Light emitting device

Abstract

NOVEL ORGANOMETALLIC COMPLEX HAVING EXCELLENT HEAT RESISTANCE SOLUTION: The organometallic complex includes iridium and a ligand, and the ligand has a structure represented by General Formula (G1) in which iridium is bonded to a nitrogen atom at the 1-position of a pyrazine skeleton, phenyl groups having alkyl groups as substituents are bonded to the 2 - and 3-positions of the pyrazine skeleton, phenyl groups having cyano groups as substituents are bonded to the 5-position of the pyrazine skeleton, and the phenyl groups bonded to the 2-position of the pyrazine skeleton are ortho-metalated with iridium.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] One aspect of the present invention relates to an organometallic complex. The present invention also relates to an organometallic complex that can be converted into light-emitting material. It should be noted that one aspect of the present invention is not limited to the above technical fields. The technical field of one embodiment of the invention disclosed in the present specification and the like is related to an object, a method, or a manufacturing method. Alternatively, one aspect of the present invention relates to a process, a machine, a manufacture It is about cha, or composition of matter. More specifically, the technical field of one embodiment of the present invention disclosed in this specification includes, in addition to the above, Semiconductor devices, display devices, liquid crystal display devices, power storage devices, storage devices, and methods for driving them, or The manufacturing method thereof can be cited as an example. [Background technology]

[0002] A light-emitting element (also called an organic EL element) has an organic compound that is a light-emitting substance between a pair of electrodes. It has characteristics such as thinness, light weight, high-speed response, and low voltage operation, so it is Sprays are attracting attention as a next-generation flat panel display. When a voltage is applied, electrons and holes injected from the electrodes recombine, resulting in The luminescent substance is excited and emits light when the excited state returns to the ground state. The types of states include the singlet excited state (S * ) and triplet excited states (T * ) and singlet Light emitted from the excited state is called fluorescence, and light emitted from the triplet excited state is called phosphorescence. The statistical generation rate of these in optical devices is S* :T * It is believed that the ratio is 1:3. do.

[0003] Among the above-mentioned luminescent materials, those capable of converting energy in a singlet excited state into luminescence are also The compounds that can be produced are called fluorescent compounds (fluorescent materials), and they emit light with triplet excited energy. Compounds that can convert light into light are called phosphorescent compounds (phosphorescent materials).

[0004] Therefore, based on the above generation ratio, the internal The theoretical limit of quantum efficiency (the ratio of photons generated to injected carriers) is If a fluorescent material is used, the percentage is 25%, and if a phosphorescent material is used, the percentage is 75%.

[0005] That is, a light-emitting element using a phosphorescent material has a higher luminance than a light-emitting element using a fluorescent material. Therefore, in recent years, the development of various types of phosphorescent materials has become active. In particular, due to its high phosphorescence quantum yield, it is widely used in fluorescent materials with iridium as the central metal. Organometallic complexes have been attracting attention (for example, Patent Document 1). [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Japanese Patent Application Laid-Open No. 2009-23938 Summary of the Invention [Problem to be solved by the invention]

[0007] As reported in the above-mentioned Patent Document 1, the development of phosphorescent materials that exhibit excellent properties has progressed. However, there is a need to develop new materials that exhibit even better properties.

[0008] Thus, one embodiment of the present invention provides a novel organometallic complex. The present invention provides a novel organometallic complex having excellent heat resistance. In addition, in one embodiment of the present invention, a novel organometallic complex is provided that exhibits little decomposition when used in a photoluminescent device. Furthermore, in one embodiment of the present invention, a novel organometallic complex that can be used in a light-emitting element is provided. In addition, in one embodiment of the present invention, a novel organometallic complex capable of In addition, in one embodiment of the present invention, a novel organometallic complex is provided, which can be used for the layer. A novel light-emitting element is provided. Also, a novel light-emitting device, a novel electronic device, or a novel lighting device is provided. The present invention provides a device for detecting a temperature difference between a semiconductor device and a semiconductor substrate. One embodiment of the present invention does not necessarily solve all of these problems. Other issues will become clear from the description, drawings, claims, etc. It is possible to extract other issues from the description, drawings, claims, etc. be. [Means for solving the problem]

[0009] One embodiment of the present invention includes an iridium compound and a ligand, the ligand having a pyrazine skeleton, The pyrazine skeleton has 2, 3, and 5 nitrogen atoms attached to the pyrazine skeleton. A phenyl group is bonded to each of the 2- and 3-positions, and the phenyl groups bonded to the 3-position are The phenyl group bonded to the 5-position has an alkyl group as a substituent, and the phenyl group bonded to the 5-position has a cyano group as a substituent. The organometallic complex is characterized by:

[0010] Another aspect of the present invention is a compound comprising a first ligand, a second ligand, and a cation bonded to iridium. The first ligand has a pyrazine skeleton, and the iridium and the nitrogen at the 1-position of the pyrazine skeleton are bonded to each other. The pyrazine skeleton has phenyl groups attached to the 2, 3, and 5 positions, The phenyl groups bonded to the 2nd and 3rd positions each have an alkyl group as a substituent, and The phenyl group attached to the position has a cyano group as a substituent, and the second ligand is a monoanion. In particular, the second ligand is an organometallic complex characterized by a carboxylic acid. , a monoanionic bidentate chelating ligand having a β-diketone structure, Monoanionic bidentate chelating ligands with phenolic hydroxyl groups or a monoanionic bidentate chelating ligand in which both coordination elements are nitrogen. Aromatic ligands that form metal-carbon bonds with iridium via chelating or cyclometallation Preferably, the ligand is a heterocyclic bidentate ligand.

[0011] In the above structure, the phenyl group bonded to the 5-position of the pyrazine skeleton may be an alkyl group. In particular, it is preferable that at least one of the phenyl groups bonded to the 5-position of the pyrazine skeleton is By introducing an alkyl group at the 2-position, the emission spectrum is prevented from shifting too far to the long wavelengths. This prevents the color from fading and maintains visibility. In other words, it is possible to obtain a deep red color with high color purity and high efficiency. It is particularly suitable for

[0012] Another embodiment of the present invention is an organometallic complex having a structure represented by the following general formula (G1): be.

[0013] [ka]

[0014] However, in the general formula (G1), A 1 ~A 4 each independently represents the number of substituted or unsubstituted carbon atoms represents an alkyl group having 1 to 6 carbon atoms; R 1 ~R 6 are each independently hydrogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, or an unsubstituted heteroaryl group having 3 to 12 carbon atoms. 7 ~R 11 are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted aryl groups having 3 to 12 carbon atoms It represents either a heteroaryl group or a cyano group, and at least one represents a cyano group.

[0015] Another embodiment of the present invention is an organometallic complex having a structure represented by the following general formula (G2): be.

[0016] [ka]

[0017] However, in the general formula (G2), A 1 ~A 4 are each independently the number of substituted or unsubstituted carbon atoms represents an alkyl group having 1 to 6 carbon atoms; R 6 is hydrogen, substituted or unsubstituted alkyl having 1 to 6 carbon atoms aryl groups, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms R represents any one of the heteroaryl groups of 3 to 12. 7 ~R 11 are each independently , hydrogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms, sialic acid groups, At least one of the groups represents a cyano group.

[0018] Another embodiment of the present invention is an organometallic complex represented by the following general formula (G3).

[0019] [ka]

[0020] However, in the general formula (G3), A 1 ~A 4 are each independently the number of substituted or unsubstituted carbon atoms represents an alkyl group having 1 to 6 carbon atoms; R 1 ~R 6 are each independently hydrogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, or an unsubstituted heteroaryl group having 3 to 12 carbon atoms. 7 ~R 11 are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted aryl groups having 3 to 12 carbon atoms L represents either a heteroaryl group or a cyano group, and at least one of L represents a cyano group. , represents a monoanionic ligand.

[0021] Another embodiment of the present invention is an organometallic complex represented by the following general formula (G4).

[0022] [ka]

[0023] However, in general formula (G4), A 1 ~A 4are each independently the number of substituted or unsubstituted carbon atoms represents an alkyl group having 1 to 6 carbon atoms; R 6 is hydrogen, substituted or unsubstituted alkyl having 1 to 6 carbon atoms aryl groups, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms R represents any one of the heteroaryl groups of 3 to 12. 7 ~R 11 are each independently , hydrogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms, sialic acid groups, At least one of L represents a cyano group. Represents a child.

[0024] In each of the above structures, the monoanionic ligand is a monoanionic ligand having a β-diketone structure. Anionic bidentate chelating ligands, monoanionic bidentate chelating ligands with carboxyl groups a monoanionic bidentate chelating ligand having a phenolic hydroxyl group, or A monoanionic bidentate chelating ligand in which both coordination elements are nitrogen, or a cyclometa It is an aromatic heterocyclic bidentate ligand that forms a metal-carbon bond with iridium upon oxidation. It is characterized by:

[0025] In each of the above structures, the monoanionic ligand is represented by the following general formulas (L1) to (L6): The present invention is characterized in that the present invention is any one of the above.

[0026] [ka]

[0027] However, in general formulas (L1) to (L6), R 71 ~R 94are each independently hydrogen or substituted. or unsubstituted alkyl group having 1 to 6 carbon atoms, halogen group, vinyl group, substituted or unsubstituted a 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. 1 ~A 3 teeth, sp bonded independently to nitrogen or hydrogen 2 Hybridized carbon or substituted sp 2 represents a hybrid carbon, and the substituent is an alkyl group having 1 to 6 carbon atoms, a halogen group, a represents a haloalkyl group or a phenyl group, B 1 ~B 8 are each independently a nitrogen or a substituent represents a substituted or unsubstituted carbon, and the substituent is an alkyl group having 1 to 6 carbon atoms, a halogen group, It represents a haloalkyl group having 1 to 6 carbon atoms or a phenyl group.

[0028] Another embodiment of the present invention is an organometallic complex represented by the following general formula (G5).

[0029] [ka]

[0030] However, in general formula (G5), A 1 ~A 4 are each independently the number of substituted or unsubstituted carbon atoms represents an alkyl group having 1 to 6 carbon atoms; R 1 ~R 6 are each independently hydrogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, or an unsubstituted heteroaryl group having 3 to 12 carbon atoms. 7 ~R 11are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted aryl groups having 3 to 12 carbon atoms It represents either a heteroaryl group or a cyano group, and at least one represents a cyano group.

[0031] Another embodiment of the present invention is an organometallic complex represented by the following general formula (G6).

[0032] [ka]

[0033] However, in general formula (G6), A 1 ~A 4 are each independently the number of substituted or unsubstituted carbon atoms represents an alkyl group having 1 to 6 carbon atoms; R 6 is hydrogen, substituted or unsubstituted alkyl having 1 to 6 carbon atoms aryl groups, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms R represents any one of the heteroaryl groups of 3 to 12. 7 ~R 11 are each independently , hydrogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms, sialic acid groups, At least one of the groups represents a cyano group.

[0034] Another embodiment of the present invention is an organometallic complex represented by the following general formula (G7).

[0035] [ka]

[0036] However, in general formula (G7), A 1 ~A4 are each independently the number of substituted or unsubstituted carbon atoms represents an alkyl group having 1 to 6 carbon atoms; R 1 ~R 6 are each independently hydrogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, or an unsubstituted heteroaryl group having 3 to 12 carbon atoms. 7 ~R 11 are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted aryl groups having 3 to 12 carbon atoms It represents either a heteroaryl group or a cyano group, and at least one represents a cyano group.

[0037] Another embodiment of the present invention is an organometallic complex represented by the following general formula (G8).

[0038] [ka]

[0039] However, in general formula (G8), A 1 ~A 4 are each independently the number of substituted or unsubstituted carbon atoms represents an alkyl group having 1 to 6 carbon atoms; R 6 is hydrogen, substituted or unsubstituted alkyl having 1 to 6 carbon atoms aryl groups, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms R represents any one of the heteroaryl groups of 3 to 12. 7 ~R 11 are each independently , hydrogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms, sialic acid groups, At least one of the groups represents a cyano group.

[0040] In the above general formulas (G1) to (G8), R 7 ~R 11 At least one of the carbon numbers It is preferable that the alkyl group has a carbon number of 1 to 6. In particular, the emission spectrum peak is in the long wavelength region. To prevent this from happening too much and maintain visibility, 7 or R 11 At least one of Preferably, the alkyl group is an alkyl group having 1 to 6 carbon atoms. It is particularly suitable for obtaining a high and highly efficient deep red color.

[0041] Another embodiment of the present invention is an organometallic complex represented by the following structural formula (100):

[0042] [ka]

[0043] In addition, the organometallic complex according to one embodiment of the present invention can emit phosphorescence, i.e., triple phosphorescence. Since it is possible to obtain light emission from the excited state and to exhibit light emission, it is suitable for light emitting devices. By using this method, it is possible to achieve high efficiency, which is very effective. A light-emitting element using such an organometallic complex is included in one embodiment of the present invention.

[0044] Another embodiment of the present invention is a liquid crystal display device including an EL layer between a pair of electrodes, the EL layer including a light-emitting layer, The light-emitting layer is a light-emitting element having any of the organometallic complexes described above.

[0045] Another embodiment of the present invention is a liquid crystal display device including an EL layer between a pair of electrodes, the EL layer including a light-emitting layer, The light-emitting layer contains a plurality of organic compounds, one of which is the organic metal compound described above. The light-emitting device is one of the group complexes.

[0046] Note that one embodiment of the present invention is not only a light-emitting device having a light-emitting element, but also a lighting device having a light-emitting device. Therefore, the light-emitting device in this specification includes an image display device. It also refers to a light source (including lighting equipment) with a connector, such as an FP C (Flexible printed circuit) or TCP (Tape Module with Carrier Package attached, printed on TCP A module with a wiring board or a light emitting element with COG (Chip On Glass) ) method, all modules in which ICs (integrated circuits) are directly mounted are also included in the light-emitting device. do. [Effects of the Invention]

[0047] According to one embodiment of the present invention, a novel organometallic complex can be provided. In this manner, a novel organometallic complex having excellent heat resistance can be provided. In one embodiment, a novel organometallic complex that is less decomposed during sublimation can be provided. According to one embodiment of the present invention, a novel organometallic complex with high color purity can be provided. One embodiment of the present invention is to provide a novel organometallic complex that can be used in a light-emitting element. In addition, in one embodiment of the present invention, a novel compound that can be used in an EL layer of a light-emitting element can be provided. It is possible to provide a novel organometallic complex. Furthermore, a novel light-emitting device, a novel electronic device, or a novel lighting device can be provided. It should be noted that the description of these effects does not preclude the existence of other effects. Furthermore, it is not necessary for one embodiment of the present invention to have all of these effects. Furthermore, effects other than these are not obvious from the description, drawings, claims, etc. Other effects can be extracted from the description, drawings, claims, etc. It is possible. [Brief explanation of the drawings]

[0048] [Figure 1] 1A to 1C illustrate a structure of a light-emitting element. [Figure 2] 1A to 1C illustrate a structure of a light-emitting element. [Figure 3] 1A and 1B illustrate a light-emitting device. [Figure 4] 1A and 1B illustrate a light-emitting device. [Figure 5] 1A and 1B are diagrams illustrating electronic devices. [Figure 6] 1A and 1B are diagrams illustrating electronic devices. [Figure 7] FIG. [Figure 8] 1A and 1B are diagrams illustrating a lighting device. [Figure 9] 1A and 1B are diagrams illustrating a lighting device. [Figure 10] FIG. 1 is a diagram showing an example of a touch panel. [Figure 11] FIG. 1 is a diagram showing an example of a touch panel. [Figure 12] FIG. 1 is a diagram showing an example of a touch panel. [Figure 13] 1A and 1B are a block diagram and a timing chart of a touch sensor. [Figure 14] Circuit diagram of a touch sensor. [Figure 15] FIG. [Figure 16] Circuit configuration of the display device. [Figure 17] Cross-sectional structure of a display device. [Figure 18]1H-NMR chart of the organometallic complex shown in structural formula (100). [Figure 19] UV-visible absorption and emission spectra of the organometallic complex shown in structural formula (100). [Figure 20] FIG. 1 shows the results of LC-MS measurement of the organometallic complex represented by structural formula (100). [Figure 21] FIG. 1 is a diagram showing the relationship between partial pressure and mass-to-charge ratio in a quadrupole mass spectrometer. [Figure 22] Thermogravimetric curves of organometallic complexes. [Figure 23] 1A and 1B are diagrams illustrating light-emitting elements. [Figure 24] 10 shows current density-luminance characteristics of the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 3. [Figure 25] 10 shows voltage-luminance characteristics of the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 3. [Figure 26] 10 shows luminance-current efficiency characteristics of the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 3. [Figure 27] 10 shows voltage-current characteristics of the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 3. [Figure 28] 10 is a graph showing CIE chromaticities of the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 3. [Figure 29] 10 shows emission spectra of the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 3. FIG. [Figure 30] 10 shows the reliability of the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 3. [Figure 31] 1A and 1B are diagrams illustrating light-emitting elements. [Figure 32] 1H-NMR chart of the organometallic complex shown in structural formula (108). [Figure 33] UV-visible absorption and emission spectra of the organometallic complex shown in structural formula (108). [Figure 34] 1H-NMR chart of the organometallic complex shown in structural formula (114). [Figure 35] UV-visible absorption and emission spectra of the organometallic complex shown in structural formula (114). [Figure 36] 10 shows current density-luminance characteristics of the light-emitting element 4, the light-emitting element 5, and the comparative light-emitting element 6. FIG. [Figure 37] 10 shows voltage-luminance characteristics of the light-emitting element 4, the light-emitting element 5, and the comparative light-emitting element 6. [Figure 38] 10 shows luminance-current efficiency characteristics of the light-emitting element 4, the light-emitting element 5, and the comparative light-emitting element 6. [Figure 39] 10 shows voltage-current characteristics of the light-emitting element 4, the light-emitting element 5, and the comparative light-emitting element 6. [Figure 40] 10 is a graph showing CIE chromaticities of the light-emitting element 4, the light-emitting element 5, and the comparative light-emitting element 6. [Figure 41] FIG. 10 shows emission spectra of the light-emitting element 4, the light-emitting element 5, and the comparative light-emitting element 6. [Figure 42] 10 shows the reliability of the light-emitting element 4, the light-emitting element 5, and the comparative light-emitting element 6. DETAILED DESCRIPTION OF THE INVENTION

[0049] Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. The present invention is not limited to the above description, and the form and details thereof may be changed without departing from the spirit and scope of the present invention. Therefore, the present invention is not limited to the embodiments described below. It is not to be construed as being limited to the

[0050] The words "film" and "layer" may be used interchangeably depending on the situation. For example, the term "conductive layer" can be replaced with "conductive film." ". Alternatively, for example, the term "insulating film" may be used. It may be possible to change the term to "insulating layer."

[0051] (Embodiment 1) In this embodiment, an organometallic complex which is one embodiment of the present invention will be described.

[0052] The organometallic complex described in this embodiment has iridium as a central metal and a ligand. The ligand has a pyrazine skeleton, and iridium is bonded to the nitrogen at position 1 of the pyrazine skeleton, forming a pyrazine. The phenyl group is attached to the 2-, 3-, and 5-positions of the methyl group, and the 2- and 3-positions of the methyl group are attached to the methyl group. The phenyl groups each have an alkyl group as a substituent, and the phenyl bonded to the 5-position The group is an organometallic complex characterized by having a cyano group as a substituent.

[0053] Furthermore, the organometallic complex described in this embodiment has a first bond to iridium, which is a central metal. The first ligand has a pyrazine skeleton and a second ligand. The pyrazine skeleton has nitrogen atoms at the 2, 3, and 5 positions. A phenyl group is bonded to each of the 2- and 3-positions, and the phenyl groups bonded to the 2- and 3-positions are each a substituent. the phenyl group bonded to the 5-position has a cyano group as a substituent; The second ligand is an organometallic complex characterized in that it is a monoanionic ligand. In particular, as the second ligand, a monoanionic bidentate chelate having a β-diketone structure is used. Ligand, monoanionic bidentate chelating ligand with carboxyl group, phenolic water Monoanionic bidentate chelating ligands with acid groups, or both of the coordinating elements are nitrogen monoanionic bidentate chelating ligands, or cyclometallation of iridium and gold Organometallic complexes characterized by aromatic heterocyclic bidentate ligands capable of forming metal-carbon bonds. is.

[0054] The organometallic complex according to one embodiment of the present invention has a structure in which the 2- and 3-positions of the pyrazine skeleton contained in the ligand are bonded to each other. Phenyl groups with alkyl groups as substituents are bonded to the 1st and 2nd positions, forming a pyrazine skeleton. A phenyl group with a cyano group as a substituent is bonded to the 5th position of the pyrazine. The phenyl group attached to the 2-position of the skeleton is orthometalated to the iridium.

[0055] The organometallic complex according to one embodiment of the present invention is a complex of phenyl groups bonded to the 2- and 3-positions of the pyrazine skeleton. Since each alkyl group has an alkyl group as a substituent, the reaction between the organometallic complexes is prevented during sublimation. This prevents carbonization due to the reaction and also reduces the sublimation temperature. The authors have found that while this alkyl group has this effect, it also produces low molecular weight molecules upon sublimation. It was found that a small amount of dissolved matter was generated, which reduced the life of the light-emitting device. By having a cyano group as a substituent on the phenyl group bonded to the 5-position of the pyrazine skeleton, Although the sublimation temperature is higher than when there is no cyano group, the high temperature treatment during sublimation is effective. However, the generation of low molecular weight decomposition products derived from the alkyl groups, i.e., the resulting desorbed gas It has been found that the occurrence of

[0056] Therefore, the organometallic complex according to one embodiment of the present invention has a structure in which the 2- and 3-positions of the pyrazine skeleton are bonded to the organometallic complex. Each of the phenyl groups has an alkyl group as a substituent, and is further bonded to the 5-position of the pyrazine skeleton. The compound of the present invention is characterized in that the phenyl group bound to the compound has a cyano group as a substituent. The organometallic complex, which is one embodiment, has a structure that can adversely affect the device characteristics as an impurity after purification by sublimation. When using this to fabricate devices by vacuum deposition, it is difficult to mix decomposition products into the device. Since the penetration can be suppressed, an element having good life characteristics can be obtained.

[0057] The phenyl groups attached to the 2nd and 3rd positions of the pyrazine skeleton are each substituted with an alkyl group. When the phenyl group bonded to the 5-position of the pyrazine skeleton does not have a cyano group, Even if the organic metal complex is used, carbonization occurs due to the reaction between the organic metal complexes during sublimation. The organometallic complex in one embodiment has both the alkyl group and the cyano group. However, it suppresses carbonization due to reactions between organometallic complexes and the generation of low-molecular-weight desorbed gases. This is a necessary structure for this purpose, and this is a new finding.

[0058] Furthermore, the cyano group contained in the organometallic complex of one embodiment of the present invention can be used to generate the organometallic complex. The organometallic complex according to one embodiment of the present invention has the effect of shifting the wavelength of the light spectrum to a longer wavelength. The body has high color purity and emits deep red light. When deep red light is emitted, it is usually near-infrared light. Although the visibility is poor because the spectrum also has a spectrum in the outer region, the organometallic The alkyl group of the complex (the phenyl group bonded to the 2nd and 3rd positions of the pyrazine skeleton) The alkyl group (which causes the emission of fluorine) also has the effect of narrowing the emission spectrum, which prevents a decrease in visibility. Therefore, the organometallic complex according to one embodiment of the present invention has high color purity. High efficiency can be obtained even in the deep red where the wavelength is high.

