Light-emitting element, light-emitting device, lighting device, and electronic apparatus

Abstract

To provide an organometallic complex with high light emission efficiency which achieves improved color purity by reducing half width of a light emission spectrum, as a new substance having a new skeleton.SOLUTION: An organometallic complex includes, as a ligand, a six-membered ring of a heterocyclic aromatic ring including two or more nitrogen, including a coordinating nitrogen atom, and a β-diketone (in a general formula, X represents a substituted or unsubstituted six-membered heteroaromatic ring including two or more nitrogen atoms, including the coordinating nitrogen atom, and each of R1 to R4 represents a 1-6C alkyl group).SELECTED DRAWING: None

Description

[Technical field]

[0001] One aspect of the present invention relates to an organometallic complex that can convert a triplet excited state into luminescence. The present invention relates to an organometallic complex. The present invention also relates to a light-emitting element, a light-emitting device, an electronic device, and and lighting devices. [Background technology]

[0002] Organic compounds become excited by absorbing light. This can cause various reactions (photochemical reactions) or luminescence. There are various cases and applications.

[0003] An example of a photochemical reaction is the reaction of singlet oxygen with an unsaturated organic molecule (oxygen addition). Since the ground state of oxygen molecules is a triplet state, singlet oxygen (singlet oxygen) is a direct It is not produced by photoexcitation. However, in the presence of other triplet excited molecules, singlet acids This produces a compound capable of forming triplet excited molecules, which can then undergo an oxygen addition reaction. The compounds are called photosensitizers.

[0004] Thus, to generate singlet oxygen, triplet excited molecules must be formed by photoexcitation. However, the ground state of most organic compounds is a singlet state. Therefore, photoexcitation to the triplet excited state is a forbidden transition, and triplet excited molecules are unlikely to be generated. Therefore, such photosensitizers are required to induce intersystem crossover from the singlet excited state to the triplet excited state. Compounds that are prone to photoexcitation (or forbidden transitions such as direct photoexcitation to triplet excited states) In other words, such compounds are required to act as photosensitizers. It can be said that it is possible to use it in various ways and is beneficial.

[0005] Such compounds often also emit phosphorescence. This is the emission caused by the transition between two energies. In normal organic compounds, the triplet This refers to the emission that occurs when an electron returns from an excited state to the singlet ground state (as opposed to the singlet excited The emission of light when the electron goes from the excited state to the singlet ground state is called fluorescence. Compounds capable of converting the triplet excited state into light emission (hereinafter referred to as phosphorescent compounds) An example of an application field is a light-emitting element that uses an organic compound as a light-emitting substance.

[0006] The structure of this light-emitting element is simply a light-emitting layer containing an organic compound, which is a light-emitting substance, provided between electrodes. Its simple structure and characteristics such as thin, lightweight, high-speed response, and low DC voltage operation make it the next-generation It is attracting attention as a flat panel display element. The display also features excellent contrast and image quality, as well as a wide viewing angle.

[0007] The light-emitting mechanism of a light-emitting element that uses an organic compound as a light-emitting substance is a carrier injection type. By applying a voltage to the light-emitting layer between the electrodes, electrons and holes injected from the electrodes are emitted. When the molecules recombine, the luminescent material becomes excited, and light is emitted when the excited state returns to the ground state. As for the type of excited state, similar to the case of photoexcitation mentioned above, there is a singlet excited state. (S * ) and triplet excited states (T * ) is possible. In addition, the statistical The generation ratio is S * :T * It is believed that the ratio is 1:3.

[0008] Compounds that convert the singlet excited state into luminescence (hereafter referred to as fluorescent compounds) are No emission from the triplet excited state (phosphorescence) was observed, but emission from the singlet excited state (fluorescence) was observed. Therefore, the internal quantum efficiency ( The theoretical limit for the ratio of photons generated to the number of injected carriers is S * :T * =1: It is said to be 25% based on the fact that

[0009] On the other hand, if the above-mentioned phosphorescent compounds are used, the internal quantum efficiency can be theoretically increased to 75-100%. In other words, the luminous efficiency is three to four times higher than that of fluorescent compounds. For this reason, in order to realize a highly efficient light-emitting element, a light-emitting element using a phosphorescent compound has been developed. In recent years, the development of phosphorescent compounds has been actively pursued. In addition, organometallic complexes with iridium as a central metal have been attracting attention (for example, see Patent Document 1, see Patent Document 2 and Patent Document 3. ). [Prior art documents] [Patent documents]

[0010] [Patent Document 1] JP 2007-137872 A [Patent Document 2] JP 2008-069221 A [Patent Document 3] International Publication No. 2008-035664 Brochure Summary of the Invention [Problem to be solved by the invention]

[0011] As reported in the above-mentioned Patent Documents 1 to 3, various emission colors are exhibited. Although the development of phosphorescent materials is progressing, there are currently few reports of red materials with good color purity.

[0012] In view of this, in one embodiment of the present invention, a novel substance having a new skeleton is provided, which has high emission efficiency and In addition, the half-width of the emission spectrum is narrowed, providing an organometallic complex with improved color purity. In addition, a new organometallic complex with excellent sublimability is provided. A device, a light-emitting device, an electronic device, or a lighting device is provided. [Means for solving the problem]

[0013] One aspect of the present invention is a six-membered heteroaromatic ring containing two or more nitrogen atoms, including the nitrogen atom of the coordination atom, and a β- The present invention is an organometallic complex having a diketone as a ligand. 1) is an organometallic complex containing the structure represented by the formula:

[0014] [ka]

[0015] In the formula, X is substituted or unsubstituted and contains two or more nitrogen atoms, including the nitrogen of the coordinating atom. The heteroaromatic ring is a 6-membered ring. The type of the substituent bonded to X is a substituted or an unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group, or A phenyl group having a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms is also included. R 1 ~R 4 represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[0016] In the above general formula (G1), R 1 and R 2 are substituted or unsubstituted carbons, respectively. The dihedral angle of the benzene ring bonded to the iridium is 1 to 6. As will be described later, by increasing the dihedral angle, the organometallic It is theoretically possible to reduce the second peak in the emission spectrum of the complex and narrow the half-width. In addition, R 1 and R 2 is particularly preferably a methyl group.

[0017] In the above structure, nitrogen, including the nitrogen of the coordinating atom, which may be substituted or unsubstituted, is preferably 2 The 6-membered heteroaromatic ring is any one of the general formulas (X1) to (X4). preferable.

[0018] [ka]

[0019] In the formula, R 5 ~R 15 are each hydrogen or a substituted or unsubstituted carbon atom having 1 to 1 6 alkyl group or a substituted or unsubstituted phenyl group. The type of the substituent to be bonded includes a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. can be done.

[0020] Another embodiment of the present invention is an organometallic complex represented by the following general formula (G2).

[0021] [ka]

[0022] In the formula, R 1 ~R 4 Each represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. R 5 ~R 7are each a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, represents a substituted or unsubstituted phenyl group. 5 , R 6 may be hydrogen.

[0023] Another embodiment of the present invention is an organometallic complex represented by the following general formula (G3).

[0024] [ka]

[0025] In the formula, R 1 ~R 4 Each represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. Also, R 8 ~R 10 Each represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. R represents a phenyl group or a substituted or unsubstituted phenyl group. 8 and R 10 may be hydrogen.

[0026] Another embodiment of the present invention is an organometallic complex represented by the following general formula (G4).

[0027] [ka]

[0028] In the formula, R 1 ~R 4 Each represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. Also, R 11 ~R 13 are hydrogen or a substituted or unsubstituted carbon atom R represents an alkyl group having a molecular weight of 1 to 6, or a substituted or unsubstituted phenyl group. 11 Can be hydrogen Preferably R 12 or R 13Either one of them may be hydrogen.

[0029] Another embodiment of the present invention is an organometallic complex represented by the following general formula (G5).

[0030] [ka]

[0031] In the formula, R 1 ~R 4 Each represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. Also, R 14 , R 15 Each represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. R represents a phenyl group, or a substituted or unsubstituted phenyl group. 14 , R 15 may be hydrogen.

[0032] Another embodiment of the present invention is an organometallic complex represented by the following structural formula (100).

[0033] [ka]

[0034] Another embodiment of the present invention is an organometallic complex represented by the following structural formula (107).

[0035] [ka]

[0036] Another embodiment of the present invention is an organometallic complex represented by the following structural formula (108).

[0037] [ka]

[0038] Another embodiment of the present invention is an organometallic complex represented by the following structural formula (109).

[0039] [ka]

[0040] In addition, the organometallic complex according to one embodiment of the present invention can emit phosphorescence. Since light emission from the excited doublet state can be obtained and light emission can be exhibited, it is suitable for use as a light-emitting element. By applying this method, it is possible to increase the efficiency, which is very effective. The present invention also includes a light-emitting element using an organometallic complex which is one embodiment of the present invention.

[0041] Furthermore, another embodiment of the present invention is an organometallic complex having a structure represented by General Formula (G0): This is a light-emitting element using a light-emitting substance.

[0042] [ka]

[0043] In the formula, X is substituted or unsubstituted and contains two or more nitrogen atoms, including the nitrogen of the coordinating atom. The heteroaromatic ring is a 6-membered ring. The type of the substituent bonded to X is a substituted or an unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group, or A phenyl group having a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms is also included. R 1 , R 2 represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[0044] In the above general formula (G0), R 1 and R 2 are substituted or unsubstituted carbons, respectively. The dihedral angle of the benzene ring bonded to the iridium is 1 to 6. As will be described later, by increasing the dihedral angle, the organometallic It is theoretically possible to reduce the second peak in the emission spectrum of the complex and narrow the half-width. This effect can be achieved by using a compound having a structure represented by general formula (G0) and derived from said structure. This effect can theoretically be obtained from any luminescent material that emits light, regardless of the structure of the other structures. Therefore, a light-emitting device that includes a structure represented by general formula (G0) and exhibits light emission derived from the structure An optical material (including polymers and composite materials) is one aspect of the present invention. 0) and emitting light derived from said structure. The light-emitting device using R is also one embodiment of the present invention. 1 and R 2 is a methyl group It is particularly preferred.

[0045] In the above structure, nitrogen, including the nitrogen of the coordinating atom, which may be substituted or unsubstituted, The 6-membered heteroaromatic ring containing 2 or more rings is any one of the general formulas (X1) to (X4). is preferred.

[0046] [ka]

[0047] In the formula, R 5 ~R 15 are each hydrogen or a substituted or unsubstituted carbon atom having 1 to 1 6 alkyl group or a substituted or unsubstituted phenyl group. The type of the substituent to be bonded includes a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. can be done.

[0048] Another embodiment of the present invention is not only a light-emitting device having a light-emitting element, but also an electric device having a light-emitting device. The term "light-emitting device" as used herein includes a child device and a lighting device. The term refers to an image display device or a light source (including a lighting device). For example, FPC (Flexible printed circuit) or T Module with CP (Tape Carrier Package) attached, TC A module with a printed wiring board at the end of P, or a light emitting element with COG (Chip On Gauge) The "On Glass" method allows all modules with ICs (integrated circuits) directly mounted to be illuminated. This is included in the device. Effect of the Invention

[0049] One embodiment of the present invention is a novel substance having a new skeleton, which has high emission efficiency and light emission spectrum. It is possible to provide an organometallic complex having improved color purity by narrowing the half-width of the spectrum. It is also possible to provide a new organometallic complex having excellent sublimation properties. By using such an organometallic complex, it is possible to produce light-emitting elements, light-emitting devices, electronic devices, and the like having high emission efficiency. In addition, a light-emitting element, a light-emitting device, an electronic device, and a lighting device having low power consumption can be provided. Equipment or lighting devices may be provided. [Brief description of the drawings]

[0050] [Figure 1] 1A to 1C are diagrams illustrating a structure of a light-emitting element. [Diagram 2] 1A to 1C are diagrams illustrating a structure of a light-emitting element. [Diagram 3] 1A to 1C are diagrams illustrating a structure of a light-emitting element. [Figure 4] 1A and 1B are diagrams illustrating a light-emitting device. [Diagram 5] 1A and 1B are diagrams illustrating a light-emitting device. [Figure 6] 1A to 1C are diagrams illustrating electronic devices. [Figure 7] 1A to 1C are diagrams illustrating electronic devices. [Figure 8] FIG. [Figure 9] 1H-NMR chart of the organometallic complex shown in structural formula (100). [Figure 10] UV-visible absorption and emission spectra of the organometallic complex shown in structural formula (100). [Figure 11] 1H-NMR chart of the organometallic complex shown in structural formula (107). [Figure 12] UV-visible absorption and emission spectra of the organometallic complex shown in structural formula (107). [Figure 13] 1H-NMR chart of the organometallic complex shown in structural formula (108). [Figure 14] UV-visible absorption and emission spectra of the organometallic complex shown in structural formula (108). [Figure 15] 1A to 1C are diagrams illustrating light-emitting elements. [Figure 16] FIG. 13 shows current density-luminance characteristics of the light-emitting element 1. [Figure 17] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 1. [Figure 18] FIG. 13 shows luminance vs. current efficiency characteristics of the light-emitting element 1. [Figure 19] FIG. 2 shows voltage-current characteristics of the light-emitting element 1. [Figure 20] FIG. 2 shows an emission spectrum of the light-emitting element 1. [Figure 21] FIG. 13 shows the reliability of the light-emitting element 1. [Figure 22] FIG. 13 shows the reliability of the light-emitting element 1. [Diagram 23] FIG. 13 shows current density-luminance characteristics of the light-emitting element 2. [Figure 24] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 2. [Diagram 25] FIG. 13 shows luminance vs. current efficiency characteristics of Light-emitting Element 2. [Figure 26] FIG. 13 shows voltage-current characteristics of the light-emitting element 2. [Figure 27] FIG. 2 shows an emission spectrum of the light-emitting element 2. [Figure 28] FIG. 13 shows the reliability of the light-emitting element 2. [Figure 29] FIG. 13 shows the reliability of the light-emitting element 2. [Diagram 30] FIG. 13 shows current density-luminance characteristics of the light-emitting element 3. [Diagram 31] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 3. [Diagram 32] FIG. 13 shows luminance vs. current efficiency characteristics of the light-emitting element 3. [Diagram 33] FIG. 13 shows voltage-current characteristics of the light-emitting element 3. [Diagram 34] FIG. 2 shows an emission spectrum of the light-emitting element 3. [Diagram 35] FIG. 13 shows the reliability of the light-emitting element 3. [Diagram 36] FIG. 13 shows the reliability of the light-emitting element 3. [Figure 37] FIG. 2 shows the results of TG-DTA measurement of the organometallic complex represented by the structural formula (100). [Figure 38] FIG. 1 shows the phosphorescence spectra of [Ir(ppr)2(acac)] (abbreviation) and [Ir(dmppr)2(acac)] (abbreviation). [Figure 39] A comparison of the dihedral angles of the benzene rings of [Ir(ppr)2(acac)] (abbreviation) and [Ir(dmppr)2(acac)] (abbreviation). [Diagram 40] 1H-NMR chart of the organometallic complex shown in structural formula (121). [Diagram 41] UV-visible absorption and emission spectra of the organometallic complex shown in structural formula (121). [Diagram 42] FIG. 2 shows the results of TG-DTA measurement of the organometallic complex represented by the structural formula (121). [Diagram 43] 1H-NMR chart of the organometallic complex shown in structural formula (122). [Diagram 44]UV-visible absorption and emission spectra of the organometallic complex shown in structural formula (122). [Diagram 45] FIG. 2 shows the results of TG-DTA measurement of the organometallic complex represented by the structural formula (122). [Figure 46] FIG. 2 shows the results of LC-MS measurement of the organometallic complex represented by structural formula (122). [Figure 47] 1H-NMR chart of the organometallic complex shown in structural formula (123). [Figure 48] UV-visible absorption and emission spectra of the organometallic complex shown in structural formula (123). [Figure 49] FIG. 2 shows the results of LC-MS measurement of the organometallic complex represented by structural formula (123). [Figure 50] 1H-NMR chart of the organometallic complex shown in structural formula (124). [Figure 51] UV-visible absorption and emission spectra of the organometallic complex shown in structural formula (124). [Figure 52] FIG. 2 shows the results of TG-DTA measurement of the organometallic complex represented by the structural formula (124). [Figure 53] FIG. 2 shows the results of LC-MS measurement of the organometallic complex represented by structural formula (124). [Figure 54] 1H-NMR chart of the organometallic complex shown in structural formula (125). [Figure 55] UV-visible absorption and emission spectra of the organometallic complex shown in structural formula (125). [Figure 56] FIG. 2 shows the results of TG-DTA measurement of the organometallic complex represented by the structural formula (125). [Figure 57] FIG. 13 shows current density-luminance characteristics of light-emitting elements 4 to 7. [Figure 58] FIG. 13 shows voltage-luminance characteristics of light-emitting elements 4 to 7. [Figure 59] FIG. 13 shows luminance-current efficiency characteristics of light-emitting elements 4 to 7. [Figure 60] FIG. 13 shows voltage-current characteristics of light-emitting elements 4 to 7. [Figure 61] FIG. 13 shows emission spectra of light-emitting elements 4 to 7. [Figure 62] FIG. 1 shows the reliability (1) of light-emitting elements 4 to 7. [Figure 63] FIG. 13 shows the reliability (2) of light-emitting elements 4 to 7. [Figure 64] 1H-NMR chart of the organometallic complex shown in structural formula (126). [Figure 65] 1H-NMR chart of the organometallic complex shown in structural formula (127). [Figure 66] 1H-NMR chart of the organometallic complex shown in structural formula (106). DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0051] Hereinafter, the embodiment of the present invention will be described in detail with reference to the drawings. The present invention is not limited to the above description, and the embodiments and details thereof are not limited to those described above without departing from the spirit and scope of the present invention. Therefore, the present invention is not limited to the embodiments described below. It is not to be construed as being limited to the content.

[0052] (Embodiment 1) In this embodiment, an organometallic complex which is one embodiment of the present invention will be described.

[0053] The organometallic complex according to one embodiment of the present invention is a six-membered ring containing two or more nitrogen atoms, including the nitrogen atom of the coordination atom. The present invention is an organometallic complex having a heteroaromatic ring and a β-diketone as a ligand. The compound is a six-membered heteroaromatic ring containing two or more nitrogen atoms, including the nitrogen atom of the coordinating atom to be described, and is coordinated with a β-diketone. One embodiment of the organometallic complex having the ligand is an organometallic complex having a structure represented by the following general formula (G1): It is a complex.

[0054] [ka]

[0055] In the general formula (G1), X is substituted or unsubstituted and is a nitrogen atom, including a nitrogen atom of a coordination atom. R represents a six-membered heteroaromatic ring containing two or more atoms. 1 ~R 4 are respectively substituted or It represents an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0056] In addition, R 1 ~R 4 Specific examples of the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms in the above are as follows: Examples include methyl, ethyl, propyl, isopropyl, butyl, and sec-butyl. group, isobutyl group, tert-butyl group, pentyl group, isopentyl group, sec-pentyl group hexyl, tert-pentyl, neopentyl, hexyl, isohexyl, sec- Hexyl group, tert-hexyl group, neohexyl group, 3-methylpentyl group, 2-methyl butyl group, 2-ethylbutyl group, 1,2-dimethylbutyl group, 2,3-dimethylbutyl group Examples include the aryl group.

[0057] In addition, a 6-membered ring complex containing two or more nitrogen atoms, including the nitrogen of the coordinating atom, which may be substituted or unsubstituted, Specific examples of the aromatic ring X include any one of the following general formulas (X1) to (X4). is preferred.

[0058] [ka]

[0059] Note that the organometallic complex of one embodiment of the present invention may have a substituted or unsubstituted coordinating atom. Bonded to a 6-membered heteroaromatic ring containing two or more nitrogen atoms, including nitrogen, and bonded to metallic iridium The phenyl group is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and is bonded to iridium. The resulting structure is substituted at the 2- and 4-positions of the bound phenyl group. The half-width of the emission spectrum is narrowed, which has the advantage of improving color purity. In addition, the ligand has a β-diketone structure, which improves the organic solubility of the organometallic complex. This is preferable because it increases the solubility in the solvent and facilitates purification. This is preferable because it is possible to obtain an organometallic complex with high luminescence efficiency. The presence of the TON structure provides the advantage of improved sublimation properties and excellent deposition performance.

[0060] Another embodiment of the present invention is an organometallic complex represented by the following general formula (G2).

[0061] [ka]

[0062] In general formula (G2), R 1 ~R 4 are substituted or unsubstituted carbon atoms having 1 to 6 carbon atoms. R represents an alkyl group. 5 ~R 7 are substituted or unsubstituted aryl groups having 1 to 6 carbon atoms. R represents an alkyl group, or a substituted or unsubstituted phenyl group. 5 , R 6 Can be hydrogen Also, R 1 ~R 7 Some of the specific examples of R in general formula (G1) 1 ~R 4 It is the same as R 5 ~R 7 The substituted or unsubstituted phenyl group in It may have a substituted alkyl group having 1 to 6 carbon atoms.

[0063] Another embodiment of the present invention is an organometallic complex represented by the following general formula (G3).

[0064] [ka]

[0065] In general formula (G3), R 1 ~R 4 are substituted or unsubstituted carbon atoms having 1 to 6 carbon atoms. In addition, R 8 ~R 10 are substituted or unsubstituted carbon atoms having 1 to R represents an alkyl group represented by the formula (I) of R 6, or a substituted or unsubstituted phenyl group. 8 and R 1 0 may be hydrogen. 1 ~R 4 and R 8 ~R 10 Some of the specific examples of the general formula (G 1) R 1 ~R 4 It is the same as R 8 ~R 10 In the substituted or unsubstituted The phenyl group may have a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. stomach.

[0066] Another embodiment of the present invention is an organometallic complex represented by the following general formula (G4).

[0067] [ka]

[0068] In general formula (G4), R 1 ~R 4 are substituted or unsubstituted carbon atoms having 1 to 6 carbon atoms. In addition, R 11 ~R 13are each hydrogen, or a substituted or unsubstituted It represents a substituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. R 11 may be hydrogen, preferably R 12 or R 13 Either one of the groups may be hydrogen. , R 1 ~R 4 and R 11 ~R 13 Some of the specific examples of R in general formula (G1) 1 ~R 4 Same as Also, R 11 ~R 13 The substituted or unsubstituted phenyl group in It may have a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[0069] Another embodiment of the present invention is an organometallic complex represented by the following general formula (G5).

[0070] [ka]

[0071] In general formula (G5), R 1 ~R 4 are substituted or unsubstituted carbon atoms having 1 to 6 carbon atoms. In addition, R 14 , R 15 are substituted or unsubstituted carbon atoms each having 1 R represents an alkyl group having a molecular weight of 1 to 6, or a substituted or unsubstituted phenyl group. 14 , R 1 5 may be hydrogen. 1 ~R 4 and R 14 , R 15 Some of the specific examples are represented by the general formula ( G1) R 1 ~R 4 It is the same as R14 , R 15 Substitution or non-substitution in The phenyl group has a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. Good too.

[0072] Next, specific structural formulas of the organometallic complexes according to embodiments of the present invention will be shown. Formulae (100) to (127). However, the present invention is not limited to these.

[0073] [ka]

[0074] [ka]

[0075] [ka]

[0076] [ka]

[0077] The organometallic complexes represented by the above structural formulas (100) to (127) emit phosphorescence. These are new substances that can be used for the synthesis of fluorinated compounds. The organometallic complex according to one embodiment of the present invention includes these isomers and stereoisomers. Also includes all.

