Light-emitting device

Abstract

To provide a novel substance capable of emitting phosphorescence. Or, to provide a novel substance with high luminescence efficiency. To provide a substance. 【Solution means】To provide an organometallic complex having a 4-aryl pyrimidine derivative as a ligand and iridium as a central metal. Specifically, to provide an organometallic complex having a structure represented by the general formula (G1). In the general formula (G1), R represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, R represents hydrogen, 1 a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted phenyl group represents, R 2 represents hydrogen, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and Ar represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms. represents, R 3 represents hydrogen, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and Ar r 1 represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms. JPEG2026048770000162.jpg39169

Description

[Technical Field]

[0001] This relates to organometallic complexes, particularly those capable of converting triplet excited states into luminescence. Furthermore, the present invention relates to a light-emitting device, a light-emitting device, an electronic device, and a lighting device using the organometallic complex. . [Background technology]

[0002] In recent years, there has been a surge in the development of light-emitting devices using luminescent organic and inorganic compounds as light-emitting materials. Yes, in particular, light-emitting elements called EL (Electroluminescence) elements. The structure is simple, consisting only of a light-emitting layer containing a light-emitting material between electrodes, making it thin and lightweight. Due to characteristics such as being able to respond quickly to input signals and being able to be driven by low DC voltage, the next It is attracting attention as a next-generation flat panel display element. Displays using this technology also have the characteristics of superior contrast and image quality, as well as a wide viewing angle. Furthermore, because these light-emitting elements are surface light sources, they are used in the backlight of liquid crystal displays. Applications as a light source for lighting and other applications are also being considered.

[0003] When the light-emitting material is a light-emitting organic compound, the light-emitting mechanism of the light-emitting device is of the carrier-injection type. That is, by placing a light-emitting layer between the electrodes and applying a voltage, the light injected from the electrodes Electrons and holes recombine, causing the light-emitting material to enter an excited state, which then returns to its ground state. It emits light at that time. And, as for the types of excited states, there is the singlet excited state (S * ) and triplet excitation Status (T * ) is possible. Furthermore, the statistical generation ratio in the light-emitting element is S * :T * It is believed that the ratio is 1:3.

[0004] Luminescent organic compounds typically have a singlet ground state. Therefore, the singlet excited state... (S * The emission from ) is called fluorescence because it is an electron transition between the same multiplicity. On the other hand, triple term excited state (T * The light emitted from ) is called phosphorescence because it is an electronic transition between different multiplicities. Here, fluorescent compounds (hereinafter referred to as fluorescent compounds) are typically phosphorus-containing at room temperature. No light is observed, only fluorescence. Therefore, in a light-emitting device using a fluorescent compound... The theoretical limit of the internal quantum efficiency (the ratio of photons generated to injected carriers) is S * :T * The figure of 25% is based on the fact that the ratio is 1:3.

[0005] On the other hand, if phosphorescent compounds are used, the internal quantum efficiency can theoretically reach 100%. Furthermore, it is possible to achieve four times the luminescence efficiency compared to fluorescent compounds. For this reason, high efficiency In order to realize such light-emitting devices, the development of light-emitting devices using phosphorescent compounds has been actively pursued in recent years. In particular, as a phosphorescent compound, iridium and others are used due to their high phosphorescence quantum yield. Organometallic complexes with a central metal are attracting attention, and for example, Patent Document 1 describes iridium... An organometallic complex with a central metal is disclosed as a phosphorescent material.

[0006] One advantage of using highly efficient light-emitting elements is the reduced power consumption of electronic devices using those elements. One example is that it can reduce energy consumption. In these times when energy problems are being discussed, As it is becoming a major factor influencing consumer purchasing trends, it is an extremely important element. It is natural. [Prior art documents] [Patent Documents]

[0007] [Patent Document 1] International Publication No. 00 / 70655 [Overview of the project] [Problems that the invention aims to solve]

[0008] One aspect of the present invention aims to provide a novel material capable of emitting phosphorescence. Alternatively, one of the objectives is to provide a novel material with high luminescence efficiency. One objective is to provide a light-emitting element, light-emitting device, electronic device, or lighting device using [the specified element]. do.

[0009] Alternatively, to provide a light-emitting element, light-emitting device, electronic device, or lighting device with high luminous efficiency. One of its objectives is to provide a highly reliable light-emitting element, light-emitting device, electronic device, or lighting. One of the objectives is to provide a lighting device. Alternatively, a light-emitting element or light-emitting device with low power consumption. One of the objectives is to provide electronic equipment or lighting devices. [Means for solving the problem]

[0010] One aspect of the present invention uses a 4-arylpyrimidine derivative as a ligand and iridium as the central metal. This is an organometallic complex. Another aspect of the present invention is a 4-ally complex having a substituent at the 6-position. Lupyrimidine derivatives (depending on the type of substituent, 6-arylpyrimidine derivatives having a substituent at the 4-position) Organic compounds with a ligand (sometimes called a methyl derivative) and iridium as the central metal. It is a metal complex. Furthermore, one aspect of the present invention has an alkyl or aryl group at the 6-position. A 4-aryl pyrimidine derivative (depending on the type of substituent, it may also be named a 6-aryl pyrimidine derivative having an alkyl group or an aryl group at the 4-position) is used as a ligand, and it is an organometallic complex having iridium as a central metal. In particular, the 4-aryl pyrimidine derivative is preferably a 4,6-diphenyl pyrimidine derivative. and is an organometallic complex having iridium as a central metal. In particular, the 4-aryl pyrimidine derivative is preferably a 4,6-diphenyl pyrimidine derivative. A specific aspect of the present invention is an organometallic complex having a structure represented by the general formula (G1). and is an organometallic complex having iridium as a central metal. In particular, the 4-aryl pyrimidine derivative is preferably a 4,6-diphenyl pyrimidine derivative.

[0011] A specific aspect of the present invention is an organometallic complex having a structure represented by the general formula (G1). and is an organometallic complex having iridium as a central metal. In particular, the 4-aryl pyrimidine derivative is preferably a 4,6-diphenyl pyrimidine derivative.

[0012]

Chemical formula

[0013] In the formula, R 1 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, R represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 2 to 4 carbon atoms, or a substituted or unsubstituted phenyl group, R represents a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 <s000011>[[ID=XXX]] to 4 carbon atoms, and Ar 1 represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms. and Ar

[0014] Another aspect of the present invention is an organometallic complex having a structure represented by the general formula (G2).

[0015]

Chemical formula

[0016] In the formula, R 1 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, R represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, R 2 It should be noted that there seems to be an error in the tag "XXX" in the original text. It should be " 3 " as per the sequence. This might affect the accuracy of the translation if it's not corrected in the original source.This refers to hydrogen, substituted or unsubstituted carbon atoms with 1 carbon atom. R represents an alkyl group of ~4, or a substituted or unsubstituted phenyl group. 3 is hydrogen, or R represents a substituted or unsubstituted alkyl group with 1 to 4 carbon atoms. 4 ~R 7 Each of them operates independently. Hydrogen, substituted or unsubstituted C1-C4 alkyl groups, substituted or unsubstituted C1 ~4 alkoxy groups, substituted or unsubstituted alkylthio groups having 1 to 4 carbon atoms, halogen groups , substituted or unsubstituted C1-C4 haloalkyl groups, or substituted or unsubstituted carbon This represents aryl groups numbered 6 to 10.

[0017] Another aspect of the present invention is an organometallic complex having a structure represented by general formula (G3).

[0018] [ka]

[0019] In the formula, R 2 is hydrogen, substituted or unsubstituted C1-C4 alkyl groups, or substituted or represents an unsubstituted phenyl group, R 3 This is hydrogen, or substituted or unsubstituted carbon atoms with 1 to 4 carbon atoms. R represents an alkyl group. 4 ~R 12 These are, independently, hydrogen, substituted or unsubstituted carbon. Alkyl groups with 1 to 4 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 4 carbon atoms, substituted or This includes unsubstituted alkylthio groups with 1 to 4 carbon atoms, halogen groups, and substituted or unsubstituted groups with 1 carbon atom. This represents a haloalkyl group with 4 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 10 carbon atoms.

[0020] Furthermore, one aspect of the present invention is an organometallic complex represented by the general formula (G4).

[0021] [ka]

[0022] In the formula, L represents a monoanionic ligand. Also, R 1 This refers to substituted or unsubstituted carbon This represents an alkyl group with 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 10 carbon atoms. R 2 This includes hydrogen, substituted or unsubstituted C1-C4 alkyl groups, or substituted or unsubstituted atoms. R represents the phenyl group of substitution, 3 This is hydrogen, or substituted or unsubstituted alkyl groups having 1 to 4 carbon atoms. It represents the Ar group, 1 This represents a substituted or unsubstituted arylene group with 6 to 10 carbon atoms.

[0023] One aspect of the present invention is an organometallic complex represented by the general formula (G5).

[0024] [ka]

[0025] In the formula, L represents a monoanionic ligand. 1 This refers to substituted or unsubstituted carbon atoms with 1 to R represents an alkyl group of 4, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms. 2 teeth , hydrogen, substituted or unsubstituted C1-C4 alkyl groups, or substituted or unsubstituted f Represents an enyl group, R 3 This is hydrogen, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. Represented by R 4 ~R 7 These are, independently, hydrogen, substituted or unsubstituted aluminum atoms with 1 to 4 carbon atoms. Kill group, substituted or unsubstituted alkoxy group having 1 to 4 carbon atoms, substituted or unsubstituted carbon Alkylthio groups with 1 to 4 carbon atoms, halogen groups, substituted or unsubstituted haloal groups with 1 to 4 carbon atoms This represents a kill group, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.

[0026] One aspect of the present invention is an organometallic complex represented by the general formula (G6).

[0027] [ka]

[0028] In the formula, L represents a monoanionic ligand. 2 This is hydrogen, substituted or unsubstituted carbon R represents an alkyl group of type 1 to 4, or a substituted or unsubstituted phenyl group. 3 is hydrogen, also R represents a substituted or unsubstituted alkyl group with 1 to 4 carbon atoms. 4 ~R 12 These are each German In addition, hydrogen, substituted or unsubstituted alkyl groups having 1 to 4 carbon atoms, substituted or unsubstituted carbon Alkoxy groups with 1 to 4 prime atoms, substituted or unsubstituted alkylthio groups with 1 to 4 carbon atoms, halo A gent group, a substituted or unsubstituted C1-C4 haloalkyl group, or a substituted or unsubstituted group. This represents an aryl group with 6 to 10 carbon atoms.

[0029] Furthermore, one aspect of the present invention is an organometallic complex represented by the general formula (G7).

[0030] [ka]

[0031] In the formula, R 1 This is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted alkyl group. R represents an aryl group with 6 to 10 carbon atoms. 2 This refers to hydrogen, substituted or unsubstituted carbon atoms with 1 carbon atom. R represents an alkyl group of ~4, or a substituted or unsubstituted phenyl group. 3 is hydrogen, or This represents a substituted or unsubstituted alkyl group with 1 to 4 carbon atoms, Ar 1 is a substituted or unsubstituted carbon Represents allylene groups numbered 6 to 10.

[0032] One aspect of the present invention is an organometallic complex represented by the general formula (G8).

[0033] [ka]

[0034] In the formula, R 1 This is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted alkyl group. R represents an aryl group with 6 to 10 carbon atoms. 2 This refers to hydrogen, substituted or unsubstituted carbon atoms with 1 carbon atom. R represents an alkyl group of ~4, or a substituted or unsubstituted phenyl group. 3 is hydrogen, or R represents a substituted or unsubstituted alkyl group with 1 to 4 carbon atoms. 4 ~R 7 Each of them operates independently. Hydrogen, substituted or unsubstituted C1-C4 alkyl groups, substituted or unsubstituted C1 ~4 alkoxy groups, substituted or unsubstituted alkylthio groups having 1 to 4 carbon atoms, halogen groups , substituted or unsubstituted C1-C4 haloalkyl groups, or substituted or unsubstituted carbon This represents aryl groups numbered 6 to 10.

[0035] One aspect of the present invention is an organometallic complex represented by the general formula (G9).

[0036] [ka]

[0037] In the formula, R 2 is hydrogen, substituted or unsubstituted C1-C4 alkyl groups, or substituted or represents an unsubstituted phenyl group, R 3 This is hydrogen, or substituted or unsubstituted carbon atoms with 1 to 4 carbon atoms. R represents an alkyl group. 4 ~R 12 These are, independently, hydrogen, substituted or unsubstituted carbon. Alkyl groups with 1 to 4 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 4 carbon atoms, substituted or This includes unsubstituted alkylthio groups with 1 to 4 carbon atoms, halogen groups, and substituted or unsubstituted groups with 1 carbon atom. This represents a haloalkyl group with 4 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 10 carbon atoms.

[0038] Furthermore, in organometallic complexes represented by general formulas (G4) to (G6), monoanionic coordination The child is a monoanionic bidentate chelate ligand with a beta-diketone structure, carboxyl A monoanionic bidentate chelate ligand having a group, a monoanionic ligand having a phenolic hydroxyl group On-positive bidentate chelate ligands, or monoanionic ligands where both coordinating elements are nitrogen. It is preferable that the bidentate chelate ligand is particularly suitable. In particular, a monoa having a beta-diketone structure is preferred. A nionic bidentate chelate ligand is preferred.

[0039] Furthermore, the monoanionic ligand must be one of the general formulas (L1) through (L7). It is preferable.

[0040] [ka]

[0041] In the formula, R 71 ~R 109 These are, independently, hydrogen, substituted or unsubstituted carbon atoms with 1 to 4 carbon atoms. Alkyl groups, halogen groups, vinyl groups, substituted or unsubstituted C1-C4 haloalkyl groups A carbon group, a substituted or unsubstituted alkoxy group having 1 to 4 carbon atoms, or a substituted or unsubstituted carbon group. This represents alkylthio groups with prime numbers from 1 to 4. Also, A 1 ~A 3 These are nitrogen and hydrogen, respectively, independently. sp that binds with 2 sp 2 Represents carbon, and the substituent R is C1-C4 alkyl groups, halogen groups, C1-C4 haloalkyl groups, or phenyl It represents the base.

[0042] Furthermore, one aspect of the present invention is a light-emitting element having the above-mentioned organometallic complex between a pair of electrodes. It is preferable that the above organometallic complex is included in the light-emitting layer.

[0043] Light-emitting devices, electronic devices, and lighting devices using the above-mentioned light-emitting elements are also included in the scope of the present invention. In this specification, the term "light-emitting device" includes an image display device and a light source. , connectors on the panel, for example, FPC (Flexible Printed Circuit) (it) or TAB (Tape Automated Bonding) tape or This is a module to which TCP (Tape Carrier Package) is attached. Modules with a printed circuit board at the end of a TAB tape or TCP, or light-emitting elements with C The OG (Chip On Glass) method directly mounts ICs (integrated circuits). All chures shall also be included in the light-emitting device. [Effects of the Invention]

[0044] According to one aspect of the present invention, a novel material capable of emitting phosphorescence can be provided. Alternatively, a novel material with high luminescence efficiency can be provided. Alternatively, a novel material using the novel material can be provided. We can provide light-emitting elements, light-emitting devices, electronic devices, or lighting devices.

[0045] Alternatively, to provide a light-emitting element, light-emitting device, electronic device, or lighting device with high luminous efficiency. This can be done. Alternatively, a highly reliable light-emitting element, light-emitting device, electronic device, or lighting device can be used. We can provide: or low power consumption light-emitting elements, light-emitting devices, electronic devices, or It can provide lighting devices. [Brief explanation of the drawing]

[0046] [Figure 1] A diagram illustrating a light-emitting element according to one embodiment of the present invention. [Figure 2] A diagram illustrating a passive matrix type light-emitting device. [Figure 3] A diagram illustrating a passive matrix type light-emitting device. [Figure 4] A diagram showing an active-matrix type light-emitting device. [Figure 5] A diagram explaining electronic devices. [Figure 6] A diagram illustrating a lighting device. [Figure 7] A diagram illustrating a lighting device. [Figure 8] 1H NMR chart of the organometallic complex shown in structural formula (100). [Figure 9] UV-Vis absorption spectrum and emission spectrum of the organometallic complex shown in structural formula (100). [Figure 10] 1H NMR chart of the organometallic complex shown in structural formula (140). [Figure 11] UV-Vis absorption spectrum and emission spectrum of the organometallic complex shown in structural formula (140). [Figure 12] 1H NMR chart of the organometallic complex shown in structural formula (152). [Figure 13]UV-Vis absorption spectrum and emission spectrum of the organometallic complex shown in structural formula (152). [Figure 14] A diagram illustrating the light-emitting element of the embodiment. [Figure 15] A diagram showing the current density-luminance characteristics of the light-emitting element 1. [Figure 16] A diagram showing the voltage-luminance characteristics of light-emitting element 1. [Figure 17] A diagram showing the brightness-current efficiency characteristics of the light-emitting element 1. [Figure 18] A figure showing the emission spectrum of light-emitting element 1. [Figure 19] This figure shows the results of the reliability test of light-emitting element 1. [Figure 20] A diagram showing the current density-luminance characteristics of the light-emitting element 2. [Figure 21] A diagram showing the voltage-luminance characteristics of the light-emitting element 2. [Figure 22] A diagram showing the brightness-current efficiency characteristics of the light-emitting element 2. [Figure 23] A diagram showing the emission spectrum of the light-emitting element 2. [Figure 24] This figure shows the results of the reliability test of the light-emitting element 2. [Figure 25] A diagram showing the luminance-external quantum efficiency characteristics of light-emitting element 2. [Figure 26] A diagram showing the current density-luminance characteristics of the light-emitting element 3. [Figure 27] A diagram showing the voltage-luminance characteristics of the light-emitting element 3. [Figure 28] A diagram showing the brightness-current efficiency characteristics of the light-emitting element 3. [Figure 29] A diagram showing the emission spectrum of the light-emitting element 3. [Figure 30] This figure shows the results of the reliability test of the light-emitting element 3. [Figure 31] A diagram showing the luminance-external quantum efficiency characteristics of the light-emitting element 3. [Figure 32] 1H NMR chart of the organometallic complex shown in structural formula (190). [Figure 33] UV-Vis absorption spectrum and emission spectrum of the organometallic complex shown in structural formula (190). [Figure 34]A diagram showing the current density-luminance characteristics of the light-emitting element 4. [Figure 35] A diagram showing the voltage-luminance characteristics of the light-emitting element 4. [Figure 36] A diagram showing the brightness-current efficiency characteristics of the light-emitting element 4. [Figure 37] A diagram showing the emission spectrum of the light-emitting element 4. [Figure 38] A diagram illustrating the light-emitting element of the embodiment. [Figure 39] A diagram showing the voltage-luminance characteristics of the light-emitting element 5. [Figure 40] A diagram showing the brightness-power efficiency characteristics of the light-emitting element 5. [Figure 41] A diagram showing the luminance-external quantum efficiency characteristics of the light-emitting element 5. [Figure 42] A diagram showing the emission spectrum of the light-emitting element 5. [Figure 43] This figure shows the results of the reliability test of the light-emitting element 5. [Figure 44] This figure shows the results of the brightness acceleration test for the light-emitting element 5. [Figure 45] 1H NMR chart of the organometallic complex shown in structural formula (101). [Figure 46] UV-Vis absorption spectrum and emission spectrum of the organometallic complex shown in structural formula (101). [Figure 47] 1H NMR chart of the organometallic complex shown in structural formula (114). [Figure 48] UV-Vis absorption spectrum and emission spectrum of the organometallic complex shown in structural formula (114). [Figure 49] 1H NMR chart of the organometallic complex shown in structural formula (115). [Figure 50] UV-Vis absorption spectrum and emission spectrum of the organometallic complex shown in structural formula (115). [Figure 51] 1H NMR chart of the organometallic complex shown in structural formula (119). [Figure 52] UV-Vis absorption spectrum and emission spectrum of the organometallic complex shown in structural formula (119). [Figure 53]1H NMR chart of the organometallic complex shown in structural formula (123). [Figure 54] UV-Vis absorption spectrum and emission spectrum of the organometallic complex shown in structural formula (123). [Figure 55] 1H NMR chart of the organometallic complex shown in structural formula (134). [Figure 56] UV-Vis absorption spectrum and emission spectrum of the organometallic complex shown in structural formula (134). [Figure 57] 1H NMR chart of the organometallic complex shown in structural formula (178). [Figure 58] UV-Vis absorption spectrum and emission spectrum of the organometallic complex shown in structural formula (178). [Figure 59] 1H NMR chart of the organometallic complex shown in structural formula (194). [Figure 60] UV-Vis absorption spectrum and emission spectrum of the organometallic complex shown in structural formula (194). [Figure 61] 1H NMR chart of the organometallic complex shown in structural formula (195). [Figure 62] UV-Vis absorption spectrum and emission spectrum of the organometallic complex shown in structural formula (195). [Figure 63] 1H NMR chart of the organometallic complex shown in structural formula (196). [Figure 64] UV-Vis absorption spectrum and emission spectrum of the organometallic complex shown in structural formula (196). [Figure 65] 1H NMR chart of the organometallic complex shown in structural formula (199). [Figure 66] UV-Vis absorption spectrum and emission spectrum of the organometallic complex shown in structural formula (199). [Figure 67] 1H NMR chart of the organometallic complex shown in structural formula (200). [Figure 68] UV-Vis absorption spectrum and emission spectrum of the organometallic complex shown in structural formula (200). [Figure 69] 1H NMR chart of the organometallic complex shown in structural formula (201). [Figure 70] The ultraviolet-visible absorption spectrum and emission spectrum of the organometallic complex shown in Structural Formula (201). [Figure 71] A diagram showing the current density-luminance characteristics of the light-emitting device 6. [Figure 72] A diagram showing the voltage-luminance characteristics of the light-emitting device 6. [Figure 73] A diagram showing the luminance-current efficiency characteristics of the light-emitting device 6. [Figure 74] A diagram showing the emission spectrum of the light-emitting device 6. [Figure 75] [[ID=十七]]A diagram showing the results of the reliability test of the light-emitting device 6. [Figure 76] A diagram showing the current density-luminance characteristics of the light-emitting device 7. [Figure 77] A diagram showing the voltage-luminance characteristics of the light-emitting device 7. [Figure 78] A diagram showing the luminance-current efficiency characteristics of the light-emitting device 7. [Figure 79] A diagram showing the emission spectrum of the light-emitting device 7. [Figure 80] A diagram showing the results of the reliability test of the light-emitting device 7. [Figure 81] [[ID=3十五]]A diagram showing the current density-luminance characteristics of the light-emitting device 8. [Figure 82] A diagram showing the voltage-luminance characteristics of the light-emitting device 8. [Figure 83] A diagram showing the luminance-current efficiency characteristics of the light-emitting device 8. [Figure 84] A diagram showing the emission spectrum of the light-emitting device 8. [Figure 85] A diagram showing the luminance-external quantum efficiency characteristics of the light-emitting device 8. [Figure 86] A diagram showing the results of the reliability test of the light-emitting device 8. [Figure 87] A diagram showing the current density-luminance characteristics of the light-emitting device 9. [Figure 88] A diagram showing the voltage-luminance characteristics of the light-emitting device 9. [Figure 89] A diagram showing the luminance-current efficiency characteristics of the light-emitting device 9. [Figure 90] A diagram showing the emission spectrum of the light-emitting device 9. [Figure 91]Figure showing the results of the reliability test of the light-emitting element 9. [Figure 92] Figure showing the current density-luminance characteristics of the light-emitting element 10. [Figure 93] Figure showing the voltage-luminance characteristics of the light-emitting element 10. [Figure 94] Figure showing the luminance-current efficiency characteristics of the light-emitting element 10. [Figure 95] Figure showing the emission spectrum of the light-emitting element 10. [Figure 96] Figure showing the luminance-external quantum efficiency characteristics of the light-emitting element 10. [Figure 97] Figure showing the results of the reliability test of the light-emitting element 10. [Figure 98] Figure showing the current density-luminance characteristics of the light-emitting element 11. [Figure 99] Figure showing the voltage-luminance characteristics of the light-emitting element 11. [Figure 100] Figure showing the luminance-current efficiency characteristics of the light-emitting element 11. [Figure 101] Figure showing the emission spectrum of the light-emitting element 11. [Figure 102] Figure showing the luminance-external quantum efficiency characteristics of the light-emitting element 11. [Figure 103] Figure showing the results of the reliability test of the light-emitting element 11. [Figure 104] Figure showing the current density-luminance characteristics of the light-emitting element 12. [Figure 105] Figure showing the voltage-luminance characteristics of the light-emitting element 12. [Figure 106] Figure showing the luminance-current efficiency characteristics of the light-emitting element 12. [Figure 107] Figure showing the emission spectrum of the light-emitting element 12. [Figure 108] Figure showing the results of the reliability test of the light-emitting element 12. [Figure 109] Figure showing the current density-luminance characteristics of the light-emitting element 13. [Figure 110] Figure showing the voltage-luminance characteristics of the light-emitting element 13. [Figure 111] Figure showing the luminance-current efficiency characteristics of the light-emitting element 13. [Figure 112] Figure showing the emission spectrum of the light-emitting element 13. [Figure 113] Figure showing the luminance-external quantum efficiency characteristics of the light-emitting element 13. [Figure 114] Figure showing the results of the reliability test of the light-emitting element 13. [Figure 115] Figure showing the current density-luminance characteristics of the light-emitting element 14. [Figure 116] Figure showing the voltage-luminance characteristics of the light-emitting element 14. [Figure 117] Figure showing the luminance-current efficiency characteristics of the light-emitting element 14. [Figure 118] Figure showing the emission spectrum of the light-emitting element 14. [Figure 119] Figure showing the results of the reliability test of the light-emitting element 14.

Embodiments for Carrying Out the Invention

[0047] The embodiments will be described in detail with reference to the drawings. However, the present invention is not limited to the following description, and those skilled in the art can easily understand that the form and details can be variously changed without departing from the spirit and scope of the present invention. Therefore, the present invention should not be construed as being limited to the description of the embodiments shown below. In the configuration of the invention described below, the same reference numerals are commonly used for the same parts or parts having the same function in different drawings, and the repeated description thereof will be omitted. and without departing from the spirit and scope of the present invention. Therefore, the present invention should not be construed as being limited to the description of the embodiments shown below. In the configuration of the invention described below, the same reference numerals are commonly used for the same parts or parts having the same function in different drawings, and the repeated description thereof will be omitted. The present invention is not to be construed as being limited to the description of the embodiments shown below. In the configuration of the invention described below, the same reference numerals are commonly used for the same parts or parts having the same function in different drawings, and the repeated description thereof will be omitted. For the same parts or parts having the same function, the same reference numerals are commonly used in different drawings, and the repeated description thereof will be omitted.

[0048] (Embodiment 1) In this embodiment, an organometallic complex according to one aspect of the present invention will be described.

[0049] One aspect of the present invention is an organometallic complex having a 4-aryl pyrimidine derivative as a ligand and iridium as a central metal. In addition, one aspect of the present invention is a 4-aryl pyrimidine derivative having a substituent at the 6-position (depending on the type of the substituent, a 6-aryl pyrimidine having a substituent at the 4-position) Organic compounds with a ligand (sometimes called a methyl derivative) and iridium as the central metal. It is a metal complex. Furthermore, one aspect of the present invention has an alkyl or aryl group at the 6-position. 4-arylpyrimidine derivatives (depending on the type of substituent, an alkyl group or aryl pyrimidine at the 4-position) (Sometimes named as 6-arylpyrimidine derivatives having a reel group) as a ligand It is an organometallic complex with iridium as the central metal. In particular, the 4-arylpyrimidine induce The conductor is preferably a 4,6-diphenylpyrimidine derivative.

[0050] A specific aspect of the present invention is an organometallic complex having a structure represented by general formula (G1). ru.

[0051] [ka]

[0052] In general formula (G1), R 1 This refers to a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted alkyl group. Alternatively, it represents an unsubstituted aryl group with 6 to 10 carbon atoms, R 2 This is hydrogen, substitution, or absence. R represents a substituted alkyl group with 1 to 4 carbon atoms, or a substituted or unsubstituted phenyl group. 3 teeth, This represents hydrogen, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, Ar 1 is, substitute or This represents an unsubstituted arylene group with 6 to 10 carbon atoms.

[0053] Here, Ar 1 Specific examples include a phenylene group and one or more alkyl groups having 1 to 4 carbon atoms. A substituted phenylene group, a phenylene group substituted with one or more alkoxy groups having 1 to 4 carbon atoms, Phenylene group substituted with one or more alkylthio groups having 1 to 4 carbon atoms, and ali groups having 6 to 10 carbon atoms. Phenylene groups substituted with one or more halogen groups, phenylene groups substituted with one or more halogen groups, Phenylene group substituted with one or more C1-C4 haloalkyl groups, substituted or unsubstituted Examples include biphenyl-diyl groups and substituted or unsubstituted naphthalene-diyl groups.

[0054] Also, R 1 ~R 3 Specific examples of alkyl groups with 1 to 4 carbon atoms include methyl groups and ethyl groups. propyl group, isopropyl group, butyl group, sec-butyl group, isobutyl group, te Examples include the rt-butyl group, and specific examples of aryl groups with 6 to 10 carbon atoms include phenyl A phenyl group substituted with one or more C1-C4 alkyl groups, an alkoxy group Phenyl groups substituted with one or more thio groups, and alkylthio groups having 1 to 4 carbon atoms substituted with one or more thio groups Phenyl groups, phenyl groups substituted with one or more aryl groups having 6 to 10 carbon atoms, halogen groups Phenyl groups with one or more substitutions, phenyl groups with one or more substitutions of a C1-C4 haloalkyl group Examples include the yl group and the naphthalene-yl group.

[0055] Also, R 1 In this context, alkyl groups with 1 to 4 carbon atoms are preferred over alkyl groups with 2 or more carbon atoms. It is preferable. Alkyl groups with two or more carbon atoms suppress intermolecular interactions due to steric hindrance. Therefore, side reactions in the synthesis reaction of organometallic complexes, which is one aspect of the present invention, are suppressed, and yield The rate will improve.

[0056] Considering this, R 1 Examples of C1-C4 alkyl groups in this context include ethyl group, propionate group. butyl group, isopropyl group, butyl group, sec-butyl group, isobutyl group, tert-butyl group The base is preferable.

[0057] The above Ar 1 If the group is substituted or unsubstituted, synthesis becomes easier, which is preferable. Therefore, one aspect of the present invention relates to an organometallic complex having a structure represented by general formula (G2). That is the case.

[0058] [ka]

[0059] In general formula (G2), R 1 This refers to a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted alkyl group. Alternatively, it represents an unsubstituted aryl group with 6 to 10 carbon atoms, R 2 This is hydrogen, substitution, or absence. R represents a substituted alkyl group with 1 to 4 carbon atoms, or a substituted or unsubstituted phenyl group. 3 teeth, R represents hydrogen, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. 4 ~R 7 That Each independently consists of hydrogen, a substituted or unsubstituted C1-C4 alkyl group, and a substituted or unsubstituted alkyl group. Substituted C1-C4 alkoxy groups, substituted or unsubstituted C1-C4 alkylthio groups , halogen group, substituted or unsubstituted C1-C4 haloalkyl group, or substituted or This represents an unsubstituted aryl group with 6 to 10 carbon atoms.

[0060] Here, R 1 ~R 3 A concrete example of this is the same as the general formula (G1). , R 4 ~R 7 Specific examples include, independently, hydrogen, methyl group, ethyl group, and propyl. group, isopropyl group, butyl group, sec-butyl group, isobutyl group, tert-butyl group Methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, sec- Toxy group, isobutoxy group, tert-butoxy group, methylsulfinyl group, ethyl sulf Finyl group, propyl sulfinyl group, isopropyl sulfinyl group, butyl sulfinyl Isobutylsulfinyl group, isobutylsulfinyl group, sec-butylsulfinyl group, tert-butylsulfinyl group Rufinyl group, fluoro group, fluoromethyl group, difluoromethyl group, trifluoromethyl chloromethyl group, chloromethyl group, dichloromethyl group, trichloromethyl group, bromomethyl group, 2, 2,2-trifluoroethyl group, 3,3,3-trifluoropropyl group, 1,1,1,3 ,3,3-hexafluoroisopropyl group, phenyl group, C1-C4 alkyl group Phenyl groups substituted in the above manner, phenyl groups substituted with one or more alkoxy groups having 1 to 4 carbon atoms. , a phenyl group substituted with one or more alkylthio groups having 1 to 4 carbon atoms, and an aryl thio group having 6 to 10 carbon atoms. Phenyl groups substituted with one or more halogen groups, phenyl groups substituted with one or more halogen groups, carbon Phenyl groups substituted with one or more haloalkyl groups of 1 to 4, or substituted or unsubstituted naphtha Examples include lenyl groups.