[0059] In the above structure, the phenyl group bonded to the 5-position of the pyrazine skeleton may be a cyano group only. The presence of an alkyl group in addition to the organometallic complexes is effective in suppressing carbonization due to reactions between the organometallic complexes. It is particularly preferred that the alkyl group be attached to the 2-position of the phenyl group bonded to the 5-position of the pyrazine skeleton. This prevents the emission spectrum peak from moving too far into the long wavelengths, maintaining visibility. That is, it is particularly suitable for obtaining a deep red color with high color purity and high efficiency.

[0060] The organometallic complex described in this embodiment is an organometallic compound having a structure represented by the following general formula (G1): It is a complex.

[0061] [ka]

[0062] In general formula (G1), A 1 ~A 4 are each independently substituted or unsubstituted represents an alkyl group having 1 to 6 carbon atoms, and R 1 ~R 6 are each independently hydrogen, a substituent, or Unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms , a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. 7 ~R 11 are each independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. , a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted aryl group having 3 to 13 carbon atoms, 12 heteroaryl groups or cyano groups, at least one of which represents a cyano group .

[0063] The organometallic complex described in this embodiment is an organometallic compound having a structure represented by the following general formula (G2): It is a complex.

[0064] [ka]

[0065] In general formula (G2), A 1 ~A 4 are each independently the number of substituted or unsubstituted carbon atoms represents an alkyl group having 1 to 6 carbon atoms; R 6 is hydrogen, substituted or unsubstituted alkyl having 1 to 6 carbon atoms aryl groups, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms R represents any one of the heteroaryl groups of 3 to 12. 7 ~R 11 are each independently , hydrogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms, sialic acid groups, At least one of the groups represents a cyano group.

[0066] The organometallic complex described in this embodiment is an organometallic complex represented by the following general formula (G3): .

[0067] [ka]

[0068] In general formula (G3), A 1 ~A 4 are each independently the number of substituted or unsubstituted carbon atoms represents an alkyl group having 1 to 6 carbon atoms; R 1 ~R 6 are each independently hydrogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, or an unsubstituted heteroaryl group having 3 to 12 carbon atoms. 7 ~R 11 are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted aryl groups having 3 to 12 carbon atoms L represents either a heteroaryl group or a cyano group, and at least one of L represents a cyano group. , represents a monoanionic ligand.

[0069] The organometallic complex described in this embodiment is an organometallic complex represented by the following general formula (G4): .

[0070] [ka]

[0071] In general formula (G4), A 1 ~A 4 are each independently the number of substituted or unsubstituted carbon atoms represents an alkyl group having 1 to 6 carbon atoms; R 6 is hydrogen, substituted or unsubstituted alkyl having 1 to 6 carbon atoms aryl groups, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms R represents any one of the heteroaryl groups of 3 to 12. 7 ~R 11 are each independently , hydrogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms, sialic acid groups, At least one of L represents a cyano group. Represents a child.

[0072] In addition, the monoanionic ligand in each of the above structures is a compound having a β-diketone structure. Monoanionic bidentate chelating ligands, monoanionic bidentate chelating ligands with carboxyl groups a monoanionic bidentate chelating ligand having a phenolic hydroxyl group, or Monoanionic bidentate chelating ligands in which both coordination elements are nitrogen, or cyclo Aromatic heterocyclic bidentate ligands that can form metal-carbon bonds with iridium upon metalation Examples include:

[0073] The monoanionic ligand may be any of the following general formulae (L1) to (L6): Examples include:

[0074] [ka]

[0075] In the general formulae (L1) to (L6), R 71 ~R 94 are each independently hydrogen or Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, halogen groups, vinyl groups, substituted or Unsubstituted haloalkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 6 carbon atoms A represents a thio group, or a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms. 1 ~A 3 are independently sp bonds to nitrogen or hydrogen 2 Hybridized carbon or substituted sp 2 represents a hybrid carbon, and the substituent is an alkyl group having 1 to 6 carbon atoms, a halogen group, a represents a haloalkyl group having a molecular weight of 1 to 6, or a phenyl group; B 1 ~B 8 are each independently nitrogen or or a substituted or unsubstituted carbon, and the substituent is an alkyl group having 1 to 6 carbon atoms, a halogen atom, It represents a phenyl group, a haloalkyl group having 1 to 6 carbon atoms, or a phenyl group.

[0076] The organometallic complex shown in this embodiment is an organometallic complex represented by the following general formula (G5): is.

[0077] [ka]

[0078] In general formula (G5), A 1 ~A 4 are each independently substituted or unsubstituted represents an alkyl group having 1 to 6 carbon atoms, and R 1 ~R 6 are each independently hydrogen, a substituent, or Unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms , a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. 7 ~R 11 are each independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. , a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted aryl group having 3 to 13 carbon atoms, 12 heteroaryl groups or cyano groups, at least one of which represents a cyano group .

[0079] The organometallic complex shown in this embodiment is an organometallic complex represented by the following general formula (G6): is.

[0080] [ka]

[0081] In general formula (G6), A 1 ~A 4 are each independently substituted or unsubstituted represents an alkyl group having 1 to 6 carbon atoms, and R 6 is hydrogen, substituted or unsubstituted carbon atoms having 1 to 6 alkyl groups, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted represents any heteroaryl group having 3 to 12 carbon atoms. 7 ~R 11 are respectively Independently, hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted Aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms or a cyano group, and at least one of them represents a cyano group.

[0082] The organometallic complex shown in this embodiment is an organometallic complex represented by the following general formula (G7): is.

[0083] [ka]

[0084] In general formula (G7), A 1 ~A 4 are each independently substituted or unsubstituted represents an alkyl group having 1 to 6 carbon atoms, and R 1 ~R 6 are each independently hydrogen, a substituent, or Unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms , a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. 7 ~R 11 are each independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. , a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted aryl group having 3 to 13 carbon atoms, 12 heteroaryl groups or cyano groups, at least one of which represents a cyano group .

[0085] The organometallic complex shown in this embodiment is an organometallic complex represented by the following general formula (G8): is.

[0086] [ka]

[0087] In general formula (G8), A 1 ~A 4 are each independently substituted or unsubstituted represents an alkyl group having 1 to 6 carbon atoms, and R 6 is hydrogen, substituted or unsubstituted carbon atoms having 1 to 6 alkyl groups, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted represents any heteroaryl group having 3 to 12 carbon atoms. 7 ~R 11 are respectively Independently, hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted Aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms or a cyano group, and at least one of them represents a cyano group.

[0088] In any of the above general formulae (G1) to (G8), the number of substituted or unsubstituted carbon atoms an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted When the unsubstituted heteroaryl group having 3 to 12 carbon atoms has a substituent, the substituent is preferably a methyl group. ethyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group Alkyl groups with 1 to 6 carbon atoms, such as butyl, tert-butyl, pentyl, and hexyl groups group, cyclopentyl group, cyclohexyl group, cycloheptyl group, 1-norbornyl group, Cycloalkyl groups with 5 to 7 carbon atoms, such as 2-norbornyl groups, phenyl groups, biphenyl groups, etc. Examples of suitable aryl groups include aryl groups having 6 to 12 carbon atoms such as an aryl group.

[0089] In addition, A in the above general formulas (G1) to (G8) 1 ~A 4 , R 1 ~R 11 In either Specific examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, and an isopropyl group. propyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, neopentyl group, xyl, isohexyl, sec-hexyl, tert-hexyl, neohexyl group, 3-methylpentyl group, 2-methylpentyl group, 2-ethylbutyl group, 1,2-dimethyl Examples of the alkyl group include a 2,3-dimethylbutyl group, a 2,3-dimethylbutyl group, and a trifluoromethyl group.

[0090] In addition, A in the above general formulas (G1) to (G8) 1 ~A 4 , R 1 ~R 11 In either Specific examples of the aryl group having 6 to 13 carbon atoms include a phenyl group, a tolyl group (o-tolyl group, m-Tolyl group, p-Tolyl group), naphthyl group (1-naphthyl group, 2-naphthyl group), biphenyl Phenyl group (biphenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group) ), xylyl group, pentalenyl group, indenyl group, fluorenyl group, phenanthryl group, etc. The above-mentioned substituents may be bonded to each other to form a ring. For example, the carbon atom at the 9th position of the fluorenyl group has two phenyl groups as substituents. When the phenyl groups are bonded to each other to form a spirofluorene skeleton, etc.

[0091] In addition, A in the above general formulas (G1) to (G8) 1 ~A4 , R 1 ~R 11 In either Specific examples of the heteroaryl group having 3 to 12 carbon atoms include an imidazolyl group, a pyrazolyl group, Examples include a pyridyl group, a pyridazyl group, a triazyl group, a benzimidazolyl group, and a quinolyl group. can be done.

[0092] The organometallic complexes of one embodiment of the present invention represented by the general formulas (G1) to (G8) are 1 ~A 4 to The alkyl group prevents carbonization caused by reactions between organometallic complexes during sublimation. This can further reduce the sublimation temperature. However, during sublimation, a small amount of low molecular weight decomposition products is generated, which In addition, R is used as a substituent of the phenyl group attached to the 5-position of the pyrazine skeleton. 7 ~R 11 By having a cyano group in at least one of the above, Although the sublimation temperature is higher than in the case of the above alkyl group, the above alkyl group is not affected by the high temperature treatment during sublimation. This prevents the generation of low molecular weight decomposition products derived from the hydroxyl group, and thus the generation of desorbed gas. can.

[0093] Therefore, the organometallic complex of one embodiment of the present invention is a compound represented by the general formula (G1) to (G8) 1 ~A 4 each having an alkyl group as a substituent, and R 7 ~R 11 At least one of The compound is characterized in that it has a cyano group as a substituent. When using organometallic complexes to fabricate devices by vacuum deposition, they prevent decomposition products from getting into the device. Therefore, an element having good life characteristics can be obtained.

[0094] In addition, A 1 ~A 4 When R does not have an alkyl group as a substituent, 7 ~R 11 At least Even if either the organometallic complex or the cyano group is present, carbonization occurs due to the reaction between the organometallic complexes during sublimation. Therefore, the organometallic complex according to one embodiment of the present invention has A 1 or A 2 On the other hand , and A 3 or A 4 has an alkyl group at one end, and R 7 ~R 11 At least one of The presence of a cyano group in one of the organometallic complexes prevents carbonization due to reactions between the organometallic complexes and the formation of low-molecular-weight This is a necessary configuration for suppressing the generation of desorbed gas.

[0095] Furthermore, R 7 ~R 11 The cyano group possessed by at least one of the above is effective in enhancing the luminescence of the organometallic complex. That is, the organometallic complex according to one embodiment of the present invention has the effect of shifting the spectrum to longer wavelengths. The color purity is high and the deep red light is emitted. Although the visibility is reduced due to the spectrum in the A 1 ~A 4 Alkyl introduced into The group also has the effect of narrowing the emission spectrum, thereby minimizing the decrease in visibility. Therefore, the organometallic complex of one embodiment of the present invention can emit deep red light with high color purity. High efficiency can be achieved.

[0096] In the above general formulae (G1) to (G8), the phenyl bonded to the 5-position of the pyrazine skeleton The group has not only a cyano group but also an alkyl group, which facilitates the interaction of the organometallic complexes during sublimation. Therefore, it is more preferable to suppress carbonization due to the reaction. In G8), R 7 ~R 11 At least one of the above is an alkyl group having 1 to 6 carbon atoms. In particular, R 7 or R 11 At least one of the above is an alkyl group having 1 to 6 carbon atoms. The phenyl group prevents the emission spectrum peak from shifting too far to long wavelengths, improving visual sensitivity. That is, in the organometallic complex of one embodiment of the present invention, color purity can be maintained. This allows for the production of highly efficient deep red light.

[0097] Next, specific structural formulas of the organometallic complexes according to embodiments of the present invention are shown below. However, the present invention is not limited to these.

[0098] [ka]

[0099] [ka]

[0100] [ka]

[0101] [ka]

[0102] The organometallic complexes represented by the structural formulas (100) to (130) emit phosphorescence. These substances are novel substances that can be synthesized in the form of geometric isomers and steric isomers depending on the type of ligand. Isomers may exist, and the organometallic complex that is one embodiment of the present invention includes all of these isomers. It can be enjoyed.

[0103] Next, one embodiment of the present invention is a compound having a structure represented by general formula (G3) or general formula (G5). An example of a method for synthesizing the organometallic complex will be described below.

[0104] <Method for synthesizing pyrazine derivative represented by general formula (G0)> The pyridine derivative represented by the following general formula (G0) is used in the synthesis of general formula (G3) and general formula (G5). The radine derivatives are shown in three synthetic schemes (A1), (A2), and (A3) below. It can be synthesized by the synthesis method.

[0105] [ka]

[0106] In general formula (G0), A 1 ~A 4 are each independently the number of substituted or unsubstituted carbon atoms represents an alkyl group having 1 to 6 carbon atoms; R 1 ~R 6 are each independently hydrogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, or an unsubstituted heteroaryl group having 3 to 12 carbon atoms. 7 ~R 11 are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted aryl groups having 3 to 12 carbon atoms It represents either a heteroaryl group or a cyano group, and at least one represents a cyano group.

[0107] For example, the pyrazine derivative represented by the general formula (G0) can be synthesized by the following synthesis scheme (A1): As shown above, the halogenated benzene derivative (a1-1) is lithiated with an alkyl lithium or the like to form a di It can be obtained by reacting with phenylpyrazine (a2-1).

[0108] [ka]

[0109] In the above synthesis scheme (A1), Z represents a halogen, and A 1 ~A 4 Yes, respectively each independently represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; R 1 ~R 6 Is that each independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, substituted aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms, R 7 ~R 11 are each independently hydrogen, substituted or unsubstituted. a substituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, represents a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms or a cyano group, At least one represents a cyano group.

[0110] The pyrazine derivative represented by the general formula (G0) can be synthesized as shown in the following synthesis scheme (A2). As shown in Fig. 1, the benzene derivative boronic acid (a1-2) and the diphenylpyrazine halide ( a2-2) can be obtained by coupling with

[0111] [ka]

[0112] In the synthetic scheme (A2), X represents a halogen; 1 ~A 4 are each independently, represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and R 1 ~R 6 are each independently , hydrogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms an aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms; Also, R 7 ~R 11 are each independently hydrogen, a substituted or unsubstituted carbon atom, alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted represents an unsubstituted heteroaryl group having 3 to 12 carbon atoms or a cyano group, and represents a cyano group.

[0113] The pyrazine derivative represented by the general formula (G0) can be synthesized as shown in the following synthesis scheme (A3). As shown above, the reaction of benzene derivative-substituted diketone (a1-3) with diamine (a2-3) It can be obtained by making

[0114] [ka]

[0115] In the synthetic scheme (A3), A 1 ~A 4 are each independently substituted or unsubstituted represents an alkyl group having 1 to 6 carbon atoms, and R 1 ~R 6 are each independently hydrogen, a substituent, or Unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms , a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. 7 ~R 11 are each independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. , a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted aryl group having 3 to 13 carbon atoms, 12 heteroaryl groups or cyano groups, at least one of which represents a cyano group .

[0116] In addition to the three methods described above, there are several other known synthetic methods for the derivative (G0). Therefore, either method can be used.

[0117] In addition, the above-mentioned compounds (a1-1), (a1-2), (a1-3), (a2-1), and (a2 -2) and (a2-3) are commercially available in various types or can be synthesized. Many types of pyrazine derivatives represented by general formula (GO) can be synthesized. Therefore, the organometallic complexes according to one embodiment of the present invention have a wide variety of ligands. There is a characteristic that there is.

[0118] <Method for synthesizing organometallic complex represented by general formula (G3)> Next, a method for synthesizing the organometallic complex represented by the general formula (G3) will be described. As shown in the formula (B-1), a pyrazine derivative represented by the general formula (GO) and a halogen-containing compound are Iridium compounds (iridium chloride, iridium bromide, iridium iodide, etc.) No solvent or alcohol-based solvents (glycerol, ethylene glycol, 2-methoxyethylene glycol) Alcohol, ethanol, 2-ethoxyethanol, etc.) alone or with one or more alcoholic solvents By using a mixed solvent with water and heating in an inert gas atmosphere, the compound is crosslinked with halogen. The binuclear complex (B) is a type of organometallic complex with a unique structure, and is a novel substance. There are no particular limitations on the heating means, and an oil bath, a sand bath, or an aluminum block may be used. It is also possible to use microwaves as a heating means. .

[0119] [ka]

[0120] In the synthetic scheme (B-1), X represents a halogen; 1 ~A 4 are each independently , a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, R 1 ~R 6 are independent of each other hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted carbon an aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms; Also, R 7 ~R 11 are each independently hydrogen, substituted or unsubstituted carbon alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, or an unsubstituted heteroaryl group having 3 to 12 carbon atoms, or a cyano group, The other represents a cyano group.

[0121] Furthermore, as shown in the following synthesis scheme (B-2), The dinuclear complex (B) to be prepared and the monoanionic ligand raw material HL are mixed in an inert gas atmosphere. By reacting with HL, the proton of HL is removed, and L, which is formed, coordinates to the central metal iridium. As a result, an organometallic complex which is one embodiment of the present invention and is represented by General Formula (G3) can be obtained. There are no particular limitations on the heating means, and an oil bath, sand bath, aluminum block, or the like may be used. It is also possible to use microwaves as a heating means.

[0122] [ka]

[0123] In the synthetic scheme (B-2), L represents a monoanionic ligand, and Q represents a halogen. Represents A 1 ~A 4 are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. represents R 1 ~R 6 are each independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. alkyl groups, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted carbon represents any heteroaryl group having a prime number of 3 to 12. 7 ~R 11 are each unique In particular, hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted carbon atom, an aryl group having 6 to 13 prime numbers, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, At least one of them represents a cyano group.

[0124] <Method for synthesizing organometallic complex represented by general formula (G5)> Next, a method for synthesizing the organometallic complex represented by general formula (G5) is shown in synthetic scheme (C). As shown, halogen-containing iridium compounds (iridium chloride hydrate, iridium bromide) , iridium iodide, iridium acetate, ammonium hexachloroiridate, etc.), or or organic iridium complex compounds (acetylacetonato complex, diethyl sulfide complex, di -μ-chlorobridged dinuclear complexes, di-μ-hydroxobridged dinuclear complexes, etc.) and After mixing with the pyrazine derivative represented by the formula (I), the mixture is stirred in a solvent-free or alcohol-based solvent (glycerosol). ethanol, ethylene glycol, 2-methoxyethanol, 2-ethoxyethanol, etc. After that, by heating, an organometallic complex represented by general formula (G5) is obtained. do.

[0125] [ka]

[0126] In the synthetic scheme (C), A 1 ~A 4 are each independently a substituted or unsubstituted carbon atom. represents an alkyl group having 1 to 6 prime numbers, and R 1 ~R 6 are each independently hydrogen, substituted or unsubstituted. a substituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, R represents a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. 7 ~R 11 are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, Substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, substituted or unsubstituted aryl groups having 3 to 1 carbon atoms 2 represents either a heteroaryl group or a cyano group, and at least one represents a cyano group.

[0127] An example of a method for synthesizing an organometallic complex according to one embodiment of the present invention has been described above. is not limited to this, and may be synthesized by any other synthesis method.

[0128] The above-mentioned organometallic complexes are capable of emitting phosphorescence, and therefore are useful as light-emitting materials and light-emitting devices. It can be used as a light-emitting material in devices.

[0129] Furthermore, by using the organometallic complex which is one embodiment of the present invention, a light-emitting element and an emitter element with high emission efficiency can be obtained. It is possible to realize an optical device, an electronic device, or a lighting device. An element, a light-emitting device, an electronic device, or a lighting device can be realized.

[0130] Note that one embodiment of the present invention has been described in this embodiment. However, the present invention is not limited to these embodiments. In other words, various inventive aspects are described in this and other embodiments. Therefore, one embodiment of the present invention is not limited to a specific embodiment. Although an example in which the present invention is applied to a light-emitting element is shown, one embodiment of the present invention is not limited thereto. Depending on the situation, one embodiment of the present invention may be applied to devices other than light-emitting elements.

[0131] The structure shown in this embodiment mode may be used in appropriate combination with structures shown in other embodiments. can be done.

[0132] (Embodiment 2) In this embodiment, a light-emitting element which is one embodiment of the present invention will be described with reference to FIGS.

[0133] The light-emitting element shown in this embodiment has a pair of electrodes (a first electrode (anode) 101 and a second electrode ( An EL layer 102 including a light-emitting layer 113 is sandwiched between the cathode 103 and the cathode 104. The EL layer 102 is In addition to the light-emitting layer 113, a hole injection layer 111, a hole transport layer 112, an electron transport layer The layer 114 includes an electron transport layer 115 and an electron injection layer 115 .

[0134] When a voltage is applied to such a light-emitting element, holes injected from the first electrode 101 side and electrons injected from the second electrode 103 side recombine in the light-emitting layer 113, The energy generated by the photo-irradiation causes the light-emitting material, such as an organometallic complex, contained in the light-emitting layer 113 to emit light. will light up.

[0135] The hole injection layer 111 in the EL layer 102 is a hole transport layer 112 or a light emitting layer 113. For example, a layer that can inject holes into a material with high hole transport properties and an access In this case, the hole is absorbed by the acceptor material. Holes are generated when electrons are extracted from a material with high transport properties. Holes are injected from the layer 111 to the light-emitting layer 113 via the hole transport layer 112. The injection layer 111 may be made of a material with high hole injection properties. For example, molybdenum oxide vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide, etc. In addition, phthalocyanine (abbreviated as H2Pc) and copper phthalocyanine (C uPc) and other phthalocyanine compounds, 4,4'-bis[N-(4-diphenylamino phenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), N,N'-bis{4 -[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1 aromatic amine compounds such as 4,4'-diamine (DNTPD), or poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (P The hole injection layer 111 can also be formed from a polymer such as EDOT / PSS.

[0136] A preferred specific example for manufacturing the light-emitting element described in this embodiment mode will be described below.

[0137] The first electrode (anode) 101 and the second electrode (cathode) 103 are made of a metal, an alloy, an electrically conductive material, or the like. In particular, indium oxide, Indium tin oxide, silicon or silicon oxide containing Indium oxide-tin oxide, Indium oxide-zinc oxide (Indium Zinc Oxide) ide), indium oxide containing tungsten oxide and zinc oxide, gold (Au), platinum (Pt), Nickel (Ni), Tungsten (W), Chromium (Cr), Molybdenum (Mo ), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti) In addition to these, elements belonging to Groups 1 and 2 of the periodic table, such as lithium (Li) and cesium (Ce), Alkali metals such as cesium (Cs), calcium (Ca), strontium (Sr), etc. alkaline earth metals, magnesium (Mg), and alloys containing these (MgAg, Al rare earth metals such as Li, europium (Eu), ytterbium (Yb) and The first electrode (anode) 101 may be an alloy containing graphene or the like. The second electrode (cathode) 103 is formed by, for example, sputtering or vapor deposition (including vacuum deposition). It can be formed by, for example,

[0138] The hole-injecting layer 111 and the hole-transporting layer 112 may be formed of a material having a high hole-transporting property. Aromatic amine compounds, carbazole derivatives, aromatic hydrocarbons, polymer compounds (oligomers, Various organic compounds such as dendrimers and polymers can be used. The organic compound used as the material is preferably an organic compound with a high hole transporting property. Specifically, 1 x 10 -6 cm 2 It is preferable that the material has a hole mobility of 1 / Vs or more. In addition, the layer formed using a substance having a high hole transporting property may be a single layer or a stack of two or more layers. Specific examples of organic compounds that can be used as a hole transporting substance are listed below. List them specifically.

