex [Ir(pni - diBuCNp) 3 has emission peaks at 510 and 547 nm, and green emission was observed from the deoxygenated dichloromethane solution.

[0449] Also, when the emission quantum yield at an excitation wavelength of 450 nm in a deoxygenated dichloromethane solution (0.0084 mmol / L) was measured, it was found to be very high at 91%.

Example

[0450] ​​ Synthesized as described above, [Ir(pni-diBup) 3 , [Ir(pni-diBu p) 2 (mdppy)], [Ir(pni-diBuCNp) 3 were measured for their photoluminescence quantum yields. Also, the photoluminescence quantum yield of the comparative substance (OC-6-22)-tris{2-[1-(2,6-di isobutylphenyl)-1H-benzimidazol-2-yl-κN phenyl-κC} 3 iridium(III) (abbreviation: fac-[Ir(pbi-diBup) was also measured. The measurement was carried out in the same manner as the method described in Example 1. The results are shown in Table 1. 3 was also measured. The measurement was carried out in the same manner as the method described in Example 1. The results are shown in Table 1. The measurement was carried out in the same manner as the method described in Example 1. The results are shown in Table 1.

[0451]

Table 1

[0452] The difference in the structure between the organometallic complex of one embodiment of the present invention, [Ir(pni-diBup) 3 , and fac-[I r(pbi-diBup) 3 lies in whether or not it has a benzene ring fused at the g-position of the benzimidazole skeleton. As shown in Table 1, the organometallic complex of one embodiment of the present invention shows a better photoluminescence quantum yield. Also, the organometallic complex having a 1H-naphtho[1,2-d]imidazole skeleton as a ligand was found to show a very high photoluminescence quantum yield exceeding 90%. The difference in the structure between the organometallic complex of one embodiment of the present invention, [Ir(pni-diBup) , and fac-[I r(pbi-diBup) lies in whether or not it has a benzene ring fused at the g-position of the benzimidazole skeleton. As shown in Table 1, the organometallic complex of one embodiment of the present invention shows a better photoluminescence quantum yield. Also, the organometallic complex having a 1H-naphtho[1,2-d]imidazole skeleton as a ligand was found to show a very high photoluminescence quantum yield exceeding 90%.

Examples

[0453] In this example, the fabrication examples of a light-emitting device and a comparative light-emitting device including an organic compound according to one embodiment of the present invention, and the characteristics of the light-emitting device will be described. The stacked structure of the light-emitting device fabricated in this example is shown in As shown in Fig. 1(A). The details of the device structure are shown in Table 2. The organic compound used in this example is shown below. For other organic compounds, refer to other embodiments or examples. The compounds are shown below. For other organic compounds, refer to other embodiments or examples. should suffice.

[0454] [Chemical formula]

[0455] [Table 2]

[0456] [Fabrication of Comparative Light-Emitting Device 1] As electrode 101 on a glass substrate, an ITSO film was formed by sputtering to a thickness of 70 nm. The electrode area of electrode 101 was 4 mm (2 mm × 2 mm) 2 and formed. Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water, dried at 2 00 °C for 1 hour, and then subjected to UV ozone treatment for 370 seconds. Thereafter, the substrate was placed in a vacuum evaporation apparatus maintained at a vacuum degree of about 1 × 10 -4 Pa, and baked at 170 °C for 30 minutes. Thereafter, the substrate was allowed to cool for about 30 minutes.

[0457] Next, as hole injection layer 111 on electrode 101, DBT3P-II and molybdenum (VI) oxide (MoO (VI) (MoO 3 ) were co-evaporated so that the weight ratio (DBT3P-II:MoO 3 ) was 1:0.5 and the thickness was 40 nm.

[0458] Next, as hole transport layer 112 on hole injection layer 111, PCCP was deposited to a thickness of 20 nm. and

[0459] Next, as the light-emitting layer 140, 4,6mCzP2Pm and PCCP were co-evaporated on the hole transport layer 112 and [Ir(ppy) 3 such that the weight ratio (4,6mCzP2Pm:PCCP:[Ir(pp y) 3 ) was 0.6:0.4:0.1 and the thickness was 40 nm. In the light-emitting layer 140, [Ir(ppy) is a guest material that exhibits phosphorescent emission. 3 is a guest material that exhibits phosphorescent emission. is a guest material that exhibits phosphorescent emission.

