Organometallic complex

Abstract

To provide a novel substance that can emit phosphorescence, or a novel substance with high emission efficiency.SOLUTION: The invention provides an organometallic complex in which a 4-arylpyrimidine derivative is a ligand and iridium is a central metal, and specifically, an organometallic complex having a structure represented by the general formula (G1). In the general formula (G1), R1 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, R2 represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted phenyl group, R3 represents hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and Ar1 represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to an organometallic complex, in particular, an organometallic complex capable of converting a triplet excited state into luminescence. The present invention also relates to a light-emitting element, a light-emitting device, an electronic device, and a lighting device using the organometallic complex. . [Background technology]

[0002] In recent years, there has been active development of light-emitting devices that use luminescent organic and inorganic compounds as luminescent materials. In particular, light-emitting elements called EL (Electroluminescence) elements The structure of the device is simple, consisting of a light-emitting layer containing a light-emitting material between electrodes, and is thin and lightweight. Due to its characteristics of being able to operate at low DC voltage, it can respond quickly to input signals, and is These light-emitting devices are attracting attention as the next generation of flat panel display elements. Displays using these devices have the characteristics of excellent contrast and image quality, as well as a wide viewing angle. Furthermore, since these light emitting elements are surface light sources, they are suitable for use as backlights for liquid crystal displays. Applications as a light source for lighting and other purposes are also being considered.

[0003] When the light-emitting substance is a light-emitting organic compound, the light-emitting mechanism of the light-emitting element is a carrier injection type. That is, by applying a voltage to a light-emitting layer sandwiched between electrodes, the light injected from the electrodes is The electrons and holes recombine to excite the luminescent material, which then returns to the ground state. The excited state is classified into two types: singlet excited state (S * ) and triplet excitation Status(T * ) is possible. The statistical generation ratio in the light-emitting element is S * :T * It is believed that the ratio is 1:3.

[0004] Light-emitting organic compounds usually have a singlet ground state. Therefore, the singlet excited state (S * ) is called fluorescence because it is an electron transition between the same multiplicities. term excited state (T * ) is called phosphorescence because it is an electron transition between different multiplicities. Here, a compound that emits fluorescence (hereinafter referred to as a fluorescent compound) is usually phosphorus at room temperature. No light is observed, only fluorescence is observed. The theoretical limit of the internal quantum efficiency (the ratio of photons generated to the injected carriers) is , S * :T * It is said to be 25% based on the ratio being 1:3.

[0005] On the other hand, if phosphorescent compounds are used, the internal quantum efficiency can theoretically reach 100%. This means that the luminescence efficiency is four times higher than that of fluorescent compounds. In order to realize light-emitting devices that use phosphorescent compounds, the development of light-emitting devices using phosphorescent compounds has been actively pursued in recent years. In particular, iridium and other phosphorescent compounds are popular due to their high phosphorescence quantum yield. Organometallic complexes with iridium as the central metal have been attracting attention. For example, Patent Document 1 describes Organometallic complexes having a central metal have been disclosed as phosphorescent materials.

[0006] The advantage of using a highly efficient light-emitting element is that the power consumption of an electronic device using the light-emitting element is reduced. In recent times, when energy issues have become a hot topic, power consumption is This is a very important factor as it is becoming a major factor influencing consumer purchasing trends. It is raw. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] WO 00 / 70655 Summary of the Invention [Problem to be solved by the invention]

[0008] An object of one embodiment of the present invention is to provide a novel substance capable of emitting phosphorescence. Another object is to provide a novel substance having high luminous efficiency. It is an object of the present invention to provide a light-emitting element, a light-emitting device, an electronic device, or a lighting device using the same. do.

[0009] Alternatively, a light-emitting element, a light-emitting device, an electronic device, or a lighting device with high luminous efficiency can be provided. Another object is to provide a light-emitting element, a light-emitting device, an electronic device, or a lighting device having high reliability. Another object of the present invention is to provide a light-emitting element, a light-emitting device, It is an object of the present invention to provide an electronic device or a lighting device. [Means for solving the problem]

[0010] One aspect of the present invention is a 4-arylpyrimidine derivative as a ligand and iridium as a central metal. Another embodiment of the present invention is an organometallic complex having a 4-aryl group having a substituent at the 6-position. Arylpyrimidine derivatives (6-arylpyrimidines with a substituent at the 4-position, depending on the type of substituent) The ligand is iridium, which is sometimes called a iridinium derivative. Further, one embodiment of the present invention is a metal complex having an alkyl group or an aryl group at the 6-position. 4-arylpyrimidine derivatives (depending on the type of substituent, an alkyl group or an aryl group may be present at the 4-position) The ligand is 6-arylpyrimidine derivatives having an aryl group. In particular, the 4-arylpyrimidine derivative is an organometallic complex having iridium as the central metal. The conductor is preferably a 4,6-diphenylpyrimidine derivative.

[0011] A specific embodiment of the present invention is an organometallic complex having a structure represented by general formula (G1). do.

[0012] [ka]

[0013] In the formula, R 1 is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted R represents an aryl group having 6 to 10 carbon atoms. 2 is hydrogen, substituted or unsubstituted carbon atom number 1 R represents an alkyl group having a molecular weight of 1 to 4, or a substituted or unsubstituted phenyl group; 3 is hydrogen or a substituent. represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms; Ar 1 represents a substituted or unsubstituted carbon atom. Represents an arylene group having 6 to 10 carbon atoms.

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

[0015] [ka]

[0016] In the formula, R 1 is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted R represents an aryl group having 6 to 10 carbon atoms. 2is hydrogen, substituted or unsubstituted carbon atom number 1 R represents an alkyl group having a molecular weight of 1 to 4, or a substituted or unsubstituted phenyl group; 3 is hydrogen or a substituent. R represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. 4 ~R 7 are each independently Hydrogen, substituted or unsubstituted alkyl groups having 1 to 4 carbon atoms, substituted or unsubstituted alkyl groups having 1 alkoxy group having 1 to 4 carbon atoms, substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, halogen group a substituted or unsubstituted haloalkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted Represents an aryl group having 6 to 10 carbon atoms.

[0017] Another embodiment 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 a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or represents an unsubstituted phenyl group, R 3 is hydrogen or a substituted or unsubstituted C1-4 represents an alkyl group, R 4 ~R 12 each independently represents hydrogen, a substituted or unsubstituted carbon atom, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 4 carbon atoms, is an unsubstituted alkylthio group having 1 to 4 carbon atoms, a halogen group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.

[0020] Another embodiment of the present invention is an organometallic complex represented by General Formula (G4).

[0021] [ka]

[0022] In the formula, L represents a monoanionic ligand. 1 is a substituted or unsubstituted carbon represents an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, R 2 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted R represents a substituted phenyl group; 3 is hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. represents an alkyl group, and Ar 1 represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.

[0023] One embodiment of the present invention is an organometallic complex represented by General Formula (G5).

[0024] [ka]

[0025] In the formula, L represents a monoanionic ligand. 1 is a substituted or unsubstituted carbon atom number 1 to R represents an alkyl group having 6 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; 2 teeth , hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted fluorine atom. R represents a phenyl group. 3 represents hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. Represents R 4 ~R 7 each independently represents a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms; alkyl group, substituted or unsubstituted alkoxy group having 1 to 4 carbon atoms, substituted or unsubstituted carbon an alkylthio group having 1 to 4 carbon atoms, a halogen group, or a substituted or unsubstituted haloalloy group having 1 to 4 carbon atoms; a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.

[0026] One embodiment of the present invention is an organometallic complex represented by General Formula (G6).

[0027] [ka]

[0028] In the formula, L represents a monoanionic ligand. 2 is hydrogen, substituted or unsubstituted carbon R represents an alkyl group having a number of 1 to 4, or a substituted or unsubstituted phenyl group; 3 is hydrogen, or represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, R 4 ~R 12 are each In particular, hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted carbon atom, an alkoxy group having 1 to 4 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, a halo a substituted or unsubstituted haloalkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted represents an aryl group having 6 to 10 carbon atoms.

[0029] Another embodiment of the present invention is an organometallic complex represented by general formula (G7).

[0030] [ka]

[0031] In the formula, R 1 is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted R represents an aryl group having 6 to 10 carbon atoms. 2 is hydrogen, substituted or unsubstituted carbon atom number 1 R represents an alkyl group having a molecular weight of 1 to 4, or a substituted or unsubstituted phenyl group; 3 is hydrogen or a substituent. represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms; Ar 1 represents a substituted or unsubstituted carbon atom. Represents an arylene group having 6 to 10 carbon atoms.

[0032] One embodiment of the present invention is an organometallic complex represented by General Formula (G8).

[0033] [ka]

[0034] In the formula, R 1 is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted R represents an aryl group having 6 to 10 carbon atoms. 2 is hydrogen, substituted or unsubstituted carbon atom number 1 R represents an alkyl group having a molecular weight of 1 to 4, or a substituted or unsubstituted phenyl group; 3 is hydrogen or a substituent. R represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. 4 ~R 7 are each independently Hydrogen, substituted or unsubstituted alkyl groups having 1 to 4 carbon atoms, substituted or unsubstituted alkyl groups having 1 alkoxy group having 1 to 4 carbon atoms, substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, halogen group a substituted or unsubstituted haloalkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted Represents an aryl group having 6 to 10 carbon atoms.

[0035] One embodiment of the present invention is an organometallic complex represented by General Formula (G9).

[0036] [ka]

[0037] In the formula, R 2 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or represents an unsubstituted phenyl group, R 3 is hydrogen or a substituted or unsubstituted C1-4 represents an alkyl group, R 4 ~R 12 each independently represents hydrogen, a substituted or unsubstituted carbon atom, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 4 carbon atoms, is an unsubstituted alkylthio group having 1 to 4 carbon atoms, a halogen group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.

[0038] In the organometallic complexes represented by the general formulas (G4) to (G6), monoanionic coordination The compound is a monoanionic bidentate chelating ligand having a beta-diketone structure, carboxyl Monoanionic bidentate chelating ligands having a phenolic hydroxyl group. anionic bidentate chelating ligand, or monoanionic where both coordination elements are nitrogen In particular, a monoaromatic chelate ligand having a beta-diketone structure is preferably used. Anionic bidentate chelating ligands are preferred.

[0039] The monoanionic ligand is any one of the general formulas (L1) to (L7). is preferred.

[0040] [ka]

[0041] In the formula, R 71 ~R 109 are each independently hydrogen or a substituted or unsubstituted group having 1 to 4 carbon atoms. an alkyl group, a halogen group, a vinyl group, a substituted or unsubstituted haloalkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 4 carbon atoms. Represents an alkylthio group having 1 to 4 prime numbers. 1 ~A 3 are each independently nitrogen, hydrogen sp that binds to 2 Hybridized carbon or sp bonded to the substituent R 2 represents carbon, and the substituent R an alkyl group having 1 to 4 carbon atoms, a halogen group, a haloalkyl group having 1 to 4 carbon atoms, or a phenyl group Represents a group.

[0042] Another embodiment of the present invention is a light-emitting element having the above-described organometallic complex between a pair of electrodes. In particular, it is preferable that the light-emitting layer contains the organometallic complex.

[0043] The scope of the present invention also includes light-emitting devices, electronic devices, and lighting devices using the light-emitting elements. In this specification, the term "light-emitting device" includes an image display device and a light source. , a connector on the panel, such as FPC (Flexible Printed Circuit it) or TAB (Tape Automated Bonding) tape or is a module equipped with a TCP (Tape Carrier Package), A module with a printed wiring board on the end of TAB tape or TCP, or a light-emitting element with C Module with IC (Integrated Circuit) directly mounted using OG (Chip On Glass) method All modules are considered to be included in the light-emitting device. Effect of the Invention

[0044] According to one embodiment of the present invention, a novel substance capable of emitting phosphorescence can be provided. Alternatively, a novel substance having high luminous efficiency can be provided. A light-emitting element, a light-emitting device, an electronic device, or a lighting device can be provided.

[0045] Alternatively, a light-emitting element, a light-emitting device, an electronic device, or a lighting device with high luminous efficiency can be provided. Alternatively, a light-emitting element, a light-emitting device, an electronic device, or a lighting device with high reliability can be provided. Alternatively, a light-emitting element, a light-emitting device, an electronic device, or can provide a lighting device. [Brief description of the drawings]

[0046] [Figure 1] 1A to 1C illustrate a light-emitting element of one embodiment of the present invention. [Diagram 2] FIG. 1 illustrates a passive matrix light-emitting device. [Diagram 3] FIG. 1 illustrates a passive matrix light-emitting device. [Figure 4] FIG. 1 illustrates an active matrix light-emitting device. [Diagram 5] 1A to 1C are diagrams illustrating electronic devices. [Figure 6] 1A and 1B are diagrams illustrating a lighting device. [Figure 7] 1A and 1B are diagrams illustrating a lighting device. [Figure 8] 1H NMR chart of the organometallic complex shown in structural formula (100). [Figure 9] UV-visible absorption and emission spectra 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-visible absorption and emission spectra 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-visible absorption and emission spectra of the organometallic complex shown in structural formula (152). [Figure 14] 1A to 1C are diagrams illustrating a light-emitting element according to an embodiment; [Figure 15] FIG. 13 shows current density-luminance characteristics of the light-emitting element 1. [Figure 16] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 1. [Figure 17] FIG. 13 shows luminance vs. current efficiency characteristics of the light-emitting element 1. [Figure 18] FIG. 2 shows an emission spectrum of the light-emitting element 1. [Figure 19] FIG. 13 shows the results of a reliability test of the light-emitting element 1. [Figure 20] FIG. 13 shows current density-luminance characteristics of the light-emitting element 2. [Figure 21] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 2. [Figure 22] FIG. 13 shows luminance vs. current efficiency characteristics of Light-emitting Element 2. [Figure 23] FIG. 2 shows an emission spectrum of the light-emitting element 2. [Figure 24] FIG. 13 shows the results of a reliability test of the light-emitting element 2. [Diagram 25] FIG. 13 shows luminance vs. external quantum efficiency characteristics of the light-emitting element 2. [Figure 26] FIG. 13 shows current density-luminance characteristics of the light-emitting element 3. [Figure 27] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 3. [Figure 28] FIG. 13 shows luminance vs. current efficiency characteristics of the light-emitting element 3. [Figure 29] FIG. 2 shows an emission spectrum of the light-emitting element 3. [Diagram 30] FIG. 13 shows the results of a reliability test of the light-emitting element 3. [Diagram 31] FIG. 13 shows luminance vs. external quantum efficiency characteristics of the light-emitting element 3. [Diagram 32] 1H NMR chart of the organometallic complex shown in structural formula (190). [Diagram 33] UV-visible absorption and emission spectra of the organometallic complex shown in structural formula (190). [Diagram 34]FIG. 13 shows current density-luminance characteristics of the light-emitting element 4. [Diagram 35] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 4. [Diagram 36] FIG. 13 shows luminance vs. current efficiency characteristics of the light-emitting element 4. [Figure 37] FIG. 13 shows an emission spectrum of the light-emitting element 4. [Figure 38] 1A to 1C are diagrams illustrating a light-emitting element according to an embodiment; [Figure 39] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 5. [Diagram 40] FIG. 13 shows luminance vs. power efficiency characteristics of the light-emitting element 5. [Diagram 41] FIG. 13 shows luminance vs. external quantum efficiency characteristics of the light-emitting element 5. [Diagram 42] FIG. 4 shows an emission spectrum of the light-emitting element 5. [Diagram 43] FIG. 13 shows the results of a reliability test of the light-emitting element 5. [Diagram 44] 13 shows the results of an accelerated luminance test of the light-emitting element 5. FIG. [Diagram 45] 1H NMR chart of the organometallic complex shown in structural formula (101). [Figure 46] UV-visible absorption and emission spectra 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-visible absorption and emission spectra 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-visible absorption and emission spectra 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-visible absorption and emission spectra of the organometallic complex shown in structural formula (119). [Diagram 53]1H NMR chart of the organometallic complex shown in structural formula (123). [Figure 54] UV-visible absorption and emission spectra 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-visible absorption and emission spectra 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-visible absorption and emission spectra 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-visible absorption and emission spectra 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-visible absorption and emission spectra 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-visible absorption and emission spectra 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-visible absorption and emission spectra 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-visible absorption and emission spectra 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] UV-visible absorption spectrum and emission spectrum of the organometallic complex shown in structural formula (201). [Figure 71] FIG. 13 is a graph showing current density-luminance characteristics of the light-emitting element 6. [Figure 72] FIG. 13 is a graph showing voltage-luminance characteristics of the light-emitting element 6. [Figure 73] FIG. 13 shows luminance vs. current efficiency characteristics of the light-emitting element 6. [Figure 74] FIG. 2 shows an emission spectrum of the light-emitting element 6. [Figure 75] FIG. 13 shows the results of a reliability test of the light-emitting element 6. [Figure 76] FIG. 13 is a graph showing current density-luminance characteristics of the light-emitting element 7. [Figure 77] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 7. [Figure 78] FIG. 13 shows luminance vs. current efficiency characteristics of the light-emitting element 7. [Figure 79] FIG. 4 shows an emission spectrum of the light-emitting element 7. [Figure 80] FIG. 13 shows the results of a reliability test of the light-emitting element 7. [Figure 81] FIG. 13 is a graph showing current density-luminance characteristics of the light-emitting element 8. [Figure 82] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 8. [Figure 83] FIG. 13 shows luminance vs. current efficiency characteristics of the light-emitting element 8. [Figure 84] FIG. 2 shows an emission spectrum of the light-emitting element 8. [Figure 85] FIG. 13 is a graph showing luminance vs. external quantum efficiency characteristics of the light-emitting element 8. [Figure 86] FIG. 13 shows the results of a reliability test of the light-emitting element 8. [Figure 87] FIG. 13 is a graph showing current density-luminance characteristics of the light-emitting element 9. [Figure 88] FIG. 13 is a graph showing voltage-luminance characteristics of the light-emitting element 9. [Figure 89] FIG. 13 shows luminance vs. current efficiency characteristics of the light-emitting element 9. [Figure 90] FIG. 2 shows an emission spectrum of the light-emitting element 9. [Figure 91]FIG. 13 shows the results of a reliability test of the light-emitting element 9. [Figure 92] FIG. 13 shows current density-luminance characteristics of the light-emitting element 10. [Figure 93] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 10. [Figure 94] FIG. 13 shows luminance vs. current efficiency characteristics of the light-emitting element 10. [Figure 95] FIG. 2 shows an emission spectrum of the light-emitting element 10. [Figure 96] FIG. 13 is a graph showing luminance vs. external quantum efficiency characteristics of the light-emitting element 10. [Figure 97] 13 shows the results of a reliability test of the light-emitting element 10. FIG. [Figure 98] FIG. 13 shows current density-luminance characteristics of the light-emitting element 11. [Figure 99] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 11. [Figure 100] FIG. 13 shows luminance vs. current efficiency characteristics of the light-emitting element 11. [Figure 101] FIG. 2 shows an emission spectrum of the light-emitting element 11. [Figure 102] FIG. 13 is a graph showing luminance vs. external quantum efficiency characteristics of the light-emitting element 11. [Figure 103] FIG. 13 shows the results of a reliability test of the light-emitting element 11. [Figure 104] FIG. 13 shows current density-luminance characteristics of the light-emitting element 12. [Figure 105] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 12. [Figure 106] FIG. 13 shows luminance vs. current efficiency characteristics of the light-emitting element 12. [Figure 107] FIG. 2 shows an emission spectrum of the light-emitting element 12. [Figure 108] FIG. 13 shows the results of a reliability test of the light-emitting element 12. [Figure 109] FIG. 13 shows current density-luminance characteristics of the light-emitting element 13. [Figure 110] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 13. [Figure 111] FIG. 13 shows luminance vs. current efficiency characteristics of the light-emitting element 13. [Figure 112] FIG. 2 shows an emission spectrum of the light-emitting element 13. [Figure 113] FIG. 13 is a graph showing luminance vs. external quantum efficiency characteristics of the light-emitting element 13. [Fig. 114] FIG. 13 shows the results of a reliability test of the light-emitting element 13. [Figure 115] FIG. 13 is a graph showing current density-luminance characteristics of the light-emitting element 14. [Fig. 116] FIG. 13 is a graph showing voltage-luminance characteristics of the light-emitting element 14. [Fig. 117] FIG. 13 shows luminance vs. current efficiency characteristics of the light-emitting element 14. [Fig. 118] FIG. 2 shows an emission spectrum of the light-emitting element 14. [Figure 119] FIG. 13 shows the results of a reliability test of the light-emitting element 14. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0047] The embodiment will be described in detail with reference to the drawings. However, the present invention is not limited to the following description. The present invention is not limited to the above embodiment, and various changes and modifications may be made in the form and details without departing from the spirit and scope of the present invention. It will be easily understood by those skilled in the art that the above-mentioned invention can be obtained by the following embodiments. The present invention should not be construed as being limited to the contents described below. The same reference numerals are used in different drawings to indicate the same parts or parts having similar functions. A repeated explanation will be omitted.

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

[0049] One aspect of the present invention is a 4-arylpyrimidine derivative as a ligand and iridium as a central metal. Another embodiment of the present invention is an organometallic complex having a 4-aryl group having a substituent at the 6-position. Arylpyrimidine derivatives (6-arylpyrimidines with a substituent at the 4-position, depending on the type of substituent) The ligand is iridium, which is sometimes called a iridinium derivative. Further, one embodiment of the present invention is a metal complex having an alkyl group or an aryl group at the 6-position. 4-arylpyrimidine derivatives (depending on the type of substituent, an alkyl group or an aryl group may be present at the 4-position) The ligand is 6-arylpyrimidine derivatives having an aryl group. In particular, the 4-arylpyrimidine derivative is an organometallic complex having iridium as the central metal. The conductor is preferably a 4,6-diphenylpyrimidine derivative.

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

[0051] [ka]

[0052] In general formula (G1), R 1 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. or an unsubstituted aryl group having 6 to 10 carbon atoms; R 2 is hydrogen, substituted or unsubstituted. R represents a substituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted phenyl group; 3 teeth, represents hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms; Ar 1 is replaced or It represents an unsubstituted arylene group having 6 to 10 carbon atoms.

[0053] Here, Ar 1 Specific examples of the alkyl group include a phenylene group, an alkyl group having 1 to 4 carbon atoms and one or more substituents. substituted phenylene groups; phenylene groups 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, aryl group having 6 to 10 carbon atoms a phenylene group substituted with one or more alkyl groups; a phenylene group substituted with one or more halogen groups; Phenylene group substituted with one or more haloalkyl groups having 1 to 4 carbon atoms, substituted or unsubstituted Examples of the alkyl group include a biphenyl-diyl group and a substituted or unsubstituted naphthalene-diyl group.

[0054] Also, R 1 ~R 3 Specific examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, and the like. butyl, sec-butyl, isobutyl, tetrabutyl, tetradecyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tetradecyl, tetradecyl Specific examples of the aryl group having 6 to 10 carbon atoms include phenyl, a phenyl group substituted with one or more alkyl groups having 1 to 4 carbon atoms; a phenyl group substituted with one or more thio groups, Phenyl group, phenyl group substituted with one or more aryl groups having 6 to 10 carbon atoms, halogen groups Phenyl group substituted with one or more haloalkyl groups having 1 to 4 carbon atoms Examples include an aryl group and a naphthalene-yl group.

[0055] Also, R 1 In the above, the alkyl group having 1 to 4 carbon atoms is preferably an alkyl group having 2 or more carbon atoms. An alkyl group having two or more carbon atoms suppresses intermolecular interactions due to steric hindrance. Therefore, side reactions in the synthesis reaction of the organometallic complex according to one embodiment of the present invention are suppressed, and the yield is improved. The rate will improve.

[0056] Taking this into account, R 1 Examples of the alkyl group having 1 to 4 carbon atoms include an ethyl group, a propyl group, and the like. butyl, sec-butyl, isobutyl, tert-butyl The group is more preferred.

[0057] The above Ar 1 is a substituted or unsubstituted phenylene group, which is preferable because synthesis is easy. Therefore, one embodiment of the present invention is an organometallic complex having a structure represented by general formula (G2): It is.

[0058] [ka]

[0059] In general formula (G2), R 1 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. or an unsubstituted aryl group having 6 to 10 carbon atoms; R 2 is hydrogen, substituted or unsubstituted. R represents a substituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted phenyl group; 3 teeth, represents hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms; R 4 ~R 7 Is that each independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted substituted alkoxy group having 1 to 4 carbon atoms, 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 It represents an unsubstituted aryl group having 6 to 10 carbon atoms.

[0060] Here, R 1 ~R 3 Specific examples of the formula (G1) include those shown in general formula (G2). , R 4 ~R 7 Specific examples of each independently include hydrogen, a methyl group, an ethyl group, and a propyl group. group, isopropyl group, butyl group, sec-butyl group, isobutyl group, tert-butyl group , methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, sec-butoxy group butoxy group, isobutoxy group, tert-butoxy group, methylsulfinyl group, ethylsulf sulfinyl group, propylsulfinyl group, isopropylsulfinyl group, butylsulfinyl group isobutylsulfinyl group, sec-butylsulfinyl group, tert-butylsulfinyl group, Rufinyl group, fluoro group, fluoromethyl group, difluoromethyl group, trifluoromethyl group methyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, 2, 2,2-trifluoroethyl group, 3,3,3-trifluoropropyl group, 1,1,1,3 ,3,3-hexafluoroisopropyl group, phenyl group, alkyl group having 1 to 4 carbon atoms or more substituted phenyl group, or a phenyl group 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, an aryl group having 6 to 10 carbon atoms a phenyl group substituted with one or more halogen groups, a phenyl group substituted with one or more halogen groups, A phenyl group substituted with one or more haloalkyl groups having 1 to 4 groups, a substituted or unsubstituted naphtha group, Examples thereof include a lenyl group.

[0061] In one embodiment 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): As shown in the structure represented by general formula (G3), it is an organometallic complex having a pyrimidine structure. The phenyl group is located at the 6-position of the phenyl skeleton (i.e., 1 is a substituted or unsubstituted phenyl group In addition, when the organic metal complex is applied to a light-emitting device, the yield of the organic metal complex is improved. In particular, it is preferable because it exhibits extremely high luminous efficiency.

[0062] [ka]

[0063] In general formula (G3), R 2 is hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or represents a substituted or unsubstituted phenyl group, R 3 is hydrogen or a substituted or unsubstituted carbon atom. Represents an alkyl group having 1 to 4 prime numbers, R 4 ~R 12 are each independently hydrogen, a substituent or Unsubstituted alkyl group having 1 to 4 carbon atoms, 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 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; It represents a aryl group.

[0064] Here, R 2 ~R 7 Specific examples of the general formulae (G1) and (G2) are as follows: Also, R 8 ~R 12 Specific examples of each independently include hydrogen, a methyl group, and ethyl. butyl, sec-butyl, isobutyl, tetrabutyl, tetradecyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tetradecyl, tetradecyl rt-Butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy group, sec-butoxy group, isobutoxy group, tert-butoxy group, methylsulfinyl group group, ethylsulfinyl group, propylsulfinyl group, isopropylsulfinyl group, Thilsulfinyl group, isobutylsulfinyl group, sec-butylsulfinyl group, te rt-Butylsulfinyl group, fluoro group, fluoromethyl group, difluoromethyl group, th Trifluoromethyl 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, C1-4 Phenyl group substituted with one or more alkyl groups, alkoxy group having 1 to 4 carbon atoms phenyl groups substituted with one or more alkylthio groups having 1 to 4 carbon atoms; Phenyl group substituted with one or more aryl groups having 6 to 10 carbon atoms, a phenyl group, a phenyl group substituted with one or more haloalkyl groups having 1 to 4 carbon atoms, An example is an unsubstituted naphthalene-yl group.

[0065] Another embodiment of the present invention is an organometallic complex represented by General Formula (G4).

[0066] [ka]

[0067] In the general formula (G4), L represents a monoanionic ligand. 1 is replaced or Unsubstituted alkyl groups having 1 to 4 carbon atoms, or substituted or unsubstituted aryl groups having 6 to 10 carbon atoms. R represents a cyclic group; 2 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or an unsubstituted phenyl group, R 3 is hydrogen or a substituted or unsubstituted carbon atom represents an alkyl group having a number of 1 to 4; 1represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms. In addition, Ar 1 and R 1 ~R 3 Specific examples of are the same as those of general formula (G1).