[0139] For example, the aromatic amine compound is N,N'-di(p-tolyl)-N,N'-diphenyl Nyl-p-phenylenediamine (DTDPPA), 4,4'-bis[N-(4-diphenyl phenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), DN TPD, 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenyla] 4,4'-bis[N-(1-naphthyl)-N-phenyl]benzene (abbreviation: DPA3B), N,N'-bis(3-phenylamino)biphenyl (abbreviation: NPB or α-NPD) (1,1'-diphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamino TPD, 4,4',4''-tris(carbazol-9-yl)triphenyl Tris(N,N-diphenylamino) Triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methyl (triphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4, 4'-Bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino] ]biphenyl (abbreviation: BSPB), and the like.

[0140] Specific examples of carbazole derivatives include 3-[N-(9-phenylcarbazole) [N-phenyl-3-yl]-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPC A1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenyla 3-[N-(1-naphthyl)amino]-9-phenylcarbazole (abbreviation: PCzPCA2), -N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazol Other examples include 4,4'-di(N- Carbazolyl)biphenyl (abbreviation: CBP), 1,3,5-tris[4-(N-carbazolyl)biphenyl] 9-[4-(10-phenyl-9-anthoxyphenyl)phenyl]benzene (abbreviation: TCPB), tolyl)phenyl]-9H-carbazole (abbreviation: CzPA), 1,4-bis[4-(N -carbazolyl)phenyl]-2,3,5,6-tetraphenylbenzene, etc. can be done.

[0141] Furthermore, examples of aromatic hydrocarbons include 2-tert-butyl-9,10-di(2-naphthalene). butyl)anthracene (abbreviation: t-BuDNA), 2-tert-butyl-9,10-di (1-naphthyl)anthracene, 9,10-bis(3,5-diphenylphenyl)anthracene Helical (abbreviation: DPPA), 2-tert-butyl-9,10-bis(4-phenylphenyl) 9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDBA), 9,10-di(2-naphthyl)anthracene 9,10-diphenylanthracene (abbreviated as DNA), 9,10-diphenylanthracene (abbreviated as DPAnth), 2 -tert-butylanthracene (abbreviation: t-BuAnth), 9,10-bis(4-methylanthracene) 2-tert-butyl-9,1 0-bis[2-(1-naphthyl)phenyl]anthracene, 9,10-bis[2-(1- naphthyl)phenyl]anthracene, 2,3,6,7-tetramethyl-9,10-di(1 -naphthyl)anthracene, 2,3,6,7-tetramethyl-9,10-di(2-naphthyl)anthracene 10,10'-diphenyl-9,9'-bianthryl, 9,9'-bianthryl, 10,10'-diphenyl-9,9'-bianthryl anthryl, 10,10'-bis(2-phenylphenyl)-9,9'-bianthryl, 10,10'-bis[(2,3,4,5,6-pentaphenyl)phenyl]-9,9'- Bianthryl, anthracene, tetracene, rubrene, perylene, 2,5,8,11-tetracene tetra(tert-butyl)perylene, etc. In addition, pentacene, coronet, etc. In this way, 1×10 -6 cm 2 / Vs or more hole mobility It is more preferable to use aromatic hydrocarbons having 14 to 42 carbon atoms. The aromatic hydrocarbon may have a vinyl skeleton. Examples of the diphenyl ether include 4,4'-bis(2,2-diphenylvinyl)biphenyl (abbreviation: D PVBi), 9,10-bis[4-(2,2-diphenylvinyl)phenyl]anthracene Examples include DPVPA (abbreviation: DPVPA).

[0142] Furthermore, poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenyl ether) Nylamine) (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 Polymer compounds such as [(phenyl)benzidine] (abbreviation: Poly-TPD) can also be used. can.

[0143] The acceptor materials used in the hole injection layer 111 and the hole transport layer 112 are , 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation :F4-TCNQ), chloranil, 2,3,6,7,10,11-hexacyano-1,4 , 5,8,9,12-hexaazatriphenylene (HAT-CN) and other electron-withdrawing groups (halo In particular, compounds with hydroxyl groups such as HAT-CN can be mentioned. Compounds in which electron-withdrawing groups are bonded to condensed aromatic rings containing multiple heteroatoms are thermally stable. Further, oxides of metals belonging to groups 4 to 8 in the periodic table are preferred. Specifically, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, Molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide have high electron-accepting properties. Among these, molybdenum oxide is particularly preferred because it is stable in the air, has low hygroscopicity, and is easy to handle. It is preferable because it is easy to do.

[0144] The light-emitting layer 113 is a layer containing a light-emitting substance. and phosphorescent light-emitting substances. It is preferable to use the organometallic complex shown in Form 1 as a light-emitting substance in the light-emitting layer 113 . In addition, the light-emitting layer 113 has a triplet excitation energy higher than that of the organometallic complex (guest material). It is preferable that the light-emitting layer 113 contains a large-capacity substance as a host material. In addition, upon recombination of carriers (electrons and holes) in the light-emitting layer 113, exciplexes (exciplexes) are formed. Two organic compounds that can be combined to form a cyclohexyl ether (also called a cyclohexyl ether) It may be configured to contain a material (which may be any of the above host materials). To form an exciplex, a compound that easily accepts electrons (a material with electron transport properties) is required. ) and a compound that easily accepts holes (a material with hole transport properties) can be combined. It is particularly preferable to combine a material having electron transport properties with a material having hole transport properties. When a host material that forms an exciplex is used in combination with a material having electron transport properties and a material having hole transport properties, By adjusting the mixing ratio of materials with transport properties, the carrier balance between holes and electrons in the light-emitting layer can be controlled. It is easy to optimize the carrier balance between holes and electrons in the light-emitting layer. By optimizing the area, it is possible to prevent the recombination of electrons and holes from becoming uneven in the light-emitting layer. By suppressing the bias in the region where recombination occurs, the reliability of the light-emitting element can be improved. can be done.

[0145] In addition, a compound that is easy to accept electrons and is preferably used to form the above exciplex ( As materials with electron transport properties, π-electron deficient heteroaromatic compounds such as nitrogen-containing heteroaromatic compounds are Aromatic compounds and metal complexes can be used. Specifically, bis(10-hydroxybenzoates) Bis(2-methyl-8-benzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), -quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq ), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzo[ oxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzo[ zothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), and other metal complexes, such as 2- (4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxazolidinyl Azole (abbreviation: PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-te rt-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 1,3-bis[ 5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzyl Benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazo 2,2',2''-(2-yl)phenyl]-9H-carbazole (abbreviation: CO11) -(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) ) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1- Polyazolidinedione such as phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II) Heterocyclic compounds with a phenyl skeleton and 2-[3-(dibenzothiophen-4-yl)phenyl] ]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'- (Dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxa Phosphorus (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazole-9- 2mCzBPD Bq), 2-[4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl] Dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(dibenzyl) (benzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mD BTPDBq-II) and 6-[3-(dibenzothiophen-4-yl)phenyl] Dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II), 4,6-bis[ 3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm ), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6 mDBTP2Pm-II), 4,6-bis[3-(9H-carbazol-9-yl)phenyl] Heterocyclization of diazine skeletons such as 4,6mCzP2Pm Compounds such as 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-3-yl]-9H-carbazol-3-yl 4,6-diphenyl-1,3,5-triazine (abbreviated as '4,6-diphenyl-1,3,5-triazine- ...') Heterocyclic compounds with triazine skeletons such as PCCzPTzn and 3,5-bis[ 3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy) , 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB) Among the above, heterocyclic compounds having a pyridine skeleton, such as Heterocyclic compounds with triazine skeletons and heterocyclic compounds with pyridine skeletons are reliable. In particular, diazine (pyrimidine or pyrazine) skeletons and triazine The heterocyclic compound having a skeleton has a high electron transport property and also contributes to a reduction in driving voltage.

[0146] In addition, a compound that is easy to accept holes and is preferable for use in forming the above exciplex ( As a material with hole transport properties, π-electron-rich heteroaromatic compounds (e.g., carbazole derivatives) In particular, an aromatic amine or an indole derivative can be suitably used. , 2-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]spiro- 9,9'-Bifluorene (abbreviation: PCASF), 4,4',4''-tris[N-(1- Naphthyl)-N-phenylamino]triphenylamine (abbreviation: 1'-TNATA), 2 ,7-Bis[N-(4-diphenylaminophenyl)-N-phenylamino]spiro-9 ,9'-bifluorene (abbreviation: DPA2SF), N,N'-bis(9-phenylcarbazo (3-yl)-N,N'-diphenylbenzene-1,3-diamine (abbreviation: PCA2 B), N-(9,9-dimethyl-2-diphenylamino-9H-fluoren-7-yl) Diphenylamine (abbreviation: DPNF), N,N',N''-triphenyl-N,N',N ''-Tris(9-phenylcarbazol-3-yl)benzene-1,3,5-triamine PCA3B, 2-[N-(4-diphenylaminophenyl)-N-phenyl amino]spiro-9,9'-bifluorene (abbreviation: DPASF), N,N'-bis[4- (Carbazol-9-yl)phenyl]-N,N'-diphenyl-9,9-dimethylfluor Oleno-2,7-diamine (abbreviation: YGA2F), NPB, N,N'-bis(3-methyl) phenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine( abbreviation: TPD), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenyl 4-phenyl-4'-(9-phenylamino)biphenyl (abbreviation: DPAB), BSPB, (9-phenylfluorenyl)triphenylamine (abbreviation: BPAFLP), 4-phenyl -3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAF LP), N-(9,9-dimethyl-9H-fluoren-2-yl)-N-{9,9-dimethyl 2-[N'-phenyl-N'-(9,9-dimethyl-9H-fluoren-2-yl]ethyl] )amino]-9H-fluoren-7-yl}phenylamine (abbreviation: DFLADFL), PCzPCA1, 3-[N-(4-diphenylaminophenyl)-N-phenylamino] -9-phenylcarbazole (abbreviation: PCzDPA1), 3,6-bis[N-(4-diphenyl) [N-phenylaminophenyl]-9-phenylcarbazole (abbreviation: P CzDPA2), DNTPD, 3,6-bis[N-(4-diphenylaminophenyl)- N-(1-naphthyl)amino]-9-phenylcarbazole (abbreviation: PCzTPN2), PCzPCA2, 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl ) triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9 -phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBBi1 BP), 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: PCB NBB), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl) Amino]-9-phenylcarbazole (abbreviation: PCzPCN1), 9,9-dimethyl-N -phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl] Fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl -9H-carbazol-3-yl)phenyl]spiro-9,9'-bifluorene-2-a PCBASF, N-(4-biphenyl)-N-(9,9-dimethyl-9H -fluoren-2-yl)-9-phenyl-9H-carbazol-3-amine (abbreviation: P CBiF), N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9 H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluorene-2- Compounds with aromatic amine skeletons such as PCBBiF and 1,3-bis(2-methyl-2-propanol) (N-carbazolyl)benzene (abbreviation: mCP), CBP, 3,6-bis(3,5-diphenyl) CzTP, 9-phenyl-9H -3-(9-phenyl-9H-carbazol-3-yl)carbazole (abbreviation: PCCP ), and compounds with a carbazole skeleton such as 4,4',4''-(benzene-1,3, 5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl Phenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzo Thiophene (abbreviation: DBTFLP-III), 4-[4-(9-phenyl-9H-fluoro [6-phenyl-9-yl]phenyldibenzothiophene (abbreviation: DBTFLP- IV) and 4,4',4''-(benzene-1,3 ,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II), 4-{3-[3 -(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II) and other compounds with a furan skeleton. Among the above, compounds having an aromatic amine skeleton and compounds having a carbazole skeleton are: It is preferable because it has good reliability, high hole transport properties, and contributes to reducing the driving voltage. .

[0147] In the light-emitting layer 113, the above-mentioned organometallic complex (guest material) and the host material are contained. By forming the light-emitting layer 113 in this manner, phosphorescence with high luminous efficiency can be obtained. Cut.

[0148] In addition, the light-emitting layer 113 is not limited to the single-layer structure shown in FIG. 1(A) in the light-emitting element. It may also have a laminated structure of two or more layers as shown in (B). For example, the first light-emitting layer 113 (a1 ) is configured to emit fluorescent light, and the second layer laminated on the first light-emitting layer 113(a1) The stacking order may be such that phosphorescence is obtained from the second light-emitting layer 113(a2). In the layer where phosphorescence is obtained, the exciplex It is preferable that the structure be such that light emission is obtained by energy transfer from the dopant to the light emitting element. Regarding the emission color, the emission color obtained from one layer and the emission color obtained from the other layer are They may be the same or different, but if they are different, for example, blue from one layer The other layer emits orange or yellow light. In addition, each layer may have a structure containing multiple types of dopants. good.

[0149] When the light-emitting layer 113 has a stacked structure, the organometallic complexes described in Embodiment 1 can be used. Other luminescent materials that convert singlet excitation energy into luminescence, or triplet excitation energy into luminescence The luminescent materials that change the For example, the following can be mentioned:

[0150] Examples of luminescent materials that convert singlet excitation energy into luminescence include fluorescent materials (fluorescent materials). photoactive compounds).

[0151] Fluorescent substances include N,N'-bis[4-(9H-carbazol-9-yl)fluorene] [phenyl]-N,N'-diphenylstilbene-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-anthryl)triphenylamine (abbreviation: 2YGAP PA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]phenyl ]-9H-carbazol-3-amine (abbreviation: PCAPA), perylene, 2,5,8,1 1-Tetra(tert-butyl)perylene (TBP), 4-(10-phenyl-9 -anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenyl Amine (abbreviation: PCBAPA), N,N''-(2-tert-butylanthracene-9 ,10-diyldi-4,1-phenylene)bis[N,N',N'-triphenyl-1,4 -phenylenediamine] (abbreviation: DPABPA), N,9-diphenyl-N-[4-(9 ,10-diphenyl-2-anthryl)phenyl]-9H-carbazol-3-amine( Abbreviation: 2PCAPPA), N-[4-(9,10-diphenyl-2-anthryl)phenyl] 2DPAP PA), N,N,N',N',N'',N'',N''',N'''-octaphenyldi Benzo[g,p]chrysene-2,7,10,15-tetraamine (abbreviation: DBC1), Marine 30, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9 H-Carbazol-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1 '-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazo N-(9,10-diphenyl-2-amine) tolyl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DP APA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl ]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABP hA), 9,10-bis(1,1'-biphenyl-2-yl)-N-[4-(9H-cal 2Y GABPhA), N,N,9-triphenylanthracen-9-amine (abbreviated as DPhA PhA), Coumarin 545T, N,N'-Diphenylquinacridone (abbreviation: DPQd), Rubrene, 5,12-bis(1,1'-biphenyl-4-yl)-6,11-diphenyl Tetracene (abbreviation: BPT), 2-(2-{2-[4-(dimethylamino)phenyl]ethoxy) Thenyl}-6-methyl-4H-pyran-4-ylidene)propanedinitrile (abbreviation: DC M1), 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H- Benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}pro Pandinitrile (abbreviation: DCM2), N,N,N',N'-tetrakis(4-methylphenyl) p-mPhTD, 7,14-diphenyl N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a] Fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), {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-tert-butyl-6-[2-(1 ,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[i j]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinite (abbreviation: DCJTB), 2-(2,6-bis{2-[4-(dimethylamino)phenyl {4H-pyran-4-ylidene}propanedinitrile (abbreviated as BisDC M), 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}propanedinitrile (abbreviation: BisDCJ™) Examples include:

[0152] Examples of luminescent materials that convert triplet excitation energy into luminescence include phosphorescent materials (phosphors Fluorescent compounds and TADF materials that exhibit TADF The delayed fluorescence in TADF materials is similar to that of ordinary fluorescence. It is a type of light emission that has a spectrum and has a remarkably long lifetime. Its lifetime is 1×10 -6 seconds or more Above, preferably 1 x 10 -3 More than a second.

[0153] Phosphorescent substances include bis{2-[3',5'-bis(trifluoromethyl)phenyl]phenyl} Nyl]pyridinato-N,C 2’}Iridium(III) picolinate (abbreviation: [Ir(C F3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyridin Nat-N,C 2’ ]Iridium(III) acetylacetonate (abbreviation: FIracac ), tris(2-phenylpyridinato)iridium(III) (abbreviation: [Ir(ppy) 3]), bis(2-phenylpyridinato)iridium(III) acetylacetonate ( Abbreviation: [Ir(ppy)2(acac)]), tris(acetylacetonato)(monophenyl Anthroline) terbium(III) (abbreviation: [Tb(acac)3(Phen)]), Bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: [ Ir(bzq)2(acac)]), 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’ ) Iriji Ir(bt)2(acac) [2-(2'-benzo[4,5-a]thienyl)pyridinato-N,C 3’ ]iridium( III) Acetylacetonate (abbreviation: [Ir(btp)2(acac)]), bis(1 -Phenylisoquinolinato-N,C 2’) Iridium(III) acetylacetonate ( Abbreviation: [Ir(piq)2(acac)]), (acetylacetonato)bis[2,3-bis(acetylacetonato) [Ir(F dpq)2(acac)]), (acetylacetonato)bis(3,5-dimethyl-2-furan [Ir(mppr-Me)2(aca c)]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenyl [Ir(mppr-iPr)2(acac) ]), (acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium (III) (abbreviation: [Ir(tppr)2(acac)]), bis(2,3,5-trifluoromethyl) (phenylpyrazinate)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(t ppr)2(dpm)]), (acetylacetonato)bis(6-tert-butyl-4- Phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2(ac ac)]), (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium Ir(III) (abbreviation: [Ir(dppm)2(acac)]), 2,3,7,8,12, 13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP), tris(1,3-diphenyl-1,3-propanedionato)(monofena (Eu(DBM)3(Phen)]), Tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthate) Examples include [Eu(TTA)3(Phen)], It can be obtained.

[0154] TADF materials include, for example, fullerenes and their derivatives, and activators such as proflavine. Lysine derivatives, eosin, etc. Also, magnesium (Mg), zinc (Zn), Cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or para Examples of the metal-containing porphyrin include porphyrins containing palladium (Pd). For example, protoporphyrin-tin fluoride complex (abbreviated as SnF2 (Proto IX), mesoporphyrin-tin fluoride complex (abbreviation: SnF2(Meso IX)), Hematoporphyrin-tin fluoride complex (abbreviated as SnF2(Hemato IX)), Coproporphyrin tetramethyl ester-tin fluoride complex (abbreviation: SnF2(Copro III-4Me), octaethylporphyrin-tin fluoride complex (abbreviation: SnF2(O EP), etioporphyrin-tin fluoride complex (abbreviation: SnF2(Etio I)), Examples include octaethylporphyrin-platinum chloride complex (abbreviation: PtCl2OEP). Furthermore, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[2, 3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ ) and other heterocyclic compounds having a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring. In addition, a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring can be directly bonded to each other. The resulting materials exhibit the donor properties of π-electron-rich heteroaromatic rings and the acceptor properties of π-electron-deficient heteroaromatic rings. This is particularly preferable because the bond strength between S1 and T1 is increased and the energy difference between S1 and T1 is reduced.

[0155] Furthermore, the light-emitting layer 113 contains quantum dots (QDs) that have unique optical properties. QDs (quadrature dots) can also be used. QDs refer to nanoscale semiconductor crystals. Specifically, the diameter is approximately several nm to several tens of nm. The optical and electronic properties can be changed by changing the material, making it easy to adjust the color of emitted light, etc. In addition, quantum dots have a narrow peak width in the emission spectrum, which allows for emission with good color purity. It is possible.

[0156] The materials that make up quantum dots are elements from Groups 14, 15, and 16 of the periodic table. Elements, compounds consisting of multiple Group 14 elements, elements belonging to Groups 4 to 14 and Group 16 Compounds with Group 2 elements and Group 16 elements, compounds with Group 13 elements and Group 15 elements Compounds of Group 13 and Group 17 elements, compounds of Group 14 and Group 15 elements Compounds of Group 11 elements and Group 17 elements, iron oxides, titanium oxides, chalcogenides Examples of suitable semiconductor clusters include doped spinels and various semiconductor clusters.

[0157] Specifically, cadmium selenide, cadmium sulfide, cadmium telluride, zinc selenide , zinc oxide, zinc sulfide, zinc telluride, mercury sulfide, mercury selenide, mercury telluride, arsenide Indium, indium phosphide, gallium arsenide, gallium phosphide, indium nitride, gallium nitride Sodium, indium antimonide, gallium antimonide, aluminum phosphide, aluminum arsenide Aluminum, aluminum antimonide, lead selenide, lead telluride, lead sulfide, lead selenide Indium, indium telluride, indium sulfide, gallium selenide, arsenic sulfide, selenium arsenic sulphide, arsenic telluride, antimony sulphide, antimony selenide, antimony telluride, sulphide Bismuth oxide, 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, calcium sulfide, calcium selenide, calcium telluride, beryllium sulfide, Beryllium telluride, beryllium sulfide, magnesium selenide, sulfur Germanium oxide, germanium selenide, germanium telluride, tin sulfide, tin selenide, Tin telluride, lead oxide, copper fluoride, copper chloride, copper bromide, copper iodide, copper oxide, copper selenide, oxide Nickel, cobalt oxide, cobalt sulfide, iron tetroxide, iron sulfide, manganese oxide, molybdenum sulfide Butane, vanadium oxide, tungsten oxide, tantalum oxide, titanium oxide, zirconium oxide ammonium, silicon nitride, germanium nitride, aluminum oxide, barium titanate, selenium and Compounds of zinc and cadmium, compounds of indium, arsenic and phosphorus, compounds of cadmium, selenium and sulfur Yellow compound, Cadmium, Selenium and Tellurium compound, Indium, Gallium and Arsenic compound compounds of indium, gallium and selenium; compounds of indium, selenium and sulfur; copper and Examples include compounds of indium and sulfur and combinations thereof. Furthermore, the composition may be expressed in any ratio, that is, a so-called alloy type quantum well. For example, quantum dots of alloy type of cadmium, selenium and sulfur are The emission wavelength can be changed by changing the content ratio of This is one of the effective methods.

[0158] The quantum dot structure can be of the core type, core-shell type, or core-multishell type. Any of these may be used. In the case of core-type and core-multishell quantum dots, the inorganic material used for the core is wider than that of the inorganic material. By forming a shell using another inorganic material with a band gap, The effects of defects and dangling bonds on the surface can be reduced, improving the quantum efficiency of light emission. This is preferable because it can greatly improve

[0159] Furthermore, QDs can be dispersed in a solution, so they can be applied to various methods such as coating, inkjet printing, and printing. The light-emitting layer 113 can be formed by the above method. QDs emit bright and vivid colors. In addition, it can emit light over a wide range of wavelengths, and has high efficiency and a long life. By using 13, the device characteristics can be improved.