[0460] Next, on the light-emitting layer 140, 4,6mCzP2Pm was evaporated to a thickness of 20 nm as the electron transport layer 118(1). Next, on the electron transport layer 118(1), NBPhen was sequentially evaporated to a thickness of 10 nm as the electron transport layer 118 (2). (2).

[0461] Next, on the electron transport layer 118, LiF was evaporated to a thickness of 1 nm as the electron injection layer 119. Next, on the electron transport layer 118, LiF was evaporated to a thickness of 1 nm as the electron injection layer 119.

[0462] Next, on the electron injection layer 119, aluminum (Al) was formed to a thickness of 20 0 nm as the electrode 102.

[0463] Next, in a glove box under a nitrogen atmosphere, in order to seal using a sealing material, a substrate (opposite substrate) different from the substrate on which the light-emitting element was formed was fixed to the substrate on which the light-emitting element was formed, thereby sealing the comparative light-emitting element 1. Specifically, a desiccant was attached to the opposite substrate, and further, the opposite substrate to which the sealing material was applied around the range where the light-emitting element was formed and the glass substrate on which the light-emitting element was formed were bonded together, and ultraviolet light with a wavelength of 365 nm was irradiated at 6 J / cm thereby sealing the comparative light-emitting element 1. Specifically, a desiccant was attached to the opposite substrate, and further, the opposite substrate to which the sealing material was applied around the range where the light-emitting element was formed and the glass substrate on which the light-emitting element was formed were bonded together, and ultraviolet light with a wavelength of 365 nm was irradiated at 6 J / cm thereby sealing the comparative light-emitting element 1. Specifically, a desiccant was attached to the opposite substrate, and further, the opposite substrate to which the sealing material was applied around the range where the light-emitting element was formed and the glass substrate on which the light-emitting element was formed were bonded together, and ultraviolet light with a wavelength of 365 nm was irradiated at 6 J / cm and heat-treated at 80 °C for 1 hour. The comparative light-emitting element 1 was obtained through the above steps. 2 and heat-treated at 80 °C for 1 hour. The comparative light-emitting element 1 was obtained through the above steps. and heat-treated at 80 °C for 1 hour. The comparative light-emitting element 1 was obtained through the above steps.

[0464] <<Fabrication of Comparative Light-Emitting Element 2, Comparative Light-Emitting Element 3, and Light-Emitting Element 4>> The fabrication processes of Comparative Light-Emitting Element 2, Comparative Light-Emitting Element 3, and Light-Emitting Element 4 are only different from the fabrication process of Comparative Light-Emitting Element 1 and the fabrication process of the light-emitting layer 140 shown above, and the other fabrication processes are the same as those of Comparative Light-Emitting Element 1. The element structures of Comparative Light-Emitting Element 2, Comparative Light-Emitting Element 3, and Light-Emitting Element 4 are as shown in Table 2, so the detailed fabrication processes are omitted. The light-emitting layer 140 of Comparative Light-Emitting Element 2, Comparative Light-Emitting Element 3, and Light-Emitting Element 4 was formed by vacuum evaporation in the same manner as Comparative Light-Emitting Element 1. For Comparative Light-Emitting Element 1 to Comparative Light-Emitting Element 3 and Light-Emitting Element 4, the element structures are only different in the guest materials used for the light-emitting layer 140, and the other configurations are the same for all the light-emitting elements. Note that Light-Emitting Element 4 uses [Ir(pni-diBup) , which is an organic compound of one aspect of the present invention, and Comparative Light-Emitting Element 3 uses fac-[Ir(pbi-diBup)

[0465] , which is a comparative substance. Also, for Comparative Light-Emitting Element 1 and Comparative Light-Emitting Element 2, [Ir(ppy) and GD270 (manufactured by Jilin OLED Co., Ltd.), which are widely used as guest materials, are used respectively. 3 . 3 . 3 and GD270 (manufactured by Jilin OLED Co., Ltd.) were used respectively.

[0466] <Characteristics of the Light-Emitting Element> Next, the characteristics of Comparative Light-Emitting Element 1 to Comparative Light-Emitting Element 3 and Light-Emitting Element 4 fabricated above were measured. A color luminance meter (Topcon Corporation, BM-5A) was used for measuring the luminance and CIE chromaticity, and a multi-channel spectroscope (Hamamatsu Photonics, PMA- 11) was used for measuring the electroluminescence spectrum.