[0061] In one aspect of the present invention, a 4,6-diphenylpyrimidine derivative is preferably used as a ligand, It is an organometallic complex with iridium as the central metal. Specifically, it is represented by the general formula (G3). It is an organometallic complex having a structure like the one shown by the general formula (G3). The R has a phenyl group at the 6th position of the skeleton (that is, the above R 1 is a substituted or unsubstituted phenyl group (This is preferable because it improves the yield of the organometallic complex.) Therefore, it is preferable because it exhibits extremely high luminescence efficiency.

[0062] [ka]

[0063] In general formula (G3), R 2 This includes hydrogen, substituted or unsubstituted alkyl groups having 1 to 4 carbon atoms, R represents a substituted or unsubstituted phenyl group. 3 This is hydrogen, or substituted or unsubstituted carbon Represents an alkyl group with prime numbers 1 to 4, R 4 ~R 12 These are, independently, hydrogen, substitution or Unsubstituted C1-C4 alkyl groups, substituted or unsubstituted C1-C4 alkoxy groups substituted or unsubstituted C1-C4 alkylthio groups, halogen groups, substituted or unsubstituted Substituted C1-C4 haloalkyl groups, or substituted or unsubstituted C6-C10 haloalkyl groups It represents the 'L' group.

[0064] Here, R 2 ~R 7 Specific examples include those similar to the general formulas (G1) and (G2). It can be done. Also, R 8 ~R 12 Specific examples include hydrogen, methyl group, and ethyl group, each independently. propyl group, isopropyl group, butyl group, sec-butyl group, isobutyl group, te rt-butyl group, methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, sec-butoxy group, isobutoxy group, tert-butoxy group, methylsulfinyl Group, ethyl sulfinyl group, propyl sulfinyl group, isopropyl sulfinyl group, b Chil sulfinyl group, isobutyl sulfinyl group, sec-butyl sulfinyl group, te rt-butylsulfinyl group, fluoro group, fluoromethyl group, difluoromethyl group, Lifluoromethyl group, chloromethyl group, dichloromethyl group, trichloromethyl group, bromo Methyl group, 2,2,2-trifluoroethyl group, 3,3,3-trifluoropropyl group, 1,1,1,3,3,3-Hexafluoroisopropyl group, phenyl group, C1-C4 Phenyl groups substituted with one or more alkyl groups, and alkoxy groups having 1 to 4 carbon atoms substituted with one or more alkyl groups A phenyl group, a phenyl group substituted with one or more alkylthio groups having 1 to 4 carbon atoms, Phenyl groups substituted with one or more aryl groups from 6 to 10, and halogen groups substituted with one or more halogen groups. Phenyl group, phenyl group substituted with one or more C1-C4 haloalkyl groups, substituted or Examples include unsubstituted naphthaleneyl groups.

[0065] Furthermore, one aspect of the present invention is an organometallic complex represented by the general formula (G4).

[0066] [ka]

[0067] In the general formula (G4), L represents a monoanionic ligand. Also, R 1 is a substitution or Unsubstituted C1-C4 alkyl groups, or substituted or unsubstituted C6-C10 alkyl groups R represents a group 2 This includes hydrogen, substituted or unsubstituted C1-C4 alkyl groups, or substituted Alternatively, it represents an unsubstituted phenyl group, R 3 This is hydrogen, or a substituted or unsubstituted carbon-1 atom. ~4 represents an alkyl group, Ar 1represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms. Note that Ar 1 and R 1 ~R 3 are the same as in the general formula (G1).

[0068] When the above Ar 1 is a phenylene group, the synthesis becomes easy, which is preferable. Therefore, one aspect of the present invention is an organometallic complex represented by the general formula (G5).

[0069]

Chemical formula

[0070] In the general formula (G5), L represents a monoanionic ligand. R 1 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms. R 2 represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted phenyl group. R 3 represents hydrogen, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. R 4 ~R 7 each independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 4 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, a halogen group, a substituted or unsubstituted haloalkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms. Note that R 1 ~R 7 are the same as in the general formula (G2). <00011�6>

[0071] Also, one aspect of the present invention is an organometallic complex represented by the general formula (G6). General formula (G6 ) like the structure represented by, when having a phenyl group at the 6-position of the pyrimidine skeleton, it is preferable because the yield of the organometallic complex is improved.

[0072] [Chemical formula]

[0073] In general formula (G6), L represents a monoanionic ligand. R 2 represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted phenyl group, and R 3 represents hydrogen, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and R 4 ~R 12 are , each independently, hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 4 carbon atoms, a substituted or unsubstituted alkyl thio group, a halogen group, a substituted or unsubstituted haloalkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms. Note that the specific examples of R 2 ~R 12 are the same as those of general formula (G3).

[0074] Also, one aspect of the present invention is an organometallic complex represented by general formula (G7).

[0075] [Chemical formula]

[0076] In general formula (G7), R 1 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and R 2 represents hydrogen, a substituted or unsubstituted R represents a substituted alkyl group with 1 to 4 carbon atoms, or a substituted or unsubstituted phenyl group. 3 teeth, This represents hydrogen, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, Ar 1 is, substitute or This represents an unsubstituted arylene group with 6 to 10 carbon atoms. 1 and R 1 ~R 3 Specific examples are This is the same as the general formula (G1).

[0077] The above Ar 1 If the group is a phenylene group, the synthesis becomes easier, and therefore it is preferable. One aspect of the invention is an organometallic complex represented by the general formula (G8).

[0078] [ka]

[0079] In general formula (G8), R 1 This refers to a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted alkyl group. Alternatively, it represents an unsubstituted aryl group with 6 to 10 carbon atoms, R 2 This is hydrogen, substitution, or absence. R represents a substituted alkyl group with 1 to 4 carbon atoms, or a substituted or unsubstituted phenyl group. 3 teeth, R represents hydrogen, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. 4 ~R 7 That Each independently consists of hydrogen, a substituted or unsubstituted C1-C4 alkyl group, and a substituted or unsubstituted alkyl group. Substituted C1-C4 alkoxy groups, substituted or unsubstituted C1-C4 alkylthio groups , halogen group, substituted or unsubstituted C1-C4 haloalkyl group, or substituted or This represents an unsubstituted aryl group with 6 to 10 carbon atoms. 1 ~R 7A concrete example is the general formula (G This is the same as in (2).

[0080] Furthermore, one aspect of the present invention is an organometallic complex represented by the general formula (G9). As shown in the structure represented by ), when a phenyl group is located at the 6th position of the pyrimidine skeleton, an organometallic complex is formed. This is preferable because it improves the yield of the body.

[0081] [ka]

[0082] In general formula (G9), R 2 This includes hydrogen, substituted or unsubstituted alkyl groups having 1 to 4 carbon atoms, R represents a substituted or unsubstituted phenyl group. 3 This is hydrogen, or substituted or unsubstituted carbon Represents an alkyl group with prime numbers 1 to 4, R 4 ~R 12 These are, independently, hydrogen, substitution or Unsubstituted C1-C4 alkyl groups, substituted or unsubstituted C1-C4 alkoxy groups substituted or unsubstituted C1-C4 alkylthio groups, halogen groups, substituted or unsubstituted Substituted C1-C4 haloalkyl groups, or substituted or unsubstituted C6-C10 haloalkyl groups It represents the R group. 2 ~R 12 The specific example is the same as in the general formula (G3).

[0083] In organometallic complexes represented by general formulas (G4) to (G6), the monoanionic ligand is: A monoanionic bidentate chelate ligand having a beta-diketone structure, possessing a carboxyl group. A monoanionic bidentate chelate ligand, a monoanionic having a phenolic hydroxyl group A bidentate chelate ligand, or a monoanionic bidentate where both coordinating elements are nitrogen. It is preferable that it be a chelate ligand. In particular, a monoanion having a beta-diketone structure. It is preferable that it is a bidentate chelate ligand. Having a beta-diketone structure is preferable. The increased solubility of the metallochemical complex in organic solvents facilitates purification, which is preferable. Having a ketone structure is preferable because it allows for the creation of organometallic complexes with high luminescence efficiency. Furthermore, having a beta-diketone structure enhances sublimation properties and results in excellent vapor deposition performance. There are advantages.

[0084] Furthermore, in organometallic complexes represented by general formulas (G4) to (G6), monoanionic coordination The child is preferably one of the general formulas (L1) to (L7).

[0085] [ka]

[0086] In general formulas (L1) to (L7), R 71 ~R 109 Each of them independently involves hydrogen, substitution, or This includes unsubstituted C1-C4 alkyl groups, halogen groups, vinyl groups, and substituted or unsubstituted carbon groups. A haloalkyl group with 1 to 4 prime atoms, a substituted or unsubstituted alkoxy group with 1 to 4 carbon atoms, or This represents a substituted or unsubstituted alkylthio group with 1 to 4 carbon atoms. Also, A 1 ~A 3 That Each independently bonds with nitrogen and hydrogen, forming sp² molecules. 2 sp 2 carbon The substituent R is an alkyl group having 1 to 4 carbon atoms, a halogen group, or a haloalkyl group having 1 to 4 carbon atoms. It represents a phenyl group or a phenyl group.

[0087] ≪Method for synthesizing 4-arylpyrimidine derivatives represented by general formula (G0)≫ An example of a synthesis method for 4-arylpyrimidine derivatives represented by the following general formula (G0): Let me explain. The 4-arylpyrimidine derivative represented by the following general formula (G0) is as follows: It can be synthesized using the simple synthesis schemes (a), (a'), or (a”).

[0088] [ka]

[0089] In the general formula (G0), R 1 This includes substituted or unsubstituted alkyl groups having 1 to 4 carbon atoms, R represents a substituted or unsubstituted aryl group with 6 to 10 carbon atoms. 2 is hydrogen, substitution or R represents an unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted phenyl group. 3 represents hydrogen, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, Ar 2 is, place This represents a substituted or unsubstituted aryl group with 6 to 10 carbon atoms.

[0090] For example, a 4-arylpyrimidine derivative represented by general formula (G0) can be synthesized using the synthesis scheme (a As shown in (), arylboronic acid (A1) and halogenated pyrimidine compound (A2) It is obtained by coupling.

[0091] [ka]

[0092] In synthesis scheme (a), X represents a halogen, and R 1 This refers to substituted or unsubstituted carbon This represents an alkyl group with 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 10 carbon atoms. R 2 This includes hydrogen, substituted or unsubstituted C1-C4 alkyl groups, or substituted or unsubstituted atoms. R represents the phenyl group of substitution, 3 This is hydrogen, or substituted or unsubstituted alkyl groups having 1 to 4 carbon atoms. It represents the Ar group, 2 This represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.

[0093] Furthermore, the 4-arylpyrimidine derivative represented by the general formula (G0) is synthesized using the synthesis scheme (a' As shown in (A1'), the aryl lithium compound or Grignard reagent shown in (A1') is used as a pyropropyl alcohol. It is obtained by reacting it with a methyl compound (A2').

[0094] [ka]

[0095] In the synthesis scheme (a'), X represents a halogen, and R 1 is either substituted or non-substituted. Alkyl groups with 1 to 4 carbon atoms, or substituted or unsubstituted aryl groups with 6 to 10 carbon atoms. And, R 2 This includes hydrogen, substituted or unsubstituted C1-C4 alkyl groups, or substituted or R represents an unsubstituted phenyl group. 3 This is hydrogen, or substituted or unsubstituted carbon atoms with 1 to 4 carbon atoms. It represents the lukyl group, Ar 2 This represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.

[0096] Furthermore, the 4-arylpyrimidine derivative represented by the general formula (G0) is synthesized using the synthesis scheme (a' As shown in '), the aryl 1,3-diketone (A1'') and amidine (A2'') It is obtained by reaction.

[0097] [ka]

[0098] In addition, in the general formula (G0), R 3 In the case of hydrogen, Non-Patent Literature (H. Bredere) ck, R. Gompper, G. Morlock, “Chemische Berich As shown in te, 90, 942 (1957), the aryl 1,3-diketone ( It is obtained by heating and reacting A1'' with formamide in the presence of an acid catalyst.

[0099] In the synthesis scheme (a''), R 1 These are substituted or unsubstituted alkyl groups with 1 to 4 carbon atoms. R represents an aryl group, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms. 2 is hydrogen, place A substituted or unsubstituted C1-C4 alkyl group, or a substituted or unsubstituted phenyl group Represented by R 3 represents hydrogen, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, Ar 2 This represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.

[0100] The above-mentioned compounds (A1), (A2), (A1'), (A2'), (A1''), (A2'' Since various types are commercially available or can be synthesized, they are expressed by the general formula (G0). Numerous types of 4-arylpyrimidine derivatives can be synthesized. Therefore, an organometallic complex according to one aspect of the present invention has a rich variety of ligands. It has that characteristic.

[0101] ≪Method for synthesizing organometallic complexes according to one embodiment of the present invention, represented by general formulas (G4) and (G7)≫ Next, the 4-arylpyrimidine derivative represented by the general formula (G0) is orthometalated to form Among the organometallic complexes of one aspect of the present invention, a preferred specific example is the following general formula (G The synthesis methods for organometallic complexes represented by 4) and (G7) will be described below.

[0102] [ka]

[0103] In general formulas (G4) and (G7), L represents a monoanionic ligand, and R 1 teeth, Substituted or unsubstituted alkyl groups with 1 to 4 carbon atoms, or substituted or unsubstituted alkyl groups with 6 carbon atoms Represents 10 aryl groups, R 2 This includes hydrogen, substituted or unsubstituted alkyl groups having 1 to 4 carbon atoms. R represents a group, or a substituted or unsubstituted phenyl group. 3 is hydrogen, or substituted or absent. The character represents an alkyl group with 1 to 4 carbon atoms, Ar 1 This is a substituted or unsubstituted carbon atom with 6 to 10 carbon atoms. This represents the leylene group.

[0104] <Method for synthesizing an organometallic complex according to one embodiment of the present invention, represented by general formula (G4)> First, as shown in the synthesis scheme (b) below, 4-aryl py(G0) represented by the general formula (G0) is used. Limidine derivatives and iridium halide compounds (iridium chloride, iridium bromide, yo Iridium chloride (preferably iridium trichloride hydrate) is used in a solvent-free, alcohol-based solution. Solvents (glycerol, ethylene glycol, 2-methoxyethanol, 2-ethoxyethanol) Using an alcohol-based solvent (such as ol) alone, or a mixed solvent of one or more alcohol-based solvents and water, By heating in a gas atmosphere, organometallic complexes having a halogen-bridged structure are produced. It is possible to obtain a novel binuclear complex (B) of a single type. The heating method is not particularly limited. There is no set rule; an oil bath, sand bath, or aluminum block may be used. Also, a microphone It is also possible to use radio waves as a heating method.

[0105] [ka]

[0106] In synthesis scheme (b), X represents a halogen, and R 1 This refers to substituted or unsubstituted carbon This represents an alkyl group with 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 10 carbon atoms. R 2 This includes hydrogen, substituted or unsubstituted C1-C4 alkyl groups, or substituted or unsubstituted atoms. R represents the phenyl group of substitution, 3 This is hydrogen, or substituted or unsubstituted alkyl groups having 1 to 4 carbon atoms. It represents the Ar group. 1 This represents a substituted or unsubstituted arylene group with 6 to 10 carbon atoms. Ar 2 This represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.

[0107] Furthermore, as shown in the synthesis scheme (c) below, the composite obtained in the synthesis scheme (b) described above can be obtained The nuclear complex (B) and the monoanionic ligand starting material HL were reacted in an inert gas atmosphere. By doing so, the proton of HL is removed and L coordinates to the central metal Ir, and the general formula (G4) An organometallic complex according to one aspect of the present invention is obtained. The heating means is not particularly limited. Alternatively, an oil bath, sand bath, or aluminum block may be used. Microwaves may also be used. It can also be used as a heating method.

[0108] [ka]

[0109] In synthesis scheme (c), L represents a monoanionic ligand and X represents a halogen. And, R 1 This is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted alkyl group. R represents an aryl group with 6 to 10 carbon atoms. 2 This refers to hydrogen, substituted or unsubstituted carbon atoms with 1 or more carbon atoms. 4 represents an alkyl group, or a substituted or unsubstituted phenyl group, R 3 is hydrogen, or substitution Alternatively, it represents an unsubstituted alkyl group with 1 to 4 carbon atoms, Ar 1 This refers to the number of substituted or unsubstituted carbon atoms. Represents 6 to 10 arylene groups.

[0110] In the present invention, as described above, an ortho is used as a ligand for a 4-arylpyrimidine derivative. To obtain the metal complex, the 6th position of the pyrimidine (i.e., R) 1 A substituent has been introduced to it. Especially R 1 For example, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted alkyl group. A substituted aryl group with 6 to 10 carbon atoms is used. Therefore, R 1 A field using hydrogen Compared to the combined form, the halogen-bridged dinuclear metal complex produced in synthesis scheme (b) This suppresses the decomposition of the compound during the reaction represented by the synthesis scheme (c), resulting in a dramatically higher yield. You can obtain a rate.

[0111] Furthermore, the monoanionic ligand L in general formula (G4) has a beta-diketone structure. A monoanionic bidentate chelate ligand, a monoanionic bidentate having a carboxyl group Bidentate chelate ligands, monoanionic bidentate chelate ligands having phenolic hydroxyl groups, Alternatively, it is a monoanionic bidentate chelate ligand in which both coordinating elements are nitrogen. This is preferable. In particular, a monoanionic bidentate chelate ligand having a beta-diketone structure. Therefore, having a beta-diketone structure results in high solubility of organometallic complexes in organic solvents. Furthermore, purification becomes easier, which is preferable. Also, having a beta-diketone structure improves luminescence efficiency. It is preferable because it can yield organometallic complexes with high efficacy. Also, it has a beta-diketone structure. This process enhances sublimation and offers the advantage of superior vapor deposition performance.

[0112] Furthermore, the monoanionic ligand must be one of the general formulas (L1) through (L7). These ligands are preferable because they have high coordinating ability and can be obtained at low cost. It is effective.

[0113] [ka]

[0114] In general formulas (L1) to (L7), R 71 ~R 109 Each of them independently involves hydrogen, substitution, or This includes unsubstituted C1-C4 alkyl groups, halogen groups, vinyl groups, and substituted or unsubstituted carbon groups. A haloalkyl group with 1 to 4 prime atoms, a substituted or unsubstituted alkoxy group with 1 to 4 carbon atoms, or This represents a substituted or unsubstituted alkylthio group with 1 to 4 carbon atoms. Also, A 1 ~A 3 That Each independently bonds with nitrogen and hydrogen, forming sp² molecules. 2 sp 2 carbon The substituent R is an alkyl group having 1 to 4 carbon atoms, a halogen group, or a haloalkyl group having 1 to 4 carbon atoms. It represents a phenyl group or a phenyl group.

[0115] <Method for synthesizing an organometallic complex according to one embodiment of the present invention, represented by general formula (G7)> An organometallic complex, which is one embodiment of the present invention represented by the general formula (G7), is synthesized using the following synthesis scheme (d It can be synthesized by the following: 4-arylpyrial, represented by the general formula (G0). Midine derivatives and iridium halide compounds (iridium chloride, iridium bromide, iodine iridium chloride (preferably iridium trichloride hydrate) or iridium organometallic complex After mixing with the compound (acetylacetonate complex, diethyl sulfide complex, etc.), heat By doing so, an organometallic complex having a structure represented by general formula (G7) can be obtained. Furthermore, this heating process is a 4-arylpyrimidine derivative represented by the general formula (G0). The body and an iridium halide compound or an iridium organometallic complex compound are mixed into an alcohol Solvent system (glycerol, ethylene glycol, 2-methoxyethanol, 2-ethoxyethanol) This may be done after dissolving in (e.g., tanol). There are no particular limitations on the heating method, such as an oil bath. A sand bath or aluminum block may be used as a heating element. It is also possible to use it.

[0116] [ka]

[0117] In synthesis scheme (d), R 1 These are substituted or unsubstituted alkyl groups with 1 to 4 carbon atoms. , or represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, R 2 This includes hydrogen, substitution as well. This refers to an unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted phenyl group. , R 3 A represents hydrogen, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. r 1 represents a substituted or unsubstituted arylene group with 6 to 10 carbon atoms, and Ar 2 is a substitution or no substitution This represents a substituted aryl group with 6 to 10 carbon atoms.

[0118] In the present invention, as described above, an ortho is used as a ligand for a 4-arylpyrimidine derivative. To obtain the metal complex, the 6th position of the pyrimidine (i.e., R) 1 A substituent has been introduced to it. Especially R 1 For example, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted alkyl group. A substituted aryl group with 6 to 10 carbon atoms is used. Therefore, R 1 A field using hydrogen Compared to the combined method, the yield in synthesis scheme (d) can be increased.

[0119] The above describes one example of a synthesis method, but the organometallic complex is one aspect of the present invention that is disclosed. It may be synthesized by any other synthesis method.

[0120] The following structural formulas (100) to (201) are specific structural formulas of organometallic complexes according to one embodiment of the present invention. The following are listed. However, the present invention is not limited to these.

[0121] [ka]

[0122] [ka]

[0123]

change

[0124]

change

[0125]

change

[0126]

change

[0127]

change

[0128]

change

[0129]

change

[0130]

change

[0131]

change

[0132]

change

[0133]

change

[0134] [ka]

[0135] [ka]

[0136] [ka]

[0137] [ka]

[0138] [ka]

[0139] Furthermore, the organometallic complexes represented by the above structural formulas (100) to (201) have different types of ligands. Therefore, stereoisomers may exist, but organometallic complexes in one aspect of the present invention do not have these isomers. This includes everything.

[0140] The organometallic complex described above, according to one aspect of the present invention, is capable of emitting phosphorescence and is red. Because it has a broad emission spectrum from the green wavelength range, it is used as a light-emitting material and light-emitting element. It can be used as such.

[0141] By using an organometallic complex according to one aspect of the present invention, a light-emitting element with high luminescence efficiency, a light-emitting device, and an electric light can be produced. Sub-devices or lighting devices can be realized. Alternatively, light-emitting elements or light-emitting devices with low power consumption can be realized. This allows for the realization of devices, electronic equipment, or lighting devices.

[0142] Furthermore, by using an organometallic complex according to one aspect of the present invention, a highly reliable light-emitting element and light-emitting device can be obtained. This allows for the realization of electronic devices or lighting devices.

[0143] In this embodiment, the configurations shown in other embodiments can be used in appropriate combination. can.

[0144] (Embodiment 2) In this embodiment, as one aspect of the present invention, the organometallic complex described in Embodiment 1 is used to emit light. The light-emitting element used in the layer will be explained using Figure 1(A).

[0145] Figure 1(A) shows a light-emitting device having an EL layer 102 between the first electrode 101 and the second electrode 103. This is a diagram showing the element. The EL layer 102 includes the light-emitting layer 113. The light-emitting layer 113 is an embodiment This invention includes an organometallic complex according to one embodiment of the present invention described in Embodiment 1.

[0146] By applying a voltage to such a light-emitting element, injection can be performed from the first electrode 101 side. The holes that are generated and the electrons injected from the second electrode 103 side are then re-energized in the light-emitting layer 113. It binds and excites the organometallic complex. Then, the excited organometallic complex returns to the ground state. It emits light when it returns. Thus, an organometallic complex, which is one aspect of the present invention, is used in a light-emitting element. It functions as a light-emitting material. In the light-emitting element shown in this embodiment, the first electrode 1 Electrode 01 functions as the anode, and the second electrode 103 functions as the cathode.

[0147] The first electrode 101, which functions as an anode, has a large work function (specifically, 4.0 eV or more). (Above) It is preferable to use metals, alloys, electrically conductive compounds, and mixtures thereof. Specifically, for example, indium tin oxide (ITO) Indium oxide containing silicon or silicon oxide, tin oxide, indium oxide - Zinc oxide, tungsten oxide and zinc oxide Examples include indium oxide and other materials. Other materials include gold, platinum, nickel, tungsten, Chromium, molybdenum, iron, cobalt, copper, palladium, titanium, etc. can be used.

[0148] However, of the EL layer 102, the layer formed in contact with the first electrode 101 is organically formed as described later. When formed using a composite material obtained by mixing a compound and an electron acceptor. The material used for the first electrode 101 can be various metals, alloys, etc., regardless of the magnitude of the work function. Electrically conductive compounds and mixtures thereof can be used. For example, aluminum Alloys containing aluminum, silver, and aluminum (for example, Al-Si) can also be used.

[0149] The first electrode 101 is shaped by, for example, sputtering or deposition (including vacuum deposition). It is possible.

[0150] The EL layer 102 formed on the first electrode 101 has at least an emissive layer 113. Furthermore, it is formed by including an organometallic complex, which is one aspect of the present invention. Known substances can be used, and either low-molecular-weight compounds or high-molecular-weight compounds can be used. It is also possible to do so. Furthermore, the material forming the EL layer 102 consists solely of organic compounds. Furthermore, this also includes compositions that partially contain inorganic compounds.

[0151] The EL layer 102, in addition to the light-emitting layer 113, contains a material with high hole injection potential, as shown in Figure 1(A). A hole injection layer 111, a hole transport layer 112 containing a material with high hole transport properties, and electron An electron transport layer 114 containing a material with high transportability, an electron transport layer containing a material with high electron injectionability It is formed by appropriately combining and stacking sub-injection layers 115 and the like.

[0152] The hole injection layer 111 is a layer containing a material with high hole injection potential. For example, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium Chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver Metal oxides such as oxides, tungsten oxide, and manganese oxide can be used. Also, phthalocyanine (abbreviation: H2Pc), copper(II) phthalocyanine (abbreviation: CuPc) Phthalocyanine compounds such as the above can be used.

[0153] Furthermore, the low molecular weight organic compound 4,4',4''-tris(N,N-diphenylamino ) Triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylamine) [Tylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4 ,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphen Lu (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)- N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTP) D) 1,3,5-Tris[N-(4-diphenylaminophenyl)-N-phenylamine [N]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl) )-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3, 6-Bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9- Phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-( 9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: P Aromatic amine compounds such as CzPCN1 can be used.

[0154] Furthermore, polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used. For example, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyl truffle) Phenylamine (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenyl [phenylamino]phenyl-N'-phenylamino}phenyl)methacrylamide] (Abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bi Examples of high-molecular-weight compounds include poly(phenyl)benzidine (abbreviated as Poly-TPD). Also, poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), Polyaniline / Poly(styrene sulfonate) (PAni / PS Polymer compounds to which acids such as S) have been added can be used.

[0155] Furthermore, as the hole injection layer 111, an organic compound and an electron acceptor are mixed. A composite material may be used. Such a composite material can be used to transform an organic compound through electron acceptors. Because holes are generated, it exhibits excellent hole injection and hole transport properties. In this case, the organic compound and Therefore, it is preferable that the material is excellent at transporting the generated holes (a substance with high hole transport properties). stomach.

[0156] Organic compounds used in composite materials include aromatic amine compounds, carbazole derivatives, and fragrances. Various compounds such as hydrocarbons and polymers (oligomers, dendrimers, polymers, etc.) Materials can be used. Furthermore, as organic compounds used in composite materials, high hole transport properties are preferred. It is preferable that it be an organic compound. Specifically, 10 -6 cm 2 Hole movement of / Vs or greater It is preferable that the material has a degree of [unclear]. However, it is not necessarily a material that has higher hole transport than electron transport. However, other materials may also be used. Below, we will discuss organic compounds that can be used in composite materials. List the specific ingredients.

[0157] Examples of organic compounds that can be used in composite materials include TDATA and MTDATA. , DPAB, DNTPD, DPA3B, PCzPCA1, PCzPCA2, PCzPCN 1,4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl ru-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl- 4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP) Aromatic amine compounds such as ) and 4,4'-di(N-carbazolyl)biphenyl (abbreviation: C BP), 1,3,5-Tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: T CPB), 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene ( Abbreviation: CzPA), 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl [Nyl]-9H-carbazole (abbreviation: PCzPA), 1,4-bis[4-(N-carbazole Carbazole derivatives such as lyl(phenyl)phenyl]-2,3,5,6-tetraphenylbenzene It can be used.

[0158] Also, 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t- BuDNA), 2-tert-butyl-9,10-di(1-naphthyl)anthracene, 9 ,10-Bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 2-t ert-butyl-9,10-bis(4-phenylphenyl)anthracene (abbreviation: tB) uDBA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 9,10- Diphenylanthracene (abbreviation: DPAnth), 2-tert-butylanthracene ( Abbreviation: t-BuAnth), 9,10-bis(4-methyl-1-naphthyl)anthracene (Abbreviation: DMNA), 9,10-bis[2-(1-naphthyl)phenyl]-2-tert -butylanthracene, 9,10-bis[2-(1-naphthyl)phenyl]anthracene , 2,3,6,7-tetramethyl-9,10-di(1-naphthyl)anthracene, etc. Hydrocarbon compounds can be used.

[0159] Furthermore, 2,3,6,7-tetramethyl-9,10-di(2-naphthyl)anthracene, 9,9'-biantryl,10,10'-diphenyl-9,9'-biantryl,10, 10'-Bis(2-phenylphenyl)-9,9'-biantryl, 10,10'-bis [(2,3,4,5,6-pentaphenyl)phenyl]-9,9'-biantryl, an Tracene, Tetracene, Rubren, Perylene, 2,5,8,11-Tetra(tert-br Chil) Perylene, Pentacene, Coronene, 4,4'-Bis(2,2-Diphenylvinyl) Biphenyl (abbreviation: DPVBi), 9,10-bis[4-(2,2-diphenylvinyl) Aromatic hydrocarbon compounds such as phenyl]anthracene (abbreviated as DPVPA) can be used. can.

[0160] Furthermore, as an electron acceptor, 7,7,8,8-tetracyano-2,3,5,6-tetraph Organic compounds such as ruoloquinodimethane (abbreviation: F4-TCNQ) and chloranil, and transition metals Examples include oxides. Also, metals belonging to groups 4 through 8 of the periodic table. Examples of oxides include vanadium oxide, niobium oxide, and tantalum oxide. chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide are used in electricity. It is preferable because it has high receptivity. In particular, molybdenum oxide is stable even in the atmosphere and absorbs It is preferable because it has low humidity and is easy to handle.

[0161] Furthermore, the polymer compounds mentioned above, such as PVK, PVTPA, PTPDMA, and Poly-TPD... Alternatively, a composite material may be formed using the electron acceptors described above and used in the hole injection layer 111.

[0162] The hole transport layer 112 is a layer containing a substance with high hole transport properties. For example, NPB, TPD, BPAFLP, 4,4'-bis[N-(9,9-dimethylfluorinated [Len-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4 '-Bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino] Aromatic amine compounds such as biphenyl (abbreviated as BSPB) can be used. The substances mentioned are mainly 10 -6 cm 2 It is a substance having a hole mobility of / Vs or greater. However, Other materials may be used as long as they have higher hole transport capabilities than electron transport. Layers containing materials with high hole transport properties include not only single layers, but also layers consisting of two or more of the above-mentioned materials. It may also be a layered structure.

[0163] Furthermore, the hole transport layer 112 contains carbazole-inducing agents such as CBP, CzPA, and PCzPA. You can also use anthracene derivatives such as the body, t-BuDNA, DNA, or DPAnth. stomach.

[0164] Furthermore, the hole transport layer 112 contains PVK, PVTPA, PTPDMA, Poly-TPD, and Any polymer compound can be used.

[0165] The light-emitting layer 113 contains an organometallic complex which is one aspect of the present invention as shown in Embodiment 1. It is a layer. The light-emitting layer 113 is formed of a thin film made of an organometallic complex according to one aspect of the present invention. Alternatively, it may have a triplet excitation energy greater than that of an organometallic complex, which is one aspect of the present invention. A substance is used as a host, and an organometallic complex, which is one aspect of the present invention, is dispersed as a guest. The light-emitting layer 113 may be formed with a thin film. This allows the light emission from the organometallic complex to be concentrated. This prevents quenching caused by the degree. Note that triplet excitation energy is... This is the energy difference between the ground state and the triplet excited state.

[0166] The electron transport layer 114 is a layer containing a material with high electron transport properties. Alq3, Tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Alm q3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq) 2) BAlq, Zn(BOX)2, bis[2-(2-hydroxyphenyl)benzothia Examples include metal complexes such as zolatozinc (abbreviation: Zn(BTZ)2). Also, 2-(4 (-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazo PBD (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3 ,4-Oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-ter t-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-tria Zole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl) (Phenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTA) Z), vasophenanthroline (abbreviation: BPhen), vasocuproin (abbreviation: BCP) , 4,4'-bis(5-methylbenzoxazole-2-yl)stilbene (abbreviation: Bz Hetero-aromatic compounds such as Os can also be used. In addition, poly(2,5-pyridine- Diyl) (abbreviation: PPy), poly[(9,9-dihexylfluorene-2,7-diyl) -co-(pyridine-3,5-diyl) (abbreviation: PF-Py), poly[(9,9-geo) Ctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl) Polymer compounds such as (abbreviated as PF-BPy) can also be used. The substances were mainly 10 -6 cm 2 It is a substance with an electron mobility of / Vs or greater. Any material with higher electron transport capabilities than those mentioned above may be used as the electron transport layer. stomach.