[0160] The electron transport layer 114 is a layer containing a substance with a high electron transport property (also referred to as an electron transport compound). The electron transport layer 114 is made of tris(8-quinolinolato)aluminum (abbreviation: Alq3 ), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), Be Bq2, BAlq, bis[2-(2-hydroxyphenyl)benzoxazolato]zinc ( Abbreviation: Zn(BOX)2), bis[2-(2-hydroxyphenyl)benzothiazol-ato] Metal complexes such as zinc (abbreviated as Zn(BTZ)2) can be used. 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole -2-yl]benzene (abbreviation: OXD-7), TAZ, 3-(4-tert-butylphenyl) (4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triaconazole azole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathox 4,4'-bis(5-methylbenzoxazole-2-yl) Heteroaromatic compounds such as bis(trimethylsilyl)stilbene (abbreviation: BzOs) can also be used. , poly(2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexylfulv) PF-Py ), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-biphenyl) pyridine-6,6'-diyl)] (abbreviation: PF-BPy), as well as phosphine oxide skeletons It is also possible to use polymer compounds having the following structure. -6 cm 2 It is a material with electron mobility of 1 / Vs or more. Any substance other than those mentioned above may be used for the electron-transporting layer 114 as long as it is a suitable substance.

[0161] The electron transport layer 114 may be a single layer or may be a laminate of two or more layers made of the above-mentioned materials. The structure may be such that:

[0162] The electron injection layer 115 is a layer containing a substance with high electron injection properties. Lithium fluoride (LiF), Cesium fluoride (CsF), Calcium fluoride (CaF2), Alkali metals, alkaline earth metals, or their derivatives, such as lithium oxide (LiOx) Compounds such as erbium fluoride (ErF3) can also be used. Alternatively, an electride may be used for the electron injection layer 115. The electride may be, for example, a mixed oxide of calcium and aluminum with electrons. The material constituting the electron transport layer 114 may be a material containing a high concentration of can also be used.

[0163] The electron injection layer 115 is made of a composite material obtained by mixing an organic compound and an electron donor (donor). Such composite materials are formed by electron donors generating electrons in organic compounds. In this case, the organic compound is: It is preferable that the material has excellent transport properties for the generated electrons. Specifically, for example, the above-mentioned The substance constituting the electron transport layer 114 (metal complex, heteroaromatic compound, etc.) can be used. The electron donor may be any substance that exhibits electron donating properties to organic compounds. The metals are preferably alkali metals, alkaline earth metals, or rare earth metals, and more preferably lithium, cesium, magnesium, or the like. Examples of the metals include magnesium, calcium, erbium, and ytterbium. Metal oxides and alkaline earth metal oxides are preferred, and lithium oxide, calcium oxide, Examples of the base include barium oxide. In addition, a Lewis base such as magnesium oxide can be used. It is also possible to use organic compounds such as tetrathiafulvalene (TTF). It is also possible.

[0164] The hole injection layer 111, the hole transport layer 112, the light emitting layer 113, and the electron transport layer 114 The electron injection layer 115 can be formed by a deposition method (including a vacuum deposition method), a printing method (for example, a letterpress printing method), or the like, respectively. printing method, intaglio printing method, gravure printing method, lithographic printing method, stencil printing method, etc.), inkjet method The method may be a coating method or a combination of methods. In addition, a hole injection layer 111, a hole transport layer 112, a light emitting layer 113, an electron transport layer 114, and an electron In addition to the above-mentioned materials, the injection layer 115 may contain inorganic compounds such as quantum dots or polymer compounds. (oligomers, dendrimers, polymers, etc.) may also be used.

[0165] The light-emitting element described above is configured such that a potential difference is applied between the first electrode 101 and the second electrode 103. Current flows due to this, and holes and electrons recombine in the EL layer 102, causing light to be emitted. This light emission is emitted from either the first electrode 101 or the second electrode 103. Therefore, the first electrode 101 and the second electrode 103 are connected to each other. Either one or both of the electrodes is a light-transmitting electrode.

[0166] The light-emitting element described above can emit phosphorescence based on an organometallic complex. A light-emitting element with higher efficiency than a light-emitting element using only a photoactive compound can be realized.

[0167] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiments. It shall be possible to do so.

[0168] (Embodiment 3) In this embodiment, a light-emitting element having a structure including a plurality of EL layers (hereinafter, This section explains the tandem light-emitting device.

[0169] The light-emitting element shown in this embodiment has a pair of electrodes (first electrode 201) as shown in FIG. and second electrode 204) via a charge generating layer 205. The light emitting element is a tandem type light emitting element having a first EL layer 202(1) and a second EL layer 202(2).

[0170] In this embodiment, the first electrode 201 is an electrode that functions as an anode, and the second electrode The electrode 204 functions as a cathode. 04 can have the same structure as in Embodiment 2. In addition, a plurality of EL layers (first The EL layer 202(1) and the second EL layer 202(2) are the same as the EL layer shown in the second embodiment. Both may have the same configuration, or either one may have the same configuration. That is, the first EL layer 202(1) and the second EL layer 202(2) may have the same structure but different If the configuration is the same, the second embodiment can be applied.

[0171] In addition, a plurality of EL layers (first EL layer 202(1), second EL layer 202(2)) are provided between the EL layers. The charge generating layer 205 is formed by applying a voltage to the first electrode 201 and the second electrode 204. When the organic layer is turned on, electrons are injected into one EL layer and holes are injected into the other EL layer. In this embodiment, the first electrode 201 is set to have a higher potential than the second electrode 204. When a voltage is applied in this manner, electrons are injected from the charge generating layer 205 into the first EL layer 202(1). As a result, holes are injected into the second EL layer 202(2).

[0172] The charge generating layer 205 is transparent to visible light from the viewpoint of light extraction efficiency. (Specifically, it is preferable that the visible light transmittance of the charge generating layer 205 is 40% or more.) In addition, the charge generating layer 205 has a lower conductivity than the first electrode 201 and the second electrode 204. It also works.

[0173] The charge generation layer 205 is formed by adding an electron acceptor to an organic compound having high hole transport properties. Even if the structure is such that an electron donor (donor) is added to an organic compound with high electron transport properties, Alternatively, both of these structures may be stacked.

[0174] In the case where an electron acceptor is added to an organic compound having high hole transport properties, As the organic compound with high transportability, the hole injection layer 111 and the hole transport layer 1 The materials shown in 12 as having high hole transport properties can be used. For example, N Aromatic amine compounds such as PB, TPD, TDATA, MTDATA, and BSPB are used. The materials mentioned here are mainly 1×10 -6 cm 2 Hole mobility above / Vs However, if the organic compound has a higher hole transporting property than the electron transporting property, Other materials may also be used.

[0175] The electron acceptor is 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroethylene. Examples include fluoroquinodimethane (abbreviation: F4-TCNQ), chloranil, etc. Further examples include oxides of metals belonging to groups 4 to 8 of the periodic table. Specifically, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, Tungsten oxide, manganese oxide, and rhenium oxide are preferred because of their high electron-accepting properties. In particular, molybdenum oxide is preferred because it is stable in the air, has low hygroscopicity, and is easy to handle. stomach.

[0176] On the other hand, in the case where an electron donor is added to an organic compound having high electron transport properties, As the organic compound having a high electron transporting property, the electron transporting compound used for the electron transport layer 114 in the second embodiment is The materials shown as having high conductivity can be used. For example, Alq, Almq3, Metal complexes with quinoline or benzoquinoline skeletons, such as BeBq2 and BAlq In addition, other oxides such as Zn(BOX)2 and Zn(BTZ)2 can be used. Metal complexes having thiazole or thiazole ligands can also be used. In addition to metal complexes, PBD, OXD-7, TAZ, BPhen, BCP, etc. can also be used. The substances mentioned here are mainly 1×10 -6 cm 2 / Vs or higher electron mobility In addition, any organic compound that has a higher electron transporting property than hole transporting property can be used. You can also use quality.

[0177] The electron donor may be an alkali metal, an alkaline earth metal, a rare earth metal, or The metals belonging to Groups 2 and 13 of the periodic table and their oxides and carbonates are used. Specifically, lithium (Li), cesium (Cs), magnesium (Mg) , calcium (Ca), ytterbium (Yb), indium (In), lithium oxide, It is preferable to use cesium carbonate. The compound may be used as the electron donor.

[0178] The charge generating layer 205 is formed using the above-mentioned materials, and thus the EL layer is laminated. In addition, the formation of the charge generating layer 205 can suppress the increase in the driving voltage. The methods include deposition methods (including vacuum deposition methods), printing methods (e.g., letterpress printing, intaglio printing, etc.), , gravure printing, lithography, stencil printing, etc.), inkjet printing, coating, etc. They can be formed using either alone or in combination.

[0179] In this embodiment mode, a light-emitting element having two EL layers has been described. In this way, n (where n is 3 or more) EL layers (202(1) to 202(n)) are stacked. The same can be applied to the light emitting device according to the present embodiment. When there are multiple EL layers between a pair of electrodes, as in the case of a device, By arranging the charge generation layers (205(1) to 205(n-1)), the current density can be kept low. It is possible to emit light in a high brightness range while maintaining a low current density, which allows for long-life elements. It can be achieved.

[0180] In addition, by making the luminescent color of each EL layer different, the desired luminescent color can be obtained as a whole. For example, in a light-emitting element having two EL layers, the first By making the luminescent color of the first EL layer and the luminescent color of the second EL layer complementary to each other, It is also possible to obtain a light emitting element that emits white light as a whole. This refers to the relationship between colors that become achromatic. In other words, when light of complementary colors is mixed with each other, Specifically, blue light is emitted from the first EL layer, and white light is emitted from the second EL layer. In this case, a combination in which yellow or orange light is emitted from the EL layer of the second electrode is possible. Both the blue and yellow (or orange) emissions are the same fluorescent or phosphorescent emissions It is not necessary that the blue emission is fluorescent and the yellow (or orange) emission is phosphorescent. A combination of these may also be used, or vice versa.

[0181] The same applies to a light-emitting element having three EL layers. For example, the light-emitting element of the first EL layer The light color of the first EL layer is red, the light color of the second EL layer is green, and the light color of the third EL layer is blue. In some cases, the light emitting element as a whole can emit white light.

[0182] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiment modes. It is possible.

[0183] (Fourth embodiment) In this embodiment, a light-emitting device which is one embodiment of the present invention will be described.

[0184] The light emitting device may be a passive matrix light emitting device or an active matrix light emitting device. The light-emitting device described in this embodiment may be a light-emitting device. Optical elements can be applied.

[0185] In this embodiment mode, an active matrix light emitting device will be described with reference to FIG. do.

[0186] 3A is a top view showing the light emitting device, and FIG. 3B is a top view showing the light emitting device along the dashed line AA in FIG. 3A. The light emitting device according to this embodiment is provided on an element substrate 301. a pixel section 302, a driver circuit section (source line driver circuit) 303, and a driver circuit section (gate line The pixel section 302, the driver circuit section 303, and the driver circuit section 304a, 304b are connected to the pixel section 302. The driving circuit section (304a, 304b) is sealed to the element substrate 301 by a sealing material 305. The substrate 306 is sealed between the substrate 306 and the semiconductor device 302 .

[0187] Also, on the element substrate 301, a driving circuit section 303 and driving circuit sections (304a, 304b) ) to an external signal (e.g., video signal, clock signal, start signal, or reset A wiring 307 is provided for connecting an external input terminal for transmitting a signal or potential. Here, an FPC (flexible printed circuit) 308 is used as the external input terminal. This shows an example of how to install an FPC. A printed wiring board (PWB) may be attached. This includes not only the light-emitting device itself but also the state in which an FPC or PWB is attached to it. This shall be done.

[0188] Next, the cross-sectional structure will be described with reference to FIG. and a pixel portion are formed, but here, a driver circuit portion 303 which is a source line driver circuit and , a pixel portion 302 is shown.

[0189] The driving circuit section 303 is exemplified by a configuration in which an FET 309 and an FET 310 are combined. The driver circuit 303 is unipolar (either n-channel or p-channel). The circuit may be formed of a transistor (only one of the two) or an n-channel transistor. The semiconductor device may be formed of a CMOS circuit including a p-channel transistor and a p-channel transistor. In this form, a driver integrated type in which a drive circuit is formed on a substrate is shown, but this is not necessarily required. In addition, the driving circuit can be formed externally rather than on the substrate.

[0190] The pixel section 302 also includes a switching FET (not shown) and a current control FET 312. The wiring (source electrode or drain electrode) of the current control FET 312 is connected to the light emitting element 3 17a and the first electrode (anode) (313a, 313b) of the light-emitting element 317b. In this embodiment, the pixel section 302 is connected to two FETs (switch An example of a configuration using a switching FET and a current control FET 312 has been shown. For example, a configuration in which three or more FETs and a capacitance element are combined can be used. good.

[0191] The FETs 309, 310, and 312 are, for example, staggered or inverted staggered transistors. Semiconductor materials that can be used for the FETs 309, 310, and 312 Examples of materials include Group 13 semiconductors, Group 14 (silicon, etc.) semiconductors, compound semiconductors, An oxide semiconductor or an organic semiconductor can be used. The crystallinity of the semiconductor can be determined as follows: There are no particular limitations, and for example, an amorphous semiconductor or a crystalline semiconductor can be used. In particular, it is preferable to use an oxide semiconductor for the FETs 309, 310, and 312. Examples of oxide semiconductors include In-Ga oxide and In-M-Zn oxide (M is Al). , Ga, Y, Zr, La, Ce, Hf or Nd). 0,312, for example, an energy gap of 2 eV or more, preferably 2.5 eV or more Furthermore, by using an oxide semiconductor having a gate resistance of preferably 3 eV or more, the off-state voltage of the transistor can be reduced. The flow can be reduced.

[0192] In addition, the first electrodes (313a, 313b) are provided with conductive films (320a, 320b) for optical adjustment. For example, as shown in FIG. 3(B), a light-emitting element 317a and a light-emitting element 317b are stacked. When the wavelength of light extracted by the optical element 317b is different from that of the conductive film 320a, the conductive film 320b is The thickness of the insulating film 3 is different from that of the insulating film 3b. Here, a positive photosensitive acrylic resin is used as the insulator 314. In this embodiment, the first electrode (313a, 3 13b) is used as the anode.

[0193] It is also preferable to form a surface having a curvature at the upper or lower end of the insulator 314. By forming the shape of the insulating material 314 as described above, the thickness of the film formed on the insulating material 314 can be reduced. For example, the material of the insulator 314 may be a negative type. Either photosensitive resin or positive photosensitive resin can be used, and the organic compound Inorganic compounds such as silicon oxide, silicon oxynitride, and silicon nitride may be used. It is possible.

[0194] An EL layer 315 and a second electrode 316 are stacked on the first electrodes (313a, 313b). The EL layer 315 is provided with at least a light-emitting layer, and is connected to the first electrode (313a , 313b), an EL layer 315, and a light-emitting element (317a, 317b) consisting of a second electrode 316. b) has a structure in which the edge of the EL layer 315 is covered with a second electrode 316. The layer 315 may have a single layer structure or a stacked layer structure as shown in Embodiment 2 or 3. Furthermore, it may be different for each light-emitting element.

[0195] The first electrodes (313a, 313b), the EL layer 315, and the second electrode 316 are made of As the material, the material shown in Embodiment 2 can be used. The first electrodes (313a, 313b) of the first electrodes (313a, 313b) are routed in the region 321. An external signal is input via an FPC 308 electrically connected to the wiring 307. The second electrodes 316 of the optical elements (317a, 317b) are routed in the region 322. The line 323 is electrically connected to the FPC 308, which is not shown here, and an external signal is input via the FPC 308. is entered.

[0196] In addition, in the cross-sectional view shown in FIG. 3(B), only two light-emitting elements (317a, 317b) are shown. However, in the pixel portion 302, a plurality of light-emitting elements are arranged in a matrix. That is, the pixel section 302 has an emission element that can emit two kinds of light (for example, (B, Y)). Not only elements, but also light-emitting elements that emit three types of light (for example, (R, G, B)) and four types Light-emitting elements that emit light (for example, (R, G, B, Y) or (R, G, B, W)) By forming each of these, a light emitting device capable of full color display can be formed. When forming the light-emitting layer, different materials are used depending on the light-emitting color of the light-emitting element. (so-called separate coating) or a plurality of light emitting elements may be formed using the same material. It has a common light-emitting layer and can be combined with a color filter to achieve full color. In this way, by combining light emitting elements that can emit several types of light, it is possible to This can improve purity and reduce power consumption. By combining these, a light emitting device with improved luminous efficiency and reduced power consumption may be obtained.

[0197] Furthermore, by bonding the sealing substrate 306 to the element substrate 301 with the sealing material 305, A space 318 surrounded by the element substrate 301, the sealing substrate 306, and the sealant 305 contains a light-emitting element. The structure is equipped with two arms (317a, 317b).

[0198] Furthermore, the sealing substrate 306 is provided with a color layer (color filter) 324. A black layer (black matrix) 325 is provided between the colored layers. A colored layer (color filter) adjacent to the layer (black matrix) 325 so as to overlap with the layer (black matrix) 325. Alternatively, one or both of the light emitting elements 317a and 317b may be provided. The resulting light is extracted to the outside through the colored layer (color filter) 324.

[0199] The space 318 may be filled with an inert gas (nitrogen, argon, etc.) or may be sealed. This also includes a configuration in which the substrate is filled with a sealant 305. In this case, it is preferable to perform either UV treatment or heat treatment, or a combination of these. .

[0200] It is also preferable to use epoxy resin or glass frit for the sealing material 305. It is desirable that these materials be as impermeable to moisture and oxygen as possible. Materials used for the sealing substrate 306 include glass substrates, quartz substrates, and FRP (Fiber-Reinforced Plastics). reinforced plastics), PVF (polyvinyl fluoride), polyester A plastic substrate made of polyethylene or acrylic resin can be used. When glass frit is used as the adhesive, the element substrate 301 and the sealing substrate 302 are 06 is preferably a glass substrate.

[0201] The structure of the FET electrically connected to the light emitting element differs from that shown in FIG. 3(B) in that the position of the gate electrode is FET326, FET327, and FET328 shown in FIG. 3(C) have different structures. The colored layer (color filter) 3 provided on the sealing substrate 306 may be formed as shown in FIG. 24 is positioned so as to overlap with the black layer (black matrix) 325 as shown in FIG. 3(C). Furthermore, it may be provided so as to overlap with the adjacent colored layer (color filter) 324 .

[0202] In this manner, an active matrix light emitting device can be obtained.

[0203] Further, the light-emitting device according to one embodiment of the present invention may be an active matrix light-emitting device. It is also possible to use a passive matrix light emitting device.

[0204] 4(A) and (B) show a passive matrix light-emitting device. FIG. 4B shows a top view of a matrix light-emitting device, and FIG. 4B shows a cross-sectional view thereof.

[0205] As shown in FIGS. 4A and 4B, a first electrode 402 and an EL layer (40 3a, 403b, and 403c) and a second electrode 404, a light-emitting element 405 is formed. The first electrode 402 is island-shaped and striped in one direction (horizontal direction in FIG. 4(A)). A plurality of stripes are formed on the first electrode 402. An insulating film 406 is formed on a part of the first electrode 402. A partition wall 407 made of an insulating material is provided on the insulating film 406. As shown in FIG. 4B, the side walls of the wall 407 are spaced apart from one another as they approach the substrate surface. The side wall has a slope that narrows the gap between it and the other side wall.

[0206] Since the insulating film 406 has an opening in a part above the first electrode 402, the EL layer (40 3a, 403b, 403c) and the second electrode 404 are arranged on the first electrode 402 in a desired shape. In Fig. 4(A) and Fig. 4(B), a mask such as a metal mask is used. The EL layers (403a, 403b, 403c) are formed by combining the insulating film 406 and the partition wall 407 on the insulating film 406. 4. An example of forming the EL layer 403a, the EL layer 403c, and the second electrode 404 is shown. b, EL layer 403c emits different light colors (for example, red, green, blue, yellow, orange, white, etc.). An example of this is shown below.

[0207] After the EL layers (403a, 403b, 403c) are formed, the second electrode 404 is formed. Therefore, the second electrode 404 is formed on the EL layer (403a, 403b, 403c). The first electrode 402 is not in contact with the second electrode 402 .

[0208] The sealing method is the same as that of the active matrix light emitting device. Therefore, the explanation will be omitted.

[0209] In this manner, a passive matrix light emitting device can be obtained.

[0210] For example, in this specification, a transistor or a light-emitting element is formed using various substrates. The type of substrate is not limited to a specific one. An example of the substrate is as follows: Examples include semiconductor substrates (such as single crystal substrates or silicon substrates), SOI substrates, and glass substrates. , quartz substrate, plastic substrate, metal substrate, stainless steel substrate, stainless steel Substrate with tungsten foil, tungsten substrate, substrate with tungsten foil, flexible Examples include: a flexible substrate, a laminated film, a paper containing fibrous material, or a base film. Examples of glass substrates include barium borosilicate glass, aluminoborosilicate glass, or Soda lime glass, etc. Flexible substrates, laminated films, base films, etc. Examples include polyethylene terephthalate (PET) ), polyethylene naphthalate (PEN), polyethersulfone (PES), polythene There are plastics such as tetrafluoroethylene (PTFE). Examples of the material include synthetic resins such as acrylic. ester, polyvinyl fluoride, or polyvinyl chloride. Polyamide, polyimide, aramid, epoxy, inorganic vapor deposition film, paper, etc. In particular, transistors are manufactured using semiconductor substrates, single crystal substrates, SOI substrates, etc. This results in less variation in characteristics, size, or shape, and a high current supply capacity. Small size transistors can be manufactured. By configuring the circuit, it is possible to reduce the power consumption of the circuit or to increase the integration density of the circuit.

[0211] In addition, a flexible substrate is used as the substrate, and a transistor or a light-emitting element is directly formed on the flexible substrate. Alternatively, a peeling layer may be provided between the substrate and the transistor or light-emitting element. The release layer may be used to separate the semiconductor device from the substrate after the semiconductor device is partially or entirely completed thereon. The resulting structure can be used for transferring the structure to other substrates, such as transistors or light-emitting devices. The element can be transferred onto a substrate having poor heat resistance or a flexible substrate. For example, a laminated structure of inorganic films such as a tungsten film and a silicon oxide film, or a polyimide film on a substrate, A configuration in which an organic resin film such as a fluorine-based resin film is formed can be used.

[0212] That is, a transistor or a light-emitting element is formed using a substrate, and then the transistor or the light-emitting element is transferred to another substrate. Transistors or light-emitting elements are transposed and arranged on another substrate. An example of the substrate onto which the transistor or the light-emitting element is transferred is In addition to substrates on which a transistor or a light-emitting element can be formed, paper substrates, cellophane substrates, Aramid film substrate, polyimide film substrate, stone substrate, wood substrate, cloth substrate (natural fiber Fibers (silk, cotton, linen), synthetic fibers (nylon, polyurethane, polyester) or recycled fibers Fiber (including acetate, cupro, rayon, recycled polyester, etc.), leather substrate, or The use of these substrates allows for the formation of transistors with good characteristics. Formation of low-power transistors, manufacturing of durable devices, imparting heat resistance, lightweight It is possible to achieve a smaller or thinner size.

[0213] Note that the structure shown in this embodiment mode may be used in appropriate combination with structures shown in other embodiment modes. It is possible.

[0214] (Embodiment 5) In this embodiment, various electronic devices completed by applying a light-emitting device which is one embodiment of the present invention will be described. We will explain the example of a car.

[0215] As an electronic device to which a light emitting device is applied, for example, a television set (television or television (also called television receivers), computer monitors, digital cameras, digital video Cameras, digital photo frames, mobile phones (also called mobile phones or mobile phone devices), mobile phones These include portable game machines, mobile information terminals, sound reproduction devices, and large game machines such as pachinko machines. Specific examples of these electronic devices are shown in Figures 5 and 6.