[0078] Next, an example of a method for synthesizing an organometallic complex containing the structure represented by the above general formula (G1) will be described. explain.

[0079] <Synthesis method of 6-membered heterocyclic derivatives represented by general formula (G0-X1)> An example of a method for synthesizing a 6-membered heterocyclic derivative represented by the following general formula (G0-X1) explain.

[0080] [ka]

[0081] In the general formula (G0-X1), R 1 , R 2 and R 5 ~R 7 are replaced by or an unsubstituted alkyl group having 1 to 6 carbon atoms. 5 , R 6 may be hydrogen.

[0082] Below are four types of pyrazine derivatives, which are 6-membered heterocyclic rings represented by the general formula (G0-X1). The synthesis schemes (A1), (A2), (A3), and (A4) of the above compounds are shown below.

[0083] [ka]

[0084] [ka]

[0085] In the synthesis scheme (A1), a 3,5-disubstituted phenyl halide (a1-1) is The derivative ( G0-X1).

[0086] In addition, in the synthetic scheme (A2), 3,5-disubstituted phenyl boronic acid (a1-2) and By coupling with pyrazine halide (a2-2), the derivative (G0- X1) can be obtained.

[0087] In addition, in the synthetic scheme (A3), 3,5-disubstituted phenyl diketone (a1-3) and By reacting with diamine (a2-3), derivative (G0-X1) can be obtained. do.

[0088] In addition, in the synthetic scheme (A4), 3,5-disubstituted phenyl pyrazine (a1-4) and The derivative (G 0-X1), where Y represents a halogen element.

[0089] In addition to the four methods mentioned above, there are several other known synthetic methods for the synthesis of derivatives (G0-X1). Therefore, either method may be used.

[0090] In addition, compounds (a1-1), (a2-1), (a1-2), and (a2- 2), (a1-3), (a2-3), (a1-4), and (a2-4) are available in various types on the market. Since pyrazine represented by the general formula (G0-X1) is either known or can be synthesized, Numerous types of derivatives can be synthesized. Metal complexes are characterized by a wide variety of ligands.

[0091] <<Method for Synthesizing Organometallic Complex Represented by General Formula (G1) of One Embodiment of the Present Invention>> Next, a compound represented by the general formula (G0) is used to form a 6-membered heterocyclic derivative represented by the general formula ( A method for synthesizing an organometallic complex (G1) according to one embodiment of the present invention will now be described. do. [ka]

[0092] In the general formula (G1), X is substituted or unsubstituted and is a nitrogen atom of the coordination atom. It represents a 6-membered heteroaromatic ring containing two or more nitrogen atoms. 1 ~R 4 are also replaced or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0093] The synthesis scheme (B) of the organometallic complex represented by the general formula (G1) is shown below.

[0094] [ka]

[0095] In the synthesis scheme (B), X is substituted or unsubstituted, and the nitrogen of the coordination atom is It represents a 6-membered heteroaromatic ring containing two or more nitrogen atoms, including nitrogen atoms. Y represents a halogen, and R 1 , R 2 represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[0096] As shown in the above synthesis scheme (B), a 6-membered heterocyclic derivative represented by the general formula (LG0) is synthesized. Conductors and iridium compounds containing halogens (iridium chloride, iridium bromide, iridium iodide, etc.) Lithium, etc.) without solvent or in alcohol-based solvents (glycerol, ethylene glycol, etc.) Alcohols (e.g., 2-methoxyethanol, 2-ethoxyethanol, etc.) By using a mixture of one or more system solvents and water and heating in an inert gas atmosphere, The present invention provides a binuclear complex (P), which is a type of organometallic complex having a halogen-bridged structure. This can be done.

[0097] The heating means is not particularly limited, and may be an oil bath, a sand bath, or an aluminum block. Alternatively, microwaves may be used as a heating means.

[0098] Furthermore, as shown in the following synthesis scheme (C), By reacting the dinuclear complex (P) with a β-diketone derivative in an inert gas atmosphere, The proton of the β-diketone derivative is eliminated, and the monoanion β-diketone derivative is formed at the center. An organometallic complex according to one embodiment of the present invention, which is coordinated to metallic iridium and is represented by General Formula (G1): is obtained.

[0099] [ka]

[0100] In the synthesis scheme (C), X is substituted or unsubstituted, and the nitrogen of the coordination atom is It represents a 6-membered heteroaromatic ring containing two or more nitrogen atoms, including nitrogen atoms. Y represents a halogen, and R 1 ~R 4 represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[0101] The heating means is not particularly limited, and may be an oil bath, a sand bath, or an aluminum block. Alternatively, microwaves may be used as a heating means.

[0102] An example of a method for synthesizing an organometallic complex according to one embodiment of the present invention has been described above. The light is not limited to this, and may be synthesized by any other synthesis method.

[0103] Note that the organometallic complex which is one embodiment of the present invention can emit phosphorescence. Therefore, it can be used as a light-emitting material or a light-emitting substance for a light-emitting element.

[0104] In addition, by using the organometallic complex which is one embodiment of the present invention, a light-emitting element with high emission efficiency can be obtained. A light-emitting device, an electronic device, or a lighting device can be realized. An optical element, a light emitting device, an electronic device, or a lighting device can be realized.

[0105] The structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiments. This can be done.

[0106] (Embodiment 2) In this embodiment, the organometallic complex described in Embodiment 1 is used as an embodiment of the present invention. The light emitting element used in the present invention will be described with reference to FIG.

[0107] The light-emitting element shown in this embodiment has a pair of electrodes (first electrode (anode) 1) as shown in FIG. An EL layer 102 including a light-emitting layer 113 is sandwiched between a first electrode (cathode) 101 and a second electrode (cathode) 103. In addition to the light-emitting layer 113, the EL layer 102 includes a hole injection layer 111, a hole injection layer 112, and a hole injection layer 113. or hole) transport layer 112, electron transport layer 114, electron injection layer 115, charge generation layer (E ) 116 and the like.

[0108] By applying a voltage to such a light emitting element, the 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. This causes the organometallic complex to enter an excited state. The excited organometallic complex then returns to the ground state. Thus, in one embodiment of the present invention, an organometallic complex is It functions as a luminescent material.

[0109] The hole-injection layer 111 in the EL layer 102 is made of a material having a high hole-transporting property and an acceptor. The layer contains an acceptor material, and electrons are transferred from a material with high hole transport properties to the acceptor material. As a result, holes are generated from the hole injection layer 111. Holes are injected into the light-emitting layer 113 through the transport layer 112 .

[0110] The charge generating layer (E) 116 contains a substance having a high hole transporting property and a substance having an acceptor property. The acceptor material removes electrons from the material with high hole transport properties, Therefore, the electrons that are extracted pass through the electron transport layer 114 from the electron injection layer 115 that has electron injection properties. The electrons are injected into the light-emitting layer 113 via the ion beam.

[0111] A specific example of manufacturing the light-emitting element described in this embodiment mode will be described below.

[0112] The first electrode (anode) 101 and the second electrode (cathode) 103 are made of a metal, an alloy, an electrically conductive material, or Conductive compounds and mixtures thereof can be used. Indium-tin oxide (ITO), silicon or silicon oxide Indium oxide-tin oxide and indium oxide-zinc oxide (Indium Zi nc Oxide), indium oxide containing tungsten oxide and zinc oxide, gold (A u), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo) Mo, Fe, Co, Cu, Pd, Ti In addition to Ti, elements in the first or second group of the periodic table, namely lithium (L i) and alkali metals such as cesium (Cs), calcium (Ca), and strontium Alkaline earth metals such as Sr, magnesium (Mg), and alloys containing these metals (Mg Rare earth metals such as Ag, AlLi), europium (Eu), ytterbium (Yb) and The first electrode (anode) may be a cathode material, an alloy containing the above-mentioned, or graphene. The first electrode (cathode) 101 and the second electrode (cathode) 103 are formed by, for example, sputtering or deposition (vacuum The thin film can be formed by a method such as vapor deposition.

[0113] The hole transport layer used in the hole injection layer 111, the hole transport layer 112, and the charge generation layer (E) 116 An example of a substance with high transportability is 4,4'-bis[N-(1-naphthyl)-N-phenyl N,N'-bis(3-methylamino)biphenyl (abbreviation: NPB or α-NPD) Phenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine ( Abbreviation: TPD), 4,4',4''-tris(carbazol-9-yl)triphenyl TCTA, 4,4',4''-tris(N,N-diphenylamino)triamine Phenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl) (phenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4' -Bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]bi Aromatic amine compounds such as 3-[N-(9-phenylcarbamoyl)phenyl (abbreviation: BSPB), PC(3-yl)-N-phenylamino]-9-phenylcarbazole zPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenyl Nylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1- naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazol Other examples include 4,4'-di(N-carbazol) and 4,4'-di(N-carbazol). 1,3,5-tris[4-(N-carbazolyl) phenyl]benzene (abbreviation: TCPB), 9-[4-(10-phenyl-9-anthracene carbazole derivatives such as [9H-carbazole (abbreviation: CzPA)], etc. The substances mentioned here are mainly 10 -6 cm 2 Hole transfer above / Vs However, other than these, any other material that has a higher hole transporting property than an electron transporting property may be used. may also be used.

[0114] In addition, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriflate) 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'-bis (phenyl)benzidine (abbreviation: Poly-TPD) and other polymer compounds. It is also possible.

[0115] In addition, the acceptor material used in the hole injection layer 111 and the charge generation layer (E) 116 Specifically, transition metal oxides and oxides of metals belonging to groups 4 to 8 of the periodic table are Specifically, molybdenum oxide is particularly preferred.

[0116] The light-emitting layer 113 is formed using the organometallic complex described in Embodiment 1 as a guest material serving as a light-emitting substance. The organometallic complex is then used as a host material with a triplet excitation energy greater than that of the organometallic complex. It is a layer formed using

[0117] Also, a substance used to disperse the organometallic complex (i.e., a host material) For example, 2,3-bis(4-diphenylaminophenyl)quinoxaline (abbreviation: In addition to compounds with arylamine skeletons such as TPAQn and NPB, CBP, 4,4 ',4''-Tris(carbazol-9-yl)triphenylamine (abbreviation: TCTA) Carbazole derivatives such as bis[2-(2-hydroxyphenyl)pyridinato]zinc ( Abbreviation: Znpp 2 ), bis[2-(2-hydroxyphenyl)benzoxazolato]zinc (Abbreviation: Zn(BOX) 2 ), bis(2-methyl-8-quinolinolato)(4-phenyl (8-quinolinolato)aluminum (abbreviation: BAlq), tris(8-quinolinolato)aluminum (Abbreviation: Alq 3 Metal complexes such as PVK are also preferred. It is also possible.

[0118] In the light-emitting layer 113, the above-mentioned organometallic complex (guest material) and the host material are By forming the light-emitting layer 113 containing the fluorine atom, phosphorescence with high luminous efficiency can be obtained from the light-emitting layer 113. can.

[0119] The electron transport layer 114 is a layer containing a substance with a high electron transport property. Alq 3 , Tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq 3 ) , Bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq 2 ), BAlq, Zn(BOX) 2 , bis[2-(2-hydroxyphenyl)benzothiazol ]Zinc (abbreviation: Zn(BTZ) 2) and other metal complexes can be used. 4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazide PBD, 1,3-bis[5-(p-tert-butylphenyl)-1, 3,4-Oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-te rt-Butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triphenyl Azole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethyl Phenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtT AZ), Bathophenanthroline (abbreviation: BPhen), Bathocuproine (abbreviation: BCP ), 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: B Heteroaromatic compounds such as poly(2,5-pyridine) 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. As long as the substance has a higher electron transporting property than the above, the electron-transporting layer 114 can be formed using any substance other than the above. This is also fine.

[0120] The electron transport layer 114 may be a single layer or may be a laminate of two or more layers of the above-mentioned materials. It may also be layered.

[0121] The electron injection layer 115 is a layer containing a substance with high electron injection properties. Lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ) , lithium oxide (LiOx), etc., alkaline metals, alkaline earth metals, or the like Compounds such as these can be used. Erbium fluoride (ErF 3 ) such as rare earths Metal compounds can be used. In addition, the above-mentioned material constituting the electron transport layer 114 can be used. You can also be there.

[0122] Alternatively, the electron injection layer 115 may be formed by mixing an organic compound and an electron donor. Composite materials may also be used. Such composite materials are made by adding electrons to organic compounds by electron donors. In this case, the organic compound is In particular, the material is preferably one that is excellent in transporting the generated electrons. 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. Specifically, alkali metals, alkaline earth metals and rare earth metals are preferred, and lithium, cesium, etc. Examples of the elements include aluminum, magnesium, calcium, erbium, and ytterbium. Alkali metal oxides and alkaline earth metal oxides are preferred, with lithium oxide, calcium Examples of the oxide include barium oxide and magnesium oxide. Also, organic compounds such as tetrathiafulvalene (TTF) can be used. You can also be there.

[0123] The hole injection layer 111, the hole transport layer 112, the light emitting layer 113, and the electron transport layer 11 4, the electron injection layer 115, and the charge generation layer (E) 116 are formed by deposition (including vacuum deposition). The insulating layer can be formed by a method such as an ink jet method or a coating method.

[0124] In the above-described light-emitting element, a potential difference generated between the first electrode 101 and the second electrode 103 Current flows due to this, and holes and electrons recombine in the EL layer 102 to emit light. This light emission is caused by either the first electrode 101 or the second electrode 103 or Therefore, the first electrode 101 and the second electrode 103 are connected to each other. Either one or both of the electrodes is a light-transmitting electrode.

[0125] The light-emitting element described above can emit phosphorescence based on an organometallic complex. As compared with a light-emitting element using a fluorescent compound, a light-emitting element with higher efficiency can be realized.

[0126] Note that the light-emitting element described in this embodiment uses an organometallic complex which is one embodiment of the present invention. The light emitting device may be configured as follows: In addition to passive matrix type light-emitting devices and active matrix type light-emitting devices, A microcavity structure having a light emitting element having a structure different from that described in the embodiment. It is possible to manufacture a light emitting device having such a structure, and all of these are included in the present invention. do.

[0127] In the case of an active matrix type light emitting device, the structure of the TFT is not particularly limited. For example, a staggered or inverted staggered TFT can be used as appropriate. The driver circuit formed on the FT substrate may consist of N-type and P-type TFTs. Alternatively, it may be composed of only one of N-type TFTs or P-type TFTs. Furthermore, there is no particular limitation on the crystallinity of the semiconductor film used in the TFT. An amorphous semiconductor film, a crystalline semiconductor film, an oxide semiconductor film, or the like can be used.

[0128] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiments. It is possible to do so.

[0129] (Embodiment 3) In this embodiment, in addition to an organometallic complex, two or more other compounds are used as an embodiment of the present invention. A light-emitting device using an organic compound in a light-emitting layer will be described.

[0130] The light-emitting element shown in this embodiment has a pair of electrodes (anode 201 and cathode 202) as shown in FIG. 02) has an EL layer 203 between the two layers. The layer 204 includes a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge generation layer, and the like. The layer (E) may include a hole injection layer, a hole transport layer, an electron transport layer, an electron For the injection layer and the charge generation layer (E), the substances shown in Embodiment Mode 2 can be used.

[0131] The light-emitting layer 204 shown in this embodiment is a phosphorescent layer using the organometallic complex shown in Embodiment 1. The photo-active compound 205, the first organic compound 206, and the second organic compound 207 are included. The phosphorescent compound 205 is a guest material in the light-emitting layer 204. The proportion of the first organic compound 206 and the second organic compound 207 contained in the light-emitting layer 204 The material with the larger ratio is used as the host material in the light-emitting layer 204 .

[0132] In the light-emitting layer 204, the guest material is dispersed in the host material. This makes it possible to suppress the crystallization of the light-emitting layer. Concentration quenching can be suppressed, and the luminous efficiency of the light-emitting device can be increased.

[0133] The triplet excited energies of the first organic compound 206 and the second organic compound 207 are The energy level (T1 level) of the phosphorescent compound 205 is preferably higher than the T1 level of the phosphorescent compound 205. The T1 level of the first organic compound 206 (or the second organic compound 207) is a phosphorescent compound. If the triplet excitation energy of the phosphorescent compound 205 is lower than the T1 level of the phosphorescent compound 205, the triplet excitation energy of the phosphorescent compound 205 that contributes to the emission is The first organic compound 206 (or the second organic compound 207) quenches the ghee. This leads to a decrease in luminous efficiency.

[0134] Here, in order to increase the efficiency of energy transfer from the host material to the guest material, The Förster mechanism (dipole-dipole interaction) and Taking into account the Dexter mechanism (electron exchange interaction), the emission spectrum of the host material ( When discussing energy transfer from a singlet excited state, the fluorescence spectrum is used. When discussing energy transfer from a triplet excited state, the When discussing the energy transfer from the guest material, the phosphorescence spectrum is used. More specifically, the spectrum overlaps with the absorption band on the longest wavelength (lowest energy) side. However, it is usually desirable to make the fluorescence spectrum of the host material larger than that of the guest material. It is difficult to overlap the absorption spectrum with that of the material at its longest wavelength (lowest energy) absorption band. This is difficult because the phosphorescence spectrum of the host material would then be dominated by the fluorescence spectrum. Since the T1 level of the host material is located on the longer wavelength (lower energy) side than the This is because the T1 level of the compound would fall below the T1 level, causing the quenching problem described above. On the other hand, to avoid the quenching problem, the T1 level of the host material is set to be equal to the T1 level of the phosphorescent compound. If the fluorescent spectrum of the host material is designed to exceed the high energy level, the fluorescent spectrum of the host material will become shorter (higher energy). The fluorescence spectrum shifts to the longest wavelength (low energy) of the guest material. Therefore, the absorption spectrum of the host material does not overlap with that of the absorption band on the - side. The light spectrum is the absorption spectrum in the longest wavelength (lowest energy) absorption band of the guest material. By stacking the dopant with the host material, it is possible to maximize the energy transfer from the singlet excited state of the host material. , which is usually difficult.

[0135] Therefore, in this embodiment, the first organic compound 206 and the second organic compound 207 is preferably a combination that forms an excited complex (also called an exciplex). In this case, the first electrons and holes are generated during recombination of carriers (electrons and holes) in the light-emitting layer 204. The organic compound 206 and the second organic compound 207 form an exciplex. This causes light emission. In the layer 204, the fluorescence spectrum of the first organic compound 206 and the fluorescence spectrum of the second organic compound 207 are The fluorescence spectrum of 07 is converted to the emission spectrum of the exciplex located at longer wavelengths. In addition, the emission spectrum of the exciplex largely overlaps with the absorption spectrum of the guest material. If the first organic compound 206 and the second organic compound 207 are selected so that This maximizes the energy transfer from the excited state. It is believed that energy transfer occurs from the exciplex rather than from the host material.

[0136] As the phosphorescent compound 205, the organometallic complex described in Embodiment 1 is used. The first organic compound 206 and the second organic compound 207 are a combination that generates an exciplex. However, there are compounds that easily accept electrons (electron trapping compounds) and compounds that easily accept holes. It is preferable to combine it with a compound that is easy to receive (a hole-trapping compound).

[0137] An example of a compound that readily accepts electrons is 2-[3-(dibenzothiophene-4 -yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II ), 2-[4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl]dibe Benzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(dibenzo Thiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBT PDBq-II) and 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzyl Examples include quinoxaline (abbreviation: 6mDBTPDBq-II).

[0138] Compounds that readily accept holes include 4-phenyl-4'-(9-phenyl (9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), 3 -[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9 -phenylcarbazole (abbreviation: PCzPCN1), 4,4',4''-tris[N-( 1-Naphthyl)-N-phenylamino]triphenylamine (abbreviation: 1'-TNATA) , 2,7-bis[N-(4-diphenylaminophenyl)-N-phenylamino]-spiro[ N,N'-bis(9-phenylcarbazone) 1,3-diamine (abbreviation: P CA2B), N-(9,9-dimethyl-2-N',N'-diphenylamino-9H-fluoro N,N',N''-triphenylamine (DPNF) N,N',N''-tris(9-phenylcarbazol-3-yl)benzene-1 ,3,5-triamine (abbreviation: PCA3B), 2-[N-(9-phenylcarbazole- 3-yl)-N-phenylamino]spiro-9,9'-bifluorene (abbreviation: PCASF ), 2-[N-(4-diphenylaminophenyl)-N-phenylamino]spiro-9, 9'-Bifluorene (abbreviation: DPASF), N,N'-bis[4-(carbazole-9- yl)phenyl]-N,N'-diphenyl-9,9-dimethylfluorene-2,7-diazo amine (abbreviation: YGA2F), 4,4'-bis[N-(3-methylphenyl)-N-phenyl N-(4-diphenylamino)biphenyl (abbreviation: TPD), 4,4'-bis[N-(4-diphenylamino) phenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), N-(9,9-dimethyl 9,9-dimethyl-2[N'-phenyl- N'-(9,9-dimethyl-9H-fluoren-2-yl)amino]-9H-fluorene -7-yl}phenylamine (abbreviation: DFLADFL), 3-[N-(9-phenylcarbamoyl) PC(3-yl)-N-phenylamino]-9-phenylcarbazole zPCA1), 3-[N-(4-diphenylaminophenyl)-N-phenylamino]- 9-Phenylcarbazole (abbreviation: PCzDPA1), 3,6-bis[N-(4-diphenyl N-phenylaminophenyl)-9-phenylcarbazole (abbreviation: PC zDPA2), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenyl phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 3 ,6-Bis[N-(4-diphenylaminophenyl)-N-(1-naphthyl)amino]- 9-Phenylcarbazole (abbreviation: PCzTPN2), 3,6-bis[N-(9-phenyl [N-phenylamino]-9-phenylcarbazole (abbreviation :PCzPCA2).

[0139] The first organic compound 206 and the second organic compound 207 are not limited to the above. This is a combination that can form an exciplex without any problem, and the emission spectrum of the exciplex is phosphorescent. The absorption spectrum of the exciplex overlaps with that of the phosphorescent compound 205, and the emission spectrum of the exciplex is at the peak of the phosphorescent It is sufficient that the wavelength is longer than the peak of the absorption spectrum of the active compound 205.

[0140] The first organic compound is composed of a compound that easily accepts electrons and a compound that easily accepts holes. When the second organic compound 206 and the second organic compound 207 are mixed, the carrier balance is determined by the mixture ratio. Specifically, the ratio of the first organic compound to the second organic compound is 1:9. A range of ∼9:1 is preferred.

[0141] The light-emitting element described in this embodiment has an emission spectrum of an exciplex and an absorption spectrum of a phosphorescent compound. Energy transfer efficiency is improved by utilizing spectral overlap. Therefore, a light emitting device with high external quantum efficiency can be realized.

[0142] As another configuration included in the present invention, the other two phosphorescent compounds 205 (guest materials) As the organic compounds (the first organic compound 206 and the second organic compound 207), The light-emitting layer 204 is formed using a host molecule with an electron trapping property and a host molecule with an electron trapping property. The two host molecules are then coupled to a guest molecule, which is then transported to the guest molecule via a hole and an electron. Excitation phenomenon (i.e., Guest Coupled with Comple A structure in which the light-emitting layer 204 is formed so as to obtain a cationically-charged host (GCCH) is also possible.

[0143] In this case, the hole-trapping host molecule and the electron-trapping host molecule are The above-mentioned compounds that readily accept holes and compounds that readily accept electrons are It can be used.

[0144] Note that the light-emitting element shown in this embodiment mode is an example of a structure of a light-emitting element, but A light-emitting element having a different structure shown in another embodiment can be applied to the light-emitting device according to the present invention. In addition, the light emitting device having the light emitting element may be a passive matrix type light emitting device. In addition to the optical device and the active matrix type light emitting device, other devices different from those described in other embodiments may be used. A light emitting device having a microcavity structure including a light emitting element having the structure described above can be manufactured. and all of these are intended to be included in the present invention.