[0068] The above Ar 1 is a phenylene group, which is preferable since synthesis is easy. One embodiment of the present invention is an organometallic complex represented by General Formula (G5).

[0069] [ka]

[0070] In the general formula (G5), L represents a monoanionic ligand. 1 is substituted or unsubstituted an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, Represents R 2 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or represents an unsubstituted phenyl group, R 3 is hydrogen or a substituted or unsubstituted C1-4 represents an alkyl group, R 4 ~R 7 each independently represents a hydrogen atom or a number of substituted or unsubstituted carbon atoms; an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 4 carbon atoms, Unsubstituted alkylthio groups having 1 to 4 carbon atoms, halogen groups, substituted or unsubstituted alkylthio groups having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms. Oh, R 1 ~R 7 Specific examples of are the same as those of general formula (G2).

[0071] Another embodiment of the present invention is an organometallic complex represented by General Formula (G6). As shown in the structure represented by the formula (1), when a phenyl group is attached to the 6-position of the pyrimidine skeleton, organometallic complexes can be formed. This is preferred because it improves the yield of the enzyme.

[0072] [ka]

[0073] In the general formula (G6), L represents a monoanionic ligand. 2 is hydrogen, substituted or represents an 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 12 teeth each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted or is an unsubstituted alkoxy group having 1 to 4 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms a thio group, a halogen group, a substituted or unsubstituted haloalkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted or an unsubstituted aryl group having 6 to 10 carbon atoms. 2 ~R 12 A concrete example is Same as general formula (G3).

[0074] Another embodiment of the present invention is an organometallic complex represented by general formula (G7).

[0075] [ka]

[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 alkyl group having 1 to 4 carbon atoms. or an unsubstituted aryl group having 6 to 10 carbon atoms; R 2 is hydrogen, substituted or unsubstituted. R represents a substituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted phenyl group; 3 teeth, represents hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms; Ar 1 is replaced or It represents an unsubstituted arylene group having 6 to 10 carbon atoms. 1 and R 1 ~R 3 Specific examples include , which is the same as general formula (G1).

[0077] The above Ar 1 is a phenylene group, which is preferable since synthesis is easy. One embodiment of the present invention is an organometallic complex represented by general formula (G8).

[0078] [ka]

[0079] In general formula (G8), R 1 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. or an unsubstituted aryl group having 6 to 10 carbon atoms; R 2 is hydrogen, substituted or unsubstituted. R represents a substituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted phenyl group; 3 teeth, represents hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms; R 4 ~R 7 Is that each independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted substituted alkoxy group having 1 to 4 carbon atoms, 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 It represents an unsubstituted aryl group having 6 to 10 carbon atoms. 1 ~R 7Specific examples of the compound represented by the general formula (G Same as 2).

[0080] Another embodiment of the present invention is an organometallic complex represented by General Formula (G9). As shown in the structure represented by the formula (1), when a phenyl group is attached to the 6-position of the pyrimidine skeleton, organometallic complexes can be formed. This is preferred because it improves the yield of the enzyme.

[0081] [ka]

[0082] In general formula (G9), R 2 is hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or represents a substituted or unsubstituted phenyl group, R 3 is hydrogen or a substituted or unsubstituted carbon atom. Represents an alkyl group having 1 to 4 prime numbers, R 4 ~R 12 are each independently hydrogen, a substituent or Unsubstituted alkyl group having 1 to 4 carbon atoms, 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 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; R 2 ~R 12 Specific examples of are the same as those of general formula (G3).

[0083] In the organometallic complexes represented by the general formulae (G4) to (G6), the monoanionic ligand is A monoanionic bidentate chelating ligand having a beta-diketone structure and a carboxyl group. Monoanionic bidentate chelating ligands with phenolic hydroxyl groups or a monoanionic bidentate ligand in which both coordination elements are nitrogen. It is preferably a chelating ligand. In particular, it is preferably a monoanion having a beta-diketone structure. It is preferable that the beta-diketone structure is a functional bidentate chelating ligand. This increases the solubility of the organometallic complex in an organic solvent, which is preferable since it makes purification easier. The presence of a ketone structure is preferable because it allows the production of an organometallic complex with high luminescence efficiency. In addition, the beta-diketone structure enhances sublimation and provides excellent vapor deposition performance. There are advantages.

[0084] In the organometallic complexes represented by the general formulas (G4) to (G6), monoanionic coordination The atom is preferably any one of the general formulae (L1) to (L7).

[0085] [ka]

[0086] In general formulas (L1) to (L7), R 71 ~R 109 are each independently hydrogen, a substituent or is an unsubstituted alkyl group having 1 to 4 carbon atoms, a halogen group, a vinyl group, a substituted or unsubstituted carbon a haloalkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 4 carbon atoms, or A represents a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms. 1 ~A 3 Is that Independently, sp bonds to nitrogen and hydrogen 2 Hybridized carbon or sp bonded to the substituent R 2 carbon wherein the substituent R is an alkyl group having 1 to 4 carbon atoms, a halogen group, a haloalkyl group having 1 to 4 carbon atoms, It represents a phenyl group or a phenyl group.

[0087] <Method for synthesizing 4-arylpyrimidine derivative represented by general formula (G0)> Regarding an example of a method for synthesizing a 4-arylpyrimidine derivative represented by the following general formula (G0), The 4-arylpyrimidine derivative represented by the following general formula (G0) is as follows: The compound can be synthesized according to the simple synthetic scheme (a), (a'), or (a'').

[0088] [ka]

[0089] In general formula (G0), R 1 is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, R 2 is hydrogen, substituted or represents an 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; Ar 2 Is, place It represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.

[0090] For example, a 4-arylpyrimidine derivative represented by the general formula (G0) can be synthesized according to the synthesis scheme (a As shown in Fig. 1, an arylboronic acid (A1) is reacted with a halogenated pyrimidine compound (A2). It is obtained by coupling.

[0091] [ka]

[0092] In the synthesis scheme (a), X represents a halogen, R 1 is a substituted or unsubstituted carbon represents an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, R 2 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted R represents a substituted phenyl group; 3 is hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. represents an alkyl group, and Ar 2 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.

[0093] The 4-arylpyrimidine derivative represented by the general formula (G0) can be synthesized by the synthesis scheme (a' As shown in (A1'), an aryllithium compound or a Grignard reagent shown in (A1') can be used as a pyridine derivative. The compound (A2') can be obtained by reacting the compound (A2') with the amine compound (A2').

[0094] [ka]

[0095] In the synthetic scheme (a'), X represents a halogen, R 1 is substituted or unsubstituted Represents an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms. S, R 2 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or represents an unsubstituted phenyl group, and R 3 is hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. represents an alkyl group, and Ar 2 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.

[0096] The 4-arylpyrimidine derivative represented by the general formula (G0) can be synthesized by the synthesis scheme (a' As shown in (a), aryl 1,3-diketones (A1'') and amidines (A2'') are It is obtained by reacting

[0097] [ka]

[0098] In general formula (G0), R 3 In the case of hydrogen, see H. Bredere ck, R. Gompper, G. Morlock, “Chemische Berich As shown in "E.T.E.", 90, 942 (1957)), aryl 1,3-diketones ( It can be obtained by heating and reacting A1'') with formamide in the presence of an acid catalyst.

[0099] In the synthetic scheme (a''), R 1 is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. R represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; 2 is hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted phenyl group; Represents R 3 represents hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms; Ar 2 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.

[0100] The above-mentioned compounds (A1), (A2), (A1'), (A2'), (A1''), (A2'' ) is commercially available in various types or can be synthesized, and is therefore represented by the general formula (G0): A large number of types of 4-arylpyrimidine derivatives can be synthesized. Therefore, the organometallic complexes according to one embodiment of the present invention have a wide variety of ligands. It has the following characteristics.

[0101] <<Method for Synthesizing Organometallic Complexes of 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 ortho-metallated to form Among the organometallic complexes according to one embodiment of the present invention, those represented by the following general formula (G The synthesis methods of the organometallic complexes represented by 4) and (G7) will now be described.

[0102] [ka]

[0103] In the general formulae (G4) and (G7), L represents a monoanionic ligand, R 1 teeth, A substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted alkyl group having 6 to 4 carbon atoms. R represents 10 aryl groups; 2 is hydrogen, substituted or unsubstituted alkyl having 1 to 4 carbon atoms R represents a substituted or unsubstituted phenyl group; 3 is hydrogen, or a substituted or unsubstituted represents an alkyl group having 1 to 4 carbon atoms; 1 is a substituted or unsubstituted alkyl group having 6 to 10 carbon atoms. Represents a rylene group.

[0104] <Method for synthesizing an organometallic complex represented by general formula (G4) according to one embodiment of the present invention> First, as shown in the following synthesis scheme (b), a 4-arylpyridine derivative represented by general formula (G0) is synthesized. Iridium halide compounds (iridium chloride, iridium bromide, iridium iodide, iridium trichloride, etc., preferably iridium trichloride hydrate) in a solvent-free, alcohol-based Solvents (glycerol, ethylene glycol, 2-methoxyethanol, 2-ethoxyethanol Alone or in a mixture of one or more alcoholic solvents and water, By heating in a gas atmosphere, the halogen-bridged organometallic complex It is one of the types of heating, and a novel dinuclear complex (B) can be obtained. There is no set temperature, and an oil bath, a sand bath, or an aluminum block may be used. It is also possible to use microwaves as a heating means.

[0105] [ka]

[0106] In the synthesis scheme (b), X represents a halogen, and R 1 is a substituted or unsubstituted carbon represents an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, R 2 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted R represents a substituted phenyl group; 3 is hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. Also, Ar 1 represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms, Ar 2 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.

[0107] Furthermore, as shown in the following synthesis scheme (c), The nuclear complex (B) is reacted with the monoanionic ligand raw material HL in an inert gas atmosphere. By this, the proton of HL is eliminated and L is coordinated to the central metal Ir, and the general formula (G4) is obtained. The organometallic complex according to one embodiment of the present invention is represented by the following formula: Alternatively, an oil bath, a sand bath, or an aluminum block may be used. It can also be used as a heating means.

[0108] [ka]

[0109] In the synthesis scheme (c), L represents a monoanionic ligand and X represents a halogen. S, R 1 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted R represents an aryl group having 6 to 10 carbon atoms. 2 is hydrogen, substituted or unsubstituted carbon atom number 1 to R represents an alkyl group represented by the formula (I) or a substituted or unsubstituted phenyl group; 3 is hydrogen or a substitution or an unsubstituted alkyl group having 1 to 4 carbon atoms; Ar 1 is the number of substituted or unsubstituted carbon atoms Represents 6 to 10 arylene groups.

[0110] In the present invention, as described above, an ortho-arylpyrimidine derivative having a 4-arylpyrimidine derivative as a ligand is used. To obtain the metal complex, the 6-position of the pyrimidine (i.e., R 1 ) with the introduction of a substituent. Especially R 1 As the alkyl group, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted The aryl group has 6 to 10 carbon atoms. 1 When hydrogen is used as In comparison with the case of the above, the halogen-bridged binuclear metal complex produced in the synthesis scheme (b) The decomposition of is suppressed during the reaction shown in the synthetic scheme (c), resulting in a dramatically higher yield. The rate can be obtained.

[0111] In addition, the monoanionic ligand L in the general formula (G4) has a beta-diketone structure. Monoanionic bidentate chelating ligands with carboxyl groups. chelate ligands, monoanionic bidentate chelate ligands having a phenolic hydroxyl group; Or, it is a monoanionic bidentate chelating ligand in which both of the two coordination elements are nitrogen. In particular, a monoanionic bidentate chelating ligand having a beta-diketone structure is preferred. In this case, the beta-diketone structure increases the solubility of the organometallic complex in an organic solvent. In addition, the presence of a beta-diketone structure increases the luminous efficiency. In addition, it is preferable to use a beta-diketone structure because it is possible to obtain an organometallic complex having a high molecular weight. This has the advantage of improving sublimation properties and providing excellent deposition performance.

[0112] The monoanionic ligand is any one of the general formulas (L1) to (L7). These ligands are preferred because they have high coordination ability and are available at low cost. It is therefore effective.

[0113] [ka]

[0114] In general formulas (L1) to (L7), R 71 ~R 109 are each independently hydrogen, a substituent or is an unsubstituted alkyl group having 1 to 4 carbon atoms, a halogen group, a vinyl group, a substituted or unsubstituted carbon a haloalkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 4 carbon atoms, or A represents a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms. 1 ~A 3 Is that Independently, sp bonds to nitrogen and hydrogen 2 Hybridized carbon or sp bonded to the substituent R 2 carbon wherein the substituent R is an alkyl group having 1 to 4 carbon atoms, a halogen group, 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 represented by general formula (G7) according to one embodiment of the present invention> The organometallic complex of one embodiment of the present invention represented by General Formula (G7) can be synthesized by the following synthesis scheme (d That is, the 4-arylpyridine represented by the general formula (G0) can be synthesized by the method described below. iridium derivatives and iridium halide compounds (iridium chloride, iridium bromide, iridium iodide, iridium chloride, preferably iridium trichloride hydrate, or an iridium organometallic complex After mixing with a compound (acetylacetonato complex, diethylsulfide complex, etc.), heat By this, an organometallic complex having a structure represented by general formula (G7) can be obtained. This heating process also produces a 4-arylpyrimidine derivative represented by the general formula (G0): The compound and an iridium halide compound or an iridium organometallic complex compound are mixed in an alcohol. Solvents (glycerol, ethylene glycol, 2-methoxyethanol, 2-ethoxyethanol The heating may be performed after dissolving the mixture in an oil bath or in an alcohol (ethanol, etc.). Alternatively, a sand bath or an aluminum block may be used. It is also possible to use

[0116] [ka]

[0117] In the synthetic scheme (d), 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 Hydrogen, substitution also or an 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 1 represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms, Ar 2 is replaced or eliminated It represents a substituted aryl group having 6 to 10 carbon atoms.

[0118] In the present invention, as described above, an ortho-arylpyrimidine derivative having a 4-arylpyrimidine derivative as a ligand is used. To obtain the metal complex, the 6-position of the pyrimidine (i.e., R 1 ) with the introduction of a substituent. Especially R 1 As the alkyl group, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted The aryl group has 6 to 10 carbon atoms. 1 When hydrogen is used as As compared with the case of the synthesis scheme (d), the yield can be increased.

[0119] Although an example of the synthesis method has been described above, the organometallic complex which is one embodiment of the disclosed present invention may be synthesized by any other synthesis method.

[0120] The following structural formulae (100) to (201) show specific structural formulae of organometallic complexes according to embodiments of the present invention. However, the present invention is not limited to these.

[0121] [ka]

[0122] [ka]

[0123]

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[0124]

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[0125]

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[0126]

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[0127]

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[0128]

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[0129]

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[0130]

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[0131]

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[0132]

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[0133]

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[0134] [ka]

[0135] [ka]

[0136] [ka]

[0137] [ka]

[0138] [ka]

[0139] In addition, the organometallic complexes represented by the above structural formulas (100) to (201) have the following types of ligands: In some cases, stereoisomers may exist, and the organometallic complex of one embodiment of the present invention may include these isomers. Also includes all.

[0140] The organometallic complex according to one embodiment of the present invention can emit phosphorescence and emit red light. It has a wide emission spectrum from 100 to 1000 nm, making it suitable for use as a light-emitting material or a light-emitting substance for light-emitting devices. It can be used as.

[0141] By using the organometallic complex of one embodiment of the present invention, a light-emitting element, a light-emitting device, and an electrode having high emission efficiency can be obtained. Alternatively, a light emitting element or a light emitting device with low power consumption can be realized. The present invention can be implemented as a device, an electronic device, or a lighting device.

[0142] In addition, by using the organometallic complex of one embodiment of the present invention, a light-emitting element and a light-emitting device with high reliability can be obtained. , electronic devices, or lighting devices can be realized.

[0143] In this embodiment mode, the structures shown in the other embodiment modes can be appropriately combined and used. can.

[0144] (Embodiment 2) In this embodiment, as one embodiment of the present invention, the organometallic complex described in Embodiment 1 is used as a light-emitting element. The light-emitting element used in the layer will be described with reference to FIG.

[0145] FIG. 1A shows a light-emitting device having an EL layer 102 between a first electrode 101 and a second electrode 103. The EL layer 102 includes a light-emitting layer 113. The light-emitting layer 113 is preferably The organometallic complex according to one embodiment of the present invention described in the first embodiment is included.

[0146] By applying a voltage to such a light-emitting element, light is injected from the first electrode 101 side. The holes injected from the second electrode 103 side and the electrons injected from the second electrode 103 side are recombined in the light-emitting layer 113. The excited organometallic complex then returns to the ground state. In this manner, the organometallic complex of one embodiment of the present invention can be used as a light-emitting element. In the light-emitting element shown in this embodiment, the first electrode 1 The first electrode 101 functions as an anode and the second electrode 103 functions as a cathode.

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

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

[0149] The first electrode 101 is formed by, for example, a sputtering method or a deposition method (including a vacuum deposition method). It can be achieved.

[0150] The EL layer 102 formed on the first electrode 101 has at least a light-emitting layer 113. In addition, the EL layer 102 is formed by including an organometallic complex according to one embodiment of the present invention. Known substances can be used, and either low molecular weight compounds or high molecular weight compounds can be used. The material forming the EL layer 102 may be made of only organic compounds. In addition, the term also includes compositions that partially contain inorganic compounds.

[0151] The EL layer 102 includes a light-emitting layer 113 and a material having a high hole-injecting property as shown in FIG. the hole transport layer 112 containing a material with high hole transport properties; The electron transport layer 114 includes a material having a high electron transporting property, and the electron It is formed by appropriately combining and laminating the child injection layer 115 and the like.

[0152] The hole-injection layer 111 is a layer containing a substance with high hole-injection properties. The oxides are molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, Aluminum oxide, Chromium oxide, Zirconium oxide, Hafnium oxide, Tantalum oxide, Silver Metal oxides such as oxides of tungsten, manganese, etc. can be used. Phthalocyanine (abbreviation: H 2 Pc), copper(II) phthalocyanine (abbreviation: CuPc) Phthalocyanine compounds such as the above can be used.

[0153] In addition, the low molecular weight organic compound 4,4',4''-tris(N,N-diphenylamino) ) Triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl) (N-phenylamino)triphenylamine (abbreviation: MTDATA), 4 ,4'-Bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl 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-(9-phenylcarbazol-3-yl)benzene (abbreviation: DPA3B) )-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3, 6-Bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9- Phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-( 9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: P Aromatic amine compounds such as CzPCN1) can be used.

[0154] Furthermore, polymeric compounds (oligomers, dendrimers, polymers, etc.) can also be used. For example, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltrifluoroethylene) phenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenyl phenyl-N'-phenylamino}phenyl)methacrylamide (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bi Examples of polymer compounds include poly(phenyl)benzidine (abbreviation: Poly-TPD). In addition, poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), polyaniline / poly(styrenesulfonic acid) (PAni / PS A polymer compound to which an acid such as dimethylaminoethyl ether (S) is added can be used.

[0155] The hole injection layer 111 is formed by mixing an organic compound and an electron acceptor. Such a composite material may be used in which the electron acceptor is attached to the organic compound. Since holes are generated, the organic compound has excellent hole injection and hole transport properties. It is preferable that the material is excellent in transporting the generated holes (a material with high hole transporting property). stomach.

[0156] The organic compounds used in the composite materials include aromatic amine compounds, carbazole derivatives, aromatic Various compounds such as aromatic hydrocarbons and polymer compounds (oligomers, dendrimers, polymers, etc.) As the organic compound used for the composite material, a compound having a high hole transporting property can be used. It is preferable that the organic compound is a compound having a low molecular weight. -6 cm 2 Hole transfer above / Vs However, it is preferable that the material has a higher hole transporting property than the electron transporting property. In the following, organic compounds that can be used in the composite material are described. The compounds are specifically listed below.

[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 1,1'-biphenyl-4,4'-diamine (TPD), 4-phenyl- 4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP) ) and aromatic amine compounds such as 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-carbazo Carbazole derivatives such as [aryl(phenyl)]-2,3,5,6-tetraphenylbenzene It can be used.

[0158] In addition, 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. An aromatic hydrocarbon compound can be used.

[0159] Furthermore, 2,3,6,7-tetramethyl-9,10-di(2-naphthyl)anthracene, 9,9'-bianthryl, 10,10'-diphenyl-9,9'-bianthryl, 10, 10'-Bis(2-phenylphenyl)-9,9'-bianthryl, 10,10'-bis [(2,3,4,5,6-pentaphenyl)phenyl]-9,9'-bianthryl, an Thracene, tetracene, rubrene, perylene, 2,5,8,11-tetra(tert-bu (ethyl)perylene, pentacene, coronene, 4,4'-bis(2,2-diphenylvinyl) Biphenyl (abbreviation: DPVBi), 9,10-bis[4-(2,2-diphenylvinyl) It is possible to use aromatic hydrocarbon compounds such as diphenylanthracene (DPVPA). can.

[0160] In addition, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroethylene is used as an electron acceptor. F 4 -TCNQ), chloranil, and other organic compounds, as well as transition metals In addition, metal oxides belonging to groups 4 to 8 of the periodic table can be used. Specifically, vanadium oxide, niobium oxide, tantalum oxide, Chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide are electrically Among them, molybdenum oxide is particularly stable in the atmosphere and has a high molecular weight. It is preferred because it has low moisture content and is easy to handle.

[0161] In addition, the above-mentioned polymer compounds such as PVK, PVTPA, PTPDMA, and Poly-TPD A composite material may be formed using the above-mentioned electron acceptor and used for the hole injection layer 111.

[0162] The hole-transporting layer 112 is a layer containing a substance having a high hole-transporting property. The following are examples of 4,4'-bis[N-(9,9-dimethylfluorophenyl) 4,4-Diphenyl-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), '-Bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino] An aromatic amine compound such as biphenyl (abbreviation: BSPB) can be used. The substances mentioned are mainly 10 -6 cm 2 / Vs or more. Any other substance may be used as long as it has a higher hole transporting property than an electron transporting property. The layer containing a substance having a high hole-transporting property may be a single layer or may be a layer having two or more layers of the above substance. It may also be laminated on top.

[0163] The hole transport layer 112 may also include a carbazole derivative such as CBP, CzPA, or PCzPA. Anthracene derivatives such as t-BuDNA, DNA, and DPAnth may also be used. stomach.

[0164] The hole transport layer 112 may be formed of a material such as PVK, PVTPA, PTPDMA, or Poly-TPD. Any polymeric compound can be used.

[0165] The light-emitting layer 113 contains the organometallic complex which is one embodiment of the present invention as described in Embodiment 1. The light-emitting layer 113 is formed of a thin film made of an organometallic complex according to one embodiment of the present invention. Alternatively, the organometallic complex may have a triplet excitation energy higher than that of the organometallic complex of one embodiment of the present invention. A substance having such a structure is used as a host, and an organometallic complex according to one embodiment of the present invention is dispersed as a guest. The light-emitting layer 113 may be formed of a thin film of the organometallic complex. It is possible to prevent quenching due to the degree of triplet excitation. , is the energy difference between the ground state and the triplet excited state.

[0166] The electron-transporting layer 114 is a layer containing a substance with a high electron-transporting property. For details, please refer to Alq 3 , tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Alm q 3), Bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq 2 ), BAlq, Zn(BOX) 2 , bis[2-(2-hydroxyphenyl)benzothiazolidinyl] Zorato]zinc (abbreviation: Zn(BTZ) 2 ) and other metal complexes. -biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazo PBD, 1,3-bis[5-(p-tert-butylphenyl)-1,3 ,4-Oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-ter t-Butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triphenyl TAZ (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl) p-EtTA Z), Bathophenanthroline (abbreviation: BPhen), Bathocuproine (abbreviation: BCP) , 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: Bz Heteroaromatic compounds such as poly(2,5-pyridine-Os) can also be used. diyl) (abbreviation: PPy), poly[(9,9-dihexylfluorene-2,7-diyl) -co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9,9-di 2,2'-bipyridine-6,6'-diyl)-co-(2,2'-bipyridine-6,6'-diyl) Polymer compounds such as PF-BPy can also be used. The substances that were found were mainly 10 -6 cm 2 / Vs or higher. Any substance other than the above may be used for the electron transport layer as long as it has a higher electron transporting property than the above. stomach.

[0167] The electron transport layer may be a single layer or a laminate of two or more layers of the above-mentioned materials. It may also be possible to use the following.

[0168] The electron injection layer 115 is a layer containing a substance with high electron injection properties. fluoride, cesium, calcium, lithium fluoride, cesium fluoride, calcium fluoride, Uses alkali metals, alkaline earth metals, or compounds thereof, such as lithium oxide, etc. Also, rare earth metal compounds such as erbium fluoride can be used. Moreover, the above-mentioned materials constituting the electron transport layer 114 can also be used.

[0169] Alternatively, the electron injection layer 115 may be a composite material made by mixing an organic compound and an electron donor. Such composite materials are made by adding electrons to an organic compound by an electron donor. In this case, the organic compound is It is preferable that the material has excellent transport properties for the generated electrons. Specifically, for example, the above-mentioned The material constituting the electron transport layer 114 (metal complex, heteroaromatic compound, etc.) can be used. The electron donor may be any substance that exhibits electron donating properties to organic compounds. For the metal, alkali metals, alkaline earth metals and rare earth metals are preferred, and lithium, cesium, Magnesium, calcium, erbium, ytterbium, etc. Preferred are lithium metal oxides and alkaline earth metal oxides, and lithium oxide and calcium oxide are preferred. , barium oxide, etc. Also, Lewis bases such as magnesium oxide are used. It is also possible to use organic compounds such as tetrathiafulvalene (TTF). It is also possible.

[0170] The hole injection layer 111, the hole transport layer 112, the light emitting layer 113, and the electron transport layer 114 The electron injection layer 115 is formed by a deposition method (including a vacuum deposition method), an inkjet method, a coating method, and the like, respectively. It can be formed by a method such as a cloth method.

[0171] The second electrode 103, which functions as a cathode, is made of a material having a small work function (preferably 3.8 eV or less). Lower) It is preferable to form the electrode using a metal, an alloy, an electrically conductive compound, or a mixture thereof. Specifically, elements belonging to Group 1 or 2 of the Periodic Table, such as lithium and Alkali metals such as cesium, and alkali metals such as magnesium, calcium, and strontium Lithium-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 these, aluminum and silver are also used. There can be.

[0172] However, the layer of the EL layer 102 formed in contact with the second electrode 103 is the above-mentioned organic compound. When a composite material made by mixing a compound and an electron donor is used, the work function is large. Indium oxide containing Al, Ag, ITO, silicon or silicon oxide, regardless of size A variety of conductive materials can be used, such as tin oxide.

[0173] In addition, when forming the second electrode 103, a vacuum deposition method or a sputtering method is used. In addition, when using silver paste, the coating method or the inkjet method can be used. It can be used.

[0174] The light-emitting element described above emits a light emitting diode (LED) by a potential difference generated between the first electrode 101 and the second electrode 103. A current flows, and holes and electrons recombine in the EL layer 102, causing light to be emitted. The emitted light passes through either the first electrode 101 or the second electrode 103 or both. Therefore, either the first electrode 101 or the second electrode 103 Alternatively, both of the electrodes may be transparent to visible light.

[0175] Using the light-emitting element described in this embodiment mode, a passive matrix light-emitting device or a transistor An active matrix type light emitting device in which the driving of the light emitting element is controlled by a stator is manufactured. It is possible.

[0176] In addition, the structure of a transistor in the case of manufacturing an active matrix type light emitting device is For example, a staggered or inverted staggered transistor may be used as appropriate. In addition, the driving circuit formed on the substrate is made up of N-type and P-type transistors. Alternatively, the transistor may be made up of only N-type transistors or only P-type transistors. Furthermore, the crystallinity of the semiconductor film used in the transistor may be specified. For example, an amorphous semiconductor film, a crystalline semiconductor film, or the like can be used. In addition, the semiconductor film may be made of a single element such as silicon, or an oxide semiconductor. can be done.

[0177] In this embodiment, the organometallic complex of one embodiment of the present invention used in the light-emitting layer 113 has a wide emission spectrum from red to green wavelengths. Therefore, it has high color rendering properties. The device can be realized.