[0167] Furthermore, electron transport layers are not limited to single layers, but also consist of two or more layers made of the above material stacked together. It would also be acceptable to do so.

[0168] The electron injection layer 115 is a layer containing a material with high electron injection potential. Lithium, cesium, calcium, lithium fluoride, cesium fluoride, calcium fluoride, Using alkali metals such as lithium oxide, alkaline earth metals, or compounds thereof It is possible to use rare earth metal compounds such as erbium fluoride. Furthermore, the materials that constitute the electron transport layer 114 described above can also be used.

[0169] Alternatively, the electron injection layer 115 may contain a compound formed by mixing an organic compound with an electron donor. Composite materials may be used. Such composite materials can have electrons added to the organic compound by an electron donor. Because it is generated, it has excellent electron injection and electron transport properties. In this case, as an organic compound Preferably, the material is one that is excellent at transporting the generated electrons, specifically, for example, the material described above. The electron transport layer 114 can be composed of materials (such as metal complexes or heteroaromatic compounds). The electron donor can be any substance that exhibits electron-donating properties towards organic compounds. Alkali metals, alkaline earth metals, and rare earth metals are preferred, as are lithium, cesium, Examples include magnesium, calcium, erbium, and ytterbium. Also, alkalis Lithium oxides and alkaline earth metal oxides are preferred, as are lithium oxides and calcium oxides. Examples include barium oxides. Additionally, Lewis bases such as magnesium oxide can be used. It is also possible to use organic compounds such as tetrathiafulvalene (abbreviated as TTF). It can also be done this way.

[0170] Furthermore, the hole injection layer 111, hole transport layer 112, light-emitting layer 113, and electron transport layer 114 described above The electron injection layer 115 is created by vapor deposition (including vacuum deposition), inkjet, and coating, respectively. It can be formed by methods such as weaving.

[0171] The second electrode 103, which functions as a cathode, has a small work function (preferably 3.8 eV or less). (Below) It is preferable to form them using metals, alloys, electrically conductive compounds, and mixtures thereof. Specifically, elements belonging to Group 1 or Group 2 of the periodic table, namely lithium and Alkali metals such as cesium, and alkalis such as magnesium, calcium, and strontium. Earth metals and alloys containing them (e.g., Mg-Ag, Al-Li), Europium In addition to rare earth metals such as ytterbium and alloys containing them, aluminum and silver are also used. It is possible to be there.

[0172] However, of the EL layer 102, the layer formed in contact with the second electrode 103 is organically formed as described above. When using a composite material made by mixing a compound and an electron donor, the work function is large. Regardless of the quantity, indium oxide containing Al, Ag, ITO, silicon, or silicon oxide - Various conductive materials such as tin oxide can be used.

[0173] Furthermore, when forming the second electrode 103, vacuum deposition or sputtering methods may be used. This can be done. Also, when using silver paste, coating methods and inkjet methods can be used. It can be used.

[0174] The above-described light-emitting element is generated by the potential difference between the first electrode 101 and the second electrode 103. When an electric current flows, light is emitted as holes and electrons recombine in the EL layer 102. This light is emitted by passing through either the first electrode 101 or the second electrode 103, or both. And it is taken out to the outside. Therefore, either the first electrode 101 or the second electrode 103 Alternatively, both electrodes may be transparent to visible light.

[0175] Using the light-emitting element shown in this embodiment, a passive matrix type light-emitting device and a transient We will fabricate an active-matrix type light-emitting device in which the driving of the light-emitting elements is controlled by a stator. It is possible.

[0176] Furthermore, the transistor structure when fabricating an active-matrix type light-emitting device is It is not particularly limited. For example, staggered or inverse staggered transistors can be used as appropriate. Yes, it is possible. Furthermore, the drive circuit formed on the substrate can also use N-type and P-type transistors. It can consist of either N-type transistors only or P-type transistors only. It may also be a material. Furthermore, the crystallinity of the semiconductor film used in transistors is also special. It is not limited to these. For example, amorphous semiconductor films, crystalline semiconductor films, etc., can be used. Furthermore, in addition to elements such as silicon, oxide semiconductors can be used as materials for semiconductor films. It is possible.

[0177] In this embodiment, the organometallic complex, which is one aspect of the present invention, was used in the light-emitting layer 113. It has a broad emission spectrum in the wavelength range from red to green. Therefore, it emits light with high color rendering. It is possible to realize the element.

[0178] Furthermore, since the light-emitting element of this embodiment includes an organometallic complex according to one aspect of the present invention, the luminous efficiency It is possible to realize light-emitting elements with high efficiency. Furthermore, it is possible to realize light-emitting elements with low power consumption. This is possible. Furthermore, it is possible to realize highly reliable light-emitting elements.

[0179] In this embodiment, the configurations shown in other embodiments can be used in appropriate combination. can.

[0180] (Embodiment 3) A light-emitting element according to one aspect of the present invention may have a plurality of light-emitting layers. By providing a structure that allows light to be emitted from each light-emitting layer, a mixture of multiple light-emitting elements can be obtained. This can be done. Therefore, for example, white light can be obtained. In this embodiment, multiple An embodiment of a light-emitting element having a light-emitting layer will be explained using Figure 1(B).

[0181] Figure 1(B) shows a light-emitting device having an EL layer 102 between the first electrode 101 and the second electrode 103. This is a diagram showing the element. The EL layer 102 includes a first light-emitting layer 213 and a second light-emitting layer 215. Therefore, the light-emitting element shown in Figure 1(B) consists of light emission in the first light-emitting layer 213 and the second light-emitting layer Mixed emission can be obtained in 215. The first light-emitting layer 213 and the second It is preferable to have a separation layer 214 between the light-emitting layer 215 and the other layer.

[0182] In this embodiment, the first light-emitting layer 213 contains an organic compound that emits blue light, and the second light-emitting layer A light-emitting element containing an organometallic complex according to one aspect of the present invention will be described in the light layer 215, but the present invention is It's not limited to that.

[0183] An organometallic complex according to one aspect of the present invention is used in the first light-emitting layer 213, and in the second light-emitting layer 215 Other luminescent materials may be used.

[0184] The EL layer 102 may have three or more light-emitting layers.

[0185] A voltage is applied such that the potential of the first electrode 101 becomes higher than the potential of the second electrode 103. Then, a current flows between the first electrode 101 and the second electrode 103, and the first light-emitting layer 213, In the light-emitting layer 215 or separation layer 214, holes and electrons recombine. The resulting excited electrons The energy is distributed to both the first light-emitting layer 213 and the second light-emitting layer 215, and the first light-emitting layer The first light-emitting material contained in 213 and the second light-emitting material contained in the second light-emitting layer 215 are excited. To bring them into this state. Then, the first and second light-emitting materials, which are in an excited state, It emits light when returning to its ground state.

[0186] The first light-emitting layer 213 contains perylene, 2,5,8,11-tetra(tert-butyl) Lylene (abbreviation: TBP), DPVBi, 4,4'-bis[2-(N-ethylcarbazole) -3-yl)vinyl]biphenyl (abbreviation: BCzVBi), BAlq, bis(2-methyl) Fluorescent compounds such as gallium chloride (Gamq2Cl) (-8-quinolinolato) and bis {2-[3,5-bis(trifluoromethyl)phenyl]pyridinato-N,C} 2’ Iri Dium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]), bis [2-(4,6-difluorophenyl)pyridinato-N,C 2’ Iridium (III) Acetylacetonate (abbreviation: [FIr(acac)]), bis[2-(4,6-diflu] Olophenyl)pyridinato-N,C 2’ Iridium(III) picolinate (abbreviation: F Irpic), bis[2-(4,6-difluorophenyl)pyridinate-N,C2’ ]stomach Phosphorescent substances such as lydium(III) tetra(1-pyrazolyl) borate (abbreviation: Fir6) It contains the first luminescent substance, represented by a compound, and has an emission spectrum in the 450-510 nm range. Emission with a peak (i.e., blue to blue-green) is obtained.

[0187] Furthermore, the configuration of the first light-emitting layer 213 is such that when the first light-emitting material is a fluorescent compound, the first light emission Using a material having a singlet excitation energy greater than that of the material as the first host, the first It is preferable that the layer consists of a luminescent material dispersed as a guest. Furthermore, the first luminescent material is In the case of phosphorescent compounds, a substance having a triplet excitation energy greater than that of the first light-emitting substance is used. It is preferable that the layer consists of a first host material and a first luminescent material dispersed as a guest material. Apparently. As for the primary host, in addition to the NPB, CBP, TCTA, etc. mentioned earlier, DNA, t-BuDNA, etc., can be used. Note that the singlet excitation energy is the same as the ground state. This is the energy difference from the singlet excited state.

[0188] The second light-emitting layer 215 contains an organometallic complex according to one aspect of the present invention, and emits red to green light. Light emission is obtained. The configuration of the second light-emitting layer 215 is the same as the light-emitting layer 113 described in Embodiment 2. A similar configuration would suffice.

[0189] Furthermore, the separation layer 214 specifically consists of the TPAQn, NPB, CBP, TCTA, as described above. It can be formed using Znpp2, ZnBOX, etc. In this way, the separation layer 214 By providing this, the light intensity of only one of the first light-emitting layer 213 and the second light-emitting layer 215 can be controlled. This prevents the problem of the signal becoming too strong. However, the separation layer 214 is not necessarily It is not necessary, the ratio of the luminescence intensity of the first luminescent layer 213 to the luminescence intensity of the second luminescent layer 215. To adjust this, it should be set as appropriate.

[0190] In addition, the EL layer 102 includes a hole injection layer 111, a hole transport layer 112, and an electron transport layer. 114. An electron injection layer 115 is provided, but the configuration of these layers is also as described in Embodiment 2. You can apply the configuration of each layer described above. However, these layers are not necessarily required, and It should be set up appropriately according to the child's characteristics.

[0191] Note that the configuration shown in this embodiment can be used in combination with the configurations shown in other embodiments as appropriate. It is possible.

[0192] (Embodiment 4) In this embodiment, as one aspect of the present invention, a structure having multiple EL layers in a light-emitting element ( The stacked element (hereinafter referred to as a stacked element) will be explained using Figure 1(C). This light-emitting element is the first Between the first electrode 101 and the second electrode 103, there are multiple EL layers (in Figure 1(C), the first E This is a stacked light-emitting element having an L layer 700 and a second EL layer 701. Now, let's look at the case where there are two EL layers, but it's also possible to have three or more layers.

[0193] In this embodiment, the first electrode 101 and the second electrode 103 are as shown in Embodiment 2. Just apply the configuration.

[0194] In this embodiment, all of the multiple EL layers are the same as the EL layers shown in Embodiment 2. The configuration may be as described above, or it may be partially the same configuration. That is, the first EL layer 7 00 and the second EL layer 701 may have the same configuration or a different configuration, and that configuration The same method as in Embodiment 2 can also be applied.

[0195] Furthermore, in Figure 1(C), there is a charge between the first EL layer 700 and the second EL layer 701. A charge generation layer 305 is provided. The charge generation layer 305 consists of a first electrode 101 and a second electrode 1 When a voltage is applied to 03, electrons are injected into one EL layer and holes are injected into the other EL layer. It has the function of providing a second electrode 103 to the first electrode 101. When a voltage is applied to increase the potential, the charge generation layer 305 is transferred to the first EL layer 700. Electrons are injected, and holes are injected into the second EL layer 701.

[0196] Furthermore, the charge generation layer 305 has light transmission to visible light in terms of light extraction efficiency. It is preferable that the charge generation layer 305 is located more than the first electrode 101 and the second electrode 103. It will function even with low conductivity.

[0197] The charge generation layer 305 contains an organic compound with high hole transport properties and an electron acceptor. Even if the configuration is such that it includes an organic compound with high electron transport properties and an electron donor, It is acceptable for both of these configurations to be stacked.

[0198] In a configuration in which an electron acceptor is added to an organic compound with high hole transport, Examples of highly transportable organic compounds include NPB, TPD, TDATA, MTDATA, 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenyl Aromatic amine compounds such as [mino]biphenyl (abbreviated as BSPB) can be used. The substances mentioned here are mainly 10 -6 cm 2It is a substance that has a hole mobility of / Vs or greater. However, if the organic compound has higher hole transport capabilities than electron transport, other substances can be used as well. That's fine.

[0199] Furthermore, as an electron acceptor, 7,7,8,8-tetracyano-2,3,5,6-tetraph Examples include ruoloquinodimethane (abbreviation: F4-TCNQ), chloranil, etc. Furthermore, transition metal oxides can be cited. Also, in groups 4 through 8 of the periodic table... We can list the oxides of the metals to which they belong. Specifically, vanadium oxide, niobium oxide, Tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, ray oxide Tium is preferred because of its high electron-accepting ability. In particular, molybdenum oxide is stable even in the atmosphere. Therefore, it is preferable because it has low hygroscopicity and is easy to handle.

[0200] On the other hand, in the case of a configuration in which an electron donor is added to an organic compound with high electron transport properties, Examples of organic compounds with high electron transport capabilities include Alq, Almq3, BeBq2, and BA. Metal complexes having a quinoline skeleton or a benzoquinoline skeleton, such as lq, can be used. In addition, there are oxazole-based compounds such as Zn(BOX)2 and Zn(BTZ)2, and thiazo Metal complexes having ion ligands can also be used. Furthermore, in addition to metal complexes, PBD, OXD-7, TAZ, BPhen, BCP, etc. can also be used. (Details here) The solid substance is mainly 10 -6 cm 2 It is a substance with an electron mobility of / Vs or greater. Any organic compound with higher electron transport capabilities than pores may be used in addition to those mentioned above.

[0201] Furthermore, the electron donor can be an alkali metal, alkaline earth metal, rare earth metal, or element. Metals belonging to Group 13 of the periodic table, as well as their oxides and carbonates, can be used. Physically, lithium, cesium, magnesium, calcium, ytterbium, indigo It is preferable to use tetrathiafethane, lithium oxide, cesium carbonate, etc. Also, tetrathiafethane Organic compounds such as sen may be used as electron donors.

[0202] Furthermore, by forming the charge generation layer 305 using the materials described above, the EL layer is stacked. This can suppress the rise in drive voltage in such cases.

[0203] In this embodiment, a light-emitting element having two EL layers has been described, but three or more EL layers are also described. The same method can also be applied to light-emitting elements with stacked layers. Like a light-emitting element, multiple EL layers are arranged between a pair of electrodes with a charge generation layer in between. Therefore, it is possible to emit light in the high-brightness region while keeping the current density low. Therefore, long-life elements can be realized. Also, when lighting is used as an application example, the resistance of the electrode material This reduces the voltage drop, enabling uniform illumination over a large area. Furthermore, it allows for low-voltage operation. This makes it possible to realize a light-emitting device that is both functional and consumes little power.

[0204] Furthermore, by making the light-emitting color of each EL layer different, the entire light-emitting element can be desired Light emission of the color can be obtained. For example, in a light-emitting element having two EL layers, the first By making the emission color of the first EL layer and the emission color of the second EL layer complementary, the light-emitting element It is also possible to obtain a light-emitting element that emits white light as a whole. Note that complementary colors are those that are mixed. This refers to the relationship between colors that result in achromatic colors. In other words, it refers to the relationship between complementary colors obtained from light-emitting substances. By mixing the emitted light, white light emission can be obtained.

[0205] The same applies to the light-emitting element having three EL layers; for example, the first EL layer The light color is red, the emission color of the second EL layer is green, and the emission color of the third EL layer is blue. In some cases, the entire light-emitting element can produce white light emission.

[0206] Note that the configuration shown in this embodiment can be used in combination with the configurations shown in other embodiments as appropriate. It is possible.

[0207] (Embodiment 5) In this embodiment, a passive matrix type light-emitting device using a light-emitting element according to one aspect of the present invention is used. This section describes a light-emitting device, specifically an active-matrix type light-emitting device.

[0208] Figures 2 and 3 show examples of passive matrix type light-emitting devices.

[0209] Passive matrix type (also called simple matrix type) light-emitting devices have a stripe-like (band-like) pattern. Multiple anodes are arranged in parallel in a linear fashion, and multiple cathodes are arranged in parallel in a stripe pattern, with each being orthogonal to the others. It is arranged in such a way, with a light-emitting layer sandwiched at the intersection. Therefore, selection The pixel at the intersection of the anode (to which voltage is applied) and the selected cathode lights up. It will become.

[0210] Figures 2(A) to 2(C) show top views of the pixel area before sealing, and Figure 2(A Figure 2(D) is a cross-sectional view obtained by cutting along the dashed line A-A' in Figure 2(C).

[0211] An insulating layer 402 is formed on the substrate 401 as a base insulating layer. Otherwise, it is not necessary to form them in particular. Multiple first ones are formed in a stripe pattern on the insulating layer 402. The electrodes 403 are arranged at equal intervals (Figure 2(A)).

[0212] Furthermore, a partition wall 404 having an opening corresponding to each pixel is provided on the first electrode 403. The partition wall 404 having an opening is made of an insulating material (photosensitive or non-photosensitive organic material (polyimide) (Acrylic, polyamide, polyimideamide, resist or benzocyclobutene), or Each pixel is composed of an SOG film (for example, an SiOx film containing alkyl groups). The corresponding aperture 405 becomes the light-emitting region (Figure 2(B)).

[0213] Multiple parallel inverted tapered lines intersecting the first electrode 403 are placed on the partition wall 404 which has an opening. A tapered partition wall 406 is provided (Figure 2(C)). The inversely tapered partition wall 406 is photolithographic Following the roughing method, a positive-type photosensitive resin is used in which the unexposed areas remain as a pattern. Formed by adjusting the exposure or development time so that the lower part is etched more. do.

[0214] As shown in Figure 2(C), after forming the inversely tapered partition wall 406, as shown in Figure 2(D) The EL layer 407 and the second electrode 408 are formed sequentially. A partition wall 404 with an opening and an inverted tape The combined height of the layer-shaped partitions 406 is greater than the film thickness of the EL layer 407 and the second electrode 408. Because it is set to be so, E is separated into multiple regions as shown in Figure 2(D). The L layer 407 and the second electrode 408 are formed. Note that the multiple separated regions are They are electrically independent.

[0215] The second electrode 408 has parallel struts extending in a direction intersecting the first electrode 403. It is a P-shaped electrode. Furthermore, the EL layer 407 and the second electrode 4 are also located on the inversely tapered partition wall 406. A portion of the conductive layer forming 08 is formed, but the EL layer 407 and the second electrode 408 are different. It is divided.

[0216] In this embodiment, one of the first electrode 403 and the second electrode 408 is an anode. The other side can be either as long as it is the cathode. Note that the stacked structure that constitutes the EL layer 407 This can be adjusted as needed depending on the polarity of the electrodes.

[0217] Furthermore, if necessary, sealing materials such as sealing cans or glass substrates can be attached to the substrate 401 using sealing materials such as adhesive. The light-emitting elements may be bonded together with an adhesive and sealed so that they are placed in a sealed space. This prevents the degradation of the light-emitting element. Furthermore, the sealed space is filled with Materials or dry, inert gas may be used for filling. Furthermore, to prevent deterioration of the light-emitting element due to moisture, etc. To prevent this, a desiccant may be sealed between the substrate and the sealing material. The desiccant will absorb trace amounts of water. The material is desiccated and thoroughly dried. Calcium oxide or barium oxide can be used as a desiccant. Substances that absorb moisture through chemical adsorption, such as alkaline earth metal oxides, It can be used. Other desiccants include zeolites and silica gels, which are physically adsorbent. A substance that adsorbs moisture may also be used.

[0218] Next, the passive matrix type light-emitting device shown in Figures 2(A) to 2(D) is fitted with an FPC, etc. Figure 3 shows a top view of the implemented configuration.

[0219] In Figure 3, the pixel portion that constitutes the image display is such that the scan line group and the data line group are orthogonal to each other. They are crossing each other.

[0220] Here, the first electrode 403 in Figure 2 corresponds to the scan line 503 in Figure 3, and in Figure 2 The second electrode 408 corresponds to the data line 508 in Figure 3, and the inversely tapered partition wall 406 corresponds to partition wall 5 This corresponds to 06. Between data line 508 and scan line 503 is the EL layer 407 shown in Figure 2. Therefore, the intersection indicated by region 505 corresponds to one pixel.

[0221] Furthermore, the scan line 503 is electrically connected to the connecting wire 509 at the wiring end, and the connecting wire 509 is connected It is connected to the FPC511b via the power terminal 510. The data line is connected to the input terminal 512. It is connected to the FPC511a via this.

[0222] Additionally, if necessary, polarizers, circular polarizers (including elliptical polarizers), and phase difference plates (λ / Optical films such as 4-plate, λ / 2-plate, and color filters may be provided as appropriate. An anti-reflective coating may be provided on the plate or circular polarizer. For example, the surface irregularities may diffuse the reflected light. It can also be treated with an anti-glare coating to reduce reflections.

[0223] Note that Figure 3 shows an example in which the drive circuit is not provided on the substrate 501, but the drive circuit is provided on the substrate 501. An IC chip with a circuit may be mounted on the chip.

[0224] Furthermore, when mounting an IC chip, the area surrounding (outside) the pixel area will contain the signals to the pixel area. The data line IC and scan line IC, which have drive circuits for transmitting signals, are connected using the COG method. Each will be implemented. Other implementation technologies besides the COG method include TCP and wire bonding. It can be implemented as is. TCP is an IC that is implemented on a TAB tape, and TAB tape The IC is mounted by connecting it to the wiring on the element formation substrate. Data line side IC, scan line side IC This may be a silicon substrate, or a glass substrate, a quartz substrate, or a plastic substrate. The drive circuit may be formed on a tick substrate using TFTs.

[0225] Next, an example of an active-matrix type light-emitting device will be explained using Figure 4. Figure 4(A) is a top view showing the light-emitting device, and Figure 4(B) is Figure 4(A) cut along the dashed line A-A'. This is a cross-sectional view. The active matrix type light-emitting device according to this embodiment has an element base A pixel section 602 provided on the plate 601, a drive circuit section (source-side drive circuit) 603, and It has a motion circuit section (gate-side drive circuit) 604, a pixel section 602, a drive circuit section 603, The drive circuit section 604 is sealed by the sealing material 605 between the element substrate 601 and the sealing substrate 606. It is sealed between them.

[0226] Furthermore, the element substrate 601 is equipped with a drive circuit section 603 and a drive circuit section 604 that receive signals from an external source. Signals (for example, video signals, clock signals, start signals, or reset signals) and potentials A wiring harness 607 is provided for connecting an external input terminal to transmit signals. This example shows how to provide an FPC (Flexible Printed Circuit) 608 as an input terminal. Yes, it is. Note that only an FPC is shown in the diagram here, but this FPC is a printed circuit board. A (PWB) may be attached. The light-emitting device in this specification includes the light-emitting device body. This also includes the state in which an FPC or PWB is attached to it.

[0227] Next, the cross-sectional structure will be explained using Figure 4(B). The drive circuit section is located on the element substrate 601. And a pixel section is formed, but here, the drive circuit section 603, which is the source side drive circuit, and The pixel section 602 is shown.

[0228] The drive circuit section 603 combines an n-channel TFT 609 and a p-channel TFT 610. This shows an example of how a CMOS circuit is formed. Note that the circuit that forms the drive circuit section is of a different type. The circuits may be formed using CMOS, PMOS, or NMOS circuits. In this form, the driver is integrated with the circuit board, but this is not always necessary. Furthermore, the drive circuit can be formed externally rather than on the circuit board.

[0229] Furthermore, the pixel section 602 includes a TFT 611 for switching and a TFT 612 for current control. Anode 61 electrically connected to the wiring (source electrode or drain electrode) of the TFT612. It is formed by multiple pixels including 3. Furthermore, an insulator 614 covers the end of the anode 613. This is formed by using a positive-type photosensitive acrylic resin. .

[0230] Furthermore, in order to ensure good coverage of the laminated film formed on the upper layer, the upper end of the insulator 614 Alternatively, it is preferable to form a curved surface with curvature at the lower end. For example, insulator 6 When a positive-type photosensitive acrylic resin is used as the material for 14, a curve is formed at the upper end of the insulator 614. It is preferable to have a curved surface with a radius of error (0.2 μm to 3 μm). Also, insulating material 6 14. Negative type that becomes insoluble in etchant by light, or by light Both positive and etchant-soluble types can be used, and are not limited to organic compounds. Both inorganic compounds, such as silicon oxide and silicon oxynitride, can be used. ru.

[0231] An EL layer 615 and a cathode 616 are stacked on the anode 613. 3 is an ITO film, and titanium nitride is used as the wiring for the current control TFT612 connected to the anode 613. A laminated film of a film and a film mainly composed of aluminum, or a titanium nitride film, aluminum When a laminated film is applied with a main component film and a titanium nitride film, the resistance as wiring is also low, IT Good ohmic contact with the O film can be achieved. Note that cathode 61 is not shown in the diagram here. 6 is electrically connected to the external input terminal, FPC608.

[0232] Furthermore, the EL layer 615 is provided with at least an emissive layer, and in addition to the emissive layer, a hole injection layer, The configuration includes a hole transport layer, an electron transport layer, or an electron injection layer as appropriate. Anode 613, EL layer 6 The light-emitting element 617 is formed in a stacked structure with 15 and the cathode 616.

[0233] Furthermore, although only one light-emitting element 617 is shown in the cross-sectional view in Figure 4(B), the pixel section 6 In 02, multiple light-emitting elements are arranged in a matrix. Pixel section 60 In 2, light-emitting elements that can produce three types of light (R, G, B) are selectively formed, and A light-emitting device capable of multi-color display can be formed. Furthermore, when combined with a color filter... By doing so, it can also be used as a light-emitting device capable of full-color display.

[0234] Furthermore, by bonding the sealing substrate 606 to the element substrate 601 with the sealing material 605, A light-emitting element 6 is located in the space 618 surrounded by the sub-substrate 601, the sealing substrate 606, and the sealing material 605. The structure is equipped with 17. In addition, the space 618 contains an inert gas (nitrogen or algonium). This includes not only cases where materials such as 'n' are filled, but also configurations where the material is filled with sealant 605.

[0235] Furthermore, it is preferable to use an epoxy resin for the sealant 605. Also, these materials It is desirable that the material be as impermeable to moisture and oxygen as possible. Also, the encapsulating substrate 606 Materials used include glass substrates and quartz substrates, as well as FRP (Fiberglass Reinforced Plastic). (Forced plastics), PVF (polyvinyl fluoride), polyester or A plastic substrate made of acrylic or the like can be used.

[0236] As described above, an active matrix type light-emitting device can be obtained.

[0237] Note that the configuration shown in this embodiment can be used in combination with the configurations shown in other embodiments as appropriate. It is possible.

[0238] (Embodiment 6) In this embodiment, various electric devices completed using a light-emitting device which is one aspect to which the present invention is applied are shown. Examples of sub-devices and lighting fixtures will be explained using Figures 5 to 7.

[0239] Examples of electronic devices that incorporate light-emitting devices include television equipment (television, or television radio). (Also called a video receiver), computer monitors, digital cameras, digital video cameras Cameras, digital photo frames, mobile phones (also called mobile phones or mobile phone devices), mobile Examples include mobile game consoles, handheld information terminals, audio playback devices, and large game machines such as pachinko machines. It is possible.

[0240] A light-emitting element using an organometallic complex according to one aspect of the present invention is fabricated on a flexible substrate. This makes it possible to realize electronic devices and lighting devices having a curved light-emitting part.

[0241] Furthermore, the pair of electrodes in a light-emitting element using an organometallic complex according to one aspect of the present invention are directed towards visible light. By forming it using a translucent material, an electronic device having a see-through light-emitting part can be created. This makes it possible to realize a lighting device.

[0242] Furthermore, a light-emitting device to which one aspect of the present invention is applied can also be applied to the lighting of automobiles, for example. For example, lighting can be installed on the dashboard, above the windshield, on the ceiling, etc.

[0243] Specific examples of these electronic devices and lighting fixtures are shown in Figures 5 to 7.

[0244] Figure 5(A) shows an example of a television system. The television system 7100 is housed in a casing. The display unit 7103 is incorporated into the body 7101. The display unit 7103 displays images. It is possible to do so, and the light-emitting device can be used in the display unit 7103. This shows a configuration in which the housing 7101 is supported by the stand 7105.

[0245] The television unit 7100 is operated using the control switches on the housing 7101 and a separate remote control. This can be done using the control unit 7110. The remote control unit 7110 has control keys 7109 allows you to control the channel and volume, and the information is displayed on the display unit 7103. The video can be controlled. Furthermore, the remote control unit 7110 can be controlled by the remote control unit. A display unit 7107 may be provided to display the information output from 7110.

[0246] The television system 7100 will consist of a receiver, modem, and other components. It can receive more general television broadcasts, and furthermore, via a modem, it can receive them via wired or wireless connection. By connecting to a communication network, one-way (sender to receiver) or two-way (sender to receiver) communication is possible. It is also possible to communicate information between believers and recipients, or between recipients themselves.

[0247] Figure 5(B) shows a computer, consisting of the main unit 7201, the casing 7202, the display unit 7203, and keys. Includes board 7204, external connection port 7205, pointing device 7206, etc. The computer is manufactured by using a light-emitting device in its display unit 7203.

[0248] Figure 5(C) shows a portable gaming machine, which consists of two cabinets, cabinet 7301 and cabinet 7302. The housing 7301 has a display unit 7 304 is incorporated, and the display unit 7305 is incorporated into the housing 7302. Also, Figure 5 The portable gaming machine shown in (C) also includes a speaker unit 7306, a recording medium insertion unit 7307, LED lamp 7308, input means (operation key 7309, connection terminal 7310, sensor 731) 1 (Force, displacement, position, velocity, acceleration, angular velocity, rotational speed, distance, light, liquid, magnetism, temperature, chemistry) Matter, sound, time, hardness, electric field, electric current, voltage, power, radiation, flow rate, humidity, gradient, vibration, Equipped with a function to measure odor or infrared radiation, a microphone (7312), etc. Of course, the configuration of a portable gaming machine is not limited to those described above, and at least the display unit 730 It is sufficient to use a light-emitting device in both or one of 4 and the display unit 7305, and other auxiliary equipment The configuration can be set up with appropriate features. The portable gaming machine shown in Figure 5(C) has a recording medium. Functions that read programs or data recorded on the device and display them on the display unit, and other mobile It has the function of sharing information by communicating wirelessly with the gaming machine. The functions of a gaming machine are not limited to these, and it can have a variety of functions.

[0249] Figure 5(D) shows an example of a mobile phone. The mobile phone 7400 is housed in the casing 7401. In addition to the built-in display unit 7402, there are operation buttons 7403, an external connection port 7404, and a speaker. It is equipped with a microphone 7405, microphone 7406, etc. Note that the mobile phone 7400 is equipped with a light-emitting device. It is manufactured by using the display unit 7402.

[0250] The mobile phone 7400 shown in Figure 5(D) allows information to be accessed by touching the display unit 7402 with a finger or the like. You can input [text]. Also, you can perform operations such as making a phone call or composing an email. This can be done by touching the display unit 7402 with a finger or the like.

[0251] The display unit 7402 has three main modes. The first is a display that primarily displays images. The first mode is display mode, the second is input mode which is mainly for inputting information such as characters. The third is display mode. This is a display + input mode, which is a combination of two modes: display mode and input mode.

[0252] For example, when making a phone call or composing an email, the display unit 7402 is used for text input. In this case, the primary text input mode should be used, and you should perform the input operation for the characters displayed on the screen. It is preferable to display a keyboard or number buttons on most of the screen of the display unit 7402. It's nice.

[0253] Furthermore, the 7400 mobile phone has internal sensors that detect tilt, such as a gyroscope and an accelerometer. By providing a detection device, the orientation (vertical or horizontal) of the mobile phone 7400 can be determined, and the display The display on the display unit 7402 can be automatically switched.

[0254] Furthermore, screen modes can be switched by touching the display unit 7402 or by operating the housing 7401. This is done by operating button 7403. Also, the type of image displayed on display unit 7402 Therefore, it is also possible to switch between them. For example, the image signal displayed on the display unit is a video signal. Switch to display mode if it's data, or to input mode if it's text data.