[0216] FIG. 5A shows an example of a television device. The television device 7100 is A display unit 7103 is built into the body 7101. The display unit 7103 displays images. It is possible to use a touch panel (input / output device) equipped with a touch sensor (input device). Note that the light-emitting device of one embodiment of the present invention can be used for the display portion 7103. In addition, the configuration in which the housing 7101 is supported by a stand 7105 is shown here. There are.

[0217] The television device 7100 can be operated using an operation switch provided on the housing 7101 or a separate remote control. This can be done using the remote control operation device 7110. The channel and volume can be controlled by the 7109, and the information displayed on the display 7103 is In addition, the remote control unit 7110 can be used to operate the video. A display unit 7107 for displaying information output from 7110 may be provided.

[0218] The television device 7100 is configured to include a receiver, a modem, etc. It is possible to receive more general television broadcasts, and also to receive them by wire or wirelessly via a modem. By connecting to a communication network, it can be transmitted in one direction (sender to receiver) or two directions (transmit to receiver). It is also possible to communicate information between followers and recipients, or between recipients themselves.

[0219] FIG. 5B shows a computer, which includes a main body 7201, a housing 7202, a display unit 7203, and a keyboard. It includes a board 7204, an external connection port 7205, a pointing device 7206, and the like. Note that the computer uses the light-emitting device of one embodiment of the present invention for the display portion 7203. The display portion 7203 can be manufactured by using a touch sensor (input device). It may also be a touch panel (input / output device) installed.

[0220] FIG. 5C shows a smartwatch, which includes a housing 7302, a display unit 7304, and an operation button 7307. 311, 7312, a connection terminal 7313, a band 7321, a clasp 7322, etc.

[0221] A display unit 7304 mounted on a housing 7302 that also serves as a bezel has a non-rectangular display area. The display unit 7304 has an icon 7305 representing the time, other icons 730 6, etc. The display portion 7304 is equipped with a touch sensor (input device). The display may be a touch panel (input / output device) mounted thereon.

[0222] The smartwatch shown in FIG. 5C can have various functions. For example, , the function to display various information (still images, videos, text images, etc.) on the display, Functions such as calendar, date or time display, various software (programs) It has the functions of controlling processing by wireless communication, and It has the function of connecting to a data network, and the function of transmitting or receiving various data using wireless communication. The function of reading out the program or data recorded on the recording medium and displaying it on the display unit. It can have functions such as:

[0223] In addition, a speaker, a sensor (force, displacement, position, velocity, acceleration, angular velocity) Degrees, rotation speed, distance, light, liquid, magnetism, temperature, chemical substances, sound, time, hardness, electric field, current, electricity Includes functions to measure pressure, power, radiation, flow rate, humidity, gradient, vibration, odor or infrared. The smart watch may have a light emitting device, a microphone, etc. The display portion 7304 can be manufactured by using the same.

[0224] 5(D), 5(D'-1), and 5(D'-2) are diagrams showing the configuration of a mobile phone (smartphone) The mobile phone 7400 includes a housing 7401, a display portion 7402, and a display unit 7403. , microphone 7406, speaker 7405, camera 7407, external connection part 7404, operation button Furthermore, the light-emitting element according to one embodiment of the present invention can be mounted on a flexible substrate. When a light-emitting device is manufactured by forming the light-emitting element on a substrate having a curved surface as shown in FIG. This can be applied to the 7402.

[0225] In a mobile phone 7400 shown in FIG. 5D, information can be displayed by touching the display portion 7402 with a finger or the like. You can also make a call or write an email using the This can be done by touching the display portion 7402 with a finger or the like.

[0226] The screen of the display unit 7402 has three main modes. The first is a display mode that mainly displays images. The first mode is a display mode, and the second mode is an input mode that mainly inputs information such as characters. This is a display + input mode that combines two modes: display mode and input mode.

[0227] For example, when making a call or creating an email, the display unit 7402 is used to input characters. This is the main character input mode, and you can input characters displayed on the screen. It is preferable to display a keyboard or number buttons on most of the screen of the display portion 7402. It's nice.

[0228] In addition, a detection device such as a gyro sensor or an acceleration sensor is provided inside the mobile phone 7400. By doing so, the orientation of the mobile phone 7400 (portrait or landscape) is determined, and the screen display of the display unit 7402 is can be set to switch automatically.

[0229] The screen mode can be switched by touching the display portion 7402 or by operating the housing 7401. The type of image displayed on the display unit 7402 can be selected by operating the button 7403. For example, the image signal to be displayed on the display unit can be switched by If the data is text data, the mode switches to display mode, and if the data is text data, the mode switches to input mode.

[0230] In the input mode, the optical sensor of the display unit 7402 detects a signal and displays it. If there is no input by touch operation on the part 7402 for a certain period of time, the screen mode is changed to the input mode. Alternatively, the display mode may be switched from the normal mode to the display mode.

[0231] The display portion 7402 can also function as an image sensor. By touching the device with your palm or fingers and capturing an image of your palm print or fingerprint, you can authenticate your identity. In addition, a backlight that emits near-infrared light to the display unit or a sensing light source that emits near-infrared light By using this, it is possible to capture images of finger veins, palm veins, etc.

[0232] Furthermore, as another configuration of a mobile phone (including a smartphone), Fig. 5(D'-1) and Fig. It can also be applied to a mobile phone having a structure such as 5(D'-2).

[0233] In addition, when the structure is as shown in Figure 5(D'-1) or Figure 5(D'-2), character information and Image information and the like are stored on the first surfaces 7501(1) and 7501(2) of the housings 7500(1) and 7500(2). (2), but can also be displayed on the second screen 7502(1) and 7502(2). With this structure, you can keep the mobile phone in your breast pocket. Uses text information and image information displayed on the second page 7502(1), 7502(2), etc. The person can easily verify this.

[0234] Furthermore, as an electronic device to which a light-emitting device is applied, a folding type as shown in FIGS. 6A shows a portable information terminal 931 in an unfolded state. 6(B) shows the state of the unfolded or folded state. The mobile information terminal 9310 is shown in a state in the process of changing. The portable information terminal 9310 is shown in a folded state. It is highly portable, and when unfolded, it has a seamless, wide display area that allows for excellent visibility of the display. can be.

[0235] The display unit 9311 is supported by three housings 9315 connected by hinges 9313. The display unit 9311 is a touch panel (input / output) equipped with a touch sensor (input device). The display unit 9311 may be connected to two housings via a hinge 9313. By bending the space between the terminals 9315, the portable information terminal 9310 can be folded from the unfolded state. The light-emitting device of one embodiment of the present invention can be reversibly transformed into a display portion 931. A display area 9312 in the display portion 9311 is in a folded state. The display area 9312 is a display area located on the side of the portable information terminal 9310. You can display icons and shortcuts for frequently used apps and programs. This allows you to check information and launch apps smoothly.

[0236] Also, a car to which the light emitting device is applied is shown in Fig. 7(A)(B). Specifically, the outer lane of the automobile shown in FIG. Door 5101 (including the rear of the car body), tire wheel 5102, part of door 5103 The display unit 51 shown in FIG. 7B can be applied to the entire vehicle. 04, steering wheel 5105, shift lever 5106, seat 5107, inner rear bi It can be applied to a glass window such as a mirror 5108. stomach.

[0237] As described above, electronic devices and automobiles can be obtained by applying the light-emitting device which is one embodiment of the present invention. It should be noted that the electronic devices and automobiles to which the present invention can be applied are not limited to those shown in the present embodiment. , and can be applied in any field.

[0238] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiment modes. It is possible.

[0239] (Sixth embodiment) In this embodiment, a structure of a lighting device manufactured using a light-emitting element which is one embodiment of the present invention will be described. This will be explained with reference to FIG.

[0240] 8(A), (B), (C), and (D) show examples of cross-sectional views of the lighting device. (A) and (B) are bottom-emission type lighting devices that extract light from the substrate side, as shown in Figure 8( C) and (D) are top-emission lighting devices that extract light from the encapsulation substrate side.

[0241] A lighting device 4000 shown in FIG. 8A has a light-emitting element 4002 on a substrate 4001. The light emitting element 4002 has a substrate 4003 having an uneven surface on the outer side of the substrate 4001. It has a first electrode 4004 , an EL layer 4005 , and a second electrode 4006 .

[0242] The first electrode 4004 is electrically connected to the electrode 4007, and the second electrode 4006 is electrically connected to the electrode 4008. 008. An auxiliary wiring electrically connected to the first electrode 4004. An insulating layer 4010 may be formed on the auxiliary wiring 4009. There are.

[0243] The substrate 4001 and the sealing substrate 4011 are bonded together with a sealant 4012. A desiccant 4013 is provided between the sealing substrate 4011 and the light emitting element 4002. It is preferable that the substrate 4003 has the unevenness as shown in FIG. The efficiency of extracting light generated in 02 can be improved.

[0244] In addition, instead of the substrate 4003, as in the illumination device 4100 of FIG. 8(B), A diffusion plate 4015 may be provided on the outside.

[0245] A lighting device 4200 in FIG. 8C has a light-emitting element 4202 over a substrate 4201. The element 4202 has a first electrode 4204, an EL layer 4205, and a second electrode 4206. .

[0246] The first electrode 4204 is electrically connected to the electrode 4207, and the second electrode 4206 is electrically connected to the electrode 4208. 208. The auxiliary wiring 4206 is electrically connected to the second electrode 4206. An insulating layer 4210 may be provided under the auxiliary wiring 4209. stomach.

[0247] The substrate 4201 and the sealing substrate 4211 having projections and recesses are bonded with a sealant 4212. In addition, a barrier film 4213 and a planarization film 4211 are provided between the sealing substrate 4211 and the light emitting element 4202. 4 may be provided. Note that since the sealing substrate 4211 has unevenness as shown in FIG. The extraction efficiency of light generated by the light emitting element 4202 can be improved.

[0248] In addition, instead of the sealing substrate 4211, a light-emitting element 4 is A diffuser plate 4215 may be provided on top of 202.

[0249] Note that the lighting device described in this embodiment includes a light-emitting element which is one embodiment of the present invention, a housing, a cover, and a light-emitting element. Alternatively, the light-emitting element may have a structure having a support base. An organometallic complex according to one embodiment of the present invention can be applied to 4205. It is possible to provide a lighting device with low power consumption.

[0250] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiment modes. It is possible.

[0251] (Embodiment 7) In this embodiment, one example of a lighting device, which is an application of the light-emitting device according to one embodiment of the present invention, will be described. An example will be described with reference to FIG.

[0252] FIG. 9 shows an example in which the light emitting device is used as an indoor lighting device 8001. It is also possible to make a large-area lighting device. By using a housing having a curved surface, it is possible to form a lighting device 8002 having a light-emitting area with a curved surface. The light-emitting element included in the light-emitting device shown in this embodiment mode is a thin film, and the design of the housing Therefore, lighting devices with a variety of elaborate designs can be formed. Furthermore, lighting devices 8003 may be provided on the walls of the room.

[0253] In addition to the above, by applying a light emitting device to some of the furniture installed in the room, The lighting device can have the following functions.

[0254] As described above, various lighting devices using the light-emitting device can be obtained. is included in one aspect of the present invention.

[0255] The structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiments. It is possible.

[0256] (Embodiment 8) In this embodiment, a light-emitting element according to one embodiment of the present invention or a light-emitting device according to one embodiment of the present invention is The touch panel will be described with reference to FIGS.

[0257] 10(A) and 10(B) are perspective views of the touch panel 2000. ) representative components of touch panel 2000 are shown for clarity.

[0258] The touch panel 2000 includes a display panel 2501 and a touch sensor 2595 (see FIG. 1 0(B)). The touch panel 2000 includes a substrate 2510, a substrate 2570, and a substrate It has a plate 2590.

[0259] The display panel 2501 has a plurality of pixels on a substrate 2510 and a display panel for supplying signals to the pixels. The plurality of wirings 2511 are arranged around the periphery of the substrate 2510. The wire is routed through a cable, part of which forms the terminal 2519. The terminal 2519 is an FPC2509 (1) and electrically connect.

[0260] The substrate 2590 has a touch sensor 2595 and a The plurality of wirings 2598 are routed around the periphery of the substrate 2590. The terminal 2599 is connected to the FPC 2509 (2 ) is electrically connected to the back side of the substrate 2590 for clarity. Electrodes and wiring of the touch sensor 2595 provided on the surface facing the substrate 2510 are implemented. It is shown by a line.

[0261] As the touch sensor 2595, for example, a capacitance type touch sensor can be applied. The capacitance type includes a surface capacitance type, a projected capacitance type, and the like.

[0262] Projected capacitive touch panels are classified into self-capacitance and mutual-capacitance types, which differ mainly in their drive methods. The mutual capacitance method is preferable because it allows simultaneous multi-point detection.

[0263] First, when applying a projected capacitive touch sensor, we will use Figure 10(B) to In the case of the projected capacitive type, the proximity or contact of a detection target such as a finger is detected. Various sensors can be applied that can detect.

[0264] The projected capacitive touch sensor 2595 has an electrode 2591 and an electrode 2592. The electrodes 2591 and 2592 are connected to different wirings among the plurality of wirings 2598. 10(A)(B), the electrode 2592 is repeatedly connected in one direction. A shape in which multiple quadrilaterals are repeatedly arranged and connected in one direction by wiring 2594 at the corners. The electrode 2591 also has a shape in which multiple quadrilaterals are connected at the corners, but the connected The direction in which the electrodes 2591 are connected intersects with the direction in which the electrodes 2591 are connected. The direction in which the electrode 2592 is connected is not necessarily perpendicular to the direction in which the electrode 2592 is connected. This is not necessary, and they may be arranged to form an angle greater than 0 degrees but less than 90 degrees.

[0265] It is preferable that the area of ​​the intersection of the wiring 2594 with the electrode 2592 be as small as possible. This makes it possible to reduce the area of ​​the region where no electrodes are provided, and to reduce variations in transmittance. As a result, the variation in brightness of light passing through the touch sensor 2595 can be reduced. It is possible.

[0266] The shapes of the electrodes 2591 and 2592 are not limited to this and may take various shapes. For example, multiple electrodes 2591 are arranged with as few gaps as possible, and are connected via an insulating layer. In this case, two adjacent electrodes 2592 may be provided. If a dummy electrode electrically isolated from these is provided between the two, the surface of the area with different transmittance can be This is preferable because it can reduce the product.

[0267] Next, the touch panel 2000 will be described in detail with reference to FIG. 11. 10(A) along the dashed line X1-X2.

[0268] The touch panel 2000 includes a touch sensor 2595 and a display panel 2501 .

[0269] The touch sensor 2595 is made up of electrodes 2591 and 2592 arranged in a staggered pattern in contact with the substrate 2590. and an insulating layer 2593 covering the electrodes 2591 and 2592; The electrodes 2591 are electrically connected to each other through wiring 2594. An electrode 2592 is provided between them.

[0270] The electrode 2591 and the electrode 2592 can be formed using a light-transmitting conductive material. Examples of the conductive material having light-transmitting properties include indium oxide, indium tin oxide, and indium Conductive oxides such as gallium zinc oxide, zinc oxide, and gallium-doped zinc oxide can be used. A graphene compound can also be used. When used, it can be formed by reducing, for example, graphene oxide formed in a film form. The reduction method can be a method of applying heat or a method of irradiating a laser. do.

[0271] The electrodes 2591 and 2592 can be formed using, for example, a conductive material having light-transmitting properties. After forming a film on the substrate 2590 by sputtering, various methods such as photolithography are used. The patterning technique can be used to remove unnecessary portions.

[0272] The insulating layer 2593 may be made of a resin such as an acrylic resin or an epoxy resin. In addition to resins with siloxane bonds, silicon oxide, silicon oxynitride, aluminum oxide, For example, inorganic insulating materials such as rubber can be used.

[0273] In addition, the wiring 2594 formed in part of the insulating layer 2593 allows the adjacent electrodes 2591 to The wiring 2594 is made of the same material as the electrode 2591 and the electrode 259 By using a material with higher conductivity than the material used in 2, electrical resistance can be reduced. This is preferable because it can be done easily.

[0274] The wiring 2598 is electrically connected to the electrode 2591 or the electrode 2592. A part of the wiring 2598 functions as a terminal. , gold, platinum, silver, nickel, titanium, tungsten, chromium, molybdenum, iron, cobalt Metallic materials such as copper or palladium, or alloy materials containing such metallic materials can be used. do.

[0275] In addition, the terminal 2599 electrically connects the wiring 2598 and the FPC 2509(2). Terminal 2599 is made of various anisotropic conductive films (ACF). Conductive Film) and Anisotropic Conductive Paste (ACP) tropic conductive paste) can be used.

[0276] In addition, an adhesive layer 2597 is provided in contact with the wiring 2594. 95 is attached to the display panel 2501 via an adhesive layer 2597 so as to overlap it. The surface of the display panel 2501 that is in contact with the adhesive layer 2597 is as shown in FIG. A substrate 2570 may be included, but is not required.

[0277] The adhesive layer 2597 is translucent. For example, a thermosetting resin or an ultraviolet curing resin may be used. Specifically, acrylic resin, urethane resin, epoxy resin, or white resin can be used. Xanthane-based resins can be used.

[0278] The display panel 2501 shown in FIG. 11A has a matrix between a substrate 2510 and a substrate 2570. The pixel has a plurality of pixels arranged in a square shape and a driving circuit. and a pixel circuit that drives the element.

[0279] FIG. 11A shows a pixel 2502R as an example of a pixel of the display panel 2501. A scanning line driver circuit 2503g is shown as an example of a driving circuit.

[0280] The pixel 2502R has a light emitting element 2550R and a power supply for the light emitting element 2550R. The transistor 2502t can be used.

[0281] The transistor 2502t is covered with an insulating layer 2521. Note that the insulating layer 2521 is It has the function of flattening unevenness caused by previously formed transistors, etc. The insulating layer 2521 may be given a function of suppressing the diffusion of impurities. This is preferable because it can prevent the reliability of transistors and the like from being reduced due to diffusion.

[0282] The light-emitting element 2550R is electrically connected to the transistor 2502t via a wiring. The light emitting element 2550R is directly connected to the wiring. The end of one electrode of terminal 2550R is covered with insulator 2528.

[0283] The light emitting element 2550R has an EL layer between a pair of electrodes. A colored layer 2567R is provided at a position overlapping with the light emitting element 2550R. The light passes through the colored layer 2567R and is emitted in the direction of the arrow shown in the figure. A light-shielding layer 2567BM is provided at the end of the light-emitting element 2550R and the colored layer 2567R. A sealing layer 2560 is provided between them.

[0284] In addition, when the sealing layer 2560 is provided in the direction in which light from the light emitting element 2550R is extracted, In this case, the sealing layer 2560 preferably has light-transmitting properties. It is preferable that the refractive index be higher than that of the glass.

[0285] The scanning line driver circuit 2503g includes a transistor 2503t and a capacitor 2503c. The driver circuit and the pixel circuit can be formed on the same substrate in the same process. Similarly to the transistor 2502t of the pixel circuit, the driver circuit (scanning line driver circuit 2503g The transistor 2503t in the second embodiment is also covered with an insulating layer 2521.

[0286] In addition, a wiring 2511 capable of supplying a signal to the transistor 2503t is provided. A terminal 2519 is provided in contact with the wiring 2511. It is electrically connected to FPC2509(1), which transmits image signals and It has the function of supplying signals such as a print signal and a synchronization signal. A printed wiring board (PWB) may be attached.

[0287] A bottom-gate transistor is applied to the display panel 2501 shown in FIG. However, the structure of the transistor is not limited to this and various structures are possible. In addition, a transistor having a structure similar to that of transistor 2 shown in FIG. The transistor 502t and the transistor 2503t have a semiconductor layer containing an oxide semiconductor as a channel region. In addition, it can be used as a semiconductor layer containing amorphous silicon, a laser, A semiconductor layer containing polycrystalline silicon crystallized by annealing or other processes is used as a channel region. It can be used as follows.

[0288] In addition, a top-gate transistor different from the bottom-gate transistor shown in FIG. A structure in which a transistor is applied to the display panel 2501 is shown in FIG. Even if the structure of the transistor changes, the barrier that can be used in the channel region The same applies to ation.

[0289] The touch panel 2000 shown in FIG. 11(A) is configured such that light from pixels is An anti-reflection layer 2567p is formed on the surface from which light is emitted to the outside so as to overlap at least the pixels. It is preferable that the anti-reflection layer 2567p has a circular polarizing plate or the like. Cut.

[0290] The substrate 2510, the substrate 2570, and the substrate 2590 shown in FIG. 11(A) are, for example, water. Vapor permeability is 1×10 -5 g / (m 2 ·day) or less, preferably 1 × 10 -6 g / ( m 2 A material having a flexibility of not more than 100 sq. m can be preferably used. It is preferable to use materials whose thermal expansion coefficients are approximately the same for these substrates. is 1×10 -3 / K or less, preferably 5×10 -5 / K or less, more preferably 1×10 - 5 Examples of materials include those with a temperature of 1000 K or less.

[0291] Next, a touch panel 2000' having a different configuration from the touch panel 2000 shown in FIG. 12. However, as a touch panel similar to the touch panel 2000, can be applied.

[0292] FIG. 12 shows a cross-sectional view of the touch panel 2000′. The touch panel 200 shown in FIG. 0' is a touch sensor for the touch panel 2000 shown in FIG. 11 and the display panel 2501. The position of the 2595 is different. Here, we will only explain the different configurations, and The description of the touch panel 2000 will be used for the relevant parts.

[0293] The colored layer 2567R is located at a position overlapping the light emitting element 2550R. Light from the light emitting element 2550R is emitted in the direction in which the transistor 2502t is provided. That is, (a part of) the light from the light emitting element 2550R is transmitted through the colored layer 2567R. The light is then emitted in the direction of the arrow shown in the figure. 67BM is provided.

[0294] The touch sensor 2595 is a touch sensor that is connected to the light emitting element 2550R of the display panel 2501. It is provided on the side where the transistor 2502t is provided (see FIG. 12(A)).

[0295] The adhesive layer 2597 is in contact with the substrate 2510 of the display panel 2501. In the case of the structure shown in FIG. 2(A), the display panel 2501 and the touch sensor 2595 are bonded together. However, the display panel 2501 and the touch panel 2502 are bonded together by the adhesive layer 2597. The substrate 2510 may not be provided between the sensor 2595 and the substrate 2510 .

[0296] In addition, in the same manner as in the case of the touch panel 2000, the touch panel 2000' also has a display panel Transistors with various structures can be applied to 2501. In the above, a case where a bottom gate transistor is applied is shown. As shown in B), a top gate type transistor may be applied.

[0297] Next, an example of a method for driving a touch panel will be described with reference to FIG.

[0298] FIG. 13(A) is a block diagram showing the configuration of a mutual capacitance type touch sensor. In A), a pulse voltage output circuit 2601 and a current detection circuit 2602 are shown. In 13(A), the electrodes 2621 to which the pulse voltage is applied are designated as X1-X6, and the change in current is The electrodes 2622 for detecting the voltage are designated Y1-Y6, and are illustrated with six wires each. 13A shows a capacitance 2 formed by overlapping an electrode 2621 and an electrode 2622. 603. The electrode 2621 and the electrode 2622 have functions interchangeable with each other. That's fine.

[0299] The pulse voltage output circuit 2601 is a circuit for applying pulse voltages to the wires X1-X6 in order. When a pulse voltage is applied to the wiring of X1-X6, a capacitance 2603 is formed. An electric field is generated between the electrodes 2621 and 2622. The electric field generated between the electrodes may cause shielding or the like. This generates a change in the mutual capacitance of the capacitor 2603, and the proximity of the object to be detected or can detect contact.