[0178] In addition, since the light-emitting element of this embodiment includes the organometallic complex of one embodiment of the present invention, the light-emitting efficiency In addition, a light-emitting element with low power consumption can be realized. In addition, a highly reliable light-emitting element can be realized.

[0179] In this embodiment mode, the structures shown in the other embodiment modes can be appropriately combined and used. can.

[0180] (Embodiment 3) The light-emitting element of one embodiment of the present invention may have a plurality of light-emitting layers. By providing a light emitting layer and emitting light from each of the light emitting layers, it is possible to obtain a light emission that is a mixture of multiple lights. Therefore, for example, white light can be obtained. An embodiment of a light-emitting element having a light-emitting layer will be described with reference to FIG.

[0181] FIG. 1B shows a light-emitting device having an EL layer 102 between a first electrode 101 and a second electrode 103. 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 FIG. 1B has a structure in which light is emitted from the first light-emitting layer 213 and the second light-emitting layer 214. The light emitted from the first light-emitting layer 213 and the second light-emitting layer 215 can be mixed. It is preferable to have a separation layer 214 between the light emitting layer 215 .

[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 including an organometallic complex according to one embodiment of the present invention in the optical layer 215 will be described. Not limited to.

[0183] The first light-emitting layer 213 is formed using an organometallic complex according to one embodiment of the present invention, and the second light-emitting layer 215 is formed using an organometallic complex according to one embodiment of the present invention. Other luminescent materials may also be applied.

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

[0185] A voltage is applied so that the potential of the first electrode 101 is 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 and the second light-emitting layer 214 are The holes and electrons recombine in the light-emitting layer 215 or the separation layer 214. 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 luminescent material contained in the second luminescent layer 213 and the second luminescent material contained in the second luminescent layer 215 are excited. The first luminescent material and the second luminescent material in the excited state are then respectively It emits light when it returns to the ground state.

[0186] The first light-emitting layer 213 contains perylene, 2,5,8,11-tetra(tert-butyl)perylene. Rylene (abbreviation: TBP), DPVBi, 4,4'-bis[2-(N-ethylcarbazole -3-yl)vinyl]biphenyl (abbreviation: BCzVBi), BAlq, bis(2-methyl -8-Quinolinolato)gallium chloride (Gamq 2 Fluorescent compounds such as bis(Cl) and {2-[3,5-bis(trifluoromethyl)phenyl]pyridinato-N,C 2’}Ili Ir(III) picolinate (abbreviation: [Ir(CF 3 ppy) 2 (pic)]), Bis [2-(4,6-difluorophenyl)pyridinato-N,C 2’ ]Iridium(III) Acetylacetonate (abbreviation: [FIr(acac)]), bis[2-(4,6-difluoro (O-phenyl)pyridinato-N,C 2’ ]Iridium(III) picolinate (abbreviation: F Irpic), bis[2-(4,6-difluorophenyl)pyridinato-N,C 2’ ]stomach Phosphorescent compounds such as rhodium(III) tetra(1-pyrazolyl)borate (abbreviation: FIr6) It contains the first luminescent material, which is represented by a compound, and has an emission spectrum of 450 to 510 nm. Light emission having a blue-green peak (that is, blue to blue-green) can be obtained.

[0187] In addition, the first light-emitting layer 213 is configured such that, when the first light-emitting material is a fluorescent compound, A substance having a singlet excitation energy larger than that of the first host is used as the first host. It is preferable that the layer is formed by dispersing a light-emitting material as a guest. In the case of a phosphorescent compound, a substance having a triplet excitation energy higher than that of the first emitting substance is It is preferable that the first light-emitting material is dispersed as a guest in the layer. As the first host, in addition to the above-mentioned NPB, CBP, TCTA, etc., DNA, t-BuDNA, etc. can be used. Note that the singlet excitation energy is the energy between the ground state and This is the energy difference with the singlet excited state.

[0188] The second light-emitting layer 215 contains an organometallic complex according to one embodiment of the present invention and emits red to green light. The second light-emitting layer 215 has the same structure as the light-emitting layer 113 described in the second embodiment. A similar configuration may be used.

[0189] The separation layer 214 is specifically made of the above-mentioned TPAQn, NPB, CBP, TCTA, Zinc2 In this way, the separation layer 214 can be formed by using ZnBOX or the like. By providing the first light-emitting layer 213 and the second light-emitting layer 215, the light emission intensity of only one of the first light-emitting layer 213 and the second light-emitting layer 215 is However, the separation layer 214 is not necessarily It is not necessary, and the ratio of the emission intensity of the first light-emitting layer 213 to the emission intensity of the second light-emitting layer 215 In order to adjust the above, it is sufficient to provide an appropriate amount of pressure.

[0190] The EL layer 102 includes a hole injection layer 111, a hole transport layer 112, an electron transport layer 113, and a light emitting layer. The structures of these layers are the same as those of the second embodiment. However, these layers are not necessarily required, and This should be set appropriately according to the child's characteristics.

[0191] Note that the structure shown in this embodiment mode may be used in appropriate combination with structures shown in other embodiment modes. It is possible.

[0192] (Embodiment 4) In this embodiment, as one embodiment of the present invention, a light-emitting element having a structure having a plurality of EL layers ( The light-emitting element (hereinafter referred to as a stacked element) will be described with reference to FIG. 1(C). A plurality of EL layers (first EL layer in FIG. 1C) are disposed between the first electrode 101 and the second electrode 103. This is a stacked type light emitting device having a first EL layer 700 and a second EL layer 701. Although the case where the EL layer has two layers is shown, three or more layers may be used.

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

[0194] In this embodiment, all of the EL layers are the same as the EL layers shown in the second embodiment. The first EL layer 7 may have the same structure, or a part of the first EL layer 7 may have the same structure. The EL layer 700 and the second EL layer 701 may have the same or different compositions. The same as in the second embodiment can be applied to the above.

[0195] In FIG. 1C, a charge is introduced between the first EL layer 700 and the second EL layer 701. A charge generating layer 305 is provided. The charge generating layer 305 is disposed between the first electrode 101 and the second electrode 102. When a voltage is applied to 03, electrons are injected into one EL layer and holes are injected into the other EL layer. In the present embodiment, the first electrode 101 is connected to the second electrode 103. When a voltage is applied so that the potential becomes higher, the charge generating layer 305 emits light to the first EL layer 700. Electrons are injected and holes are injected into the second EL layer 701 .

[0196] The charge generating layer 305 is transparent to visible light from the viewpoint of light extraction efficiency. In addition, the charge generation layer 305 is preferably formed of a first electrode 101 or a second electrode 103. It also works well with low electrical conductivity.

[0197] The charge generating layer 305 contains an organic compound with high hole transport properties and an electron acceptor. Even if the composition includes an organic compound having high electron transport properties and an electron donor, Also, both of these configurations may be laminated.

[0198] In the case where an electron acceptor is added to an organic compound having high hole transport properties, Examples of organic compounds with high transport properties include NPB, TPD, TDATA, MTDATA, 4,4'-Bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenyla Aromatic amine compounds such as bis(amino)biphenyl (abbreviation: BSPB) can be used. The substances mentioned here are mainly 10 -6 cm 2 / Vs or higher. However, any organic compound that has a higher hole transporting property than electron transporting property may be used. That's fine.

[0199] In addition, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroethylene is used as an electron acceptor. F 4 -TCNQ), chloranil, etc. Further, transition metal oxides can be mentioned. Examples of the oxides of metals belonging to the group include vanadium oxide, niobium oxide, Tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, lanthanum oxide Molybdenum oxide is preferred because it has high electron-accepting properties. In particular, molybdenum oxide is stable in the atmosphere. This is preferable because it has low hygroscopicity and is easy to handle.

[0200] On the other hand, in the case where an electron donor is added to an organic compound having high electron transport properties, Examples of organic compounds with high electron transport properties include Alq and Almq. 3 , BeBq 2 , B.A. Iq, etc., metal complexes having a quinoline skeleton or a benzoquinoline skeleton can be used. In addition, Zn(BOX) 2 , Zn(BTZ) 2 Oxazoles such as thiazo Metal complexes having a tetrahydrofuran ligand can also be used. PBD, OXD-7, TAZ, BPhen, BCP, etc. can also be used. The solid material is mainly 10 -6 cm 2 / Vs or higher. Any organic compound having a higher electron transporting property than holes may be used other than the above.

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

[0202] In addition, the charge generating layer 305 is formed using the above-mentioned material, and the EL layer is laminated. In this case, the increase in the driving voltage can be suppressed.

[0203] In this embodiment, a light-emitting element having two EL layers has been described. However, a light-emitting element having three or more EL layers may be used. The present invention can be similarly applied to a light emitting device in which layers are stacked. In the case of a light-emitting element, a charge generating layer is sandwiched between a pair of electrodes, and multiple EL layers are arranged. This allows light emission in a high brightness range while keeping the current density low. In addition, when applied to lighting, the resistance of the electrode material is This reduces the voltage drop caused by the driving voltage, enabling uniform light emission over a large area. It is possible to realize a light emitting device that is capable of realizing a light emitting device with low power consumption.

[0204] In addition, by making the emission color of each EL layer different, the light-emitting device as a whole can have a desired color. 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 to each other, It is also possible to obtain a light-emitting element that emits white light as a whole. In other words, colors that are complementary to each other are obtained from materials that emit light. By mixing the emitted light, white light can be obtained.

[0205] The same applies to a light-emitting element having three EL layers. For example, the light-emitting element of the first EL layer The light color of the first EL layer is red, the light color of the second EL layer is green, and the light color of the third EL layer is blue. In some cases, the light emitting element as a whole can emit white light.

[0206] Note that the structure shown in this embodiment mode may be used in appropriate combination with structures shown in other embodiment modes. It is possible.

[0207] (Embodiment 5) In this embodiment, a passive matrix light-emitting device using a light-emitting element according to one embodiment of the present invention will be described. An active matrix light emitting device and an active matrix light emitting device will be described.

[0208] 2 and 3 show examples of a passive matrix type light emitting device.

[0209] A passive matrix type (also called a simple matrix type) light-emitting device has a stripe-shaped A plurality of anodes arranged in parallel in a rectangular shape and a plurality of cathodes arranged in parallel in a stripe shape are perpendicular to each other. The light-emitting layer is sandwiched between the two intersections. The pixel at the intersection of the anode and the selected cathode lights up. become.

[0210] 2A to 2C are top views of a pixel portion before sealing. 2(D) is a cross-sectional view taken along the dashed line A-A' in FIG. 2(C).

[0211] An insulating layer 402 is formed as a base insulating layer over a substrate 401. If not, it is not necessary to form the first insulating layer 402. The electrodes 403 are arranged at equal intervals (FIG. 2(A)).

[0212] In addition, 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, polyimide amide, resist or benzocyclobutene), or Each pixel is made of an SOG film (e.g., an SiOx film containing an alkyl group). The corresponding opening 405 becomes the light emitting region (FIG. 2(B)).

[0213] On a partition wall 404 having an opening, a plurality of inverted tapes are provided which are parallel to each other and intersect with the first electrode 403. The inversely tapered partition wall 406 is formed by photolithography. According to the lithography method, a positive photosensitive resin is used in which the unexposed areas remain as a pattern. By adjusting the exposure dose or development time so that the lower part is etched more, do.

[0214] After forming a partition wall 406 having an inverse tapered shape as shown in FIG. 2(C), as shown in FIG. An EL layer 407 and a second electrode 408 are formed in this order. The combined height of the partition wall 406 is greater than the thickness of the EL layer 407 and the second electrode 408. As a result, the E An L layer 407 and a second electrode 408 are formed. Each is electrically independent.

[0215] The second electrodes 408 are parallel stripes extending in a direction intersecting with the first electrodes 403. The EL layer 407 and the second electrode 404 are also formed on the inversely tapered partition wall 406. However, the EL layer 407 and the second electrode 408 are not connected to the conductive layer. It is divided.

[0216] In this embodiment, one of the first electrode 403 and the second electrode 408 is an anode. As long as the other is a cathode, either one is acceptable. can be appropriately adjusted according to the polarity of the electrodes.

[0217] If necessary, a sealing material such as a sealing can or a glass substrate is attached to the substrate 401. The light emitting element may be disposed in a sealed space by bonding and sealing with an adhesive. This makes it possible to prevent the light emitting element from deteriorating. In addition, the light emitting element may be filled with a material such as a dry inert gas. To prevent this, a desiccant or the like may be placed between the substrate and the sealing material. The desiccant is removed and the material is thoroughly dried. Calcium oxide or barium oxide is used as a desiccant. Substances that absorb moisture by chemical adsorption, such as oxides of alkaline earth metals, Other desiccants include zeolite and silica gel, which are physical adsorbents. Alternatively, a material that adsorbs moisture by this method may be used.

[0218] Next, a passive matrix light-emitting device shown in FIG. 2(A) to FIG. 2(D) is provided with an FPC or the like. A top view of the mounted device is shown in Figure 3.

[0219] In FIG. 3, the pixel portion constituting the image display is arranged so that the scanning lines and the data lines are perpendicular to each other. The lines cross like this.

[0220] Here, the first electrode 403 in FIG. 2 corresponds to the scanning line 503 in FIG. The second electrode 408 corresponds to the data line 508 in FIG. 3, and the inversely tapered partition wall 406 corresponds to the partition wall 5 06. Between the data line 508 and the scanning line 503, the EL layer 407 of FIG. The intersection indicated by area 505 corresponds to one pixel.

[0221] The scanning line 503 is electrically connected to the connection wiring 509 at the wiring end. The data line is connected to the FPC 511b via the input terminal 510. It is connected to FPC 511a via a

[0222] If necessary, a polarizing plate, a circular polarizing plate (including an elliptical polarizing plate), a retardation plate (λ / Optical films such as polarizing plates, λ / 2 plates, and color filters may be provided as appropriate. For example, the plate or the circular polarizer may be provided with an anti-reflection film by diffusing reflected light using surface irregularities. It is possible to apply an anti-glare coating to reduce glare.

[0223] In addition, although an example in which the driving circuit is not provided on the substrate 501 is shown in FIG. An IC chip having a circuit may be mounted.

[0224] In addition, when mounting an IC chip, the area around (outside) the pixel area is used to provide each signal to the pixel area. The data line side IC, which has a driving circuit that transmits signals, and the scan line side IC are mounted on the COG method. Other than the COG method, TCP and wire bonding methods are used as mounting techniques. TCP is a TAB tape with ICs mounted on it. The IC is mounted by connecting the data line side IC and the scan line side IC to the wiring on the element formation substrate. The substrate may be a silicon substrate, a glass substrate, a quartz substrate, or a plastic substrate. A driving circuit may be formed on a TFT substrate.

[0225] Next, an example of an active matrix type light emitting device will be described with reference to FIG. FIG. 4(A) is a top view showing a light emitting device, and FIG. 4(B) is a cut view taken along a dashed line A-A' in FIG. 4(A). The active matrix light emitting device according to the present embodiment is A pixel section 602 provided on a substrate 601, a driving circuit section (source side driving circuit) 603, and a driving A pixel portion 602, a driver circuit portion 603, and a driver circuit portion 604. The driver circuit section 604 is connected to the element substrate 601 and the sealing substrate 606 by a sealant 605. is sealed between

[0226] In addition, on the element substrate 601, a driving circuit section 603 and a driving circuit section 604 are provided. Signals (e.g., video signals, clock signals, start signals, reset signals, etc.) and potentials A wiring 607 is provided for connecting the external input terminals to transmit the signal. An example of providing an FPC (flexible printed circuit) 608 as an external input terminal is shown below. Although only the FPC is shown here, this FPC also includes a printed wiring board. The light emitting device in this specification may include a 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 described with reference to FIG. A driver circuit portion 603 which is a source side driver circuit and a pixel portion are formed. 6, a pixel portion 602 is shown.

[0228] The driving circuit section 603 is a combination of an n-channel TFT 609 and a p-channel TFT 610. The circuit forming the driver circuit section is a CMOS circuit formed by a combination of a semiconductor device and a semiconductor substrate. Alternatively, the transistor may be formed of a CMOS circuit, a PMOS circuit, or an NMOS circuit. In this embodiment, the driver is integrated with the driver circuit formed on the substrate, but this is not necessarily required. In addition, the driving circuit can be formed externally instead of on the substrate.

[0229] The pixel section 602 includes a switching TFT 611, a current control TFT 612, and a current control TFT 613. An anode 61 electrically connected to the wiring (source electrode or drain electrode) of the control TFT 612 The anode 613 is formed of a plurality of pixels including the anode 613 and the insulator 614. Here, a positive photosensitive acrylic resin is used to form the .

[0230] In order to improve the coverage of the film to be laminated on the upper layer, the upper end of the insulator 614 Alternatively, it is preferable that a curved surface having a curvature is formed at the lower end. For example, the insulator 6 When a positive photosensitive acrylic resin is used as the material for 14, a curved portion is formed on the upper end of the insulator 614. It is preferable that the insulating material 6 has a curved surface having a radius of curvature (0.2 μm to 3 μm). 14, a negative type that becomes insoluble in the etchant when exposed to light, or Any positive type that is soluble in the etchant can be used, and is not limited to organic compounds. In addition, inorganic compounds such as silicon oxide and silicon oxynitride can be used. do.

[0231] An EL layer 615 and a cathode 616 are laminated on the anode 613. The anode 613 is connected to the current control TFT 612 by using an ITO film. A laminated film of titanium nitride and a film mainly composed of aluminum, or a titanium nitride film, aluminum When a laminated film of the main component and a titanium nitride film is applied, the resistance as wiring is low, and IT A good ohmic contact can be obtained with the O film. 6 is electrically connected to the FPC 608 which is an external input terminal.

[0232] The EL layer 615 is provided with at least a light-emitting layer. In addition to the light-emitting layer, a hole injection layer, A hole transport layer, an electron transport layer, or an electron injection layer is appropriately provided. A light emitting element 617 is formed by a laminated structure of the organic EL element 15 and the cathode 616 .

[0233] In addition, although only one light emitting element 617 is shown in the cross-sectional view shown in FIG. 02, a plurality of light emitting elements are arranged in a matrix. 2, light-emitting elements capable of emitting three kinds of light (R, G, B) are selectively formed, and In addition, a light-emitting device capable of displaying multiple colors can be formed by combining with a color filter. By using the same, a light emitting device capable of full color display may be obtained.

[0234] Furthermore, a sealing substrate 606 is attached to the element substrate 601 with a sealing material 605. The light emitting element 6 is disposed in a space 618 surrounded by the child substrate 601, the sealing substrate 606, and the sealant 605. The space 618 is filled with an inert gas (such as nitrogen or argon). In addition to the case where the cavity is filled with a material such as a resin (such as fluorine), the cavity may also be filled with a sealant 605.

[0235] It is preferable to use an epoxy resin for the sealing material 605. It is preferable that the material is as impermeable to moisture and oxygen as possible. The materials used include glass and quartz substrates, as well as FRP (Fiberglass-Reinforced Plastics). forced plastics), PVF (polyvinyl fluoride), polyester or For the substrate, a plastic substrate made of acrylic or the like can be used.

[0236] In this manner, an active matrix light emitting device can be obtained.

[0237] Note that the structure shown in this embodiment mode may be used in appropriate combination with structures shown in other embodiment modes. It is possible.

[0238] (Embodiment 6) In this embodiment, various light emitting devices that are completed using the light emitting device according to one embodiment of the present invention will be described. An example of the child device and the lighting fixture will be described with reference to Figs. 5 to 7.

[0239] As an example of an electronic device to which a light-emitting device is applied, a television set (television or television (also called television receivers), computer monitors, digital cameras, digital video Cameras, digital photo frames, mobile phones (also called mobile phones or mobile phone devices), mobile phones These include portable game machines, mobile information terminals, audio playback devices, and large game machines such as pachinko machines. can be done.

[0240] A light-emitting element using an organometallic complex according to one embodiment of the present invention can be fabricated over a flexible substrate. In this way, it is possible to realize an electronic device or a lighting device having a light-emitting portion with a curved surface.

[0241] In addition, a pair of electrodes included in a light-emitting element using an organometallic complex according to one embodiment of the present invention is By forming the electronic device using a light-transmitting material, the electronic device has a see-through light-emitting portion. , a lighting device can be realized.

[0242] In addition, a light-emitting device to which one embodiment of the present invention is applied can also be used for automobile lighting, for example. For example, lighting can be installed on the dashboard, on the windshield, in the ceiling, etc.

[0243] Specific examples of these electronic devices and lighting fixtures are shown in FIGS.

[0244] FIG. 5A shows an example of a television device. A television device 7100 includes a housing. A display unit 7103 is built into the body 7101. The display unit 7103 displays images. It is possible to use a light-emitting device in the display portion 7103. 7, a housing 7101 is supported by a stand 7105.

[0245] The television device 7100 can be operated using an operation switch provided on the housing 7101 or a separate remote control. This can be done by the remote control operation device 7110. The channel and volume can be controlled by the 7109, and the display 7103 shows In addition, the remote control unit 7110 can control the video. A display unit 7107 for displaying information output from 7110 may be provided.

[0246] The television device 7100 includes a receiver and a modem. It is possible to receive more general television broadcasts, and furthermore, to receive them by wire or wirelessly via a modem. By connecting to a communication network, It is also possible to communicate information between followers and recipients, or between recipients themselves.

[0247] FIG. 5B shows a computer, which includes a main body 7201, a housing 7202, a display unit 7203, and a keyboard. It includes a board 7204, an external connection port 7205, a pointing device 7206, and the like. Note that the computer is manufactured using a light-emitting device for its display portion 7203.

[0248] FIG. 5C shows a portable game machine that is composed of two housings, a housing 7301 and a housing 7302. The housing 7301 is connected to the display unit 7302 by a connection part 7303 so as to be openable and closable. 304 is incorporated in the housing 7302, and a display unit 7305 is incorporated in the housing 7302. The portable gaming machine shown in (C) also has a speaker unit 7306, a recording medium insertion unit 7307, LED lamp 7308, input means (operation keys 7309, connection terminal 7310, sensor 731 1 (force, displacement, position, velocity, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemistry Material, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, (including the function of measuring odor or infrared rays), microphone 7312) Of course, the configuration of the portable gaming machine is not limited to the above, and at least the display unit 730 4 and the display portion 7305, or either one of them may use a light-emitting device. The portable game machine shown in FIG. The function of reading out the programs or data stored in the device and displaying them on the display unit, The mobile phone has a function to share information with the mobile phone shown in FIG. The functions of the gaming machine are not limited to these, and the gaming machine may have a variety of functions.

[0249] FIG. 5D shows an example of a mobile phone. A mobile phone 7400 is attached to a housing 7401. In addition to the built-in display unit 7402, operation buttons 7403, external connection port 7404, The mobile phone 7400 is equipped with a light emitting device, a microphone 7406, and the like. The display portion 7402 is fabricated by using the same.

[0250] In a mobile phone 7400 shown in FIG. 5D, information is displayed by touching a display portion 7402 with a finger or the like. You can also make a call or write an email by This can be done by touching the display portion 7402 with a finger or the like.

[0251] The screen of the display unit 7402 has three main modes. The first is a display mode that is mainly used for displaying images. The first mode is a display mode, the second is an input mode for inputting information such as characters, and the third mode is a display mode. This is a display + input mode that combines the display mode and the input mode.

[0252] For example, when making a call or composing an e-mail, the display unit 7402 is used to input characters. The main character input mode is to input characters displayed on the screen. It is preferable to display a keyboard or number buttons on most of the screen of the display portion 7402. It is.

[0253] In addition, a sensor for detecting the inclination such as a gyro or an acceleration sensor is installed inside the mobile phone 7400. By providing a detection device having the above configuration, the orientation of the mobile phone 7400 (vertical or horizontal) can be determined and the display The screen display of the display unit 7402 can be automatically switched.

[0254] The screen mode can be changed by touching the display portion 7402 or by operating the housing 7401. This is done by operating the button 7403. Also, depending on the type of image displayed on the display unit 7402, For example, the image signal to be displayed on the display unit is a moving image. If it is data, the mode is switched to display mode, and if it is text data, the mode is switched to input mode.

[0255] In the input mode, the optical sensor of the display unit 7402 detects a signal and displays If there is no input by touch operation of the part 7402 for a certain period of time, the screen mode is changed to the input mode. Alternatively, the display mode may be switched from the normal mode to the display mode.

[0256] The display portion 7402 can also function as an image sensor. By touching the palm or fingers of the user on the sensor 02 and capturing an image of the palm print or fingerprint, the user can be authenticated. In addition, a backlight that emits near-infrared light to the display unit or a sensing light source that emits near-infrared light By using this, it is possible to image finger veins, palm veins, etc.

[0257] As described above, by using the light-emitting device of one embodiment of the present invention, the display portion of an electronic device can have high light emission. In addition, by applying one embodiment of the present invention, a highly reliable In addition, by applying one embodiment of the present invention, it is possible to provide an electronic device. It is possible to create electronic devices that are

[0258] FIG. 5(E) shows a table lamp, which includes a lighting unit 7501, a shade 7502, and an adjustable arm 75 03, a support 7504, a base 7505, and a power source 7506. The lighting fixture is a ceiling-mounted lighting fixture. This also includes lighting fixtures and wall-mounted lighting fixtures.

[0259] FIG. 6A shows an example in which the light emitting device is used as an indoor lighting device 801. It can also be used for large-area lighting devices. As shown in FIG. 6A, the lighting device 802 may be used as a lighting device for indoor use. In a room equipped with the lighting device 801, the tabletop lighting device 803 described in FIG. 5(E) can be used in combination. good.

[0260] Another example of the lighting device is shown in FIG. 6B. The tabletop lighting device shown in FIG. 6B includes a lighting unit 950. The lighting unit 9501 includes an organic EL display device according to one embodiment of the present invention. In this manner, the light-emitting element of one embodiment of the present invention can be fabricated over a flexible substrate. By manufacturing the lighting device, it is possible to produce a lighting device having a curved surface or a lighting part that can be flexibly bent. In this way, the flexible light-emitting device can be used as a lighting device. This not only improves the design freedom of lighting equipment, but also makes it possible to install lighting equipment on, for example, automobile ceilings and dashboards. It is now possible to install lighting devices in places with curved surfaces, such as boards.

[0261] FIG. 7 shows an example of another lighting device. As described above, one embodiment of the present invention is applied to the lighting device having a curved surface. In addition, the organometallic complex of one embodiment of the present invention can emit light with a yellow to orange color. Since the LED emits light of a yellow color or an orange color, a yellow lighting device or an orange lighting device can be provided. One embodiment of the present invention can be applied to a lighting device 9900 for use in a tunnel as shown in FIG. By applying one aspect of the present invention, a lighting device with high luminous efficiency and energy efficiency can be realized. In addition, yellow to orange light has high visibility, which can help prevent accidents. In addition, since the lighting device to which one embodiment of the present invention is applied is a surface light source, the directivity is not excessively strong. This can prevent the vehicle from becoming unstable and reduce the causes of accidents.

[0262] The above-mentioned yellow lighting device can also be applied to a yellow room or the like. By using the lighting device according to one embodiment for lighting in a yellow room, shadows are less likely to occur and good lighting is possible. It is possible to provide a good working environment.

[0263] As described above, by using the light-emitting device of one embodiment of the present invention, the lighting device can have high emission efficiency. In addition, by applying one embodiment of the present invention, a highly reliable lighting device can be provided. In addition, by applying one embodiment of the present invention, a lighting device with low power consumption can be provided. It is possible to create a device.

[0264] As described above, the light emitting device can be used to obtain electronic devices and lighting fixtures. The range of application is extremely wide, and it can be applied to electronic devices in all fields.

[0265] Note that the structure shown in this embodiment mode may be used in appropriate combination with structures shown in other embodiment modes. It is possible. EXAMPLES

[0266] <Synthesis Example 1> In this example, an organometallic compound represented by structural formula (100) in Embodiment 1, which is one embodiment of the present invention, is used. Complexes of the group, (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 r(dppm) 2 A specific example of the synthesis of [Ir(dpp(acac)]) is given below. m) 2 The structure of (acac)] is shown below.