[0255] Furthermore, in input mode, the signal detected by the optical sensor of the display unit 7402 is detected and displayed If there is no input via touch operation on unit 7402 for a certain period of time, the screen mode will be changed to input mode. You may also control the system to switch from that display mode to a different mode.

[0256] The display unit 7402 can also function as an image sensor. For example, the display unit 74 By touching device 02 with the palm or fingers, the user can be authenticated by capturing images of their palm print, fingerprints, etc. Furthermore, the display unit may have a backlight that emits near-infrared light or a sensing light source that emits near-infrared light. Using this method, it is also possible to image finger veins, palmar veins, and other veins.

[0257] As described above, by applying the light-emitting device according to one aspect of the present invention, the display unit of an electronic device can achieve high light emission. Light efficiency can be achieved. Furthermore, by applying one aspect of the present invention, reliable Electronic devices can be provided. Furthermore, by applying one aspect of the present invention, power consumption can be reduced. It is possible to manufacture electronic devices.

[0258] Figure 5(E) shows a table lamp fixture, consisting of a lighting unit 7501, a shade 7502, and a variable arm 75 03. Includes support column 7504, base 7505, and power supply 7506. Note that the table lamp fixture is a light-emitting device. It is manufactured by using the base unit 7501 for the lighting section. The lighting fixture is a ceiling-mounted type. This also includes light fixtures or wall-mounted lighting fixtures.

[0259] Figure 6(A) shows an example in which the light-emitting device is used as an indoor lighting device 801. Because it can be expanded to cover an area, it can be used as a large-area lighting device. In addition, roll It can also be used as a type 802 lighting device. Furthermore, as shown in Figure 6(A), the room Even when using the table lamp 803 described in Figure 5(E) in a room equipped with lighting device 801, good.

[0260] Figure 6(B) shows an example of another lighting device. The desktop lighting device shown in Figure 6(B) has a lighting unit 950 1. Includes support column 9503, support base 9505, etc. The lighting unit 9501 is an organic according to one aspect of the present invention. It contains a metal complex. In this way, a light-emitting element according to one aspect of the present invention is made on a flexible substrate. By manufacturing this, a lighting device having a curved surface, or a lighting device having a flexible, bendable lighting section, can be created. It can be placed in this manner. In this way, a flexible light-emitting device can be used as a lighting device. This not only increases the design freedom of lighting devices, but also allows for applications such as the ceilings of cars and dashcams. This makes it possible to install lighting devices even in curved surfaces such as shoeboards.

[0261] Figure 7 shows an example of another lighting device. As described above, one aspect of the present invention is applied to a curved surface Lighting devices can be manufactured. Furthermore, the organometallic complex according to one aspect of the present invention is yellow to orange. Because it emits light, yellow lighting devices and orange lighting devices can be provided. For example, Figure One embodiment of the present invention can be applied to the lighting device 9900 inside the tunnel shown in 7. By applying one aspect of illumination, a lighting device with high luminous efficiency and energy efficiency can be realized. Furthermore, because yellow to orange light is highly visible, it can help prevent accidents. It is possible. Furthermore, since the lighting device to which one aspect of the present invention is applied is a surface light source, the directionality is not excessively strong. This can suppress the deterioration of the condition and reduce the factors contributing to accidents.

[0262] Furthermore, the above-mentioned yellow lighting device can also be applied to yellow rooms, etc. By using a lighting device that applies one aspect to the lighting of the yellow room, shadows are less likely to occur, and the lighting is good. We can provide a good working environment.

[0263] As described above, by applying a light-emitting device according to one aspect of the present invention, the lighting device can achieve high luminous efficiency. This can be achieved. Furthermore, by applying one aspect of the present invention, a highly reliable lighting device can be created. Furthermore, by applying one aspect of the present invention, a lighting system with low power consumption can be provided. A structure can be created.

[0264] As described above, electronic devices and lighting fixtures can be obtained by applying a light-emitting device. Its range of applications is extremely broad, and it can be applied to electronic devices in all fields.

[0265] Note that the configuration shown in this embodiment can be used in combination with the configurations shown in other embodiments as appropriate. It is possible. [Examples]

[0266] <<Synthesis Example 1>> In this embodiment, an organogold representing one aspect of the present invention, expressed by structural formula (100) of Embodiment 1, is used. Group complex, (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium( III) (Also known as: Bis[2-(6-phenyl-4-pyrimidinyl-κN3)phenyl-κ C](2,4-pentanedionato-κ) 2 O,O') Iridium(III)) (Abbreviation: [I A specific example of the synthesis of [Ir(dppm)2(acac)]) will be given. The structure of m)2(acac) is shown below.

[0267] [ka]

[0268] <Step 1: Synthesis of 4,6-diphenylpyrimidine (abbreviation: Hdppm)> First, 5.02g of 4,6-dichloropyrimidine, 8.29g of phenylboronic acid, and sodium carbonate. 7.19g of phosphate, bis(triphenylphosphine)palladium(II) dichloride (abbreviated) (Name: Pd(PPh3)2Cl2) 0.29g, water 20mL, acetonitrile 20mL, The mixture was placed in a round-bottom flask fitted with a reflux tubing, and the inside was purged with argon. Microwave was then added to this reaction vessel. The material was heated by irradiating it with a wave (2.45 GHz, 100 W) for 60 minutes. Then, further heating was performed. Luboronic acid 2.08g, sodium carbonate 1.79g, Pd(PPh3)2Cl 20.07 Place 0g of the substance, 5mL of water, and 5mL of acetonitrile into a flask and microwave again (2.45G). The solution was heated by irradiating it with a 100W (Hz) light for 60 minutes. Then water was added to this solution, and the solution was mixed. The organic layer was extracted with lolomethane. The resulting extract was washed with water and then treated with magnesium sulfate. The solution was dried. The dried solution was filtered. After removing the solvent from the solution, the resulting residue was... The product was purified by silica gel column chromatography using dichloromethane as the developing solvent, and then... Limidine derivative Hdppm was obtained (yellowish-white powder, yield 38%). Microwave irradiation was used. This was done using a microwave synthesizer (Discover, manufactured by CEM). Step 1 is described below. The synthesis scheme (a-1) is shown below.

[0269] [ka]

[0270] Step 2; di-μ-chloro-bis[bis(4,6-diphenylpyrimidinato)iridi Synthesis of um(III) (abbreviation: [Ir(dppm)2Cl]2) Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the Hdppm1 obtained in step 1 above. 0.10g of iridium chloride hydrate (IrCl3·H2O) and 0.69g of iridium chloride hydrate (IrCl3·H2O) were placed in a reflux tubing. The contents were placed in a round-bottom flask, and the flask was purged with argon. Then, microwave (2.4 The mixture was irradiated with 5GHz (100W) for 1 hour to allow the reaction to proceed. After removing the solvent by distillation, the resulting residue was collected. The solution was filtered with ethanol and then washed to obtain the dinuclear complex [Ir(dppm)2Cl]2 (red). Brown powder, yield 88%. The synthesis scheme for Step 2 (a-2) is shown below.

[0271] [ka]

[0272] Step 3; (Acetylacetonato)bis(4,6-diphenylpyrimidinato)iridi Synthesis of um(III) (abbreviation: [Ir(dppm)2(acac)]) > Furthermore, 40 mL of 2-ethoxyethanol and the [Ir(dppm)2 obtained in step 2 above are added. 21.44g of Cl, 0.30g of acetylacetone, and 1.07g of sodium carbonate are refluxed. The sample was placed in a round-bottom flask with a tube attached, and the inside of the round-bottom flask was purged with argon. Then, micro... The mixture was irradiated with a wave (2.45 GHz, 120 W) for 60 minutes to allow the reaction to proceed. The solvent was removed by distillation, and the result was obtained. The residue was dissolved in dichloromethane and filtered to remove insoluble matter. The resulting filtrate was then mixed with water, and then... The solution was washed with saturated saline solution and dried with magnesium sulfate. The dried solution was then filtered. After removing the solvent from this solution, the resulting residue was collected as dichloromethane:ethyl acetate = 50: The procedure was purified by silica gel column chromatography using a volume ratio of 1 as the developing solvent. By recrystallizing in a mixed solvent of dichloromethane and hexane, the target orange powder is obtained. The end was obtained (yield 32%). The synthesis scheme for step 3 (a-3) is shown below.

[0273] [ka]

[0274] Nuclear magnetic resonance spectroscopy of the orange powder obtained in step 3 above ( 1 Analysis results by 1H NMR This is shown below. Also, 1 The 1H NMR chart is shown in Figure 8. From these results, it can be seen that in this synthesis example 1... In this context, an organometallic complex [Ir( It was found that dppm)2(acac)] was obtained.

[0275] 1 H NMR.δ(CDCl3):1.83(s,6H),5.29(s,1H),6 .48(d,2H),6.80(t,2H),6.90(t,2H),7.55-7.6 3(m,6H),7.77(d,2H),8.17(s,2H),8.24(d,4H) ,9.17(s,2H).

[0276] Next, the UV-Vis absorption spectrum of a dichloromethane solution of [Ir(dppm)2(acac)] The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured. For measuring the metric, a UV-Vis spectrophotometer (V550 model, manufactured by JASCO Corporation) was used. A lolomethane solution (0.093 mmol / L) was placed in a quartz cell and measured at room temperature. Furthermore, a fluorometer (FS920, manufactured by Hamamatsu Photonics Ltd.) was used to measure the emission spectrum. Using this method, the degassed dichloromethane solution (0.093 mmol / L) was placed in a quartz cell at room temperature. Measurements were performed using the following method. The results of the absorption and emission spectra obtained are shown in Figure 9. The horizontal axis represents wavelength (nm), and the vertical axis represents absorption intensity (arbitrary units) and emission intensity (arbitrary units). Also, in Figure 9, two solid lines are shown; the thin solid line shows the absorption spectrum, and the thicker line... The solid line shows the emission spectrum. Note that the absorption spectrum shown in Figure 9 is dichlorometh From the absorption spectrum measured by placing the solution (0.093 mmol / L) in a quartz cell, the The results are shown after subtracting the absorption spectrum measured with only chloromethane placed in a quartz cell. Yes, they are.

[0277] As shown in Figure 9, one embodiment of the present invention is an organometallic complex [Ir(dppm)2(acac) This substance has an emission peak at 592 nm, and an orange emission can be observed from a dichloromethane solution. It was measured.

[0278] Furthermore, [Ir(dppm)2(acac)] is used in the fabrication of light-emitting elements during deposition. It didn't burn easily, and the material utilization efficiency was high. [Examples]

[0279] ≪Synthesis Example 2≫ In this embodiment, the organic gold is an embodiment of the present invention represented by structural formula (140) of Embodiment 1. Group complex, (acetylacetonato)bis(6-methyl-4-phenylpyrimidinato)iridi Um(III) (also known as bis[2-(6-methyl-4-pyrimidinyl-κN3)phenyl) -κC](2,4-pentanedionato-κ 2 O,O') Iridium(III)) (Abbreviation: A concrete example of the synthesis of [Ir(mppm)2(acac)]) is given. Note that [Ir(m The structure of ppm)2(acac) is shown below.

[0280] [ka]

[0281] <Step 1: Synthesis of 4-methyl-6-phenylpyrimidine (abbreviation: Hmppm)> First, 4.90g of 4-chloro-6-methylpyrimidine, 4.80g of phenylboronic acid, charcoal 4.03g sodium phosphate, bis(triphenylphosphine)palladium(II) dichloride Pd(PPh3)2Cl2 (abbreviation) 0.16g, water 20mL, acetonitrile 10mL L was placed in a round-bottom flask fitted with a reflux tubing, and the inside was purged with argon. The material was heated by irradiating it with microwaves (2.45GHz, 100W) for 60 minutes. Phenylboronic acid 2.28g, sodium carbonate 2.02g, Pd(PPh3)2Cl2 Place 0.082g, 5mL of water, and 10mL of acetonitrile into a flask and microwave again ( The solution was heated by irradiating it with 2.45GHz (100W) for 60 minutes. Then, water was added to this solution. In addition, it was extracted with dichloromethane. The obtained extract was mixed with saturated sodium carbonate aqueous solution, water, Next, the solution was washed with saturated saline solution and dried with magnesium sulfate. The dried solution was then filtered. After removing the solvent from this solution by distillation, the resulting residue was divided into dichloromethane:ethyl acetate = 9 Purification is performed by silica gel column chromatography using a volume ratio of :1 as the developing solvent, and the desired result is obtained. The pyrimidine derivative Hmppm was obtained (orange oily substance, yield 46%). The radiation was performed using a microwave synthesizer (CEM Discover). Step 1 is described below. The synthesis scheme (b-1) is shown below.

[0282] [ka]

[0283] Step 2; di-μ-chloro-bis[bis(6-methyl-4-phenylpyrimidinato) Synthesis of Iridium(III) (abbreviation: [Ir(mppm)2Cl]2) Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and Hmppm1 obtained in step 1 above. 0.51g of iridium chloride hydrate (IrCl3·H2O) and 1.26g of iridium chloride hydrate (IrCl3·H2O) were placed in a reflux tubing. The contents were placed in a round-bottom flask, and the flask was purged with argon. Then, microwave (2.4 The mixture was irradiated with 5GHz (100W) for 1 hour to allow the reaction to proceed. After removing the solvent by distillation, the resulting residue was collected. The dinuclear complex [Ir(mppm)2Cl]2 was obtained by washing with ethanol and filtering. (Dark green powder, 77% yield). The synthesis scheme for Step 2 (b-2) is shown below.

[0284] [ka]

[0285] Step 3; (Acetylacetonato)bis(6-methyl-4-phenylpyrimidinato) Synthesis of Iridium(III) (abbreviation: [Ir(mppm)2(acac)]) Furthermore, 40 mL of 2-ethoxyethanol and the dinuclear complex obtained in step 2 above [Ir(mp [pm)2Cl] 21.84g, Acetylacetone 0.48g, Sodium carbonate 1.73g The solution was placed in a round-bottom flask fitted with a reflux tubing, and the contents of the round-bottom flask were replaced with argon. Then, The reaction was carried out by irradiating with microwaves (2.45 GHz, 120 W) for 60 minutes. The solvent was removed by distillation. The resulting residue was dissolved in dichloromethane and filtered to remove insoluble matter. The resulting filtrate The solution was washed with water, then saturated saline solution, and dried with magnesium sulfate. The solution was filtered. After removing the solvent from this solution by distillation, the resulting residue was obtained from dichloromethane:ethyl acetate. The sample was purified by silica gel column chromatography using a 4:1 (volume ratio) solvent-developing solvent. Subsequently, the target product was recrystallized in a mixed solvent of dichloromethane and hexane, resulting in a yellow color. It was obtained as a powder (yield 22%). The synthesis scheme for step 3 (b-3) is shown below.

[0286] [ka]

[0287] Nuclear magnetic resonance spectroscopy of the yellow powder obtained in step 3 above ( 1 Analysis results by 1H NMR This is shown below. Also, 1 The 1H NMR chart is shown in Figure 10. From these results, this synthesis example 2 In this, an organometallic complex [Ir], which is one embodiment of the present invention represented by the above-mentioned structural formula (140). It was found that (mppm)2(acac) was obtained.

[0288] 1 H NMR.δ(CDCl3):1.78(s,6H),2.81(s,6H),5 .24(s,1H),6.37(d,2H),6.77(t,2H),6.85(t,2 H),7.61-7.63(m,4H),8.97(s,2H).

[0289] Next, the UV-Vis absorption spectrum of a dichloromethane solution of [Ir(mppm)2(acac)] The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured. For measuring the metric, a UV-Vis spectrophotometer (V550 model, manufactured by JASCO Corporation) was used. A lolomethane solution (0.10 mmol / L) was placed in a quartz cell and measured at room temperature. For measuring the emission spectrum, a fluorometer (FS920, manufactured by Hamamatsu Photonics Ltd.) was used. Next, place the degassed dichloromethane solution (0.018 mmol / L) into a quartz cell and heat at room temperature. Measurements were performed. The results of the obtained absorption and emission spectra are shown in Figure 11. The horizontal axis represents wavelength (nm), and the vertical axis represents absorption intensity (arbitrary units) and emission intensity (arbitrary units). Also, in Figure 11, two solid lines are shown; the thin solid line shows the absorption spectrum, and the thick solid line shows the absorption spectrum. The solid line shows the emission spectrum. Note that the absorption spectrum shown in Figure 11 is dichloro From the absorption spectrum measured by placing a methane solution (0.10 mmol / L) in a quartz cell, The results shown are obtained by subtracting the absorption spectrum measured with only dichloromethane placed in a quartz cell. It is.

[0290] As shown in Figure 11, one embodiment of the present invention is an organometallic complex [Ir(mppm)2(aca c) has an emission peak at 548 nm, and emits a yellowish-green light from a dichloromethane solution. Light was observed. [Examples]

[0291] ≪Synthesis Example 3≫ In this embodiment, the organic gold is an embodiment of the present invention represented by structural formula (152) of Embodiment 1. Group complex, tris(4,6-diphenylpyrimidinato)iridium(III) (also known as Tri S[2-(6-phenyl-4-pyrimidinyl-κN3)phenyl-κC]iridium(I II)) (abbreviated as [Ir(dppm)3]) will be specifically illustrated as an example of synthesis. Note that [Ir The structure of (dppm)3] is shown below.

[0292] [ka]

[0293] The ligand Hdppm obtained in step 1 of the above synthesis example 1, tris(acetylated) Place 0.49g of cetonate iridium(III) into a reaction vessel fitted with a three-way stopcock, and then... The reaction vessel was purged with argon. Then, it was heated at 250°C for 45.5 hours to allow the reaction to proceed. The substance was dissolved in dichloromethane, and this solution was filtered. The solvent was removed from the resulting filtrate, and Purification was performed by licagel column chromatography. The developing solvent was dichloromethane, followed by Ethyl acetate was used. The solvent of the resulting fraction was removed by distillation to obtain a red solid (yield 41%). %). The obtained solid is recrystallized in a mixed solvent of dichloromethane and hexane. The target product, a red powder, was obtained (yield 11%). The synthesis scheme (c-1) of Synthesis Example 3 was used. See below.

[0294] [ka]

[0295] Nuclear magnetic resonance spectroscopy of the red powder obtained above ( 1 The results of the analysis by 1H NMR are shown below. Yes. Also, 1 The 1H NMR chart is shown in Figure 12. From these results, in this synthesis example 3, One embodiment of the present invention, represented by the structural formula (104) above, is an organometallic complex [Ir(dppm It was found that )3] was obtained.

[0296] 1 H NMR.δ(CDCl3):6.88-7.04(m,9H),7.51-7. 54(m,9H),7.90(d,3H),8.07(d,3H),8.09(d,3H ), 8.21(s,3H), 8.46(s,3H).

[0297] Next, the ultraviolet-visible absorption spectrum of the dichloromethane solution of [Ir(dppm)3] (hereinafter, The absorption spectrum (simply called the "absorption spectrum") and emission spectrum were measured. Measurement of the absorption spectrum For this, a UV-Vis spectrophotometer (V550 model, manufactured by JASCO Corporation) was used to analyze the dichloromethane solution. The solution (0.075 mmol / L) was placed in a quartz cell and measured at room temperature. Additionally, the emission spectrum was measured. For measuring the culm, a fluorometer (FS920, manufactured by Hamamatsu Photonics Ltd.) was used, and degassing was performed. A dichloromethane solution (0.075 mmol / L) was placed in a quartz cell and measured at room temperature. The obtained absorption and emission spectra are shown in Figure 13. The horizontal axis represents wavelength. (nm), the vertical axis represents absorption intensity (arbitrary unit) and emission intensity (arbitrary unit). Also, Figure 13 In the diagram, two solid lines are shown; the thin solid line shows the absorption spectrum, and the thick solid line shows the emission spectrum. The light spectrum is shown. Note that the absorption spectrum shown in Figure 13 is for a dichloromethane solution. From the absorption spectrum measured by placing (0.075 mmol / L) in a quartz cell, dichloro This shows the result after subtracting the absorption spectrum measured with only methane placed in a quartz cell.

[0298] As shown in Figure 13, the organometallic complex [Ir(dppm)3], which is one embodiment of the present invention, is 5 It has an emission peak at 96 nm, and orange emission was observed from a dichloromethane solution. . [Examples]

[0299] (Comparative Example 1) In this example, the organometallic complex, (acetylacetonato)bis(4-phenylpyrimidinato Regarding the synthesis method of iridium(III) (abbreviation: [Ir(ppm)2(acac)]) I will explain this. The structure of [Ir(ppm)2(acac)] is shown below.

[0300] [ka]

[0301] <Step 1; di-μ-chloro-bis[bis(4-phenylpyrimidine)iridium(I Synthesis of (II) (abbreviated as [Ir(ppm)2Cl]2) First, 30 mL of 2-ethoxyethanol, 10 mL of water, and the ligand 4-phenylpyrimidine ( Abbreviated as Hppm) 0.67g, Iridium chloride (IrCl3·HCl·H2O) 0.50 g was placed in a three-necked flask fitted with a reflux tubing, and the inside of the three-necked flask was purged with nitrogen. The mixture was heated under reflux for 13 hours to allow the reaction to proceed. The reaction solution was allowed to cool to room temperature and filtered. The resulting filtration The sample was washed with ethanol to obtain the dinuclear complex [Ir(ppm)2Cl]2 (red powder, absorbed The success rate is 42%. The synthesis scheme (d-1) for step 1 is shown below.

[0302] [ka]

[0303] <Step 2; (Acetylacetonato)bis(4-phenylpyrimidinato)iridium III) Synthesis of (abbreviation: [Ir(ppm)2(acac)]) Furthermore, 20 mL of 2-ethoxyethanol and the dinuclear complex obtained in step 1 above [Ir(pp m)2Cl] 20.37g, acetylacetone 0.11mL, sodium carbonate 0.37g The solution was placed in a three-necked flask fitted with a reflux tubing, and the inside of the three-necked flask was purged with nitrogen. Then, The reaction was carried out by heating under reflux for 17.5 hours. The reaction solution was allowed to cool to room temperature and filtered. The filtrate was then filtered. The medium is removed by distillation, and the resulting residue is used as the developing solvent in silica gel column chromatography with dichloromethane. It was purified by tography. However, recovering the fraction of the target iridium complex was difficult. This was not possible. The resulting fraction was due to the decomposition of the dinuclear complex [Ir(ppm)2Cl]2. This is considered to be the case. The synthesis scheme (d-2) for step 2 is shown below.

[0304] [ka]

[0305] As explained in this comparative example, [Ir(ppm)2(acac)] was difficult to synthesize. Thus, when hydrogen is bonded to the 6th position of the pyrimidine ring, as illustrated in Examples 1-3... An organometallic complex according to one aspect of the present invention (in which a phenyl group is bonded to the 6th position of the pyrimidine ring) Compared to that, the yield was found to be significantly lower, or it was impossible to synthesize. This is because, as mentioned above... This is thought to be because the dinuclear complex [Ir(ppm)2Cl]2 is decomposing. In one aspect of the present invention, an organometallic complex suppresses the decomposition reaction during the synthesis reaction of the complex. Because it can be controlled, the synthesis yield is dramatically improved compared to [Ir(ppm)2(acac)]. To rise. [Examples]

[0306] (Comparative Example 2) In this example, the organometallic complex, tris(4-phenylpyrimidinato)iridium(III) This document explains the synthesis method of [Ir(ppm)3] (abbreviation: [Ir(ppm)3]). The structure of )3] is shown below.

[0307] [ka]

[0308] First, 1.95g of the ligand 4-phenylpyrimidine (abbreviation: Hppm), and Tris(acetyl Place 1.20 g of iridium(III) acetona into a reaction vessel fitted with a three-way stopcock. The reaction vessel was purged with argon. Then, the reaction was carried out by heating at 250°C for 41.5 hours. The reactants were dissolved in dichloromethane, and this solution was filtered. The solvent was removed from the resulting filtrate. A residue was obtained. This residue was purified by silica gel column chromatography. The developing solvent was First, dichloromethane was used, followed by ethyl acetate. The solvent of the resulting fraction was removed by distillation. A brown solid was obtained. The obtained solid was recrystallized in a mixed solvent of dichloromethane and hexane. By doing so, a mixture containing the organometallic complex [Ir(ppm)3] was obtained (brown powder, yield...). 4%). Thin-layer chromatography (TLC) of this mixture revealed brown impurity spots. In comparison, the spot of the target organometallic complex [Ir(ppm)3] was extremely thin, making isolation difficult. This was not possible. The synthesis scheme (e-1) for Comparative Example 2 is shown below.

[0309] [ka]

[0310] As explained in this comparative example, [Ir(ppm)3] was difficult to synthesize. In the case where the substituent bonded to the 6th position of the pyrimidine ring is hydrogen, the original design exemplified in Examples 1-3 Compared to organometallic complexes, which are one manifestation of the phenomenon, the yield is significantly lower, or it may be impossible to synthesize them. It has been revealed that, in one aspect of the present invention, an organometallic complex is used when the synthesis reaction of the complex occurs. Because the decomposition reaction is suppressed, the synthesis yield is dramatically improved compared to [Ir(ppm)3]. To rise. [Examples]

[0311] In this embodiment, a light-emitting element according to one aspect of the present invention will be described with reference to Figure 14. The chemical formulas of the materials used are shown below.

[0312] [ka]

[0313] The method for fabricating the light-emitting element 1 of this embodiment is shown below.

[0314] (light-emitting element 1) First, indium tin oxide (ITSO) containing silicon oxide is spat onto the glass substrate 1100. A first electrode 1101, which functions as an anode, was formed by depositing a film using the tarting method. The film thickness was set to 110 nm, and the electrode area was set to 2 mm × 2 mm.

[0315] As a pretreatment for forming light-emitting elements on the substrate 1100, the substrate surface is washed with water, and 2 After firing at 0°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0316] Then, 10 -4 A substrate is introduced into a vacuum deposition apparatus where the internal pressure is reduced to approximately Pa, and then vacuum deposition is performed. After vacuum firing at 170°C for 30 minutes in the heating chamber of the apparatus, the substrate 1100 is subjected to 3 It was allowed to cool for about 0 minutes.

[0317] Next, the first electrode 1101 is shaped so that the surface on which the first electrode 1101 is formed faces downwards. The completed substrate 1100 is fixed to a substrate holder provided inside the vacuum deposition apparatus, 10 -4 P After reducing the pressure to approximately 'a', 4-phenyl-4'-(9-phenyl Fluoren-9-yl)triphenylamine (abbreviation: BPAFLP) and molybdenum oxide ( A hole injection layer 1111 was formed by co-depositing VI). The film thickness was set to 40 nm. The ratio of BPAFLP to molybdenum oxide is 4:2 by weight (=BPAFLP:molybdenum oxide). The mixture was adjusted to be butene. Note that the co-evaporation method involves using multiple evaporation sources within a single processing chamber. This is a vapor deposition method in which deposition is performed simultaneously from two locations.

[0318] Next, BPAFLP is deposited on the hole injection layer 1111 to a thickness of 20 nm, A pore transport layer 1112 was formed.

[0319] Furthermore, 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h] Noxaline (abbreviation: 2mDBTPDBq-II), 4-phenyl-4'-(9-phenyl -9H-carbazole-3-yl)triphenylamine (abbreviation: PCBA1BP), and (acetylacetonato)bis(6-methyl-4-phenylpyrimidina) synthesized in Example 2 (T) Iridium(III) (abbreviation: [Ir(mppm)2(acac)]) is co-deposited, A light-emitting layer 1113 was formed on the hole transport layer 1112. Here, 2mDBTPDBq-II The weight ratio of PCBA1BP and [Ir(mppm)2(acac)] is 0.8:0.2 :0.05(=2mDBTPDBq-II:PCBA1BP:[Ir(mppm)2(a The settings were adjusted to result in (cac)). The film thickness of the light-emitting layer 1113 was set to 40 nm.

[0320] Next, 2mDBTPDBq-II is deposited on the light-emitting layer 1113 to a thickness of 10 nm. A first electron transport layer 1114a was formed.

[0321] Next, bathophenanthroline (abbreviated as BPhen) is placed on the first electron transport layer 1114a. A second electron transport layer 1114b was formed by depositing a film with a thickness of 20 nm.

[0322] Furthermore, lithium fluoride (LiF) is applied to the second electron transport layer 1114b with a film thickness of 1 nm. A deposition layer was used to form an electron injection layer 1115.

[0323] Finally, a 200 nm film of aluminum is used as the second electrode 1103, which functions as the cathode. The light-emitting element 1 of this embodiment was fabricated by depositing a material to a certain thickness.

[0324] In the vapor deposition process described above, resistance heating was used for all deposition steps.

[0325] Table 1 shows the element structure of the light-emitting element 1 obtained as described above.

[0326] [Table 1]

[0327] The light-emitting element 1 is placed in a glove box under a nitrogen atmosphere, so that the light-emitting element 1 is not exposed to the atmosphere. After sealing the device in a suitable manner, the operating characteristics of the light-emitting element 1 were measured. The measurements were taken at room temperature (in an atmosphere maintained at 25°C).

[0328] Figure 15 shows the current density-luminance characteristics of the light-emitting element 1. In Figure 15, the horizontal axis represents the current density (m A / cm 2 The vertical axis represents luminance (cd / m²). 2 ) represents the voltage-luminance characteristics, which are shown in Figure 16. In Figure 16, the horizontal axis represents voltage (V), and the vertical axis represents luminance (cd / m²). 2 ) represents. Also, shine The luminance-current efficiency characteristics are shown in Figure 17. In Figure 17, the horizontal axis represents luminance (cd / m²). 2 ) on the vertical axis This represents the current efficiency (cd / A). Also, the brightness of the light-emitting element 1 is 950 cd / m². 2 at that time Voltage (V), current density (mA / cm²) 2 ), CIE chromaticity coordinates (x, y), current efficiency (cd) Table 2 shows the power efficiency (lm / W), power efficiency (lm / W), and external quantum efficiency (%).

[0329] [Table 2]

[0330] Furthermore, Figure 18 shows the emission spectrum when a current of 0.1 mA is passed through the light-emitting element 1. In Figure 18, the horizontal axis represents wavelength (nm), and the vertical axis represents emission intensity (in arbitrary units). As shown, the emission spectrum of the light-emitting element had a peak at 544 nm. Also, as shown in Table 2. As expected, 950 cd / m² 2 The CIE chromaticity coordinates of light-emitting element 1 at this brightness are (x,y) = (0 .43,0.56). From this result, the light-emitting element 1 is [Ir(mppm)2(a It was found that yellow emission originating from cac) was obtained.

[0331] As can be seen from Table 2 and Figures 15 to 17, the light-emitting element 1 had good luminous efficiency.

[0332] From the above results, it can be seen that by using an organometallic complex according to one aspect of the present invention as a light-emitting material, high emission It was demonstrated that a device with high optical efficiency can be realized.

[0333] Next, a reliability test was performed on the light-emitting element 1. The results of the reliability test are shown in Figure 19. The vertical axis represents the normalized brightness (%) when the initial brightness is set to 100%, and the horizontal axis represents the drive of the element. This indicates time (h).

[0334] Reliability testing was performed with an initial brightness of 5000 cd / m². 2 Set to the following condition and the current density is constant for the light-emitting element. Driven 1.

[0335] After 110 hours, the brightness of light-emitting element 1 remained at 88% of its initial brightness.

[0336] From the above results, by using an organometallic complex according to one aspect of the present invention as a light-emitting material, reliability It was demonstrated that high-performance elements can be realized. [Examples]

[0337] In this embodiment, a light-emitting element according to one aspect of the present invention will be described with reference to Figure 14. The chemical formulas of the materials used are shown below. Materials already mentioned are omitted.

[0338] [ka]

[0339] The method for fabricating the light-emitting element 2 of this embodiment is shown below.

[0340] (Light-emitting element 2) First, ITSO is deposited on the glass substrate 1100 by sputtering, and the anode is used. A first electrode 1101 capable of performing the function was formed. Its film thickness was 110 nm, and the electrode area was 2 The dimensions were set to mm x 2 mm.

[0341] As a pretreatment for forming light-emitting elements on the substrate 1100, the substrate surface is washed with water, and 2 After firing at 0°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0342] Then, 10 -4 A substrate is introduced into a vacuum deposition apparatus where the internal pressure is reduced to approximately Pa, and then vacuum deposition is performed. After vacuum firing at 170°C for 30 minutes in the heating chamber of the apparatus, the substrate 1100 is subjected to 3 It was allowed to cool for about 0 minutes.

[0343] Next, the first electrode 1101 is shaped so that the surface on which the first electrode 1101 is formed faces downwards. The completed substrate 1100 is fixed to a substrate holder provided inside the vacuum deposition apparatus, 10 -4 P After reducing the pressure to approximately a, BPAFLP and molybdenum oxide (VI) are placed on the first electrode 1101. A hole injection layer 1111 was formed by co-depositing ) and B. The film thickness was set to 40 nm. The ratio of PAFLP to molybdenum oxide is 4:2 by weight (=BPAFLP:molybdenum oxide It was adjusted to become (n).