[0300] The current detection circuit 2602 detects the change in mutual capacitance at the capacitor 2603, and detects the change in the wiring between Y1 and Y6. The Y1-Y6 wiring detects the proximity of the object to be detected, or the change in the current. The detected current value does not change if there is no contact or proximity of the object to be detected. When the mutual capacitance decreases due to contact, a decrease in the current value is detected. This can be done using an integrating circuit or the like.

[0301] Next, FIG. 13(B) shows the input / output of the mutual capacitance type touch sensor shown in FIG. 13(A). FIG. 13(B) shows the timing chart of the output waveform of each row and column in one frame period. In addition, in FIG. 13(B), when the object to be detected is not detected (non-detection), The two cases shown are when a touch is detected and when an object is detected. For the wires Y1-Y6, the waveforms are shown as voltage values ​​corresponding to the detected current values. do.

[0302] A pulse voltage is applied to the wires X1-X6 in order, and the wires Y1-Y The waveform on wire 6 changes. When there is no proximity or contact of the object to be detected, the waveform on wire X1-X6 The waveforms of Y1-Y6 change uniformly according to the change in the voltage of the wiring. At the point where the current decreases, the waveform of the voltage also changes. In this way, by detecting the change in mutual capacitance, the proximity or contact of the object to be detected can be detected. It is possible.

[0303] In addition, in FIG. 13(A), a panel in which only a capacitor 2603 is provided at the intersection of the wiring as a touch sensor is used. The configuration of a passive type touch sensor has been shown, but an active type with a transistor and a capacitor may also be used. The touch sensor shown in FIG. 14 is one of the sensors included in the active type touch sensor. 1 shows an example of a capacitor circuit.

[0304] The sensor circuit shown in FIG. 14 includes a capacitor 2603, a transistor 2611, and a transistor 2621. 612 and a transistor 2613.

[0305] A signal G2 is applied to the gate of the transistor 2613, and a voltage is applied to either the source or the drain. A voltage VRES is applied, and the other is connected to one electrode of the capacitor 2603 and the The transistor 2611 has a source and a drain electrically connected to the gate. It is electrically connected to either the source or the drain of the transistor 2612, and the other is connected to the voltage VSS. The transistor 2612 receives a signal G1 at its gate and a signal G2 at its source or drain. The other electrode of the capacitor 2603 is electrically connected to the wiring ML. is given.

[0306] Next, the operation of the sensor circuit shown in Figure 14 will be described. First, the signal G2 is When a potential that turns on the transistor 2613 is applied, the gate of the transistor 2611 A potential corresponding to the voltage VRES is applied to the connected node n. Next, as the signal G2 By applying a potential that turns off the transistor 2613, the potential of the node n is maintained. Next, the mutual capacitance of the capacitor 2603 changes when a finger or other object to be detected approaches or touches the capacitor. As the voltage at node n changes, the potential at node n changes from VRES.

[0307] In the read operation, a potential that turns on the transistor 2612 is applied as the signal G1. The current flowing through the transistor 2611 in response to the potential of the node n, that is, the current flowing through the wiring ML The current changes, and by detecting this current, the proximity or contact of the object to be detected can be detected. It is possible.

[0308] The transistors 2611, 2612, and 2613 are made of oxides. It is preferable to use a nitride semiconductor layer as the semiconductor layer in which the channel region is formed. By applying such a transistor to the transistor 2613, the potential of the node n can be kept low for a long time. This allows the voltage to be held for a certain period of time, and the operation of resupplying VRES to node n (lift This can reduce the frequency of reshuffling.

[0309] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiment modes. It is possible.

[0310] (Embodiment 9) In this embodiment, a reflective display device including a light-emitting element of one embodiment of the present invention is It has a liquid crystal element and a light-emitting element, and can perform display in both transmission mode and reflection mode. Such a display device will be described with reference to FIGS. 15 to 17. ,ER-hybrid display(Emissive OLED and Ref It can also be called an eclectic LC Hybrid display.

[0311] Note that the display device described in this embodiment mode operates in a reflective mode in a place where external light is bright, such as outdoors. On the other hand, the display using this technology can be driven with extremely low power consumption. In places with low ambient light, such as in the dark, the display uses the transmissive mode to display images at optimal brightness. Therefore, by combining these and displaying them, To achieve a display with lower power consumption and higher contrast than conventional display panels. can be done.

[0312] An example of a display device shown in this embodiment mode is a display device including a liquid crystal element having a reflective electrode, a light-emitting element, and a In the reflective mode, an opening in the reflective electrode is provided at the position where the light emitting element overlaps. Visible light is reflected by the reflective electrode, and in the transmissive mode, it is emitted from the opening of the reflective electrode. The display device having a structure in which light from the elements is emitted is shown. The transistors used to drive the semiconductor device (electrode and light-emitting element) are arranged on the same plane. It is also preferable that the liquid crystal element and the light emitting element are stacked with an insulating layer interposed therebetween. is preferred.

[0313] FIG. 15A shows a block diagram of a display device described in this embodiment. 0 has a circuit (G) 501, a circuit (S) 502, and a display unit 503. In the section 503, a plurality of pixels 504 are arranged in a matrix in directions R and C. In addition, the circuit (G) 501 includes a wiring G1, a wiring G2, a wiring ANO, and a wiring CSCOM. Each of these is electrically connected to a plurality of wires, and these wires are arranged in a direction R. The circuit (S) 502 is also electrically connected to the pixel 504. The wiring S1 and the wiring S2 are , each of which is electrically connected, and these wirings are arranged in a direction C. The pixel 504 is also electrically connected to the pixel 504 .

[0314] The pixel 504 has a liquid crystal element and a light emitting element, which overlap each other. .

[0315] FIG. 15B1 shows a conductive film 50 which functions as a reflective electrode of a liquid crystal element included in a pixel 504. The shape of the conductive film 505 is shown in FIG. 5. An opening 506 is formed in a part of the conductive film 505 at a position where the conductive film 505 overlaps with the light-emitting element. That is, the light from the light emitting element passes through the opening 507. It is ejected.

[0316] The pixel 504 shown in FIG. 15(B1) is arranged so that the pixels 504 adjacent to it in the direction R exhibit different colors. Furthermore, the openings 507 are arranged so as not to be aligned in a line in the direction R. Such an arrangement allows the light-emitting elements of adjacent pixels 504 to be It has the effect of suppressing crosstalk between elements. Furthermore, it makes it easier to form elements. It also has the advantage of being

[0317] The shape of the opening 507 may be, for example, a polygon, a rectangle, an ellipse, a circle, a cross, or the like. The shape may also be elongated stripes, slits, or the like.

[0318] As a variation of the arrangement of the conductive film 505, the arrangement shown in FIG. 15(B2) is Good too.

[0319] The ratio of the opening 507 to the total area of ​​the conductive film 505 (excluding the opening 507) is That is, if the area of ​​the opening 507 is large, the display by the liquid crystal element will be affected. If the area of ​​the opening 507 is small, the display by the light emitting element becomes dark. In addition to the above ratio, when the area of ​​the opening 507 itself is small, the emission This causes a problem of a decrease in the efficiency of extracting light emitted from the optical element. The ratio of the area of ​​the opening 507 to the total area of ​​the film 505 (excluding the opening 507) is as follows: The range of 5% to 60% is necessary to maintain the display quality when combining the liquid crystal element and the light emitting element. It is highly preferable.

[0320] Next, an example of the circuit configuration of the pixel 504 will be described with reference to FIG. Two pixels 504 are shown.

[0321] The pixel 504 includes a transistor SW1, a capacitance element C1, a liquid crystal element 510, and a transistor SW 2, a transistor M, a capacitance element C2, and a light emitting element 511. Any of wiring G1, wiring G2, wiring ANO, wiring CSCOM, wiring S1, and wiring S2 In the pixel 504, the liquid crystal element 510 is electrically connected to the wiring VCOM. The light emitting element 511 is electrically connected to the wiring VCOM2.

[0322] The gate of the transistor SW1 is connected to the wiring G1. One of the source and the drain is connected to the wiring S1, and the other of the source and the drain is connected to the capacitor element One electrode of C1 and one electrode of the liquid crystal element 510 are connected. The other electrode of C1 is connected to the wiring CSCOM. The electrode is connected to a wiring VCOM1.

[0323] The gate of the transistor SW2 is connected to the wiring G2. One of the source and the drain is connected to the wiring S2, and the other of the source and the drain is connected to the capacitor element One electrode of the capacitance element C2 is connected to the gate of the transistor M. The other electrode is connected to one of the source and drain of the transistor M and the wiring ANO. The other of the source and drain of the transistor M is connected to one of the light emitting elements 511. The other electrode of the light emitting element 511 is connected to the wiring VCOM2. It has been done.

[0324] The transistor M has two gates sandwiching a semiconductor. By using this structure, the amount of current that the transistor M flows can be increased.

[0325] The signal applied from the wiring G1 turns the transistor SW1 on or off. A predetermined potential is applied from the wiring VCOM1. The alignment state of the liquid crystal in the liquid crystal element 510 can be controlled by the signal given from Also, a predetermined potential is applied from the wiring CSCOM.

[0326] The signal applied from the wiring G2 turns the transistor SW2 on or off. In addition, the potentials given from the wiring VCOM2 and the wiring ANO are controlled. The difference between the voltages causes the light emitting element 511 to emit light. The signal makes it possible to control the conduction state of transistor M.

[0327] Therefore, in the configuration shown in this embodiment, for example, in the reflective mode, the wiring G1 The liquid crystal element 510 is controlled by a signal given from the wiring S1, and the liquid crystal element 510 is displayed by using optical modulation. In the case of the transmission mode, the light given from the wiring G2 and the wiring S2 can be displayed. The light emitting element 511 can be made to emit light by the signal transmitted. When used, the wiring G1, the wiring G2, the wiring S1, and the wiring S2 are given. Based on the signal, desired driving can be performed.

[0328] Next, a cross-sectional schematic diagram of a display device 500 described in this embodiment is shown in FIG. 17, and details thereof will be described. do.

[0329] The display device 500 has a light emitting element 523 and a liquid crystal element 524 disposed between a substrate 521 and a substrate 522. The light-emitting element 523 and the liquid crystal element 524 are connected to each other via an insulating layer 525. That is, a light emitting element 523 is formed between a substrate 521 and an insulating layer 525. A liquid crystal element 524 is provided between a substrate 522 and an insulating layer 525 .

[0330] Between the insulating layer 525 and the light emitting element 523, a transistor 515, a transistor 516, The pixel includes a transistor 517, a coloring layer 528, and the like.

[0331] An adhesive layer 529 is provided between the substrate 521 and the light emitting element 523. From the insulating layer 525 side, a conductive layer 530 which becomes one electrode, an EL layer 531, and a conductive layer 532 which becomes the other electrode are arranged. The light-emitting element 523 has a stacked structure in which a conductive layer 532 is stacked in this order. Since the light-emitting element is a transmission type, the conductive layer 532 contains a material that reflects visible light and has a conductive The layer 530 includes a material that transmits visible light. The light passes through the insulating layer 525, passes through the opening 533, passes through the liquid crystal element 524, and then passes through the substrate It is ejected from 522 to the outside.

[0332] Between the insulating layer 525 and the substrate 522, in addition to the liquid crystal element 524, a colored layer 534, a light-shielding layer 53 5, an insulating layer 546, a structure 536, etc. The liquid crystal element 524 has one electrode a conductive layer 537 serving as the first electrode, a liquid crystal 538, a conductive layer 539 serving as the other electrode, and an alignment film 540 , 541, etc. The liquid crystal element 524 is a reflective liquid crystal element, and has a conductive layer 539 The conductive layer 537 is made of a material with high reflectivity because it functions as a reflective electrode. The conductive layer 537 and the conductive layer 538 are made of a material that transmits visible light to function as a light electrode. The insulating layer 539 has alignment films 540 and 541 on the liquid crystal 538 side. 546 is provided to cover the colored layer 534 and the light-shielding layer 535, and is an overcoat. The alignment films 540 and 541 may not be provided if they are not necessary.

[0333] An opening 533 is provided in a part of the conductive layer 539. The conductive layer 543 has a light-transmitting property, and therefore the conductive layer 543 is transparent to light. A material that transmits light is used.

[0334] The structure 536 has a space that prevents the insulating layer 525 and the substrate 522 from getting closer than necessary. The structure 536 does not have to be provided if it is not necessary.

[0335] Either the source or the drain of the transistor 515 is connected to the conductive layer 5 30. For example, the transistor 515 is electrically connected to the transistor shown in FIG. Corresponds to TaM.

[0336] Either the source or the drain of the transistor 516 is connected to the liquid crystal display panel 510 via a terminal portion 518. The conductive layer 539 and the conductive layer 543 of the element 524 are electrically connected. The portion 518 has a function of electrically connecting the conductive layers provided on both sides of the insulating layer 525. The transistor 516 corresponds to the transistor SW1 shown in FIG.

[0337] A terminal portion 519 is provided in the area where the substrate 521 and the substrate 522 do not overlap. The terminal portion 519 electrically connects the conductive layers provided on both sides of the insulating layer 525 to each other, similar to the terminal portion 518. The terminal portion 519 is connected to a conductive layer obtained by processing the same conductive film as the conductive layer 543. As a result, the terminal portion 519 and the FPC 544 are electrically connected to each other through the connection layer 545. The electrical connection can be made via the

[0338] In addition, a connection portion 547 is provided in a portion of the area where the adhesive layer 542 is provided. In the portion 547, a conductive layer obtained by processing the same conductive film as the conductive layer 543 and a conductive layer 5 37 are electrically connected by the connector 548. 7, a signal or potential input from the FPC 544 is supplied via the connector 548. This can be done.

[0339] A structure 536 is provided between the conductive layer 537 and the conductive layer 543. The structure 536 includes: It has the function of maintaining the cell gap of the liquid crystal element 524 .

[0340] The conductive layer 543 may be formed of a metal oxide, a metal nitride, a low-resistance oxide semiconductor, or the like. When an oxide semiconductor is used, it is preferable to use an oxide of hydrogen, boron, phosphorus, or the like. At least one of the concentrations of nitrogen and other impurities and the amount of oxygen vacancies is The conductive layer 543 may be made of a material having a higher thermal conductivity than the semiconductor layer used in the first embodiment.

[0341] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiment modes. It is possible.

[0342] (Embodiment 10) In this embodiment, a light-emitting element which is one embodiment of the present invention will be described. The light-emitting element described in this embodiment has a different configuration from the light-emitting element described in the second embodiment. The element structure of the light-emitting element and a method for manufacturing the same will be described with reference to FIGS. 31(A) and 31(B). However, the parts common to the light emitting device described in the second embodiment are the same as those in the second embodiment. Please refer to the explanation and the explanation will be omitted.

[0343] The light-emitting element described in this embodiment has a pair of electrodes (cathode 32) formed on a substrate 3200. 3201 and an anode 3203) and an EL layer 3202 including a light-emitting layer 3213 sandwiched therebetween. The EL layer 3202 has a light-emitting layer, a hole-injection layer, and a The layer can be formed by laminating a hole transport layer, an electron injection layer, an electron transport layer, and the like.

[0344] In this embodiment, as shown in FIG. 31(A), a cathode 320 formed on a substrate 3200 1, an electron injection layer 3214, an emitting layer 3213, a hole transport layer 3215, and a hole injection layer The EL layer 3202 is formed by sequentially stacking the hole injection layer 3216 and the anode 320. Here, a light-emitting element having a structure in which an electron transport layer 3 is formed will be described. Although not provided, by including a material with high electron transporting properties in the electron injection layer 3214, electrons It may also be formed to function as a transport layer.

[0345] The light emitting element described above emits light by applying a potential difference between the cathode 3201 and the anode 3203. The current flows, and the holes and electrons recombine in the EL layer 3202, causing light emission. This light is emitted to the outside through either or both of the cathode 3201 and the anode 3203. Therefore, either one or both of the cathode 3201 and the anode 3203 The electrode is a light-transmitting electrode, and light can be extracted from the light-transmitting electrode side.

[0346] In the light-emitting element shown in this embodiment, as shown in FIG. 31(A), the end of the cathode 3201 is insulated. The insulating material 3217 is covered with the adjacent insulating material 3217 as shown in FIG. The gap between the cathodes 3201 (for example, 3201a and 3201b) is filled. .

[0347] The insulator 3217 can be made of an insulating organic compound or an insulating inorganic compound. As the compound, a photosensitive resin (resist material, etc.) can be used. For example, acrylic A resin such as a polyimide resin, a fluorine resin, or the like can be used. Examples of the material that can be used include silicon oxide, silicon oxynitride, and silicon nitride. It is preferable that the surface of the insulator 3217 is water-repellent, and the treatment method and Examples of such treatment include plasma treatment and treatment with chemical solutions (alkaline solutions, organic solvents).

[0348] In this embodiment, the electron injection layer 3214 formed on the cathode 3201 is made of a polymer compound. However, the material is a polymer compound that is difficult to dissolve in non-aqueous solvents and has high electron transport properties. Specifically, in the second embodiment, the electron injection layer 115 and the electron The materials that can be used for the transport layer 114 include not only polymer compounds but also aluminum. Potassium metal, alkaline earth metal, or their compounds) are used in appropriate combinations, These are dissolved in a polar solvent and applied by a coating method.

[0349] The polar solvents used here include methanol, ethanol, propanol, and isopropyl alcohol. Examples include propanol, butyl alcohol, ethylene glycol, and glycerin.

[0350] The light-emitting layer 3213 is formed on the electron injection layer 3214. In the second embodiment, the materials (light-emitting materials) that can be used for the light-emitting layer 3213 are listed below. The ink is dissolved (or dispersed) in a non-polar solvent by a wet method (inkjet printing). The electron injection layer 32 is formed by film formation (or coating) using a jet method or a printing method. 14 is common to the light emitting elements with different luminescent colors, but the light emitting layer 3213 has As for non-polar solvents, aromatic solvents such as toluene and xylene are suitable. Heteroaromatic solvents such as hexane and pyridine can be used. Solvents such as 2-methylhexane, cyclohexane, and chloroform can be used.

[0351] As shown in FIG. 31(B), a device for applying a solution (hereinafter referred to as a solution application device) The ink for forming the light emitting layer 3213 is applied from the head part 3300. The head unit 3300 has a plurality of ejection units 3301a to 3301c that have the function of ejecting ink. Each of them is provided with piezoelectric elements 3302a to 3302c. Furthermore, each of the ejection parts 3301a to 3301c contains a luminescent material that emits a different luminescent color. It is filled with inks 3303a to 3303c.

[0352] Inks 3303a to 3303c are ejected from ejection sections 3301a to 3301c, respectively. As a result, light-emitting layers (3213a, 3213b, 3213c) with different luminescent colors are formed. is formed.

[0353] A hole transport layer 3215 is formed on the light emitting layer 3213. The hole transport layer 3215 is In the second embodiment, the materials listed as those usable for the hole transport layer 3215 are suitably used. The hole transport layer 3215 can be formed by vacuum deposition. The deposition method or the coating method can be used. When the coating method is used, the material dissolved in the solvent is The mixture is applied onto the light-emitting layer 3213 and the insulator 3217. For example, an ink jet method, a spin coating method, a printing method, etc. can be used.

[0354] In addition, a hole injection layer 3216 is formed on the hole transport layer 3215. An anode 3203 is formed on the top of the film. The layer can be formed by a vacuum deposition method using an appropriate combination of the above.

[0355] In this manner, a light-emitting element can be formed. When a certain organometallic complex is used, phosphorescence based on the organometallic complex can be obtained. A light-emitting element with higher efficiency than a light-emitting element using only a photoactive compound can be realized.

[0356] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiments. It shall be possible to do so. [Example]

[0357] <Synthesis Example 1> In this example, an organic gold compound represented by structural formula (100) in Embodiment 1, which is one embodiment of the present invention, was used. Complexes of bis(4,6-dimethyl-2-[5-(4-cyano-2,6-dimethylphenyl )-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2 ,2,6,6-tetramethyl-3,5-heptanedionato-κ 2 O,O') Iridium ( III) (abbreviation: [Ir(dmdppr-dmCP)2(dpm)]) The structure of [Ir(dmdppr-dmCP)2(dpm)] is shown below. vinegar.

[0358] [ka]

[0359] Step 1: Synthesis of 5-hydroxy-2,3-(3,5-dimethylphenyl)pyrazine > First, 5.27 g of 3,3',5,5'-tetramethylbenzyl and 2 g of glycinamide hydrochloride 0.61g, 1.92g of sodium hydroxide, and 50mL of methanol were placed in a three-neck flask equipped with a reflux condenser. The contents were placed in a flask, and the atmosphere inside the flask was replaced with nitrogen. After that, the contents were stirred at 80°C for 7 hours. 2.5 mL of 12 M hydrochloric acid was added to the mixture and stirred for 30 minutes. 2.02 g of ethanol was added and stirred for 30 minutes. After suction filtration of this suspension, the obtained solid was The desired pyrazine derivative was obtained by washing with methanol (milky white powder, yield 7.0). 9%). The synthesis scheme for step 1 is shown below in (a-1).

[0360] [ka]

[0361] Step 2: 5,6-bis(3,5-dimethylphenyl)pyrazin-2-yl triflate Synthesis of methylmethanesulfonic acid Next, the 5-hydroxy-2,3-(3,5-dimethylphenyl) pyridine obtained in step 1 above was 4.80 g of ethylenediamine, 4.5 mL of triethylamine, and 80 mL of dehydrated dichloromethane were added to a three-port flask. The flask was cooled to -20°C and then filled with trifluoride. 3.5 mL of fluoromethanesulfonic anhydride was added dropwise, and the mixture was stirred at room temperature for 17.5 hours. After cooling the LASCO to 0°C, add 0.7 mL of trifluoromethanesulfonic anhydride dropwise. The mixture was stirred at room temperature for 22 hours to react. 50 mL of water and 5 mL of 1 M hydrochloric acid were added to the reaction solution. Dichloromethane was added to extract the substances contained in the reaction solution into dichloromethane. This dichloromethane was washed with saturated aqueous sodium bicarbonate and saturated saline. After drying, the solution was filtered and the filtrate was concentrated to give The residue was separated by silica gel column chromatography using toluene:hexane = 1:1 (volume ratio) as a developing solvent. The product was purified by column chromatography to obtain the desired pyrazine derivative (yellow oil, 96% yield). The synthesis scheme for step 2 is shown below in (a-2).

[0362] [ka]

[0363] Step 3: 5-(4-cyano-2,6-dimethylphenyl)-2,3-bis(3,5 Synthesis of (-dimethylphenyl)pyrazine (abbreviation: Hdmdppr-dmCP) Next, 5,6-bis(3,5-dimethylphenyl)pyrazine-2- obtained in Step 2 above was 2.05g 4-cyano-2,6-dimethylphenyl trifluoromethanesulfonic acid 1.00 g of boronic acid, 3.81 g of potassium phosphate tripotassium, 40 mL of toluene, and 4 mL of water were added in three portions. The contents were placed in a flask and the inside of the flask was replaced with nitrogen. After degassing by stirring under reduced pressure, , tris(dibenzylideneacetone)dipalladium(0) 0.044g, tris(2,6 0.084 g of (-dimethoxyphenyl)phosphine was added and the mixture was refluxed for 7 hours. Toluene was added to extract the substances contained in the reaction solution into toluene. The mixture was washed with saturated saline and then dried by adding magnesium sulfate. The solution was filtered, and the filtrate was concentrated. The residue was dissolved in hexane:ethyl acetate=5:1 (body ratio The target pyrazine was purified by silica gel column chromatography using a 2000-methanol mixture (volume ratio) as the developing solvent. The derivative Hdmdppr-dmCP was obtained (white powder, 90% yield). The scheme is shown in (a-3) below.