[0467] ​​​​​​​​The current efficiency-luminance characteristics of Comparative Light-Emitting Element 1 to Comparative Light-Emitting Element 3 and Light-Emitting Element 4 are shown in Fig. 19. . Further, the current density-voltage characteristics are shown in Fig. 20. Further, the external quantum efficiency-luminance characteristics are shown in Fig. 21 . The measurement of each light-emitting element was carried out at room temperature (an atmosphere maintained at 23°C). Also, Comparative Light-Emitting Element 1 to Comparative Light-Emitting Element 3 and Light-Emitting Element 4 were passed with a current at a current density of 2.5 mA / cm 2 . The emission spectrum when the current was passed is shown in Fig. 22.

[0468] Also, Table 3 shows the element characteristics of Comparative Light-Emitting Element 1 to Comparative Light-Emitting Element 3 and Light-Emitting 2 Element 4 in the vicinity of 1000 cd / m .

[0469]

Table 3

[0470] Also, from Fig. 22, the emission spectra of Comparative Light-Emitting Element 1 to Comparative Light-Emitting Element 3 and Light-Emitting Element 4 each have a spectral peak at around 518 nm, 523 nm, 508 nm, and 500 nm, and the full width at half maximum is about 74 nm, 73 nm, 63 nm, and 27 nm, respectively. Therefore , it was found that Comparative Light-Emitting Element 1 to Comparative Light-Emitting Element 3 and Light-Emitting Element 4 each have emission derived from the guest material of the respective light-emitting elements.

[0471] As shown in Fig. 19 and Table 3, Comparative Light-Emitting Element 1 to Comparative Light-Emitting Element 3 and Light-Emitting Element 4 all showed high current efficiency. Light-Emitting Element 4 has an emission spectrum in a region with low visibility (short-wavelength region) compared to Comparative Light-Emitting Element 1 to Comparative Light-Emitting Element 3, but has a current efficiency equivalent to that of Comparative Light-Emitting Element 1 to Comparative Light-Emitting Element 3. Also, as shown in Fig. 21 and Table 3 It was found that the light-emitting element 4 has a very high efficiency with an external quantum efficiency exceeding 25%. In addition, the light-emitting element 4 is widely used as a guest material [Ir(ppy) 3 or showed higher efficiency than the comparative light-emitting element 1 and the comparative light-emitting element 2 using GD270. Also, the light-emitting element 4 has light emission on the shorter wavelength side than the light-emitting element 3, but has an external quantum efficiency equal to or higher than that.

[0472] As shown in FIG. 20 and Table 3, the comparative light-emitting element 1 to the comparative light-emitting element 3 and the light-emitting element 4 were found to have good driving voltage characteristics respectively.

Example

[0473] In this example, a production example of a light-emitting element different from Example 6, including an organometallic complex according to an aspect of the present invention, and the characteristics of the light-emitting element will be described. The stacked structure of the light-emitting element fabricated in this example is shown in FIG. 1(A). Also, the details of the element structure are shown in Table 4. Also, the organic compounds used in this example are shown below. For other organic compounds, other embodiments or examples may be referred to.

[0474]

Chemical formula

[0475]

Table 4

[0476] ≪Fabrication of the light-emitting element 5≫ The light-emitting element 5 was fabricated by vapor deposition in the same manner as the comparative light-emitting element 1 to the comparative light-emitting element 3 and the light-emitting element 4 shown above. Since the element structure of the light-emitting element 5 is as shown in Table 4, detailed fabrication ​​​​The manufacturing process will be omitted. The light-emitting element 5 is a light-emitting element using a heteroorganic metal complex (a metal complex having two or more ligands) according to one aspect of the present invention.

[0477] <Characteristics of the light-emitting element> Next, the characteristics of the fabricated light-emitting element 5 were measured. The measurement conditions of the light-emitting element were the same as those in the previous examples.

[0478] The current efficiency-luminance characteristics of the light-emitting element 5 are shown in Fig. 23. Also, the current density-voltage characteristics are shown in Fig. 24. In addition, the external quantum efficiency-luminance characteristics are shown in Fig. 25. Also, the emission spectrum of the light-emitting element 5 when a current of 2.5 mA / cm 2 is passed is shown in Fig. 26.

[0479] Moreover, Table 5 shows the element characteristics of the light-emitting element 5 in the vicinity of 1000 cd / m 2 .