[0344] Next, BPAFLP is deposited on the hole injection layer 1111 to a thickness of 20 nm, A pore transport layer 1112 was formed.

[0345] Furthermore, 2mDBTPDBq-II,4,4'-di(1-naphthyl)-4''-(9-fu Phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBNBB), and (acetylacetonate)bis(4,6-diphenylpyrimidina) synthesized in Example 1 ) Iridium(III) (abbreviation: [Ir(dppm)2(acac)]) is co-deposited, A light-emitting layer 1113 was formed on the pore transport layer 1112. Here, 2mDBTPDBq-II, The weight ratio of PCBNBB and [Ir(dppm)2(acac)] is 0.8:0.2:0 .05(=2mDBTPDBq-II:PCBNBB:[Ir(dppm)2(acac The settings were adjusted to result in )]). The film thickness of the light-emitting layer 1113 was set to 40 nm.

[0346] Next, 2mDBTPDBq-II is deposited on the light-emitting layer 1113 to a thickness of 10 nm. A first electron transport layer 1114a was formed.

[0347] Next, BPhen is deposited on the first electron transport layer 1114a to a thickness of 20 nm. This formed a second electron transport layer 1114b.

[0348] Furthermore, LiF is deposited on the second electron transport layer 1114b to a thickness of 1 nm, forming an electron injection layer. Formed 1115.

[0349] Finally, a 200 nm film of aluminum is used as the second electrode 1103, which functions as the cathode. The light-emitting element 2 of this embodiment was fabricated by depositing a material to a certain thickness.

[0350] In the vapor deposition process described above, resistance heating was used for all deposition steps.

[0351] Table 3 shows the element structure of the light-emitting element 2 obtained as described above.

[0352] [Table 3]

[0353] The light-emitting element 2 is placed in a glove box under a nitrogen atmosphere, so that the light-emitting element 2 is not exposed to the atmosphere. After sealing the device, the operating characteristics of the light-emitting element 2 were measured. The measurements were taken at room temperature (in an atmosphere maintained at 25°C).

[0354] Figure 20 shows the current density-luminance characteristics of the light-emitting element 2. In Figure 20, the horizontal axis represents the current density (m A / cm 2 The vertical axis represents luminance (cd / m²). 2 ) represents the voltage-luminance characteristics, which are shown in Figure 21. In Figure 21, the horizontal axis represents voltage (V), and the vertical axis represents luminance (cd / m²). 2 ) represents. Also, shine The luminance-current efficiency characteristics are shown in Figure 22. In Figure 22, the horizontal axis represents luminance (cd / m²). 2 ) on the vertical axis This represents the current efficiency (cd / A). The luminance-external quantum efficiency characteristics are shown in Figure 25. Figure 25 In this graph, the horizontal axis represents luminance (cd / m²). 2 The vertical axis of the graph shows the external quantum efficiency (%).

[0355] Furthermore, the brightness of the light-emitting element 2 is 1100 cd / m². 2 Voltage (V) and current density (mA) at that time / cm 2 ), CIE chromaticity coordinates (x, y), current efficiency (cd / A), power efficiency (lm / W) The external quantum efficiency (%) is shown in Table 4.

[0356] [Table 4]

[0357] Furthermore, Figure 23 shows the emission spectrum when a current of 0.1 mA is passed through the light-emitting element 2. In Figure 23, the horizontal axis represents wavelength (nm), and the vertical axis represents emission intensity (in arbitrary units). As shown, the emission spectrum of the light-emitting element had a peak at 579 nm. Also, as shown in Table 4. As expected, 1100 cd / m² 2 The CIE chromaticity coordinates of light-emitting element 2 at this brightness are (x,y) = ( 0.54, 0.46). From this result, the light-emitting element 2 is [Ir(dppm)2( It was found that orange luminescence originating from acac) was obtained.

[0358] As can be seen from Figures 20 to 22 and Figure 25, and Table 4, the light-emitting element 2 has good luminous efficiency. It was good. In particular, the light-emitting element 2 was 1100 cd / m². 2 The external quantum efficiency at brightness is 2 It showed an extremely high value of 8%. For reference, the light extraction efficiency of organic EL elements is typically 20% to 3%. It is said to be around 0%, so absorption by the upper and lower electrodes must be considered (the above light extraction efficiency is approximately...) If we assume a 10% reduction, the limit of external quantum efficiency should be at most around 25%. However, these results surpass those, and the conventional theoretical value of light extraction efficiency was incorrect. This suggests that the theoretical value of the light extraction efficiency is incorrect. By using an organometallic complex according to one aspect of the present invention, a light-emitting element with unprecedented high efficiency can be obtained. It can be achieved.

[0359] From the above results, by using an organometallic complex according to one aspect of the present invention as a luminescent material, high It was demonstrated that it is possible to realize a device with high luminous efficiency.

[0360] Next, a reliability test was performed on the light-emitting element 2. The results of the reliability test are shown in Figure 24. The vertical axis represents the normalized brightness (%) when the initial brightness is set to 100%, and the horizontal axis represents the drive of the element. This indicates time (h).

[0361] Reliability testing was performed with an initial brightness of 5000 cd / m². 2 Set to the following condition and the current density is constant for the light-emitting element. Driven 2.

[0362] After 320 hours, the brightness of light-emitting element 2 remained at 92% of its initial brightness.

[0363] Based on the above results, by using an organometallic complex according to one aspect of the present invention as a luminescent material, reliable It was demonstrated that high-performance elements can be realized. [Examples]

[0364] In this embodiment, a light-emitting element according to one aspect of the present invention will be described with reference to Figure 14. Since the materials used are those shown in Example 6 or 7, their chemical formulas are omitted.

[0365] The method for fabricating the light-emitting element 3 in this embodiment is shown below.

[0366] (light-emitting element 3) First, ITSO is deposited on the glass substrate 1100 by sputtering, and the anode is used. A first electrode 1101 capable of performing the function was formed. Its film thickness was 110 nm, and the electrode area was 2 The dimensions were set to mm x 2 mm.

[0367] As a pretreatment for forming light-emitting elements on the substrate 1100, the substrate surface is washed with water, and 2 After firing at 0°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0368] Then, 10 -4 A substrate is introduced into a vacuum deposition apparatus where the internal pressure is reduced to approximately Pa, and then vacuum deposition is performed. After vacuum firing at 170°C for 30 minutes in the heating chamber of the apparatus, the substrate 1100 is subjected to 3 It was allowed to cool for about 0 minutes.

[0369] Next, the first electrode 1101 is shaped so that the surface on which the first electrode 1101 is formed faces downwards. The completed substrate 1100 is fixed to a substrate holder provided inside the vacuum deposition apparatus, 10 -4 P After reducing the pressure to approximately a, BPAFLP and molybdenum oxide (VI) are placed on the first electrode 1101. A hole injection layer 1111 was formed by co-depositing ) and B. The film thickness was set to 40 nm. The ratio of PAFLP to molybdenum oxide is 4:2 by weight (=BPAFLP:molybdenum oxide It was adjusted to become (n).

[0370] Next, BPAFLP is deposited on the hole injection layer 1111 to a thickness of 20 nm, A pore transport layer 1112 was formed.

[0371] Furthermore, 2mDBTPDBq-II, PCBA1BP, and [Ir( dppm)2(acac)] is co-deposited to form a light-emitting layer 1113 on the hole transport layer 1112. Here, 2mDBTPDBq-II, PCBA1BP and [Ir(dppm)2( The weight ratio of acac) is 0.8:0.2:0.1 (=2mDBTPDBq-II:PC The BA1BP was adjusted to be [Ir(dppm)2(acac)]). Also, the emission was correct. The film thickness of layer 1113 was set to 40 nm.

[0372] Next, 2mDBTPDBq-II is deposited on the light-emitting layer 1113 to a thickness of 15 nm. A first electron transport layer 1114a was formed.

[0373] Next, BPhen is deposited on the first electron transport layer 1114a to a thickness of 15 nm. This formed a second electron transport layer 1114b.

[0374] Furthermore, LiF is deposited on the second electron transport layer 1114b to a thickness of 1 nm, forming an electron injection layer. Formed 1115.

[0375] Finally, a 200 nm film of aluminum is used as the second electrode 1103, which functions as the cathode. The light-emitting element 3 of this embodiment was fabricated by depositing a material to a certain thickness.

[0376] In the vapor deposition process described above, resistance heating was used for all deposition steps.

[0377] Table 5 shows the element structure of the light-emitting element 3 obtained as described above.

[0378] [Table 5]

[0379] The light-emitting element 3 is placed in a glove box under a nitrogen atmosphere, so that the light-emitting element 3 is not exposed to the atmosphere. After sealing the device, the operating characteristics of the light-emitting element 3 were measured. The measurements were taken at room temperature (in an atmosphere maintained at 25°C).

[0380] Figure 26 shows the current density-luminance characteristics of the light-emitting element 3. In Figure 26, the horizontal axis represents the current density (m³). A / cm 2 The vertical axis represents luminance (cd / m²). 2 ) represents the voltage-luminance characteristics, which are shown in Figure 27. In Figure 27, the horizontal axis represents voltage (V), and the vertical axis represents luminance (cd / m²). 2 ) represents. Also, shine The luminance-current efficiency characteristics are shown in Figure 28. In Figure 28, the horizontal axis represents luminance (cd / m²). 2 ) on the vertical axis This represents the current efficiency (cd / A). The luminance-external quantum efficiency characteristics are shown in Figure 31. Figure 31 In this graph, the horizontal axis represents luminance (cd / m²). 2 The vertical axis of the graph shows the external quantum efficiency (%).

[0381] Furthermore, the brightness of the light-emitting element 3 is 1100 cd / m². 2 Voltage (V) and current density (mA) at that time / cm 2 ), CIE chromaticity coordinates (x, y), current efficiency (cd / A), power efficiency (lm / W) The external quantum efficiency (%) is shown in Table 6.

[0382] [Table 6]

[0383] Furthermore, Figure 29 shows the emission spectrum when a current of 0.1 mA is passed through the light-emitting element 3. In Figure 29, the horizontal axis represents wavelength (nm), and the vertical axis represents emission intensity (in arbitrary units). As shown, the emission spectrum of the light-emitting element had a peak at 586 nm. Also, as shown in Table 6. As expected, 1100 cd / m² 2 The CIE chromaticity coordinates of light-emitting element 3 at this brightness are (x,y)=( 0.57, 0.43) From this result, the light-emitting element 3 is [Ir(dppm)2( It was found that orange luminescence originating from acac) was obtained.

[0384] As can be seen from Figures 26-28 and 31, and Table 6, the light-emitting element 3 has good luminescence efficiency. It was good. In particular, the light-emitting element 3 was 1100 cd / m². 2 The external quantum efficiency at brightness is 3 It showed an extremely high value of 1%. For reference, the light extraction efficiency of organic EL elements is typically 20% to 3%. It is said to be around 0%, so absorption by the upper and lower electrodes must be considered (the above light extraction efficiency is approximately...) If we assume a 10% reduction, the limit of external quantum efficiency should be at most around 25%. However, these results surpass those, and the conventional theoretical value of light extraction efficiency was incorrect. This suggests that the theoretical value of the light extraction efficiency is incorrect. By using an organometallic complex according to one aspect of the present invention, a light-emitting element with unprecedented high efficiency can be obtained. It can be achieved.

[0385] From the above results, by using an organometallic complex according to one aspect of the present invention as a luminescent material, high It was demonstrated that it is possible to realize a device with high luminous efficiency.

[0386] Next, a reliability test was performed on the light-emitting element 3. The results of the reliability test are shown in Figure 30. The vertical axis represents the normalized brightness (%) when the initial brightness is set to 100%, and the horizontal axis represents the drive of the element. This indicates time (h).

[0387] Reliability testing was performed with an initial brightness of 5000 cd / m². 2 Set to the following condition and the current density is constant for the light-emitting element. Driven 3.

[0388] After 170 hours, the brightness of the light-emitting element 3 remained at 95% of its initial brightness.

[0389] Based on the above results, by using an organometallic complex according to one aspect of the present invention as a luminescent material, reliable It was demonstrated that high-performance elements can be realized.

[0390] Furthermore, in this Example 8, compared to Example 7, the organometallic complex of one aspect of the present invention in the light-emitting layer The additive concentration is high. As a result, the element of Example 8 has a different emission spectrum compared to the element of Example 7. The Torr (emission color) is redshifted. However, the external quantum efficiency values ​​are all The values ​​are high, and all are highly reliable. Thus, one embodiment of the present invention is an organometallic By changing the concentration of the complex added to the light-emitting layer, the luminescence efficiency and reliability of the device can be reduced. The ability to change the color tone of the emitted light without any modifications is also one of the features of one aspect of the present invention. That is the case. [Examples]

[0391] <<Synthesis Example 4>> In this embodiment, an organogold representing one aspect of the present invention, expressed by structural formula (190) of Embodiment 1, is used. Group complex, (acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidina Iridium(III) (also known as bis[2-(6-tert-butyl-4-pyrimidin) [2,4-Pentanedionato-κC](-κN3)phenyl-κC) 2 O,O') Iridium (III)) (abbreviation: [Ir(tBuppm)2(acac)]) will be given a specific example of synthesis. This is shown below. The structure of [Ir(tBuppm)2(acac)] is shown below.

[0392] [ka]

[0393] Step 1; 4-tert-butyl-6-phenylpyrimidine (abbreviation: HtBuppm) ) synthesis > First, 22.5g of 4,4-dimethyl-1-phenylpentane-1,3-dione and formaldehyde 50g of Mido was placed in a round-bottom flask fitted with a reflux condenser, and the inside was purged with nitrogen. This reaction vessel The reaction solution was refluxed for 5 hours by heating. After that, this solution was treated with sodium hydroxide solution. The organic layer was poured into a solution and extracted with dichloromethane. The obtained organic layer was then mixed with water and saturated saline solution. The solution was washed and dried with magnesium sulfate. The dried solution was filtered. After removing the flux by distillation, the resulting residue is dissolved in hexane:ethyl acetate = 10:1 (volume ratio) The pyrimidine derivative HtBupp was purified using silica gel column chromatography as the substrate. m was obtained (colorless oil, yield 14%). The synthesis scheme for Step 1 is shown below (f-1). vinegar.

[0394] [ka]

[0395] Step 2; Di-μ-chloro-bis[bis(6-tert-butyl-4-phenylpyryl] Synthesis of midinato iridium(III) (abbreviation: [Ir(tBuppm)2Cl]2) > Next, add 15 mL of 2-ethoxyethanol and 5 mL of water, and the HtBupp obtained in step 1 above. m1.49g, iridium chloride hydrate (IrCl3·H2O) 1.04g, attached to a reflux tube. It was placed in a round-bottom flask, and the flask was purged with argon. Then, microwave (2.4 The mixture was irradiated with 5GHz (100W) for 1 hour to allow the reaction to proceed. After removing the solvent by distillation, the resulting residue was collected. The dinuclear complex [Ir(tBuppm)2Cl]2 was obtained by suction filtration and washing with ethanol (yellow). Green powder, yield 73%. The synthesis scheme for Step 2 is shown below (f-2).

[0396] [ka]

[0397] Step 3; (Acetylacetonato)bis(6-tert-butyl-4-phenylpyryl) Iridium(III) (abbreviation: [Ir(tBuppm)2(acac)]) > Furthermore, 40 mL of 2-ethoxyethanol and the dinuclear complex [Ir(tB) obtained in step 2 above are added. [uppm)2Cl] 21.61g, acetylacetone 0.36g, sodium carbonate 1. 27g was placed in a round-bottom flask fitted with a reflux tubing, and the flask was purged with argon. The mixture was then irradiated with microwaves (2.45 GHz, 120 W) for 60 minutes to allow the reaction to proceed. The solvent was then removed by distillation. The resulting residue was filtered by suction with ethanol and washed with water and ethanol. This solid was then processed. Dissolve in chloromethane and use Celite (Wako Pure Chemical Industries, Ltd., catalog number: 531-1) The solution was filtered through a filtration aid consisting of layers of 6855), alumina, and Celite. The resulting solid is then recrystallized in a mixed solvent of dichloromethane and hexane. The target product was obtained as a yellow powder (yield 68%). The synthesis scheme for Step 3 is shown below (f-3). ) is shown.

[0398] [ka]

[0399] Nuclear magnetic resonance spectroscopy of the yellow powder obtained in step 3 above ( 1 Analysis results by 1H NMR This is shown below. Also, 1 The 1H NMR chart is shown in Figure 32. From these results, synthesis example 4 In this, an organometallic complex, which is one aspect of the present invention represented by the above structural formula ((190)), [ It was found that Ir(tBuppm)2(acac) was obtained.

[0400] 1 H NMR.δ(CDCl3):1.50(s,18H),1.79(s,6H), 5.26(s,1H),6.33(d,2H),6.77(t,2H),6.85(t, 2H),7.70(d,2H),7.76(s,2H),9.02(s,2H).

[0401] Next, the UV-Vis absorption of the dichloromethane solution of [Ir(tBuppm)2(acac)] The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured. For spectral measurement, a UV-Vis spectrophotometer (V550 model, manufactured by JASCO Corporation) was used. A dichloromethane solution (0.093 mmol / L) was placed in a quartz cell and measured at room temperature. Furthermore, for measuring the emission spectrum, a fluorometer (Hamamatsu Photonics FS920) was used. Using a ) the degassed dichloromethane solution (0.093 mmol / L) is placed in a quartz cell. Measurements were performed at room temperature. The obtained absorption and emission spectra are shown in Figure 33. The graph shows the wavelength (nm) on the horizontal axis and the absorption intensity (in arbitrary units) and emission intensity (in arbitrary units) on the vertical axis. In addition, two solid lines are shown in Figure 33; the thinner solid line represents the absorption spectrum. The thick solid line shows the emission spectrum. Note that the absorption spectrum shown in Figure 33 is Absorption spectrum of chloromethane solution (0.093 mmol / L) measured in a quartz cell. From this, subtract the absorption spectrum measured by placing only dichloromethane in a quartz cell. It shows the result.

[0402] As shown in Figure 33, one embodiment of the present invention is an organometallic complex [Ir(tBuppm)2(ac (ac) has an emission peak at 547 nm, and when used in a dichloromethane solution, it emits a yellowish-green light. Light emission was observed. [Examples]

[0403] In this embodiment, a light-emitting element according to one aspect of the present invention will be described with reference to Figure 14. The chemical formulas of the materials used are shown below. Materials already mentioned are omitted.

[0404] [ka]

[0405] The method for fabricating the light-emitting element 4 of this embodiment is shown below.

[0406] (Hi-ray 4) First, ITSO is deposited on the glass substrate 1100 by sputtering, and the anode is used. A first electrode 1101 capable of performing the function was formed. Its film thickness was 110 nm, and the electrode area was 2 The dimensions were set to mm x 2 mm.

[0407] As a pretreatment for forming light-emitting elements on the substrate 1100, the substrate surface is washed with water, and 2 After firing at 0°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0408] Then, 10 -4 A substrate is introduced into a vacuum deposition apparatus where the internal pressure is reduced to approximately Pa, and then vacuum deposition is performed. After vacuum firing at 170°C for 30 minutes in the heating chamber of the apparatus, the substrate 1100 is subjected to 3 It was allowed to cool for about 0 minutes.

[0409] Next, the first electrode 1101 is shaped so that the surface on which the first electrode 1101 is formed faces downwards. The completed substrate 1100 is fixed to a substrate holder provided inside the vacuum deposition apparatus, 10 -4 P After reducing the pressure to approximately a, BPAFLP and molybdenum oxide (VI) are placed on the first electrode 1101. A hole injection layer 1111 was formed by co-depositing ) and B. The film thickness was set to 40 nm. The ratio of PAFLP to molybdenum oxide is 4:2 by weight (=BPAFLP:molybdenum oxide It was adjusted to become (n).

[0410] Next, BPAFLP is deposited on the hole injection layer 1111 to a thickness of 20 nm, A pore transport layer 1112 was formed.

[0411] Furthermore, 2mDBTPDBq-II, PCBA1BP, and (acetyl) synthesized in Example 9 Luacetonato)bis(6-tert-butyl-4-phenylpyrimidinato)iridium III) (abbreviation: [Ir(tBuppm)2(acac)]) is co-deposited, and hole transport layer 1 A light-emitting layer 1113 was formed on 112. Here, 2mDBTPDBq-II, PCBA1 The weight ratio of BP and [Ir(tBuppm)2(acac)] is 0.8:0.2:0.0 75(=2mDBTPDBq-II:PCBA1BP:[Ir(tBuppm)2(ac The settings were adjusted to result in (ac)). The film thickness of the light-emitting layer 1113 was set to 40 nm.

[0412] Next, 2mDBTPDBq-II is deposited on the light-emitting layer 1113 to a thickness of 10 nm. A first electron transport layer 1114a was formed.

[0413] Next, BPhen is deposited on the first electron transport layer 1114a to a thickness of 20 nm. This formed a second electron transport layer 1114b.

[0414] Furthermore, LiF is deposited on the second electron transport layer 1114b to a thickness of 1 nm, forming an electron injection layer. Formed 1115.

[0415] Finally, a 200 nm film of aluminum is used as the second electrode 1103, which functions as the cathode. The light-emitting element 4 of this embodiment was fabricated by depositing a material to a certain thickness.

[0416] In the vapor deposition process described above, resistance heating was used for all deposition steps.

[0417] Table 7 shows the element structure of the light-emitting element 4 obtained as described above.

[0418] [Table 7]

[0419] The light-emitting element 4 is placed in a glove box under a nitrogen atmosphere, so that the light-emitting element 4 is not exposed to the atmosphere. After sealing the device in a suitable manner, the operating characteristics of the light-emitting element 4 were measured. The measurements were taken at room temperature (in an atmosphere maintained at 25°C).

[0420] Figure 34 shows the current density-luminance characteristics of the light-emitting element 4. In Figure 34, the horizontal axis represents the current density (m A / cm 2 The vertical axis represents luminance (cd / m²). 2 ) represents the voltage-luminance characteristics, which are shown in Figure 35. In Figure 35, the horizontal axis represents voltage (V), and the vertical axis represents luminance (cd / m²). 2 ) represents. Also, shine The luminance-current efficiency characteristics are shown in Figure 36. In Figure 36, the horizontal axis represents luminance (cd / m²). 2 ) on the vertical axis This represents the current efficiency (cd / A).

[0421] Furthermore, the brightness of the light-emitting element 4 is 1100 cd / m². 2 Voltage (V) and current density (mA) at that time / cm 2 ), CIE chromaticity coordinates (x, y), current efficiency (cd / A), power efficiency (lm / W) The external quantum efficiency (%) is shown in Table 8.

[0422] [Table 8]

[0423] Furthermore, Figure 37 shows the emission spectrum when a current of 0.1 mA is passed through the light-emitting element 4. In Figure 37, the horizontal axis represents wavelength (nm), and the vertical axis represents emission intensity (in arbitrary units). As shown, the emission spectrum of the light-emitting element had a peak at 546 nm. Also, as shown in Table 8. As expected, 1100 cd / m² 2 The CIE chromaticity coordinates of light-emitting element 4 at this brightness are (x,y)=( The values ​​were 0.44, 0.55). From these results, it can be concluded that the light-emitting element 4 is [Ir(tBuppm) It was found that orange emission originated from 2(acac).

[0424] As can be seen from Table 8 and Figures 34 to 36, the light-emitting element 4 had good luminous efficiency.

[0425] From the above results, by using an organometallic complex according to one aspect of the present invention as a luminescent material, high It was demonstrated that it is possible to realize a device with high luminous efficiency. [Examples]

[0426] In this embodiment, a light-emitting element according to one aspect of the present invention will be described with reference to Figure 38. The chemical formulas of the materials used are shown below. Materials already mentioned are omitted.

[0427] [ka]

[0428] The method for fabricating the light-emitting element 5 of this embodiment is shown below.

[0429] (Light-emitting element 5) First, ITSO is deposited on the glass substrate 1100 by sputtering, and the anode is used. A first electrode 1101 capable of performing the function was formed. Its film thickness was 110 nm, and the electrode area was 2 The dimensions were set to mm x 2 mm.

[0430] As a pretreatment for forming light-emitting elements on the substrate 1100, the substrate surface is washed with water, and 2 After firing at 0°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0431] Then, 10 -4 The substrate 1100 is introduced into a vacuum deposition apparatus where the internal pressure is reduced to approximately Pa. After vacuum firing at 170°C for 30 minutes in the heating chamber of the vacuum deposition apparatus, the substrate 11 The 00 was allowed to cool for about 30 minutes.

[0432] Next, the first electrode 1101 is shaped so that the surface on which the first electrode 1101 is formed faces downwards. The completed substrate 1100 is fixed to a substrate holder provided inside the vacuum deposition apparatus, 10 -4 P After reducing the pressure to approximately a, 9-phenyl-3-[4-(10-phenyl [phenyl-9-antryl)phenyl]-9H-carbazole (abbreviation: PCzPA) and oxidation The first hole-injection layer 1111a was formed by co-depositing molybdenum(VI). The film thickness is 60 nm, and the ratio of PCzPA to molybdenum oxide is 1:0.5 by weight. The formula was adjusted to be PCzPA (molybdenum oxide).

[0433] Next, PCzPA is deposited on the first hole injection layer 1111a to a thickness of 30 nm. This formed the first hole transport layer 1112a.

[0434] Furthermore, 9-[4-(N-carbazolyl)]phenyl is placed on the first hole transport layer 1112a. -10-phenylanthracene (abbreviation: CzPA) and N,N'-bis(3-methylphenyl (Lu)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl] Co-depositing with pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn) Then, the first light-emitting layer 1113a was formed. Its film thickness was set to 30 nm, and it consisted of CzPA and 1,6 The ratio of mMemFLPAPrn is 1:0.05 by weight (=CzPA:1,6mMem It was adjusted to be FLPAPrn).

[0435] Next, on the first light-emitting layer 1113a, CzPA is applied with a thickness of 5 nm and BPhen with a thickness of 15 nm. The film was deposited in such a manner to form the first electron transport layer 1114a.

[0436] Then, a 0.1 nm film of lithium oxide (Li2O) is formed on the first electron transport layer 1114a. A thick layer was deposited to form the first electron injection layer 1115a.

[0437] Subsequently, copper phthalocyanine (abbreviated as CuPc) is applied to the first electron injection layer 1115a to form a film thickness. The first intermediate layer 1116a was formed by deposition at 2 nm.

[0438] Next, PCzPA and molybdenum(VI) oxide are co-deposited onto the first intermediate layer 1116a. This formed a second hole injection layer 1111b. Its film thickness was set to 20 nm, and PCzPA The ratio of PCzPA to molybdenum oxide is 1:0.5 by weight (=PCzPA: molybdenum oxide). I adjusted it so that it would work.

[0439] Next, BPAFLP is deposited on the second hole injection layer 1111b to a thickness of 20 nm. This formed a second hole transport layer 1112b.

[0440] Then, on the second hole transport layer 1112b, 2mDBTPDBq-II and PCBA1BP are placed. By co-depositing [Ir(dppm)2(acac)] synthesized in Example 1, the A light-emitting layer 1113b was formed. Its film thickness was set to 40 nm, and 2mDBTPDBq-I The ratio of I, PCBA1BP, and [Ir(dppm)2(acac)] is 0 by weight. 8:0.2:0.06(=2mDBTPDBq-II:PCBA1BP:[Ir(dpp It was adjusted so that it becomes m)2(acac)])

[0441] Next, 2mDBTPDBq-II is applied to the second light-emitting layer 1113b with a film thickness of 15 nm, BPh A second electron transport layer 1114b was formed by depositing en to a thickness of 15 nm.

[0442] Then, Li2O is deposited on the second electron transport layer 1114b to a thickness of 0.1 nm, and the second An electron injection layer 1115b was formed.

[0443] Subsequently, CuPc is deposited on the second electron injection layer 1115b to a thickness of 2 nm, and the second intermediate Layer 1116b was formed.

[0444] Next, PCzPA and molybdenum(VI) oxide are co-deposited onto the second intermediate layer 1116b. This formed a third hole injection layer 1111c. Its film thickness was set to 67 nm, and it was treated with PCzPA The ratio of PCzPA to molybdenum oxide is 1:0.5 by weight (=PCzPA: molybdenum oxide). I adjusted it so that it would work.

[0445] Next, BPAFLP is deposited on the third hole injection layer 1111c to a thickness of 20 nm. This formed a third hole transport layer 1112c.

[0446] Then, on the third hole transport layer 1112c, there is a third light-emitting layer 1113c and a third electron transport layer The third light-emitting layer 1113c and the third electron transport layer 111 4c is similar to the second light-emitting layer 1113b and the second electron transport layer 1114b, respectively. It was formed by its composition.

[0447] Next, LiF is deposited on the third electron transport layer 1114c to a thickness of 1 nm, and the third electron injection... It formed layer 1115c.

[0448] Finally, a second electrode 1103, which functions as a cathode, is placed on the third electron injection layer 1115c. Then, by depositing aluminum to a film thickness of 200 nm, the light-emitting element of this embodiment is created. I created number 5.

[0449] In the vapor deposition process described above, resistance heating was used for all deposition steps.

[0450] Table 9 shows the element structure of the light-emitting element 5 obtained as described above.

[0451] [Table 9]

[0452] The light-emitting element 5 is placed in a glove box under a nitrogen atmosphere, so that the light-emitting element 5 is not exposed to the atmosphere. After sealing the device, the operating characteristics of the light-emitting element 5 were measured. The measurements were taken at room temperature (in an atmosphere maintained at 25°C).

[0453] Figure 39 shows the voltage-luminance characteristics of the light-emitting element 5. In Figure 39, the horizontal axis represents voltage (V), and the vertical axis represents voltage (V). The axis represents luminance (cd / m²). 2 Figure 40 shows the luminance-power efficiency characteristics. In this example, the horizontal axis represents luminance (cd / m²). 2 The vertical axis represents power efficiency (lm / W). The degree-external quantum efficiency characteristics are shown in Figure 41. In Figure 41, the horizontal axis represents luminance (cd / m²). 2 )of, The vertical axis represents the external quantum efficiency (%).

[0454] Furthermore, the brightness of the light-emitting element 5 is 4700 cd / m². 2 Voltage (V) and current density (mA) at that time / cm 2 ), CIE chromaticity coordinates (x, y), current efficiency (cd / A), power efficiency (lm / W) The external quantum efficiency (%) is shown in Table 10.

[0455] [Table 10]

[0456] Furthermore, the emission spectrum when a current of 0.1 mA is passed through the light-emitting element 5 is shown in Figure 42. In figure 43, the horizontal axis represents wavelength (nm), and the vertical axis represents emission intensity (in arbitrary units). This is shown in Figure 42. As shown, the emission spectrum of the light-emitting element had a peak at 581 nm. Also, Table 10 shows As shown, 4700 cd / m² 2 The CIE chromaticity coordinates of the light-emitting element 5 at this brightness are (x,y) = The result was (0.49, 0.42).

[0457] As can be seen from Table 10 and Figures 39 to 41, the light-emitting element 5 had good luminous efficiency. In particular, as can be seen from Figure 40, the light-emitting element 5 has a power efficiency exceeding 50 lm / W. I showed it.

[0458] From the above results, by using an organometallic complex according to one aspect of the present invention as a luminescent material, high It was demonstrated that it is possible to realize a device with high luminous efficiency.

[0459] Next, a reliability test was performed on the light-emitting element 5. The results of the reliability test are shown in Figure 43. The vertical axis represents the normalized brightness (%) when the initial brightness is set to 100%, and the horizontal axis represents the drive of the element. This indicates time (h).

[0460] Reliability testing was performed with an initial brightness of 5000 cd / m². 2 Set to the following condition and the current density is constant for the light-emitting element. I drove the 5.

[0461] After 320 hours, the light-emitting element 5 maintained 95% of its initial brightness.

[0462] Furthermore, a brightness acceleration test was conducted on the light-emitting element 5. The brightness acceleration test was performed on an element with the same structure as the light-emitting element 5. For the element, the initial brightness is 20,000 cd / m². 2 , 30,000 cd / m² 2 , 40,000 cd / m 2 , 50,000 cd / m 2 70,000 cd / m² 2 , and 100,000 cd / m² 2 Each The brightness was set, and a constant current test was performed. Then, the correlation plot of initial brightness-life was obtained from the initial brightness. degree 5000cd / m 2 The lifetime was estimated. In this embodiment, lifetime refers to the lifespan of the light-emitting element. This refers to the time it takes for the brightness of a child to drop below 70% of its initial brightness.