[0267] [ka]

[0268] <Step 1: Synthesis of 4,6-diphenylpyrimidine (abbreviation: Hdppm)> First, 5.02 g of 4,6-dichloropyrimidine, 8.29 g of phenylboronic acid, and sodium carbonate were 7.19g of palladium, bis(triphenylphosphine)palladium(II) dichloride (abbreviated Name: Pd(PPh 3 ) 2 Cl 2 ) 0.29g, water 20mL, acetonitrile 20mL, The reaction vessel was placed in a recovery flask equipped with a reflux condenser, and the inside of the flask was replaced with argon. The sample was heated by irradiating it with 2.45 GHz 100 W power for 60 minutes. Boronic acid 2.08g, sodium carbonate 1.79g, Pd(PPh 3 ) 2 Cl 2 0.07 0 g, 5 mL of water, and 5 mL of acetonitrile were placed in the flask and microwaved again (2.45 G The solution was heated by irradiating it with a 100W (100Hz) light for 60 minutes. Water was then added to the solution, and the mixture was stirred. The organic layer was extracted with chloromethane. The resulting extract was washed with water and concentrated with magnesium sulfate. The solution was dried and filtered. The solvent of the solution was removed by distillation, and the residue was The product was purified by silica gel column chromatography using dichloromethane as a developing solvent. The rimidine derivative Hdppm was obtained (yellowish white powder, 38% yield). A microwave synthesis apparatus (CEM Discover) was used for the synthesis. The synthesis scheme (a-1) is shown below.

[0269] [ka]

[0270] Step 2: Di-μ-chloro-bis[bis(4,6-diphenylpyrimidinato)iridi Ir(dppm) 2 Cl] 2 Synthesis of Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the Hdppm1 obtained in step 1 above were mixed together. .10g, Iridium chloride hydrate (IrCl 3 H 2 O) 0.69 g was added to a reflux condenser. The flask was then filled with argon. The mixture was irradiated with a 5 GHz 100 W power source for 1 hour to cause a reaction. After the solvent was removed by distillation, the resulting residue was Filtration and washing with ethanol yielded the binuclear complex [Ir(dppm) 2 Cl] 2 Got (red Brown powder, 88% yield. The synthesis scheme for step 2 (a-2) is shown below.

[0271] [ka]

[0272] Step 3: (Acetylacetonato)bis(4,6-diphenylpyrimidinato)iridide Ir(dppm) 2 Synthesis of (acac)] In addition, 40 mL of 2-ethoxyethanol and the [Ir(dppm) 2 Cl] 2 1.44g, acetylacetone 0.30g, sodium carbonate 1.07g, refluxed The flask was then filled with argon gas. The reaction was carried out by irradiating the mixture with microwaves (2.45 GHz, 120 W) for 60 minutes. The residue was dissolved in dichloromethane and filtered to remove insoluble matter. The filtrate was washed with water, then The solution was washed with saturated saline and dried over magnesium sulfate. After drying, the solution was filtered. After removing the solvent from this solution, the resulting residue was diluted with dichloromethane:ethyl acetate=50: The mixture was purified by silica gel column chromatography using 1 (volume ratio) of 1 as a developing solvent. The product was recrystallized in a mixed solvent of dichloromethane and hexane to give the desired orange powder. The compound was obtained (yield 32%). The synthesis scheme of step 3 (a-3) is shown below.

[0273] [ka]

[0274] Nuclear magnetic resonance spectroscopy of the orange powder obtained in step 3 above ( 1 H NMR Analysis Results The following is a summary of the 1 The 1 H NMR chart is shown in FIG. In the present invention, the organometallic complex [Ir( dppm) 2 (acac)] was obtained.

[0275] 1 H NMR.δ(CDCl 3 ):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, [Ir(dppm) 2 UV-visible absorption spectrum of dichloromethane solution of (acac)] The absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and the emission spectrum were measured. The spectra were measured using an ultraviolet-visible spectrophotometer (V550, manufactured by JASCO Corporation). The dichloromethane solution (0.093 mmol / L) was placed in a quartz cell and the measurement was carried out at room temperature. A fluorescence spectrometer (FS920, manufactured by Hamamatsu Photonics, Inc.) was used to measure the emission spectrum. The degassed dichloromethane solution (0.093 mmol / L) was placed in a quartz cell and heated at room temperature. The measurement results of the absorption spectrum and emission spectrum are shown in FIG. The horizontal axis represents the wavelength (nm), and the vertical axis represents the absorption intensity (arbitrary unit) and the emission intensity (arbitrary unit). In addition, two solid lines are shown in FIG. 9, the thin solid line indicates the absorption spectrum, and the thick solid line indicates the absorption spectrum. The solid line indicates the emission spectrum. Note that the absorption spectrum shown in FIG. The absorption spectrum of the dimethylformamide solution (0.093 mmol / L) in a quartz cell was The absorption spectrum measured by putting only chloromethane in a quartz cell was subtracted. There are.

[0277] As shown in FIG. 9, the organometallic complex [Ir(dppm) 2 (acac) ] has an emission peak at 592 nm, and orange emission is observed from the dichloromethane solution. was measured.

[0278] In addition, [Ir(dppm) 2 (acac)] is a material that is used for the deposition of a light-emitting element. The material did not burn during cooking, and the material was used efficiently. EXAMPLES

[0279] <Synthesis Example 2> In this example, an organometallic compound represented by structural formula (140) in Embodiment 1 is used as an embodiment of the present invention. Complex, (acetylacetonato)bis(6-methyl-4-phenylpyrimidinato)irid Umium(III) (Bis[2-(6-methyl-4-pyrimidinyl-κN3)phenyl] -κC](2,4-pentanedionato-κ 2 O,O') Iridium(III) [Ir(mppm) 2 A specific example of the synthesis of [Ir(m ppm) 2 The structure of (acac)] is shown below.

[0280] [ka]

[0281] <Step 1: Synthesis of 4-methyl-6-phenylpyrimidine (abbreviation: Hmppm)> First, 4.90 g of 4-chloro-6-methylpyrimidine, 4.80 g of phenylboronic acid, and charcoal were mixed. Sodium acetate 4.03g, Bis(triphenylphosphine)palladium(II) dichloride Pd(PPh 3 ) 2 Cl 2 ) 0.16 g, water 20 mL, acetonitrile 10 m The reaction vessel was filled with argon gas. The material was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. 2.28 g of phenylboronic acid, 2.02 g of sodium carbonate, Pd(PPh 3 ) 2 Cl 2 0.082g, 5mL of water, and 10mL of acetonitrile were placed in a flask and microwaved again ( The solution was heated by irradiating it with a 2.45 GHz 100 W power source for 60 minutes. The extract was diluted with saturated aqueous sodium carbonate, water, The solution was then washed with saturated saline and dried over magnesium sulfate. The solvent was removed from this solution, and the resulting residue was diluted with dichloromethane:ethyl acetate=9 The desired product was purified by silica gel column chromatography using a 1:1 (volume ratio) developing solvent. The pyrimidine derivative Hmppm was obtained (orange oil, 46% yield). The injection was performed using a microwave synthesis device (CEM Discover). The synthesis scheme (b-1) is shown below.

[0282] [ka]

[0283] <Step 2; Di-μ-chloro-bis[bis(6-methyl-4-phenylpyrimidinato) Iridium (III)] (abbreviation: [Ir(mppm) 2 Cl] 2 Synthesis of Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the Hmppm1 obtained in step 1 above were mixed .51g, Iridium chloride hydrate (IrCl 3 H 2 O) 1.26 g was added to a reflux condenser. The flask was then filled with argon. The mixture was irradiated with a 5 GHz 100 W power source for 1 hour to cause a reaction. After the solvent was removed by distillation, the resulting residue was The binuclear complex [Ir(mppm) 2 Cl] 2 Got (Dark green powder, 77% yield). The synthetic scheme of step 2 (b-2) is shown below.

[0284] [ka]

[0285] <Step 3; (Acetylacetonato)bis(6-methyl-4-phenylpyrimidinato) Iridium(III) (abbreviation: [Ir(mppm) 2 Synthesis of (acac)] Furthermore, 40 mL of 2-ethoxyethanol and the binuclear complex [Ir(mp pm) 2 Cl] 2 1.84g, acetylacetone 0.48g, sodium carbonate 1.73g The mixture was placed in a recovery flask equipped with a reflux condenser, and the atmosphere in the recovery flask was replaced with argon. 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 solution was washed with water, then with saturated saline, and dried over magnesium sulfate. The solution was filtered, and the solvent was removed by distillation, and the resulting residue was diluted with dichloromethane:ethyl acetate. The product was purified by silica gel column chromatography using a 4:1 (volume ratio) developing solvent. After that, the target substance was recrystallized in a mixed solvent of dichloromethane and hexane to obtain a yellow solid. It was obtained as a powder (yield 22%). The synthesis scheme of step 3 (b-3) is shown below.

[0286] [ka]

[0287] Nuclear magnetic resonance spectroscopy of the yellow powder obtained in step 3 above ( 1 H NMR Analysis Results The following is a summary of the 1 The H NMR chart is shown in FIG. In the above, the organometallic complex [Ir (mppm) 2 (acac)] was obtained.

[0288] 1 H NMR.δ(CDCl 3 ):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, [Ir(mppm) 2 UV-visible absorption spectrum of dichloromethane solution of (acac)] The absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and the emission spectrum were measured. The spectra were measured using an ultraviolet-visible spectrophotometer (V550, manufactured by JASCO Corporation). The dichloromethane solution (0.10 mmol / L) was placed in a quartz cell and the measurement was performed at room temperature. The emission spectrum was measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics, Inc.). A degassed dichloromethane solution (0.018 mmol / L) was placed in a quartz cell and heated at room temperature. The absorption spectrum and emission spectrum were measured, and the measurement results are shown in FIG. The horizontal axis represents the wavelength (nm), and the vertical axis represents the absorption intensity (arbitrary unit) and the emission intensity (arbitrary unit). In addition, two solid lines are shown in FIG. 11, the thin solid line indicates the absorption spectrum, and the thick solid line indicates the absorption spectrum. The solid line indicates the emission spectrum. From the absorption spectrum measured by putting a methane solution (0.10mmol / L) into a quartz cell, The absorption spectrum measured by putting only dichloromethane into a quartz cell was subtracted. is.

[0290] As shown in FIG. 11, the organometallic complex [Ir(mppm) 2 (aca c)] has an emission peak at 548 nm, and emits yellow-green light from a dichloromethane solution. Light was observed. EXAMPLES

[0291] <Synthesis Example 3> In this example, an organogold compound represented by structural formula (152) in Embodiment 1 is used as an embodiment of the present invention. Complexes of the group, tris(4,6-diphenylpyrimidinato)iridium(III) (also known as tris(4,6-diphenylpyrimidinato)iridium(III) Bis[2-(6-phenyl-4-pyrimidinyl-κN3)phenyl-κC]iridium(I II)) (abbreviation: [Ir(dppm) 3 A specific example of the synthesis of [Ir (dppm) 3 The structure of ] is shown below.

[0292] [ka]

[0293] 1.17 g of the ligand Hdppm obtained in Step 1 of Synthesis Example 1 above, tris(acetylacetamide) 0.49 g of cetanato(iridium(III)) was placed in a reaction vessel equipped with a three-way cock. The atmosphere in the reaction vessel was replaced with argon. Then, the reaction was carried out by heating at 250°C for 45 and a half hours. The reactant was dissolved in dichloromethane and the solution was filtered. The solvent of the obtained filtrate was distilled off to obtain cyclohexyl ether. The product was purified by silica gel column chromatography. The developing solvent was dichloromethane, followed by Ethyl acetate was used. The solvent of the obtained fraction was distilled off to obtain a red solid (yield 41 The solid was recrystallized from a mixture of dichloromethane and hexane to give the product. As a result, the target product, a red powder, was obtained (yield 11%). Shown below.

[0294] [ka]

[0295] The nuclear magnetic resonance spectroscopy of the red powder obtained above ( 1 The results of the analysis by 1 H NMR are shown below. Also, 1 The H NMR chart is shown in FIG. 12. From the results, in this Synthesis Example 3, The organometallic complex [Ir(dppm ) 3 ] was obtained.

[0296] 1 H NMR.δ(CDCl 3 ):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, [Ir(dppm) 3 The UV-visible absorption spectrum of the dichloromethane solution of The absorption spectrum (simply referred to as the "absorption spectrum") and the emission spectrum were measured. The UV-visible spectrophotometer (V550, manufactured by JASCO Corporation) was used to measure the concentration of the dichloromethane solution. The liquid (0.075 mmol / L) was placed in a quartz cell and measurements were performed at room temperature. The spectra were measured using a fluorometer (Hamamatsu Photonics FS920) in a degassed condition. The dichloromethane solution (0.075 mmol / L) was placed in a quartz cell and measurements were performed at room temperature. The results of the absorption and emission spectra are shown in Figure 13. The horizontal axis is the wavelength. (nm), and the vertical axis represents the absorption intensity (arbitrary unit) and the emission intensity (arbitrary unit). In the figure, two solid lines are shown; the thin solid line shows the absorption spectrum and the thick solid line shows the emission spectrum. The absorption spectrum shown in FIG. 13 is a dichloromethane solution. (0.075mmol / L) in a quartz cell and the absorption spectrum was measured. The results shown are those obtained by subtracting the absorption spectrum measured by putting only methane into a quartz cell.

[0298] As shown in FIG. 13, the organometallic complex [Ir(dppm) 3 ] is 5 It has an emission peak at 96 nm, and orange emission was observed from the dichloromethane solution. . EXAMPLES

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

[0300] [ka]

[0301] Step 1: Di-μ-chloro-bis[bis(4-phenylpyrimidine)iridium (I II)] (abbreviation: [Ir(ppm) 2 Cl] 2 Synthesis of First, 30 mL of 2-ethoxyethanol, 10 mL of water, and the ligand 4-phenylpyrimidine ( Abbreviation: Hppm) 0.67g, Iridium chloride (IrCl 3 HCl H 2 O) 0.50 g was placed in a three-neck flask equipped with a reflux condenser, and the atmosphere in the flask was replaced with nitrogen. The mixture was heated to reflux for 13 hours to react. The reaction solution was allowed to cool to room temperature and filtered. The collected material was washed with ethanol and the binuclear complex [Ir(ppm) 2 Cl] 2 (red powder, yield The synthesis scheme for step 1 (d-1) is shown below.

[0302] [ka]

[0303] <Step 2; (acetylacetonato)bis(4-phenylpyrimidinato)iridium ( III) (abbreviation: [Ir(ppm) 2 Synthesis of (acac)] Furthermore, 20 mL of 2-ethoxyethanol and the binuclear complex [Ir(pp m) 2 Cl] 2 0.37 g, acetylacetone 0.11 mL, sodium carbonate 0.37 g The mixture was placed in a three-neck flask equipped with a reflux condenser, and the atmosphere in the flask was replaced with nitrogen. The mixture was heated under reflux for 17.5 hours to react. The reaction solution was allowed to cool to room temperature and filtered. The solvent was removed by distillation, and the residue was purified by silica gel column chromatography using dichloromethane as a developing solvent. However, it was not possible to recover the desired iridium complex fraction. The obtained fraction was composed of the binuclear complex [Ir(ppm) 2 Cl] 2 Decomposition The synthesis scheme for step 2 (d-2) is shown below.

[0304] [ka]

[0305] As explained in this comparative example, [Ir (ppm) 2 (acac)] was difficult to synthesize. In this way, when hydrogen is bonded to the 6-position of the pyrimidine ring, the compounds exemplified in Examples 1 to 3 can be used. An organometallic complex according to one embodiment of the present invention (wherein a phenyl group is bonded to the 6-position of the pyrimidine ring) It was found that the yield was significantly lower than that of the The binuclear complex [Ir(ppm) 2 Cl] 2 This is thought to be due to the decomposition of In other words, in the organometallic complex according to one embodiment of the present invention, the decomposition reaction is suppressed during the synthesis reaction of the complex. Since it can be controlled, [Ir(ppm) 2 (acac)], the synthesis yield was dramatically improved. To rise. EXAMPLES

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

[0307] [ka]

[0308] First, 1.95 g of the ligand 4-phenylpyrimidine (abbreviation: Hppm), tris(acetyl Place 1.20 g of acetonato)iridium(III) in a reaction vessel equipped with a three-way cock. The atmosphere in the reaction vessel was replaced with argon. After that, the reaction was carried out by heating at 250°C for 41.5 hours. The reactant was dissolved in dichloromethane and the solution was filtered. The solvent of the obtained filtrate was distilled off. A residue was obtained. This residue was purified by silica gel column chromatography. The developing solvent was First, dichloromethane was used, then ethyl acetate was used. The solvent of the obtained fraction was distilled off. The brown solid was recrystallized from a mixed solvent of dichloromethane and hexane. By this, the organometallic complex [Ir(ppm) 3 A mixture containing 1,2-dichlorophenyl ether was obtained (brown powder, yield: Thin layer chromatography (TLC) of this mixture revealed a spot of brown impurity. Compare the target organometallic complex [Ir (ppm) 3 The spots are very faint and difficult to isolate. The synthesis scheme (e-1) of 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 6-position of the pyrimidine ring is hydrogen, the compounds of the present invention exemplified in Examples 1 to 3 can be used. In comparison with organometallic complexes, which are one of the most obvious examples, the yield is significantly lower or they may not be synthesized at all. That is, the organometallic complex according to one embodiment of the present invention has the following properties: Since the decomposition reaction is suppressed, [Ir(ppm) 3 The synthesis yield is dramatically improved compared to To rise. EXAMPLES

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

[0312] [ka]

[0313] A method for fabricating the light-emitting device 1 of this example will be described below.

[0314] (Light emitting element 1) First, indium tin oxide containing silicon oxide (ITSO) is deposited on a glass substrate 1100. A film was formed by a tin-sputtering method to form a first electrode 1101 that functions as an anode. The film thickness was 110 nm, and the electrode area was 2 mm × 2 mm.

[0315] As a pretreatment for forming a light-emitting element on the substrate 1100, the substrate surface is washed with water, and then After baking at 00°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0316] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside has been reduced in pressure to about Pa, and vacuum deposition is performed. After vacuum baking at 170° C. for 30 minutes in the heating chamber of the device, the substrate 1100 is It was left to cool for about 0 minutes.

[0317] Next, the surface on which the first electrode 1101 is formed is placed downward. The substrate 1100 thus formed is fixed to a substrate holder provided in a vacuum deposition apparatus, and then 10 -4 P After the pressure was reduced to about a, 4-phenyl-4'-(9-phenyl fluoren-9-yl)triphenylamine (abbreviation: BPAFLP) and molybdenum oxide ( VI) was co-evaporated to form a hole injection layer 1111. The thickness of the layer was set to 40 nm. The weight ratio of BPAFLP to molybdenum oxide was 4:2 (=BPAFLP:molybdenum oxide). The co-evaporation method is a method in which multiple evaporation sources are used in one processing chamber. This is a deposition method in which deposition is performed simultaneously from

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

[0319] In addition, 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]ky Noxalin (abbreviation: 2mDBTPDBq-II), 4-phenyl-4'-(9-phenyl -9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), and The (acetylacetonato)bis(6-methyl-4-phenylpyrimidinyl) Iridium(III) (abbreviation: [Ir(mppm) 2 (acac)]) was co-evaporated, The light-emitting layer 1113 was formed on the hole-transporting layer 1112. , PCBA1BP and [Ir(mppm) 2 (acac)] weight ratio is 0.8:0.2 :0.05(=2mDBTPDBq-II:PCBA1BP:[Ir(mppm) 2 (a cac) was adjusted. The thickness of the light-emitting layer 1113 was set to 40 nm.

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

[0321] Next, bathophenanthroline (abbreviation: BPhen) was applied onto the first electron transport layer 1114a. A film was formed to a thickness of 20 nm to form the second electron transport layer 1114b.

[0322] Furthermore, lithium fluoride (LiF) was deposited on the second electron transport layer 1114b to a thickness of 1 nm. An electron injection layer 1115 was formed by evaporation.

[0323] Finally, a 200 nm film of aluminum was deposited on the second electrode 1103, which served as the cathode. The light-emitting element 1 of this example was fabricated by depositing the material so as to have a thickness.

[0324] In the above-mentioned deposition process, the deposition was all performed by a resistance heating method.

[0325] The element structure of the thus obtained Light-emitting Element 1 is shown in Table 1.

[0326] [Table 1]

[0327] The light emitting element 1 is placed in a glove box with a nitrogen atmosphere so that the light emitting element 1 is not exposed to the air. After the sealing work was performed so as not to cause any damage to the light-emitting element 1, the operating characteristics of the light-emitting element 1 were measured. The measurements were carried out at room temperature (atmosphere maintained at 25°C).

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

[0329] [Table 2]

[0330] FIG. 18 shows the emission spectrum when a current of 0.1 mA is applied to the light-emitting element 1. In FIG. 18, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). As shown in Table 2, the emission spectrum of the light-emitting device had a peak at 544 nm. As expected, 950cd / m 2 The CIE chromaticity coordinates of light-emitting element 1 at luminance of (x,y) = (0 From this result, the light-emitting element 1 was found to have an emission efficiency of [Ir(mppm) 2 (a cac)] was obtained.

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

[0332] The above results show that high light emission can be achieved by using the organometallic complex of one embodiment of the present invention as a light-emitting material. It has been shown that it is possible to realize highly optically efficient devices.

[0333] Next, a reliability test was conducted on the light-emitting element 1. The results of the reliability test are shown in FIG. The vertical axis shows the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis shows the driving time of the element. Indicates time (h).

[0334] Reliability test: initial brightness of 5000cd / m 2 The light emitting element is set at a constant current density. Driven 1.

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

[0336] From the above results, it is possible to improve reliability by using the organometallic complex of one embodiment of the present invention as a light-emitting material. It was shown that it is possible to realize a device with high performance. EXAMPLES

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

[0338] [ka]

[0339] A method for fabricating the light-emitting device 2 of this example will be described below.

[0340] (Light emitting element 2) First, ITSO is formed as a film on a glass substrate 1100 by sputtering, and the film functions as an anode. The first electrode 1101 was formed. The thickness of the electrode was 110 nm, and the area of ​​the electrode was 2 The dimensions were 2 mm x 2 mm.

[0341] As a pretreatment for forming a light-emitting element on the substrate 1100, the substrate surface is washed with water, and then After baking at 00°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0342] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside has been reduced in pressure to about Pa, and vacuum deposition is performed. After vacuum baking at 170° C. for 30 minutes in the heating chamber of the device, the substrate 1100 is It was left to cool for about 0 minutes.

[0343] Next, the surface on which the first electrode 1101 is formed is placed downward. The substrate 1100 thus formed is fixed to a substrate holder provided in a vacuum deposition apparatus, and then 10 -4 P After the pressure was reduced to about a, BPAFLP and molybdenum oxide (VI ) was co-evaporated to form a hole injection layer 1111. The thickness of the layer was set to 40 nm. The weight ratio of PAFLP to molybdenum oxide was 4:2 (=BPAFLP:molybdenum oxide). The concentration was adjusted to be 1.

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

[0345] In addition, 2mDBTPDBq-II, 4,4'-di(1-naphthyl)-4''-(9-phenyl) (phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), and (acetylacetonato)bis(4,6-diphenylpyrimidinate) synthesized in Example 1. ) Iridium(III) (abbreviation: [Ir(dppm) 2 (acac)]) was co-evaporated, and the positive The light-emitting layer 1113 was formed on the hole transport layer 1112. PCBNBB and [Ir(dppm) 2 (acac)] weight ratio is 0.8:0.2:0 .05(=2mDBTPDBq-II:PCBNBB:[Ir(dppm) 2 (acac )) The thickness of the light-emitting layer 1113 was set to 40 nm.

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

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

[0348] Furthermore, LiF was evaporated onto the second electron transport layer 1114b to a thickness of 1 nm to form an electron injection layer. 1115 was formed.

[0349] Finally, a 200 nm film of aluminum was deposited on the second electrode 1103, which served as the cathode. The light-emitting element 2 of this example was fabricated by vapor deposition so as to have a thickness.

[0350] In the above-mentioned deposition process, the deposition was all performed by a resistance heating method.

[0351] The element structure of the thus obtained Light-emitting Element 2 is shown in Table 3.

[0352] [Table 3]

[0353] The light emitting element 2 is placed in a glove box with a nitrogen atmosphere so that the light emitting element 2 is not exposed to the air. After the sealing work was performed so as to prevent the light-emitting element 2 from being damaged, the operating characteristics of the light-emitting element 2 were measured. The measurements were carried out at room temperature (atmosphere maintained at 25°C).

[0354] FIG. 20 shows the current density-luminance characteristics of the light-emitting element 2. In FIG. 20, the horizontal axis indicates the current density (m A / cm 2 ) and the vertical axis is luminance (cd / m 2 The voltage-luminance characteristics are shown in Figure 21. In Figure 21, the horizontal axis represents voltage (V) and the vertical axis represents luminance (cd / m 2 ) and also represents brightness. The luminance-current efficiency characteristics are shown in FIG. 22. In FIG. 22, the horizontal axis is the luminance (cd / m 2 ) on the vertical axis represents the current efficiency (cd / A). The luminance vs. external quantum efficiency characteristics are shown in Figure 25. In this figure, the horizontal axis is luminance (cd / m 2 ) and the vertical axis indicates external quantum efficiency (%).

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

[0356] [Table 4]

[0357] FIG. 23 shows the emission spectrum when a current of 0.1 mA is applied to the light-emitting element 2. In FIG. 23, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). As shown in Table 4, the emission spectrum of the light-emitting device had a peak at 579 nm. As expected, 1100cd / m 2 The CIE chromaticity coordinates of light-emitting element 2 at the luminance of are (x,y) = ( 0.54, 0.46). From this result, the light-emitting element 2 had an 2 ( It was found that orange luminescence originating from the cation (acac) was obtained.

[0358] As can be seen from FIGS. 20 to 22 and 25 and Table 4, the light-emitting element 2 has good luminous efficiency. In particular, the light-emitting element 2 had an average brightness of 1100 cd / m 2 The external quantum efficiency at a brightness of 2 The light extraction efficiency of organic EL elements is 20% to 30%. 0%, so the absorption of the upper and lower electrodes must be taken into consideration (the above light extraction efficiency is approximately If we assume that the efficiency decreases by 10%, the limit of external quantum efficiency should be around 25% at most. However, the results of this study exceed those results, proving that the conventional theoretical value of light extraction efficiency is incorrect. In other words, this suggests that the theoretical value of the light extraction efficiency is incorrect. By using the organometallic complex of one embodiment of the present invention, a highly efficient light-emitting element not previously available can be realized. It can be achieved.

[0359] The above results show that the use of the organometallic complex of one embodiment of the present invention as a light-emitting material provides high It has been shown that it is possible to realize devices with high luminous efficiency.

[0360] Next, a reliability test was conducted on the light-emitting element 2. The results of the reliability test are shown in FIG. The vertical axis shows the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis shows the driving time of the element. Indicates time (h).

[0361] Reliability test: initial brightness of 5000cd / m 2 The light emitting element is set at a constant current density. Driven 2.

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

[0363] From the above results, it is clear that the use of the organometallic complex of one embodiment of the present invention as a light-emitting material can provide reliable It was shown that it is possible to realize highly efficient elements. EXAMPLES

[0364] In this example, a light-emitting element of one embodiment of the present invention will be described with reference to FIG. The materials used in Example 6 or 7 are the same as those used in Example 6 or 7, and therefore the chemical formulas thereof are omitted.

[0365] A method for fabricating the light emitting device 3 of this example will be described below.

[0366] (Light emitting element 3) First, ITSO is formed as a film on a glass substrate 1100 by sputtering, and the film functions as an anode. The first electrode 1101 was formed. The thickness of the electrode was 110 nm, and the area of ​​the electrode was 2 The dimensions were 2 mm x 2 mm.

[0367] As a pretreatment for forming a light-emitting element on the substrate 1100, the substrate surface is washed with water, and then After baking at 00°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0368] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside has been reduced in pressure to about Pa, and vacuum deposition is performed. After vacuum baking at 170° C. for 30 minutes in the heating chamber of the device, the substrate 1100 is It was left to cool for about 0 minutes.

[0369] Next, the surface on which the first electrode 1101 is formed is placed downward. The substrate 1100 thus formed is fixed to a substrate holder provided in a vacuum deposition apparatus, and then 10 -4 P After the pressure was reduced to about a, BPAFLP and molybdenum oxide (VI ) was co-evaporated to form a hole injection layer 1111. The thickness of the layer was set to 40 nm. The weight ratio of PAFLP to molybdenum oxide was 4:2 (=BPAFLP:molybdenum oxide). The concentration was adjusted to be 1.