[0364] [ka]

[0365] Step 4: Di-μ-chloro-tetrakis{4,6-dimethyl-2-[5-(4-chloro- (3,5-dimethylphenyl)-2-pyrazinyl -κN]phenyl-κC}diiridium(III) (abbreviation: [Ir(dmdppr-dm Synthesis of CP)2Cl]2) Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the Hdmdpp obtained in step 3 above were added. 1.74 g of r-dmCP (abbreviation), iridium chloride hydrate (IrCl3·H2O) (full 0.60 g of HCl (manufactured by Yamazaki Metals) was placed in a recovery flask equipped with a reflux condenser, and the flask was filled with argon. After that, the mixture was irradiated with microwaves (2.45 GHz, 100 W) for 1 hour to induce a reaction. After the solvent was distilled off, the resulting residue was suction filtered and washed with hexane to obtain the binuclear complex [Ir( (dmdppr-dmCP)Cl) was obtained (brown powder, 89% yield). The synthesis scheme of 4 is shown below in (a-4).

[0366] [ka]

[0367] Step 5: Bis{4,6-dimethyl-2-[5-(4-cyano-2,6-dimethylfluor] (phenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC }(2,2,6,6-tetramethyl-3,5-heptanedionato-κ 2 O,O') Iriji Synthesis of Ir(III) (abbreviation: [Ir(dmdppr-dmCP)2(dpm)]) Furthermore, 30 mL of 2-ethoxyethanol and the dinuclear complex [Ir(dm dppr-dmCP)2Cl]20.96g, dipivaloylmethane (abbreviation: Hdpm) 0.26g of ammonium hydroxide and 0.48g of sodium carbonate were placed in a recovery flask equipped with a reflux condenser. The inside of the container was replaced with argon, and then microwaves (2.45 GHz, 100 W) were used for 60 minutes. Further, 0.13 g of Hdpm was added, and the reaction vessel was irradiated with microwaves (2.45 G The reaction was carried out by irradiating the mixture with a 1000 W (120 Hz) lamp for 60 minutes. The solvent was evaporated, and the resulting residue was Silica gel column chromatography was performed using a developing solvent of dichloromethane:hexane = 1:1 (volume ratio). The product was purified by chromatography using a silica gel column with dichloromethane as a developing solvent. After purifying by column chromatography, it was redissolved in a mixed solvent of dichloromethane and methanol. By crystallizing, the organometallic complex, [Ir(dmdppr-dm CP)2(dpm)] was obtained as a red powder (yield 37%). The resulting red powder solid was 0. 39g was purified by train sublimation. The conditions for the purification were a pressure of 2. The solid was heated to 300°C under 6 Pa and argon gas at a flow rate of 5 mL / min. After purification by sublimation, the target red solid was obtained in 85% yield. The synthesis scheme of Step 5 is shown below ( a-5).

[0368] [ka]

[0369] The red powder obtained in step 5 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 18. In the example, the organometallic complex represented by the above structural formula (100), [Ir(dmdppr -dmCP)2(dpm)] was obtained.

[0370] 1 H-NMR.δ(CD2Cl2):0.91(s,18H),1.41(s,6H), 1.95(s,6H),2.12(s,12H),2.35(s,12H),5.63( s,1H),6.49(s,2H),6.86(s,2H),7.17(s,2H),7 .34(s,4H),7.43(s,4H),8.15(s,2H).

[0371] Next, the UV spectroscopy of [Ir(dmdppr-dmCP)2(dpm)] in dichloromethane was performed. The visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and the emission spectrum are measured. The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation). A dichloromethane solution (0.010mmol / L) was placed in a quartz cell and measured at room temperature. The emission spectrum was measured using an absolute PL quantum yield measurement device (Hamamatsu Photonics Co., Ltd.). A glove box (LA, manufactured by Bright Co., Ltd.) was used. Dichloromethane deoxygenated solution under nitrogen atmosphere using BstarM13 (1250 / 780) (0.010 mmol / L) was placed in a quartz cell, sealed, and the measurement was carried out at room temperature. The measurement results of the absorption spectrum and emission spectrum are shown in Figure 19. The horizontal axis is wavelength, and the vertical axis is absorption. In addition, two solid lines are shown in Figure 19, but the thin solid line represents the intensity of the light emitted from the sample. The line indicates the absorption spectrum, and the thick solid line indicates the emission spectrum. The spectrum was measured by placing a dichloromethane solution (0.010 mmol / L) in a quartz cell. From the absorption spectrum measured by adding only dichloromethane to the quartz cell, The results are shown after subtracting the negative value.

[0372] As shown in Figure 19, the organometallic complex, [Ir(dmdppr-dmCP)2(dpm)] It has an emission peak at 635 nm, and red emission is observed from the dichloromethane solution. It was.

[0373] Next, the organometallic complex, [Ir(dmdppr-dmCP)2(dpm)], was purified by liquid chromatography. Graph mass spectrometry (Liquid Chromatography Mass Spect The results were analyzed by LC / MS (LC / MS analysis).

[0374] LC / MS analysis was performed using a Waters Acqui (liquid chromatography) system. Mass spectrometry (MS) was performed using a Waters Xevo UPLC (registered trademark). The LC separation was performed using an Acquity UPL G2 Tof MS. C BEH C8 (2.1 × 100 mm 1.7 μm), column temperature was 40°C. The mobile phase A was acetonitrile and the mobile phase B was 0.1% formic acid aqueous solution. The pull was prepared by dissolving [Ir(dmdppr-dmCP)2(dpm)] in chloroform at any concentration. The solution was dissolved and diluted with acetonitrile to adjust the injection volume to 5.0 μL.

[0375] A gradient method was used for LC separation, which changes the composition of the mobile phase. The mobile phase A:mobile phase B = 85:15, then the composition was changed, and the mobile phase B was The ratio of phase A to mobile phase B was set to mobile phase A:mobile phase B = 95:5. The composition was linear. was changed to.

[0376] For MS analysis, electrospray ionization was used. The capillary voltage was 3.0 kV and the sample was ionized by electrospray ionization (ESI). The sample cone voltage was 30 V, and detection was performed in positive mode. The m / z range was 100 to 1500.

[0377] The component m / z=1209.53 separated and ionized under the above conditions was placed in the collision cell. The ions were dissociated into product ions by colliding with argon gas in the cell. The energy (collision energy) when dissociating was set to 70 eV. The results of ion detection by time-of-flight (TOF) MS are shown in FIG.

[0378] From the results of FIG. 20, the organometallic complex represented by the structural formula (100), [Ir(dmdppr- dmCP)2(dpm)] mainly produces products around m / z = 1025, 609, and 417. It was found that the ion was detected. pr-dmCP)2(dpm)], and therefore, Important points in identifying [Ir(dmdppr-dmCP)2(dpm)] contained in the compound This can be said to be important data.

[0379] The product ion around m / z=1025 is the compound of structural formula (100). It is assumed to be a cation in the state where dipivaloylmethane and a proton are released, and m / z=1009 The product ions in the vicinity are presumed to be cations with a methyl group further removed from this one. The product ion around m / z=609 is the dipyridinium ion in the compound of structural formula (100). Valoylmethane and one ligand Hdmdppr-dmCP (abbreviation), proton released The product ion at m / z=417 is assumed to be a cation in the Hdmdp state. These are presumed to be cations of pr-dmCP, and are characteristic of the organometallic complexes that are an embodiment of the present invention. It is one of the signs.

[0380] Here, the organometallic complex synthesized in this example, [Ir(dmdppr-dmCP)2(dp m)] (Structural Formula: 100) and an organometallic complex having an alkyl group but not a cyano group; For [Ir(dmdppr-dmp)2(dpm)] (structural formula: 200), the sublimation temperature A high-vacuum differential thermobalance (manufactured by Bruker AXS, TG-DTA24) The measurement was carried out under vacuum conditions of 10 Pa and a heating rate of 10 °C / min. The results are shown in Figure 22. As can be seen from the figure, [Ir(dmdppr-dmC The sublimation temperature of [Ir(dmdppr-dmp)2 (dpm)] had a sublimation temperature of 240°C. P)2(dpm)] has a cyano group as a substituent, which increases the sublimation temperature. I found out that...

[0381] [ka]

[0382] In addition, the above two types of organometallic complexes were prepared under a vacuum of 5 to 8 × 10 -5 Pa chamber Within each, 2.0 × 10 -2 Desorbed gas components when sublimated at a rate of nm / sec The analysis was performed using a quadrupole mass spectrometer (ULVAC, residual gas analyzer Qulee BGM-20) The results are shown in Figure 21. In Figure 21, the horizontal axis represents the mass-to-charge ratio (m / z), and the vertical axis shows the pressure of a specific gas corresponding to the mass-to-charge ratio of the gas being measured inside the chamber ( The detected partial pressure is shown in Pa. As a result, [Ir(dmdppr-dmp)2(dpm)] is Although the sublimation temperature is lower than that of [Ir(dmdppr-dmCP)2(dpm)], From this, it is possible to conclude that the desorbed gas components with low molecular weight were detected. [Ir(dmdppr-dmCP)2(dpm)] is more thermally efficient than [Ir(dmdppr-dmCP)2(dpm)]. In other words, the organometallic complex [Ir(dmdp pr-dmCP)2(dpm)] has a high sublimation temperature due to the inclusion of a cyano group as a substituent. Despite the increased strength, the structure is resistant to thermal decomposition (low molecular weight decomposition products are less likely to be generated). It was confirmed that this is the case.

[0383] On the other hand, organometallic complexes containing cyano groups but no alkyl groups, such as [Ir(dpp The weight loss rate of [r-3CP)2(acac)] (structural formula: 201) was also measured using a high vacuum differential A differential thermobalance (manufactured by Bruker AXS, TG-DTA2410SA) The measurement was performed under a vacuum of 10 Pa, with a temperature rise rate of 10°C / min. The results are shown in Figure 22.

[0384] [ka]

[0385] As a result, the organometallic complex [Ir(dmdppr-dmCP)2(dp m)] (Structural formula: 100), and [Ir(dppr-3CP)2(acac)] (Structural formula: Formula 201) showed a similarly high sublimation temperature (around 280°C). As shown in Figure 22, the weight loss due to the sublimation of the ion is P)2(dpm)] (structural formula: 100) shows a weight loss rate of approximately 100%, The weight loss rate of [Ir(dppr-3CP)2(acac)] (structural formula: 201) is approximately However, the weight loss rate measured this time may have included measurement errors in weighing. Although these values ​​are not exact, it can be said that there is a large difference in the thermogravimetric curves of these organometallic complexes. When the temperature of [Ir(dppr-3CP)2(acac)] was increased, [Ir(dppr -3CP)2(acac)] was obtained as a carbonized residue, suggesting that the organometallic complex was formed during sublimation. It is thought that reactions and decomposition between the two bodies occur simultaneously. As a result, the phenyl group substituted on the pyrazine skeleton has an alkyl group as a substituent. This suppresses the reaction and decomposition of organometallic complexes during sublimation, reducing the generation of residues that accompany this. It was found that this could be done. [Example]

[0386] In this example, an organometallic complex, [Ir(dmdppr-dmCP) Light-emitting element 1 and light-emitting element 2 using [Ir(d mdppr-dmp)2(dpm)] (structural formula (200)) The light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 3 were fabricated as follows: This will be explained with reference to Fig. 23. The chemical formulas of the materials used in this example are shown below.

[0387] [ka]

[0388] <Fabrication of Light-Emitting Element 1, Light-Emitting Element 2, and Comparative Light-Emitting Element 3> First, indium tin oxide (ITO) containing silicon oxide is sputtered onto a glass substrate 900. The first electrode 901, which functions as an anode, was formed by deposition using a deposition method. The film thickness was set to 70 nm, and the electrode area was set to 2 mm x 2 mm.

[0389] Next, as a pretreatment for forming a light emitting element on the substrate 900, the substrate surface is washed with water. After baking at 200°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0390] Then 1×10 -4 The substrate is introduced into a vacuum deposition apparatus whose inside pressure has been reduced to about Pa. After vacuum baking at 170° C. for 30 minutes in the heating chamber of the deposition apparatus, the substrate 900 It was left to cool for about 30 minutes.

[0391] Next, the substrate 900 is placed in a vacuum deposition apparatus so that the surface on which the first electrode 901 is formed faces downward. In this example, the EL layer 902 was formed by vacuum deposition. The hole injection layer 911, the hole transport layer 912, the light emitting layer 913, the electron transport layer 914, and the electron The case where the implantation layer 915 is formed sequentially will be described.

[0392] 1×10 inside the vacuum chamber -4 After reducing the pressure to 100 Pa, 1,3,5-tri(dibenzothiophene- 4-yl)benzene (abbreviation: DBT3P-II) and molybdenum oxide to form DBT3P-I Ion and molybdenum oxide were co-deposited at a mass ratio of 4:2 on the first electrode 901. The hole injection layer 911 was formed. The film thickness was set to 20 nm. This is a deposition method in which materials are simultaneously evaporated from different evaporation sources.

[0393] Next, 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP) was evaporated to a thickness of 20 nm to form a hole transport layer 912 .

[0394] Next, a light-emitting layer 913 was formed on the hole-transporting layer 912 .

[0395] In the case of the light-emitting element 1, 2-[3'-(dibenzothiophen-4-yl)biphenyl-3- yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), N-( 1,1'-biphenyl-4-yl)-9,9-dimethyl-N-[4-(9-phenyl-9 PC BBiF), [Ir(dmdppr-dmCP)2(dpm)], 2mDBTBPDB q-II:PCBBiF:[Ir(dmdppr-dmCP)2(dpm)]=0.7: The mixture was co-deposited at a mass ratio of 0.3:0.06 to form a film with a thickness of 20 nm. mDBTBPDBq-II:PCBBiF:[Ir(dmdppr-dmCP)2(dp m)] = 0.8:0.2:0.06 (mass ratio), and the film thickness was set to 20 nm. In this manner, the light-emitting layer 913 of the light-emitting element 1 was formed to a thickness of 40 nm.

[0396] In the case of light-emitting element 2, the same material as light-emitting element 1 was used, and 2mDBTBPDBq-II:P CBBiF:[Ir(dmdppr-dmCP)2(dpm)]=0.7:0.3:0. 0.25 (mass ratio) to give a film thickness of 20 nm. PDBq-II:PCBBiF:[Ir(dmdppr-dmCP)2(dpm)]=0 The layers were co-deposited in a ratio of 0.8:0.2:0.025 (mass ratio) to a film thickness of 20 nm. As described above, the light-emitting layer 913 of the light-emitting element 2 was formed to a thickness of 40 nm.

[0397] In the case of comparative light-emitting element 3, 2mDBTBPDBq-II, PCBBiF, [Ir(dmd ppr-dmp)2(dpm)], 2mDBTBPDBq-II:PCBBiF:[I r(dmdppr-dmp)2(dpm)] = 0.7:0.3:0.05 (mass ratio) The film thickness was 20 nm. BBiF:[Ir(dmdppr-dmp)2(dpm)]=0.8:0.2:0.05 (mass ratio) to form a film having a thickness of 20 nm. The light-emitting layer 913 was formed to a thickness of 40 nm.

[0398] Next, 2mDBTB was added to the light-emitting layer 913 of each of the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 3. After depositing 20 nm of PDBq-II, 10 nm of Bphen was deposited as an electron transport layer. was formed.

[0399] Furthermore, lithium fluoride is evaporated to a thickness of 1 nm on the electron transport layer 914 to form an electron injection layer 915. did.

[0400] Finally, aluminum was evaporated onto the electron injection layer 915 to a thickness of 200 nm, and a shaded A second electrode 903 serving as a polarity electrode was formed, and the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 3 were obtained. In the above-mentioned deposition process, the deposition was all carried out by resistance heating.

[0401] The element structures of the thus obtained light-emitting element 1, light-emitting element 2, and comparative light-emitting element 3 are shown in Table 1. vinegar.

[0402] [Table 1]

[0403] The fabricated light-emitting element 1, light-emitting element 2, and comparative light-emitting element 3 were not exposed to the air. The device was sealed in a glove box with a nitrogen atmosphere (a sealant was applied around the device, UV treatment and heat treatment at 80°C for 1 hour during sealing.

[0404] <Operation Characteristics of Light-Emitting Element 1, Light-Emitting Element 2, and Comparative Light-Emitting Element 3> The operating characteristics of the fabricated light-emitting element 1, light-emitting element 2, and comparative light-emitting element 3 were measured. The measurements were carried out at room temperature (25°C).

[0405] FIG. 24 shows the current density-luminance characteristics of the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 3. The luminance characteristics are shown in Figure 25, the luminance-current efficiency characteristics are shown in Figure 26, and the voltage-current characteristics are shown in Figure 27. / m 2 The CIE chromaticities in the vicinity are shown in FIG.

[0406] Also, 1000cd / m 2 of the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 3 in the vicinity The main initial characteristic values ​​are shown in Table 2 below.

[0407] [Table 2]

[0408] 29 shows that the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 3 emit light at 2.5 mA / cm 2 Electricity As shown in FIG. 29, the emission spectra of the light-emitting elements 1 and 2 are shown when a current is applied at a current density of 1000 kJ / s. The emission spectrum of the light-emitting element 2 has a peak near 630 nm. The deep red color of the organometallic complex [Ir(dmdppr-dmCP)2(dpm)] is one example of the It is suggested that the emission is due to the [Ir(dmdppr Red light emission at around 619 nm originating from the β-dmp (dpm)2 (dpm) was confirmed. Furthermore, it can be seen that the introduction of a cyano group results in emission with higher color purity.

[0409] Next, a reliability test was performed on the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 3. The results of the performance test are shown in Figure 30. In Figure 30, the vertical axis represents the standard value when the initial luminance is 100%. The horizontal axis shows the rated luminance (%), and the horizontal axis shows the device operation time (h). Brightness: 5000cd / m 2 The current density was set to constant and the light-emitting elements 1, 2, and The comparative light-emitting element 3 was also driven.

[0410] When the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 3 were compared, it was found that the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 3 were The light-emitting layer is made of an organometallic complex, [Ir(dmdppr-dmCP)2(dpm)]. Light-emitting element 1 and light-emitting element 2 were made of [Ir(dmdppr-dmp)2(dpm)]. The results showed that the reliability was higher than that of the comparative light-emitting element 3 used in the light-emitting layer. As shown above, by having alkyl and cyano groups at appropriate positions, reactions between organometallic complexes can be easily performed. This makes it possible to suppress carbonization due to the vapor deposition and the generation of low molecular weight desorbed gases. Therefore, by using the organometallic complex according to one embodiment of the present invention, It can be seen that this can achieve a longer life for the light emitting element. [Example]

[0411] <Synthesis Example 2> In this example, an organometallic compound represented by structural formula (108) in Embodiment 1, which is one embodiment of the present invention, Complex, bis{4,6-dimethyl-2-[5-(5-cyano-2-methylphenyl)-3 -(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,2, 6,6-Tetramethyl-3,5-heptanedionato-κ 2 O,O') Iridium(III ) (abbreviation: [Ir(dmdppr-m5CP)2(dpm)]) The structure of [Ir(dmdppr-m5CP)2(dpm)] is shown below.

[0412] [ka]

[0413] Step 1: 5-(5-cyano-2-methylphenyl)-2,3-bis(3,5-dimethylphenyl)- Synthesis of (Hdmdppr-m5CP) First, 5,6-bis(3,5-dimethylphenyl)pyrazin-2-yltrifluoromethyl 1.83g phenylsulfonic acid, 0.79g 5-cyano-2-methylphenylboronic acid, phosphoric acid Put 3.17 g of tripotassium, 33 mL of toluene, and 3.3 mL of water into a three-neck flask. The atmosphere in the flask was replaced with nitrogen. After degassing by stirring under reduced pressure, tris(dibenzylidene) (acetone)dipalladium(0) 0.038g, tris(2,6-dimethoxyphenyl) 0.075 g of phosphine was added and refluxed for 8 hours. After the reaction, extraction with toluene was performed. Then, flash column chromatography was performed using hexane:ethyl acetate = 5:1 as the developing solvent. The desired pyrazine derivative, Hdmdppr-m5CP (abbreviation) was obtained. White solid, 96% yield. The synthesis scheme for Step 1 is shown in (b-1) below.

[0414] [ka]

[0415] Step 2: Di-μ-chloro-tetrakis{4,6-dimethyl-2-[5-(5-chloro- (3,5-dimethylphenyl)-2-pyrazinyl-κN ]phenyl-κC}diiridium(III) (abbreviation: [Ir(dmdppr-m5CP) Synthesis of 2Cl]2) Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the Hdmdpp obtained in step 1 above were added. r-m5CP (abbreviation) 1.59 g, iridium chloride hydrate (IrCl3·H2O) (full 0.57 g of HCl (manufactured by Yamazaki Metals) was placed in a recovery flask equipped with a reflux condenser, and the flask was filled with argon. After that, the mixture was irradiated with microwaves (2.45 GHz, 100 W) for 1 hour to induce a reaction. After the solvent was distilled off, the resulting residue was suction filtered and washed with methanol to obtain the dinuclear complex, [I r(dmdppr-m5CP)2Cl2 was obtained (reddish-brown solid, yield 66%). The synthesis scheme of Peptide 2 is shown in (b-2) below.

[0416] [ka]

[0417] <Step 3: Synthesis of [Ir(dmdppr-m5CP)2(dpm)]> Furthermore, 20 mL of 2-ethoxyethanol and the dinuclear complex [Ir(dm dppr-m5CP)2Cl]20.65g, dipivaloylmethane (abbreviation: Hdpm) 0.25g of ammonium hydroxide and 0.33g of sodium carbonate were placed in a recovery flask equipped with a reflux condenser. The inside of the container was replaced with argon. After that, microwaves (2.45 GHz, 100 W) were irradiated for 2 hours. The resulting reaction solution was filtered under suction, and the filter cake was washed with water and methanol.

[0418] The obtained solid was purified by silica gel column chromatography using dichloromethane as a developing solvent. After purifying by the above procedure, the product was recrystallized in a mixed solvent of dichloromethane and methanol to give An organometallic complex, [Ir(dmdppr-mCP)(dpm)], according to one embodiment of the present invention The compound was obtained as a red powder (yield 44%). 0.31 g of the obtained red powder solid was added to a trainer. The sublimation purification was carried out under the conditions of a pressure of 2.7 Pa and argon gas. The solid was heated at 275°C while flowing water at a flow rate of 5 mL / min. A red solid was obtained in 84% yield. The synthetic scheme of Step 3 is shown below in (b-3).

[0419] [ka]

[0420] The red powder obtained in step 3 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 32. In the example, the organometallic complex represented by the above structural formula (108), [Ir(dmdppr -m5CP)2(dpm)] was obtained.

[0421] 1H-NMR.δ(CD2Cl2):0.95(s,18H),1.42(s,6H), 1.95(s,6H),2.38(s,12H),2.49(s,6H),5.68(s ,1H),6.48(s,2H),6.83(s,2H),7.20(s,2H),7. 35(s,4H),7.43(d,2H),7.62(d,2H),7.70(s,2H ),8.43(s,2H).