[0463] Figure 44 shows the correlation plot between initial brightness and lifetime. In Figure 44, the vertical axis represents lifetime (h). The horizontal axis shows the initial luminance (cd / m²). 2 This indicates an initial brightness of 20,000 cd / m². 2 , 30,000 cd / m² 2 Regarding this, since it has not fallen below 70% of the initial brightness, the degradation curve... The lifespan was estimated by extrapolating this value. From this result, the initial brightness of the light-emitting element 5 was 5000 cd / m². 2 The estimated lifespan is 30,000 hours, indicating that it is an extremely long-lasting component. Ta.

[0464] Based on the above results, by using an organometallic complex according to one aspect of the present invention as a luminescent material, reliable It was demonstrated that high-performance elements can be realized. [Examples]

[0465] ≪Synthesis Example 5≫ In this embodiment, the organic gold is an embodiment of the present invention represented by structural formula (101) of Embodiment 1. Group complex, bis(4,6-diphenylpyrimidinato)(dipivaloylmethanato)iridium (III) (Also known as: (2,2,6,6-tetramethyl-3,5-heptanedionato-κ) 2 O,O')bis[2-(6-phenyl-4-pyrimidinyl-κN3)phenyl-κC] A specific example of the synthesis of rhidium(III) (abbreviation: [Ir(dppm)2(dpm)]) Let's illustrate with an example. The structure of [Ir(dppm)2(dpm)] is shown below.

[0466] [ka]

[0467] First, add 30 mL of 2-ethoxyethanol and the dinuclear complex [Ir( [dppm)2Cl] 21.93g, dipivaloylmethane 0.77g, sodium carbonate 1. 51g was placed in a round-bottom flask fitted with a reflux tubing, and the flask was purged with argon. Then, it was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. Next, add 0.26 g of dipivaloylmethane to the flask and microwave it again (2.45 GHz). The material was heated by irradiation with 100W for 60 minutes. The solvent was removed by distillation, and the resulting residue was treated with dichloroethylene. The filtrate was dissolved in lomethane and filtered to remove insoluble matter. The resulting filtrate was washed with water and saturated saline solution. The solution was dried with magnesium sulfate. The dried solution was filtered. The solvent was removed from the solution by distillation. Afterward, the resulting residue was washed with toluene. Then, a mixture of dichloromethane and hexane was used. The solution was recrystallized in a solvent to obtain a red solid (yield 28%, purity 95%). This solid was then treated with dichloromethyl The solution was purified by silica gel column chromatography using methane as the developing solvent. Subsequently, the solution was purified using silica gel. A red powder was obtained by recrystallization in a mixed solvent of lolomethane and hexane (yield 6%). The synthesis scheme (g-1) is shown below.

[0468] [ka]

[0469] Nuclear magnetic resonance spectroscopy of the obtained red powder ( 1 The results of the analysis by 1H NMR are shown below. Ta, 1 The 1H NMR chart is shown in Figure 45. From this, it can be seen that in this synthesis example 5, the above One embodiment of the present invention, represented by structural formula (101), is an organometallic complex [Ir(dppm)2(dp It was found that m) was obtained.

[0470] 1 H NMR.δ(CDCl3):1.83(s,18H),5.29(s,1H), 6.55(d,2H),6.80(t,2H),6.91(t,2H),7.55-7. 63(m,6H),7.78(d,2H),8.16(d,2H),8.25(d,4H ), 9.04 (d, 2H).

[0471] Next, the UV-Vis absorption spectrum of a dichloromethane solution with [Ir(dppm)2(dpm)] The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured. For the measurement of Torr, a UV-Vis spectrophotometer (V550 model, manufactured by JASCO Corporation) was used, and dichloro A romethane solution (0.080 mmol / L) was placed in a quartz cell and measured at room temperature. For measuring the emission spectrum, a fluorometer (FS920, manufactured by Hamamatsu Photonics Ltd.) was used. Next, place the degassed dichloromethane solution (0.080 mmol / L) into a quartz cell and heat at room temperature. Measurements were performed. The results of the obtained absorption and emission spectra are shown in Figure 46. The horizontal axis represents wavelength (nm), and the vertical axis represents absorption intensity (arbitrary units) and emission intensity (arbitrary units). Also, in Figure 46, two solid lines are shown; the thin solid line shows the absorption spectrum, and the thick solid line shows the absorption spectrum. The solid line shows the emission spectrum. Note that the absorption spectrum shown in Figure 46 is dichloro From the absorption spectrum measured by placing a methane solution (0.080 mmol / L) in a quartz cell... The results shown are obtained by subtracting the absorption spectrum measured with only dichloromethane placed in a quartz cell. They are doing it.

[0472] As shown in Figure 46, the organometallic complex [Ir(dppm)2(dpm)] in one embodiment of the present invention is It has an emission peak at 610 nm, and a reddish-orange emission was observed from a dichloromethane solution. It was done. [Examples]

[0473] ≪Synthesis Example 6≫ In this embodiment, the organic gold is an embodiment of the present invention represented by structural formula (114) of Embodiment 1. Group complex, (acetylacetonato)bis[4,6-di(naphthalene-2-yl)pyrimidina [T] Iridium(III) (also known as: Bis[3-(6-naphthalene-2-yl-4-pyrim) [Dinyl-κN3)-2-naphthalenyl-κC](2,4-pentanedionato-κ 2 O,O Examples of the synthesis of iridium(III) (abbreviation: [Ir(d2npm)2(acac)]). Let's give a concrete example. The structure of [Ir(d2npm)2(acac)] is shown below. .

[0474] [ka]

[0475] <Step 1: Synthesis of 4-chloro-6-(naphthalene-2-yl)pyrimidine> First, 5.0g of 4,6-dichloropyrimidine, 11.7g of 2-naphthaleneboronic acid, and carbonate Sodium 7.2g, bis(triphenylphosphine)palladium(II) dichloride ( Abbreviation: Pd(PPh3)2Cl2) 0.29g, water 20mL, acetonitrile 20mL Then, the mixture was placed in a round-bottom flask fitted with a reflux tubing, and the inside was purged with argon. Microphone was placed in this reaction vessel. The material was heated by irradiating it with a low-frequency wave (2.45GHz, 100W) for 60 minutes. Then, further heating was performed. Naphthaleneboronic acid 2.9g, sodium carbonate 1.8g, Pd(PPh3)2Cl2O. Place 0.70g of oak, 5mL of water, and 5mL of acetonitrile into a flask and microwave again (2.4°C). The solution was heated by irradiating it with 5GHz (100W) for 60 minutes. Then water was added to this solution. The organic layer was extracted with dichloromethane. The resulting organic layer was washed with water and magnesium sulfate was used. It was dried. The dried solution was filtered. After removing the solvent from this solution, the remaining The slag was subjected to silica gel column chromatography using hexane:ethyl acetate = 5:1 as the developing solvent. The desired pyrimidine derivative, 4-chloro-6-(naphthalene-2-yl)pyrimidine, is purified using a ferrite extract. Minced matter was obtained (yellowish-white powder, yield 48%). Microwave irradiation was performed using a microwave synthesis device. We used the Discover (CEM Corporation) chip. Below is the synthesis scheme for step 1 (h- This shows 1).

[0476] [ka]

[0477] Step 2; 4,6-di(naphthalene-2-yl)pyrimidine (abbreviation: Hd2npm) Synthesis of > Next, 4-chloro-6-(naphthalene-2-yl)pyrimidine 3 obtained in step 1 above. 9g, 2-naphthaleneboronic acid 2.8g, sodium carbonate 1.7g, bis(triphenyl Phosphine) Palladium(II) Dichloride (Abbreviation: Pd(PPh3)2Cl2) 0.1 Place 4g, 20mL of water, and 20mL of acetonitrile into a round-bottom flask fitted with a reflux tubing. The part was purged with argon. Microwave (2.45 GHz 100 W) was applied to this reaction vessel for 60 minutes. It was heated by irradiation for several minutes. Then, 1.4g of 2-naphthaleneboronic acid and sodium carbonate were added. 0.9g of ammonium sulfate, 0.070g of Pd(PPh3)2Cl2, 5mL of water, 5mL of acetonitrile Place L into the flask and irradiate it again with microwaves (2.45 GHz, 100 W) for 60 minutes. The solution was then heated. Water was added to this solution, and the organic layer was extracted with dichloromethane. The prepared organic layer was washed with water and dried with magnesium sulfate. The dried solution was then filtered. After removing the solvent from this solution, the resulting residue was treated with hexane:ethyl acetate in a 5:1 ratio. The target pyrimidine derivative H was purified by flash column chromatography using the open solvent. D2npm was obtained (yellowish-white powder, yield 19%). The synthesis scheme for step 2 is shown below (h- 2) is shown.

[0478] [ka]

[0479] Step 3; di-μ-chloro-bis{bis[4,6-di(naphthalene-2-yl)pyri Synthesis of miginath iridium(III) (abbreviation: [Ir(d2npm)2Cl]2) Next, add 15 mL of 2-ethoxyethanol, 5 mL of water, and the Hd2npm obtained in step 2 above. 1.00g, Iridium chloride hydrate (IrCl3·H2O) (Sigma-Aldric Place 0.44g (manufactured by company H) into a round-bottom flask fitted with a reflux tubing, and purge the flask with argon. Then, microwaves (2.45GHz 100W) were irradiated for one hour to induce a reaction. After removing the solvent by distillation, the resulting residue was washed by suction filtration with ethanol to obtain the dinuclear complex [Ir(d [2npm)2Cl]2 was obtained (brown powder, 98% yield). Below is the synthesis of ski in step 3. This indicates Mu (h-3).

[0480] [ka]

[0481] Step 4; (acetylacetonato)bis[4,6-di(naphthalene-2-yl)pyri Synthesis of miginath iridium(III) (abbreviation: [Ir(d2npm)2(acac)]) > Furthermore, 30 mL of 2-ethoxyethanol and the dinuclear complex [Ir(d2) obtained in step 3 above are added. [npm)2Cl] 21.28g, Acetylacetone 0.22g, Sodium carbonate 0.76g g was placed in a round-bottom flask fitted with a reflux tubing, and the flask was purged with argon. Then, The material was heated by irradiating it with microwaves (2.45GHz, 120W) for 60 minutes. Place 0.22g of acetylacetone into the flask and microwave again (2.45GHz 12 The material was heated by irradiation with 0W for 60 minutes. The solvent was removed by distillation, and the resulting residue was treated with ethanol. The solid was filtered by suction. The resulting solid was washed with water, ethanol, and dichloromethane. The material is dissolved in toluene and filtered through a filtration aid consisting of layers of Celite, alumina, and Celite in that order. After passing through the process, a red powder was obtained by recrystallization in a mixed solvent of toluene and hexane. Yield 11%. The synthesis scheme for step 4 (h-4) is shown below.

[0482] [ka]

[0483] Nuclear magnetic resonance spectroscopy of the obtained red powder ( 1 The results of the analysis by 1H NMR are shown below. Ta, 1 The 1H NMR chart is shown in Figure 47. From this, it can be seen that in this synthesis example 6, the above One embodiment of the present invention, represented by structural formula (114), is an organometallic complex [Ir(d2npm)2(a It was found that (cac) was obtained.

[0484] 1 H NMR.δ(DMSO-d6):1.82(s,6H),5.43(s,1H) ,6.77(s,2H),7.23-7.26(m,4H),7.35-7.38(m, 2H),7.69-7.72(m,4H),7.79-7.82(m,2H),8.09 -8.12(m,2H),8.21-8.26(m,4H),8.68(d,2H),8 0.95 (s, 2H), 9.24-9.27 (m, 6H).

[0485] Next, the UV-Vis absorption spectrum of the dichloromethane solution of [Ir(d2npm)2(acac)] The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured. For the measurement of the vector, a UV-Vis spectrophotometer (V550 model, manufactured by JASCO Corporation) was used. A chloromethane solution (0.073 mmol / L) was placed in a quartz cell and measured at room temperature. Furthermore, a fluorometer (FS920, manufactured by Hamamatsu Photonics Ltd.) was used to measure the emission spectrum. Using this method, a degassed dichloromethane solution (0.073 mmol / L) is placed in a quartz cell, and the chamber is opened. Measurements were performed at temperature. The obtained absorption and emission spectra are shown in Figure 48. The horizontal axis represents wavelength (nm), and the vertical axis represents absorption intensity (arbitrary units) and emission intensity (arbitrary units). Furthermore, in Figure 48, two solid lines are shown; the thinner solid line represents the absorption spectrum. The thick solid line shows the emission spectrum. Note that the absorption spectrum shown in Figure 48 is a dichroic. Absorption spectrum measured using a lolomethane solution (0.073 mmol / L) in a quartz cell. The result obtained by subtracting the absorption spectrum measured with only dichloromethane placed in a quartz cell. This indicates that.

[0486] As shown in Figure 48, one embodiment of the present invention is an organometallic complex [Ir(d2npm)2(acac) This substance has an emission peak at 645 nm, and red emission can be observed from a dichloromethane solution. It was measured. [Examples]

[0487] ≪Synthesis Example 7≫ In this embodiment, the organic gold is an embodiment of the present invention represented by structural formula (115) of Embodiment 1. Group complex, (acetylacetonato)bis[4,6-di(naphthalene-1-yl)pyrimidina [T] Iridium(III) (also known as: Bis[1-(6-naphthalene-1-yl-4-pyrim) [Dinyl-κN3)-2-naphthalenyl-κC](2,4-pentanedionato-κ 2 O,O Examples of the synthesis of iridium(III) (abbreviation: [Ir(d1npm)2(acac)]). Let's give a concrete example. The structure of [Ir(d1npm)2(acac)] is shown below. .

[0488] [ka]

[0489] Step 1; 4,6-di(naphthalene-1-yl)pyrimidine (abbreviation: Hd1npm) Synthesis of > First, 5.00g of 4,6-dichloropyrimidine and 11.56g of 1-naphthaleneboronic acid, 7.12g sodium carbonate, bis(triphenylphosphine)palladium(II) dichlorophosphate Lido (abbreviation: Pd(PPh3)2Cl2) 0.29g, water 20mL, acetonitrile 20 mL was placed in a round-bottom flask fitted with a reflux tubing, and the inside was purged with argon. The material was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. 2.91g of 1-naphthaleneboronic acid, 1.82g of sodium carbonate, and Pd(PPh3)2 Place 20.070g of Cl, 5mL of water, and 5mL of acetonitrile into the flask and microwave again. The solution was heated by irradiating it with a wave (2.45 GHz, 100 W) for 60 minutes. Water was added, and the organic layer was extracted with dichloromethane. The resulting organic layer was saturated with sodium bicarbonate. The solution was washed with aqueous solution, water, and saturated saline solution, and then dried with magnesium sulfate. The liquid was filtered. After removing the solvent from this solution by distillation, the resulting residue was hexane:ethyl acetate = The pyrimidiol was purified by flash column chromatography using a 2:1 solvent-development ratio, and the desired pyrimidiol was obtained. The derivative Hd1npm was obtained (yellowish-white powder, yield 41%). Microwave irradiation was used. A microwave synthesizer (CEM Discover) was used. The synthesis in Step 1 is described below. Scheme (i-1) is shown.

[0490] [ka]

[0491] Step 2; di-μ-chloro-bis{bis[4,6-di(naphthalene-1-yl)pyri Synthesis of miginath iridium(III) (abbreviation: [Ir(d1npm)2Cl]2) Next, 30 mL of 2-ethoxyethanol, 10 mL of water, and the Hd1np obtained in step 1 above. m2.29g, Iridium chloride hydrate (IrCl3·H2O) (Sigma-Aldri Place 1.01g (manufactured by CH) into a round-bottom flask fitted with a reflux condenser, and place the flask in an argon atmosphere. It was replaced. Afterwards, it was irradiated with microwaves (2.45GHz 100W) for 1 hour to induce a reaction. After removing the solvent by distillation, the resulting residue is washed by suction filtration with ethanol to obtain the dinuclear complex [Ir( We obtained [d1npm)2Cl]2 (reddish-brown powder, yield 82%). The synthesis steps for Step 2 are as follows: This shows Keem (i-2).

[0492] [ka]

[0493] Step 3; (acetylacetonato)bis[4,6-di(naphthalene-1-yl)pyri Synthesis of miginath iridium(III) (abbreviation: [Ir(d1npm)2(acac)]) > Furthermore, 30 mL of 2-ethoxyethanol and the dinuclear complex [Ir(d1] obtained in step 2 above are added. [npm)2Cl] 21.18g, Acetylacetone 0.20g, Sodium carbonate 0.70 g was placed in a round-bottom flask fitted with a reflux tubing, and the flask was purged with argon. Then, The material was heated by irradiating it with microwaves (2.45GHz, 120W) for 60 minutes. Place 0.20g of acetylacetone into the flask and microwave again (2.45GHz 12 The material was heated by irradiation with 0W for 60 minutes. The solvent was removed by distillation, and the resulting residue was treated with ethanol. The sample was filtered by suction. The resulting solid was washed with water and ethanol, and dichloromethane was used as the developing solvent. It was purified by flash column chromatography. Then, dichloromethane and hexa Recrystallization in a mixed solvent of Sun yielded a dark red powder (yield 27%). The synthesis scheme (i-3) for step 3 is shown.

[0494] [ka]

[0495] Nuclear magnetic resonance spectroscopy of the obtained dark red powder ( 1 The results of the analysis (using 1H NMR) are shown below. Also, 1 The 1H NMR chart is shown in Figure 49. From this, it can be seen that in this synthesis example 7, the above One embodiment of the present invention, an organometallic complex represented by the structural formula (115) [Ir(d1npm)2( It was found that acac) was obtained.

[0496] 1 H NMR.δ(CDCl3):1.90(s,6H),5.40(s,1H),6 .72(d,2H),7.22(d,2H),7.31(d,2H),7.45(t,2 H),7.62-7.74(m,8H),7.95(d,2H),8.01-8.08( m,4H),8.48-8.52(m,4H),8.77(s,2H),9.34(s, 2H).

[0497] Next, the UV-Vis absorption spectrum of the dichloromethane solution of [Ir(d1npm)2(acac)] The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured. For the measurement of the vector, a UV-Vis spectrophotometer (V550 model, manufactured by JASCO Corporation) was used. A chloromethane solution (0.070 mmol / L) was placed in a quartz cell and measured at room temperature. Furthermore, a fluorometer (FS920, manufactured by Hamamatsu Photonics Ltd.) was used to measure the emission spectrum. Using this method, a degassed dichloromethane solution (0.070 mmol / L) is placed in a quartz cell, and the chamber is opened. Measurements were performed at temperature. The obtained absorption and emission spectra are shown in Figure 50. The horizontal axis represents wavelength (nm), and the vertical axis represents absorption intensity (arbitrary units) and emission intensity (arbitrary units). Furthermore, in Figure 50, two solid lines are shown; the thinner solid line represents the absorption spectrum. The thick solid line shows the emission spectrum. Note that the absorption spectrum shown in Figure 50 is a dichroic. Absorption spectrum measured using a lolomethane solution (0.070 mmol / L) in a quartz cell. The result obtained by subtracting the absorption spectrum measured with only dichloromethane placed in a quartz cell. This indicates that.

[0498] As shown in Figure 50, one embodiment of the present invention is an organometallic complex [Ir(d1npm)2(acac) This substance has an emission peak at 608 nm, and an orange emission can be observed from a dichloromethane solution. It was measured. [Examples]

[0499] ≪Synthesis Example 8≫ In this embodiment, the organic gold is an embodiment of the present invention represented by structural formula (119) of Embodiment 1. Group complex, (acetylacetonato)bis[4,6-di(3-biphenyl)pyrimidinato] Lydium(III) (also known as bis{3-[6-(1,1'-biphenyl-3-yl)-4 [-pyrimidinyl-κN3]-1,1'-biphenyl-4-yl-κC}(2,4-penta Ngionath-κ 2 O,O') Iridium(III)) (Abbreviation: [Ir(d5bpm)2( A concrete example of the synthesis of [acac)]) is given. Note that [Ir(d5bpm)2(acac The structure of ) is shown below.

[0500] [ka]

[0501] Step 1: Synthesis of 4,6-di(3-biphenyl)pyrimidine (abbreviation: Hd5bpm) > First, 5.03g of 4,6-dichloropyrimidine and 13.51g of 3-biphenylboronic acid, 7.17g sodium carbonate, bis(triphenylphosphine)palladium(II) dichlorophosphate Lido (abbreviation: Pd(PPh3)2Cl2) 0.29g, water 30mL, acetonitrile 30 mL was placed in a round-bottom flask fitted with a reflux tubing, and the inside was purged with argon. The material was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. 3.40g of 3-biphenylboronic acid, 1.77g of sodium carbonate, Pd(PPh3)2 Place 20.070g of Cl into a flask and microwave it again (2.45GHz 100W). The solution was heated by irradiation for 60 minutes. Then, water was added to this solution and organic fertilization was performed using dichloromethane. The layer was extracted. The obtained organic layer was washed with saturated sodium bicarbonate solution, water, and saturated saline solution. The solution was dried with magnesium sulfate. The dried solution was filtered. The solvent of this solution was then removed. After removal, the resulting residue is used as a developing solvent for silica gel using toluene:ethyl acetate = 40:1. The desired pyrimidine derivative Hd5bpm was obtained by purification using column chromatography (white Colored powder, yield 10%. Microwave irradiation was performed using a microwave synthesis device (CEM Corporation D). (iscover) was used. The synthesis scheme (j-1) for step 1 is shown below.

[0502] [ka]

[0503] Step 2; di-μ-chloro-bis{bis[4,6-di(3-biphenyl)pyrimidina Synthesis of Iridium(III) (abbreviation: [Ir(d5bpm)2Cl]2) Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the Hd5bpm obtained in step 1 above. 1.14g, Iridium chloride hydrate (IrCl3·H2O) (Sigma-Aldric Place 0.42g (manufactured by company H) into a round-bottom flask fitted with a reflux tubing, and purge the flask with argon. Then, microwaves (2.45GHz 100W) were irradiated for one hour to induce a reaction. After removing the solvent by distillation, the resulting residue was washed by suction filtration with ethanol to obtain the dinuclear complex [Ir(d [5bpm)2Cl]2 was obtained (reddish-brown powder, 99% yield). The synthesis skim of step 2 is shown below. This shows the (j-2) coordinate system.

[0504] [ka]

[0505] Step 3; (Acetylacetonato)bis[4,6-di(3-biphenyl)pyrimidina Synthesis of Iridium(III) (abbreviation: [Ir(d5bpm)2(acac)])) Furthermore, 40 mL of 2-ethoxyethanol and the dinuclear complex obtained in step 2 above [Ir(d5 [bpm)2Cl] 21.38g, Acetylacetone 0.21g, Sodium carbonate 0.74g g was placed in a round-bottom flask fitted with a reflux tubing, and the flask was purged with argon. Then, The material was heated by irradiating it with microwaves (2.45GHz, 120W) for 60 minutes. Place 0.070g of acetylacetone into the flask and microwave again (2.45GHz 1 The material was heated by irradiation with 20W for 60 minutes. The solvent was removed by distillation, and the resulting residue was ethanol. The mixture was filtered by suction. The resulting solid was washed with water and ethanol, and dichloromethane was used as the developing solvent. It was purified by silica gel column chromatography. Then, dichloromethane and he The compound was recrystallized in a xane mixed solvent to obtain a reddish-orange solid. This solid was then subjected to dichloromethane development. The solution was purified by silica gel column chromatography using a solvent, and dichloromethane and hexa By recrystallizing in a mixed solvent, a reddish-orange powder was obtained (yield 17%). Below are the results. The synthesis scheme (j-3) for step 3 is shown.

[0506] [ka]

[0507] Nuclear magnetic resonance spectroscopy of the obtained reddish-orange powder ( 1 The results of the analysis (using 1H NMR) are shown below. Also, 1 The 1H NMR chart is shown in Figure 51. From this, it can be seen that in this synthesis example 8, the above One embodiment of the present invention, represented by the structural formula (119), is an organometallic complex [Ir(d5bpm)2( It was found that acac) was obtained.

[0508] 1 H NMR.δ(CDCl3):1.88(s,6H),5.34(s,1H),6 .62(d,2H),7.10(d,2H),7.29(d,2H),7.36-7.4 5(m,6H),7.50-7.56(m,8H),7.69(t,2H),7.74( d,4H),7.80(d,2H),7.98(s,2H),8.26(d,2H),8 .32(s,2H),8.51(s,2H),9.25(s,2H).

[0509] Next, the UV-Vis absorption spectrum of the dichloromethane solution of [Ir(d5bpm)2(acac)] The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured. For the measurement of the vector, a UV-Vis spectrophotometer (V550 model, manufactured by JASCO Corporation) was used. A chloromethane solution (0.066 mmol / L) was placed in a quartz cell and measured at room temperature. Furthermore, a fluorometer (FS920, manufactured by Hamamatsu Photonics Ltd.) was used to measure the emission spectrum. Using this method, a degassed dichloromethane solution (0.066 mmol / L) is placed in a quartz cell, and the chamber is opened. Measurements were performed at temperature. The obtained absorption and emission spectra are shown in Figure 52. The horizontal axis represents wavelength (nm), and the vertical axis represents absorption intensity (arbitrary units) and emission intensity (arbitrary units). Furthermore, in Figure 52, two solid lines are shown; the thinner solid line represents the absorption spectrum. The thick solid line shows the emission spectrum. Note that the absorption spectrum shown in Figure 52 is a dichroic. Absorption spectrum measured using a lolomethane solution (0.066 mmol / L) in a quartz cell. The result obtained by subtracting the absorption spectrum measured with only dichloromethane placed in a quartz cell. This indicates that.

[0510] As shown in Figure 52, an organometallic complex [Ir(d5bpm)2(acac) This substance has an emission peak at 601 nm, and an orange emission can be observed from a dichloromethane solution. It was measured. [Examples]

[0511] ≪Synthesis Example 9≫ In this embodiment, the organic gold is an embodiment of the present invention represented by structural formula (123) of Embodiment 1. Group complex, (acetylacetonato)bis[4,6-bis(4-methoxyphenyl)pyrimid Sodium Iridium(III) (also known as bis{2-[6-(4-methoxyphenyl)-4- Pyrimidinyl-κN3]-5-methoxyphenyl-κC}(2,4-pentanedionato- κ 2 O,O') Iridium(III) (Abbreviation: [Ir(modppm)2(acac) The following is a specific example of the synthesis of [Ir(modppm)2(acac)]. The construction is shown below.

[0512] [ka]

[0513] <Step 1; 4,6-bis(4-methoxyphenyl)pyrimidine (abbreviation: Hmodpp) m) synthesis > First, 5.01 g of 4,6-dichloropyrimidine and 10.3 g of 4-methoxyphenylboronic acid. 2g, sodium carbonate 7.22g, bis(triphenylphosphine)palladium(II) Dichloride (abbreviation: Pd(PPh3)2Cl2) 0.29g, water 20mL, acetonitrile 20 mL of the solution was placed in a round-bottom flask fitted with a reflux tubing, and the inside was purged with argon. The container was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. In addition, 2.58g of 4-methoxyphenylboronic acid, 1.81g of sodium carbonate, and Pd( Place 0.070g of PPh3)2Cl2, 5mL of water, and 5mL of acetonitrile into a flask. The material was heated again by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. Next, water was added to this solution, and the organic layer was extracted with dichloromethane. The resulting organic layer was saturated carbon Washed with sodium hydrogen oxyhydrate, water, and saturated saline solution, and dried with magnesium sulfate. The dried solution was filtered. After removing the solvent from this solution by distillation, the resulting residue was treated with dichloromethyl Calculation was performed using silica gel column chromatography with tan:ethyl acetate = 10:1 as the developing solvent. The desired pyrimidine derivative, Hmodppm, was obtained (white powder, yield 62%). Microwave irradiation was performed using a microwave synthesizer (Discover, manufactured by CEM). The synthesis scheme (k-1) for step 1 is shown below.

[0514] [ka]

[0515] Step 2; di-μ-chloro-bis{bis[4,6-bis(4-methoxyphenyl)pi Synthesis of limidine iridium(III) (abbreviation: [Ir(modppm)2Cl]2) > Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the Hmodpp obtained in step 1 above. m1.97g, Iridium chloride hydrate (IrCl3·H2O) (Sigma-Aldri Place 1.00g (manufactured by CH) into a round-bottom flask fitted with a reflux tubing, and place the flask in an argon atmosphere. It was replaced. Afterwards, it was irradiated with microwaves (2.45GHz 100W) for 1 hour to induce a reaction. After removing the solvent by distillation, the resulting residue is washed by suction filtration with ethanol to obtain the dinuclear complex [Ir( We obtained modppm)2Cl2 (gray-green powder, 100% yield). The following steps are taken in Step 2. The resulting scheme (k-2) is shown.

[0516] [ka]

[0517] Step 3; (acetylacetonato)bis[4,6-bis(4-methoxyphenyl)pi Limiginato Iridium(III) (abbreviation: Ir(modppm)2(acac)) Synthesis> Furthermore, 40 mL of 2-ethoxyethanol and the dinuclear complex obtained in step 2 above [Ir(mo [dppm)2Cl] 22.80g, Acetylacetone 0.52g, Sodium carbonate 1.8g 3g was placed in a round-bottom flask fitted with a reflux tubing, and the flask was purged with argon. Then, The material was heated by irradiating it with microwaves (2.45 GHz, 120 W) for 60 minutes. Add 0.17g of acetylacetone to the flask and microwave again (2.45GHz 1 The material was heated by irradiation with 20W for 60 minutes. The solvent was removed by distillation, and the resulting residue was ethanol. The mixture was filtered by suction. The resulting solid was washed with water and ethanol, and then dichloromethane:ethyl acetate was used. The solution was purified by silica gel column chromatography using a 25:1 developing solvent ratio. By recrystallizing in a mixed solvent of dichloromethane and hexane, a yellow-orange powder was obtained ( The rate is 13%. The synthesis scheme (k-3) for step 3 is shown below.

[0518] [ka]

[0519] Nuclear magnetic resonance spectroscopy of the obtained yellow-orange powder ( 1 The results of the analysis (using 1H NMR) are shown below. Also, 1 The 1H NMR chart is shown in Figure 53. From this, it can be seen that in this synthesis example 9, the above One embodiment of the present invention, an organometallic complex [Ir(modppm)2] represented by the structural formula (123) It was found that (acac) was obtained.

[0520] 1 H NMR.δ(CDCl3):1.82(s,6H),3.58(s,6H),3 .93(s,6H),5.27(s,1H),5.97(d,2H),6.48(d,2 H),7.08(d,4H),7.69(d,2H),7.95(s,2H),8.19 (d, 4H), 9.01(s, 2H).

[0521] Next, the UV-Vis absorption of the dichloromethane solution of [Ir(modppm)2(acac)] The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured. For spectral measurement, a UV-Vis spectrophotometer (V550 model, manufactured by JASCO Corporation) was used. A dichloromethane solution (0.072 mmol / L) was placed in a quartz cell and measured at room temperature. Furthermore, for measuring the emission spectrum, a fluorometer (Hamamatsu Photonics FS920) was used. Using a ) aerosolized dichloromethane solution (0.072 mmol / L) is placed in a quartz cell. Measurements were performed at room temperature. The obtained absorption and emission spectra are shown in Figure 54. The graph shows the wavelength (nm) on the horizontal axis and the absorption intensity (in arbitrary units) and emission intensity (in arbitrary units) on the vertical axis. In addition, two solid lines are shown in Figure 54; the thinner solid line represents the absorption spectrum. The thick solid line shows the emission spectrum. Note that the absorption spectrum shown in Figure 54 is Absorption spectrum of chloromethane solution (0.072 mmol / L) measured in a quartz cell. From this, subtract the absorption spectrum measured by placing only dichloromethane in a quartz cell. It shows the result.

[0522] As shown in Figure 54, an organometallic complex [Ir(modppm)2(acac] according to one embodiment of the present invention )] has an emission peak at 556 nm, and yellow emission is emitted from a dichloromethane solution. It was observed. [Examples]

[0523] ≪Synthesis Example 10≫ In this embodiment, the organic gold is an embodiment of the present invention represented by structural formula (134) of Embodiment 1. Group complex, (acetylacetonato)bis(4,5,6-triphenylpyrimidinato)iridi Um(III) (also known as: bis[2-(5,6-diphenyl-4-pyrimidinyl-κN3) [phenyl-κC](2,4-pentanedionato-κ 2 O,O') Iridium(III)) A specific example of the synthesis of (abbreviated as [Ir(tppm)2(acac)]) will be given. The structure of Ir(tppm)2(acac) is shown below.