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

[0371] Furthermore, 2mDBTPDBq-II, PCBA1BP, and [Ir( dppm) 2 (acac)] was co-evaporated 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 2mDBTPDBq-II to PCacac was 0.8:0.2:0.1 (=2mDBTPDBq-II:PCac). BA1BP:[Ir(dppm) 2 (acac)]). The thickness of the layer 1113 was set to 40 nm.

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

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

[0374] Furthermore, LiF was evaporated onto the second electron transport layer 1114b to a thickness of 1 nm to form an electron injection layer. 1115 was formed.

[0375] Finally, a 200 nm film of aluminum was deposited on the second electrode 1103, which served as the cathode. The light-emitting element 3 of this example was fabricated by depositing the material so as to have a thickness.

[0376] In the above-mentioned deposition process, the deposition was all performed by a resistance heating method.

[0377] The element structure of the thus obtained Light-emitting Element 3 is shown in Table 5.

[0378] [Table 5]

[0379] The light emitting element 3 is placed in a glove box with a nitrogen atmosphere so that the light emitting element 3 is not exposed to the air. After the sealing work was performed so as to prevent the light-emitting element 3 from being damaged, the operating characteristics of the light-emitting element 3 were measured. The measurements were carried out at room temperature (atmosphere maintained at 25°C).

[0380] FIG. 26 shows the current density-luminance characteristics of the light-emitting element 3. In FIG. 26, the horizontal axis indicates the current density (m A / cm 2 ) and the vertical axis is luminance (cd / m 2 The voltage-luminance characteristics are shown in Figure 27. In Figure 27, the horizontal axis represents voltage (V) and the vertical axis represents luminance (cd / m 2 ) and also represents brightness. The luminance-current efficiency characteristics are shown in FIG. 28. In FIG. 28, the horizontal axis is the luminance (cd / m 2 ) on the vertical axis represents the current efficiency (cd / A). The luminance vs. external quantum efficiency characteristics are shown in Figure 31. In this figure, the horizontal axis is luminance (cd / m 2 ) and the vertical axis indicates external quantum efficiency (%).

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

[0382] [Table 6]

[0383] FIG. 29 shows the emission spectrum when a current of 0.1 mA is applied to the light-emitting element 3. In FIG. 29, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). As shown in Table 6, the emission spectrum of the light-emitting device had a peak at 586 nm. As expected, 1100cd / m 2 The CIE chromaticity coordinates of light-emitting element 3 at the luminance of 0.57, 0.43). From this result, the light-emitting element 3 had an 2 ( It was found that orange luminescence originating from the cation (acac) was obtained.

[0384] As can be seen from FIGS. 26 to 28, 31, and Table 6, the light-emitting element 3 has good luminous efficiency. In particular, the light-emitting element 3 had a luminance of 1100 cd / m 2 The external quantum efficiency at a brightness of 3 The light extraction efficiency of organic EL elements is 20% to 30%. 0%, so the absorption of the upper and lower electrodes must be taken into consideration (the above light extraction efficiency is approximately If we assume that the efficiency decreases by 10%, the limit of external quantum efficiency should be around 25% at most. However, the results of this study exceed those results, proving that the conventional theoretical value of light extraction efficiency is incorrect. In other words, this suggests that the theoretical value of the light extraction efficiency is incorrect. By using the organometallic complex of one embodiment of the present invention, a highly efficient light-emitting element not previously available can be realized. It can be achieved.

[0385] The above results show that the use of the organometallic complex of one embodiment of the present invention as a light-emitting material provides high It has been shown that it is possible to realize devices with high luminous efficiency.

[0386] Next, a reliability test was conducted on the light-emitting element 3. The results of the reliability test are shown in FIG. The vertical axis shows the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis shows the driving time of the element. Indicates time (h).

[0387] Reliability test: initial brightness of 5000cd / m 2 The light emitting element is set at a constant current density. Driven 3.

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

[0389] From the above results, it is clear that the use of the organometallic complex of one embodiment of the present invention as a light-emitting material can provide reliable It was shown that it is possible to realize highly efficient elements.

[0390] Note that in Example 8, the amount of the organometallic complex of one embodiment of the present invention in the light-emitting layer was smaller than that in Example 7. The doping concentration is high. As a result, the device of Example 8 has a higher emission spectrum than the device of Example 7. However, the external quantum efficiency values ​​are In this way, the organometallic compound according to one embodiment of the present invention has high reliability. By changing the concentration of the complex added to the light-emitting layer, the light-emitting efficiency and reliability of the device can be reduced. One of the features of one embodiment of the present invention is that the color tone of emitted light can be changed without changing the color tone of the light. It is. EXAMPLES

[0391] <Synthesis Example 4> In this example, an organogold compound represented by structural formula (190) in Embodiment 1 is used as an embodiment of the present invention. Complex, (acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidina Bis[2-(6-tert-butyl-4-pyrimidinium(III)] 1,3-Diphenyl-κC](2,4-pentanedionato-κN3)phenyl-κC 2 O,O') Iridium (III)) (abbreviation: [Ir(tBuppm) 2 A specific example of the synthesis of (acac)] Note that [Ir(tBuppm) 2 The structure of (acac)] is shown below.

[0392] [ka]

[0393] <Step 1: 4-tert-butyl-6-phenylpyrimidine (abbreviation: HtBuppm Synthesis of First, 22.5 g of 4,4-dimethyl-1-phenylpentane-1,3-dione and formaldehyde were 50 g of mide was placed in a recovery flask equipped with a reflux condenser, and the inside of the flask was replaced with nitrogen. The reaction solution was refluxed for 5 hours by heating. Then, the solution was diluted with sodium hydroxide solution. The organic layer was extracted with dichloromethane. The organic layer was washed with water and saturated saline. The solution was washed and dried over magnesium sulfate. The solution after drying was filtered. After removing the solvent, the residue was dissolved in hexane and ethyl acetate (volume ratio: 10:1) and The pyrimidine derivative HtBupp was purified by silica gel column chromatography using a solvent. m was obtained (colorless oil, 14% yield). The synthesis scheme of step 1 is shown below in (f-1). vinegar.

[0394] [ka]

[0395] <Step 2: Di-μ-chloro-bis[bis(6-tert-butyl-4-phenylpyridine] Iridium(III) 2 Cl] 2 Synthesis of > Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the HtBupp obtained in step 1 above were added. m1.49g, iridium chloride hydrate (IrCl 3 H 2 1.04 g of O) was added to a reflux condenser. The flask was then filled with argon gas. The mixture was irradiated with a 5 GHz 100 W power source for 1 hour to cause a reaction. After the solvent was removed by distillation, the resulting residue was The binuclear complex [Ir(tBuppm) 2 Cl] 2 Obtained (yellow Green powder, 73% yield). The synthesis scheme of step 2 is shown below in (f-2).

[0396] [ka]

[0397] <Step 3; (acetylacetonato)bis(6-tert-butyl-4-phenylpyridine) Iridium(III) (abbreviation: [Ir(tBuppm) 2 (acac)] > Furthermore, 40 mL of 2-ethoxyethanol and the binuclear complex [Ir(tB uppm) 2 Cl] 2 1.61g, acetylacetone 0.36g, sodium carbonate 1. 27 g was placed in a recovery flask equipped with a reflux condenser, and the atmosphere in the flask was replaced with argon. The mixture was then irradiated with microwaves (2.45 GHz, 120 W) for 60 minutes to react. The solvent was removed by distillation. The resulting residue was filtered with ethanol and washed with water and ethanol. Dissolve in chloromethane and filter with Celite (Wako Pure Chemical Industries, Ltd., Catalog No. 531-1 The mixture was filtered through a filter aid consisting of a layer of 6855), alumina, and celite in that order. The solid obtained by removing the residue was recrystallized in a mixed solvent of dichloromethane and hexane to give The target product was obtained as a yellow powder (yield 68%). The synthesis scheme of step 3 is shown below (f-3 ) as shown in

[0398] [ka]

[0399] Nuclear magnetic resonance spectroscopy of the yellow powder obtained in step 3 above ( 1 H NMR Analysis Results The following is a summary of the 1 The H NMR chart is shown in FIG. In the above, an organometallic complex represented by the structural formula ((190)) according to one embodiment of the present invention [ Ir(tBuppm) 2 (acac)] was obtained.

[0400] 1 H NMR.δ(CDCl 3 ):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, [Ir(tBuppm) 2 UV-visible absorption spectra of dichloromethane solution of (acac)] The absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and the emission spectrum were measured. The spectrum was measured using an ultraviolet-visible spectrophotometer (V550, manufactured by JASCO Corporation). The dichloromethane solution (0.093 mmol / L) was placed in a quartz cell and measurements were performed at room temperature. The emission spectrum was measured using a fluorometer (Hamamatsu Photonics FS920). ) was used, and a degassed dichloromethane solution (0.093 mmol / L) was placed in a quartz cell. The measurements were carried out at room temperature. The results of the absorption and emission spectra are shown in Figure 33. The horizontal axis represents the wavelength (nm), and the vertical axis represents the absorption intensity (arbitrary unit) and emission intensity (arbitrary unit). In addition, two solid lines are shown in Figure 33, and the thin solid line shows the absorption spectrum. The thick solid line indicates the emission spectrum. Absorption spectrum measured in a chloromethane solution (0.093mmol / L) in a quartz cell The absorption spectrum of only dichloromethane in the quartz cell was subtracted from that of the The results are shown.

[0402] As shown in FIG. 33, the organometallic complex [Ir(tBuppm) 2 (ac ac)] has an emission peak at 547 nm and emits a yellow-green light from a dichloromethane solution. Luminescence was observed. EXAMPLES

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

[0404] [ka]

[0405] A method for fabricating the light-emitting device 4 of this example will be described below.

[0406] (Light emitting element 4) First, ITSO was formed as a film on a glass substrate 1100 by sputtering, and the film served as an anode. The first electrode 1101 was formed. The thickness of the electrode was 110 nm, and the area of ​​the electrode was 2 The dimensions were 2 mm x 2 mm.

[0407] As a pretreatment for forming a light-emitting element on the substrate 1100, the substrate surface is washed with water, and then After baking at 00°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0408] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside has been reduced in pressure to about Pa, and vacuum deposition is performed. After vacuum baking at 170° C. for 30 minutes in the heating chamber of the device, the substrate 1100 is It was left to cool for about 0 minutes.

[0409] Next, the surface on which the first electrode 1101 is formed is placed downward. The substrate 1100 thus formed is fixed to a substrate holder provided in a vacuum deposition apparatus, and then 10 -4 P After the pressure was reduced to about a, BPAFLP and molybdenum oxide (VI ) was co-evaporated to form a hole injection layer 1111. The thickness of the layer was set to 40 nm. The weight ratio of PAFLP to molybdenum oxide was 4:2 (=BPAFLP:molybdenum oxide). The concentration was adjusted to be 1.

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

[0411] In addition, 2mDBTPDBq-II, PCBA1BP, and the acetylated ... ruacetonato)bis(6-tert-butyl-4-phenylpyrimidinato)iridium( III) (Abbreviation: [Ir(tBuppm) 2 (acac)]) was co-evaporated to form a hole transport layer 1 An emitting layer 1113 was formed on the substrate 112. BP and [Ir(tBuppm) 2 (acac)] weight ratio is 0.8:0.2:0.0 75(=2mDBTPDBq-II:PCBA1BP:[Ir(tBuppm) 2 (ac The thickness of the light-emitting layer 1113 was adjusted to 40 nm.

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

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

[0414] Furthermore, LiF was evaporated onto the second electron transport layer 1114b to a thickness of 1 nm to form an electron injection layer. 1115 was formed.

[0415] Finally, a 200 nm film of aluminum was deposited on the second electrode 1103, which served as the cathode. The light-emitting element 4 of this example was fabricated by depositing the material so as to have a thickness.

[0416] In the above-mentioned deposition process, the deposition was all performed by a resistance heating method.

[0417] The element structure of the thus obtained Light-emitting Element 4 is shown in Table 7.

[0418] [Table 7]

[0419] The light emitting element 4 is placed in a glove box with a nitrogen atmosphere so that the light emitting element 4 is not exposed to the air. After the sealing work was performed so as to prevent the light-emitting element 4 from being damaged, the operating characteristics of the light-emitting element 4 were measured. The measurements were carried out at room temperature (atmosphere maintained at 25°C).

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

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

[0422] [Table 8]

[0423] FIG. 37 shows the emission spectrum when a current of 0.1 mA is applied to the light-emitting element 4. In FIG. 37, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). As shown in Table 8, the emission spectrum of the light-emitting device had a peak at 546 nm. As expected, 1100cd / m 2 The CIE chromaticity coordinates of light-emitting element 4 at the luminance of 0.44, 0.55). From this result, it can be seen that the light-emitting element 4 has an 2 It was found that orange luminescence originating from the cation exchange reaction (cation (acac)) was obtained.

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

[0425] The above results show that the use of the organometallic complex of one embodiment of the present invention as a light-emitting material provides high It has been shown that it is possible to realize devices with high luminous efficiency. EXAMPLES

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

[0427] [ka]

[0428] A method for fabricating the light emitting device 5 of this example will be described below.

[0429] (Light emitting element 5) First, ITSO is formed as a film on a glass substrate 1100 by sputtering, and the film functions as an anode. The first electrode 1101 was formed. The thickness of the electrode was 110 nm, and the area of ​​the electrode was 2 The dimensions were 2 mm x 2 mm.

[0430] As a pretreatment for forming a light-emitting element on the substrate 1100, the substrate surface is washed with water, and then After baking at 00°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 whose inside has been reduced in pressure to about Pa. After vacuum baking at 170° C. for 30 minutes in a heating chamber in a vacuum deposition apparatus, the substrate 11 00 was left to cool for about 30 minutes.

[0432] Next, the surface on which the first electrode 1101 is formed is placed downward. The substrate 1100 thus formed is fixed to a substrate holder provided in a vacuum deposition apparatus, and then 10 -4 P After reducing the pressure to about a, 9-phenyl-3-[4-(10-phenyl)- (phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA) and oxidation Molybdenum (VI) was co-evaporated to form the first hole injection layer 1111a. The film thickness was 60 nm, and the weight ratio of PCzPA to molybdenum oxide was 1:0.5 (= The composition was adjusted to be PCzPA: molybdenum oxide).

[0433] Next, a film of PCzPA was formed on the first hole injection layer 1111a to a thickness of 30 nm. Thus, a first hole transport layer 1112a was formed.

[0434] Further, on the first hole transport layer 1112a, 9-[4-(N-carbazolyl)]phenyl -10-phenylanthracene (abbreviation: CzPA) and N,N'-bis(3-methylphenyl N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl] -pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn) was co-evaporated. The first light-emitting layer 1113a was formed by the above steps. The thickness of the layer was set to 30 nm. The ratio of CzPA to 1,6 mMemFLPAPrn was 1:0.05 by weight (=CzPA:1,6 mMemFLPAPrn). The concentration of FLPAPrn was adjusted to be 1.

[0435] Next, on the first light-emitting layer 1113a, CzPA was deposited to a thickness of 5 nm, and BPhen was deposited to a thickness of 15 nm. A film was formed so as to form a first electron-transporting layer 1114a.

[0436] Then, lithium oxide (Li 2 O) 0.1 nm film A first electron injection layer 1115a was formed by vapor deposition to a thickness of 1115mm.

[0437] Then, copper phthalocyanine (abbreviation: CuPc) was deposited to a thickness of 1115a on the first electron injection layer 1115a. A 2 nm thick film was deposited to form a first intermediate layer 1116a.

[0438] Next, PCzPA and molybdenum (VI) oxide are co-deposited on the first intermediate layer 1116a. The second hole injection layer 1111b was formed by the above process. The weight ratio of PCzPA to molybdenum oxide was 1:0.5 (=PCzPA:molybdenum oxide). It was adjusted so that

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

[0440] Then, on the second hole transport layer 1112b, 2mDBTPDBq-II, PCBA1BP , and [Ir(dppm) 2 (acac)] was co-evaporated to form the first The light-emitting layer 1113b was formed with a thickness of 40 nm. I, PCBA1BP, and [Ir(dppm) 2 (acac)] by weight is 0. 8:0.2:0.06(=2mDBTPDBq-II:PCBA1BP:[Ir(dpp m) 2 (acac)]).

[0441] Next, 2mDBTPDBq-II was deposited to a thickness of 15 nm on the second light-emitting layer 1113b. A film of en was formed to a thickness of 15 nm to form the second electron-transporting layer 1114b.

[0442] Then, on the second electron transport layer 1114b, Li 2O was evaporated to a thickness of 0.1 nm, and the second An electron injection layer 1115b was formed.

[0443] Then, CuPc was evaporated onto the second electron injection layer 1115b to a thickness of 2 nm. A layer 1116b was formed.

[0444] Next, PCzPA and molybdenum (VI) oxide are co-deposited on the second intermediate layer 1116b. The third hole injection layer 1111c was formed by the above process. The weight ratio of PCzPA to molybdenum oxide was 1:0.5 (=PCzPA:molybdenum oxide). It was adjusted so that

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

[0446] Then, a third light-emitting layer 1113c and a third electron transport layer 1114c are formed on the third hole transport layer 1112c. The third light-emitting layer 1113c and the third electron-transporting layer 1114c were then formed. 4c are similar to the second light-emitting layer 1113b and the second electron-transporting layer 1114b, respectively. Formed in composition.

[0447] Next, LiF was evaporated onto the third electron transport layer 1114c to a thickness of 1 nm. An inlet layer 1115c was formed.

[0448] Finally, a second electrode 1103 functioning as a cathode was formed on the third electron injection layer 1115c. Then, aluminum was evaporated to a thickness of 200 nm to form the light-emitting element of this embodiment. 5 was produced.

[0449] In the above-mentioned deposition process, the deposition was all performed by a resistance heating method.

[0450] The element structure of the thus obtained Light-emitting element 5 is shown in Table 9.

[0451] [Table 9]

[0452] The light emitting element 5 is placed in a glove box with a nitrogen atmosphere so that the light emitting element 5 is not exposed to the air. After the sealing work was performed so as not to cause any damage to the light-emitting element 5, the operating characteristics of the light-emitting element 5 were measured. The measurements were carried out at room temperature (atmosphere maintained at 25°C).

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

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

[0455] [Table 10]

[0456] FIG. 42 shows the emission spectrum when a current of 0.1 mA is applied to the light-emitting element 5. In FIG. 43, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). As shown in Table 10, the emission spectrum of the light-emitting device had a peak at 581 nm. As shown, 4700cd / m 2 The CIE chromaticity coordinates of the light-emitting element 5 at the luminance of (x,y) = (0.49, 0.42).

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

[0458] The above results show that the use of the organometallic complex of one embodiment of the present invention as a light-emitting material provides high It has been shown that it is possible to realize devices with high luminous efficiency.

[0459] Next, a reliability test was conducted on the light-emitting element 5. The results of the reliability test are shown in FIG. The vertical axis shows the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis shows the driving time of the element. Indicates time (h).

[0460] Reliability test: initial brightness of 5000cd / m 2 The light emitting element is set at a constant current density. Driven 5.

[0461] After 320 hours, the luminance of the light-emitting element 5 remained at 95% of the initial luminance.

[0462] Furthermore, a luminance acceleration test was performed on the light-emitting element 5. Initial brightness of the element is 20,000 cd / m 2 , 30000cd / m 2 , 40000cd / m 2 , 50000cd / m 2 , 70000cd / m 2 , and 100,000 cd / m 2 Each The brightness was set at 1000 mA and a constant current test was performed. The initial brightness was then calculated from the correlation plot of initial brightness vs. lifespan. degree 5000cd / m 2 In this example, the lifetime of the light-emitting element was estimated. The time it takes for a child to reach less than 70% of its initial luminance.

[0463] A correlation plot of initial brightness vs. lifetime is shown in FIG. 44. In FIG. 44, the vertical axis represents lifetime (h). The horizontal axis indicates initial luminance (cd / m 2 ) with an initial luminance of 20,000 cd / m 2 , 30000cd / m 2 Since the brightness has not yet reached 70% of the initial brightness, the deterioration curve From this result, the initial luminance of the light-emitting element 5 was 5000 cd / m 2 The lifetime of the element is estimated at 30,000 hours, proving that it is an extremely long-life element. Ta.

[0464] From the above results, it is clear that the use of the organometallic complex of one embodiment of the present invention as a light-emitting material can provide reliable It was shown that it is possible to realize highly efficient elements. EXAMPLES

[0465] <Synthesis Example 5> In this example, an organometallic compound represented by structural formula (101) in Embodiment 1 is used as an embodiment of the present invention. Complex of the group, bis(4,6-diphenylpyrimidinato)(dipivaloylmethanato)iridium (III) (synonym: (2,2,6,6-tetramethyl-3,5-heptanedionato-κ 2 O,O')bis[2-(6-phenyl-4-pyrimidinyl-κN3)phenyl-κC]iso Ir(dppm) 2 A concrete example of the synthesis of (dpm)] Here is an example: [Ir(dppm) 2 The structure of (dpm)] is shown below.

[0466] [ka]

[0467] First, 30 mL of 2-ethoxyethanol and the binuclear complex [Ir( dppm) 2 Cl] 2 1.93g, dipivaloylmethane 0.77g, sodium carbonate 1. 51 g was placed in a recovery flask equipped with a reflux condenser, and the atmosphere in the flask was replaced with argon. The mixture was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. Further, 0.26 g of dipivaloylmethane was added to the flask and the microwave (2.45 GHz) was again applied. The mixture was heated by irradiation with a 100 W power source for 60 minutes. The solvent was removed by distillation, and the resulting residue was The mixture was dissolved in hexane and filtered to remove insoluble matter. The filtrate was washed with water and saturated saline. The solution was filtered and the solvent was distilled off. The residue was then washed with toluene. The solid was recrystallized from the solvent to obtain a red solid (yield 28%, purity 95%). The product was purified by silica gel column chromatography using methane as a developing solvent. The product was recrystallized from a mixed solvent of dichloromethane and hexane to obtain a red powder (yield 6%). The synthesis scheme (g-1) is shown below.

[0468] [ka]

[0469] Nuclear magnetic resonance spectroscopy of the resulting red powder ( 1 The results of the analysis by 1 H NMR are shown below. Ta, 1 The H NMR chart is shown in Figure 45. From this, it is apparent that in this Synthesis Example 5, An organometallic complex according to one embodiment of the present invention, represented by structural formula (101) [Ir(dppm) 2 (dp m)] was obtained.

[0470] 1 H NMR.δ(CDCl 3 ):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, [Ir(dppm) 2 UV-visible absorption spectrum of dichloromethane solution of (dpm)] The absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and the emission spectrum were measured. The measurement of the torr was performed using an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation). The fluoromethane solution (0.080 mmol / L) was placed in a quartz cell and the measurement was carried out at room temperature. The emission spectrum was measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics, Inc.). A degassed dichloromethane solution (0.080 mmol / L) was placed in a quartz cell and heated at room temperature. The measurement results of the absorption spectrum and emission spectrum are shown in FIG. The horizontal axis represents the wavelength (nm), and the vertical axis represents the absorption intensity (arbitrary unit) and the emission intensity (arbitrary unit). In addition, two solid lines are shown in FIG. 46, the thin solid line indicates the absorption spectrum, and the thick solid line indicates the absorption spectrum. The solid line indicates the emission spectrum. From the absorption spectrum measured by putting a methane solution (0.080mmol / L) in a quartz cell, The absorption spectrum measured by putting only dichloromethane into a quartz cell was subtracted from the results shown. is doing.

[0472] As shown in FIG. 46, the organometallic complex [Ir(dppm) 2 (dpm)] is It has an emission peak at 610 nm, and red-orange emission is observed from the dichloromethane solution. It was done. EXAMPLES

[0473] <Synthesis Example 6> In this example, an organometallic compound represented by structural formula (114) in Embodiment 1 is used as an embodiment of the present invention. Complexes of the acetylacetonato group, bis[4,6-di(naphthalene-2-yl)pyrimidina] Bis[3-(6-naphthalene-2-yl-4-pyrimidium(III)] 2,4-Pentanedionato-κN3)-2-naphthalenyl-κC 2 O,O ') Iridium (III) (abbreviation: [Ir(d2npm) 2 Synthesis example of (acac)] Here is a specific example: [Ir(d2npm) 2 The structure of (acac)] is shown below: .

[0474] [ka]

[0475] <Step 1; Synthesis of 4-chloro-6-(naphthalen-2-yl)pyrimidine> First, 5.0 g of 4,6-dichloropyrimidine, 11.7 g of 2-naphthaleneboronic acid, and carbonic acid Sodium 7.2g, Bis(triphenylphosphine)palladium(II) dichloride ( Abbreviation: Pd(PPh 3 ) 2 Cl 2 0.29 g, 20 mL of water, and 20 mL of acetonitrile The reaction vessel was placed in a recovery flask equipped with a reflux condenser, and the inside of the vessel was replaced with argon. The mixture was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. Naphthaleneboronic acid 2.9g, sodium carbonate 1.8g, Pd(PPh 3 ) 2 Cl 2 0. Add 070g of water, 5mL of water, and 5mL of acetonitrile to the flask and microwave again (2.4 The solution was heated by irradiating it with a 5 GHz 100 W power source for 60 minutes. Water was then added to the solution, and The organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and then with magnesium sulfate. The solution was then filtered. The solvent was removed by distillation, and the resulting residue was The residue was subjected to silica gel column chromatography using hexane:ethyl acetate=5:1 as a developing solvent. The desired pyrimidine derivative, 4-chloro-6-(naphthalene-2-yl)pyrimidine, was obtained. The resulting product was a yellowish white powder, yield 48%. Microwave irradiation was performed using a microwave synthesis apparatus. The synthesis scheme for step 1 (h- 1) is shown.

[0476] [ka]

[0477] <Step 2; 4,6-di(naphthalen-2-yl)pyrimidine (abbreviation: Hd2npm) Synthesis of > Next, 4-chloro-6-(naphthalen-2-yl)pyrimidine 3 obtained in step 1 above. 9g, 2-naphthaleneboronic acid 2.8g, sodium carbonate 1.7g, bis(triphenyl Pd(PPh)palladium(II) dichloride 3 ) 2 Cl 2 ) 0.1 Put 4g of ethanol, 20mL of water, and 20mL of acetonitrile into a round-bottom flask equipped with a reflux condenser. The atmosphere in the reaction vessel was replaced with argon. The mixture was heated by irradiating for 1 min. Here, 1.4 g of 2-naphthaleneboronic acid and sodium carbonate were added. 0.9g, Pd(PPh 3 ) 2 Cl 2 0.070g, 5mL water, 5m acetonitrile Put L into the flask and irradiate with microwaves (2.45GHz, 100W) again for 60 minutes. After that, water was added to the solution, and the organic layer was extracted with dichloromethane. The organic layer was washed with water and dried over magnesium sulfate. The dried solution was filtered. The solvent was removed from this solution, and the resulting residue was extracted with hexane:ethyl acetate=5:1. The desired pyrimidine derivative H was obtained by purification using flash column chromatography with the open solvent. d2npm was obtained (yellowish white powder, 19% yield). The synthesis scheme for step 2 (h- 2) is shown.

[0478] [ka]

[0479] <Step 3: Di-μ-chloro-bis{bis[4,6-di(naphthalen-2-yl)pyridine] {Ir(d2npm)} 2 Cl] 2 Synthesis of Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the Hd2npm obtained in step 2 above were added to 1.00g, Iridium chloride hydrate (IrCl 3 H 2 O) (Sigma-Aldric (H Company) 0.44 g was placed in a recovery flask equipped with a reflux condenser, and the flask was purged with argon. Then, the mixture was irradiated with microwaves (2.45 GHz, 100 W) for 1 hour to cause a reaction. After the solvent was removed, the residue was filtered and washed with ethanol to give the binuclear complex [Ir(d 2npm) 2 Cl] 2 (Brown powder, 98% yield) This shows h-3.

[0480] [ka]

[0481] <Step 4; (acetylacetonato)bis[4,6-di(naphthalen-2-yl)pyridine] [Ir(d2npm) 2 Synthesis of (acac)] > In addition, 30 mL of 2-ethoxyethanol and the binuclear complex [Ir(d npm) 2 Cl] 2 1.28g, acetylacetone 0.22g, sodium carbonate 0.76 g was placed in a recovery flask equipped with a reflux condenser, and the atmosphere in the flask was replaced with argon. The material was heated by irradiating it with microwaves (2.45 GHz, 120 W) for 60 minutes. 0.22 g of acetylacetone was placed in the flask and the mixture was again heated in a microwave oven (2.45 GHz 12 The mixture was heated by irradiation with 100 W for 60 minutes. The solvent was removed, and the resulting residue was washed with ethanol. The solid was filtered by suction and washed with water, ethanol, and dichloromethane. Dissolve in toluene and filter through a filter aid made of layers of Celite, alumina, and Celite in that order. After filtration, the mixture was recrystallized in a mixed solvent of toluene and hexane to obtain a red powder. Yield 11%). The synthetic scheme for step 4 (h-4) is shown below.