[0422] Next, the UV spectroscopy of [Ir(dmdppr-m5CP)2(dpm)] in dichloromethane was performed. The visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and the emission spectrum are measured. The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation). A dichloromethane solution (0.011 mmol / L) was placed in a quartz cell and measured at room temperature. The emission spectrum was measured using an absolute PL quantum yield measurement device (Hamamatsu Photonics Co., Ltd.). A glove box (LA, manufactured by Bright Co., Ltd.) was used. Dichloromethane deoxygenated solution under nitrogen atmosphere using BstarM13 (1250 / 780) (0.011 mmol / L) was placed in a quartz cell, sealed, and the measurement was carried out at room temperature. The measurement results of the absorption spectrum and emission spectrum are shown in Figure 33. The horizontal axis is wavelength, and the vertical axis is absorption. In addition, two solid lines are shown in Figure 33, but the thin solid line represents the intensity of the light emitted from the sample. The lines show the absorption spectrum, and the thick solid lines show the emission spectrum. The spectrum was measured by placing a dichloromethane solution (0.011 mmol / L) in a quartz cell. From the absorption spectrum measured by adding only dichloromethane to the quartz cell, The results are shown after subtracting the negative value.

[0423] As shown in FIG. 33, the organometallic complex, [Ir(dmdppr-mC P)2(dpm)] has an emission peak at 645 nm and is obtained from a dichloromethane solution. Red luminescence was observed. [Example]

[0424] <Synthesis Example 3> In this example, an organometallic compound represented by structural formula (114) in Embodiment 1, which is one embodiment of the present invention, Complex, bis{4,6-dimethyl-2-[5-(2-cyano-6-methylphenyl)-3 -(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,2, 6,6-Tetramethyl-3,5-heptanedionato-κ 2 O,O') Iridium(III ) (abbreviation: [Ir(dmdppr-m2CP)2(dpm)]) The structure of [Ir(dmdppr-m2CP)2(dpm)] is shown below.

[0425] [ka]

[0426] Step 1: 5-(2-cyano-6-methylphenyl)-2,3-bis(3,5-dimethylphenyl) Synthesis of (Hdmdppr-m2CP) First, 5,6-bis(3,5-dimethylphenyl)pyrazin-2-yltrifluoromethyl 1.40 g of benzoxanthate, 3-methyl-2-(4,4,5,5-tetramethyl-1,3, 2-Dioxaborolan-2-yl)benzonitrile 0.98g, Potassium phosphate tripotassium phosphate 2.4 8g of toluene, 26mL of toluene, and 2.6mL of water were placed in a three-neck flask, and the inside of the flask was replaced with nitrogen. After degassing the inside of the LASCO by stirring under reduced pressure, tris(dibenzylideneacetone) diperoxide was added. Radium(0) 0.029g, tris(2,6-dimethoxyphenyl)phosphine 0.0 After the reaction, extraction was carried out with toluene. Purified by silica gel column chromatography using a developing solvent of 5:1 ethyl acetate. The desired pyrazine derivative Hdmdppr-m2CP (abbreviation) was obtained (white solid, yield 8 5%). The synthesis scheme for step 1 is shown below in (c-1).

[0427] [ka]

[0428] Step 2: Di-μ-chloro-tetrakis{4,6-dimethyl-2-[5-(2-chloro- (3,5-dimethylphenyl)-2-pyrazinyl-κN ]phenyl-κC}diiridium(III) (abbreviation: [Ir(dmdppr-mCP) Synthesis of 2Cl]2) Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the Hdmdpp obtained in step 1 above were added. r-m2CP (abbreviation) 1.08 g, iridium chloride hydrate (IrCl3·H2O) (full 0.39 g of ethylenediamine dinitrate (manufactured by Yamazaki Metals) was placed in a recovery flask equipped with a reflux condenser, and the flask was filled with argon. After that, the mixture was irradiated with microwaves (2.45 GHz, 100 W) for 1 hour to induce a reaction. The resulting reaction solution was filtered under suction, and the residue was washed with methanol to obtain the binuclear complex [Ir(dm dppr-mCP)Cl (abbreviation) was obtained (orange solid, 44% yield). The synthesis scheme of 2 is shown below in (c-2).

[0429] [ka]

[0430] Step 3: Synthesis of [Ir(dmdppr-mCP)(dpm)] Furthermore, 20 mL of 2-ethoxyethanol and the dinuclear complex [Ir(dm dppr-m5CP)2Cl]2 (abbreviation) 0.59 g, dipivaloylmethane (abbreviation: Hd 0.22g of pm) and 0.31g of sodium carbonate were placed in a recovery flask equipped with a reflux condenser. The atmosphere in the flask was replaced with argon. Then, microwaves (2.45 GHz, 100 W) were applied for 2 The solvent was removed from the reaction solution by distillation, and the resulting residue was diluted with hexane:ethyl acetate. By purifying the compound by silica gel column chromatography using the compound as a developing solvent, The organometallic complex [Ir(dmdppr-m2CP)2(dpm)] (abbreviation) was synthesized as a deep red powder. (yield 10%). The synthesis scheme of step 3 is shown below in (c-3).

[0431] [ka]

[0432] The red powder obtained in step 3 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 34. In the example, the organometallic complex represented by the above structural formula (114), [Ir(dmdppr -m2CP)2(dpm)] was obtained.

[0433] 1 H-NMR.δ(CD2Cl2):0.94(s,18H),1.43(s,6H), 1.94(s,6H),2.23(s,6H),2.36(s,12H),5.64(s ,1H),6.49(s,2H),6.87(s,2H),7.18(s,2H),7. 39(s,4H),7.44(t,2H),7.53(d,2H),7.62(s,2H ),8.32(s,2H).

[0434] Next, the UV spectroscopy of [Ir(dmdppr-m2CP)2(dpm)] in dichloromethane was performed. The visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and the emission spectrum are measured. The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation). A dichloromethane solution (0.010mmol / L) was placed in a quartz cell and measured at room temperature. The emission spectrum was measured using an absolute PL quantum yield measurement device (Hamamatsu Photonics Co., Ltd.). A glove box (LA, manufactured by Bright Co., Ltd.) was used. Dichloromethane deoxygenated solution under nitrogen atmosphere using BstarM13 (1250 / 780) (0.010 mmol / L) was placed in a quartz cell, sealed, and the measurement was carried out at room temperature. The measurement results of the absorption spectrum and emission spectrum are shown in Figure 35. The horizontal axis is wavelength, and the vertical axis is absorption. In addition, two solid lines are shown in Figure 35, but the thin solid line represents the intensity of the light emitted from the sample. The line indicates the absorption spectrum, and the thick solid line indicates the emission spectrum. The spectrum was measured by placing a dichloromethane solution (0.010 mmol / L) in a quartz cell. From the absorption spectrum measured by adding only dichloromethane to the quartz cell, The results are shown after subtracting the negative value.

[0435] As shown in FIG. 35, the organometallic complex, [Ir(dmdppr-mC P)2(dpm)] has an emission peak at 648 nm and is obtained from a dichloromethane solution. Red luminescence was observed. [Example]

[0436] In this example, an organometallic complex, [Ir(dmdppr-m5CP) 2(dpm)] (structural formula (108)) and a light-emitting device 4 using [Ir(dmdppr-m2 CP)2(dpm)] (structural formula (114)) for comparison. Comparative light-emitting element 6 was fabricated using a compound semiconductor (mdppr-25dmp)2(dpm). The light-emitting element 4, the light-emitting element 5, and the comparative light-emitting element 6 were fabricated in the same manner as in Example 2. Since it can be manufactured in the same manner, the explanation will be omitted. The details are shown in Table 3. The chemical formulas of the materials used in this example are shown below.

[0437] [Table 3]

[0438] [ka]

[0439] <Operating characteristics of light-emitting element> The operating characteristics of each of the fabricated light-emitting elements (light-emitting element 4, light-emitting element 5, and comparative light-emitting element 6) were as follows. The measurements were carried out at room temperature (an atmosphere maintained at 25°C). 36 to 40.

[0440] These results indicate that the light-emitting element of one embodiment of the present invention exhibits favorable chromaticity and a high external quantum efficiency. It can be seen that the efficiency is 1000cd / m 2The main The initial characteristic values ​​are shown in Table 4 below.

[0441] [Table 4]

[0442] Furthermore, in FIG. 41, the light-emitting element 4 and the light-emitting element 5 are irradiated with 2.5 mA / cm 2 A current is passed through the As shown in FIG. 41, the emission spectrum of the light-emitting element 4 is 64 The peak is at about 3 nm, and the organometallic complex, [Ir(dm It is suggested that the emission is due to the emission of the β-glucan compound (dppr-m5CP)2(dpm). The emission spectrum of the optical element 5 has a peak at about 648 nm. The emission from the organometallic complex, [Ir(dmdppr-m2CP)2(dpm)] This suggests that there is.

[0443] Next, reliability tests were performed on the light-emitting element 4, the light-emitting element 5, and the comparative light-emitting element 6. The results of the reliability test are shown in Figure 42. In Figure 42, the vertical axis represents the initial luminance when 100% is used. The horizontal axis shows the normalized luminance (%), and the horizontal axis shows the driving time (h) of the device. Under constant current density conditions (50mA / cm 2 ) Light-emitting element 4, light-emitting element 5, and comparative light-emitting element Driven the 6.

[0444] As a result, compared with the comparative light-emitting element 6, the organometallic complex, [Ir(dm Light-emitting element 4 using [Ir(dmdpp All of the light-emitting devices 5 using [r-m2CP2(dpm)] as the light-emitting layer showed high reliability. As mentioned above, by having alkyl groups and cyano groups at appropriate positions, It is possible to suppress carbonization caused by reactions between metal complexes and the generation of low molecular weight desorbed gases. This is because decomposition during deposition is reduced. It is clear that the use of a metal complex can extend the life of the light-emitting element.

[0445] ≪Reference synthesis example≫ In this reference synthesis example, the organometallic complex bis{4, 6-dimethyl-2-[5-(2,5-dimethylphenyl)-3-(3,5-dimethylphenyl] Nyl)-2-pyrazinyl-κN]phenyl-κC}(2,2,6,6-tetramethyl-3 ,5-heptanedionato-κ 2 O,O')iridium(III) (abbreviation: [Ir(dmd The synthesis method of [Ir(d ppr-25dmp)2(dpm)]) is explained below. The structure of [(mdppr-25dmp)2(dpm)] is shown below.

[0446] [ka]

[0447] Step 1: Synthesis of 5-hydroxy-2,3-(3,5-dimethylphenyl)pyrazine > First, 5.27 g of 3,3',5,5'-tetramethylbenzyl and 2 g of glycinamide hydrochloride 0.61g, 1.92g of sodium hydroxide, and 50mL of methanol were placed in a three-neck flask equipped with a reflux condenser. The contents were placed in a flask, and the atmosphere inside the flask was replaced with nitrogen. After that, the contents were stirred at 80°C for 7 hours. 2.5 mL of 12 M hydrochloric acid was added to the mixture and stirred for 30 minutes. 2.02 g of ethanol was added and stirred for 30 minutes. After suction filtration of this suspension, the obtained solid was The desired pyrazine derivative was obtained by washing with methanol (milky white powder, yield 7.0). 9%). The synthesis scheme for step 1 is shown below in (d-1).

[0448] [ka]

[0449] Step 2: 5,6-bis(3,5-dimethylphenyl)pyrazin-2-yl triflate Synthesis of methylmethanesulfonic acid Next, the 5-hydroxy-2,3-(3,5-dimethylphenyl) pyridine obtained in step 1 above was 4.80 g of ethylenediamine, 4.5 mL of triethylamine, and 80 mL of dry dichloromethane were added in three portions. The flask was cooled to -20°C and then filled with trifle. 3.5 mL of methylisothiazolinone was added dropwise, and the mixture was stirred at room temperature for 17.5 hours. After cooling the flask to 0°C, add 0.7 mL of trifluoromethanesulfonic anhydride dropwise. The mixture was stirred at room temperature for 22 hours to react. Water and 5 mL of 1 M hydrochloric acid were added to the reaction solution, and the mixture was dichloromethane. The organic layer was extracted with hexane. The extract was then washed with saturated sodium bicarbonate solution, saturated sodium chloride solution, and hexane. The solution was washed with brine and dried over magnesium sulfate. The dried solution was filtered. The residue was concentrated and then extracted with silica gel column using toluene:hexane=1:1 as a developing solvent. The product was purified by column chromatography to obtain the desired pyrazine derivative (yellow oil, 96% yield). The synthesis scheme for step 2 is shown below in (d-2).

[0450] [ka]

[0451] Step 3: 5-(2,5-dimethylphenyl)-2,3-bis(3,5-dimethylphenyl)- Synthesis of (phenyl)pyrazine (abbreviation: Hdmdppr-25dmp) Next, 5,6-bis(3,5-dimethylphenyl)pyrazine-2- obtained in Step 2 above was 1.22g of 2,5-dimethylphenylboronic acid, 0. Put 51g of ammonium hydroxide, 2.12g of tripotassium phosphate, 20mL of toluene, and 2mL of water into a three-neck flask. The inside of the flask was degassed by stirring under reduced pressure, and then tris(diisopropyl alcohol) was added. benzylideneacetone)dipalladium(0) 0.026g, tris(2,6-dimethoxy 0.053 g of (phenyl)phosphine was added and the mixture was refluxed for 4 hours. Water was added to the reaction solution, and the mixture was heated in toluene. The organic layer was extracted with benzene. The resulting extract was washed with saturated saline and then washed with magnesium sulfate. The dried solution was filtered. The filtrate was concentrated, and the resulting residue was dissolved in toluene. The desired pyrazine derivative is obtained by purifying the compound by silica gel column chromatography using the compound as a developing solvent. Hdmdppr-25dmp was obtained (colorless oil, 97% yield). The team is shown below in (d-3).

[0452] [ka]

[0453] Step 4: Di-μ-chloro-tetrakis{4,6-dimethyl-2-[5-(2,5- (dimethylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl {Ir(dmdppr-25dmp)2C}diiridium(III) l]2) Synthesis> Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the Hdmdpp obtained in step 3 above were added. r-25dmp 1.04g, iridium chloride hydrate (IrCl3·H2O) (Furuya Metal 0.36 g of HCl (manufactured by the company) was placed in a recovery flask equipped with a reflux condenser, and the atmosphere in the flask was replaced with argon. Thereafter, the mixture was irradiated with microwaves (2.45 GHz, 100 W) for 1 hour to cause a reaction. After distilling off the solvent, the resulting residue was suction filtered and washed with methanol to give the binuclear complex [Ir(dm dppr-25dmp)2Cl2 was obtained (reddish-brown powder, 80% yield). The synthesis scheme of 4 is shown in (d-4) below.

[0454] [ka]

[0455] Step 5: Bis{4,6-dimethyl-2-[5-(2,5-dimethylphenyl)-3 -(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,2, 6,6-Tetramethyl-3,5-heptanedionato-κ 2 O,O') Iridium(III ) (Abbreviation: [Ir(dmdppr-25dmp)2(dpm)] Synthesis Furthermore, 30 mL of 2-ethoxyethanol and the dinuclear complex [Ir(dm dppr-25dmp)2Cl]21.58g, dipivaloylmethane (abbreviation: HDPM) 0.44g of HCl and 0.84g of sodium carbonate were placed in a recovery flask equipped with a reflux condenser. The inside of the scope was replaced with argon. Then, microwaves (2.45 GHz, 100 W) were used for 60 minutes. The solvent was evaporated, and the resulting residue was suction filtered with methanol. The obtained solid was washed with water and methanol, and then extracted with dichloromethane:hexane After purification by flash column chromatography using a developing solvent of 1:1, The organometallic complex [Ir(d (mdppr-25dmp)2(dpm)] was obtained as a red powder (yield 71%). 1.27 g of the resulting red powder solid was purified by train sublimation. The production conditions were a pressure of 2.6 Pa, argon gas flow rate of 5 mL / min, and a temperature of 250°C. The solid was heated at 100°C. After purification by sublimation, the target red solid was obtained in 92% yield. The synthesis scheme is shown in (d-5) below.

[0456] [ka]

[0457] The compound obtained in step 5 above was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR analysis The results are shown below. From this, it can be seen that in this Reference Synthesis Example, the organometallic complex, [Ir(dm It was found that the product [dppr-25dmp)2(dpm)] was obtained.

[0458] 1 H-NMR.δ(CD2Cl2):0.93(s,18H),1.43(s,6H), 1.94(s,6H),2.33(s,6H),2.35-2.40(m,18H),5 .63(s,1H),6.45(s,2H),6.79(s,2H),7.13(d,2 H),7.17-7.18(m,4H),7.20(s,2H),7.34(s,4H) ,8.44(s,2H). [Explanation of symbols]

[0459] 101 first electrode 102 EL layer 103 Second electrode 111 Hole injection layer 112 Hole transport layer 113 Light-emitting layer 114 Electron transport layer 115 Electron injection layer 201 First electrode 202(1) First EL layer 202(2) Second EL layer 202(n-1)th EL layer 202(n) EL layer (n) 204 Second electrode 205 Charge generation layer 205(1) First charge generating layer 205(2) Second charge generating layer 205(n-2) (n-2)th charge generating layer 205(n-1) (n-1)th charge generating layer 301 Element substrate 302 Pixel section 303 Driver circuit section (source line driver circuit) 304a, 304b Drive circuit section (gate line drive circuit) 305 Sealing material 306 Sealing substrate 307 Wiring 308 FPC (Flexible Printed Circuit) 309 FET 310 FET 312 Current control FET 313a, 313b First electrode (anode) 314 Insulators 315 EL layer 316 Second electrode (cathode) 317a, 317b Light-emitting element 318 Space 320a, 320b conductive film 321, 322 area 323 Wiring 324 Colored layer (color filter) 325 Black layer (black matrix) 326, 327, 328 FETs 401 Substrate 402 First electrode 403a, 403b, 403c EL layer 404 Second electrode 405 Light-emitting element 406 Insulating film 407 Bulkhead 500 display device 503 Display section 504 pixels 505 Conductive film 506 position 507 Opening 510 Liquid crystal element 511 Light-emitting element 515 Transistor 516 Transistor 517 Transistor 518 Terminal section 519 Terminal section 521 Circuit Board 522 PCB 523 Light-emitting element 524 Liquid crystal element 525 Insulation Layer 528 Colored layer 529 Adhesive layer 530 Conductive layer 531 EL layer 532 Conductive layer 533 Opening 534 Colored layer 535 Light blocking layer 536 Structure 537 Conductive Layer 538 LCD 539 Conductive Layer 540 Alignment Film 541 Orientation Film 542 Adhesive layer 543 Conductive Layer 544 FPC 545 Connection Layer 546 Insulating Layer 547 Connection 548 Connectors 900 boards 901 First electrode 902 EL layer 903 Second electrode 911 Hole injection layer 912 Hole transport layer 913 Light-emitting layer 914 Electron transport layer 915 Electron injection layer 2000 touch panel 2000' Touch Panel 2501 Display Panel 2502R pixels 2502t transistor 2503c Capacitive element 2503g Scanning line driver circuit 2503t transistor 2509 FPC 2510 board 2511 Wiring 2519 terminal 2521 Insulation layer 2528 Insulator 2550R light emitting element 2560 Sealing layer 2567BM light shielding layer 2567p anti-reflection layer 2567R colored layer 2570 board 2590 board 2591 Electrode 2592 Electrode 2593 Insulation Layer 2594 Wiring 2595 Touch Sensor 2597 Adhesive layer 2598 Wiring 2599 terminals 2601 Pulse voltage output circuit 2602 Current detection circuit 2603 Capacity 2611 Transistor 2612 transistor 2613 Transistor 2621 Electrode 2622 Electrode 3200 board 3201 Cathode 3202 EL layer 3203 Anode 3213 Light-emitting layer 3214 Electron injection layer 3215 Hole transport layer 3216 Hole injection layer 3217 Insulators 3300 Head 3301a Injection part 3301c injection part 3302a Piezoelectric element 3302c Piezoelectric element 3303a Ink 3303c ink 4000 lighting equipment 4001 board 4002 Light-emitting element 4003 board 4004 Electrode 4005 EL layer 4006 Electrode 4007 Electrode 4008 Electrode 4009 Auxiliary wiring 4010 Insulation layer 4011 Sealing substrate 4012 Sealing material 4013 Desiccant 4015 Diffuser 4100 Lighting equipment 4200 Lighting Equipment 4201 Circuit Board 4202 Light-emitting element 4204 Electrode 4205 EL layer 4206 Electrode 4207 Electrode 4208 Electrode 4209 Auxiliary wiring 4210 Insulation layer 4211 Sealing substrate 4212 Sealing material 4213 Barrier film 4214 Planarization film 4215 Diffuser 4300 Lighting Equipment 5101 Light 5102 Wheels 5103 Door 5104 Display section 5105 Handle 5106 Shift lever 5107 Seat 5108 Inner rearview mirror 7100 Television equipment 7101 Housing 7103 Display section 7105 Stand 7107 Display section 7109 Operation key 7110 Remote control device 7201 Main unit 7202 Case 7203 Display section 7204 keyboard 7205 External connection port 7206 Pointing Device 7302 Housing 7304 Display section 7305 Time Icon 7306 Other Icons 7311 Operation button 7312 Operation button 7313 Connection terminal 7321 Band 7322 Clasp 7400 mobile phone 7401 Housing 7402 Display section 7403 Operation buttons 7404 External connection part 7405 Speaker 7406 Microphone 7407 Camera 7500(1), 7500(2) enclosure 7501(1), 7501(2) 1st page 7502(1), 7502(2) 2nd page 8001 Lighting equipment 8002 Lighting equipment 8003 Lighting equipment 9310 Mobile Information Terminal 9311 Display section 9312 Display area 9313 Hinge 9315 chassis

Claims

1. A pair of electrodes; a light-emitting layer and a hole transport layer between the pair of electrodes, the light-emitting layer contains an organometallic complex, The organometallic complex has iridium as a central metal and a ligand, The ligand has a pyrazine skeleton, the nitrogen at position 1 of the pyrazine skeleton is bonded to the iridium; a first phenyl group is bonded to the 2-position of the pyrazine skeleton; a second phenyl group is bonded to the 3-position of the pyrazine skeleton; a third phenyl group is bonded to the 5-position of the pyrazine skeleton; the first phenyl group has an alkyl group as a substituent, the second phenyl group has an alkyl group as a substituent, the third phenyl group has a cyano group as a substituent, The light-emitting element, wherein the hole transport layer contains an aromatic amine compound.

2. A pair of electrodes; a light-emitting layer and a hole transport layer between the pair of electrodes, the light-emitting layer contains an organometallic complex, The organometallic complex has a first ligand and a second ligand that are bonded to iridium, which is a central metal; the first ligand has a pyrazine skeleton, the nitrogen at position 1 of the pyrazine skeleton is bonded to the iridium; a first phenyl group is bonded to the 2-position of the pyrazine skeleton; a second phenyl group is bonded to the 3-position of the pyrazine skeleton; a third phenyl group is bonded to the 5-position of the pyrazine skeleton; the first phenyl group has an alkyl group as a substituent, the second phenyl group has an alkyl group as a substituent, the third phenyl group has a cyano group as a substituent, the second ligand is a monoanionic ligand; The light-emitting element, wherein the hole transport layer contains an aromatic amine compound.

3. In claim 1 or claim 2, The light-emitting device, wherein the third phenyl group further has an alkyl group.

4. In claim 1 or claim 2, The third phenyl group has an alkyl group at least in one of the ortho positions.

5. In any one of claims 1 to 4, the light-emitting layer includes a first organic compound and a second organic compound; The light-emitting element, wherein the first organic compound and the second organic compound are a combination that forms an exciplex.

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