[0145] In the case of an active matrix type light emitting device, the structure of the TFT is not particularly limited. For example, a staggered or inverted staggered TFT can be used as appropriate. The driver circuit formed on the FT substrate may consist of N-type and P-type TFTs. Alternatively, it may be composed of only one of N-type TFTs or P-type TFTs. Furthermore, there is no particular limitation on the crystallinity of the semiconductor film used in the TFT. An amorphous semiconductor film, a crystalline semiconductor film, an oxide semiconductor film, or the like can be used.

[0146] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiments. It is possible to do so.

[0147] (Embodiment 4) In this embodiment, as one embodiment of the present invention, a structure having a plurality of EL layers sandwiching a charge generating layer is described. A light emitting device having this structure (hereinafter referred to as a tandem type light emitting device) will be described.

[0148] The light-emitting element shown in this embodiment has a pair of electrodes (first electrode 30) as shown in FIG. A plurality of EL layers (first EL layer 302(1), second EL layer 302(2), and second EL layer 304) are disposed between the first and second electrodes 302(3), 302(4), 302(5), 302(6), 302(7), 302(8), 302(9), 302(10), 302(11), 302(12), 302(13 This is a tandem type light emitting device having an L layer 302(2).

[0149] In this embodiment, the first electrode 301 is an electrode that functions as an anode, and the second The electrode 304 functions as a cathode. The structure of the EL layer 304 may be the same as that of the second embodiment. The first EL layer 302(1) and the second EL layer 302(2) are the same as those in the second embodiment or the The EL layer may have a similar structure to that shown in 3, or either of them may have a similar structure. That is, the first EL layer 302(1) and the second EL layer 302(2) have the same structure. The configuration may be the same as that of the second or third embodiment. can be applied.

[0150] In addition, between the multiple EL layers (the first EL layer 302(1) and the second EL layer 302(2)), The charge generating layer (I) 305 is provided on the first electrode. When a voltage is applied between the first electrode 301 and the second electrode 304, electrons are injected into one EL layer and the other In this embodiment, the first electrode 301 has a function of injecting holes into the EL layer. When a voltage is applied so that the potential becomes higher than that of the second electrode 304, the charge generating layer (I) 30 Electrons are injected from the first EL layer 302(1) to the second EL layer 302(2) and holes are injected from the second EL layer 302(3) to the first EL layer 302(1). It is injected.

[0151] From the viewpoint of light extraction efficiency, the charge generating layer (I) 305 is transparent to visible light. Specifically, the transmittance of visible light through the charge generating layer (I) 305 is 40% or more. In addition, the charge generating layer (I) 305 is preferably a first electrode 301 or a second electrode 302. It works even with conductivities lower than 04.

[0152] The charge generation layer (I) 305 is formed by adding an electron acceptor (acceptor) to an organic compound having high hole transport properties. ) is added, the electron donor (donor) is added to the organic compound with high electron transport properties. Alternatively, both of these structures may be laminated.

[0153] In the case where an electron acceptor is added to an organic compound having a high hole transporting property, Examples of organic compounds with high transportability include NPB, TPD, TDATA, and MTDATA. , 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenyl Aromatic amine compounds such as bisaminobiphenyl (abbreviation: BSPB) can be used. The substances mentioned here are mainly -6 cm 2 / Vs or more. However, if an organic compound has a higher hole transporting property than an electron transporting property, a substance other than the above may be used. That's fine.

[0154] In addition, 7,7,8,8-tetracyano-2,3,5,6-tetracyanophenylacetate can be used as an electron acceptor. Fluoroquinodimethane (abbreviation: F 4 -TCNQ), chloranil, etc. Further, transition metal oxides can be used. Specifically, vanadium oxide, niobium oxide, etc. , Tantalum oxide, Chromium oxide, Molybdenum oxide, Tungsten oxide, Manganese oxide, Oxide Rhenium is preferred because of its high electron-accepting property. In particular, molybdenum oxide is stable even in the atmosphere. It is preferable because it is stable, has low hygroscopicity, and is easy to handle.

[0155] On the other hand, in the case where an electron donor is added to an organic compound having high electron transport properties, As organic compounds with high electron transport properties, for example, Alq, Almq 3 , BeBq 2 , B Metal complexes having a quinoline or benzoquinoline skeleton, such as Alq, can be used. In addition, Zn(BOX) 2 , Zn(BTZ) 2 Oxazoles such as Metal complexes having azole-based ligands can also be used. However, PBD, OXD-7, TAZ, BPhen, BCP, etc. can also be used. The substances mentioned in are mainly -6 cm 2 / Vs or higher. Any organic compound having a higher electron transporting property than a hole transporting property may be used. stomach.

[0156] The electron donor may be an alkali metal, an alkaline earth metal, a rare earth metal, or or metals belonging to Groups 2 and 13 of the Periodic Table and their oxides and carbonates. Specifically, lithium (Li), cesium (Cs), magnesium (Mg ), calcium (Ca), ytterbium (Yb), indium (In), lithium oxide It is preferable to use cesium carbonate or the like. The compound may be used as an electron donor.

[0157] In addition, by forming the charge generating layer (I) 305 using the above-mentioned material, an EL layer is formed. When the layers are stacked, the increase in driving voltage can be suppressed.

[0158] In this embodiment mode, a light-emitting element having two EL layers has been described. As shown in the figure, n (n is 3 or more) EL layers (302(1) to 302(n)) are stacked. The same can be applied to a light emitting device in which the light emitting element is layered. In the case of a device having multiple EL layers between a pair of electrodes, By arranging the charge generating layers (I) (305(1) to 305(n-1)), the current density It is possible to emit light in a high brightness range while keeping the current density low. In addition, when applied to lighting, the voltage drop due to the resistance of the electrode material The size can be reduced, enabling uniform light emission over a large area. A light emitting device with low power consumption can be realized.

[0159] In addition, by making the emission color of each EL layer different, the light-emitting element as a whole can be For example, in a light-emitting device 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, the light of complementary colors and the light emitted by an object are achromatic. When mixed with the light obtained from the crystal, white light can be obtained.

[0160] The same applies to a light-emitting element having three EL layers. For example, The emission color of the first EL layer is red, the emission color of the second EL layer is green, and the emission color of the third EL layer is blue. In this case, the light emitting element as a whole can emit white light.

[0161] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiments. There can be.

[0162] (Embodiment 5) In this embodiment, a light-emitting device which is one embodiment of the present invention will be described.

[0163] The light-emitting device described in this embodiment mode is a micro-optical resonance device that utilizes the optical resonance effect between a pair of electrodes. As shown in Figure 4, the reflector has a microcavity structure and a pair of electrodes (reflection electrodes 4 The light emitting device has a structure having at least an EL layer 405 between the light emitting device 401 and the semi-transmissive / semi-reflective electrode 402. The EL layer 405 includes at least the light-emitting layer 4 which is a light-emitting region. 04 (404R, 404G, 404B), and other layers include a hole injection layer, a hole transport layer, an electron The light-emitting layer 404 may include a transport layer, an electron injection layer, a charge generation layer (E), etc. The organometallic complex according to one embodiment of the present invention is included.

[0164] In this embodiment, a light emitting element having a different structure (first light emitting element (R) 4) is used as shown in FIG. 10R, a second light-emitting element (G) 410G, and a third light-emitting element (B) 410B. A light emitting device to be used will be described.

[0165] The first light-emitting element (R) 410R includes a first transparent conductive layer 403a on a reflective electrode 401, The first light-emitting layer (B) 404B, the second light-emitting layer (G) 404G, and the third light-emitting layer (R) 404 The EL layer 405 partially containing R and the semi-transmissive / semi-reflective electrode 402 are laminated in this order. In addition, the second light emitting element (G) 410G has a second transparent conductive layer 4 on the reflective electrode 401. 03b, an EL layer 405, and a semi-transmissive / semi-reflective electrode 402 are laminated in this order. The third light emitting element (B) 410B has an EL layer 405 on a reflective electrode 401 and a semi-transmissive A semi-reflective electrode 402 is laminated in this order.

[0166] In addition, the light emitting elements (first light emitting element (R) 410R, second light emitting element (G) 410G In the third light-emitting element (B) 410B), a reflective electrode 401, an EL layer 405, a semi-transmissive layer The semi-reflective electrode 402 is shared. In the first light-emitting layer (B) 404B, Light with a peak in the wavelength region below 480 nm (λ B ) emits light, and the second light-emitting layer (G) In 404G, light with a peak in the wavelength range of 500 nm to 550 nm (λ G ) is issued The third light-emitting layer (R) 404R emits light in the wavelength range of 600 nm to 760 nm. Peak light (λ R ) emits light. This causes any of the light-emitting elements (the first light-emitting element (R) 410R, the second light-emitting element (G) 410G, and the third light-emitting element (B) 410B) , the first light-emitting layer (B) 404B, the second light-emitting layer (G) 404G, and the third light-emitting layer (R ) The light emitted from 404R is superimposed, that is, it emits broad light across the visible light range. From the above, the wavelength is λ B <λ G <λ R It is a relationship Let us assume that.

[0167] Each of the light-emitting elements shown in this embodiment has a reflective electrode 401 and a semi-transmissive / semi-reflective electrode 40 2 and an EL layer 405 is sandwiched between the EL layer 405 and the The light emitted from the layer in all directions functions as a micro-optical resonator (microcavity) The reflective electrode 401 and the semi-transmissive / semi-reflective electrode 402 are resonated. The electrode 401 is made of a conductive material having reflectivity, and the reflectance of visible light to the film is The rate is 40% to 100%, preferably 70% to 100%, and the resistivity is 1×10 -2 The semi-transmissive / semi-reflective electrode 402 has a reflectivity of Ωcm or less. The film is made of a conductive material and a conductive material having optical transparency, and the reflection of visible light on the film is The emissivity is 20% to 80%, preferably 40% to 70%, and the resistivity is 1×10 - 2 It is assumed that the film has a resistance of less than Ωcm.

[0168] In the present embodiment, each light emitting element is divided into a first light emitting element (R) 410R and a second light emitting element (R). The transparent conductive layers (first transparent conductive layer 403a, second transparent conductive layer 403b) provided on the element (G) 410G are By changing the thickness of the transparent conductive layer 403b), the reflective electrode 401 and the semi-transparent The optical distance between the over- and semi-reflective electrodes 402 is changed. The emitted broad light is distributed between the reflective electrode 401 and the semi-transmissive and semi-reflective electrode 402 as follows: Since it is possible to strengthen the light of resonating wavelengths and attenuate the light of non-resonating wavelengths, By changing the optical distance between the reflective electrode 401 and the semi-transmissive / semi-reflective electrode 402, different It is possible to extract light of a certain wavelength.

[0169] The optical distance (also called the optical path length) is the actual distance multiplied by the refractive index. In the embodiment, it is expressed by multiplying the actual film thickness by n (refractive index). Optical distance = actual film thickness x n.

[0170] In the first light emitting element (R) 410R, the reflective electrode 401 is connected to the semi-transmissive and semi-reflective electrode 402. Total thickness up to 02 m R / 2 (where m is a natural number), the second light-emitting element (G) 410G The total thickness from the reflective electrode 401 to the semi-transmissive and semi-reflective electrode 402 is mλ G / 2 (where m In the third light emitting element (B) 410B, a semi-transmissive / semi-reflective electrode is formed from the reflective electrode 401. Total thickness up to pole 402 mλ B / 2 (where m is a natural number).

[0171] From the above, the first light-emitting element (R) 410R is mainly composed of the first The light (λ R ) is taken out, and the second light-emitting element (G) 4 From 10G, light was emitted mainly from the second light-emitting layer (G) 404G included in the EL layer 405. Light (λ G ) is extracted, and from the third light-emitting element (B) 410B, mainly the EL layer 405 The light (λ ) emitted from the first light emitting layer (B) 404B included in B ) is extracted. Light extracted from the light emitting element is emitted from the semi-transmissive and semi-reflective electrode 402 side.

[0172] In the above configuration, the total thickness from the reflective electrode 401 to the semi-transmissive and semi-reflective electrode 402 is Strictly speaking, the reflection region of the reflective electrode 401 is reflected by the reflection region of the semi-transmissive and semi-reflective electrode 402. However, the reflective electrode 401 and the semi-transmissive / semi-reflective electrode 40 Since it is difficult to precisely determine the position of the reflective region in the semiconductor device 2, the reflective electrode 401 and the semiconductor device 301 are The above-mentioned effect can be obtained sufficiently by assuming that any position of the transmissive / semi-reflective electrode 402 is a reflective region. It is possible to do so.

[0173] Next, in the first light-emitting element (R) 410R, the reflective electrode 401 is connected to the third light-emitting layer (R )404R, the optical distance is set to the desired film thickness ((2m'+1)λ R / 4 (where m' is a natural number )) to amplify the light emission from the third light-emitting layer (R) 404R. The light emitted from the third light-emitting layer (R) 404R is reflected by the reflective electrode 401. The light that is reflected back (first reflected light) is semi-transmitted and semi-reflected by the third light-emitting layer (R) 404R. Since interference occurs with the light (first incident light) directly incident on the electrode 402, the reflective electrode 401 The optical distance to the third light-emitting layer (R) 404R is set to a desired value ((2m'+1)λ R / 4 (where , m' is a natural number), the phase difference between the first reflected light and the first incident light is In combination, the light emitted from the third light-emitting layer (R) 404R can be amplified.

[0174] Strictly speaking, the optical distance between the reflective electrode 401 and the third light-emitting layer (R) 404R is The optical distance between the reflection area of ​​the electrode 401 and the light-emitting area of ​​the third light-emitting layer (R) 404R is However, the reflection region of the reflective electrode 401 and the third light-emitting layer (R) Since it is difficult to precisely determine the position of the light-emitting region in the reflective electrode 40 Assume that an arbitrary position of the third light-emitting layer (R) 404R is the reflective region and an arbitrary position of the third light-emitting layer (R) 404R is the light-emitting region. This will enable the above-mentioned effects to be obtained sufficiently.

[0175] Next, in the second light-emitting element (G) 410G, the second light-emitting layer (G )404G optical distance to the desired film thickness ((2m''+1)λ G / 4 (where m'' is the By adjusting the temperature (T) of the second light-emitting layer (G) 404G to a value equal to the temperature (T), the light emission from the second light-emitting layer (G) 404G can be amplified. The light emitted from the second light-emitting layer (G) 404G is reflected by the reflective electrode 401. The reflected light (second reflected light) is reflected by the second light emitting layer (G) 404G as a semi-transparent or semi-transparent light. Since the light (second incident light) directly incident on the reflective electrode 402 interferes with the reflective electrode 401, to the second light-emitting layer (G) 404G to a desired value ((2m''+1)λG / 4( However, m'' is a natural number, so that the second reflected light and the second incident light By adjusting the phase with the second light-emitting layer (G) 404G, the light emitted from the second light-emitting layer (G) 404G can be amplified.

[0176] Strictly speaking, the optical distance between the reflective electrode 401 and the second light-emitting layer (G) 404G is The optical distance between the reflection area of ​​the electrode 401 and the light-emitting area of ​​the second light-emitting layer (G) 404G is However, the reflection region of the reflective electrode 401 and the second light-emitting layer (G) Since it is difficult to precisely determine the position of the light emitting region in the reflective electrode 40 Assume that an arbitrary position of the second light-emitting layer (G) 404G is the reflective region and an arbitrary position of the second light-emitting layer (G) 404G is the light-emitting region. This will enable the above-mentioned effects to be obtained sufficiently.

[0177] Next, in the third light-emitting element (B) 410B, the first light-emitting layer (B ) Set the optical distance to 404B at the desired thickness ((2m''+1)λ B / 4 (where m'' is a natural number), the light emission from the first light-emitting layer (B) 404B is amplified. The light emitted from the first light-emitting layer (B) 404B is reflected by the reflective electrode 401. The light reflected back by the first light-emitting layer (B) 404B is semi-transmitted. The light (third incident light) directly incident on the semi-reflective electrode 402 interferes with the light (third incident light) incident on the reflective electrode 4 The optical distance from the first light-emitting layer (B) 404B to the desired value ((2m'''+1)λ B / 4 (where m''' is a natural number), the third reflected light and the third The phase of the incident light can be adjusted to amplify the light emitted from the first light-emitting layer (B) 404B. can.

[0178] In the third light emitting element, the light between the reflective electrode 401 and the first light emitting layer (B) 404B is Strictly speaking, the optical distance is the distance between the reflective area of ​​the reflective electrode 401 and the first light-emitting layer (B) 404B. However, the reflectance of the reflective electrode 401 is different from that of the light emitting region. It is difficult to precisely determine the position of the light-emitting region in the first light-emitting layer (B) 404B. Therefore, any position of the reflective electrode 401 can be set as a reflective region, and any position of the first light-emitting layer (B) 404B can be set as a reflective region. It is assumed that the above-mentioned effect can be sufficiently obtained by assuming any desired position as the light emitting region.

[0179] In the above configuration, each of the light-emitting elements has a structure in which the EL layer has a plurality of light-emitting layers. However, the present invention is not limited to this. For example, the tank described in the fourth embodiment may be used. In combination with the structure of a DEM type light emitting device, a single light emitting device is sandwiched between charge generating layers to form multiple EL A single or multiple light-emitting layers may be formed in each EL layer.

[0180] The light-emitting device shown in this embodiment has a microcavity structure, and the same EL Even if the device has multiple layers, it is possible to extract light of different wavelengths from each light-emitting element, so RGB coating is possible. Therefore, it is easy to realize high resolution, and for this reason, This is advantageous in realizing color. In addition, it is possible to enhance the emission intensity of a specific wavelength in the front direction. This configuration allows for low power consumption by using pixels of three or more colors. This is particularly useful when applied to color displays (image display devices) using the same technology, but it is also useful in lighting and other applications. It may be used for any purpose.

[0181] (Embodiment 6) In this embodiment, a light-emitting element is provided in which the organometallic complex of one embodiment of the present invention is used for a light-emitting layer. A light emitting device that achieves this will be described.

[0182] The light emitting device may be a passive matrix light emitting device or an active matrix light emitting device. The light emitting device shown in this embodiment may be the light emitting device described in the other embodiment. A light emitting element can be applied.

[0183] In this embodiment mode, an active matrix light emitting device will be described with reference to FIG. .

[0184] 5(A) is a top view showing the light emitting device, and FIG. 5(B) is a top view showing the light emitting device along the dashed line A- 1 is a cross-sectional view taken along line A' of an active matrix light-emitting device according to the present embodiment. A pixel section 502 and a driving circuit section (source line driving circuit) 50 are provided on an element substrate 501. 3 and a driver circuit section (gate line driver circuit) 504 (504a and 504b). The pixel portion 502, the driver circuit portion 503, and the driver circuit portion 504 are sealed by a sealant 505. It is sealed between the element substrate 501 and a sealing substrate 506 .

[0185] In addition, on the element substrate 501, a driving circuit section 503 and a driving circuit section 504 are provided. Signals (e.g., video signals, clock signals, start signals, reset signals, etc.) and potentials A wiring 507 is provided for connecting an external input terminal for transmitting the signal. An example of providing an FPC (flexible printed circuit) 508 as an external input terminal is shown below. Although only the FPC is shown here, the FPC also has a printed wiring board. The light emitting device in this specification may include a light emitting device itself. This includes not only the body but also the state in which an FPC or PWB is attached to it.

[0186] Next, the cross-sectional structure will be described with reference to FIG. A driver circuit portion 503 which is a source line driver circuit is formed in the pixel portion. 5, a pixel portion 502 is shown.

[0187] The driving circuit section 503 is a combination of an n-channel TFT 509 and a p-channel TFT 510. The circuit forming the driver circuit section is shown in FIG. It may be formed of various CMOS circuits, PMOS circuits, or NMOS circuits. In the embodiment, a driver integrated type in which a driving circuit is formed on a substrate is shown, but this is not necessarily required. It is not necessary, and the driving circuit can be formed externally instead of on the substrate.

[0188] The pixel section 502 includes a switching TFT 511, a current control TFT 512, and a current A first TFT 512 electrically connected to the wiring (source electrode or drain electrode) of the control TFT 512 The first electrode (anode) 513 is formed of a plurality of pixels. An insulator 514 is formed covering the end of the substrate 13. Here, a positive photosensitive acrylic is used. It is formed by using a resin.

[0189] In order to improve the coverage of the film to be laminated on the upper layer, the upper end of the insulator 514 It is preferable that a curved surface having a curvature is formed at the upper or lower end. The material of the object 514 is either a negative photosensitive resin or a positive photosensitive resin. It can be used not only for organic compounds but also for inorganic compounds such as silicon oxide and silicon oxynitride. Both of these can be used.

[0190] An EL layer 515 and a second electrode (cathode) 516 are laminated on a first electrode (anode) 513. The EL layer 515 is provided with at least a light-emitting layer. The EL layer 515 includes an organic metal complex according to one embodiment of the present invention. A hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge generation layer, etc. may be appropriately provided on the substrate. can.

[0191] The total thickness of the first electrode (anode) 513, the EL layer 515, and the second electrode (cathode) 516 is The light-emitting element 517 is formed with a layer structure. The first electrode (anode) 513, the EL layer 515 The material used for the second electrode (cathode) 516 is the material shown in Embodiment 2. Although not shown here, the second electrode (cathode) 516 can be connected to an external input terminal The FPC 508 is electrically connected to the FPC 508.

[0192] In addition, although only one light-emitting element 517 is shown in the cross-sectional view shown in FIG. In the pixel section 502, a plurality of light emitting elements are arranged in a matrix. 02, a light-emitting element capable of emitting three types of light (R, G, B) is selectively formed, It is possible to form a light-emitting device capable of full color display. By combining these, a light emitting device capable of full color display may be obtained.

[0193] Furthermore, a sealing substrate 506 is bonded to the element substrate 501 with a sealing material 505. The light is emitted into a space 518 surrounded by the element substrate 501, the sealing substrate 506, and the sealant 505. The structure is provided with an element 517. The space 518 is filled with an inert gas (such as nitrogen, etc.). In addition to the case where the cavity is filled with a gas such as argon, the cavity may also be filled with a sealing material 505. .

[0194] It is preferable to use an epoxy resin for the sealing material 505. It is preferable that the sealing substrate 506 is made of a material that is as impermeable to moisture and oxygen as possible. In addition to glass and quartz substrates, FRP (Fiberglass-Reinforced Plastics) is also used as a material for unforced Plastics), PVF (Polyvinyl fluoride), Polyester Alternatively, a plastic substrate made of acrylic or the like can be used.

[0195] In this manner, an active matrix light emitting device can be obtained.

[0196] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiment modes. There can be.

[0197] (Embodiment 7) In this embodiment, a light-emitting device manufactured by using an organometallic complex which is one embodiment of the present invention will be described. Examples of various electronic devices completed using the above will be described with reference to FIGS. 6 and 7. FIG.

[0198] As an example of an electronic device to which a light-emitting device is applied, a television set (a television, (also called TV receivers), computer monitors, digital cameras, digital video digital cameras, digital photo frames, mobile phones (also called mobile phones or mobile phone devices), Examples include portable game machines, personal digital assistants, audio playback devices, and large game machines such as pachinko machines. Specific examples of these electronic devices are shown in Figure 6.

[0199] FIG. 6A shows an example of a television device. The television device 7100 includes: A display unit 7103 is built into the housing 7101. The display unit 7103 displays images. It is possible to use a light-emitting device in the display portion 7103. 7 shows a configuration in which a housing 7101 is supported by a stand 7105.