[0482] [ka]

[0483] Nuclear magnetic resonance spectroscopy of the resulting red powder ( 1 The results of the analysis by 1 H NMR are shown below. Ta, 1 The H NMR chart is shown in Figure 47. From this, it is apparent that in this Synthesis Example 6, An organometallic complex according to one embodiment of the present invention, represented by structural formula (114) [Ir(dnpm) 2 (a 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 .95(s,2H),9.24-9.27(m,6H).

[0485] Next, [Ir(d2npm)2 UV-visible absorption spectrum of dichloromethane solution of (acac)] The absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and the emission spectrum were measured. The spectrum was measured using an ultraviolet-visible spectrophotometer (V550, manufactured by JASCO Corporation). The chloromethane solution (0.073 mmol / L) was placed in a quartz cell, and measurements were performed at room temperature. The emission spectrum was measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics, Inc.). A degassed dichloromethane solution (0.073 mmol / L) was placed in a quartz cell. The measurement results of the absorption spectrum and emission spectrum are shown in Figure 48. The horizontal axis represents the wavelength (nm), and the vertical axis represents the absorption intensity (arbitrary unit) and emission intensity (arbitrary unit). In addition, two solid lines are shown in Figure 48, the thin solid line represents the absorption spectrum. The thick solid line indicates the emission spectrum. Absorption spectrum measured in a chloromethane solution (0.073mmol / L) placed in a quartz cell The absorption spectrum measured by putting only dichloromethane in a quartz cell was subtracted from the result. This shows that.

[0486] As shown in FIG. 48, the organometallic complex [Ir(d2npm) 2 (acac) ] has an emission peak at 645 nm, and red emission is observed from the dichloromethane solution. was measured. EXAMPLES

[0487] <Synthesis Example 7> In this example, an organometallic compound represented by structural formula (115) in Embodiment 1 is used as an embodiment of the present invention. Complexes of the acetylacetonato group, bis[4,6-di(naphthalene-1-yl)pyrimidina] Bis[1-(6-naphthalene-1-yl-4-pyrimidium(III)] 2,4-Pentanedionato-κN3)-2-naphthalenyl-κC 2 O,O ') Iridium (III) (abbreviation: [Ir(d1npm) 2 Synthesis example of (acac)] Here is a specific example: [Ir(d1npm) 2 The structure of (acac)] is shown below: .

[0488] [ka]

[0489] <Step 1; 4,6-di(naphthalen-1-yl)pyrimidine (abbreviation: Hd1npm) Synthesis of > First, 5.00 g of 4,6-dichloropyrimidine, 11.56 g of 1-naphthaleneboronic acid, Sodium carbonate 7.12g, bis(triphenylphosphine)palladium(II) dichloro Lithium (abbreviation: Pd(PPh 3 ) 2 Cl 2 ) 0.29g, water 20mL, acetonitrile 20 1 mL was placed in a recovery flask equipped with a reflux condenser, and the inside of the flask was replaced with argon. The mixture was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. 2.91 g of 1-naphthaleneboronic acid, 1.82 g of sodium carbonate, Pd(PPh 3 ) 2 Cl 2 Put 0.070g, 5mL of water, and 5mL of acetonitrile into the flask and then The solution was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. Water was added, and the organic layer was extracted with dichloromethane. The solution was washed with sodium chloride solution, water, and saturated saline, and then dried over magnesium sulfate. The solution was filtered. The solvent was removed by distillation, and the resulting residue was diluted with hexane:ethyl acetate= The desired pyrimidine derivative was purified by flash column chromatography using a 2:1 eluent. The compound Hd1npm was obtained (yellowish white powder, 41% yield). A microwave synthesis device (CEM Discover) was used. The synthesis of step 1 is as follows. Scheme (i-1) is shown.

[0490] [ka]

[0491] <Step 2: Di-μ-chloro-bis{bis[4,6-di(naphthalen-1-yl)pyridine] {Ir(d1npm)} 2 Cl] 2 Synthesis of Next, 30 mL of 2-ethoxyethanol, 10 mL of water, and Hd1np obtained in step 1 above were added to m2.29g, iridium chloride hydrate (IrCl 3 H 2 O) (Sigma-Aldrich 1.01 g of 1,2-dichloroethane (manufactured by ch.) was placed in a recovery flask equipped with a reflux condenser, and the flask was filled with argon. After that, the mixture was irradiated with microwaves (2.45 GHz, 100 W) for 1 hour to cause a reaction. After the solvent was removed, the residue was filtered and washed with ethanol to obtain the binuclear complex [Ir( d1npm) 2 Cl] 2 The compound was obtained (reddish brown powder, 82% yield). The synthesis sequence of step 2 is as follows: Scheme (i-2) is shown.

[0492] [ka]

[0493] <Step 3; (Acetylacetonato)bis[4,6-di(naphthalen-1-yl)pyridine] [Ir(d1npm) 2 Synthesis of (acac)] > In addition, 30 mL of 2-ethoxyethanol and the binuclear complex [Ir(d1 npm) 2 Cl] 2 1.18g, acetylacetone 0.20g, sodium carbonate 0.70 g was placed in a recovery flask equipped with a reflux condenser, and the atmosphere in the flask was replaced with argon. The material was heated by irradiating it with microwaves (2.45 GHz, 120 W) for 60 minutes. 0.20 g of acetylacetone was placed in the flask and the mixture was again heated in a microwave oven (2.45 GHz 12 The mixture was heated by irradiation with 100 W for 60 minutes. The solvent was removed, and the resulting residue was washed with ethanol. The solid was filtered by suction. The solid was washed with water and ethanol, and then extracted with dichloromethane as a developing solvent. The product was then purified by flash column chromatography using dichloromethane and hexane. The product was recrystallized from a mixed solvent of 1,000g of ethyl acetate to obtain a dark red powder (yield 27%). The synthetic scheme of step 3 (i-3) is shown below.

[0494] [ka]

[0495] Nuclear magnetic resonance spectroscopy ( 1 The results of analysis by 1 H NMR are shown below. Also, 1 The H NMR chart is shown in FIG. 49. From this, it is apparent that in this Synthesis Example 7, The organometallic complex according to one embodiment of the present invention is represented by the structural formula (115) [Ir(d1npm) 2 ( It was found that the compound (acac) was obtained.

[0496] 1 H NMR.δ(CDCl 3 ):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, [Ir(d1npm) 2 UV-visible absorption spectrum of dichloromethane solution of (acac)] The absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and the emission spectrum were measured. The spectrum was measured using an ultraviolet-visible spectrophotometer (V550, manufactured by JASCO Corporation). The chloromethane solution (0.070 mmol / L) was placed in a quartz cell, and measurements were performed at room temperature. The emission spectrum was measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics, Inc.). A degassed dichloromethane solution (0.070 mmol / L) was placed in a quartz cell. The measurement results of the absorption spectrum and emission spectrum are shown in Figure 50. The horizontal axis represents the wavelength (nm), and the vertical axis represents the absorption intensity (arbitrary unit) and emission intensity (arbitrary unit). In addition, two solid lines are shown in Figure 50, and the thin solid line indicates the absorption spectrum. The thick solid line indicates the emission spectrum. Absorption spectrum measured in a chloromethane solution (0.070mmol / L) placed in a quartz cell The absorption spectrum measured by putting only dichloromethane in a quartz cell was subtracted from the result. This shows that.

[0498] As shown in FIG. 50, the organometallic complex [Ir(d1npm) 2 (acac) ] has an emission peak at 608 nm, and orange emission is observed from the dichloromethane solution. was measured. EXAMPLES

[0499] <Synthesis Example 8> In this example, an organogold compound represented by structural formula (119) in Embodiment 1 is used as an embodiment of the present invention. Complex, (acetylacetonato)bis[4,6-di(3-biphenyl)pyrimidinato]i Lithium(III) (also known as bis{3-[6-(1,1'-biphenyl-3-yl)-4 -pyrimidinyl-κN3]-1,1'-biphenyl-4-yl-κC}(2,4-penta ndionate-κ 2 O,O') Iridium(III) (abbreviation: [Ir(d5bpm) 2 ( A specific example of the synthesis of [Ir(d5bpm) 2 (acac )] is shown below.

[0500] [ka]

[0501] <Step 1; Synthesis of 4,6-di(3-biphenyl)pyrimidine (abbreviation: Hd5bpm) > First, 5.03 g of 4,6-dichloropyrimidine, 13.51 g of 3-biphenylboronic acid, Sodium carbonate 7.17g, bis(triphenylphosphine)palladium(II) dichloro Lithium (abbreviation: Pd(PPh3 ) 2 Cl 2 ) 0.29g, water 30mL, acetonitrile 30 1 mL was placed in a recovery flask equipped with a reflux condenser, and the inside of the flask was replaced with argon. The mixture was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. 3.40 g of 3-biphenylboronic acid, 1.77 g of sodium carbonate, Pd(PPh 3 ) 2 Cl 2 Put 0.070g into the flask and turn on the microwave (2.45GHz 100W) again. The solution was heated by irradiation for 60 minutes. Water was then added to the solution, and the organic phase was dissolved in dichloromethane. The resulting organic layer was washed with a saturated aqueous solution of sodium bicarbonate, water, and saturated saline. The solution was filtered and the solvent was removed by distillation. After removing the residue, the resulting residue was diluted with silica gel using toluene:ethyl acetate=40:1 as a developing solvent. The desired pyrimidine derivative Hd5bpm was obtained by purification using column chromatography. Colored powder, 10% yield. Microwave irradiation was performed using a microwave synthesis device (CEM D The synthetic scheme for step 1 (j-1) is shown below.

[0502] [ka]

[0503] Step 2: Di-μ-chloro-bis{bis[4,6-di(3-biphenyl)pyrimidina Iridium (III) (abbreviation: [Ir(d5bpm) 2 Cl] 2 Synthesis of Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the Hd5bpm obtained in step 1 above were added. 1.14g, iridium chloride hydrate (IrCl 3 H 2 O) (Sigma-Aldric (H Company) 0.42 g was placed in a recovery flask equipped with a reflux condenser, and the flask was purged with argon. Then, the mixture was irradiated with microwaves (2.45 GHz, 100 W) for 1 hour to cause a reaction. After the solvent was removed, the residue was filtered and washed with ethanol to give the binuclear complex [Ir(d 5bpm) 2 Cl] 2 The compound was obtained (reddish brown powder, 99% yield). The synthesis scheme for step 2 is as follows: Shows team (j-2).

[0504] [ka]

[0505] <Step 3; (Acetylacetonato)bis[4,6-di(3-biphenyl)pyrimidina Iridium(III) (abbreviation: [Ir(d5bpm) 2 Synthesis of (acac)] Furthermore, 40 mL of 2-ethoxyethanol and the binuclear complex [Ir(d bpm) 2 Cl] 2 1.38g, acetylacetone 0.21g, sodium carbonate 0.74 g was placed in a recovery flask equipped with a reflux condenser, and the atmosphere in the flask was replaced with argon. The material was heated by irradiating it with microwaves (2.45 GHz, 120 W) for 60 minutes. 0.070 g of acetylacetone was placed in the flask and the mixture was again heated in a microwave (2.45 GHz). The mixture was heated by irradiation with a 20W lamp for 60 minutes. The solvent was removed, and the resulting residue was diluted with ethanol. The solid was washed with water and ethanol, and then extracted with dichloromethane as a developing solvent. The product was purified by silica gel column chromatography using dichloromethane and hexane. The solid was recrystallized in a mixed solvent of hexane and dichloromethane to obtain a red-orange solid. The product was purified by silica gel column chromatography using dichloromethane and hexachloroethane as solvents. The product was recrystallized from a mixed solvent of ethyl acetate and ethyl acetate to obtain a reddish orange powder (yield 17%). The synthesis scheme (j-3) of trip 3 is shown below.

[0506] [ka]

[0507] The nuclear magnetic resonance spectroscopy ( 1 The results of analysis by 1 H NMR are shown below. Also, 1 The H NMR chart is shown in FIG. 51. From this, it is apparent that in this Synthesis Example 8, The organometallic complex according to one embodiment of the present invention is represented by the structural formula (119) [Ir(d5bpm) 2 ( It was found that the compound (acac) was obtained.

[0508] 1 H NMR.δ(CDCl 3 ):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, [Ir(d5bpm) 2 UV-visible absorption spectrum of dichloromethane solution of (acac)] The absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and the emission spectrum were measured. The spectrum was measured using an ultraviolet-visible spectrophotometer (V550, manufactured by JASCO Corporation). The chloromethane solution (0.066 mmol / L) was placed in a quartz cell, and measurements were performed at room temperature. The emission spectrum was measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics, Inc.). A degassed dichloromethane solution (0.066 mmol / L) was placed in a quartz cell. The measurement results of the absorption spectrum and emission spectrum are shown in Figure 52. The horizontal axis represents the wavelength (nm), and the vertical axis represents the absorption intensity (arbitrary unit) and emission intensity (arbitrary unit). In addition, two solid lines are shown in Figure 52, the thin solid line represents the absorption spectrum. The thick solid line indicates the emission spectrum. Absorption spectrum measured in a chloromethane solution (0.066mmol / L) placed in a quartz cell The absorption spectrum measured by putting only dichloromethane in a quartz cell was subtracted from the result. This shows that.

[0510] As shown in FIG. 52, the organometallic complex [Ir(d5bpm) 2 (acac) ] has an emission peak at 601 nm, and orange emission is observed from the dichloromethane solution. was measured. EXAMPLES

[0511] <Synthesis Example 9> In this example, an organogold compound represented by structural formula (123) in Embodiment 1 is used as an embodiment of the present invention. Complexes of the acetylacetonato group, bis[4,6-bis(4-methoxyphenyl)pyrimidinium] Nato]iridium(III) (synonym: 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) A specific example of the synthesis of [Ir(modppm) 2 (acac)] structure The structure 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 were 2g, sodium carbonate 7.22g, bis(triphenylphosphine)palladium(II) Dichloride (abbreviation: Pd(PPh 3 ) 2 Cl 2 ) 0.29g, water 20mL, acetonitrile 20 mL of the solution was placed in a recovery flask equipped with a reflux condenser, and the inside of the flask was replaced with argon. The container was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. In addition, 2.58 g of 4-methoxyphenylboronic acid, 1.81 g of sodium carbonate, Pd( PPh 3 ) 2 Cl 2 Put 0.070g, 5mL of water, and 5mL of acetonitrile into a flask. The mixture was heated again by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. Water was then added to this solution, and the organic layer was extracted with dichloromethane. The mixture was washed with an aqueous solution of sodium hydrogen carbonate, water, and saturated saline, and then dried over magnesium sulfate. The dried solution was filtered. The solvent was removed by distillation, and the resulting residue was dissolved in dichloromethane. The mixture was purified by silica gel column chromatography using toluene:ethyl acetate=10:1 as a developing solvent. The desired pyrimidine derivative Hmodppm was obtained (white powder, 62% yield). Microwave irradiation was performed using a microwave synthesis device (Discover, manufactured by CEM). The synthetic scheme for step 1 (k-1) is shown below.

[0514] [ka]

[0515] Step 2: Di-μ-chloro-bis{bis[4,6-bis(4-methoxyphenyl)pi Iridium(III)} (abbreviation: [Ir(modppm) 2 Cl] 2 Synthesis of > Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the Hmodpp obtained in step 1 above were mixed together. m1.97g, iridium chloride hydrate (IrCl 3 H 2 O) (Sigma-Aldrich 1.00 g of 1,2-dichloroethane (manufactured by HORIBA) was placed in a recovery flask equipped with a reflux condenser, and the flask was filled with argon. After that, the mixture was irradiated with microwaves (2.45 GHz, 100 W) for 1 hour to cause a reaction. After the solvent was removed, the residue was filtered and washed with ethanol to obtain the binuclear complex [Ir( modppm 2 Cl] 2 The compound was obtained (gray-green powder, 100% yield). The synthesis scheme (k-2) is shown.

[0516] [ka]

[0517] Step 3: (acetylacetonato)bis[4,6-bis(4-methoxyphenyl)pi Rimidinato]iridium(III) (abbreviation: [Ir(modppm) 2 (acac)] Synthesis> Furthermore, 40 mL of 2-ethoxyethanol and the binuclear complex [Ir(mo dppm) 2 Cl] 2 2.80g, acetylacetone 0.52g, sodium carbonate 1.8 3 g was placed in a recovery flask equipped with a reflux condenser, and the atmosphere in the flask was replaced with argon. The mixture was heated by irradiating it with microwaves (2.45 GHz, 120 W) for 60 minutes. 0.17 g of acetylacetone was placed in the flask and the mixture was heated again in a microwave (2.45 GHz). The mixture was heated by irradiation with a 20W lamp for 60 minutes. The solvent was removed, and the resulting residue was diluted with ethanol. The solid was washed with water and ethanol, and then extracted with a dichloromethane:ethyl acetate mixture. The mixture was purified by silica gel column chromatography using a developing solvent of 25:1. By recrystallization from a mixed solvent of dichloromethane and hexane, a yellow-orange powder was obtained (yield The synthesis scheme for step 3 (k-3) is shown below.

[0518] [ka]

[0519] The nuclear magnetic resonance spectroscopy ( 1 The results of analysis by 1 H NMR are shown below. Also, 1 The H NMR chart is shown in FIG. 53. From this, it is apparent that in this Synthesis Example 9, An organometallic complex according to one embodiment of the present invention, represented by structural formula (123) [Ir(modppm) 2 (acac)] was obtained.

[0520] 1 H NMR.δ(CDCl 3 ):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, select Ir(modppm) 2 UV-visible absorption spectra of dichloromethane solution of (acac)] The absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and the emission spectrum were measured. The spectrum was measured using an ultraviolet-visible spectrophotometer (V550, manufactured by JASCO Corporation). The dichloromethane solution (0.072 mmol / L) was placed in a quartz cell and measurements were performed at room temperature. The emission spectrum was measured using a fluorometer (Hamamatsu Photonics FS920). ) was used, and a degassed dichloromethane solution (0.072 mmol / L) was placed in a quartz cell. The measurements were carried out at room temperature. The results of the absorption and emission spectra are shown in Figure 54. The horizontal axis represents the wavelength (nm), and the vertical axis represents the absorption intensity (arbitrary unit) and emission intensity (arbitrary unit). In addition, two solid lines are shown in Figure 54, and the thin solid line shows the absorption spectrum. The thick solid line indicates the emission spectrum. Absorption spectrum measured in a chloromethane solution (0.072mmol / L) in a quartz cell The absorption spectrum of only dichloromethane in the quartz cell was subtracted from that of the The results are shown.

[0522] As shown in FIG. 54, the organometallic complex [Ir(modppm) 2 (acac )] has an emission peak at 556 nm, and yellow light is emitted from the dichloromethane solution. was observed. EXAMPLES

[0523] <Synthesis Example 10> In this example, an organogold compound represented by structural formula (134) in Embodiment 1 is used as an embodiment of the present invention. Complexes of the acetylacetonato bis(4,5,6-triphenylpyrimidinato)iridium Umium(III) (Bis[2-(5,6-diphenyl-4-pyrimidinyl-κN3] Phenyl-κC](2,4-pentanedionato-κ 2 O,O') Iridium(III) (Abbreviation: [Ir(tppm) 2 A specific example of the synthesis of (acac)] is given below. Ir(tppm) 2 The structure of (acac)] is shown below.

[0524] [ka]

[0525] <Step 1: Synthesis of 4,5,6-triphenylpyrimidine (abbreviation: Htppm)> First, 4.25 g of 5-bromo-4,6-dichloropyrimidine and 6.84 g of phenylboronic acid g, sodium carbonate 5.95 g, bis(triphenylphosphine)palladium(II) di Chloride (abbreviation: Pd(PPh 3 ) 2 Cl 2 ) 0.16g, water 20mL, acetonitrile 20 mL of the reaction mixture was placed in a recovery flask equipped with a reflux condenser, and the inside of the flask was replaced with argon. The vessel was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. In addition, 2.28 g of phenylboronic acid, 1.98 g of sodium carbonate, and Pd(PPh 3 ) 2 C l 2 Put 0.053g, 5mL of water, and 5mL of acetonitrile into the flask and microwave again. (2.45GHz 100W) for 60 minutes. The residue was filtered off with suction and washed with water. The desired pyrimidine derivatives were purified by flash column chromatography using the developing solvent. The compound Htppm was obtained (white powder, 46% yield). The synthesis scheme for step 1 is shown below. l-1).

[0526] [ka]

[0527] <Step 2; Di-μ-chloro-bis[bis(4,5,6-triphenylpyrimidinato) Iridium (III)] (abbreviation: [Ir(tppm) 2 Cl] 2 Synthesis of Next, 30 mL of 2-ethoxyethanol, 10 mL of water, and the Htppm obtained in step 1 above were 2.60g, iridium chloride hydrate (IrCl 3 H 2 O) (Sigma-Aldric (H Company) 1.25 g was placed in a recovery flask equipped with a reflux condenser, and the flask was purged with argon. Then, the mixture was irradiated with microwaves (2.45 GHz, 100 W) for 1 hour to cause a reaction. After the solvent was removed, the residue was filtered and washed with ethanol to give the binuclear complex [Ir(t ppm) 2 Cl] 2 (Brown powder, 75% yield). The synthesis scheme for step 2 is shown below. (l-2) is shown.

[0528] [ka]

[0529] <Step 3; (Acetylacetonato)bis(4,5,6-triphenylpyrimidinato) Iridium(III) (abbreviation: [Ir(tppm) 2 Synthesis of (acac)] Furthermore, 30 mL of 2-ethoxyethanol and the binuclear complex [Ir(tp pm) 2 Cl] 2 1.30g, acetylacetone 0.23g, sodium carbonate 0.82g The mixture was placed in a recovery flask equipped with a reflux condenser, and the atmosphere in the flask was replaced with argon. The sample was heated by irradiating it with microwaves (2.45 GHz, 120 W) for 60 minutes. Add 0.23 g of cetylacetone to the flask and microwave again (2.45 GHz 120 The solvent was removed, and the resulting residue was absorbed in ethanol. The solid was washed with water and ethanol, and then extracted with hexane:ethyl acetate=2:1. The product was purified by flash column chromatography using dichloromethane as the developing solvent. By recrystallization from a mixed solvent of methane and ethanol, a reddish-orange powder was obtained (yield 29. %). The synthetic scheme for step 3 (l-3) is shown below.

[0530] [ka]

[0531] The nuclear magnetic resonance spectroscopy ( 1 The results of analysis by 1 H NMR are shown below. Also, 1 The H NMR chart is shown in FIG. The organometallic complex [Ir(tppm) 2 ( It was found that the compound (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, [Ir(tppm) 2 UV-visible absorption spectrum of dichloromethane solution of (acac)] The absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and the emission spectrum were measured. The spectra were measured using an ultraviolet-visible spectrophotometer (V550, manufactured by JASCO Corporation). The dichloromethane solution (0.074 mmol / L) was placed in a quartz cell and the measurement was carried out at room temperature. A fluorescence spectrometer (FS920, manufactured by Hamamatsu Photonics, Inc.) was used to measure the emission spectrum. The degassed dichloromethane solution (0.074 mmol / L) was placed in a quartz cell and heated at room temperature. The measurement results of the absorption spectrum and emission spectrum are shown in Figure 56. The horizontal axis represents wavelength (nm), and the vertical axis represents absorption intensity (arbitrary units) and emission intensity (arbitrary units). In addition, two solid lines are shown in FIG. 56, the thin solid line indicates the absorption spectrum, The thick solid line indicates the emission spectrum. The absorption spectrum was measured in a quartz cell using a fluoromethane solution (0.074 mmol / L). The absorption spectrum measured by putting only dichloromethane in a quartz cell was subtracted from the result. It shows.

[0534] As shown in FIG. 56, the organometallic complex [Ir(tppm) 2 (acac)] It has an emission peak at 592 nm, and orange emission is observed from the dichloromethane solution. It was done. EXAMPLES

[0535] <Synthesis Example 11> In this example, an organogold compound represented by structural formula (178) in Embodiment 1 is used as an organogold compound according to one embodiment of the present invention. Complexes of the group, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (also known as : Tris[2-(6-methyl-4-pyrimidinyl-κN3)phenyl-κC]iridium (III)) (abbreviation: [Ir(mppm) 3 A specific example of the synthesis of [ Ir(mppm) 3 The structure of ] is shown below.

[0536] [ka]

[0537] First, 1.35 g of the ligand Hmppm obtained in Example 2, tris(acetylacetonato) Put 0.78 g of iridium (III) into a reaction vessel equipped with a three-way cock and The atmosphere was replaced with argon. Then, the reaction was carried out by heating at 250°C for 52 hours. The solvent was removed from the filtrate by distillation, and the residue was then poured onto a silica gel column. The product was purified by column chromatography. The developing solvent was dichloromethane followed by ethyl acetate. The solvent was removed from the obtained fraction, and a yellowish brown solid was obtained (crude yield: 26%). The solid was subjected to flash column chromatography using ethyl acetate:methanol=5:1 as a developing solvent. The fraction was purified by chromatography. The solvent was removed by distillation, and the resulting solid was The product was recrystallized from a mixed solvent of ethanol and hexane to obtain a brown powder (yield 4%). The synthesis scheme (m-1) is shown in FIG.

[0538] [ka]

[0539] Nuclear magnetic resonance spectroscopy ( 1 The results of the analysis by 1 H NMR are shown below. Ta, 1 The H NMR chart is shown in FIG. 57. From this, it is apparent that in this Synthesis Example 11, An organometallic complex according to one embodiment of the present invention, represented by structural formula (178) [Ir(mppm) 3 ]but It was found that it was obtained.

[0540] 1 H NMR.δ(CDCl 3 ):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, [Ir(mppm) 3 The UV-visible absorption spectrum of the dichloromethane solution of The absorption spectrum (simply referred to as the "absorption spectrum") and the emission spectrum were measured. The UV-visible spectrophotometer (V550, manufactured by JASCO Corporation) was used to measure the concentration of the dichloromethane solution. The liquid (0.095 mmol / L) was placed in a quartz cell and measurements were performed at room temperature. The spectra were measured using a fluorometer (Hamamatsu Photonics FS920) in a degassed condition. The dichloromethane solution (0.095 mmol / L) was placed in a quartz cell and measurements were performed at room temperature. The results of the absorption and emission spectra are shown in Figure 58. The horizontal axis is the wavelength. (nm), and the vertical axis represents the absorption intensity (arbitrary unit) and the emission intensity (arbitrary unit). In the figure, two solid lines are shown; the thin solid line shows the absorption spectrum and the thick solid line shows the emission spectrum. The absorption spectrum shown in Figure 58 is a dichloromethane solution. (0.095mmol / L) in a quartz cell and the absorption spectrum was The results shown are those obtained by subtracting the absorption spectrum measured by putting only methane into a quartz cell.

[0542] As shown in FIG. 58, the organometallic complex [Ir(mppm) 3 ] is 548n It has an emission peak at m, and yellow-green emission was observed from the dichloromethane solution. EXAMPLES

[0543] <Synthesis Example 12> In this example, an organogold compound represented by structural formula (194) in Embodiment 1 is used as an organogold compound according to one embodiment of the present invention. Complexes of the group bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmeth Natrium)iridium(III) (synonym: (2,2,6,6-tetramethyl-3,5-hepta ndionate-κ 2O,O')bis{4-methyl-2-[6-(3-methylphenyl)-4 -pyrimidinyl-κN3]phenyl-κC}iridium(III) (abbreviation: [Ir(5 mdppm) 2 A specific example of the synthesis of [Ir(5mdpp(dpm)] is given below. m) 2 The structure of (dpm)] is shown below.