[0524] [ka]

[0525] <Step 1: Synthesis of 4,5,6-triphenylpyrimidine (abbreviation: Htppm)> First, 4.25g of 5-bromo-4,6-dichloropyrimidine and 6.84g of phenylboronic acid. g, sodium carbonate 5.95 g, bis(triphenylphosphine)palladium(II) Chloride (abbreviation: Pd(PPh3)2Cl2) 0.16g, water 20mL, acetonitrile 20 mL was placed in a round-bottom flask fitted with a reflux tubing, and the inside was purged with argon. This reaction volume The container was heated by irradiating it with microwaves (2.45GHz 100W) for 60 minutes. Furthermore, 2.28g of phenylboronic acid, 1.98g of sodium carbonate, and Pd(PPh3)2C are added. Place 20.053g of 1, 5mL of water, and 5mL of acetonitrile into a flask and microwave again. The material was heated by irradiating it with (2.45GHz 100W) for 60 minutes. The solid that subsequently precipitated... The mixture was filtered by suction and washed with water. The resulting residue was treated with dichloromethane:ethyl acetate in a ratio of 10:1. The pyrimidine is purified using flash column chromatography as the developing solvent, and the target pyrimidine is derived. A total of Htppm was obtained (white powder, yield 46%). Microwave irradiation was performed using microwaves. A synthesis apparatus (CEM Discover) was used. The synthesis scheme for Step 1 is shown below. This shows l-1).

[0526] [ka]

[0527] Step 2; di-μ-chloro-bis[bis(4,5,6-triphenylpyrimidinato) Synthesis of Iridium(III) (abbreviation: [Ir(tppm)2Cl]2) Next, 30 mL of 2-ethoxyethanol, 10 mL of water, and the Htppm obtained in step 1 above. 2.60g, Iridium chloride hydrate (IrCl3·H2O) (Sigma-Aldric Place 1.25g (manufactured by company H) into a round-bottom flask fitted with a reflux tubing, and purge the inside of the flask with argon. Then, microwaves (2.45GHz 100W) were irradiated for one hour to induce a reaction. After removing the solvent by distillation, the resulting residue was washed by suction filtration with ethanol to obtain the dinuclear complex [Ir(t We obtained ppm)2Cl]2 (brown powder, 75% yield). The synthesis scheme for Step 2 is shown below. This shows (l-2).

[0528] [ka]

[0529] Step 3; (Acetylacetonato)bis(4,5,6-triphenylpyrimidinato) Synthesis of Iridium(III) (abbreviation: [Ir(tppm)2(acac)]) Furthermore, 30 mL of 2-ethoxyethanol and the dinuclear complex [Ir(tp [pm)2Cl] 21.30g, Acetylacetone 0.23g, Sodium carbonate 0.82g It was placed in a round-bottom flask fitted with a reflux tubing, and the inside of the flask was purged with argon. Then, My The material was heated by irradiating it with Kuro wave (2.45GHz 120W) for 60 minutes. Here, further A Place 0.23g of cetylacetone into the flask and microwave again (2.45GHz 120°C). The material was heated by irradiation with W) for 60 minutes. The solvent was removed by distillation, and the resulting residue was absorbed with ethanol. The solution was filtered. The resulting solid was washed with water and ethanol, and then hexane:ethyl acetate = 2:1 was used. The solution was purified by flash column chromatography using the developing solvent. Subsequently, dichloromethyl A reddish-orange powder was obtained by recrystallization in a mixed solvent of methane and ethanol (yield 29%). %). The synthesis scheme (l-3) for step 3 is shown below.

[0530] [ka]

[0531] Nuclear magnetic resonance spectroscopy of the obtained reddish-orange powder ( 1 The results of the analysis (using 1H NMR) are shown below. Also, 1 The 1H NMR chart is shown in Figure 55. From this, it can be seen that in this synthesis example 10, One embodiment of the present invention, represented by the structural formula (134) described above, is an organometallic complex [Ir(tppm)2( It was found that acac) was obtained.

[0532] 1 H NMR.δ(DMSO-d6):1.87(s,6H),5.43(s,1H) ,6.23(d,2H),6.38(t,2H),6.50(d,2H),6.68(t ,2H),7.28-7.32(m,6H),7.34-7.40(m,8H),7.4 8-7.49 (m, 6H), 9.14 (s, 2H).

[0533] Next, the UV-Vis absorption spectrum of a dichloromethane solution of [Ir(tppm)2(acac)] The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured. For measuring the metric, a UV-Vis spectrophotometer (V550 model, manufactured by JASCO Corporation) was used. A lolomethane solution (0.074 mmol / L) was placed in a quartz cell and measured at room temperature. Furthermore, a fluorometer (FS920, manufactured by Hamamatsu Photonics Ltd.) was used to measure the emission spectrum. The degassed dichloromethane solution (0.074 mmol / L) was placed in a quartz cell at room temperature. Measurements were performed. The obtained absorption and emission spectra are shown in Figure 56. The horizontal axis represents wavelength (nm), and the vertical axis represents absorption intensity (in arbitrary units) and emission intensity (in arbitrary units). Furthermore, although two solid lines are shown in Figure 56, the thin solid line represents the absorption spectrum. The thick solid line shows the emission spectrum. Note that the absorption spectrum shown in Figure 56 is dichloro The absorption spectrum measured by placing a romethane solution (0.074 mmol / L) in a quartz cell. Then, the absorption spectrum measured with only dichloromethane placed in a quartz cell was subtracted from the result. It is showing.

[0534] As shown in Figure 56, an organometallic complex [Ir(tppm)2(acac)] according to one embodiment of the present invention It has an emission peak at 592 nm, and orange emission was observed from a dichloromethane solution. It was done. [Examples]

[0535] <<Synthesis Example 11>> In this embodiment, the organic gold is an embodiment of the present invention represented by structural formula (178) of Embodiment 1. Group complex, Tris(4-methyl-6-phenylpyrimidinato)iridium(III) (also known as Tris[2-(6-methyl-4-pyrimidinyl-κN3)phenyl-κC]iridium (III)) (abbreviated as [Ir(mppm)3]) will be given a specific example of synthesis. Note that [ The structure of Ir(mppm)3] is shown below.

[0536] [ka]

[0537] First, 1.35 g of the ligand Hmppm obtained in Example 2, and tris(acetylacetonate) Place 0.78g of iridium(III) into a reaction vessel fitted with a three-way stopcock, and then... The mixture was purged with argon. Then, it was heated at 250°C for 52 hours to allow the reaction to proceed. The reaction product was then mixed with dichlorocellulose. The solution was dissolved in lomethane and filtered. The solvent was removed from the resulting filtrate, and the silica gel was removed. The solution was purified by microchromatography. The developing solvent was dichloromethane followed by ethyl acetate. The solvent was removed from the obtained fraction by distillation, and a yellowish-brown solid was obtained (crude yield 26%). The resulting solid was subjected to flash column chromatography using ethyl acetate:methanol = 5:1 as the developing solvent. The solution was purified by fluorography. The solvent was removed from the fraction, and the resulting solid was treated with dichlorometh A brown powder was obtained by recrystallization in a mixed solvent of ammonium and hexane (yield 4%). The synthesis scheme (m-1) is shown below.

[0538] [ka]

[0539] Nuclear magnetic resonance spectroscopy of the obtained brown powder ( 1 The results of the analysis by 1H NMR are shown below. Ta, 1 The 1H NMR chart is shown in Figure 57. From this, it can be seen that in this synthesis example 11, the above The organometallic complex [Ir(mppm)3] according to one aspect of the present invention, represented by the structural formula (178), We found out what we had gained.

[0540] 1 H NMR.δ(CDCl3):2.69(s,9H),6.79(d,3H),6 .86-6.97(m,6H),7.63(s,3H),7.72(d,3H),8.1 6(s,3H).

[0541] Next, the ultraviolet-visible absorption spectrum of the dichloromethane solution of [Ir(mppm)3] (hereinafter, The absorption spectrum (simply called the "absorption spectrum") and emission spectrum were measured. Measurement of the absorption spectrum For this, a UV-Vis spectrophotometer (V550 model, manufactured by JASCO Corporation) was used to analyze the dichloromethane solution. The solution (0.095 mmol / L) was placed in a quartz cell and measured at room temperature. Additionally, the emission spectrum was measured. For measuring the culm, a fluorometer (FS920, manufactured by Hamamatsu Photonics Ltd.) was used, and degassing was performed. A dichloromethane solution (0.095 mmol / L) was placed in a quartz cell and measured at room temperature. The obtained absorption and emission spectra are shown in Figure 58. The horizontal axis represents wavelength. (nm), the vertical axis represents absorption intensity (arbitrary unit) and emission intensity (arbitrary unit). Also, see Figure 58. In the diagram, two solid lines are shown; the thin solid line shows the absorption spectrum, and the thick solid line shows the emission spectrum. The light spectrum is shown. Note that the absorption spectrum shown in Figure 58 is for a dichloromethane solution. From the absorption spectrum measured by placing (0.095 mmol / L) in a quartz cell, dichloro This shows the result after subtracting the absorption spectrum measured with only methane placed in a quartz cell.

[0542] As shown in Figure 58, the organometallic complex [Ir(mppm)3] according to one embodiment of the present invention is 548n It exhibits an emission peak at m, and yellowish-green emission was observed from the dichloromethane solution. [Examples]

[0543] ≪Synthesis Example 12≫ In this embodiment, an organogold representing one aspect of the present invention, expressed by structural formula (194) of Embodiment 1, is used. Group complex, bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmeth Sodium iridium(III) (also known as: (2,2,6,6-tetramethyl-3,5-hepta) Ngionath-κ 2 O,O')bis{4-methyl-2-[6-(3-methylphenyl)-4 [Pyrimidinyl-κN3]phenyl-κC}iridium(III)) (Abbreviation: [Ir(5 A specific example of the synthesis of mdppm)2(dpm)) will be given. Note that [Ir(5mdpp The structure of m)2(dpm) is shown below.

[0544] [ka]

[0545] <Step 1; 4,6-bis(3-methylphenyl)pyrimidine (abbreviation: H5mdppm) ) synthesis > First, 4.99g of 4,6-dichloropyrimidine and 9.23g of 3-methylphenylboronic acid. 7.18g sodium carbonate, bis(triphenylphosphine)palladium(II) dichloride Lorid (abbreviation: Pd(PPh3)2Cl2) 0.29 g, water 20 mL, acetonitrile 2 0 mL was placed in a round-bottom flask fitted with a reflux tubing, and the inside was purged with argon. This reaction vessel It was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. Furthermore, 2.31g of 3-methylphenylboronic acid, 1.82g of sodium carbonate, and Pd(PPh 3) Add 0.070g of 2Cl2, 5mL of water, and 5mL of acetonitrile to the flask and mix again. The material was heated by irradiating it with microwaves (2.45GHz, 100W) for 60 minutes. Water was added to the solution, and the organic layer was extracted with dichloromethane. The resulting organic layer was then saturated with bicarbonate. Washed with sodium aqueous solution, water, and saturated saline solution, and dried with magnesium sulfate. The solution was then filtered. After removing the solvent from this solution, the resulting residue was dichloromethane: Purification was performed by silica gel column chromatography using ethyl acetate = 20:1 as the developing solvent. The target pyrimidine derivative H5mdppm was obtained (pale yellow powder, yield 15%). Kuroh wave irradiation was performed using a microwave synthesizer (CEM Discover). See below. The synthesis scheme (n-1) for Step 1 is shown.

[0546] [ka]

[0547] Step 2; di-μ-chloro-bis{bis[4,6-bis(3-methylphenyl)pyri} Synthesis of miginato-iridium(III) (abbreviation: [Ir(5mdppm)2Cl]2) > Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the H5mdpp obtained in step 1 above. m1.06g, Iridium chloride hydrate (IrCl3·H2O) (Sigma-Aldri Place 0.60g (manufactured by CH) into a round-bottom flask fitted with a reflux tubing, and place the flask in an argon atmosphere. It was replaced. Afterwards, it was irradiated with microwaves (2.45GHz 100W) for 1 hour to induce a reaction. After removing the solvent by distillation, the resulting residue is washed by suction filtration with ethanol to obtain the dinuclear complex [Ir( We obtained [5 mdppm]2Cl2 (reddish-brown powder, yield 86%). The synthesis in Step 2 is described below. The scheme (n-2) is shown.

[0548] [ka]

[0549] <Step 3; Bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloy Lumetanato iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)] compound > Furthermore, 30 mL of 2-ethoxyethanol and the dinuclear complex obtained in step 2 above [Ir(5m)] [dppm)2Cl] 21.40g, dipivaloylmethane 0.52g, sodium carbonate 1. 00g was placed in a round-bottom flask fitted with a reflux tubing, and the flask was purged with argon. Then, it was heated by irradiating it with microwaves (2.45 GHz, 120 W) for 60 minutes. Next, add 0.17 g of dipivaloylmethane and 10 mL of 2-ethoxyethanol to the flask. Then, it was heated again by irradiating it with microwaves (2.45 GHz, 120 W) for 60 minutes. The medium was removed by distillation, and the resulting residue was filtered by suction with ethanol. The resulting solid was mixed with water and ethanol. It was washed, dissolved in dichloromethane, and filtered through Celite. After that, dichloromethane Recrystallization was performed using a mixed solvent of tung and ethanol to obtain a red solid (yield 41%, purity 96%). This solid was purified by silica gel column chromatography using toluene as the developing solvent. By recrystallizing in a mixed solvent of dichloromethane and ethanol, a vermilion powder was obtained (yield 8%). The synthesis scheme (n-3) for step 3 is shown below.

[0550] [ka]

[0551] Nuclear magnetic resonance spectroscopy of the obtained vermilion powder ( 1 The results of the analysis by 1H NMR are shown below. Ta, 1 The 1H NMR chart is shown in Figure 59. From this, it can be seen that in this synthesis example 12, the above One embodiment of the present invention, an organometallic complex [Ir(5mdppm)2] represented by the structural formula (194) It was found that (dpm) was obtained.

[0552] 1 H NMR.δ(CDCl3):0.92(s,18H),2.24(s,6H), 2.51(s,6H),5.56(s,1H),6.41(d,2H),6.62(d, 2H),7.36(d,2H),7.48(t,2H),7.58(s,2H),8.0 1(d,2H),8.08(s,2H),8.12(s,2H),9.02(s,2H) .

[0553] Next, the UV-Vis absorption spectrum of the dichloromethane solution [Ir(5mdppm)2(dpm)] The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured. For the measurement of the vector, a UV-Vis spectrophotometer (V550 model, manufactured by JASCO Corporation) was used. A chloromethane solution (0.075 mmol / L) was placed in a quartz cell and measured at room temperature. Furthermore, a fluorometer (FS920, manufactured by Hamamatsu Photonics Ltd.) was used to measure the emission spectrum. Using this method, a degassed dichloromethane solution (0.075 mmol / L) is placed in a quartz cell, and the chamber is opened. Measurements were performed at temperature. The obtained absorption and emission spectra are shown in Figure 60. The horizontal axis represents wavelength (nm), and the vertical axis represents absorption intensity (arbitrary units) and emission intensity (arbitrary units). Furthermore, in Figure 60, two solid lines are shown; the thinner solid line represents the absorption spectrum. The thick solid line shows the emission spectrum. Note that the absorption spectrum shown in Figure 60 is a dichroic. Absorption spectrum measured using a lolomethane solution (0.075 mmol / L) in a quartz cell. The result obtained by subtracting the absorption spectrum measured with only dichloromethane placed in a quartz cell. This indicates that.

[0554] As shown in Figure 60, an organometallic complex [Ir(5mdppm)2(dpm) ] has an emission peak at 620 nm, and a reddish-orange emission is emitted from a dichloromethane solution. It was observed. [Examples]

[0555] ≪Synthesis Example 13≫ In this embodiment, the organic gold is an embodiment of the present invention represented by structural formula (195) of Embodiment 1. Group complex, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrim [Dinato] Iridium(III) (also known as: (2,6-dimethyl-3,5-heptanedionato -κ 2 O,O')bis[4-methyl-2-(3-methyl-4-pyrimidinyl-κN3) [enyl-κC]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm) A concrete example of the synthesis of ]) is given. Note that the composition of [Ir(5mdppm)2(dibm)] The construction is shown below.

[0556] [ka]

[0557] First, add 30 mL of 2-ethoxyethanol and the dinuclear complex [Ir obtained in step 2 of synthesis example 12]. (5 mdppm)2Cl] 21.27g, Diisobutylylmethane 0.40g, Sodium Carbonate 0.90 g of um was placed in a round-bottom flask fitted with a reflux tubing, and the inside of the flask was purged with argon. Then, it was heated by irradiating it with microwaves (2.45 GHz, 120 W) for 60 minutes. Next, add 0.13g of diisobutyrylmethane to the flask and microwave it again (2. The material was heated by irradiation with 45 GHz (200 W) for 60 minutes. The solvent was removed by distillation, and the remaining The residue was filtered by suction with ethanol. The resulting solid was washed with water and ethanol, and then dichlorometh The solution was purified by flash column chromatography using fluorine as the developing solvent. Subsequently, the solution was purified by diclofenac. An orange powder was obtained by recrystallization in a mixed solvent of lolomethane and ethanol (yield 1%). 5%). The synthesis scheme (o-1) is shown below.

[0558] [ka]

[0559] Nuclear magnetic resonance spectroscopy of the obtained orange powder ( 1 The results of the analysis by 1H NMR are shown below. Ta, 1 The 1H NMR chart is shown in Figure 61. From this, it can be seen that in this synthesis example 13, the above One embodiment of the present invention, an organometallic complex [Ir(5mdppm)2] represented by the structural formula (195) It was found that (dibm) was obtained.

[0560] 1 H NMR.δ(CDCl3):0.84(d,6H),0.94(d,6H),2 .19-2.25(m,8H),2.51(d,6H),5.25(s,1H),6.4 0(d,2H),6.65(d,2H),7.36(d,2H),7.48(t,2H) ,7.60(s,2H),8.03(d,2H),8.08(s,2H),8.13(s ,2H),9.05(s,2H).

[0561] Next, the UV-Vis absorption of the dichloromethane solution [Ir(5mdppm)2(dibm)] The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured. For spectral measurement, a UV-Vis spectrophotometer (V550 model, manufactured by JASCO Corporation) was used. A dichloromethane solution (0.081 mmol / L) was placed in a quartz cell and measured at room temperature. Furthermore, for measuring the emission spectrum, a fluorometer (Hamamatsu Photonics FS920) was used. Using a ) the degassed dichloromethane solution (0.081 mmol / L) is placed in a quartz cell. Measurements were performed at room temperature. The obtained absorption and emission spectra are shown in Figure 62. The graph shows the wavelength (nm) on the horizontal axis and the absorption intensity (in arbitrary units) and emission intensity (in arbitrary units) on the vertical axis. In addition, although two solid lines are shown in Figure 62, the thinner solid line represents the absorption spectrum. The thick solid line shows the emission spectrum. Note that the absorption spectrum shown in Figure 62 is Absorption spectrum of chloromethane solution (0.081 mmol / L) measured in a quartz cell. From this, subtract the absorption spectrum measured by placing only dichloromethane in a quartz cell. It shows the result.

[0562] As shown in Figure 62, an organometallic complex [Ir(5mdppm)2(dibm) This substance has an emission peak at 614 nm, and emits a reddish-orange light when released from a dichloromethane solution. This was observed. [Examples]

[0563] <<Synthesis Example 14>> In this embodiment, an organogold representing one aspect of the present invention, expressed by structural formula (196) of Embodiment 1, is used. Group complex, bis[4,6-di(naphthalene-1-yl)pyrimidinato](dipivaloylmeth Sodium iridium(III) (also known as: (2,2,6,6-tetramethyl-3,5-hepta) Ngionath-κ 2 O,O')bis[1-(6-naphthalene-1-yl-4-pyrimidinyl] [Ir(d1n)-2-Naphthalenyl-κC]Iridium(III)) (Abbreviation: [Ir(d1n) Let's give a specific example of the synthesis of pm)2(dpm)]). Note that [Ir(d1npm)2( The structure of dpm) is shown below.

[0564] [ka]

[0565] First, add 30 mL of 2-ethoxyethanol and the dinuclear complex [Ir( [d1npm)2Cl] 21.20g, dipivaloylmethane 0.37g, sodium carbonate 0 0.71g was placed in a round-bottom flask fitted with a reflux tubing, and the flask was purged with argon. Next, it was heated by irradiating it with microwaves (2.45GHz 120W) for 60 minutes. Then, 0.37g of dipivaloylmethane was added to the flask and microwaved again (2.45 GHz). The mixture was heated by irradiation with a 120W light for 60 minutes. The solvent was removed by distillation, and the resulting residue was ethanol. The mixture was filtered by suction with gnoll. The resulting solid was washed with water and ethanol, and then hexane:ethyl acetate was used. The material was purified by flash column chromatography using a 5:1 solvent-developing ratio. By recrystallizing the powder in a mixed solvent of dichloromethane and ethanol, a dark red powder was obtained. (Yield 24%). The synthesis scheme (p-1) is shown below.

[0566] [ka]

[0567] Nuclear magnetic resonance spectroscopy of the obtained dark red powder ( 1 The results of the analysis (using 1H NMR) are shown below. Also, 1 The 1H NMR chart is shown in Figure 63. From this, it can be seen that in this synthesis example 14, One embodiment of the present invention, represented by the structural formula (196) described above, is an organometallic complex [Ir(d1npm)2 It was found that (dpm) was obtained.

[0568] 1 H NMR.δ(CDCl3):0.95(s,18H),5.68(s,1H), 6.96(d,2H),7.23(d,2H),7.35(d,2H),7.45(t, 2H),7.60-7.63(m,4H),7.67-7.72(m,4H),7.88 (d,2H),8.00-8.07(m,4H),8.33-8.37(m,2H),8 .51(s,2H),8.70(s,2H),9.22(s,2H).

[0569] Next, the UV-Vis absorption spectrum of a dichloromethane solution of [Ir(d1npm)2(dpm)] The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured. For measuring the metric, a UV-Vis spectrophotometer (V550 model, manufactured by JASCO Corporation) was used. A lolomethane solution (0.064 mmol / L) was placed in a quartz cell and measured at room temperature. Furthermore, a fluorometer (FS920, manufactured by Hamamatsu Photonics Ltd.) was used to measure the emission spectrum. The degassed dichloromethane solution (0.064 mmol / L) was placed in a quartz cell at room temperature. Measurements were performed. The obtained absorption and emission spectra are shown in Figure 64. The horizontal axis represents wavelength (nm), and the vertical axis represents absorption intensity (in arbitrary units) and emission intensity (in arbitrary units). Furthermore, although two solid lines are shown in Figure 64, the thin solid line represents the absorption spectrum. The thick solid line shows the emission spectrum. Note that the absorption spectrum shown in Figure 64 is dichloro The absorption spectrum measured by placing a romethane solution (0.064 mmol / L) in a quartz cell. Then, the absorption spectrum measured with only dichloromethane placed in a quartz cell was subtracted from the result. It is showing.

[0570] As shown in Figure 64, an organometallic complex [Ir(d1npm)2(dpm)] according to one embodiment of the present invention It has an emission peak at 613 nm, and a reddish-orange emission can be observed from a dichloromethane solution. It was measured. [Examples]

[0571] ≪Synthesis Example 15≫ In this embodiment, an organogold representing one aspect of the present invention, expressed by structural formula (199) of Embodiment 1, is used. Group complex, (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4- Phenylpyrimidinato] Iridium(III) (also known as: bis{2-[5-methyl-6-( 2-methylphenyl)-4-pyrimidinyl-κN3]phenyl-κC}(2,4-penta Ngionath-κ 2 O,O') Iridium(III) (Abbreviation: [Ir(mpmppm)2) A concrete example of the synthesis of (acac) is given. Note that [Ir(mpmppm)2(ac The structure of ac) is shown below.

[0572] [ka]

[0573] Step 1: Synthesis of 4-chloro-5-methyl-6-(2-methylphenyl)pyrimidine > First, 5.0g of 4,6-dichloro-5-methylpyrimidine and 2-methylphenylboronic acid 4.6g, Cesium carbonate 20g, Tricyclohexylphosphine (abbreviation: Cy3P) 15 2.5 mL of % toluene solution, Tris(dibenzylideneacetone)dipalladium(0) (abbreviated) Name: Pd2(dba)3) 0.47g, dioxane 40mL, in a Nasufura with reflux tubing. It was placed in a SCO and the inside was purged with argon. Microwave (2.45 GHz) was then applied to this reaction vessel. The solution was heated by irradiating it with a 50W light for 2 hours. Then, water was added to this solution, and dichloromethane was added. The organic layer was extracted using [method / method]. The obtained organic layer was then mixed with saturated sodium bicarbonate aqueous solution, water, and saturated sodium chloride. The solution was washed with water and dried with magnesium sulfate. The dried solution was filtered. After removing the solvent, the resulting residue is used as the developing solvent for a silica gel column with dichloromethane. The fraction was purified by chromatography and concentrated to obtain 4-chloro-5-methyl -6-(2-methylphenyl)pyrimidine was obtained (white solid, yield 58%). Kuroh wave irradiation was performed using a microwave synthesizer (CEM Discover). See below. The synthesis scheme (q-1) for Step 1 is shown.

[0574] [ka]

[0575] Step 2: Compound 5-methyl-6-(2-methylphenyl)-4-phenylpyrimidine > Next, the 4-chloro-5-methyl-6-(2-methylphenyl) obtained in step 1 above Pyrimidine 1.9g, Phenylboronic acid 1.7g, Sodium carbonate 1.1g, Bis(tri Phenylphosphine) palladium(II) dichloride (abbreviation: Pd(PPh3)2Cl2) 0.105 g, 20 mL of water, and 20 mL of acetonitrile are placed in a round-bottom flask fitted with a reflux condenser. It was placed inside and the interior was purged with argon. Microwaves (2.45 GHz 100) were then applied to this reaction vessel. The solution was heated by irradiating it with W) for 1 hour. Then water was added to this solution and treated with dichloromethane. The organic layer was extracted. The obtained organic layer was then treated with saturated sodium bicarbonate aqueous solution, water, and saturated saline solution. Washed and dried with magnesium sulfate. The dried solution was filtered. The solvent of this solution After removing the residue by distillation, the resulting residue and silica with hexane:ethyl acetate = 9:1 as the developing solvent are used. Purified by gel column chromatography, the resulting fraction was concentrated and 5-methyl -6-(2-methylphenyl)-4-phenylpyrimidine was obtained (white solid, yield 87%). The synthesis scheme (q-2) for step 2 is shown below.

[0576] [ka]

[0577] Step 3: Di-μ-chloro-bis{bis[5-methyl-6-(2-methylphenyl) -4-phenylpyrimidinato]iridium(III)} (abbreviation: [Ir(mpmppm) Synthesis of 2Cl[2] 30 mL of 2-ethoxyethanol, 10 mL of water, and the 5-methyl-6- obtained in step 2 above. (2-methylphenyl)-4-phenylpyrimidine 2.0g, iridium chloride hydrate (I 0.955g of rCl3·H2O (manufactured by Sigma-Aldrich) is placed in a reflux tubing. It was placed in a round-bottom flask, and the flask was purged with argon. Then, microwave (2.45 The mixture was irradiated with 100W (GHz) for 1 hour to allow the reaction to proceed. After removing the solvent by distillation, the resulting residue was... The complex [Ir(mpmppm)2Cl]2 was obtained by suction filtration and washing with tanol (brown). Solid, yield 75%. The synthesis scheme for step 3 (q-3) is shown below.

[0578] [ka]

[0579] <Step 4: (Acetylacetonato)bis[5-methyl-6-(2-methylphenyl) [-4-phenylpyrimidinato]iridium(III)] (abbreviation: [Ir(mpmppm) Synthesis of 2(acac)> 20 mL of 2-ethoxyethanol, the dinuclear complex obtained in step 3 above [Ir(mpmppm 21.8g of 2Cl, 0.360g of acetylacetone, and 1.3g of sodium carbonate are reduced. The sample was placed in a round-bottom flask fitted with a flow tube, and the inside of the flask was purged with argon. After that, microwaves were used. The material was heated by irradiation with (2.45GHz 120W) for 1 hour. After the reaction, the reaction obtained was... Water was added to the mixture, and the aqueous layer was extracted with dichloromethane. The resulting extract was then diluted with saturated saline solution. The mixture was washed, and anhydrous magnesium sulfate was added to the organic layer and dried. The resulting mixture was then filtered naturally. The filtrate was obtained. This filtrate was concentrated to obtain a brown solid. After concentration, this mixture was mixed with dichloromethyl Add approximately 500 mL of tan to this mixture, and add it to Florizil (Wako Pure Chemical Industries, Ltd., catalog). Filtering is performed through a filtration aid consisting of layers of alumina and Celite (item number: 540-00135). The mixture was then concentrated to obtain a red solid. This solid was then mixed with ethyl acetate and hexane. Recrystallization in a mixed solvent yielded an orange powder (yield 57%). Step 4 follows. The synthesis scheme (q-4) is shown below.

[0580] [ka]

[0581] Nuclear magnetic resonance spectroscopy of the obtained orange powder ( 1 The results of the analysis by 1H NMR are shown below. Ta, 1 The 1H NMR chart is shown in Figure 65. From this, it can be seen that in this synthesis example 15, the above One embodiment of the present invention, an organometallic complex [Ir(mpmppm)2] represented by the structural formula (199) It was found that (acac) was obtained.

[0582] 1 H NMR.δ(CDCl3):1.80(s,6H),2.26(br,6H), 2.60(s,6H),5.28(s,1H),6.51(br,2H),6.80(t ,2H),6.90(t,2H),7.39(m,8H),8.00(d,2H),9. 12(s,2H).

[0583] Next, the UV-Vis absorption of the dichloromethane solution of [Ir(mpmppm)2(acac)] The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured. For spectral measurement, a UV-Vis spectrophotometer (V550 model, manufactured by JASCO Corporation) was used. A dichloromethane solution (0.080 mmol / L) was placed in a quartz cell and measured at room temperature. Furthermore, for measuring the emission spectrum, a fluorometer (Hamamatsu Photonics FS920) was used. Using a ) degassed dichloromethane solution (0.080 mmol / L), place it in a quartz cell. Measurements were performed at room temperature. The obtained absorption and emission spectra are shown in Figure 66. The graph shows the wavelength (nm) on the horizontal axis and the absorption intensity (in arbitrary units) and emission intensity (in arbitrary units) on the vertical axis. In addition, two solid lines are shown in Figure 66; the thinner solid line represents the absorption spectrum. The thick solid line shows the emission spectrum. Note that the absorption spectrum shown in Figure 66 is Absorption spectrum of chloromethane solution (0.080 mmol / L) measured in a quartz cell. From this, subtract the absorption spectrum measured by placing only dichloromethane in a quartz cell. It shows the result.

[0584] As shown in Figure 66, one embodiment of the present invention is an organometallic complex [Ir(mpmppm)2(acac )] has an emission peak at 564 nm, and yellow emission is emitted from a dichloromethane solution. It was observed. [Examples]

[0585] ≪Synthesis Example 16≫ In this embodiment, an organogold representing one aspect of the present invention, expressed by structural formula (200) of Embodiment 1, is used. Group complex, tris(4-t-butyl-6-phenylpyrimidinato)iridium(III) Also known as: Tris[2-(6-tert-butyl-4-pyrimidinyl-κN3)phenyl-κ Specific examples of the synthesis of Iridium(III) (abbreviation: [Ir(tBuppm)3]) Let's illustrate with an example. The structure of [Ir(tBuppm)3] is shown below.

[0586] [ka]

[0587] First, take 10g of phenol and the dinuclear complex [Ir(tBuppm) obtained in step 2 of synthesis example 4] 2Cl] 20.97g, HtBuppm obtained in step 1 of synthesis example 4 0.62g, carbonate 1.03 g of lium was placed in a 100 mL three-necked flask, and the flask was purged with argon. The mixture was then heated to 185°C and allowed to react. The resulting residue was subjected to ultrasonic testing with methanol and absorbed. The sample was filtered and washed with ethyl acetate. The resulting solid was dissolved in dichloromethane and then prepared as Celite. The solution was filtered using a filtration aid consisting of layers of alumina and Celite in that order. The solvent was then removed from the solution by distillation. This yielded a yellow powder (yield 17%). The synthesis scheme (r-1) is shown below.

[0588] [ka]

[0589] Nuclear magnetic resonance spectroscopy of the obtained yellow powder ( 1 The results of the analysis by 1H NMR are shown below. Ta, 1 The 1H NMR chart is shown in Figure 67. From this, it can be seen that in this synthesis example 16, the above One embodiment of the present invention, an organometallic complex [Ir(tBuppm)3] represented by the structural formula (200). It was found that ] was obtained.