[0200] 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 using 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 be used to control the video. A display unit 7107 for displaying information output from the device 7110 may be provided.

[0201] The television device 7100 includes a receiver, a modem, and the like. It is possible to receive general television broadcasts, and furthermore to receive them by wired or wireless connection via a modem. By connecting to a communication network, it is possible to communicate in one direction (from sender to receiver) or two directions ( It is also possible to communicate information between a sender and a receiver, or between receivers themselves.

[0202] FIG. 6B shows a computer, which includes a main body 7201, a housing 7202, a display unit 7203, and a keyboard. keyboard 7204, external connection port 7205, pointing device 7206, etc. Note that the computer is manufactured by using a light-emitting device for the display portion 7203. .

[0203] FIG. 6C 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. A display unit 7305 is incorporated in the housing 7302. The portable gaming machine shown in FIG. 6(C) also includes a speaker unit 7306 and a recording medium insertion unit 7307. , LED lamp 7308, input means (operation keys 7309, connection terminal 7310, sensor 73 11 (force, displacement, position, velocity, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical Chemical substances, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration , odor or infrared measuring function), microphone 7312) etc. Of course, the configuration of the portable gaming machine is not limited to the above, and at least the display unit 73 04 and the display portion 7305, or either one of them may use a light-emitting device. The portable gaming machine shown in FIG. The function of reading out the programs or data recorded on the media and displaying them on the display unit, and other It has a function to share information with the portable game machine by wireless communication. The functions of the portable gaming machine are not limited to these, and the portable gaming machine may have a variety of functions.

[0204] FIG. 6D shows an example of a mobile phone. A mobile phone 7400 includes a housing 7401. In addition to the display unit 7402, operation buttons 7403, an external connection port 7404, The mobile phone 7400 is equipped with a speaker 7405, a microphone 7406, and the like. The device is used for the display portion 7402 .

[0205] In a mobile phone 7400 shown in FIG. 6D, information can be displayed by touching a display portion 7402 with a finger or the like. You can also make calls, write emails, and perform other operations. This can be done by touching the display portion 7402 with a finger or the like.

[0206] The screen of the display unit 7402 has three main modes. The first is a mode that mainly displays 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.

[0207] For example, when making a call or composing an e-mail, the display unit 7402 is used for inputting characters. The main input mode is the character input mode, and the input operation of the characters displayed on the screen can be performed. In this case, it is preferable to display a keyboard or number buttons on most of the screen of the display portion 7402. I wish.

[0208] In addition, a sensor for detecting tilt, such as a gyro or an acceleration sensor, is installed inside the mobile phone 7400. By providing a detection device having the above, the orientation of the mobile phone 7400 (portrait or landscape) can be determined, The screen display on the display portion 7402 can be automatically switched.

[0209] The screen mode can be changed by touching the display portion 7402 or by operating the housing 7401. The type of image displayed on the display unit 7402 can be selected by operating the operation button 7403. For example, the image signal to be displayed on the display unit may be changed by If the data is text data, the mode switches to input mode.

[0210] In the input mode, a signal detected by the optical sensor of the display unit 7402 is detected, and the display If there is no input by touch operation on the display unit 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 display mode to the display mode.

[0211] The display unit 7402 can also function as an image sensor. By touching 402 with a palm or a finger and capturing an image of a palm print, fingerprint, or the like, personal authentication can be performed. In addition, a backlight that emits near-infrared light to the display unit or a sensing light that emits near-infrared light By using a source, it is also possible to image finger veins, palm veins, etc.

[0212] Figures 7(A) and 7(B) show tablet terminals that can be folded in half. Figure 7(A) shows In the open state, the tablet terminal includes a housing 9630, a display unit 9631a, and a display unit 96 31b, a display mode changeover switch 9034, a power switch 9035, a power saving mode changeover switch The switch 9036, the fastener 9033, and the operation switch 9038 are included. The tablet terminal has a light emitting device in one or both of the display portions 9631a and 9631b. It is produced by using

[0213] A part of the display unit 9631a can be used as a touch panel area 9632a. By touching the operation keys 9637 displayed on the display unit 96, data can be input. In 31a, as an example, half of the area has a display function only, and the other half The display unit 96 has a touch panel function, but is not limited to this. The entire area of ​​the display unit 931a may have a touch panel function. The entire surface of 631a is used as a touch panel by displaying keyboard buttons, and the display part 9631b is It can be used as a display screen.

[0214] In addition, in the display unit 9631b, as in the display unit 9631a, The part of the touch panel can be the area 9632b of the touch panel. Touch the area where the mode display switch button 9639 is displayed with your finger or a stylus. A keyboard button can be displayed on the display portion 9631b.

[0215] In addition, the touch panel area 9632a and the touch panel area 9632b are simultaneously You can also use touch input.

[0216] A display mode changeover switch 9034 is used to change the display orientation, such as portrait or landscape. You can switch between black and white and color display. The switch 9036 is a switch that turns on and off when the tablet terminal is in use and is detected by a light sensor built into the tablet terminal. The brightness of the display can be optimized according to the amount of light. In addition to sensors, other detection devices such as gyros, acceleration sensors, etc. that detect tilt may be incorporated.

[0217] FIG. 7A shows an example in which the display area of ​​the display portion 9631b is the same as that of the display portion 9631a. However, there is no particular limitation, and one size may be different from the other size. For example, one display panel may have a higher resolution than the other. It is also possible to use the following.

[0218] FIG. 7B shows the tablet terminal in a closed state. The tablet terminal includes a housing 9630 and a solar cell 96 33, a charge / discharge control circuit 9634, a battery 9635, and a DCDC converter 9636 In addition, in FIG. 7B, a battery 9635 is used as an example of the charge and discharge control circuit 9634. A configuration having a DC-DC converter 9636 is shown.

[0219] In addition, since the tablet device can be folded in half, the case 9630 can be folded when not in use. Therefore, the display portions 9631a and 9631b can be protected. This makes it possible to provide a tablet device that is highly durable and reliable even when used for a long period of time.

[0220] In addition, the tablet terminals shown in Figs. 7(A) and 7(B) can display various information. Functions that display (still images, videos, text images, etc.), calendars, dates, or times, etc. A function to display information on the display unit, and a touch input function to operate or edit information displayed on the display unit Functions such as the ability to control processing using various software (programs) can be done.

[0221] The solar cell 9633 attached to the surface of the tablet device supplies power to the touch panel. The solar cell 9633 can supply the light to a display unit, a video signal processor, or the like. The battery 9635 is provided on one or both sides of the housing 9630 and is used for charging the battery 9635 that supplies power. This is preferable because it can be configured to perform the above-mentioned operations. The use of lithium-ion batteries has the advantage of enabling miniaturization.

[0222] The configuration and operation of the charge / discharge control circuit 9634 shown in FIG. A block diagram is shown and explained in FIG. 7(C). , DC-DC converter 9636, converter 9638, switches SW1 to SW3, display The figure shows the part 9631, the battery 9635, the DCDC converter 9636, The inverter 9638 and the switches SW1 to SW3 are connected to the charge / discharge control circuit 96 shown in FIG. This corresponds to 34.

[0223] First, an example of operation in which power is generated by the solar cell 9633 using external light will be described. The power generated by the solar cell 9633 becomes the voltage for charging the battery 9635. The voltage is increased or decreased by the DC-DC converter 9636. When power is used from the Solar Cell 9633, switch SW1 is turned on and the The inverter 9638 increases or decreases the voltage to the voltage required for the display unit 9631. When the display unit 9631 is not to be displayed, the switch SW1 is turned off and the switch S The configuration may be such that W2 is turned on to charge the battery 9635.

[0224] The solar cell 9633 is shown as an example of a power generating means, but is not limited thereto. Other power generation methods such as piezoelectric elements and thermoelectric conversion elements (Peltier elements) For example, the battery 9635 may be charged. A non-contact power transmission module that receives and charges, or a structure that combines other charging methods It may also be composed of.

[0225] In addition, if the display unit described in this embodiment is provided, the electronic device shown in FIG. It goes without saying that there is no limitation.

[0226] In the above manner, an electronic device can be obtained by using the light-emitting device which is one embodiment of the present invention. The range of applications for light-emitting devices is extremely wide, and they can be used in electronic devices in a wide range of fields. It is.

[0227] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiments. There can be.

[0228] (Embodiment 8) In this embodiment, a lighting device including a light-emitting device including an organometallic complex according to one embodiment of the present invention is used. An example of the device will be described with reference to FIG.

[0229] FIG. 8 shows an example in which the light emitting device is used as an indoor lighting device 8001. It is also possible to make the surface area larger, so a large-area lighting device can be formed. By using a housing having such a structure, it is possible to form a lighting device 8002 having a curved light-emitting area. The light-emitting element included in the light-emitting device shown in this embodiment mode has a thin film shape, and the design of the housing can be changed. Therefore, lighting devices with various elaborate designs can be created. Furthermore, a large lighting device 8003 may be provided on the wall of the room.

[0230] In addition, by using a light-emitting device on the surface of a table, a lighting device that also functions as a table can be provided. The lighting device 8004 can be used as a lighting device. This makes it possible to provide a lighting device that also functions as furniture.

[0231] As described above, various lighting devices using the light-emitting device can be obtained. The device is considered to be included in one aspect of the present invention.

[0232] The structure described in this embodiment may be used in appropriate combination with structures described in other embodiments. There can be. EXAMPLES

[0233] <Synthesis Example 1> In this example, an organic compound represented by the structural formula (100) of the embodiment 1 according to the present invention is Metal complex, bis{4,6-dimethyl-2-[3-(3,5-dimethylphenyl)-5-phenyl phenyl-2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl-3,5-hepta ndionate-κ 2 O,O') Iridium(III) (abbreviation: [Ir(dmdppr-P) 2 The synthesis method of [Ir(dmdppr-P) 2 The structure of (dibm)] (abbreviation) is shown below.

[0234] [ka]

[0235] <Step 1: 2,3-bis(3,5-dimethylphenyl)pyrazine (abbreviation: Hdmdp Synthesis of pr) First, 5.00 g of 2,3-dichloropyrazine and 10 g of 3,5-dimethylphenylboronic acid were .23g, sodium carbonate 7.19g, bis(triphenylphosphine)palladium(I I) dichloride (abbreviation: Pd(PPh 3 ) 2 Cl 2 ) 0.29g, water 20mL, acetonite 20 mL of trifluoromethane was placed in a recovery flask equipped with a reflux condenser, and the inside of the flask was replaced with argon. The reaction vessel was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. Here, 2.55 g of 3,5-dimethylphenylboronic acid and 1.80 g of sodium carbonate are added. , Pd(PPh 3 ) 2 Cl 2 0.070g, 5 mL of water, and 5 mL of acetonitrile in a flask. Then, heat it again with microwaves (2.45GHz, 100W) for 60 minutes. did.

[0236] Thereafter, water was added to this solution, and the organic layer was extracted with dichloromethane. The mixture was washed with saturated aqueous sodium bicarbonate solution, 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 hexane. Flash column chromatography was performed using xanthene:ethyl acetate = 5:1 (volume ratio) as the developing solvent. The solvent was removed, and the resulting solid was purified by filtration using a 10:1 mixture of dichloromethane and ethyl acetate. The product was purified by flash column chromatography using 100% (volume ratio) of 1 as a developing solvent. The pyrazine derivative Hdmdppr (abbreviation) was obtained (white powder, 44% yield). The microwave irradiation was performed using a microwave synthesis device (Discover, manufactured by CEM). The synthesis scheme of compound 1 is shown in (a-1) below.

[0237] [ka]

[0238] <Step 2: 2,3-bis(3,5-dimethylphenyl)-5-phenylpyrazine (abbreviation Synthesis of Hdmdppr-P) First, 4.28 g of Hdmdppr (abbreviation) obtained in step 1 above and 80 ml of dry THF L was placed in a three-neck flask and the inside was replaced with nitrogen. After cooling the flask on ice, phenyllithium ( 9.5 mL of 1.9 M butyl ether solution was added dropwise and the mixture was stirred at room temperature for 23.5 hours. The liquid was poured into water and extracted with chloroform. The obtained organic layer was washed with water and saturated saline, and The mixture was dried over magnesium oxide, and manganese oxide was added to the resulting mixture, which was then stirred for 30 minutes. The solution was then filtered and the solvent was removed by distillation. The resulting residue was mixed with dichloromethane as a developing solvent. The desired pyrazine derivative, Hdmdppr, was obtained by purifying the compound using silica gel column chromatography. The synthesis scheme of step 2 is shown below (a -2).

[0239] [ka]

[0240] <Step 3: Di-μ-chloro-tetrakis{4,6-dimethyl-2-[3-(3,5- Dimethylphenyl)-5-phenyl-2-pyrazinyl-κN]phenyl-κC}diylidin Ir(dmdppr-P) 2 Cl] 2 Synthesis of Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the Hdmdp obtained in step 2 above were pr-P (abbreviation) 1.40 g, iridium chloride hydrate (IrCl 3 H 2 O)(Sigm Put 0.51 g of a-Aldrich into a recovery flask equipped with a reflux condenser, and The inside was replaced with argon. After that, microwaves (2.45 GHz, 100 W) were irradiated for 1 hour. After the solvent was removed by distillation, the resulting residue was suction filtered and washed with ethanol. Nuclear complex [Ir(dmdppr-P)2 Cl] 2 (abbreviation) was obtained (reddish brown powder, yield 58%) The synthetic scheme for step 3 is shown below in (a-3).

[0241] [ka]

[0242] <Step 4: Bis{4,6-dimethyl-2-[3-(3,5-dimethylphenyl)-5 -phenyl-2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl-3,5-phenyl Butanedionate-κ 2 O,O')iridium(III) (abbreviation: [Ir(dmdppr- P) 2 Synthesis of (dibm)]) In addition, 30 mL of 2-ethoxyethanol and the binuclear complex [Ir(d mdppr-P) 2 Cl] 2 0.94g, diisobutyrylmethane (abbreviation: Hdibm) 0.23g of sodium chloride and 0.52g of sodium carbonate were placed in a recovery flask equipped with a reflux condenser. The inside of the container was replaced with argon. Then, microwaves (2.45 GHz, 120 W) were used for 60 minutes. The solvent was removed, and the resulting residue was filtered with ethanol. The solid was washed with water and ethanol, and then recrystallized in a mixed solvent of dichloromethane and ethanol. By crystallizing the organometallic complex [Ir(dmdppr-P) 2 ( The compound (abbreviation: dibm) was obtained as a dark red powder (yield: 75%). The model is shown in (a-4) below.

[0243] [ka]

[0244] The dark red powder obtained by the above synthesis method was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in FIG. In Example 1, an organometallic complex according to one embodiment of the present invention is represented by the above structural formula (100). [Ir(dmdppr-P) 2 (dibm)] (abbreviation) was obtained.

[0245] 1 H-NMR.δ(CDCl 3 ):0.79(d,6H),0.96(d,6H),1 .41(s,6H),1.96(s,6H),2.24-2.28(m,2H),2.4 1(s,12H),5.08(s,1H),6.46(s,2H),6.82(s,2H ),7.18(s,2H),7.39-7.50(m,10H),8.03(d,4H) ,8.76(s,2H).

[0246] Next, [Ir(dmdppr-P) 2 (dibm)] (abbreviation) in dichloromethane The ultraviolet-visible absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and the emission spectrum The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V55 manufactured by JASCO Corporation). A dichloromethane solution (0.062 mmol / L) was placed in a quartz cell and heated at room temperature. The emission spectrum was measured using a fluorometer (Hamamatsu Photonics, Inc.). A degassed dichloromethane solution (0.010 mmol / L) was added to the The samples were placed in an English cell and measurements were performed at room temperature. The results are shown in FIG. 10. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and the emission intensity. 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 10 is a dichloromethane solution (0. 0.062mmol / L) in a quartz cell and the absorption spectrum was measured. The absorption spectrum measured by placing only the sample in a quartz cell was subtracted from the results shown.

[0247] As shown in FIG. 10, the organometallic complex [Ir(dmdppr-P) 2 (dibm)] (abbreviation) has an emission peak at around 640 nm and is dichloromethane Red-orange luminescence was observed from the solution.

[0248] Furthermore, the obtained [Ir(dmdppr-P) 2 (dibm)] (abbreviation) weight loss rate A high vacuum differential thermobalance (TG-DTA24 manufactured by Bruker AXS Co., Ltd.) was used. 10SA). Vacuum degree 1×10 -3 Pa, heating rate 10℃ / min As shown in FIG. 37, the organometallic complex [Ir (dmdppr-P) 2 (dibm)] (abbreviation) means that the weight loss rate is 100%, which is good. For comparison, the compound without dimethyl groups at the 3- and 5-positions was The weight loss rate of compound A is 78%. A certain organometallic complex has improved sublimability by having dimethyl groups at the 3- and 5-positions. It was found that... EXAMPLES

[0249] <Synthesis Example 2> In this example, an organic compound represented by structural formula (107) in Embodiment 1 according to one embodiment of the present invention is Metal complex, bis{2-[6-(3,5-dimethylphenyl)-4-pyrimidinyl-κN3 ]-4,6-Dimethylphenyl-κC}(2,6-dimethyl-3,5-heptanedionate -κ 2 O,O') Iridium(III) (abbreviation: [Ir(dmdppm) 2 (dibm) The synthesis method of [Ir(dmdppm) 2 (dibm)](abbreviated) The structure of this compound (called

[0250] [ka]

[0251] <Step 1: 4,6-bis(3,5-dimethylphenyl)pyrimidine (abbreviation: Hdmd ppm) synthesis> First, 5.97 g of 4,6-dichloropyrimidine and 1 g of 3,5-dimethylphenylboronic acid were 2.04g, sodium carbonate 8.48g, bis(triphenylphosphine)palladium ( II) dichloride (abbreviation: Pd(PPh 3 ) 2 Cl 2 )0.34g, water 20mL, 1,3 -Dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidinone (abbreviation: DMPU 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 container was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. In addition, 2.58 g of 3,5-dimethylphenylboronic acid, 1.78 g of sodium carbonate, d(PPh 3 ) 2 Cl 2Put 0.070g, 5mL of water, and 5mL of DMPU into a flask. The mixture was heated again by irradiation with microwaves (2.45 GHz, 100 W) for 60 minutes.

[0252] The resulting residue was then suction filtered with water and washed with water and ethanol. Dissolve in dichloromethane and pass through a filter aid consisting of layers of Celite, alumina, and Celite. The pyrimidine derivative Hdmdp was isolated by filtration and washing with ethanol. pm was obtained (white powder, yield 56%). Note that microwave irradiation was performed using a microwave synthesis apparatus ( The synthesis scheme for step 1 is shown below (b-1). As shown in.

[0253] [ka]

[0254] <Step 2: Di-μ-chloro-tetrakis{2-[6-(3,5-dimethylphenyl) -4-pyrimidinyl-κN3]-4,6-dimethylphenyl-κC}diiridium(II I) (Abbreviation: [Ir(dmdppm) 2 Cl] 2 Synthesis of Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the Hdmdp obtained in step 1 above were pm (abbreviation) 2.10 g, iridium chloride hydrate (IrCl 3 H 2 O) (Sigma- Put 1.07 g of ... The atmosphere was replaced with argon. After that, microwaves (2.45 GHz, 100 W) were irradiated for 1 hour. After the solvent was distilled off, the resulting residue was suction filtered and washed with ethanol to obtain a binuclear complex. Body [Ir(dmdppm) 2Cl] 2 (abbreviation) was obtained (reddish brown powder, 74% yield). The synthesis scheme of trip 2 is shown below in (b-2).

[0255] [ka]

[0256] <Step 3: Bis{2-[6-(3,5-dimethylphenyl)-4-pyrimidinyl-κ N3]-4,6-dimethylphenyl-κC}(2,6-dimethyl-3,5-heptanediol Nat-κ 2 O,O') Iridium(III) (abbreviation: [Ir(dmdppm) 2 (dib m) Synthesis In addition, 30 mL of 2-ethoxyethanol and the binuclear complex [Ir(d mdppm) 2 Cl] 2 (abbreviation) 1.09g, diisobutyrylmethane (abbreviation: Hdibm 0.32 g of sodium carbonate and 0.72 g of sodium carbonate were placed in a recovery flask equipped with a reflux condenser. The inside of the scope was replaced with argon. Then, microwaves (2.45 GHz, 120 W) were used for 60 minutes. The mixture was heated by irradiating with light for 1 hour. The solvent was removed by distillation, and the resulting residue was subjected to suction filtration with ethanol. The obtained solid was washed with water and ethanol, and then reconstituted with a mixed solvent of dichloromethane and ethanol. By crystallizing, the organometallic complex [Ir(dmdppm) 2 (d The compound (abbreviation) was obtained as a red powder (yield 62%). The synthesis scheme for step 3 is as follows: Shown below in (b-3).

[0257] [ka]

[0258] The red powder obtained by the above synthesis method was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 11. In this Synthesis Example 2, the organometallic compound represented by the above structural formula (107) according to one embodiment of the present invention is Complex [Ir(dmdppm) 2 (dibm)] (abbreviation) was obtained.

[0259] 1 H-NMR.δ(CDCl 3 ):0.69(d,6H),0.82(d,6H),1 .51(s,6H),2.17-2.23(m,2H),2.31(s,6H),2.4 5(s,12H),5.19(s,1H),6.61(s,2H),7.17(s,2H ),7.56(s,2H),7.82(s,4H),8.11(d,2H),8.88( d,2H).

[0260] Next, [Ir(dmdppm) 2 (dibm)] (abbreviation) in dichloromethane Visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured. The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V550, manufactured by JASCO Corporation). ) was used, and a dichloromethane solution (0.072 mmol / L) was placed in a quartz cell and measured at room temperature. The emission spectrum was measured using a fluorescence spectrometer (Hamamatsu Photonics, Ltd.). A degassed dichloromethane solution (0.072 mmol / L) was placed on a quartz crystal. The absorption and emission spectra were measured at room temperature. This is shown in FIG. 12. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity. Two solid lines are shown for each sample. The thin solid line shows the absorption spectrum, and the thick solid line shows the emission spectrum. The absorption spectrum shown in FIG. 12 is a dichloromethane solution (0.07 2mmol / L) in a quartz cell and the absorption spectrum was measured. The absorption spectrum measured by inserting the sample in a quartz cell was subtracted from the result shown in FIG.

[0261] As shown in FIG. 12, the organometallic complex [Ir(dmdppm) 2 (d ibm)] (abbreviation) has an emission peak at around 609 nm, and in dichloromethane solution A reddish-orange emission was observed. EXAMPLES

[0262] <Synthesis Example 3> In this example, an organic compound represented by the structural formula (108) of Embodiment 1 according to one embodiment of the present invention is Metal complex, bis{2-[6-(3,5-dimethylphenyl)-4-pyrimidinyl-κN3 ]-4,6-dimethylphenyl-κC}(2,2',6,6'-tetramethyl-3,5- Heptanedionate-κ 2 O,O')iridium(III) (abbreviation: [Ir(dmdppm ) 2 The synthesis method of [Ir(dmdppm)] is explained below. 2 (d The structure of α-pyridinediaminetetraacetate (abbreviation):

[0263] [ka]

[0264] <Step 1: 4,6-bis(3,5-dimethylphenyl)pyrimidine (abbreviation: Hdmd ppm) synthesis> First, 5.97 g of 4,6-dichloropyrimidine and 1 g of 3,5-dimethylphenylboronic acid were 2.04g, sodium carbonate 8.48g, bis(triphenylphosphine)palladium ( II) dichloride (abbreviation: Pd(PPh 3 ) 2 Cl 2 )0.34g, water 20mL, 1,3 -Dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidinone (abbreviation: DMPU 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 container was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. In addition, 2.58 g of 3,5-dimethylphenylboronic acid, 1.78 g of sodium carbonate, d(PPh 3 ) 2 Cl 2 Put 0.070g, 5mL of water, and 5mL of DMPU into a flask. The mixture was heated again by irradiation with microwaves (2.45 GHz, 100 W) for 60 minutes.