[0480]

Table 5

[0481] Also, from Fig. 26, the emission spectrum of the light-emitting element 5 has a spectral peak at around 523 nm, and the full width at half maximum is about 63 nm. Therefore, it was found that the light-emitting element 5 emits light derived from the guest material [Ir(pn i-diBup) 2 (mdppy)].

[0482] As shown in Fig. 23, Fig. 25, and Table 5, the light-emitting element 5 showed high current efficiency and external quantum efficiency. In particular, a very high efficiency exceeding 25% was obtained for the external quantum efficiency.

[0483] As shown in Fig. 24 and Table 5, it was found that the light-emitting element 5 has good driving voltage characteristics. . Light was shown.

[0484] <Reliability of Light-Emitting Element> Next, a constant current drive test of the light-emitting element 5 at 2 mA was conducted. The results are shown in FIG. 27. From FIG. 27, the light-emitting element 5 has an LT 70 (Luminance 30% reduction time) exceeding 100 hours, and it was found to have good reliability.

Example

[0485] In this example, an example of manufacturing a light-emitting element different from those of Examples 6 and 7, which includes an organometallic complex according to an aspect of the present invention, and the characteristics of the light-emitting element will be described. The stacked structure of the light-emitting element manufactured in this example is shown in FIG. 1(A). In addition, the details of the element structure are shown in Table 6.

[0486]

Table 6

[0487] ≪Fabrication of Comparative Light-Emitting Elements 6 and 7≫ The comparative light-emitting element 6 and the light-emitting element 7 were formed by vacuum deposition in the same manner as the light-emitting element 5 shown above. Since the element structures of the comparative light-emitting element 6 and the light-emitting element 7 are as shown in Table 6, the detailed manufacturing process will be omitted. The light-emitting element 7 is a light-emitting element using [Ir(pni-diBuCNp) which is an organometallic complex of an aspect of the present invention as a guest material. Note that the comparative light-emitting element 6 is a light-emitting element using GD270 as a guest material.

[0488] 3 as a guest material.

[0488] <Characteristics of Light-Emitting Element> Next, the characteristics of the comparative light-emitting element 6 and the light-emitting element 7 manufactured above were measured. The measurement conditions of the light-emitting element were the same as those of the examples shown above.

[0489] ​​​The current efficiency-luminance characteristics of the comparative light-emitting element 6 and the light-emitting element 7 are shown in Fig. 28. Also, the current density- voltage characteristics are shown in Fig. 29. Also, the external quantum efficiency-luminance characteristics are shown in Fig. 30. Also, the comparative light- emitting element 6 and the light-emitting element 7 were driven at a current density of 2.5 mA / cm 2 to obtain the emission spectra, which are shown in Fig. 31.

[0490] Also, the device characteristics of the comparative light-emitting element 6 and the light-emitting element 7 near 1000 cd / m 2 are shown in Table 7.

[0491]

Table 7

[0492] From Fig. 31, the emission spectra of the comparative light-emitting element 6 and the light-emitting element 7 have spectral peaks at around 523 nm and 510 nm, respectively, and the full widths at half maximum are about 68 nm and 67 nm, respectively. Therefore, it was found that the light emission obtained from the comparative light-emitting element 6 and the light-emitting element 7 is derived from the guest materials of the respective light-emitting elements.

[0493] As shown in Fig. 28, Fig. 30, and Table 7, both the comparative light-emitting element 6 and the light-emitting element 7 showed high current efficiency. Although the light-emitting element 7 has an emission spectrum in a region with low visibility (short-wavelength region) compared to the comparative light-emitting element 6, it has a higher current efficiency than the comparative light-emitting element 6. Also, as shown in Fig. 30 and Table 7, it was found that the light-emitting element 7 has an extremely high efficiency with an external quantum efficiency exceeding 25%. Also, although the light-emitting element 7 emits light on the shorter wavelength side than the comparative light-emitting element 6 using GD270 widely used as a guest material, it showed higher current efficiency and external quantum efficiency than the comparative light-emitting element 6. ​

[0494] As shown in FIG. 29 and Table 7, it was found that the comparative light-emitting element 6 and the light-emitting element 7 each have good drive voltage characteristics.