[0590] 1 H NMR.δ(CDCl3):1.37(s,27H),6.81(d,3H), 6.91-6.97(m,6H),7.77-7.78(m,6H),8.26(s,3 H).

[0591] Next, the ultraviolet-visible absorption spectrum of the dichloromethane solution of [Ir(tBuppm)3] ( ) Below, the absorption spectrum (simply referred to as the "absorption spectrum") and emission spectrum were measured. For the measurement, a UV-Vis spectrophotometer (V550 model, manufactured by JASCO Corporation) was used, and dichlorometh A solution (0.036 mmol / L) was placed in a quartz cell and measured at room temperature. For spectral measurement, a fluorometer (FS920, manufactured by Hamamatsu Photonics Ltd.) was used. Place the aerated dichloromethane solution (0.036 mmol / L) into a quartz cell and measure at room temperature. The measurement results of the obtained absorption and emission spectra are shown in Figure 68. The horizontal axis is Wavelength (nm), the vertical axis represents absorption intensity (arbitrary unit) and emission intensity (arbitrary unit). Also, Figure In graph 68, two solid lines are shown; the thin solid line shows the absorption spectrum, and the thick solid line... The figure shows the emission spectrum. Note that the absorption spectrum shown in Figure 68 is for dichloromethane. From the absorption spectrum measured by placing the solution (0.036 mmol / L) in a quartz cell, the dichroic acid was found. The results shown are obtained by subtracting the absorption spectrum measured using only lolomethane in a quartz cell. ru.

[0592] As shown in Figure 68, the organometallic complex [Ir(tBuppm)3] according to one embodiment of the present invention is 54 It has an emission peak at 0 nm, and yellowish-green emission was observed from a dichloromethane solution. . [Examples]

[0593] ≪Synthesis Example 17≫ In this embodiment, the organic gold is an embodiment of the present invention represented by structural formula (201) of Embodiment 1. Group complex, bis[4-(2,5-dimethylphenyl)-6-(naphthalene-2-yl)pyri [Mijinato] (Dipivaloylmethanato) Iridium(III) (Alternate name: (2,2,6,6- Tetramethyl-3,5-heptanedionato-κ 2 O,O')bis{3-[6-(2,5- Dimethylphenyl)-4-pyrimidinyl-κN3]-2-naphthalenyl-κC}iridium Let's look at specific examples of the synthesis of Mu(III) (abbreviation: [Ir(dmp2npm)2(dpm)]). Let's illustrate this. The structure of [Ir(dmp2npm)2(dpm)] is shown below.

[0594] [ka]

[0595] <Step 1: Synthesis of 4-chloro-6-(naphthalene-2-yl)pyrimidine> First, 5.0g of 4,6-dichloropyrimidine, 11.7g of 2-naphthaleneboronic acid, and carbonate Sodium 7.2g, bis(triphenylphosphine)palladium(II) dichloride ( Abbreviation: Pd(PPh3)2Cl2) 0.29g, water 20mL, acetonitrile 20mL Then, the mixture was placed in a round-bottom flask fitted with a reflux tubing, and the inside was purged with argon. Microphone was placed in this reaction vessel. The material was heated by irradiating it with a low-frequency wave (2.45GHz, 100W) for 60 minutes. Then, further heating was performed. Naphthaleneboronic acid 2.9g, sodium carbonate 1.8g, Pd(PPh3)2Cl2O. Place 0.70g of oak, 5mL of water, and 5mL of acetonitrile into a flask and microwave again (2.4°C). The solution was heated by irradiating it with 5GHz (100W) for 60 minutes. Then water was added to this solution. The organic layer was extracted with dichloromethane. The resulting organic layer was washed with water and magnesium sulfate was used. It was dried. The dried solution was filtered. After removing the solvent from this solution, the remaining The slag was subjected to silica gel column chromatography using hexane:ethyl acetate = 5:1 as the developing solvent. Purified using a fertilizer, the pyrimidine derivative 4-chloro-6-(naphthalene-2-yl)pyrimidine The result was obtained (yellowish-white powder, yield 48%). Microwave irradiation was performed using a microwave synthesis apparatus (C We used EM's Discover. The synthesis scheme (s-1) for step 1 is shown below. show.

[0596] [ka]

[0597] Step 2; 4-(2,5-dimethylphenyl)-6-(naphthalene-2-yl)pyri Synthesis of mites (abbreviated as Hdmp2npm) Next, 3.3g of 4-chloro-6-naphthalene-2-ylpyrimidine obtained in step 1 above. 2,5-dimethylphenylboronic acid 2.1g, sodium carbonate 1.5g, bis(truffle) Phenylphosphine palladium(II) dichloride (abbreviation: Pd(PPh3)2Cl2) Place 0.11 g of the substance, 20 mL of water, and 20 mL of acetonitrile into a round-bottom flask fitted with a reflux condenser. The inside was then purged with argon. A microwave (2.45 GHz 100 W) was then used in this reaction vessel. The device was heated by irradiating it for 60 minutes. Then, 2,5-dimethylphenylboronic acid 1. 0g, sodium carbonate 0.73g, Pd(PPh3)2Cl2 0.050g, water 5mL, Add 5 mL of acetonitrile to the flask and microwave again (2.45 GHz 100 W). The solution was heated by irradiating it for 60 minutes. Then, water was added to this solution and dichloromethane was used. The organic layer was extracted. The obtained organic layer was washed with water and dried with magnesium sulfate. The solution was filtered. After removing the solvent from this solution, the resulting residue was hexane:acetic acid. The pyrimocytes were purified by flash column chromatography using ethyl 2:1 as the developing solvent. The din derivative Hdmp2npm was obtained (pale yellow oil, 97% yield). Step 2 is as follows. The synthesis scheme (s-2) is shown.

[0598] [ka]

[0599] <Step 3; di-μ-chloro-bis{bis[4-(2,5-dimethylphenyl)-6- (Naphthalene-2-yl)pyrimidinato] Iridium(III)} (Abbreviation: [Ir(dm Synthesis of p2npm)2Cl]2) Next, 30 mL of 2-ethoxyethanol, 10 mL of water, and the Hdmp2 obtained in step 2 above. 4.11g of npm and 1.90g of iridium chloride hydrate (IrCl3·H2O) were placed in a reflux tubing. It was placed in a round-bottom flask with a nozzle attached, and the inside of the flask was purged with argon. Then, microwave (2 The mixture was irradiated with 0.45 GHz (100 W) for 1 hour to allow the reaction to proceed. After removing the solvent by distillation, the remaining residue was obtained. The residue was washed by suction filtration with ethanol to obtain the dinuclear complex [Ir(dmp2npm)2Cl]2. (Reddish-brown powder, 97% yield). The synthesis scheme for step 3 (s-3) is shown below.

[0600] [ka]

[0601] Step 4; Bis[4-(2,5-dimethylphenyl)-6-(naphthalene-2-yl) )pyrimidinato] (dipivaloylmethanato) iridium(III) (abbreviation: [Ir(dm (p2npm)2(dpm)) synthesis > Furthermore, 40 mL of 2-ethoxyethanol and the dinuclear complex obtained in step 3 above [Ir(dm [p2npm)2Cl] 21.99g, dipivaloylmethane 0.65g, sodium carbonate 1 0.25g was placed in a round-bottom flask fitted with a reflux tubing, and the flask was purged with argon. Next, it was heated by irradiating it with microwaves (2.45GHz 120W) for 60 minutes. Then, 0.32g of dipivaloylmethane was added to the flask and microwaved again (2.45 GHz). The mixture was heated by irradiation with a 120W light for 60 minutes. The solvent was removed by distillation, and the resulting residue was ethanol. The solid was filtered by suction with gnoll. The resulting solid was washed with water and ethanol. This solid was then hexane. Purification by flash column chromatography using ethyl acetate = 5:1 as the developing solvent. Then, by recrystallizing in a mixed solvent of dichloromethane and hexane, the vermilion powder was obtained. The end was obtained (yield 12%). The synthesis scheme for step 4 (s-4) is shown below.

[0602] [ka]

[0603] Nuclear magnetic resonance spectroscopy of the obtained vermilion powder ( 1 The results of the analysis by 1H NMR are shown below. Ta, 1 The 1H NMR chart is shown in Figure 69. From this, it can be seen that in this synthesis example 17, the above One embodiment of the present invention, an organometallic complex represented by the structural formula (201) [Ir(dmp2npm)] It was found that 2(dpm) was obtained.

[0604] 1 H NMR.δ(CDCl3):0.93(s,18H),2.47(s,6H), 2.56(s,6H),5.63(s,1H),6.90(s,2H),7.14-7. 36(m,10H),7.54(s,2H),7.69(d,2H),8.10(s,2 H), 8.25 (s, 2H), 9.20 (s, 2H).

[0605] Next, the UV-Vis absorption of the dichloromethane solution of [Ir(dmp2npm)2(dpm)] The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured. For spectral measurement, a UV-Vis spectrophotometer (V550 model, manufactured by JASCO Corporation) was used. A dichloromethane solution (0.067 mmol / L) was placed in a quartz cell and measured at room temperature. Furthermore, for measuring the emission spectrum, a fluorometer (Hamamatsu Photonics FS920) was used. Using ), a degassed dichloromethane solution (0.067 mmol / L) is placed in a quartz cell. Measurements were performed at room temperature. The obtained absorption and emission spectra are shown in Figure 70. The graph shows the wavelength (nm) on the horizontal axis and the absorption intensity (in arbitrary units) and emission intensity (in arbitrary units) on the vertical axis. In addition, two solid lines are shown in Figure 70; the thinner solid line represents the absorption spectrum. The thick solid line shows the emission spectrum. Note that the absorption spectrum shown in Figure 70 is Absorption spectrum of chloromethane solution (0.067 mmol / L) measured in a quartz cell. From this, subtract the absorption spectrum measured by placing only dichloromethane in a quartz cell. It shows the result.

[0606] As shown in Figure 70, one embodiment of the present invention is an organometallic complex [Ir(dmp2npm)2(dpm )] has an emission peak at 625 nm, and a red emission is produced from a dichloromethane solution. It was observed. [Examples]

[0607] In this embodiment, a light-emitting element according to one aspect of the present invention will be described with reference to Figure 14. The chemical formulas of the materials used are shown below. Materials already mentioned are omitted.

[0608] [ka]

[0609] The method for fabricating the light-emitting element 6 of this embodiment is shown below.

[0610] (Light-emitting element 6) First, ITSO is deposited on the glass substrate 1100 by sputtering, and the anode is used. A first electrode 1101 capable of performing the function was formed. Its film thickness was 110 nm, and the electrode area was 2 The dimensions were set to mm x 2 mm.

[0611] As a pretreatment for forming light-emitting elements on the substrate 1100, the substrate surface is washed with water, and 2 After firing at 0°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0612] Then, 10 -4 A substrate is introduced into a vacuum deposition apparatus where the internal pressure is reduced to approximately Pa, and then vacuum deposition is performed. After vacuum firing at 170°C for 30 minutes in the heating chamber of the apparatus, the substrate 1100 is subjected to 3 It was allowed to cool for about 0 minutes.

[0613] Next, the first electrode 1101 is shaped so that the surface on which the first electrode 1101 is formed faces downwards. The completed substrate 1100 is fixed to a substrate holder provided inside the vacuum deposition apparatus, 10 -4 P After reducing the pressure to approximately a, BPAFLP and molybdenum oxide (VI) are placed on the first electrode 1101. A hole injection layer 1111 was formed by co-depositing ) and B. The film thickness was set to 40 nm. The ratio of PAFLP to molybdenum oxide is 4:2 by weight (=BPAFLP:molybdenum oxide It was adjusted to become (n).

[0614] Next, BPAFLP is deposited on the hole injection layer 1111 to a thickness of 20 nm, A pore transport layer 1112 was formed.

[0615] Furthermore, 2mDBTPDBq-II, PCBA1BP, and the bis synthesized in Example 12 ( 4,6-Diphenylpyrimidinato)(dipivaloylmethanato) Iridium(III) (abbreviated) Co-deposits [Ir(dppm)2(dpm)]) and places a light-emitting layer 1 on top of the hole transport layer 1112. 113 was formed. Here, 2mDBTPDBq-II, PCBA1BP and [Ir(d The weight ratio of ppm)²(dpm) is 0.8:0.2:0.025 (=2mDBTPDB). The formula was adjusted so that q-II:PCBA1BP:[Ir(dppm)2(dpm)]). Furthermore, the film thickness of the light-emitting layer 1113 was set to 40 nm.

[0616] Next, 2mDBTPDBq-II is deposited on the light-emitting layer 1113 to a thickness of 10 nm. A first electron transport layer 1114a was formed.

[0617] Next, BPhen is deposited on the first electron transport layer 1114a to a thickness of 20 nm. This formed a second electron transport layer 1114b.

[0618] Furthermore, LiF is deposited on the second electron transport layer 1114b to a thickness of 1 nm, forming an electron injection layer. Formed 1115.

[0619] Finally, a 200 nm film of aluminum is used as the second electrode 1103, which functions as the cathode. The light-emitting element 6 of this embodiment was fabricated by depositing a material to a certain thickness.

[0620] In the vapor deposition process described above, resistance heating was used for all deposition steps.

[0621] Table 11 shows the element structure of the light-emitting element 6 obtained as described above.

[0622] [Table 11]

[0623] The light-emitting element 6 is placed in a glove box under a nitrogen atmosphere, so that the light-emitting element 6 is not exposed to the atmosphere. After sealing the device in a suitable manner, the operating characteristics of the light-emitting element 6 were measured. The measurements were taken at room temperature (in an atmosphere maintained at 25°C).

[0624] Figure 71 shows the current density-luminance characteristics of the light-emitting element 6. In Figure 71, the horizontal axis represents the current density (m A / cm 2 The vertical axis represents luminance (cd / m²). 2 ) represents the voltage-luminance characteristics, which are shown in Figure 72. In Figure 72, the horizontal axis represents voltage (V), and the vertical axis represents luminance (cd / m²). 2 ) represents. Also, shine The luminance-current efficiency characteristics are shown in Figure 73. In Figure 73, the horizontal axis represents luminance (cd / m²). 2 ) on the vertical axis This represents the current efficiency (cd / A). Also, the brightness of the light-emitting element 6 is 1100 cd / m². 2 Noto Voltage (V), current density (mA / cm²) 2 ), CIE chromaticity coordinates (x, y), current efficiency (c Table 12 shows the d / A, power efficiency (lm / W), and external quantum efficiency (%).

[0625] [Table 12]

[0626] Furthermore, the emission spectrum when a current of 0.1 mA is passed through the light-emitting element 6 is shown in Figure 74. In Figure 74, the horizontal axis represents wavelength (nm), and the vertical axis represents emission intensity (in arbitrary units). As shown, the emission spectrum of light-emitting element 6 had a peak at 586 nm. Also, Table 12 As shown, 1100 cd / m² 2 The CIE chromaticity coordinates of the light-emitting element 6 at this brightness are (x,y) = (0.55, 0.45). From this result, the light-emitting element 6 is [Ir(dppm) It was found that orange emission originated from 2(dpm).

[0627] As can be seen from Table 12 and Figures 71 to 73, the light-emitting element 6 had good luminous efficiency.

[0628] From the above results, it can be seen that by using an organometallic complex according to one aspect of the present invention as a light-emitting material, high emission It was demonstrated that a device with high optical efficiency can be realized.

[0629] Next, a reliability test was performed on the light-emitting element 6. The results of the reliability test are shown in Figure 75. The vertical axis represents the normalized brightness (%) when the initial brightness is set to 100%, and the horizontal axis represents the drive of the element. This indicates time (h).

[0630] Reliability testing was performed with an initial brightness of 5000 cd / m². 2 Set to the following condition and the current density is constant for the light-emitting element. I drove the 6.

[0631] After 140 hours, the light-emitting element 6 maintained 85% of its initial brightness.

[0632] From the above results, by using an organometallic complex according to one aspect of the present invention as a light-emitting material, reliability It was demonstrated that high-performance elements can be realized. [Examples]

[0633] In this embodiment, a light-emitting element according to one aspect of the present invention will be described with reference to Figure 14. The chemical formulas of the materials used are shown below. Materials already mentioned are omitted.

[0634] [ka]

[0635] The method for fabricating the light-emitting element 7 in this embodiment is shown below.

[0636] (light-emitting element 7) First, ITSO is deposited on the glass substrate 1100 by sputtering, and the anode is used. A first electrode 1101 capable of performing the function was formed. Its film thickness was 110 nm, and the electrode area was 2 The dimensions were set to mm x 2 mm.

[0637] As a pretreatment for forming light-emitting elements on the substrate 1100, the substrate surface is washed with water, and 2 After firing at 0°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0638] Then, 10 -4 A substrate is introduced into a vacuum deposition apparatus where the internal pressure is reduced to approximately Pa, and then vacuum deposition is performed. After vacuum firing at 170°C for 30 minutes in the heating chamber of the apparatus, the substrate 1100 is subjected to 3 It was allowed to cool for about 0 minutes.

[0639] Next, the first electrode 1101 is shaped so that the surface on which the first electrode 1101 is formed faces downwards. The completed substrate 1100 is fixed to a substrate holder provided inside the vacuum deposition apparatus, 10 -4 P After reducing the pressure to approximately 'a', 1,3,5-tri(dibenzothiophene) is applied to the first electrode 1101. (i-4-yl)benzene (abbreviation: DBT3P-II) and molybdenum(VI) oxide are co-evaporated. By applying this, a hole injection layer 1111 was formed. Its film thickness was set to 40 nm, and DBT3P The ratio of -II to molybdenum oxide is 4:2 by weight (=DBT3P-II:molybdenum oxide) It was adjusted to become (n).

[0640] Next, BPAFLP is deposited on the hole injection layer 1111 to a thickness of 20 nm, A pore transport layer 1112 was formed.

[0641] Furthermore, 2mDBTPDBq-II, 4,4'-bis[N-(1-naphthyl)-N-fe [Nylamino]biphenyl (abbreviated as NPB), and (acetylacetone) synthesized in Example 13. Nato)bis[4,6-di(naphthalene-2-yl)pyrimidinato]iridium(III) (abbreviated as [Ir(d2npm)2(acac)]) is co-deposited onto the hole transport layer 1112 A light-emitting layer 1113 was formed. Here, 2mDBTPDBq-II, NPB and [Ir(d The weight ratio of 2npm)2(acac)] is 0.8:0.2:0.025 (=2mDBTP The DBq-II:NPB:[Ir(d2npm)2(acac)]) was adjusted to achieve this. Furthermore, the film thickness of the light-emitting layer 1113 was set to 40 nm.

[0642] Next, 2mDBTPDBq-II is deposited on the light-emitting layer 1113 to a thickness of 10 nm. A first electron transport layer 1114a was formed.

[0643] Next, BPhen is deposited on the first electron transport layer 1114a to a thickness of 20 nm. This formed a second electron transport layer 1114b.

[0644] Furthermore, LiF is deposited on the second electron transport layer 1114b to a thickness of 1 nm, forming an electron injection layer. Formed 1115.

[0645] Finally, a 200 nm film of aluminum is used as the second electrode 1103, which functions as the cathode. The light-emitting element 7 of this embodiment was fabricated by depositing a material to a certain thickness.

[0646] In the vapor deposition process described above, resistance heating was used for all deposition steps.

[0647] Table 13 shows the element structure of the light-emitting element 7 obtained as described above.

[0648] [Table 13]

[0649] The light-emitting element 7 is placed in a glove box under a nitrogen atmosphere, so that the light-emitting element 7 is not exposed to the atmosphere. After sealing the device in a suitable manner, the operating characteristics of the light-emitting element 7 were measured. The measurements were taken at room temperature (in an atmosphere maintained at 25°C).

[0650] Figure 76 shows the current density-luminance characteristics of the light-emitting element 7. In Figure 76, the horizontal axis represents the current density (m A / cm 2 The vertical axis represents luminance (cd / m²). 2 ) represents the voltage-luminance characteristics, which are shown in Figure 77. In Figure 77, the horizontal axis represents voltage (V), and the vertical axis represents luminance (cd / m²). 2 ) represents. Also, shine The luminance-current efficiency characteristics are shown in Figure 78. In Figure 78, the horizontal axis represents luminance (cd / m²). 2 ) on the vertical axis This represents the current efficiency (cd / A). Also, the brightness of the light-emitting element 7 is 1000 cd / m². 2 Noto Voltage (V), current density (mA / cm²) 2 ), CIE chromaticity coordinates (x, y), current efficiency (c Table 14 shows the power efficiency (d / A), power efficiency (lm / W), and external quantum efficiency (%).

[0651] [Table 14]

[0652] Furthermore, Figure 79 shows the emission spectrum when a current of 0.1 mA is passed through the light-emitting element 7. In Figure 79, the horizontal axis represents wavelength (nm), and the vertical axis represents emission intensity (in arbitrary units). As shown, the emission spectrum of light-emitting element 7 had a peak at 616 nm. Also, see Table 14. As shown, 1000 cd / m² 2 The CIE chromaticity coordinates of the light-emitting element 7 at this brightness are (x,y) =(0.64,0.36). From this result, the light-emitting element 7 is [Ir(d2npm It was found that red light emission originating from )2(acac) was obtained.

[0653] As can be seen from Table 14 and Figures 76 to 78, the light-emitting element 7 had good luminous efficiency.

[0654] From the above results, it can be seen that by using an organometallic complex according to one aspect of the present invention as a light-emitting material, high emission It was demonstrated that a device with high optical efficiency can be realized.

[0655] Next, a reliability test was performed on the light-emitting element 7. The results of the reliability test are shown in Figure 80. The vertical axis represents the normalized brightness (%) when the initial brightness is set to 100%, and the horizontal axis represents the drive of the element. This indicates time (h).

[0656] Reliability testing was performed with an initial brightness of 5000 cd / m². 2 Set to the following condition and the current density is constant for the light-emitting element. I drove the 7.

[0657] After 250 hours, the brightness of the light-emitting element 7 remained at 66% of its initial brightness.

[0658] From the above results, by using an organometallic complex according to one aspect of the present invention as a light-emitting material, reliability It was demonstrated that high-performance elements can be realized. [Examples]

[0659] In this embodiment, a light-emitting element according to one aspect of the present invention will be described with reference to Figure 14. The chemical formulas of the materials used are shown below. Materials already mentioned are omitted.

[0660] [ka]

[0661] The method for fabricating the light-emitting element 8 of this embodiment is shown below.

[0662] (light-emitting element 8) The light-emitting element 8 was manufactured in the same manner as the light-emitting element 7 shown in Example 26, except for the light-emitting layer 1113. The following describes the light-emitting layer 1113 of the light-emitting element 8.

[0663] The light-emitting layer 1113 of the light-emitting element 8 is composed of 2mDBTPDBq-II, NPB and Example 17. The result was (acetylacetonato)bis(4,5,6-triphenylpyrimidinato)iridium Formed by co-depositing Mu(III) (abbreviation: [Ir(tppm)2(acac)]) Here, 2mDBTPDBq-II, NPB and [Ir(tppm)2(acac) The weight ratio of ] is 0.8:0.2:0.025 (=2mDBTPDBq-II:NPB:[ The film of the light-emitting layer 1113 was adjusted to Ir(tppm)2(acac). The thickness was set to 40 nm.

[0664] Table 15 shows the element structure of the obtained light-emitting element 8.

[0665] [Table 15]

[0666] The light-emitting element 8 is placed in a glove box under a nitrogen atmosphere, so that the light-emitting element 8 is not exposed to the atmosphere. After sealing the device in a suitable manner, the operating characteristics of the light-emitting element 8 were measured. The measurements were taken at room temperature (in an atmosphere maintained at 25°C).

[0667] Figure 81 shows the current density-luminance characteristics of the light-emitting element 8. In Figure 81, the horizontal axis represents the current density (m A / cm 2 The vertical axis represents luminance (cd / m²). 2 ) represents the voltage-luminance characteristics, which are shown in Figure 82. In Figure 82, the horizontal axis represents voltage (V), and the vertical axis represents luminance (cd / m²). 2 ) represents. Also, shine The luminance-current efficiency characteristics are shown in Figure 83. In Figure 83, the horizontal axis represents luminance (cd / m²). 2 ) on the vertical axis This represents the current efficiency (cd / A). The luminance-external quantum efficiency characteristics are shown in Figure 85. Figure 85 In this graph, the horizontal axis represents luminance (cd / m²). 2 The vertical axis of the graph shows the external quantum efficiency (%).

[0668] Furthermore, the brightness of the light-emitting element 8 is 850 cd / m². 2 Voltage (V), current density (mA / ) at that time cm2 ), CIE chromaticity coordinates (x, y), current efficiency (cd / A), power efficiency (lm / W) The external quantum efficiency (%) is shown in Table 16.

[0669] [Table 16]

[0670] Furthermore, the emission spectrum when a current of 0.1 mA is passed through the light-emitting element 8 is shown in Figure 84. In Figure 84, the horizontal axis represents wavelength (nm), and the vertical axis represents emission intensity (in arbitrary units). As shown, the emission spectrum of light-emitting element 8 had a peak at 593 nm. Also, see Table 16. As shown, 850 cd / m² 2 The CIE chromaticity coordinates of the light-emitting element 8 at this brightness are (x,y) = (0.59, 0.41). From this result, the light-emitting element 8 is [Ir(tppm)2 It was found that orange luminescence originating from (acac) was obtained.

[0671] As can be seen from Figures 81 to 83 and 85, and Table 16, the light-emitting element 8 has a luminous efficiency The results were good. In particular, the light-emitting element 8 produced 850 cd / m². 2 The external quantum efficiency at brightness is 3 It showed an extremely high value of 0%. Note that the light extraction efficiency of organic EL elements is typically 20% to 3%. It is said to be around 0%, so absorption by the upper and lower electrodes must be considered (the above light extraction efficiency is approximately...) If we assume a 10% reduction, the limit of external quantum efficiency should be at most around 25%. However, these results surpass those, and the conventional theoretical value of light extraction efficiency was incorrect. This suggests that the theoretical value of the light extraction efficiency is incorrect. By using an organometallic complex according to one aspect of the present invention, a light-emitting element with unprecedented high efficiency can be obtained. It can be achieved.

[0672] From the above results, it can be seen that by using an organometallic complex according to one aspect of the present invention as a light-emitting material, high emission It was demonstrated that a device with high optical efficiency can be realized.

[0673] Next, a reliability test was performed on the light-emitting element 8. The results of the reliability test are shown in Figure 86. The vertical axis represents the normalized brightness (%) when the initial brightness is set to 100%, and the horizontal axis represents the drive of the element. This indicates time (h).

[0674] Reliability testing was performed with an initial brightness of 5000 cd / m². 2 Set to the following condition and the current density is constant for the light-emitting element. I drove the 8.

[0675] After 340 hours, the light-emitting element 8 maintained 81% of its initial brightness.

[0676] From the above results, by using an organometallic complex according to one aspect of the present invention as a light-emitting material, reliability It was demonstrated that high-performance elements can be realized. [Examples]

[0677] In this embodiment, a light-emitting element according to one aspect of the present invention will be described with reference to Figure 14. The chemical formulas of the materials used are shown below. Materials already mentioned are omitted.

[0678] [ka]

[0679] The method for fabricating the light-emitting element 9 in this embodiment is shown below.

[0680] (light-emitting element 9) The light-emitting element 9 was manufactured in the same manner as the light-emitting element 7 shown in Example 26, except for the light-emitting layer 1113. The following describes the light-emitting layer 1113 of the light-emitting element 9.

[0681] The light-emitting layer 1113 of the light-emitting element 9 is 2mDBTPDBq-II, PCBA1BP and the example. (Tris(4-methyl-6-phenylpyrimidinato)iridium(III) synthesized in 18 It was formed by co-depositing ) (abbreviation: [Ir(mppm)3]). Here, 2mDBT The weight ratio of PDBq-II, PCBA1BP, and [Ir(mppm)3] is 0.8:0. 2:0.05(=2mDBTPDBq-II:PCBA1BP:[Ir(mppm)3] The settings were adjusted to achieve the desired result. The film thickness of the light-emitting layer 1113 was set to 40 nm.

[0682] Table 17 shows the element structure of the obtained light-emitting element 9.

[0683] [Table 17]

[0684] The light-emitting element 9 is placed in a glove box under a nitrogen atmosphere, so that the light-emitting element 9 is not exposed to the atmosphere. After sealing the device in a suitable manner, the operating characteristics of the light-emitting element 9 were measured. The measurements were taken at room temperature (in an atmosphere maintained at 25°C).

[0685] Figure 87 shows the current density-luminance characteristics of the light-emitting element 9. In Figure 87, the horizontal axis represents the current density (m A / cm 2 The vertical axis represents luminance (cd / m²). 2 ) represents the voltage-luminance characteristics, which are shown in Figure 88. In Figure 88, the horizontal axis represents voltage (V), and the vertical axis represents luminance (cd / m²). 2 ) represents. Also, shine The luminance-current efficiency characteristics are shown in Figure 89. In Figure 89, the horizontal axis represents luminance (cd / m²). 2 ) on the vertical axis This represents the current efficiency (cd / A). Also, the brightness of the light-emitting element 9 is 770 cd / m². 2 at that time Voltage (V), current density (mA / cm²) 2 ), CIE chromaticity coordinates (x, y), current efficiency (cd) Table 18 shows the power efficiency (lm / W), power efficiency (lm / W), and external quantum efficiency (%).

[0686] [Table 18]

[0687] Furthermore, Figure 90 shows the emission spectrum when a current of 0.1 mA is passed through the light-emitting element 9. In Figure 90, the horizontal axis represents wavelength (nm), and the vertical axis represents emission intensity (in arbitrary units). As shown, the emission spectrum of the light-emitting element 9 had a peak at 536 nm. Also, see Table 18. As shown, 770 cd / m² 2 The CIE chromaticity coordinates of the light-emitting element 9 at this brightness are (x,y) = (0.41, 0.58). From this result, the light-emitting element 9 is [Ir(mppm)3 It was found that a yellowish-green emission originating from [ ] was obtained.

[0688] As can be seen from Table 18 and Figures 87 to 89, the light-emitting element 9 had good luminous efficiency.

[0689] From the above results, it can be seen that by using an organometallic complex according to one aspect of the present invention as a light-emitting material, high emission It was demonstrated that a device with high optical efficiency can be realized.

[0690] Next, a reliability test was performed on the light-emitting element 9. The results of the reliability test are shown in Figure 91. The vertical axis represents the normalized brightness (%) when the initial brightness is set to 100%, and the horizontal axis represents the drive of the element. This indicates time (h).

[0691] Reliability testing was performed with an initial brightness of 5000 cd / m². 2 Set to the following condition and the current density is constant for the light-emitting element. I drove the 9.

[0692] After 360 hours, the brightness of the light-emitting element 9 remained at 65% of its initial brightness.

[0693] From the above results, by using an organometallic complex according to one aspect of the present invention as a light-emitting material, reliability It was demonstrated that high-performance elements can be realized. [Examples]

[0694] In this embodiment, a light-emitting element according to one aspect of the present invention will be described with reference to Figure 14. The chemical formulas of the materials used are shown below. Materials already mentioned are omitted.

[0695] [ka]

[0696] The method for manufacturing the light-emitting element 10 of this embodiment is shown below.

[0697] (light-emitting element 10) The light-emitting element 10 was manufactured in the same manner as the light-emitting element 7 shown in Example 26, except for the light-emitting layer 1113. The following describes the light-emitting layer 1113 of the light-emitting element 10.

[0698] The light-emitting layer 1113 of the light-emitting element 10 is 2mDBTPDBq-II, NPB and in Example 19 Synthesized bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmeth Co-depositing sodium iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)]) This was formed by the following: Here, 2mDBTPDBq-II, NPB and [Ir(5mdp The weight ratio of pm)2(dpm) is 0.8:0.2:0.05 (=2mDBTPDBq- II:NPB:[Ir(5mdppm)2(dpm)]) was adjusted. The film thickness of the li...

Claims

[Claim 1] A light-emitting device having a light-emitting element and a transistor that controls the driving of the light-emitting element, The light-emitting element comprises a pair of electrodes and a light-emitting layer. The light-emitting layer comprises an organometallic complex having a structure represented by general formula (G1), a first organic compound, and a second organic compound. The triplet excitation energy of the first organic compound is greater than the triplet excitation energy of the organometallic complex. The triplet excitation energy of the second organic compound is greater than that of the organometallic complex. The transistor is a light-emitting device having an oxide semiconductor. 【Chemistry 1】 (In the formula, R １ R represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms. ２ R represents hydrogen, a substituted or unsubstituted C1-C4 alkyl group, or a substituted or unsubstituted phenyl group. ３ Ar represents hydrogen, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. １ (This represents a substituted or unsubstituted arylene group with 6 to 10 carbon atoms.)

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