[0265] The resulting residue was then suction filtered with water and washed with water and ethanol. Dissolve in dichloromethane and pass through a filter aid consisting of layers of Celite, alumina, and Celite. The pyrimidine derivative Hdmdp was isolated by filtration and washing with ethanol. pm (abbreviation) was obtained (white powder, 56% yield). The synthesis scheme for step 1 is shown below. As shown in c-1).

[0266] [ka]

[0267] <Step 2: Di-μ-chloro-tetrakis{2-[6-(3,5-dimethylphenyl) -4-pyrimidinyl-κN3]-4,6-dimethylphenyl-κC}diiridium(II I) (Abbreviation: [Ir(dmdppm) 2 Cl] 2 Synthesis of Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the Hdmdp obtained in step 1 above were pm (abbreviation) 2.10 g, iridium chloride hydrate (IrCl 3 H 2 O) (Sigma- Put 1.07 g of ... The atmosphere was replaced with argon. After that, microwaves (2.45 GHz, 100 W) were irradiated for 1 hour. After the solvent was distilled off, the resulting residue was suction filtered and washed with ethanol to obtain a binuclear complex. Body [Ir(dmdppm) 2 Cl] 2 (abbreviation) was obtained (reddish brown powder, 74% yield). The synthetic scheme of trip 2 is shown below in (c-2).

[0268] [ka]

[0269] <Step 3: Bis{2-[6-(3,5-dimethylphenyl)-4-pyrimidinyl-κ N3]-4,6-dimethylphenyl-κC}(2,2',6,6'-tetramethyl-3, 5-Heptanedionate-κ 2 O,O')iridium(III) (abbreviation: [Ir(dmdp pm) 2 Synthesis of (dpm)] In addition, 30 mL of 2-ethoxyethanol and the binuclear complex [Ir(d mdppm) 2 Cl] 2(abbreviation) 1.08g, dipivaloylmethane (abbreviation: Hdpm) 0 Put 0.37g of water and 0.71g of sodium carbonate into a round-bottom flask equipped with a reflux condenser. The inside of the container was replaced with argon. After that, it was irradiated with microwaves (2.45 GHz, 120 W) for 60 minutes. The solvent was removed by distillation, and the resulting residue was suction filtered with ethanol. The solid was washed with water and ethanol. The solid was dissolved in dichloromethane and added to the ceramic. After filtering through a filter aid consisting of a layer of ethyl acetate, alumina, and celite, dichloromethane was added. The organometallic complex according to one embodiment of the present invention is obtained by recrystallization from a mixed solvent of ethanol and ethyl acetate. [Ir(dmdppm) 2 (dpm)] (abbreviation) was obtained as a red powder (yield 21%). The synthetic scheme for step 3 is shown below in (c-3).

[0270] [ka]

[0271] The red powder obtained by the above synthesis method was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 13. In this Synthesis Example 3, the organometallic compound represented by the above structural formula (108) according to one embodiment of the present invention is Complex [Ir(dmdppm) 2 (dpm)] (abbreviation) was obtained.

[0272] 1 H-NMR.δ(CDCl 3 ):0.84(s,18H),1.51(s,6H), 2.31(s,6H),2.45(s,12H),5.52(s,1H),6.60(s ,2H),7.17(s,2H),7.55(s,2H),7.81(s,4H),8. 10(s,2H),8.84(d,2H).

[0273] Next, [Ir(dmdppm) 2 (dpm)] (abbreviation) in dichloromethane The visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and the emission spectrum are measured. The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V550, manufactured by JASCO Corporation). A dichloromethane solution (0.070mmol / L) was placed in a quartz cell and measured at room temperature. The emission spectrum was measured using a fluorometer (Hamamatsu Photonics F S920), a degassed dichloromethane solution (0.070 mmol / L) was placed in a quartz cell. The absorption and emission spectra were measured at room temperature. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and the emission intensity. Two solid lines are shown, the thin one showing the absorption spectrum and the thick one showing the emission spectrum. The absorption spectrum shown in Figure 14 is a dichloromethane solution (0.070 The absorption spectrum of dichloromethane alone was measured using a quartz cell containing 1 mmol / L of The results shown are those obtained by subtracting the absorption spectrum measured in a quartz cell.

[0274] As shown in FIG. 14, the organometallic complex [Ir(dmdppm) 2 ( dpm)] (abbreviation) has an emission peak at around 615 nm and is dissolved in dichloromethane. A reddish-orange emission was observed. EXAMPLES

[0275] In this example, an organometallic complex [Ir(dmdppr-P) 2 (d ibm)] (abbreviation) (structural formula (100)) is used in the light-emitting layer. The chemical formulas of the materials used in this embodiment are shown below.

[0276] [ka]

[0277] <Fabrication of light-emitting element 1> First, indium tin oxide containing silicon oxide (ITSO) is deposited on a glass substrate 1100. A film was formed by sputtering to form a first electrode 1101 that functions as an anode. The film thickness was 110 nm, and the electrode area was 2 mm x 2 mm.

[0278] Next, as a pretreatment for forming a light emitting element on the substrate 1100, the substrate surface is washed with water. After baking at 200°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0279] Then, 10 -4 The substrate 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 the deposition apparatus, the substrate 1100 is It was left to cool for about 30 minutes.

[0280] Next, the substrate 1100 is vacuum-steamed so that the surface on which the first electrode 1101 is formed faces downward. In this example, the EL layer 1 was formed by vacuum deposition. 102 comprises a hole injection layer 1111, a hole transport layer 1112, a light emitting layer 1113, and an electron transport A case where the layer 1114 and the electron injection layer 1115 are formed in this order will be described.

[0281] 10 minutes inside the vacuum chamber -4 After depressurizing to 100 Pa, 1,3,5-tri(dibenzothiophene-4 -yl)-benzene (abbreviation: DBT3P-II) and molybdenum(VI) oxide were 3P-II (abbreviation): molybdenum oxide = 4:2 (mass ratio) Thus, a hole injection layer 1111 was formed on the first electrode 1101. The film thickness was set to 40 nm. Co-evaporation is a method of simultaneously evaporating multiple different substances from different evaporation sources. It is law.

[0282] Next, 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine A hole transport layer 1112 is formed by depositing 20 nm of BPAFLP. Ta.

[0283] Next, the light-emitting layer 1113 was formed on the hole-transporting layer 1112. 2mDBTPD Bq-II), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl NPB, bis{4,6-dimethyl-2-[3-(3,5-dimethylphenyl )-5-Phenyl-2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl-3, 5-Heptanedionate-κ 2 O,O')iridium(III) (abbreviation: [Ir(dmdp pr-P) 2 (dibm)]) and 2mDBTPDBq-II (abbreviation):NPB (abbreviation) :[Ir(dmdppr-P) 2 (dibm)](abbreviation)=0.8:0.2:0.05( The thickness of the film was 40 nm.

[0284] Next, 2mDBTPDBq-II (abbreviation) was applied to the light-emitting layer 1113 at a thickness of 10 nm. By sequentially depositing 20 nm of benzophenone (abbreviation: Bphen), a laminated structure was formed. Further, lithium fluoride was deposited on the electron transport layer 1114. An electron injection layer 1115 was formed by vapor deposition.

[0285] Finally, aluminum was evaporated onto the electron injection layer 1115 to a thickness of 200 nm. Then, a second electrode 1103 serving as a cathode was formed, and a light-emitting element 1 was obtained. In all depositions, a resistance heating method was used.

[0286] The element structure of the thus obtained Light-emitting Element 1 is shown in Table 1.

[0287] [Table 1]

[0288] The fabricated light-emitting element 1 was placed in a glove box with a nitrogen atmosphere to prevent it from being exposed to the air. (Sealing material was applied around the element, and heat treatment was performed at 80°C for 1 hour during sealing.) ).

[0289] <Operation characteristics of light-emitting element 1> The operating characteristics of the fabricated light-emitting element 1 were measured. The measurements were performed at room temperature (25° C.). The atmosphere was very friendly.

[0290] First, the current density-luminance characteristics of the light-emitting element 1 are shown in FIG. is the luminance (cd / m 2 ), the horizontal axis is the current density (mA / cm 2 ) is shown. The voltage-luminance characteristics are shown in FIG. 17. In FIG. 17, the vertical axis represents luminance (cd / m 2 ), The horizontal axis represents voltage (V). The luminance vs. current efficiency characteristics of the light-emitting element 1 are shown in FIG. In FIG. 18, the vertical axis represents current efficiency (cd / A) and the horizontal axis represents luminance (cd / m 2 ) Furthermore, the voltage-current characteristics of the light-emitting element 1 are shown in FIG. indicates current (mA), and the horizontal axis indicates voltage (V).

[0291] As shown in FIG. 18, the organometallic complex [Ir(dmdppr-P) 2 (di It has been found that the light-emitting element 1, which uses the fluorine-containing ... Also, 1000cd / m 2 The main initial characteristics of the light-emitting element in the vicinity are shown in Table 2 below. show.

[0292] [Table 2]

[0293] From the above results, it can be seen that the light-emitting element 1 fabricated in this example has high luminance and shows good current efficiency. Furthermore, it is clear that the color purity is good, and that the red light emission is excellent. Light.

[0294] In addition, the light-emitting element 1 is rated at 2.5 mA / cm 2 Emission spectrum when a current is applied at a current density of As shown in FIG. 20, the emission spectrum of the light-emitting element 1 is around 640 nm. The organometallic complex [Ir(dmdppr-P) 2 (dibm)](abbreviation 20 shows the light emission from the organometallic complex of the light-emitting element 1. Body [Ir(dmdppr-P) 2 (dibm)] (abbreviation) instead of organometallic complex [Ir (tppr) 2 (dpm)] (abbreviation) was used to prepare comparative light-emitting element 1. The emission spectrum of the light-emitting element 1 is also shown as a comparative example. It was confirmed that the half-width of the organic metal EL element was narrower than that of the comparative light-emitting element 1. Complexes [Ir(dmdppr-P) 2 (dibm)] (abbreviation) in the structure of iridium The structure has a methyl group substituted at the 2- and 4-positions of the phenyl group bonded to the Therefore, the light-emitting element 1 is a light-emitting element with good luminous efficiency and good color purity. It can be said that he is a child.

[0295] A reliability test was also conducted on the light-emitting element 1. The results of the reliability test are shown in FIG. In FIG. 21, the vertical axis represents normalized luminance (%) when the initial luminance is 100%. The horizontal axis indicates the driving time (h) of the element. d / m 2 The light-emitting element 1 was driven under a constant current density condition. The luminance of 1 after 100 hours was approximately 68% of the initial luminance. The vertical axis shows the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis shows the normalized luminance (%) when the element is driven. The reliability test was performed by setting the current value to 0.3 mA and driving the light-emitting element 1. As a result, the luminance of the light-emitting element 1 after 100 hours was approximately 90% of the initial luminance. was.

[0296] Therefore, the light-emitting element 1 exhibits high reliability under any of the reliability tests performed under any conditions. In addition, by using the organometallic complex of one embodiment of the present invention for a light-emitting element, It was found that a light-emitting element with a long life could be obtained. EXAMPLES

[0297] In this example, an organometallic complex [Ir(dmdppm) 2 (dib A light-emitting element 2 using the compound (structural formula (107)) in the light-emitting layer will be described. In the description of the light-emitting element 2 in this embodiment, reference is made to FIG. 1 which is used to explain the light-emitting element 1 in the fourth embodiment. 5 is used. The chemical formulas of the materials used in this example are shown below.

[0298] [ka]

[0299] <Fabrication of light-emitting element 2> First, indium tin oxide containing silicon oxide (ITSO) is deposited on a glass substrate 1100. A film was formed by sputtering to form a first electrode 1101 that functions as an anode. The film thickness was 110 nm, and the electrode area was 2 mm x 2 mm.

[0300] Next, as a pretreatment for forming a light emitting element on the substrate 1100, the substrate surface is washed with water. After baking at 200°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0301] Then, 10 -4 The substrate 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 the deposition apparatus, the substrate 1100 is It was left to cool for about 30 minutes.

[0302] Next, the substrate 1100 is vacuum-steamed so that the surface on which the first electrode 1101 is formed faces downward. In this example, the EL layer 1 was formed by vacuum deposition. 102 comprises a hole injection layer 1111, a hole transport layer 1112, a light emitting layer 1113, and an electron transport A case where the layer 1114 and the electron injection layer 1115 are formed in this order will be described.

[0303] 10 minutes inside the vacuum chamber -4 After depressurizing to 100 Pa, 1,3,5-tri(dibenzothiophene-4 -yl)-benzene (abbreviation: DBT3P-II) and molybdenum(VI) oxide were 3P-II (abbreviation): molybdenum oxide = 4:2 (mass ratio) Thus, a hole injection layer 1111 was formed on the first electrode 1101. The film thickness was set to 40 nm. Co-evaporation is a method of simultaneously evaporating multiple different substances from different evaporation sources. It is law.

[0304] Next, 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine A hole transport layer 1112 is formed by depositing 20 nm of BPAFLP. Ta.

[0305] Next, the light-emitting layer 1113 was formed on the hole-transporting layer 1112. 2mDibenzo[f,h]quinoxaline (abbreviation: 2mDB TPDBq-II), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl Phenyl (abbreviation: NPB), bis{2-[6-(3,5-dimethylphenyl)-4-pyridine 2,6-dimethyl-3,5- Heptanedionate-κ 2 O,O')iridium(III) (abbreviation: [Ir(dmdppm ) 2(dibm)]) to 2mDBTPDBq-II (abbreviation): NPB (abbreviation): [Ir (dmdppm) 2 (dibm)] (abbreviation) = 0.8:0.2:0.05 (mass ratio) The film thickness was set to 40 nm.

[0306] Next, 2mDBTPDBq-II (abbreviation) was applied to the light-emitting layer 1113 at a thickness of 10 nm. By sequentially depositing 20 nm of benzophenone (abbreviation: Bphen), a laminated structure was formed. Further, lithium fluoride was deposited on the electron transport layer 1114. An electron injection layer 1115 was formed by vapor deposition.

[0307] Finally, aluminum was evaporated onto the electron injection layer 1115 to a thickness of 200 nm. Then, a second electrode 110 serving as a cathode was formed, and a light-emitting element 2 was obtained. In all the depositions, a resistance heating method was used.

[0308] The element structure of the thus obtained Light-emitting Element 2 is shown in Table 3.

[0309] [Table 3]

[0310] The fabricated light-emitting element 2 was placed in a glove box with a nitrogen atmosphere to prevent it from being exposed to the air. (Sealing material was applied around the element, and heat treatment was performed at 80°C for 1 hour during sealing.) ).

[0311] <Operation characteristics of light-emitting element 2> The operating characteristics of the fabricated light-emitting element 2 were measured. The measurements were performed at room temperature (25° C.). The atmosphere was very friendly.

[0312] First, the current density-luminance characteristics of the light-emitting element 2 are shown in FIG. is the luminance (cd / m 2 ), the horizontal axis is the current density (mA / cm 2 ) is shown. Also, the light-emitting element 2 The voltage-luminance characteristics are shown in FIG. 24. In FIG. 24, the vertical axis represents luminance (cd / m 2 ), The horizontal axis represents voltage (V). The luminance vs. current efficiency characteristics of the light-emitting element 2 are shown in FIG. In FIG. 25, the vertical axis represents current efficiency (cd / A) and the horizontal axis represents luminance (cd / m 2 ) Furthermore, the voltage-current characteristics of the light-emitting element 2 are shown in FIG. indicates current (mA), and the horizontal axis indicates voltage (V).

[0313] As shown in FIG. 25, the organometallic complex [Ir(dmdppm) 2 (dibm )] (abbreviation) in a part of the light-emitting layer was found to be a highly efficient element. Also, 1000cd / m 2 The main initial characteristic values ​​of the light-emitting element 2 in the vicinity are shown in Table 4 below. vinegar.

[0314] [Table 4]

[0315] From the above results, it can be seen that the light-emitting element 2 fabricated in this example has high luminance and shows good current efficiency. Furthermore, it can be seen that the color purity is excellent, and that the device shows reddish-orange emission with good purity. I understand.

[0316] In addition, the light-emitting element 2 is rated at 2.5 mA / cm 2 Emission spectrum when a current is applied at a current density of As shown in FIG. 27, the emission spectrum of the light-emitting element 2 is around 610 nm. The organometallic complex [Ir(dmdppm) 2 (dibm)] (abbreviation) It is suggested that this is due to luminescence. Ir(dmdppm) 2 (dibm)] (abbreviation) instead of the organometallic complex [Ir(dpp m) 2 (acac)] (abbreviation) was used to prepare comparative light-emitting element 2, and the light emission of comparative light-emitting element 2 was The spectrum is also shown as a comparative example. As a result, the emission spectrum of the light-emitting element 2 is as follows: It was confirmed that the half-width was narrower than that of the comparative light-emitting element 2. This is because the organometallic complex [Ir(dmdppm) 2 In the structure of (dibm), iridium is bonded This is due to the fact that the 2- and 4-positions of the phenyl group are substituted with methyl groups. Therefore, the light-emitting element 2 is a light-emitting element with good luminous efficiency and good color purity. It can be said that.

[0317] A reliability test was also conducted on the light-emitting element 2. The results of the reliability test are shown in FIG. In FIG. 28, the vertical axis represents the normalized luminance (%) when the initial luminance is 100%. The horizontal axis indicates the driving time (h) of the element. d / m 2 The light-emitting element 2 was driven under a constant current density condition. The luminance of 2 after 100 hours was approximately 86% of the initial luminance. The vertical axis shows the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis shows the normalized luminance (%) when the element is driven. The reliability test was performed by setting the current value to 0.3 mA and driving the light-emitting element 2. As a result, the luminance of the light-emitting element 2 after 100 hours was approximately 90% of the initial luminance. was.

[0318] Therefore, the light-emitting element 2 exhibits high reliability under any of the reliability tests performed under any conditions. In addition, by using the organometallic complex of one embodiment of the present invention for a light-emitting element, It was found that a light-emitting element with a long life could be obtained. EXAMPLES

[0319] In this example, an organometallic complex [Ir(dmdppm) 2 (dpm )] (abbreviation) (structural formula (108)) is used in the light-emitting layer. In the description of the light-emitting element 3 in this embodiment, reference is made to FIG. 15 used in the description of the light-emitting element 1 in the embodiment 4. The chemical formulas of the materials used in this embodiment are shown below.

[0320] [ka]

[0321] <Fabrication of light-emitting element 3> First, indium tin oxide containing silicon oxide (ITSO) is deposited on a glass substrate 1100. A film was formed by sputtering to form a first electrode 1101 that functions as an anode. The film thickness was 110 nm, and the electrode area was 2 mm x 2 mm.

[0322] Next, as a pretreatment for forming a light emitting element on the substrate 1100, the substrate surface is washed with water. After baking at 200°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0323] Then, 10 -4The substrate 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 the deposition apparatus, the substrate 1100 is It was left to cool for about 30 minutes.

[0324] Next, the substrate 1100 is vacuum-steamed so that the surface on which the first electrode 1101 is formed faces downward. In this example, the EL layer 1 was formed by vacuum deposition. 102 comprises a hole injection layer 1111, a hole transport layer 1112, a light emitting layer 1113, and an electron transport A case where the layer 1114 and the electron injection layer 1115 are formed in this order will be described.

[0325] 10 minutes inside the vacuum chamber -4 After depressurizing to 100 Pa, 1,3,5-tri(dibenzothiophene-4 -yl)benzene (abbreviation: DBT3P-II) and molybdenum(VI) oxide were P-II (abbreviation): molybdenum oxide = 4:2 (mass ratio) Thus, a hole injection layer 1111 was formed on the first electrode 1101. The thickness of the layer was set to 40 nm. Co-evaporation is a method of vapor deposition in which different substances are vaporized simultaneously from different sources. It is.

[0326] Next, 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine A hole transport layer 1112 is formed by depositing 20 nm of BPAFLP. Ta.

[0327] Next, the light-emitting layer 1113 was formed on the hole-transporting layer 1112. 2mDBTPD Bq-II), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl NPB, bis{2-[6-(3,5-dimethylphenyl)-4-pyrimidinyl {K(N3)-4,6-dimethylphenyl-K(C)}(2,2',6,6'-tetramethyl -3,5-heptanedionate-κ 2 O,O') Iridium(III) (abbreviation: [Ir(d mdppm) 2 (dpm)]) and 2mDBTPDBq-II (abbreviation):NPB (abbreviation) :[Ir(dmdppm) 2 (dpm)](abbreviation) = 0.8:0.2:0.025(mass The film thickness was set to 40 nm.

[0328] Next, 2mDBTPDBq-II (abbreviation) was applied to the light-emitting layer 1113 at a thickness of 10 nm. By sequentially depositing 20 nm of benzophenone (abbreviation: Bphen), a laminated structure was formed. Further, lithium fluoride was deposited on the electron transport layer 1114. An electron injection layer 1115 was formed by vapor deposition.

[0329] Finally, aluminum was evaporated onto the electron injection layer 1115 to a thickness of 200 nm. Then, a second electrode 1103 serving as a cathode was formed, and a light-emitting element 3 was obtained. In all depositions, a resistance heating method was used.

[0330] The element structure of the thus obtained Light-emitting Element 3 is shown in Table 5.

[0331] [Table 5]

[0332] The fabricated light-emitting element 3 was placed in a glove box with a nitrogen atmosphere to prevent it from being exposed to the air. (Sealing material was applied around the element, and heat treatment was performed at 80°C for 1 hour during sealing.) ).

[0333] <Operation characteristics of light-emitting element 3> The operating characteristics of the fabricated light-emitting element 3 were measured. The measurements were performed at room temperature (25° C.). The atmosphere was very friendly.

[0334] First, the current density-luminance characteristics of the light-emitting element 3 are shown in FIG. is the luminance (cd / m 2 ), the horizontal axis is the current density (mA / cm 2 ) is shown. Also, the light-emitting element 3 The voltage-luminance characteristics are shown in FIG. 31. In FIG. 31, the vertical axis indicates luminance (cd / m 2 ), The horizontal axis represents voltage (V). The luminance vs. current efficiency characteristics of the light-emitting element 3 are shown in FIG. In FIG. 32, the vertical axis represents current efficiency (cd / A) and the horizontal axis represents luminance (cd / m 2 ) Furthermore, the voltage-current characteristics of the light-emitting element 3 are shown in FIG. indicates current (mA), and the horizontal axis indicates voltage (V).

[0335] As shown in FIG. 32, the organometallic complex [Ir(dmdppm) 2 (dpm) It was found that the light-emitting element 3, in which the light-emitting layer contained the compound (abbreviation) was a highly efficient element. Also, 1000cd / m 2 The main initial characteristic values ​​of the light-emitting element 3 in the vicinity are shown in Table 6 below. .

[0336] [Table 6]

[0337] From the above results, it can be seen that the light-emitting element 3 fabricated in this example has high luminance and shows good current efficiency. Furthermore, it can be seen that the color purity is excellent, and that the device shows reddish-orange emission with good purity. I understand.