[0544] [ka]

[0545] <Step 1: 4,6-bis(3-methylphenyl)pyrimidine (abbreviation: H5mdppm Synthesis of First, 4.99 g of 4,6-dichloropyrimidine and 9.23 g of 3-methylphenylboronic acid , sodium carbonate 7.18g, bis(triphenylphosphine)palladium(II) dichloride Pd(PPh 3 ) 2 Cl 2 ) 0.29g, water 20mL, acetonitrile 2 100 mL was placed in a recovery flask equipped with a reflux condenser, and the inside of the flask was replaced with argon. The mixture was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. In addition, 2.31 g of 3-methylphenylboronic acid, 1.82 g of sodium carbonate, Pd(PPh 3 ) 2 Cl 2 Put 0.070g, 5mL of water, and 5mL of acetonitrile into the flask and mix again. The specimen was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. Water was added to the solution, and the organic layer was extracted with dichloromethane. The mixture was washed with an aqueous sodium chloride solution, water, and saturated saline, and then dried over magnesium sulfate. The resulting solution was filtered. After evaporating the solvent from this solution, the resulting residue was dissolved in dichloromethane: Purify by silica gel column chromatography using ethyl acetate = 20:1 as a developing solvent, The desired pyrimidine derivative H5mdppm was obtained (light yellow powder, 15% yield). The microwave irradiation was performed using a microwave synthesis device (Discover, manufactured by CEM). The synthetic scheme of step 1 (n-1) is shown below.

[0546] [ka]

[0547] Step 2: Di-μ-chloro-bis{bis[4,6-bis(3-methylphenyl)pyridine {midinato}iridium(III)} (abbreviation: [Ir(5mdppm) 2 Cl] 2 Synthesis of > Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the H5mdpp obtained in step 1 above were added. m1.06g, iridium chloride hydrate (IrCl 3 H 2 O) (Sigma-Aldrich 0.60 g of 1,2-dichloroethane (manufactured by ch.) was placed in a recovery flask equipped with a reflux condenser, and the flask was filled with argon. After that, the mixture was irradiated with microwaves (2.45 GHz, 100 W) for 1 hour to cause a reaction. After the solvent was removed, the residue was filtered and washed with ethanol to obtain the binuclear complex [Ir( 5mdppm) 2 Cl] 2 (Reddish brown powder, 86% yield). The synthesis of step 2 is as follows. Scheme (n-2) is shown.

[0548] [ka]

[0549] <Step 3; Bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloy Iridium(III)(abbreviation: [Ir(5mdppm) 2 (dpm)] > Furthermore, 30 mL of 2-ethoxyethanol and the binuclear complex [Ir(5m dppm) 2 Cl] 2 1.40g, dipivaloylmethane 0.52g, sodium carbonate 1. 100 g was placed in a recovery flask equipped with a reflux condenser, and the atmosphere in the flask was replaced with argon. The mixture was heated by irradiating it with microwaves (2.45 GHz, 120 W) for 60 minutes. Furthermore, 0.17 g of dipivaloylmethane and 10 mL of 2-ethoxyethanol were added to the flask. The mixture was then heated again by irradiating it with microwaves (2.45 GHz, 120 W) for 60 minutes. The solvent was removed by distillation, and the resulting residue was filtered by suction with ethanol. The resulting solid was diluted with water and ethanol. The mixture was washed with ethyl acetate, dissolved in dichloromethane, and filtered through Celite. Recrystallization from a mixed solvent of ethane and ethanol gave a red solid (yield 41%, purity 96%). This solid was purified by silica gel column chromatography using toluene as a developing solvent. The product was recrystallized from a mixture of dichloromethane and ethanol to obtain a vermilion powder (yield: 8%). The synthetic scheme for step 3 (n-3) is shown below.

[0550] [ka]

[0551] Nuclear magnetic resonance spectroscopy of the resulting vermilion powder ( 1 The results of the analysis by 1 H NMR are shown below. Ta,1 The H NMR chart is shown in FIG. 59. From this, it is apparent that in this Synthesis Example 12, An organometallic complex according to one embodiment of the present invention, represented by structural formula (194) [Ir(5mdppm) 2 (dpm)] was obtained.

[0552] 1 H NMR.δ(CDCl 3 ):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, [Ir(5mdppm) 2 UV-visible absorption spectrum of dichloromethane solution of (dpm)] The absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and the emission spectrum were measured. The spectrum was measured using an ultraviolet-visible spectrophotometer (V550, manufactured by JASCO Corporation). The chloromethane solution (0.075 mmol / L) was placed in a quartz cell, and measurements were performed at room temperature. The emission spectrum was measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics, Inc.). A degassed dichloromethane solution (0.075 mmol / L) was placed in a quartz cell. The measurement results of the absorption spectrum and emission spectrum are shown in Figure 60. The horizontal axis represents the wavelength (nm), and the vertical axis represents the absorption intensity (arbitrary unit) and emission intensity (arbitrary unit). In addition, two solid lines are shown in Figure 60, the thin solid line represents the absorption spectrum. The thick solid line indicates the emission spectrum. Absorption spectrum measured in a chloromethane solution (0.075mmol / L) placed in a quartz cell The absorption spectrum measured by putting only dichloromethane in a quartz cell was subtracted from the result. This shows that.

[0554] As shown in FIG. 60, the organometallic complex [Ir(5mdppm) 2 (dpm) ] has an emission peak at 620 nm, and red-orange light is emitted from the dichloromethane solution. was observed. EXAMPLES

[0555] <Synthesis Example 13> In this example, an organogold compound represented by structural formula (195) in Embodiment 1 is used as an organogold compound according to one embodiment of the present invention. Complex, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinium] Dinato]iridium(III) (synonym: (2,6-dimethyl-3,5-heptanedionato) -κ 2 O,O')bis[4-methyl-2-(3-methyl-4-pyrimidinyl-κN3]fu [phenyl-κC]iridium(III) (abbreviation: [Ir(5mdppm) 2 (dibm) A specific example of the synthesis of [Ir(5mdppm) 2 (dibm)] structure The structure is shown below.

[0556] [ka]

[0557] First, 30 mL of 2-ethoxyethanol and the binuclear complex [Ir (5mdppm) 2 Cl] 2 1.27g, diisobutyrylmethane 0.40g, sodium carbonate 0.90 g of sodium was placed in a recovery flask equipped with a reflux condenser, and the atmosphere in the flask was replaced with argon. After that, it was heated by irradiating it with microwaves (2.45 GHz, 120 W) for 60 minutes. Here, 0.13 g of diisobutyrylmethane was added to the flask and microwaved again (2. The mixture was heated by irradiation with a 45 GHz 200 W power source for 60 minutes. The solvent was removed by distillation, and the resulting residue was The residue was filtered with ethanol under suction. The solid obtained was washed with water and ethanol, and The product was purified by flash column chromatography using ethylenediaminetetraacetate as the developing solvent. The product was recrystallized from a mixed solvent of dichloromethane and ethanol to obtain an orange powder (yield: 1 5%). The synthesis scheme (o-1) is shown below.

[0558] [ka]

[0559] The resulting orange powder was analyzed by nuclear magnetic resonance spectroscopy ( 1 The results of the analysis by 1 H NMR are shown below. Ta, 1 The H NMR chart is shown in FIG. 61. From this, it is apparent that in this Synthesis Example 13, An organometallic complex according to one embodiment of the present invention, represented by structural formula (195) [Ir(5mdppm) 2 (dibm)] was found to be obtained.

[0560] 1 H NMR.δ(CDCl 3 ):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, [Ir(5mdppm) 2 UV-visible absorption spectra of dichloromethane solution of (dibm)] The absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and the emission spectrum were measured. The spectrum was measured using an ultraviolet-visible spectrophotometer (V550, manufactured by JASCO Corporation). A dichloromethane solution (0.081 mmol / L) was placed in a quartz cell and measurements were performed at room temperature. The emission spectrum was measured using a fluorometer (Hamamatsu Photonics FS920). ) was used, and a degassed dichloromethane solution (0.081 mmol / L) was placed in a quartz cell. The measurements were carried out at room temperature. The results of the absorption and emission spectra are shown in Figure 62. The horizontal axis represents the wavelength (nm), and the vertical axis represents the absorption intensity (arbitrary unit) and emission intensity (arbitrary unit). In addition, two solid lines are shown in Figure 62, and the thin solid line shows the absorption spectrum. The thick solid line indicates the emission spectrum. Absorption spectrum measured in a chloromethane solution (0.081mmol / L) in a quartz cell The absorption spectrum of only dichloromethane in the quartz cell was subtracted from that of the The results are shown.

[0562] As shown in FIG. 62, the organometallic complex [Ir(5mdppm) 2 (dibm )] has an emission peak at 614 nm and emits red-orange light from a dichloromethane solution. was observed. EXAMPLES

[0563] <Synthesis Example 14> In this example, an organogold compound represented by structural formula (196) in Embodiment 1 is used as an organogold compound according to one embodiment of the present invention. Complexes of the group bis[4,6-di(naphthalene-1-yl)pyrimidinato](dipivaloylmetha Natrium)iridium(III) (synonym: (2,2,6,6-tetramethyl-3,5-hepta ndionate-κ 2 O,O')bis[1-(6-naphthalene-1-yl-4-pyrimidinyl -κN3)-2-naphthalenyl-κC]iridium(III) (abbreviation: [Ir(d1n pm) 2 A specific example of the synthesis of [Ir(dpm)] is given below. 2 ( The structure of dpm) is shown below.

[0564] [ka]

[0565] First, 30 mL of 2-ethoxyethanol and the binuclear complex [Ir( d1npm) 2 Cl] 2 1.20g, dipivaloylmethane 0.37g, sodium carbonate 0 .71g was placed in a recovery flask equipped with a reflux condenser, and the atmosphere in the flask was replaced with argon. After that, the mixture was heated by irradiating it with microwaves (2.45 GHz, 120 W) for 60 minutes. Then, add 0.37 g of dipivaloylmethane to the flask and heat again in a microwave (2.45 GHz). The mixture was heated by irradiation with a 120 W lamp for 60 minutes. The solvent was removed, and the resulting residue was dissolved in ethanol. The solid was washed with water and ethanol, and then extracted with a hexane:ethyl acetate mixture. The mixture was purified by flash column chromatography using a developing solvent of 5:1. The product was recrystallized from a mixture of dichloromethane and ethanol to obtain a dark red powder. (Yield 24%). The synthesis scheme (p-1) is shown below.

[0566] [ka]

[0567] Nuclear magnetic resonance spectroscopy ( 1 The results of analysis by 1 H NMR are shown below. Also, 1 The H NMR chart is shown in Figure 63. From this, it is apparent that in this Synthesis Example 14, The organometallic complex of one embodiment of the present invention represented by the above structural formula (196) [Ir(d1npm) 2 (dpm)] was obtained.

[0568] 1 H NMR.δ(CDCl 3 ):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, [Ir(d1npm) 2 UV-visible absorption spectrum of dichloromethane solution of (dpm)] The absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and the emission spectrum were measured. The spectra were measured using an ultraviolet-visible spectrophotometer (V550, manufactured by JASCO Corporation). The dichloromethane solution (0.064 mmol / L) was placed in a quartz cell and the measurement was carried out at room temperature. A fluorescence spectrometer (FS920, manufactured by Hamamatsu Photonics, Inc.) was used to measure the emission spectrum. The degassed dichloromethane solution (0.064 mmol / L) was placed in a quartz cell and heated at room temperature. The measurement results of the absorption spectrum and emission spectrum are shown in Figure 64. The horizontal axis represents wavelength (nm), and the vertical axis represents absorption intensity (arbitrary units) and emission intensity (arbitrary units). In addition, two solid lines are shown in FIG. 64, the thin solid line indicates the absorption spectrum, The thick solid line indicates the emission spectrum. The absorption spectrum was measured in a quartz cell using a fluoromethane solution (0.064 mmol / L). The absorption spectrum measured by putting only dichloromethane in a quartz cell was subtracted from the result. It shows.

[0570] As shown in FIG. 64, the organometallic complex [Ir(d1npm) 2 (dpm)] It has an emission peak at 613 nm, and red-orange emission is observed from the dichloromethane solution. was measured. EXAMPLES

[0571] <Synthesis Example 15> In this example, an organogold compound represented by structural formula (199) in Embodiment 1 is used as an organogold compound according to one embodiment of the present invention. Complex, (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4- Phenylpyrimidinato]iridium(III) (synonym: bis{2-[5-methyl-6-( 2-Methylphenyl)-4-pyrimidinyl-κN3]phenyl-κC}(2,4-penta ndionate-κ 2 O,O')iridium(III) (abbreviation: [Ir(mpmppm) 2 A specific example of the synthesis of [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, 5.0 g of 4,6-dichloro-5-methylpyrimidine, 2-methylphenylboronic acid 4.6g, cesium carbonate 20g, tricyclohexylphosphine (abbreviation: Cy 3 P)15 % toluene solution 2.5 mL, tris(dibenzylideneacetone)dipalladium(0) (abbreviated Name: Pd 2 (dba) 3 0.47 g of ) and 40 mL of dioxane were added to a flask equipped with a reflux condenser. The inside of the reaction vessel was replaced with argon. The solution was heated by irradiation with a 50 W power source for 2 hours. Water was then added to the solution, and dichloromethane was added. The organic layer was extracted with a saturated aqueous solution of sodium bicarbonate, water, and saturated sodium chloride. The solution was washed with water and dried over magnesium sulfate. The solution after drying was filtered. After removing the solvent, the residue was eluted with dichloromethane on a silica gel column. The resulting fraction was purified by chromatography and concentrated to give 4-chloro-5-methyl The resulting mixture was 6-(2-methylphenyl)pyrimidine (white solid, 58% yield). The microwave irradiation was performed using a microwave synthesis device (Discover, manufactured by CEM). The synthetic scheme of step 1 (q-1) is shown below.

[0574] [ka]

[0575] Step 2: Synthesis of 5-methyl-6-(2-methylphenyl)-4-phenylpyrimidine > Next, 4-chloro-5-methyl-6-(2-methylphenyl) Pyrimidine 1.9g, phenylboronic acid 1.7g, sodium carbonate 1.1g, bis(trimethylsilyl) Phenylphosphine)palladium(II) dichloride (abbreviation: Pd(PPh 3 ) 2 Cl 2 0.105 g of 1,20 mL of water, and 20 mL of acetonitrile were placed in a round-bottom flask equipped with a reflux condenser. The inside of the reaction vessel was replaced with argon. The solution was heated by irradiating with 1 W for 1 hour. Water was then added to the solution, and it was dissolved in dichloromethane. The organic layer was extracted. The obtained organic layer was washed with a saturated aqueous solution of sodium bicarbonate, water, and saturated saline. The solution was washed and dried over magnesium sulfate. The solution after drying was filtered. The solvent of this solution After distilling off the solvent, the residue was eluted with silica gel using hexane:ethyl acetate=9:1 as a developing solvent. The mixture was purified by gel column chromatography, and the obtained fraction was concentrated to give 5-methyl -6-(2-methylphenyl)-4-phenylpyrimidine was obtained (white solid, 87% yield) ) The synthetic scheme for step 2 (q-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) 2 Cl] 2 Synthesis of 30 mL of 2-ethoxyethanol, 10 mL of water, and the 5-methyl-6- (2-Methylphenyl)-4-phenylpyrimidine 2.0 g, iridium chloride hydrate (I rCl 3 H 2 0.955 g of O) (Sigma-Aldrich) was added to a The flask was then filled with argon gas. The mixture was irradiated with a 100W (1.5GHz, 100W) for 1 hour to cause a reaction. After the solvent was removed, the resulting residue was The binuclear complex [Ir(mpmppm) 2 Cl] 2 (Brown Solid, 75% yield). The synthetic 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) 2 Synthesis of (acac)] 20 mL of 2-ethoxyethanol, the binuclear complex [Ir(mpmppm ) 2 Cl] 2 1.8g, acetylacetone 0.360g, sodium carbonate 1.3g, reduced The mixture was placed in a recovery flask equipped with a flow tube, and the atmosphere in the flask was replaced with argon. (2.45GHz 120W) for 1 hour. Water was added to the mixture, and the aqueous layer was extracted with dichloromethane. The organic layer was washed and dried by adding anhydrous magnesium sulfate. The mixture was filtered. The filtrate was concentrated to give a brown solid. After concentration, the mixture was diluted with dichloromethane. Add approximately 500 mL of ethanol and wash the mixture with Florisil (Wako Pure Chemical Industries, Ltd., catalogue no. Filter through a filter aid consisting of laminated layers of alumina and celite. The filtrate was concentrated to give a red solid. By recrystallizing from the mixed solvent, an orange powder was obtained (yield 57%). The synthesis scheme (q-4) is shown below.

[0580] [ka]

[0581] The resulting orange powder was analyzed by nuclear magnetic resonance spectroscopy ( 1 The results of the analysis by 1 H NMR are shown below. Ta, 1 The H NMR chart is shown in FIG. 65. From this, it is apparent that in this Synthesis Example 15, An organometallic complex according to one embodiment of the present invention, represented by structural formula (199) [Ir(mpmppm) 2 (acac)] was obtained.

[0582] 1 H NMR.δ(CDCl 3 ):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, [Ir(mpmppm) 2 UV-visible absorption spectra of dichloromethane solution of (acac)] The absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and the emission spectrum were measured. The spectrum was measured using an ultraviolet-visible spectrophotometer (V550, manufactured by JASCO Corporation). The dichloromethane solution (0.080 mmol / L) was placed in a quartz cell and measurements were performed at room temperature. The emission spectrum was measured using a fluorometer (Hamamatsu Photonics FS920). ) was used, and a degassed dichloromethane solution (0.080 mmol / L) was placed in a quartz cell. The measurements were carried out at room temperature. The results of the absorption and emission spectra are shown in Figure 66. The horizontal axis represents the wavelength (nm), and the vertical axis represents the absorption intensity (arbitrary unit) and emission intensity (arbitrary unit). In addition, two solid lines are shown in Figure 66, and the thin solid line shows the absorption spectrum. The thick solid line indicates the emission spectrum. Absorption spectrum measured in a chloromethane solution (0.080mmol / L) in a quartz cell The absorption spectrum of only dichloromethane in the quartz cell was subtracted from that of the The results are shown.

[0584] As shown in FIG. 66, the organometallic complex [Ir(mpmppm) 2 (acac )] has an emission peak at 564 nm, and yellow light is emitted from the dichloromethane solution. was observed. EXAMPLES

[0585] <Synthesis Example 16> In this example, an organometallic compound represented by structural formula (200) in Embodiment 1, which is one embodiment of the present invention, is used. The complex tris(4-t-butyl-6-phenylpyrimidinato)iridium(III) ( Synonym: Tris[2-(6-tert-butyl-4-pyrimidinyl-κN3)phenyl-κ C]Iridium(III) (abbreviation: [Ir(tBuppm) 3 ]) synthesis example Here is an example. Note that [Ir(tBuppm) 3 The structure of ] is shown below.

[0586] [ka]

[0587] First, 10 g of phenol and the binuclear complex [Ir(tBuppm) 2 Cl] 2 0.97g, HtBuppm obtained in Step 1 of Synthesis Example 4 0.62g, calcium carbonate 1.03 g of sodium was placed in a 100 mL three-neck flask, and the atmosphere in the flask was replaced with argon. The mixture was then heated at 185°C to react. The residue was sonicated in methanol and absorbed. The solid was dissolved in dichloromethane and filtered through a Celite pad. The solution was filtered through a filter aid consisting of a layer of alumina and celite in that order. The solvent was removed by distillation. As a result, a yellow powder was obtained (yield 17%). The synthesis scheme (r-1) is shown below.

[0588] [ka]

[0589] Nuclear magnetic resonance spectroscopy ( 1 The results of the analysis by 1 H NMR are shown below. Ta, 1The H NMR chart is shown in Figure 67. From this, it is apparent that in this Synthesis Example 16, The organometallic complex of one embodiment of the present invention is represented by the structural formula (200) [Ir(tBuppm) 3 ] was obtained.

[0590] 1 H NMR.δ(CDCl 3 ):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, [Ir(tBuppm) 3 The UV-visible absorption spectrum of the dichloromethane solution of The absorption spectrum (hereinafter referred to simply as "absorption spectrum") and the emission spectrum were measured. The measurements were performed using a UV-visible spectrophotometer (V550, manufactured by JASCO Corporation) and dichloromethane. The fluorine solution (0.036 mmol / L) was placed in a quartz cell and measurements were performed at room temperature. The spectrum was measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics, Inc.). The vaporized dichloromethane solution (0.036 mmol / L) was placed in a quartz cell and measured at room temperature. The results of the absorption and emission spectra are shown in Figure 68. The vertical axis represents the wavelength (nm), and the vertical axis represents the absorption intensity (arbitrary unit) and the emission intensity (arbitrary unit). In 68, two solid lines are shown, the thin solid line showing the absorption spectrum and the thick solid line showing the absorption spectrum. The emission spectrum is shown in Fig. 68. The absorption spectrum shown in Fig. 68 was obtained by The absorption spectrum of the solution (0.036 mmol / L) measured in a quartz cell was The absorption spectrum of only chloromethane in a quartz cell was subtracted from the results shown in the figure. do.

[0592] As shown in FIG. 68, the organometallic complex [Ir(tBuppm) 3 ] is 54 It has an emission peak at 0 nm, and yellow-green emission was observed from the dichloromethane solution. . EXAMPLES

[0593] <Synthesis Example 17> In this example, an organometallic compound represented by structural formula (201) in Embodiment 1, which is one embodiment of the present invention, Complexes of bis[4-(2,5-dimethylphenyl)-6-(naphthalene-2-yl)pyridine Midinato](dipivaloylmethanato)iridium(III) (synonym: (2,2,6,6- Tetramethyl-3,5-heptanedionato-κ 2 O,O')bis{3-[6-(2,5- Dimethylphenyl)-4-pyrimidinyl-κN3]-2-naphthalenyl-κC}iridiu (III) (abbreviation: [Ir(dmp2npm) 2 A concrete example of the synthesis of (dpm)] Here is an example. Note that [Ir(dmp2npm) 2 The structure of (dpm)] is shown below.

[0594] [ka]

[0595] <Step 1; Synthesis of 4-chloro-6-(naphthalen-2-yl)pyrimidine> First, 5.0 g of 4,6-dichloropyrimidine, 11.7 g of 2-naphthaleneboronic acid, and carbonic acid Sodium 7.2g, Bis(triphenylphosphine)palladium(II) dichloride ( Abbreviation: Pd(PPh 3 ) 2 Cl 2 0.29 g, 20 mL of water, and 20 mL of acetonitrile The reaction vessel was placed in a recovery flask equipped with a reflux condenser, and the inside of the vessel was replaced with argon. The mixture was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. Naphthaleneboronic acid 2.9g, sodium carbonate 1.8g, Pd(PPh 3 ) 2 Cl 2 0. Add 070g of water, 5mL of water, and 5mL of acetonitrile to the flask and microwave again (2.4 The solution was heated by irradiating it with a 5 GHz 100 W power source for 60 minutes. Water was then added to the solution, and The organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and then with magnesium sulfate. The solution was then filtered. The solvent was removed by distillation, and the resulting residue was The residue was subjected to silica gel column chromatography using hexane:ethyl acetate=5:1 as a developing solvent. The pyrimidine derivative 4-chloro-6-(naphthalene-2-yl)pyrimidine was purified by The compound was obtained (yellowish white powder, yield 48%). The microwave irradiation was performed using a microwave synthesis apparatus (C The synthesis scheme for step 1 (s-1) is shown below. show.

[0596] [ka]

[0597] <Step 2; 4-(2,5-dimethylphenyl)-6-(naphthalen-2-yl)pyridine Synthesis of Mijin (abbreviation: Hdmp2npm)> Next, 3.3 g of 4-chloro-6-naphthalen-2-ylpyrimidine obtained in step 1 above , 2,5-dimethylphenylboronic acid 2.1 g, sodium carbonate 1.5 g, bis(trifluoro Pd(PPh)diphenylphosphinepalladium(II) dichloride 3 )2 Cl 2 ) 0.11g, 20mL of water, and 20mL of acetonitrile were placed in a recovery flask equipped with a reflux condenser. The inside of the reaction vessel was replaced with argon. The mixture was heated by irradiation for 60 minutes. Here, 2,5-dimethylphenylboronic acid 1. 0g, sodium carbonate 0.73g, Pd(PPh 3 ) 2 Cl 2 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 with UV light for 60 minutes. Water was then added to the solution, and the solution was dissolved in dichloromethane. The organic layer was extracted. The obtained organic layer was washed with water and dried over magnesium sulfate. The resulting solution was filtered. The solvent was removed by distillation, and the resulting residue was dissolved in hexane:acetic acid. The pyrimidine derivative was purified by flash column chromatography using ethyl acetate 2:1 as a developing solvent. The diamine derivative Hdmp2npm was obtained (light yellow oil, 97% yield). The synthetic scheme (s-2) is shown below.

[0598] [ka]

[0599] <Step 3: Di-μ-chloro-bis{bis[4-(2,5-dimethylphenyl)-6- (Naphthalen-2-yl)pyrimidinato]iridium(III) p2npm) 2 Cl] 2 Synthesis of Next, 30 mL of 2-ethoxyethanol, 10 mL of water, and Hdmp2 obtained in step 2 above were mixed together. npm4.11g, iridium chloride hydrate (IrCl 3H 2 O) 1.90 g, reflux tube The flask was then filled with argon gas. The mixture was irradiated with a 1.45 GHz 100 W power source for 1 hour to cause a reaction. After removing the solvent, the resulting residue was The residue was filtered and washed with ethanol to obtain the binuclear complex [Ir(dmp2npm) 2 Cl] 2 Get (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 Synthesis of (dpm) Furthermore, 40 mL of 2-ethoxyethanol and the binuclear complex [Ir(dm p2npm) 2 Cl] 2 1.99g, dipivaloylmethane 0.65g, sodium carbonate 1 0.25g was placed in a recovery flask equipped with a reflux condenser, and the atmosphere in the flask was replaced with argon. After that, the mixture was heated by irradiating it with microwaves (2.45 GHz, 120 W) for 60 minutes. Then, add 0.32 g of dipivaloylmethane to the flask and heat again in a microwave (2.45 GHz). The mixture was heated by irradiation with a 120 W lamp for 60 minutes. The solvent was removed, and the resulting residue was dissolved in ethanol. The solid was washed with water and ethanol. Purified by flash column chromatography using ethyl acetate = 5:1 as developing solvent After that, it was recrystallized in a mixed solvent of dichloromethane and hexane to obtain a vermilion powder. The final product was obtained (yield 12%). The synthesis scheme for step 4 (s-4) is shown below.

[0602] [ka]

[0603] Nuclear magnetic resonance spectroscopy of the resulting vermilion powder ( 1 The results of the analysis by 1 H NMR are shown below. Ta, 1 The H NMR chart is shown in Figure 69. From this, it is apparent that in this Synthesis Example 17, The organometallic complex of one embodiment of the present invention is represented by the structural formula (201) [Ir(dmp2npm) 2 (dpm)] was obtained.

[0604] 1 H NMR.δ(CDCl 3 ):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, [Ir(dmp2npm) 2 UV-visible absorption spectra of dichloromethane solution of (dpm) The absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and the emission spectrum were measured. The spectrum was measured using an ultraviolet-visible spectrophotometer (V550, manufactured by JASCO Corporation). The dichloromethane solution (0.067 mmol / L) was placed in a quartz cell and measurements were performed at room temperature. The emission spectrum was measured using a fluorometer (Hamamatsu Photonics FS920). ) was used, and a degassed dichloromethane solution (0.067 mmol / L) was placed in a quartz cell. The measurements were carried out at room temperature. The results of the absorption and emission spectra are shown in Figure 70. The horizontal axis represents the wavelength (nm), and the vertical axis represents the absorption intensity (arbitrary unit) and emission intensity (arbitrary unit). In addition, two solid lines are shown in Figure 70, and the thin solid line shows the absorption spectrum. The thick solid line indicates the emission spectrum. Absorption spectrum measured in a chloromethane solution (0.067mmol / L) in a quartz cell The absorption spectrum of only dichloromethane in the quartz cell was subtracted from that of the The results are shown.

[0606] As shown in FIG. 70, the organometallic complex [Ir(dmp2npm) 2 (dpm )] has an emission peak at 625 nm, and red light is emitted from the dichloromethane solution. was observed. EXAMPLES

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

[0608] [ka]

[0609] A method for fabricating the light emitting device 6 of this example will be described below.