Explanation of Signs

[0495] 100: EL layer, 101: electrode, 102: electrode, 103: EL layer, 106: light-emitting unit , 108: light-emitting unit, 111: hole injection layer, 112: hole transport layer, 113: electron transport layer, 114: electron injection layer, 115: charge generation layer, 116: hole injection layer, 117: hole transport layer, 118: electron transport layer, 119: electron injection layer, 120: light-emitting layer, 140: light-emitting layer, 14 1: host material, 141_1: organic compound, 141_2: organic compound, 142: guest material , 150: light-emitting element, 152: light-emitting element, 170: light-emitting layer, 250: light-emitting element, 601 : source-side drive circuit, 602: pixel portion, 603: gate-side drive circuit, 604: sealing substrate, 605: sealing material, 607: space, 608: wiring, 610: element substrate, 611: switching TFT for ring, 612: current control, 613: electrode, 614: insulator, 616: EL layer, 617: electrode, 618: light-emitting element, 623: n-channel TFT, 624: p-channel TFT, 900: portable information terminal, 901: housing, 902: housing, 903: display unit, 905 : hinge portion, 910: portable information terminal, 911: housing, 912: display unit, 913: operation button , 914: external connection port, 915: speaker, 916: microphone, 917: camera, 9 20: camera, 921: housing, 922: display unit, 923: operation button, 924: shutter button, 926: lens, 1001: substrate, 1002: underlying insulating film, 1003: gate Insulating film, 1006: Gate electrode, 1007: Gate electrode, 1008: Gate electrode, 102 0: Interlayer insulating film, 1021: Interlayer insulating film, 1022: Electrode, 1024B: Electrode, 1024 G: Electrode, 1024R: Electrode, 1025B: Lower electrode, 1025G: Lower electrode, 1025 R: Lower electrode, 1026: Partition wall, 1028: EL layer, 1029: Electrode, 1031: Sealing base plate, 1032: Sealant, 1033: Substrate, 1034B: Coloring layer, 1034G: Coloring layer, 1034R: Coloring layer, 1036: Overcoat layer, 1037: Interlayer insulating film, 1040: Pixel portion, 1041: Driving circuit portion, 1042: Peripheral portion, 2100: Robot, 2101: Illumination sensor, 2102: Microphone, 2103: Upper camera, 2104: Speaker, 2 105: Display, 2106: Lower camera, 2107: Obstacle sensor, 2108: Movement mechanism, 2110: Arithmetic unit, 3500: Multifunctional terminal, 3502: Housing, 3504: Display section, 3506: Camera, 3508: Lighting, 3600: Light, 3602: Housing, 3608 : Lighting, 3610: Speaker, 5000: Housing, 5001: Display section, 5002: Display section, 5003: Speaker, 5004: LED lamp, 5005: Operation key, 5006: Connection terminal 5007: Sensor, 5008: Microphone, 5012: Support portion, 5013: Ear phone, 5100: Cleaning robot, 5101: Display, 5102: Camera, 5103 : Brush, 5104: Operation button, 5120: Dust, 5140: Portable electronic device, 5150 : Portable information terminal, 5151: Housing, 5152: Display area, 5153: Bending portion, 8501: Lighting device, 8502: Lighting device, 8503: Lighting device, 8504: Lighting device, 9000: Housing, 9001: Display section, 9006: Connection terminal, 9055: Hinge, 9200: Portable information Terminal, 9201: Mobile Information Terminal, 9202: Mobile Information Terminal

Claims

1. An organic compound represented by general formula (g-1): 【Chemistry 1】 In general formula (g-1), R １ ~R １０ each independently represents any one of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a halogeno group, a cyano group, a nitro group, a carbonyl group, and a haloalkyl group, and Ar represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

2. In claim 1, Ar is an organic compound represented by any one of the following formulas (Ar-1) to (Ar-25). 【Chemistry 2】

3. In claim 1, Ar is an organic compound that is a substituted or unsubstituted phenyl group.

4. In claim 3, An organic compound in which the substituent in Ar is an alkyl group having 1 to 6 carbon atoms.

5. In claim 3, An organic compound in which the substituent in Ar is a branched alkyl group having 3 to 7 carbon atoms.

6. An organic compound represented by the following formula: 【Chemistry 3】

7. An organic compound represented by the following formula: 【Chemistry 4】

8. An organic compound represented by the following formula: 【Chemistry 5】

9. An organic compound represented by the following formula: 【Chemistry 6】

10. An organic compound represented by the following formula: 【Chemistry 7】

11. An organic compound represented by the following formula: 【Chemistry 8】

12. An organic compound represented by the following formula: 【Chemistry 9】

13. An organic compound represented by the following formula: 【Chemistry 10】

14. An organic compound represented by the following formula: 【Chemistry 11】

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