[0338] In addition, the light-emitting element 3 is supplied with 2.5 mA / cm 2 Emission spectrum when a current is applied at a current density of As shown in FIG. 34, the emission spectrum of the light-emitting element 3 is around 610 nm. The organometallic complex [Ir(dmdppm) 2 (dpm)] (abbreviation) It is suggested that the light is responsible for this. r(dmdppm) 2 (dpm)] (abbreviation) instead of the organometallic complex [Ir(dppm) 2 (acac)] (abbreviation) was used to prepare comparative light-emitting element 3, and the emission spectrum of comparative light-emitting element 3 was As a result, the emission spectrum of the light-emitting element 3 is It was confirmed that the half-width was narrower than that of Light-emitting Device 3. This is because the organometallic complex [I r(dmdppm) 2 In the structure of the compound (abbreviation: diphenyl ether (dpm)), phenanthroline is bonded to iridium. This is due to the structure in which the 2- and 4-positions of the methyl group are substituted with methyl groups. Therefore, it can be said that the light-emitting element 3 is a light-emitting element with good luminous efficiency and good color purity. do.

[0339] In addition, a reliability test was performed on the light-emitting element 3. The results of the reliability test are shown in FIG. In FIG. 35, the vertical axis represents the normalized luminance (%) when the initial luminance is 100%. The horizontal axis indicates the driving time (h) of the element. d / m2 The light-emitting element 3 was driven under a constant current density condition. The luminance of 3 after 100 hours was approximately 85% of the initial luminance. The vertical axis shows the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis shows the normalized luminance (%) when the element is driven. The reliability test was performed by setting the current value to 0.3 mA and driving the light-emitting element 3. As a result, the luminance of the light-emitting element 3 after 100 hours was maintained at about 90% of the initial luminance. was.

[0340] Therefore, the light-emitting element 3 exhibits high reliability under any of the reliability tests performed under any conditions. In addition, by using the organometallic complex of one embodiment of the present invention for a light-emitting element, It was found that a light-emitting element with a long life could be obtained. EXAMPLES

[0341] In this example, a phosphorescence spectrum obtained by calculation will be described. The chemical formula of the organometallic complex used is shown below.

[0342] [ka]

[0343] ≪Calculation example≫ [Ir(ppr) 2 (acac)] (abbreviation) and a suspected organometallic complex according to one embodiment of the present invention. Similar model structure [Ir(dmppr) 2 (acac)] (abbreviation) S 0 ) and the lowest excited triplet state (T 1 ) using density functional theory (DFT) to determine the most stable structure. In addition, vibration analysis was performed for each of the most stable structures, and S 0 and T 1 The transition probability between the vibrational states of was calculated, and the phosphorescence spectrum was calculated. The total energy of DFT is Potential energy, electrostatic energy, kinetic energy and complex interelectron energy In DFT, the exchange-correlation energy is expressed as the sum of all the interactions. The function is approximated by a functional (a function of a function) of the one-electron potential expressed in terms of electron density. The calculation is fast because of this. Here, we use the mixed functional B3PW91 to calculate the exchange and The weight of each parameter related to the correlation energy was defined.

[0344] In addition, the basis functions are 6-311G (valence orbitals for each of the H, C, N, and O atoms) Basis functions of triple split valence basis set using three shortening functions ) was used for the Ir atom, and LanL2DZ was used for the Ir atom. If it is a carbon atom, the orbitals 1s to 3s are considered, and if it is a carbon atom, the orbitals 1s to 4s and 2p to The 4p orbital is taken into account. Furthermore, to improve the accuracy of the calculation, the polarized basis set is The p function was added to hydrogen atoms, and the d function was added to non-hydrogen atoms. The calculation was performed using Gaussian 09. The measurements were performed using a computer (SGI, Altix4700).

[0345] In addition, the [Ir(ppr) 2 (acac)] (abbreviation) and this As a pseudo model of an organometallic complex, [Ir(dmppr) 2 (acac) The phosphorescence spectrum of ] (abbreviation) is shown in Figure 38. In this calculation, the half-width is 135 cm - 1and takes Franck-Condon factors into account.

[0346] As shown in Figure 38, when comparing the two phosphorescence spectra, [Ir(ppr) 2 (ac ac)] (abbreviation) has a high intensity of the second peak near 640 nm, while [Ir (dmppr) 2 (acac)] (abbreviation) has a small intensity of the second peak around 690 nm. These secondary peaks are due to the stretching vibrations of the C-C and C-N bonds in the ligands. [Ir(dmppr) 2 (acac)] (abbreviation) shows that these stretching vibrations contribute to The transition probability between states is small. As a result, the pseudo-model of the organometallic complex, which is one aspect of the present invention, The structure is [Ir(dmppr) 2 (acac)] (abbreviation) is [Ir(ppr) 2 ( It can be seen that the line is narrower than that of the conventional optical fiber (abbreviation: acac).

[0347] In addition, the [Ir(ppr) 2 (acac)] (abbreviation) and this A pseudo-model structure of an organometallic complex, [Ir(dmppr) 2 (aca The results of comparing the dihedral angles of the benzene rings of The positions of the face angles are shown in Figure 39.

[0348] [Table 7]

[0349] As shown in Table 7, [Ir(ppr) 2 (acac)] (abbreviation) 0 and T 1 To The small dihedral angle in the benzene ring indicates that the planarity of the benzene ring is high and that the C-C bonds in the ligands are It is believed that the transition probability between vibrational states contributed by the stretching vibration of the CN bond is large. Ir(dmppr) 2 (acac)] (abbreviation) 0 and T 1 The value of the dihedral angle at is Since the benzene ring is large, its planarity is low, and the stretching vibration of the C-C and C-N bonds in the ligand is small. This is because the transition probability between vibrational states contributed by the phenyl group is small. This is thought to be the effect of the two methyl groups. Substitution at the 2- and 4-positions of the bound phenyl group narrows the half-width of the phosphorescence spectrum. It was found that this improves the color purity of the emitted light. EXAMPLES

[0350] <Synthesis Example 4> In this Synthesis Example 4, an organic compound represented by the structural formula (121) of the first embodiment of the present invention is Metal complex, bis{4,6-dimethyl-2-[3-(3,5-dimethylphenyl)-5-phenyl phenyl-2-pyrazinyl-κN]phenyl-κC}(2,4-pentanedionato-κ 2 O ,O') Iridium(III) (abbreviation: [Ir(dmdppr-P) 2 (acac)]) The synthesis method of [Ir(dmdppr-P) 2 (acac)] (abbreviated) The structure of this compound (called

[0351] [ka]

[0352] Step 1: Di-μ-chloro-tetrakis{4,6-dimethyl-2-[3-(3,5 -Dimethylphenyl)-5-phenyl-2-pyrazinyl-κN]phenyl-κC}diyl Ir(dmdppr-P) 2 Cl] 2 Synthesis of First, mix 30 mL of 2-ethoxyethanol with 10 mL of water and 3 mL of Hdmdppr-P (abbreviation) .18g, Iridium chloride hydrate (IrCl 3 H 2 O) (Sigma-Aldrich 1.27 g of ethyl alcohol (manufactured by the company) was placed in a round-bottom flask equipped with a reflux condenser, and the atmosphere in the flask was replaced 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 give the binuclear complex [Ir(dm dppr-P) 2 Cl] 2 (abbreviation) was obtained (reddish brown powder, yield 67%). The synthesis scheme of 1 is shown in (d-1) below.

[0353] [ka]

[0354] Step 2: Bis{4,6-dimethyl-2-[3-(3,5-dimethylphenyl)- 5-Phenyl-2-pyrazinyl-κN]phenyl-κC}(2,4-pentanedionato- κ 2 O,O') Iridium(III) (abbreviation: [Ir(dmdppr-P) 2 (acac Synthesis of Furthermore, 40 mL of 2-ethoxyethanol and the binuclear complex [Ir(d mdppr-P) 2 Cl] 2(abbreviation) 2.8g, Acetylacetone (abbreviation: Hacac 0.46 g of ethyl acetate and 1.6 g of sodium carbonate were placed in a round-bottom flask equipped with a reflux condenser. The inside of the container was replaced with argon. After that, it was irradiated with microwaves (2.45 GHz, 120 W) for 1 hour. The solvent was removed by distillation, and the resulting residue was suction filtered with ethanol, and then washed with water and ethanol. The solid was extracted with ethyl acetate and hexane (1:10) as a developing solvent. The product was purified by flash column chromatography using a mixture of dichloromethane and ethanol. The organometallic complex [Ir(dmdppr -P) 2 (acac)] (abbreviation) was obtained as a dark red powder (yield 24%). The synthesis scheme is shown below in (d-2).

[0355] [ka]

[0356] The dark red powder obtained in step 2 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 40. In this Synthesis Example 4, an organometallic compound according to one embodiment of the present invention represented by the above structural formula (121) was Complex [Ir(dmdppr-P) 2 (acac)] (abbreviation) was obtained.

[0357] 1 H-NMR.δ(CDCl 3 ):1.41(s,6H),1.81(s,6H),1 .95(s,6H),2.42(s,12H),5.06(s,1H),6.46(s, 2H),6.81(s,2H),7.19(s,2H),7.41-7.49(m,10 H), 8.05(d,4H), 8.83(s,2H).

[0358] Next, [Ir(dmdppr-P) 2 (acac)] (abbreviation) in dichloromethane The ultraviolet-visible absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and the emission spectrum The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V55 manufactured by JASCO Corporation). A dichloromethane solution (0.085mmol / L) was placed in a quartz cell and heated at room temperature. The emission spectrum was measured using a fluorometer (Hamamatsu Photonics, Inc.). A degassed dichloromethane solution (0.085 mmol / L) was added to the The samples were placed in an English cell and measurements were performed at room temperature. The results are shown in Figure 41. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and the emission intensity. 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 41 is a dichloromethane solution (0. 0.085mmol / L) in a quartz cell and the absorption spectrum was measured. The absorption spectrum measured by placing only the sample in a quartz cell was subtracted from the results shown.

[0359] As shown in FIG. 41, the organometallic complex [Ir(dmdppr-P) 2 (acac)] (abbreviation) has an emission peak at around 633 nm and is Red light was observed from the solution.

[0360] Furthermore, the obtained [Ir(dmdppr-P) 2(acac)] (abbreviation) weight loss rate A high vacuum differential thermobalance (TG-DTA24 manufactured by Bruker AXS Co., Ltd.) was used. 10SA). Vacuum degree 8×10 -4 Pa, heating rate 10℃ / min As shown in FIG. 42, the organometallic complex [I r(dmdppr-P) 2 (acac)] (abbreviation) is a good product with a weight loss rate of 100%. It was found that the film exhibited good sublimation properties. EXAMPLES

[0361] <Synthesis Example 5> In this Synthesis Example 5, an organic compound represented by the structural formula (122) of the first embodiment of the present invention is Metal complex, bis{4,6-dimethyl-2-[5-(2,6-dimethylphenyl)-3-( 3,5-Dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,4-pentane Tandione-κ 2 O,O')iridium(III) (abbreviation: [Ir(dmdppr-d mp) 2 The synthesis method of [Ir(dmdppr- dmp) 2 The structure of (acac)] (abbreviation) is shown below.

[0362] [ka]

[0363] <Step 1: 2,3-bis(3,5-dimethylphenyl)pyrazine (abbreviation: Hdmdp Synthesis of pr) First, 5.00 g of 2,3-dichloropyrazine and 10 g of 3,5-dimethylphenylboronic acid were .23g, sodium carbonate 7.19g, bis(triphenylphosphine)palladium(I I) dichloride (abbreviation: Pd(PPh 3 ) 2 Cl 2 ) 0.29g, water 20mL, acetonite 20 mL of trifluoromethane was placed in a recovery flask equipped with a reflux condenser, and the inside of the flask was replaced with argon. The reaction vessel was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. Here, 2.55 g of 3,5-dimethylphenylboronic acid and 1.80 g of sodium carbonate are added. , Pd(PPh 3 ) 2 Cl 2 0.070g, 5 mL of water, and 5 mL of acetonitrile in a flask. Then, heat it again with microwaves (2.45GHz, 100W) for 60 minutes. Water was then added to this solution, and the organic layer was extracted with dichloromethane. The layer was washed with saturated aqueous sodium bicarbonate, water, and saturated saline, and then dried over magnesium sulfate. The dried solution was filtered. The solvent of this solution was distilled off, and the resulting residue was The mixture was extracted by flash column chromatography using hexane:ethyl acetate=5:1 as the developing solvent. The solvent was removed, and the resulting solid was extracted with dichloromethane:ethyl acetate=10:1. The desired pyrazine derivative H was obtained by purification using flash column chromatography with The compound dmdppr (abbreviation) was obtained (white powder, 44% yield). A microwave synthesizer (CEM Discover) was used. Synthesis scheme for step 1 is shown below in (e-1).

[0364] [ka]

[0365] Step 2: 5-(2,6-dimethylphenyl)-2,3-bis(3,5-dimethylphenyl) Synthesis of phenylpyrazine (abbreviation: Hdmdppr-dmp) Next, 2.81 g of 2-bromo-m-xylene and 30 mL of dry THF were added to a 200 mL three-port The flask was cooled to -78°C and then n-butyl ether was added. Then, 9.4 mL of 1.6 M hexane solution was added dropwise and the mixture was stirred at -78°C for one hour. Then, 4.01 g of Hdmdppr (abbreviation) obtained in step 1 above and 40 mL of dry THF The reaction solution was poured into water and extracted with chloroform. The organic layer was washed with water and saturated saline, and dried over magnesium sulfate. Manganese oxide was added and stirred for 30 minutes. Then, the solution was filtered and the solvent was distilled off. The residue was subjected to silica gel column chromatography using dichloromethane:hexane=1:1 as a developing solvent. The desired pyrazine derivative, Hdmdppr-dmp (abbreviation), was obtained. Yellowish white powder, 10% yield. The synthesis scheme of step 2 is shown in (e-2) below.

[0366] [ka]

[0367] <Step 3: Di-μ-chloro-tetrakis{4,6-dimethyl-2-[5-(2,6- Dimethylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl {Ir(dmdppr-dmp)} 2 Cl] 2 Synthesis of Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the Hdmdp obtained in step 2 above were 1.12 g of pr-dmp (abbreviation), iridium chloride hydrate (IrCl 3 H 2 O)(Si 0.39 g of dimethylformamide (made by Aldrich) was placed in a recovery flask equipped with a reflux condenser. The inside of the scope was replaced with argon. Then, microwaves (2.45 GHz, 100 W) were used for 1 hour. After the solvent was removed by distillation, the resulting residue was suction filtered and washed with hexane. Dinuclear complex [Ir(dmdppr-dmp) 2 Cl] 2 (abbreviation) was obtained (reddish brown powder, yield 98%). The synthetic scheme for step 3 is shown below (e-3).

[0368] [ka]

[0369] Step 4: Bis{4,6-dimethyl-2-[5-(2,6-dimethylphenyl)-3 -(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,4- Pentanedionate-κ 2 O,O')iridium(III) (abbreviation: [Ir(dmdppr -dmp) 2 Synthesis of (acac)] In addition, 30 mL of 2-ethoxyethanol and the binuclear complex [Ir(d mdppr-dmp) 2 Cl] 2 (abbreviation) 1.28g, acetylacetone (abbreviation: Hac ac) 0.19g of acetic acid and 0.68g of sodium carbonate were placed in a recovery flask equipped with a reflux condenser. The atmosphere in the flask was replaced with argon. Then, microwaves (2.45 GHz, 120 W) were applied for 6 h. The solvent was removed, and the resulting residue was filtered with ethanol. The obtained solid was washed with water and ethanol. The obtained solid was dissolved in dichloromethane. After filtering through a filter aid consisting of layers of Celite, alumina, and Celite, dichloromethane was added. The organic compound according to one embodiment of the present invention is recrystallized from a mixed solvent of hexane and ethanol. Metal complex [Ir(dmdppr-dmp) 2 (acac)] (abbreviation) was obtained as a red powder. The synthesis scheme of step 4 is shown below in (e-4).

[0370] [ka]

[0371] The red powder obtained in step 4 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 43. In Synthesis Example 5, an organometallic complex according to one embodiment of the present invention represented by the above structural formula (122) is Body [Ir(dmdppr-dmp) 2 (acac)] (abbreviation) was obtained. .

[0372] 1 H-NMR.δ(CDCl 3 ):1.48(s,6H),1.75(s,6H),1 .94(s,6H),2.12(s,12H),2.35(s,12H),5.17(s ,1H),6.47(s,2H),6.81(s,2H),7.08(d,4H),7. 12(s,2H),7.18(t,2H),7.40(s,4H),8.36(s,2H ).

[0373] Next, [Ir(dmdppr-dmp) 2(acac)] (abbreviation) in dichloromethane The ultraviolet-visible absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and emission spectrum of the liquid The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (JASCO Corporation). 550 type) and put a dichloromethane solution (0.062 mmol / L) into a quartz cell. The measurements were carried out at room temperature. The emission spectrum was measured using a fluorometer (Hamamatsu Photonics Co., Ltd.). A degassed dichloromethane solution (0.062 mmol / L) was used. The absorption and emission spectra were measured at room temperature. The measurement results are shown in FIG. 44. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity. In 44, 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. 44. The absorption spectrum is shown in FIG. 0.062mmol / L) in a quartz cell and the absorption spectrum was measured. The absorption spectrum measured by placing only tan in a quartz cell was subtracted from the result shown.

[0374] As shown in FIG. 44, the organometallic complex [Ir(dmdppr-dmp ) 2 (acac)] (abbreviation) has an emission peak at 610 nm and is Red-orange luminescence was observed from the solution.

[0375] Furthermore, the obtained [Ir(dmdppr-dmp) 2 Weight loss of (acac) (abbreviation) The small amount of the sample was measured using a high vacuum differential thermobalance (Bruker AXS, TG-DTA 2410SA) was used. Vacuum degree 8×10 -4 Pa, heating rate 10℃ / min n and the temperature was raised, the organometallic complex according to one embodiment of the present invention was [Ir(dmdppr-dmp) 2 (acac)] (abbreviation) means that the weight loss rate is 100%. It was found that the composition exhibited good sublimation properties.

[0376] Next, the [Ir(dmdppr-dmp) 2 (acac)] (abbreviation) Liquid Chromatography Mass Spectrometry The samples were analyzed by LC / MS (LC / MS Analysis).

[0377] For LC / MS analysis, LC (liquid chromatography) separation was performed using a Waters Acqu Mass spectrometry (MS) was performed using a Waters Xevo G2 T The LC separation was performed using an Acquity UPLC BEH MS. The column temperature was 40°C. Mobile phase A was acetonitrile, and mobile phase B was 0.1% formic acid aqueous solution. Concentration of [Ir(dmdppr-dmp) 2 (acac)] (abbreviation) was dissolved in chloroform. The solution was dissolved and diluted with acetonitrile to adjust the injection volume to 5.0 μL.

[0378] A gradient method was used for LC separation, which changes the composition of the mobile phase. The mobile phase A:mobile phase B ratio was 85:15 until 10 minutes, then the composition was changed. The ratio of mobile phase A to mobile phase B was 95:5. It was changed to A.

[0379] In the MS analysis, electrospray ionization was used. The capillary voltage was 3.0 kV. The sample cone voltage was 30 V, and detection was performed in positive mode. The range was m / z=100 to 1200.

[0380] The component with m / z=1075.45 that was separated and ionized under the above conditions was placed in the collision cell. The ions were dissociated into product ions by colliding with argon gas in a quartz cell. The energy (collision energy) for dissociation was 70 eV. The results of detecting the ions by time-of-flight (TOF) MS are shown in FIG.

[0381] From the results in FIG. 46 , it is clear that the organometallic complex of one embodiment of the present invention represented by structural formula (122) [Ir(dmdppr-dmp) 2 (acac)] (abbreviation) is mainly at m / z=973 Around .38, around m / z=957.35, around m / z=679.18, around m / z=577. It was found that product ions were detected near m / z = 477.10 and near 13. The results shown in Figure 46 are [Ir(dmdppr-dmp) 2 (acac)] (abbreviation) Since the results show characteristics derived from [Ir(dmd ppr-dmp) 2 (acac)] (abbreviation) is important data for identifying do.

[0382] The product ion at m / z=973.38 corresponds to the compound of formula (122). It is assumed that the cation is in a state in which acetylacetone and a proton are eliminated in the above-mentioned compound. This is one of the characteristics of organometallic complexes. The product ion at m / z=973.38 is estimated to be a methyl group loss. The organometallic complex [Ir(dmdppr-dmp) 2 (acac )] (abbreviation) contains a methyl group. EXAMPLES

[0383] <Synthesis Example 6> In this Synthesis Example 6, an organic compound represented by the structural formula (123) of the first embodiment of the present invention is Metal complex, bis{4,6-dimethyl-2-[3,5-bis(3,5-dimethylphenyl) -2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl-3,5-heptanedioate Nat-κ 2 O,O') Iridium(III) (abbreviation: [Ir(dmtppr) 2 (dib The synthesis method of [Ir(dmtppr) 2 (dibm)] The structure of (abbreviation) is shown below.

[0384] [ka]

[0385] <Step 1: 2,3-bis(3,5-dimethylphenyl)pyrazine (abbreviation: Hdmdp Synthesis of pr) First, 5.00 g of 2,3-dichloropyrazine and 10 g of 3,5-dimethylphenylboronic acid were .23g, sodium carbonate 7.19g, bis(triphenylphosphine)palladium(I I) dichloride (abbreviation: Pd(PPh 3 ) 2 Cl 2 ) 0.29g, water 20mL, acetonite 20 mL of trifluoromethane was placed in a recovery flask equipped with a reflux condenser, and the inside of the flask was replaced with argon. The reaction vessel was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. Here, 2.55 g of 3,5-dimethylphenylboronic acid and 1.80 g of sodium carbonate are added. , Pd(PPh 3 ) 2 Cl 2 0.070g, 5 mL of water, and 5 mL of acetonitrile in a flask. Then, heat it again with microwaves (2.45GHz, 100W) for 60 minutes. Water was then added to this solution, and the organic layer was extracted with dichloromethane. The layer was washed with saturated aqueous sodium bicarbonate, water, and saturated saline, and then dried over magnesium sulfate. The dried solution was filtered. The solvent of this solution was distilled off, and the resulting residue was The mixture was extracted by flash column chromatography using hexane:ethyl acetate=5:1 as the developing solvent. The solvent was removed, and the resulting solid was extracted with dichloromethane:ethyl acetate=10:1. The desired pyrazine derivative H was obtained by purification using flash column chromatography with The compound dmdppr (abbreviation) was obtained (white powder, 44% yield). A microwave synthesizer (CEM Discover) was used. Synthesis scheme for step 1 is shown below in (f-1).

[0386] [ka]

[0387] Step 2: 2,3,5-tris(3,5-dimethylphenyl)pyrazine (abbreviation: Hd Synthesis of mtppr) First, 2.81 g of 5-bromo-m-xylene and 30 mL of dry THF were added to a 200 mL three-port flask. The flask was cooled to -78°C and then n-butyl ether was added. Then, 9.4 mL of 1.6 M hexane solution was added dropwise and the mixture was stirred at -78°C for one hour. Then, 4.02 g of Hdmdppr (abbreviation) obtained in step 1 above and 40 mL of dry THF The reaction solution was poured into water and extracted with chloroform. The organic layer was washed with water and saturated saline, and dried over magnesium sulfate. Manganese dioxide was added and stirred for 30 minutes. The solution was then filtered and the solvent was distilled off. The residue was purified by silica gel column chromatography using dichloromethane:hexane=1:1 as a developing solvent. The product was purified by chromatography to obtain the desired pyrazine derivative Hdmtppr (abbreviation) (orange oil). The synthesis scheme of step 2 is shown in (f-2) below.