[0610] (Light emitting element 6) First, ITSO was formed as a film on a glass substrate 1100 by sputtering, and the film served as an anode. The first electrode 1101 was formed. The thickness of the electrode was 110 nm, and the area of ​​the electrode was 2 The dimensions were 2 mm x 2 mm.

[0611] As a pretreatment for forming a light-emitting element on the substrate 1100, the substrate surface is washed with water, and then After baking at 00°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0612] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside has been reduced in pressure to about Pa, and vacuum deposition is performed. After vacuum baking at 170° C. for 30 minutes in the heating chamber of the device, the substrate 1100 is It was left to cool for about 0 minutes.

[0613] Next, the surface on which the first electrode 1101 is formed is placed downward. The substrate 1100 thus formed is fixed to a substrate holder provided in a vacuum deposition apparatus, and then 10 -4 P After the pressure was reduced to about a, BPAFLP and molybdenum oxide (VI ) was co-evaporated to form a hole injection layer 1111. The thickness of the layer was set to 40 nm. The weight ratio of PAFLP to molybdenum oxide was 4:2 (=BPAFLP:molybdenum oxide). The concentration was adjusted to be 1.

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

[0615] Furthermore, 2mDBTPDBq-II, PCBA1BP, and the bis( 4,6-Diphenylpyrimidinato)(dipivaloylmethanato)iridium(III)(abbreviation Name: [Ir(dppm) 2 (dpm)]) was co-evaporated onto the hole transport layer 1112 to form the light emitting layer 1 113 was formed. Here, 2mDBTPDBq-II, PCBA1BP and [Ir(d ppm) 2 (dpm)] weight ratio is 0.8:0.2:0.025 (=2mDBTPDB q-II: PCBA1BP: [Ir(dppm) 2 (dpm)]) The thickness of the light-emitting layer 1113 was 40 nm.

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

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

[0618] Furthermore, LiF was evaporated onto the second electron transport layer 1114b to a thickness of 1 nm to form an electron injection layer. 1115 was formed.

[0619] Finally, a 200 nm film of aluminum was deposited on the second electrode 1103, which served as the cathode. The light-emitting element 6 of this example was fabricated by vapor deposition so as to have a thickness.

[0620] In the above-mentioned deposition process, the deposition was all performed by a resistance heating method.

[0621] The element structure of the thus obtained Light-emitting Element 6 is shown in Table 11.

[0622] [Table 11]

[0623] The light emitting element 6 is placed in a glove box with a nitrogen atmosphere so that the light emitting element 6 is not exposed to the air. After the sealing work was performed so as to prevent the light-emitting element 6 from being damaged, the operating characteristics of the light-emitting element 6 were measured. The measurements were carried out at room temperature (atmosphere maintained at 25°C).

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

[0625] [Table 12]

[0626] FIG. 74 shows the emission spectrum when a current of 0.1 mA is applied to the light-emitting element 6. In FIG. 74, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). As shown in Table 12, the emission spectrum of the light-emitting element 6 had a peak at 586 nm. As shown in the figure, 1100cd / m 2 The CIE chromaticity coordinates of light-emitting element 6 at the luminance of (x,y) are =(0.55, 0.45). From this result, it can be seen that the light-emitting element 6 has an emission efficiency of [Ir(dppm) 2 It was found that orange luminescence originating from the dichloromethane (dpm) was obtained.

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

[0628] The above results show that high light emission can be achieved by using the organometallic complex of one embodiment of the present invention as a light-emitting material. It has been shown that it is possible to realize highly optically efficient devices.

[0629] Next, a reliability test was conducted on the light-emitting element 6. The results of the reliability test are shown in FIG. The vertical axis shows the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis shows the driving time of the element. Indicates time (h).

[0630] Reliability test: initial brightness of 5000cd / m 2 The light emitting element is set at a constant current density. Driven 6.

[0631] After 140 hours, the luminance of the light-emitting element 6 remained at 85% of the initial luminance.

[0632] From the above results, it is possible to improve reliability by using the organometallic complex of one embodiment of the present invention as a light-emitting material. It was shown that it is possible to realize devices with high performance. EXAMPLES

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

[0634] [ka]

[0635] A method for fabricating the light emitting device 7 of this example will be described below.

[0636] (Light emitting element 7) First, ITSO was formed as a film on a glass substrate 1100 by sputtering, and the film served as an anode. The first electrode 1101 was formed. The thickness of the electrode was 110 nm, and the area of ​​the electrode was 2 The dimensions were 2 mm x 2 mm.

[0637] As a pretreatment for forming a light-emitting element on the substrate 1100, the substrate surface is washed with water, and then After baking at 00°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0638] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside has been reduced in pressure to about Pa, and vacuum deposition is performed. After vacuum baking at 170° C. for 30 minutes in the heating chamber of the device, the substrate 1100 is It was left to cool for about 0 minutes.

[0639] Next, the surface on which the first electrode 1101 is formed is placed downward. The substrate 1100 thus formed is fixed to a substrate holder provided in a vacuum deposition apparatus, and then 10 -4 P After reducing the pressure to about a, 1,3,5-tri(dibenzothiophene) was placed on the first electrode 1101. DBT3P-II) and molybdenum(VI) oxide were co-evaporated. The hole injection layer 1111 was formed by deposition of DBT3P The weight ratio of DBT3P-II to molybdenum oxide was 4:2 (=DBT3P-II:molybdenum oxide). The concentration was adjusted to be 1.

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

[0641] In addition, 2mDBTPDBq-II, 4,4'-bis[N-(1-naphthyl)-N-phenyl [Nylamino]biphenyl (abbreviation: NPB) and (acetylacetonylamino)biphenyl synthesized in Example 13 Nato)bis[4,6-di(naphthalene-2-yl)pyrimidinato]iridium(III) (Abbreviation: [Ir(d2npm) 2 (acac)]) was co-evaporated onto the hole transport layer 1112. The light-emitting layer 1113 was formed. Here, 2mDBTPDBq-II, NPB and [Ir(d 2npm) 2 The weight ratio of (acac) was 0.8:0.2:0.025 (=2mDBTP DBq-II:NPB:[Ir(d2npm) 2 (acac)]) The thickness of the light-emitting layer 1113 was 40 nm.

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

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

[0644] Furthermore, LiF was evaporated onto the second electron transport layer 1114b to a thickness of 1 nm to form an electron injection layer. 1115 was formed.

[0645] Finally, a 200 nm film of aluminum was deposited on the second electrode 1103, which served as the cathode. The light-emitting element 7 of this example was fabricated by depositing the material so as to have a thickness.

[0646] In the above-mentioned deposition process, the deposition was all performed by a resistance heating method.

[0647] The element structure of the thus obtained light-emitting element 7 is shown in Table 13.

[0648] [Table 13]

[0649] The light emitting element 7 is placed in a glove box with a nitrogen atmosphere so that the light emitting element 7 is not exposed to the air. After the sealing work was performed so as not to cause any damage to the light-emitting element 7, the operating characteristics of the light-emitting element 7 were measured. The measurements were carried out at room temperature (atmosphere maintained at 25°C).

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

[0651] [Table 14]

[0652] FIG. 79 shows the emission spectrum when a current of 0.1 mA is applied to the light-emitting element 7. In FIG. 79, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). As shown in Table 14, the emission spectrum of the light-emitting element 7 had a peak at 616 nm. As shown in the figure, 1000cd / m2 The CIE chromaticity coordinates of the light-emitting element 7 at the luminance of (x, y) are =(0.64, 0.36). From this result, it can be seen that the light-emitting element 7 has an ) 2 It was found that red luminescence originating from (acac)] was obtained.

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

[0654] The above results show that high light emission can be achieved by using the organometallic complex of one embodiment of the present invention as a light-emitting material. It has been shown that it is possible to realize highly optically efficient devices.

[0655] Next, a reliability test was conducted on the light-emitting element 7. The results of the reliability test are shown in FIG. The vertical axis shows the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis shows the driving time of the element. Indicates time (h).

[0656] Reliability test: initial brightness of 5000cd / m 2 The light emitting element is set at a constant current density. Driven 7.

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

[0658] From the above results, it is possible to improve reliability by using the organometallic complex of one embodiment of the present invention as a light-emitting material. It was shown that it is possible to realize a device with high performance. EXAMPLES

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

[0660] [ka]

[0661] A method for fabricating the light emitting device 8 of this example will be described below.

[0662] (Light emitting element 8) The light-emitting device 8 was fabricated in the same manner as the light-emitting device 7 shown in Example 26, except for the light-emitting layer 1113 . The light-emitting layer 1113 of the light-emitting element 8 will be described below.

[0663] The light-emitting layer 1113 of the light-emitting element 8 was made of 2mDBTPDBq-II, NPB, and the compound of Example 17. (Acetylacetonato)bis(4,5,6-triphenylpyrimidinato)iridium Ir(tppm) 2 (acac)]) was co-evaporated. Here, 2mDBTPDBq-II, NPB and [Ir(tppm) 2 (acac) The weight ratio of ] was 0.8:0.2:0.025 (=2mDBTPDBq-II:NPB:[ Ir(tppm) 2 (acac)]). The thickness was set to 40 nm.

[0664] The element structure of the obtained light-emitting element 8 is shown in Table 15.

[0665] [Table 15]

[0666] The light emitting element 8 is placed in a glove box with a nitrogen atmosphere so that the light emitting element 8 is not exposed to the air. After the sealing work was performed so as to prevent the light-emitting element 8 from being damaged, the operating characteristics of the light-emitting element 8 were measured. The measurements were carried out at room temperature (atmosphere maintained at 25°C).

[0667] The current density-luminance characteristics of the light-emitting element 8 are shown in FIG. 81. In FIG. 81, the horizontal axis indicates the current density (m A / cm 2 ) and the vertical axis is luminance (cd / m 2 The voltage-luminance characteristics are shown in Figure 82. In Figure 82, the horizontal axis represents voltage (V) and the vertical axis represents luminance (cd / m 2 ) and also represents brightness. The luminance-current efficiency characteristics are shown in Figure 83. In Figure 83, the horizontal axis is the luminance (cd / m 2 ) on the vertical axis represents the current efficiency (cd / A). The luminance vs. external quantum efficiency characteristics are shown in Figure 85. In this figure, the horizontal axis is luminance (cd / m 2 ) and the vertical axis indicates external quantum efficiency (%).

[0668] The luminance of the light-emitting element 8 is 850 cd / m 2 Voltage (V) and current density (mA / cm 2 ), 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] FIG. 84 shows the emission spectrum when a current of 0.1 mA is applied to the light-emitting element 8. In FIG. 84, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). As shown in Table 16, the emission spectrum of the light-emitting element 8 had a peak at 593 nm. As shown in the figure, 850cd / m 2 The CIE chromaticity coordinates of light-emitting element 8 at a luminance of (x,y) = (0.59, 0.41). From this result, it can be seen that the light-emitting element 8 has an emission efficiency of [Ir(tppm) 2 It was found that orange luminescence originating from the cation exchange reaction (cation (acac)) was obtained.

[0671] As can be seen from FIGS. 81 to 83 and 85 and Table 16, the light-emitting element 8 has a luminous efficiency of In particular, the light-emitting element 8 had an luminance of 850 cd / m 2 The external quantum efficiency at a brightness of 3 The light extraction efficiency of organic EL elements is 20% to 30%. 0%, so the absorption of the upper and lower electrodes must be taken into consideration (the above light extraction efficiency is approximately If we assume that the efficiency decreases by 10%, the limit of external quantum efficiency should be around 25% at most. However, the results of this study exceed those results, proving that the conventional theoretical value of light extraction efficiency is incorrect. In other words, this suggests that the theoretical value of the light extraction efficiency is incorrect. By using the organometallic complex of one embodiment of the present invention, a highly efficient light-emitting element not previously available can be realized. It can be achieved.

[0672] The above results show that high light emission can be achieved by using the organometallic complex of one embodiment of the present invention as a light-emitting material. It has been shown that it is possible to realize highly optically efficient devices.

[0673] Next, a reliability test was conducted on the light-emitting element 8. The results of the reliability test are shown in FIG. The vertical axis shows the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis shows the driving time of the element. Indicates time (h).

[0674] Reliability test: initial brightness of 5000cd / m 2 The light emitting element is set at a constant current density. Driven 8.

[0675] After 340 hours, the luminance of the light-emitting element 8 remained at 81% of the initial luminance.

[0676] From the above results, it is possible to improve reliability by using the organometallic complex of one embodiment of the present invention as a light-emitting material. It was shown that it is possible to realize a device with high performance. EXAMPLES

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

[0678] [ka]

[0679] A method for fabricating the light emitting device 9 of this example will be described below.

[0680] (Light emitting element 9) Light-emitting device 9 was fabricated in the same manner as light-emitting device 7 shown in Example 26, except for the light-emitting layer 1113 . The light-emitting layer 1113 of the light-emitting element 9 will be described below.

[0681] The light-emitting layer 1113 of the light-emitting element 9 is made of 2mDBTPDBq-II, PCBA1BP, and Example 18 (Tris(4-methyl-6-phenylpyrimidinato)iridium(III) )(Abbreviation: [Ir(mppm) 3 ]) was co-evaporated. PDBq-II, PCBA1BP and [Ir(mppm) 3 ] by weight ratio is 0.8:0. 2:0.05(=2mDBTPDBq-II:PCBA1BP:[Ir(mppm) 3 ] ) The thickness of the light-emitting layer 1113 was adjusted to 40 nm.

[0682] The element structure of the obtained light-emitting element 9 is shown in Table 17.

[0683] [Table 17]

[0684] The light emitting element 9 is placed in a glove box with a nitrogen atmosphere so that the light emitting element 9 is not exposed to the air. After the sealing work was performed so as to prevent the light-emitting element 9 from being damaged, the operating characteristics of the light-emitting element 9 were measured. The measurements were carried out at room temperature (atmosphere maintained at 25°C).

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

[0686] [Table 18]

[0687] FIG. 90 shows the emission spectrum when a current of 0.1 mA is applied to the light emitting element 9. In FIG. 90, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). As shown in Table 18, the emission spectrum of the light-emitting element 9 had a peak at 536 nm. As shown in the figure, 770cd / m 2 The CIE chromaticity coordinates of the light-emitting element 9 at a luminance of (x,y) = (0.41, 0.58). From this result, it can be seen that the light-emitting element 9 has an 3 It was found that yellow-green luminescence originating from the .

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

[0689] The above results show that high light emission can be achieved by using the organometallic complex of one embodiment of the present invention as a light-emitting material. It has been shown that it is possible to realize highly optically efficient devices.

[0690] Next, a reliability test was conducted on the light-emitting element 9. The results of the reliability test are shown in FIG. The vertical axis shows the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis shows the driving time of the element. Indicates time (h).

[0691] Reliability test: initial brightness of 5000cd / m 2 The light emitting element is set at a constant current density. Driven 9.

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

[0693] From the above results, it is possible to improve reliability by using the organometallic complex of one embodiment of the present invention as a light-emitting material. It was shown that it is possible to realize a device with high performance. EXAMPLES

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

[0695] [ka]

[0696] A method for fabricating the light emitting device 10 of this embodiment will be described below.

[0697] (Light emitting element 10) The light-emitting device 10 was fabricated in the same manner as the light-emitting device 7 shown in Example 26, except for the light-emitting layer 1113. The light-emitting layer 1113 of the light-emitting element 10 will be described below.

[0698] The light-emitting layer 1113 of the light-emitting element 10 was made of 2mDBTPDBq-II, NPB, and the compound of Example 19. The synthesized bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmetha Nat)iridium(III) (abbreviation: [Ir(5mdppm) 2 (dpm)]) was co-evaporated. Here, 2mDBTPDBq-II, NPB and [Ir(5mdp pm) 2 (dpm)] weight ratio is 0.8:0.2:0.05 (=2mDBTPDBq- II: NPB: [Ir (5mdppm) 2 (dpm)]). The thickness of the light-emitting layer 1113 was 40 nm.

[0699] The element structure of the obtained light-emitting element 10 is shown in Table 19.

[0700] [Table 19]

[0701] The light emitting element 10 is placed in a glove box with a nitrogen atmosphere so that the light emitting element 10 is exposed to the atmosphere. After sealing to prevent leakage, the operating characteristics of the light emitting element 10 were measured. The measurements were carried out at room temperature (atmosphere maintained at 25°C).

[0702] FIG. 92 shows the current density-luminance characteristics of the light-emitting element 10. In FIG. 92, the horizontal axis indicates the current density ( mA / cm 2 ) and the vertical axis is luminance (cd / m 2 ) and the voltage-luminance characteristics are shown in Figure 93. In FIG. 93, the horizontal axis represents voltage (V) and the vertical axis represents luminance (cd / m 2 ) Also, The luminance-current efficiency characteristics are shown in Figure 94. In Figure 94, the horizontal axis is luminance (cd / m 2 ) vertically The axis represents the current efficiency (cd / A). The luminance-external quantum efficiency characteristics are shown in Figure 96. 6, the horizontal axis is luminance (cd / m 2 ) and the vertical axis indicates external quantum efficiency (%).

[0703] The luminance of the light-emitting element 10 is 1000 cd / m 2 Voltage (V) and current density (m A / cm 2 ), CIE chromaticity coordinates (x, y), current efficiency (cd / A), power efficiency (lm / The optical density (W) and external quantum efficiency (%) are shown in Table 20.

[0704] [Table 20]

[0705] FIG. 95 shows an emission spectrum when a current of 0.1 mA is applied to the light emitting element 10. In FIG. 95, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). As shown in the figure, the emission spectrum of the light-emitting element 10 had a peak at 606 nm. 20, 1000cd / m 2 The CIE chromaticity coordinates of light-emitting element 10 at a luminance of (x , y)=(0.62, 0.38). From this result, the light-emitting element 10 has an mdppm) 2 It was found that orange luminescence originating from the dichloromethane (dpm) was obtained.

[0706] As can be seen from FIGS. 92 to 94 and 96 and Table 20, the light emitting element 10 has a luminous efficiency of In particular, the light-emitting element 10 had a luminance of 1000 cd / m 2 External quantum efficiency at a luminance of However, the light extraction efficiency of the organic EL element was 20%. Since it is said that the light extraction efficiency is about 100% to 300%, the absorption of the upper and lower electrodes must be taken into consideration (see above). If we assume that the external quantum efficiency is reduced by about 10%, the limit of the external quantum efficiency should be about 25% at most. However, the results of this study exceed this, and the conventional theoretical value of light extraction efficiency is This suggests that the theoretical value of the light extraction efficiency is incorrect. By using the organometallic complex according to one embodiment of the present invention, it is possible to achieve highly efficient light emission that is not possible with conventional methods. The device can be realized.

[0707] The above results show that high light emission can be achieved by using the organometallic complex of one embodiment of the present invention as a light-emitting material. It has been shown that it is possible to realize highly optically efficient devices.

[0708] Next, a reliability test was performed on the light-emitting element 10. The results of the reliability test are shown in FIG. In the graph, the vertical axis indicates the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis indicates the driving time of the element. The operating time (h) is shown.

[0709] Reliability test: initial brightness of 5000cd / m 2 The light emitting element is set at a constant current density. Driven 10.

[0710] After 180 hours, the luminance of the light-emitting element 10 remained at 83% of the initial luminance.

[0711] From the above results, it is possible to improve reliability by using the organometallic complex of one embodiment of the present invention as a light-emitting material. It was shown that it is possible to realize a device with high performance. EXAMPLES

[0712] In this example, a light-emitting element of one embodiment of the present invention will be described with reference to FIG. The chemical formulas of the materials used are shown below. Materials already shown will be omitted.

[0713] [ka]

[0714] A method for fabricating the light emitting device 11 of this example will be described below.

[0715] (Light emitting element 11) The light-emitting device 11 was fabricated in the same manner as the light-emitting device 7 shown in Example 26, except for the light-emitting layer 1113. The light-emitting layer 1113 of the light-emitting element 11 will be described below.

[0716] The light-emitting layer 113 of the light-emitting element 11 was made of 2mDBTPDBq-II, NPB, and the compound of Example 20. The synthesized (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidine dinato]iridium(III) (abbreviation: [Ir(5mdppm) 2 (dibm)]) The film was formed by vapor deposition of 2mDBTPDBq-II, NPB, and [Ir(5m dppm) 2 (dibm)] weight ratio is 0.8:0.2:0.05 (=2mDBTPD Bq-II:NPB:[Ir(5mdppm) 2 (dibm)]) The thickness of the light-emitting layer 1113 was 40 nm.

[0717] The element structure of the obtained light-emitting element 11 is shown in Table 21.

[0718] [Table 21]

[0719] The light emitting element 11 is placed in a glove box with a nitrogen atmosphere so that the light emitting element 11 is exposed to the atmosphere. After sealing to prevent leakage, the operating characteristics of the light emitting element 11 were measured. The measurements were carried out at room temperature (atmosphere maintained at 25°C).

[0720] FIG. 98 shows the current density-luminance characteristics of the light-emitting element 11. In FIG. 98, the horizontal axis indicates the current density ( mA / cm 2 ) and the vertical axis is luminance (cd / m 2 ) and the voltage-luminance characteristics are shown in Figure 99. In Figure 99, the horizontal axis represents voltage (V) and the vertical axis represents luminance (cd / m 2 ) Also, The luminance-current efficiency characteristics are shown in FIG. 100. In FIG. 100, the horizontal axis is luminance (cd / m 2 )of The vertical axis represents the current efficiency (cd / A). The luminance vs. external quantum efficiency characteristics are shown in Figure 102. In Figure 102, the horizontal axis is luminance (cd / m 2 ) and the vertical axis indicates the external quantum efficiency (%). .

[0721] The luminance of the light-emitting element 11 is 930 cd / m 2 Voltage (V) and current density (mA / cm 2 ), CIE chromaticity coordinates (x, y), current efficiency (cd / A), power efficiency (lm / W ) and external quantum efficiency (%) are shown in Table 22.

[0722] [Table 22]

[0723] FIG. 101 shows the emission spectrum when a current of 0.1 mA is applied to the light emitting element 11. In FIG. 101, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). As shown in FIG. 1, the emission spectrum of the light-emitting element 11 had a peak at 607 nm. As shown in Table 22, 930 cd / m 2 The CIE chromaticity coordinates of light-emitting element 11 at a luminance of (x, y)=(0.61, 0.38). From this result, the light-emitting element 11 has an [Ir (5mdppm) 2 (dibm)] was observed.

[0724] As can be seen from FIGS. 98 to 100 and 102 and Table 22, the light-emitting element 11 emits light. The efficiency was particularly good. Light-emitting element 11 had an efficiency of 930 cd / m 2 External quantum efficiency at a luminance of The light extraction efficiency of the organic EL element was 2 It is said that the efficiency is about 0% to 30%, so the absorption of the upper and lower electrodes must be taken into consideration (see above for the light extraction efficiency). If we assume that the efficiency will decrease by about 10%, the limit of the external quantum efficiency should be around 25%. However, the results of this study exceed this, and are closer to the theoretical value of the conventional light extraction efficiency. This suggests that the theoretical value of the light extraction efficiency is incorrect. It can be suggested that the use of an organometallic complex according to one embodiment of the present invention can achieve highly efficient generation of light that has not been achieved before. Optical elements can be realized.

[0725] The above results show that high light emission can be achieved by using the organometallic complex of one embodiment of the present invention as a light-emitting material. It has been shown that it is possible to realize highly optically efficient devices.

[0726] Next, a reliability test was performed on the light-emitting element 11. The results of the reliability test are shown in FIG. In Figure 3, the vertical axis shows the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis shows the Indicates the operating time (h).

[0727] Reliability test: initial brightness of 5000cd / m 2 The light emitting element is set at a constant current density. Driven 11.

[0728] After 330 hours, the luminance of the light-emitting element 11 remained at 80% of the initial luminance.

[0729] From the above results, it is possible to improve reliability by using the organometallic complex of one embodiment of the present invention as a light-emitting material. It was shown that it is possible to realize a device with high performance. EXAMPLES

[0730] In this example, a light-emitting element of one embodiment of the present invention will be described with reference to FIG. The chemical formulas of the materials used are shown below. Materials already shown will be omitted.

[0731] [ka]

[0732] A method for fabricating the light emitting device 12 of this example will be described below.

[0733] (Light emitting element 12) The light-emitting device 12 was fabricated in the same manner as the light-emitting device 7 shown in Example 26, except for the light-emitting layer 1113. The light-emitting layer 1113 of the light-emitting element 12 will be described below.

[0734] The light-emitting layer 1113 of the light-emitting element 12 is made of 2mDBTPDBq-II, PCBA1BP, and Bis[4,6-di(naphthalene-1-yl)pyrimidinato](dipivalo) synthesized in Example 21 Iridium(III) (abbreviation: [Ir(d1npm) 2 (dpm)]) The film was formed by co-evaporation of 2mDBTPDBq-II, PCBA1BP, and [ Ir(d1npm) 2 (dpm)] weight ratio is 0.8:0.2:0.05 (=2mDB TPDBq-II:PCBA1BP:[Ir(d1npm) 2 (dpm)] The thickness of the light-emitting layer 1113 was adjusted to 40 nm.

[0735] The element structure of the obtained light-emitting element 12 is shown in Table 23.

[0736] [Table 23]

[0737] The light emitting element 12 is placed in a glove box with a nitrogen atmosphere so that the light emitting element 12 is exposed to the atmosphere. After sealing to prevent leakage, the operating characteristics of the light emitting element 12 were measured. The measurements were carried out at room temperature (atmosphere maintained at 25°C).

[0738] FIG. 104 shows the current density-luminance characteristics of the light-emitting element 12. In FIG. 104, the horizontal axis indicates the current density. degree(mA / cm 2 ) and the vertical axis is luminance (cd / m 2 ) and the voltage-luminance characteristics are shown in Fig. 1. In Fig. 105, the horizontal axis represents voltage (V) and the vertical axis represents luminance (cd / m 2 ) The luminance-current efficiency characteristics are shown in FIG. 106. In FIG. 106, the horizontal axis is luminance (cd / m 2 ) and the vertical axis represents current efficiency (cd / A). 0 cd / m 2 Voltage (V) and current density (mA / cm 2 ), CIE chromaticity coordinates (x, y ), current efficiency (cd / A), power efficiency (lm / W), and external quantum efficiency (%) are shown in Table 24. vinegar.

[0739] [Table 24]

[0740] FIG. 107 shows an emission spectrum when a current of 0.1 mA is applied to the light emitting element 12. In FIG. 107, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). As shown in FIG. 7, the emission spectrum of the light-emitting element 12 had a peak at 607 nm. As shown in Table 24, 1200 cd / m 2 CIE chromaticity coordinates of light-emitting element 12 at luminance of was (x, y)=(0.63, 0.37). From this result, the light-emitting element 12 had an [I r(d1npm) 2 It was found that red luminescence originating from the fluorine-containing compound (dpm) was obtained.

[0741] As can be seen from Table 24 and FIGS. 104 to 106, the light-emitting element 12 has good luminous efficiency. I did.

[0742] The above results show that high light emission can be achieved by using the organometallic complex of one embodiment of the present invention as a light-emitting material. It has been shown that it is possible to realize highly optically efficient devices.

[0743] Next, a reliability test was performed on the light-emitting element 12. The results of the reliability test are shown in FIG. In FIG. 8, the vertical axis shows the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis shows the Indicates the operating time (h).

[0744] Reliability test: initial brightness of 5000cd / m 2 The light emitting element is set at a constant current density. Driven 12.

[0745] After 170 hours, the luminance of the light-emitting element 12 remained at 57% of the initial luminance.

[0746] From the above results, it is possible to improve reliability by using the organometallic complex of one embodiment of the present invention as a light-emitting material. It was shown that it is possible to realize a device with high performance. EXAMPLES

[0747] In this example, a light-emitting element of one embodiment of the present invention will be described with reference to FIG. The chemical formulas of the materials used are shown below. Materials already shown will be omitted.

[0748] [ka]

[0749] A method for fabricating the light emitting device 13 of this example will be described below.

[0750] (Light emitting element 13) The light-emitting device 13 was fabricated in the same manner as the light-emitting device 7 shown in Example 26, except for the light-emitting layer 1113. The light-emitting layer 1113 of the light-emitting element 13 will be described below.

[0751] The light-emitting layer 1113 of the light-emitting element 13 is made of 2mDBTPDBq-II, PCBA1BP, and The (ac...

Claims

[Claim 1] An organometallic complex having a structure represented by general formula (G1): 【Chemistry 1】 (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 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; Ar １ represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.

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