[0388] [ka]

[0389] <Step 3: Di-μ-chloro-tetrakis{4,6-dimethyl-2-[3,5-bis( 3,5-Dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}diiridium ( III) (Abbreviation: [Ir(dmtppr) 2 Cl] 2 Synthesis of Next, 30 mL of 2-ethoxyethanol, 10 mL of water, and the Hdmtp obtained in step 2 above were pr (abbreviation) 1.95g, iridium chloride hydrate (IrCl 3 H 2 O) (Sigma- 0.72 g of 1,2-dichloroethane (manufactured by Aldrich) was placed in a recovery flask equipped with a reflux condenser, and the flask was heated to 100° C. The atmosphere was replaced with argon. After that, microwaves (2.45 GHz, 100 W) were irradiated for 1 hour. After the solvent was distilled off, the resulting residue was suction filtered and washed with ethanol to obtain a binuclear complex. Body [Ir(dmtppr) 2 Cl] 2 (abbreviation) was obtained (reddish brown powder, 78% yield). In addition, the synthetic scheme of step 3 is shown in (f-3) below.

[0390] [ka]

[0391] Step 4: Bis{4,6-dimethyl-2-[3,5-bis(3,5-dimethylphenyl {2,6-dimethyl-3,5-heptane)-2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl-3,5-heptane Geonath-κ 2 O,O') Iridium(III) (abbreviation: [Ir(dmtppr) 2 (d ibm)] synthesis> In addition, 30 mL of 2-ethoxyethanol and the binuclear complex [Ir(d mtppr) 2 Cl] 2 (abbreviation) 0.89g, diisobutyrylmethane (abbreviation: Hdibm 0.20 g of 1,000 g of sodium carbonate and 0.47 g of sodium carbonate were placed in a recovery flask equipped with a reflux condenser. The inside of the scope was replaced with argon. Then, microwaves (2.45 GHz, 200 W) were used for 60 minutes. Then, 0.20 g of Hdibm was added and the mixture was again exposed to microwaves (2.45 GHz). The mixture was irradiated with 200W for 60 minutes. The solvent was removed, and 0.20g of Hdibm and sodium carbonate were added again. Add 0.47 g of sodium and 30 mL of 2-ethoxyethanol, and replace the atmosphere in the flask with argon. After that, it was heated by irradiating it with microwaves (2.45 GHz, 200 W) for 2 hours. The solvent was removed by distillation, and the resulting residue was subjected to suction filtration with ethanol. The resulting solid was dissolved in water, ethanol, and then filtered. The solid was dissolved in dichloromethane and washed with celite, alumina, and ceramist. After filtering through a filter aid layered in the order of fluoride, a mixture of dichloromethane and ethanol was By recrystallizing from a solvent, the organometallic complex [Ir(dmtpp r) 2 (dibm)] (abbreviation) was obtained as a dark red powder (yield 73%). The synthesis scheme is shown below in (f-4).

[0392] [ka]

[0393] The dark red powder obtained in step 4 above was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 47. In this Synthesis Example 6, the organometallic compound represented by the above structural formula (123) according to one embodiment of the present invention is Complex [Ir(dmtppr) 2 (dibm)] (abbreviation) was obtained.

[0394] 1 H-NMR.δ(CDCl 3 ):0.78(d,6H),0.99(d,6H),1 .41(s,6H),1.96(s,6H),2.24-2.30(m,2H),2.3 5(s,12H),2.42(s,12H),5.07(s,1H),6.46(s,2 H),6.78(s,2H),7.04(s,2H),7.18(s,2H),7.47 (s,2H),7.49(s,2H),7.67(s,4H),8.77(s,2H).

[0395] Next, [Ir(dmtppr) 2(dibm)] (abbreviation) in dichloromethane Visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured. The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V550, manufactured by JASCO Corporation). ) was used, and a dichloromethane solution (0.068 mmol / L) was placed in a quartz cell and measured at room temperature. The emission spectrum was measured using a fluorescence spectrometer (Hamamatsu Photonics, Ltd.). Using a quartz cell, a degassed dichloromethane solution (0.31 μmol / L) was placed in the quartz cell. The absorption and emission spectra were measured at room temperature. The horizontal axis shows the wavelength, and the vertical axis shows the absorption intensity and emission intensity. Two solid lines are shown, the thin one showing the absorption spectrum and the thick one showing the emission spectrum. The absorption spectrum shown in Figure 48 is that of a dichloromethane solution (0.068 The absorption spectrum of dichloromethane alone was measured using a quartz cell containing 1 mmol / L of The results shown are those obtained by subtracting the absorption spectrum measured in a quartz cell.

[0396] As shown in FIG. 48, the organometallic complex [Ir(dmtppr) 2 (d ibm)] (abbreviation) has an emission peak at around 629 nm, and in dichloromethane solution A reddish-orange emission was observed.

[0397] Next, the [Ir(dmtppr) 2 (dibm)] (abbreviation) Liquid Chromatography Mass Spectrometry The results were analyzed by liquid crystal / mass spectrometry (LC / MS analysis).

[0398] For LC / MS analysis, LC (liquid chromatography) separation was performed using a Waters Acqu Mass spectrometry (MS) was performed using a Waters Xevo G2 T The LC separation was performed using an Acquity UPLC BEH MS. The column temperature was 40°C. Mobile phase A was acetonitrile, and mobile phase B was 0.1% formic acid aqueous solution. Concentration of [Ir(dmtppr) 2 (dibm)] (abbreviation) was dissolved in chloroform and The solution was diluted with acetonitrile and the injection volume was 5.0 μL.

[0399] A gradient method was used for LC separation, which changes the composition of the mobile phase. The ratio of mobile phase A to mobile phase B was 90:10 until the first minute, then the composition was changed and the mobile phase A was The ratio of phase A to mobile phase B was set to 95:5, and the mixture was maintained for 10 minutes. The composition was changed linearly.

[0400] In the MS analysis, electrospray ionization was used. The capillary voltage was 3.0107 The voltage was 5 kV, the sample cone voltage was 30 V, and detection was in positive mode. The mass range was m / z=100 to 1200.

[0401] The component with m / z=1131.52 that was separated and ionized under the above conditions was placed in the collision cell. The ions were dissociated into product ions by colliding with argon gas in a quartz cell. The energy (collision energy) for dissociation was 70 eV. The results of detecting the ions by time-of-flight (TOF) MS are shown in FIG.

[0402] From the results in FIG. 49 , it is clear that the organometallic complex of one embodiment of the present invention represented by structural formula (123) [Ir(dmtppr) 2 (dibm)] (abbreviation) is mainly for m / z=973.38 It was found that a product ion was detected near m / z=583.17. The results shown in Figure 49 are [Ir(dmtppr) 2 (dibm)] (abbreviation) Since the results are consistent with those of the mixture, the [Ir(dmtppr) 2 (d This data is important for identifying the strain (abbreviation: IBM).

[0403] The product ion at m / z=973.38 corresponds to the compound of formula (123). It is assumed that the cation is in a state in which acetylacetone and a proton are eliminated in the above-mentioned compound. This is one of the characteristics of organometallic complexes. The ion is the ligand Hdmtppr-dmp (abbreviation) in the compound of structural formula (123). This is presumed to be a cation in which acetylacetone has been eliminated, and is an embodiment of the organic gold compound of the present invention. This is one of the characteristics of metal complexes. EXAMPLES

[0404] <Synthesis Example 7> In this Synthesis Example 7, an organic compound represented by the structural formula (124) of the first embodiment of the present invention is Metal complex, bis{4,6-dimethyl-2-[5-(2,6-dimethylphenyl)-3-( 3,5-Dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl Tyl-3,5-heptanedionate-κ 2O,O') Iridium(III) (abbreviation: [Ir (dmdppr-dmp) 2 The synthesis method of [I r(dmdppr-dmp) 2 The structure of (dibm)] (abbreviation) is shown below.

[0405] [ka]

[0406] <Step 1: 2,3-bis(3,5-dimethylphenyl)pyrazine (abbreviation: Hdmdp Synthesis of pr) First, 5.00 g of 2,3-dichloropyrazine and 10 g of 3,5-dimethylphenylboronic acid were .23g, sodium carbonate 7.19g, bis(triphenylphosphine)palladium(I I) dichloride (abbreviation: Pd(PPh 3 ) 2 Cl 2 ) 0.29g, water 20mL, acetonite 20 mL of trifluoromethane was placed in a recovery flask equipped with a reflux condenser, and the inside of the flask was replaced with argon. The reaction vessel was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. Here, 2.55 g of 3,5-dimethylphenylboronic acid and 1.80 g of sodium carbonate are added. , Pd(PPh 3 ) 2 Cl 2 0.070g, 5 mL of water, and 5 mL of acetonitrile in a flask. Then, heat it again with microwaves (2.45GHz, 100W) for 60 minutes. Water was then added to this solution, and the organic layer was extracted with dichloromethane. The layer was washed with saturated aqueous sodium bicarbonate, water, and saturated saline, and then dried over magnesium sulfate. The dried solution was filtered. The solvent of this solution was distilled off, and the resulting residue was The mixture was extracted by flash column chromatography using hexane:ethyl acetate=5:1 as the developing solvent. The solvent was removed, and the resulting solid was extracted with dichloromethane:ethyl acetate=10:1. The desired pyrazine derivative H was obtained by purification using flash column chromatography with The compound dmdppr (abbreviation) was obtained (white powder, 44% yield). A microwave synthesizer (CEM Discover) was used. Synthesis scheme for step 1 is shown below in (g-1).

[0407] [ka]

[0408] Step 2: 5-(2,6-dimethylphenyl)-2,3-bis(3,5-dimethylphenyl) Synthesis of phenylpyrazine (abbreviation: Hdmdppr-dmp) First, 2.81 g of 2-bromo-m-xylene and 30 mL of dry THF were added to a 200 mL three-port The flask was cooled to -78°C and then n-butyl ether was added. Then, 9.4 mL of 1.6 M hexane solution was added dropwise and the mixture was stirred at -78°C for one hour. Then, 4.01 g of Hdmdppr (abbreviation) obtained in step 1 above and 40 mL of dry THF The reaction solution was poured into water and extracted with chloroform. The organic layer was washed with water and saturated saline, and dried over magnesium sulfate. Manganese oxide was added and stirred for 30 minutes. Then, the solution was filtered and the solvent was distilled off. The residue was subjected to silica gel column chromatography using dichloromethane:hexane=1:1 as a developing solvent. The desired pyrazine derivative, Hdmdppr-dmp (abbreviation), was obtained. Yellowish white powder, 10% yield. The synthesis scheme of step 2 is shown in (g-2) below.

[0409] [ka]

[0410] <Step 3: Di-μ-chloro-tetrakis{4,6-dimethyl-2-[5-(2,6- Dimethylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl {Ir(dmdppr-dmp)} 2 Cl] 2 Synthesis of Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the dmdpp obtained in step 2 above were 1.12 g of r-dmp (abbreviation), iridium chloride hydrate (IrCl 3 H 2 O)(Sig 0.39 g of 10 ... The inside of the container was replaced with argon. After that, it was irradiated with microwaves (2.45 GHz, 100 W) for 1 hour. After the solvent was removed by distillation, the resulting residue was suction filtered and washed with hexane. Nuclear complex [Ir(dmdppr-dmp) 2 Cl] 2 (abbreviation) was obtained (reddish brown powder, yield 9 8%). The synthesis scheme for step 3 is shown below in (g-3).

[0411] [ka]

[0412] Step 4: Bis{4,6-dimethyl-2-[5-(2,6-dimethylphenyl)-3 -(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,6- Dimethyl-3,5-heptanedionate-κ 2 O,O') Iridium(III) (abbreviation: [ Ir(dmdppr-dmp) 2 Synthesis of (dibm)]) In addition, 30 mL of 2-ethoxyethanol and the binuclear complex [Ir(d mdppr-dmp) 2 Cl] 2 (abbreviation) 0.80g, diisobutyrylmethane (abbreviation: H 0.19 g of dibm and 0.42 g of sodium carbonate were placed in a recovery flask equipped with a reflux condenser. The flask was then filled with argon. Then, the flask was heated with microwaves (2.45 GHz, 120 W). The mixture was heated by irradiating with UV light for 60 minutes. The solvent was removed, and the resulting residue was dissolved in dichloromethane. However, after filtering through a filter aid consisting of layers of Celite, alumina, and Celite, By recrystallizing from a mixed solvent of chloromethane and methanol, one embodiment of the present invention Organometallic complex [Ir(dmdppr-dmp) 2 (dibm)] (abbreviation) as red powder The synthesis scheme of step 4 is shown below in (g-4).

[0413] [ka]

[0414] The red powder obtained in step 4 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 50. In Synthesis Example 7, an organometallic complex according to one embodiment of the present invention represented by the above structural formula (124) is Body [Ir(dmdppr-dmp) 2 (dibm)] (abbreviation) was obtained. .

[0415] 1 H-NMR.δ(CDCl 3 ):0.80(d,6H),0.81(d,6H),1 .47(s,6H),1.95(s,6H),2.10(s,12H),2.23-2. 28(m,2H),2.34(s,12H),5.19(s,1H),6.48(s,2 H),6.81(s,2H),7.06(d,4H),7.11(s,2H),7.16 (t,2H), 7.40(s,4H), 8.22(s,2H).

[0416] Next, [Ir(dmdppr-dmp) 2 (dibm)] (abbreviation) in dichloromethane The ultraviolet-visible absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and emission spectrum of the liquid The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (JASCO Corporation). 550 type) and put a dichloromethane solution (0.059 mmol / L) into a quartz cell. The measurements were carried out at room temperature. The emission spectrum was measured using a fluorometer (Hamamatsu Photonics Co., Ltd.). A degassed dichloromethane solution (0.059 mmol / L) was used. The absorption and emission spectra were measured at room temperature. The measurement results are shown in Figure 51. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity. In 51, 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 Figure 51. The absorption spectrum is shown in Figure 51. 0.059 mmol / L) in a quartz cell and the absorption spectrum was measured. The absorption spectrum measured by placing only tan in a quartz cell was subtracted from the result shown.

[0417] As shown in FIG. 51, the organometallic complex [Ir(dmdppr-dmp ) 2 (dibm)] (abbreviation) has an emission peak at around 616 nm and is dichloromethane. A reddish-orange emission was observed from the tannic solution.

[0418] Furthermore, the obtained [Ir(dmdppr-dmp) 2 (dibm)] (abbreviation) weight loss The small amount of the sample was measured using a high vacuum differential thermobalance (Bruker AXS, TG-DTA 2410SA) was used. Vacuum degree 1×10 -3 Pa, heating rate 10℃ / min n and the temperature was raised, the organometallic complex [ Ir(dmdppr-dmp) 2 (dibm)] (abbreviation) indicates that the weight loss rate is 100%. It was found that the polymer exhibited good sublimation properties.

[0419] Next, the [Ir(dmdppr-dmp) 2 (dibm)] (abbreviation) Liquid Chromatography Mass Spectrometry The samples were analyzed by LC / MS (LC / MS Analysis).

[0420] For LC / MS analysis, LC (liquid chromatography) separation was performed using a Waters Acqu Mass spectrometry (MS) was performed using a Waters Xevo G2 T The LC separation was performed using an Acquity UPLC BEH MS. The column temperature was 40°C. Mobile phase A was acetonitrile, and mobile phase B was 0.1% formic acid aqueous solution. Concentration of [Ir(dmdppr-dmp) 2 (dibm)] (abbreviation) was dissolved in chloroform. The solution was dissolved and diluted with acetonitrile to adjust the injection volume to 5.0 μL.

[0421] A gradient method was used for LC separation, which changes the composition of the mobile phase. The mobile phase A:mobile phase B ratio was 90:10 until 10 minutes, then the composition was changed. The ratio of mobile phase A to mobile phase B was 95:5. It was changed to A.

[0422] In the MS analysis, electrospray ionization was used. The capillary voltage was 3.0 kV. The sample cone voltage was 30 V, and detection was performed in positive mode. The range was m / z=100 to 1200.

[0423] The component with m / z=1131.52 that was separated and ionized under the above conditions was placed in the collision cell. The ions were dissociated into product ions by colliding with argon gas in a quartz cell. The energy (collision energy) for dissociation was 70 eV. The results of detecting the ions by time-of-flight (TOF) MS are shown in FIG.

[0424] From the results in FIG. 53 , it is clear that the organometallic complex of one embodiment of the present invention represented by structural formula (124) [Ir(dmdppr-dmp) 2 (dibm)] (abbreviation) is mainly m / z=973 Around .38, around m / z=959.36, around m / z=581.16, around m / z=555. It was found that product ions were detected around m / z = 393.23. The results shown in Figure 53 are [Ir(dmdppr-dmp) 2 (dibm)] (abbreviation) Since the results show characteristics derived from [Ir(dmd ppr-dmp) 2 (dibm)] (abbreviation) is important data for identifying do.

[0425] The product ion at m / z=973.38 corresponds to the compound of formula (124). It is assumed that the cation is in a state in which acetylacetone and a proton are eliminated in the above-mentioned compound. This is one of the characteristics of organometallic complexes. The product ion at m / z=973.38 is estimated to be a methyl group loss. The organometallic complex [Ir(dmdppr-dmp) 2 (dibm )] (abbreviation) contains a methyl group. EXAMPLES

[0426] <Synthesis Example 8> In this Synthesis Example 8, an organic compound represented by the structural formula (125) of the first embodiment of the present invention is Metal complex, bis{4,6-dimethyl-2-[5-(2,6-dimethylphenyl)-3-( 3,5-Dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,2',6 ,6'-Tetramethyl-3,5-heptanedionato-κ 2 O,O') Iridium(III ) (Abbreviation: [Ir(dmdppr-dmp) 2 We will explain the synthesis method of (dpm)]. Note that [Ir(dmdppr-dmp) 2 The structure of (dpm) (abbreviation) is shown below: .

[0427] [ka]

[0428] <Step 1: 2,3-bis(3,5-dimethylphenyl)pyrazine (abbreviation: Hdmdp Synthesis of pr) First, 5.00 g of 2,3-dichloropyrazine and 10 g of 3,5-dimethylphenylboronic acid were .23g, sodium carbonate 7.19g, bis(triphenylphosphine)palladium(I I) dichloride (abbreviation: Pd(PPh 3 ) 2 Cl 2 ) 0.29g, water 20mL, acetonite 20 mL of trifluoromethane was placed in a recovery flask equipped with a reflux condenser, and the inside of the flask was replaced with argon. The reaction vessel was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 60 minutes. Here, 2.55 g of 3,5-dimethylphenylboronic acid and 1.80 g of sodium carbonate are added. , Pd(PPh 3 ) 2 Cl 2 0.070g, 5 mL of water, and 5 mL of acetonitrile in a flask. Then, heat it again with microwaves (2.45GHz, 100W) for 60 minutes. Water was then added to this solution, and the organic layer was extracted with dichloromethane. The layer was washed with saturated aqueous sodium bicarbonate, water, and saturated saline, and then dried over magnesium sulfate. The dried solution was filtered. The solvent of this solution was distilled off, and the resulting residue was The mixture was extracted by flash column chromatography using hexane:ethyl acetate=5:1 as the developing solvent. The solvent was removed, and the resulting solid was extracted with dichloromethane:ethyl acetate=10:1. The desired pyrazine derivative H was obtained by purification using flash column chromatography with The compound dmdppr (abbreviation) was obtained (white powder, 44% yield). A microwave synthesizer (CEM Discover) was used. Synthesis scheme for step 1 is shown below in (h-1).

[0429] [ka]

[0430] Step 2: Synthesis of 2,3-bis(3,5-dimethylphenyl)pyrazine-1-oxide > Next, 6.6 g of Hdmdppr (abbreviation) obtained in step 1 above and 7 g of 3-chloroperbenzoic acid .8g and 90mL of dichloromethane were placed in a 300mL three-neck flask, and the inside of the flask was replaced with nitrogen. After stirring at room temperature for 24 hours, the reaction solution was poured into water and extracted with dichloromethane. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate and dried over magnesium sulfate. The resulting solution was filtered. The solvent was distilled off to obtain the desired pyrazine derivative (yellow Powder, 100% yield). The synthesis scheme for step 2 is shown below in (h-2).

[0431] [ka]

[0432] Step 3: Synthesis of 5-chloro-2,3-bis(3,5-dimethylphenyl)pyrazine > Next, 2,3-bis(3,5-dimethylphenyl)pyrazine-1 obtained in step 2 above was 7.0 g of 1,2-dioxide was placed in a 100 mL three-neck flask, and the inside of the flask was replaced with nitrogen. 20 mL of phosphoryl was added and the mixture was stirred at 100° C. for 1 hour. The reaction solution was poured into water and chloroform was added. The resulting organic layer was washed with a saturated aqueous solution of sodium bicarbonate, water, and saturated saline. The solution was then washed and dried over magnesium sulfate. The dried solution was filtered. The solvent of this solution was distilled off. The desired pyrazine derivative was obtained (gray powder, 90% yield). The model is shown below (h-3).

[0433] [ka]

[0434] Step 4: 5-(2,6-dimethylphenyl)-2,3-bis(3,5-dimethylphenyl) Synthesis of phenylpyrazine (abbreviation: Hdmdppr-dmp) Next, 5-chloro-2,3-bis(3,5-dimethylphenyl) obtained in step 3 above Pyrazine 1.21g, 2,6-dimethylphenylboronic acid 1.10g, sodium carbonate 0 .78g, Pd(PPh 3 ) 2 Cl 2 15mg, 14mL water, 14mL acetonitrile The reaction mixture was placed in a recovery flask equipped with a reflux condenser and argon was bubbled through for 15 minutes. The vessel was irradiated with microwaves (2.45 GHz, 100 W) for 3 hours. Methylphenylboronic acid 0.55g, sodium carbonate 0.39g, Pd(PPh 3 ) 2 C l 2 7 mg was placed in a flask and argon was bubbled through for 15 minutes. The mixture was heated by irradiation with microwaves (2.45 GHz, 100 W) for 3 hours. The solid was washed with ethanol. The solid was dissolved in dichloromethane. The alumina was filtered through a filter aid layered in the order Celite, alumina and Celite. The desired pyrazine derivative Hdmdppr-dmp (abbreviation) was obtained (white powder, yield 89%). %). The synthetic scheme of step 4 is shown below (h-4).

[0435] [ka]

[0436] <Step 5; Di-μ-chloro-tetrakis{4,6-dimethyl-2-[5-(2,6- Dimethylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl {Ir(dmdppr-dmp)} 2 Cl] 2 Synthesis of Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the dmdpp obtained in step 4 above were 1.12 g of r-dmp (abbreviation), iridium chloride hydrate (IrCl 3 H 2 O)(Sig 0.39 g of 10 ... The inside of the container was replaced with argon. After that, it was irradiated with microwaves (2.45 GHz, 100 W) for 1 hour. After the solvent was removed by distillation, the resulting residue was suction filtered and washed with hexane. Nuclear complex [Ir(dmdppr-dmp) 2 Cl] 2 (abbreviation) was obtained (reddish brown powder, yield 9 8%). The synthetic scheme for step 5 is shown below (h-5).

[0437] [ka]

[0438] Step 6: Bis{4,6-dimethyl-2-[5-(2,6-dimethylphenyl)-3 -(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,2' ,6,6'-Tetramethyl-3,5-heptanedionato-κ 2 O,O') Iridium (I II) (Abbreviation: [Ir(dmdppr-dmp) 2 Synthesis of (dpm)] In addition, 30 mL of 2-ethoxyethanol and the binuclear complex [Ir(d mdppr-dmp) 2 Cl] 2 (abbreviation) 1.38g, dipivaloylmethane (abbreviation: Hd Put 0.39 g of pm and 0.73 g of sodium carbonate into a recovery flask equipped with a reflux condenser. The atmosphere in the flask was replaced with argon. Then, microwaves (2.45 GHz, 120 W) were applied for 6 h. The solvent was removed, and the resulting residue was suction filtered with methanol. The obtained solid was washed with water and methanol. The obtained solid was dissolved in dichloromethane. After filtering through a filter aid consisting of layers of Celite, alumina, and Celite, dichloromethane was added. The organic compound according to one embodiment of the present invention is recrystallized from a mixed solvent of fluoromethane and methanol. Metal complex [Ir(dmdppr-dmp) 2 (dpm)] (abbreviation) was obtained as a dark red powder. The synthesis scheme of step 6 is shown below in (h-6).

[0439] [ka]

[0440] The dark red powder obtained in step 6 above was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 54. In this Synthesis Example 8, the organometallic compound represented by the above structural formula (125) according to one embodiment of the present invention is Complex [Ir(dmdppr-dmp) 2 (dpm)] (abbreviation) was obtained. .

[0441] 1 H-NMR.δ(CDCl 3 ):0.90(s,18H),1.46(s,6H), 1.95(s,6H),2.10(s,12H),2.34(s,12H),5.57( s,1H),6.47(s,2H),6.81(s,2H),7.06(d,4H),7 .11(s,2H),7.16(t,2H),7.38(s,4H),8.19(s,2 H).

[0442] Next, [Ir(dmdppr-dmp) 2 (dpm)] (abbreviation) in dichloromethane The ultraviolet-visible absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and emission spectrum of The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (JASCO V5000, Japan Spectroscopy Corporation). A dichloromethane solution (0.058 mmol / L) was placed in a quartz cell. The emission spectrum was measured using a fluorescence spectrometer (Hamamatsu Photonics Co., Ltd.). A degassed dichloromethane solution (0.058 mmol / L) was The samples were placed in a quartz cell and measurements were performed at room temperature. The measurement results are shown in FIG. 55. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity. In Fig. 5, two solid lines are shown, the thin solid line showing the absorption spectrum and the thick solid line showing the The emission spectrum is shown in Figure 55. The absorption spectrum is shown in Figure 55 for a dichloromethane solution (0 The absorption spectrum of dichloromethane (.058 mmol / L) in a quartz cell was The absorption spectrum of the sample measured by placing only the sample in a quartz cell was subtracted from the results shown in the figure.

[0443] As shown in FIG. 55, the organometallic complex [Ir(dmdppr-dmp ) 2 (dpm)] (abbreviation) has an emission peak at around 618 nm and is A reddish-orange emission was observed from the solution.

[0444] Furthermore, the obtained [Ir(dmdppr-dmp) 2 (dpm)] (abbreviation) weight loss The rate was measured using a high vacuum differential thermobalance (TG-DTA2 manufactured by Bruker AXS Co., Ltd.). 410SA). Vacuum degree 1×10 -3 Pa, heating rate 10℃ / min As shown in FIG. 56, the organometallic complex [I r(dmdppr-dmp) 2 (dpm)] (abbreviation) has a weight loss rate of 97%, which is good. It was found that the film exhibited good sublimation properties. EXAMPLES

[0445] In this example, an organometallic complex [Ir(dmdppr-P) 2 (a cac)] (abbreviation) (structural formula (121)) was used in the light-emitting layer. ppr-dmp) 2 (acac)] (abbreviation) (structural formula (122)) was used as the light-emitting layer. Element 5, [Ir(dmtppr) 2 (dibm)] (abbreviation) (structural formula (123)) emits light The light-emitting element 6 used in the layer, [Ir(dmdppr-dmp) 2 (dibm)] (abbreviation) (structure The light-emitting device 7 using the formula (124) in the light-emitting layer will be described. The light-emitting elements 4 to 7 will be described with reference to FIG. 15 used for the description of the light-emitting element 1 in Example 4. The chemical formulas of the materials used in this embodiment are shown below.

[0446] [ka]

[0447] [ka]

[0448] <Fabrication of Light-Emitting Devices 4 to 7> First, indium tin oxide containing silicon oxide (ITSO) is deposited on a glass substrate 1100. A film was formed by sputtering to form a first electrode 1101 that functions as an anode. The film thickness was 110 nm, and the electrode area was 2 mm x 2 mm.

[0449] Next, as a pretreatment for forming a light emitting element on the substrate 1100, the substrate surface is washed with water. After baking at 200°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0450] Then, 10 -4 The substrate 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 the deposition apparatus, the substrate 1100 is It was left to cool for about 30 minutes.

[0451] Next, the substrate 1100 is vacuum-steamed so that the surface on which the first electrode 1101 is formed faces downward. In this example, the EL layer 1 was formed by vacuum deposition. 102 comprises a hole injection layer 1111, a hole transport layer 1112, a light emitting layer 1113, and an electron transport A case where the layer 1114 and the electron injection layer 1115 are formed in this order will be described.

[0452] 10 minutes inside the vacuum chamber -4 After depressurizing to 100 Pa, 1,3,5-tri(dibenzothiophene-4 -yl)benzene (abbreviation: DBT3P-II) and molybdenum(VI) oxide were P-II (abbreviation): molybdenum oxide = 4:2 (mass ratio) Thus, a hole injection layer 1111 was formed on the first electrode 1101. The thickness of the layer was set to 20 nm. Co-evaporation is a method of vapor deposition in which different substances are vaporized simultaneously from different sources. It is.

[0453] Next, 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine A hole transport layer 1112 is formed by depositing 20 nm of BPAFLP. Ta.

[0454] Next, a light-emitting layer 1113 was formed on the hole transport layer 1112. In the case of the light-emitting element 4, DBTPDBq-II (abbreviation), NPB (abbreviation), [Ir(dmdppr-P) 2 (ac ac)](abbreviation) was used as a mdppr-P) 2 (acac)] (abbreviation) = 0.8:0.2:0.05 (mass ratio) In the case of the light-emitting element 5, the film thickness was 40 nm. 2mDBTPDBq-II (abbreviation), NPB (abbreviation), [Ir(dmdppr-dmp) 2 (acac)] (abbreviation), 2mDBTPDBq-II (abbreviation): NPB (abbreviation): [ Ir(dmdppr-dmp) 2(acac)] (abbreviation) = 0.8:0.2:0.05 ( The film thickness was 40 nm. In the case of 6, 2mDBTPDBq-II (abbreviation), NPB (abbreviation), [Ir(dmtpp r) 2 (dibm)] (abbreviation), 2mDBTPDBq-II (abbreviation): NPB (abbreviation) :[Ir(dmtppr) 2 (dibm)](abbreviation) = 0.8:0.2:0.05(mass The thickness of the film was 40 nm. In the case of 2mDBTPDBq-II (abbreviation), NPB (abbreviation), [Ir(dmdppr -dmp) 2 (dibm)] (abbreviation), 2mDBTPDBq-II (abbreviation): NPB ( Abbreviation: [Ir(dmdppr-dmp) 2 (dibm)](abbreviation)=0.8:0.2: The layers were co-evaporated so that the mass ratio was 0.05, and the film thickness was 40 nm.

[0455] Next, 2mDBTPDBq-II (abbreviation) was applied to the light-emitting layer 1113 at 20 nm, and By sequentially depositing 20 nm of benzophenone (abbreviation: Bphen), a laminated structure was formed. Further, lithium fluoride was deposited on the electron transport layer 1114. An electron injection layer 1115 was formed by vapor deposition.

[0456] Finally, aluminum was evaporated onto the electron injection layer 1115 to a thickness of 200 nm. Then, a second electrode 1103 serving as a cathode was formed, and light-emitting elements 4 to 7 were obtained. In all deposition processes, the deposition was performed using a resistance heating method.

[0457] Table 8 shows the element structures of Light-emitting Elements 4 to 7 obtained as above.

[0458] [Table 8]

[0459] The fabricated light-emitting elements 4 to 7 were placed in a nitrogen atmosphere to prevent exposure to the air. The device was sealed in a cavity box (sealing material was applied around the device and the device was sealed at 80°C). Heat treatment for 1 hour).

[0460] <Operation characteristics of light-emitting elements 4 to 7> The operating characteristics of the fabricated light-emitting elements 4 to 7 were measured. The experiment was carried out in an atmosphere maintained at 5°C.

[0461] First, current density-luminance characteristics of the light-emitting elements 4 to 7 are shown in FIG. In this case, the vertical axis is luminance (cd / m 2 ), the horizontal axis is the current density (mA / cm 2 ) Also, FIG. 58 shows the voltage-luminance characteristics of the light-emitting elements 4 to 7. In FIG. is the luminance (cd / m 2 ), and the horizontal axis represents voltage (V). The luminance-current efficiency characteristics are shown in FIG. 59. In FIG. 59, the vertical axis represents current efficiency (cd / A), the horizontal axis is luminance (cd / m 2 Furthermore, the voltage-voltage of the light-emitting elements 4 to 7 is shown. The current characteristics are shown in FIG. 60. In FIG. 60, the vertical axis represents current (mA) and the horizontal axis represents voltage ( V).

[0462] As shown in FIG. 59, the organometallic complex [Ir(dmdppr-P) 2 (ac ac)] (abbreviation) (structural formula (121)), [Ir(dmdppr-dmp) 2 (acac )](abbreviation)(structural formula (122)), [Ir(dmtppr) 2 (dibm)] (abbreviation) (Structural formula (123)), [Ir(dmdppr-dmp) 2 (dibm)] (abbreviation) (structure The light-emitting elements 4 to 7 each have a light-emitting layer containing the compound represented by formula (124) It was found to be a highly efficient element. 2 Light-emitting element 4 in the vicinity The main initial characteristic values ​​of the light-emitting element 7 are shown in Table 9 below.

[0463] [Table 9]

[0464] From the above results, the light-emitting devices 4 to 7 fabricated in this example have high luminance and good current efficiency. Furthermore, it can be seen that the color purity is excellent, and that the red-orange emission is excellent. It can be seen that...

[0465] In addition, light-emitting elements 4 to 7 were supplied with 2.5 mA / cm 2 The emission spectrum when a current is applied at a current density of As shown in FIG. 61, the emission spectra of the light-emitting elements 5 and 7 are The emission spectrum of the light-emitting element 4 and the light-emitting element 6 is around 617 nm. The peaks are due to the emission of the organometallic complexes contained in the respective light-emitting elements. In addition, the emission spectra of the light-emitting elements 4 to 7 all have a half-width of This is because the structure of the organometallic complex used in this example is The phenyl group bonded to the rhodium has a structure in which the 2- and 4-positions are substituted with methyl groups. Therefore, the light-emitting elements 4 to 7 have good luminous efficiency and color purity. It can be said that this is a light-emitting element with good light-emitting properties.

[0466] In addition, a reliability test was performed on the light-emitting elements 4 to 7. The results of the reliability test are shown in FIG. In FIG. 62, the vertical axis represents the normalized luminance (%) when the initial luminance is 100%. The horizontal axis indicates the driving time (h) of the element. 0 cd / m 2 The light-emitting elements 4 to 7 were driven under a constant current density condition. The luminance of the light-emitting element 4 after 100 hours was about 60% of the initial luminance, and the luminance of the light-emitting element 5 after 38 hours was about 60% of the initial luminance. The luminance of the light-emitting element 6 after 40 hours was about 88% of the initial luminance. The luminance of the light-emitting element 7 after 39 hours was maintained at about 86% of the initial luminance. In FIG. 63, the vertical axis indicates normalized luminance (%) when the initial luminance is 100%, and the horizontal axis indicates normalized luminance (%) when the initial luminance is 100%. The axis indicates the operation time (h) of the element. The reliability test was performed with the current value set to 0.3 mA. The light-emitting elements 4 to 7 were driven. As a result, the luminance of the light-emitting element 4 after 100 hours was approximately the same as the initial luminance. The luminance of the light-emitting element 5 after 100 hours was about 91% of the initial luminance. The luminance of the light-emitting element 6 after 100 hours was about 90% of the initial luminance, and the luminance of the light-emitting element 7 after 100 hours was about 90% of the initial luminance. The brightness remained at approximately 86% of the initial brightness.

[0467] Therefore, under any condition of the reliability test, the light-emitting elements 4 to 7 exhibited high reliability. In addition, it was found that the organometallic complex according to one embodiment of the present invention can be used for a light-emitting element. It was found that a light emitting element having a long life can be obtained by this. EXAMPLES

[0468] <Synthesis Example 9> In this Synthesis Example 9, an organic compound represented by the structural formula (126) of the first embodiment of the present invention is used. Metal complex, bis{4,6-dimethyl-2-[5-(2,6-dimethylphenyl)-2-pyridinyl Rimidinyl-κN]phenyl-κC}(2,4-pentanedionato-κ 2 O,O') Iri Ir(dmppm2-dmp) 2 (acac)]) synthesis method The method is explained below. Note that [Ir(dmppm2-dmp) 2 (acac)] (abbreviation) The structure is shown below.

[0469] [ka]

[0470] <Step 1: Synthesis of 5-bromo-2-(3,5-dimethylphenyl)pyrimidine> First, 2.97 g of 5-bromo-2-iodopyrimidine and 3,5-dimethylphenylboron 1.62g of phosphonic acid, 1.21g of sodium carbonate, bis(triphenylphosphine)palladium Pd(II) dichloride (abbreviation: Pd(PPh 3 ) 2 Cl 2 )0.093g, water 20mL, 20 mL of acetonitrile was placed in a recovery flask equipped with a reflux condenser and bubbled with argon for 15 minutes. The reaction vessel was irradiated with microwaves (2.45 GHz, 100 W) for 1 hour. The mixture was heated in a 100% aqueous solution of 0.40 g of 3,5-dimethylphenylboronic acid and sodium carbonate. 0.30g, Pd(PPh 3 ) 2 Cl 2 Put 0.024g into the flask and let sit for 15 minutes. Argon was bubbled through the reaction vessel. The reaction vessel was then heated again with a microwave (2.45 GHz, 100 W). The mixture was heated by irradiation for 1 hour.

[0471] Next, water was added to this solution, and the organic layer was extracted with dichloromethane. The mixture was washed with water and saturated saline, and then dried over magnesium sulfate. The solution after drying was filtered. After distilling off the solvent, the residue was extracted with hexane:ethyl acetate=5:1. The fractions were concentrated and purified by flash column chromatography. The solid was subjected to flash column chromatography using dichloromethane:hexane=1:1 as a developing solvent. The product was purified by HPLC to obtain the desired pyrimidine derivative (white powder, 33% yield). For microwave irradiation, a microwave synthesis device (Discover, manufactured by CEM) was used. The synthetic scheme of step 1 is shown below in (i-1).

[0472] [ka]

[0473] <Step 2; 5-(2,6-dimethylphenyl)-2-(3,5-dimethylphenyl) Synthesis of pyrimidine (abbreviation: Hdmppm2-dmp) Next, 0.91 g of 5-bromo-2-(3,5-dimethylphenyl)pyrimidine and 2,6 -Dimethylphenylboronic acid 1.05g, sodium carbonate 0.74g, bis(triphenyl Pd(PPh)dichloride 3 ) 2 Cl 2 )0. 029g, 13mL of water, and 13mL of acetonitrile were placed in a recovery flask equipped with a reflux condenser. The reaction vessel was heated to 100° C., and argon was bubbled for 15 minutes. The reaction vessel was heated to 100° C., and argon was bubbled for 15 minutes. The mixture was heated by irradiating it with 100 W for 4 hours. Here, 2,6-dimethylphenylboronic acid was further added. 1.07g, sodium carbonate 0.73g, Pd(PPh 3 ) 2 Cl 2 0.029g The reaction vessel was placed in a lasso and bubbled with argon for 15 minutes. The reaction vessel was again placed in a microwave (2. The mixture was heated by irradiation with a 45 GHz 100 W power supply for 3 hours. The solid was filtered by suction at 37° C. The solid was then diluted with toluene and hexane (1:1) as a developing solvent. The desired pyrimidine derivative, Hdmppm2-dm p (abbreviation) was obtained (white powder, 83% yield). The synthesis scheme of step 2 is shown below (i-2 ) as shown in

[0474] [ka]

[0475] <Step 3: Di-μ-chloro-tetrakis{4,6-dimethyl-2-[5-(2,6- Dimethylphenyl)-2-pyrimidinyl-κN]phenyl-κC}diiridium(III )(Abbreviation: [Ir(dmppm2-dmp) 2 Cl] 2 Synthesis of Next, 15 mL of 2-ethoxyethanol, 5 mL of water, and the Hdmpp obtained in step 2 above were m2-dmp (abbreviation) 0.83 g, iridium chloride hydrate (IrCl 3 H 2 O)(Si 0.39 g of dimethylformamide (made by Aldrich) was placed in a recovery flask equipped with a reflux condenser. The inside of the scope was replaced with argon. Then, microwaves (2.45 GHz, 100 W) were used for 1 hour. After the solvent was removed by distillation, the resulting residue was suction filtered and washed with hexane. Dinuclear complex [Ir(dmppm2-dmp) 2 Cl] 2 (abbreviation) was obtained (brown powder, yield 91%). The synthetic scheme for step 3 is shown below in (i-3).

[0476] [ka]

[0477] Step 4: Bis{4,6-dimethyl-2-[5-(2,6-dimethylphenyl)- 2-Pyrimidinyl-κN]phenyl-κC}(2,4-pentanedionato-κ 2 O,O' ) Iridium(III) (abbreviation: [Ir(dmppm2-dmp) 2 (acac)] Synthesis> Next, 30 mL of 2-ethoxyethanol and the binuclear complex [Ir(dm ppm2-dmp) 2 Cl] 2 (abbreviation) 0.95g, Acetylacetone (abbreviation: Haca c) 0.18 g of sodium chloride and 0.63 g of sodium carbonate were placed in a recovery flask equipped with a reflux condenser. The atmosphere in the LASCO was replaced with argon. Then, microwaves (2.45 GHz, 120 W) were applied for 60 At this point, 0.18 g of Haccac was added and the mixture was again exposed to microwaves (2.45 GHz). The mixture was heated by irradiation with a 300 W (200 W) for 60 minutes. The solvent was removed, and the resulting residue was dissolved in methanol. The solid was filtered off under suction with alcohol. The solid was washed with water and methanol. The mixture was analyzed by flash column chromatography using xanthene:ethyl acetate = 5:1 as a developing solvent. After purification, the compound was recrystallized in a mixed solvent of dichloromethane and methanol to obtain the compound of the present invention. One example of the organometallic complex [Ir(dmppm2-dmp) 2 (acac)] (abbreviation ) was obtained as a yellow-orange powder (yield 14%). The synthesis scheme of step 4 is shown below (i-4). As shown in.

[0478] [ka]

[0479] The yellow-orange powder obtained in step 4 above was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 64. In Synthesis Example 9, the organometallic compound represented by the above structural formula (126) according to one embodiment of the present invention is Complex [Ir(dmppm2-dmp) 2 (acac)] (abbreviation) was obtained. Ta.

[0480] 1 H-NMR.δ(CDCl 3 ):1.58(s,6H),1.62(s,6H),2 .03(s,6H),2.15(s,6H),2.28(s,6H),5.17(s,1 H),6.63(d,2H),7.15(t,4H),7.24(t,2H),7.81 (d,2H),8.39(d,2H),8.53(d,2H). EXAMPLES

[0481] <Synthesis Example 10> In this Synthesis Example 10, the compound represented by the structural formula (127) of the embodiment 1 of the present invention is synthesized. Organometallic complexes, bis{4,6-dimethyl-2-[6-(2,6-dimethylphenyl)-4- Pyrimidinyl-κN3]phenyl-κC}(2,4-pentanedionato-κ2 O,O') Iridium(III) (abbreviation: [Ir(dmppm-dmp) 2 Synthesis of (acac)] The method is explained below. 2 (acac)] (abbreviation) The structure is shown below.

[0482] [ka]

[0483] <Step 1: Synthesis of 4-chloro-6-(3,5-dimethylphenyl)pyrimidine> First, 5.05 g of 4,6-dichloropyrimidine and 5 g of 3,5-dimethylphenylboronic acid were .08g, sodium carbonate 3.57g, bis(triphenylphosphine)palladium(I I) dichloride (abbreviation: Pd(PPh 3 ) 2 Cl 2 ) 0.14g, acetonitrile 20m Put 20 mL of water into a round-bottom flask equipped with a reflux condenser and bubble argon through it for 15 minutes. After that, the mixture was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 1 hour. After heating, 2.54 g of 3,5-dimethylphenylboronic acid and 1.79 g of sodium carbonate were added. g, Pd(PPh 3 ) 2 Cl 2 0.066g was added and argon bubbling was performed for 15 minutes. .

[0484] Next, the mixture was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 1 hour. After heating, 1.27 g of 3,5-dimethylphenylboronic acid, Pd(PPh 3 ) 2 Cl 2 0.0 91g was added and argon bubbling was performed for 15 minutes. The mixture was heated by irradiating it with a 100W (100W) lamp for 1 hour. The organic layer was extracted with dichloromethane. The extract was washed with water and saturated saline, and then dried over magnesium sulfate. The solvent was removed from the solution by distillation, and the resulting residue was diluted with dichloromethane as a developing solvent. The desired pyrimidine derivative was obtained by purifying the product by silica gel column chromatography. The product was a yellow crystal, yield 31%. Microwave irradiation was performed using a microwave synthesis device (CEM Corporation). The synthesis scheme of step 1 is shown below in (j-1).

[0485] [ka]

[0486] <Step 2: 6-(2,6-dimethylphenyl)-4-(3,5-dimethylphenyl) Synthesis of pyrimidine (abbreviation: Hdmppm-dmp)> Next, 4-chloro-6-(3,5-dimethylphenyl)pyrimidinium obtained in step 1 above was 1.18g, 2,6-dimethylphenylboronic acid 0.754g, sodium carbonate 0.5 35g, bis(triphenylphosphine)palladium(II) dichloride (abbreviation: Pd( PPh 3 ) 2 Cl 2 0.036g, acetonitrile 10mL, water 10mL, reflux condenser The mixture was placed in a round-bottom flask equipped with a microwave oven and argon was bubbled through for 15 minutes. The material was heated by irradiation with a 100 W power source (2.45 GHz, 100 W) for 1 hour. Nylboronic acid 0.380g, sodium carbonate 0.268g, Pd(PPh 3 ) 2 Cl2 0 .020 g was added and argon was bubbled through for 15 minutes.

[0487] Next, the mixture was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 3 hours. , 6-Dimethylphenylboronic acid 0.404g, sodium carbonate 0.277g, Pd(P Ph 3 ) 2 Cl 2 0.019g was added, and argon bubbling was performed for 15 minutes. The mixture was heated by microwave irradiation (2.45 GHz, 100 W) for 3 hours. Add 10 mL of ethanol and 10 mL of water, and irradiate with microwaves (2.45 GHz, 100 W) for 3 hours. The organic layer was extracted with dichloromethane, and the extract was diluted with water and saturated saline. The solution was filtered and the solvent of this solution was was distilled off to obtain a residue.

[0488] Similarly, 4-chloro-6-(3,5-dimethylphenyl)pyrimidinium salt obtained in step 1 above was 1.13g of gin, 0.802g of 2,6-dimethylphenylboronic acid, 0. 548g, Pd(PPh 3 ) 2 Cl 2 0.040g, acetonitrile 20mL, water 20m L was placed in a round-bottom flask equipped with a reflux condenser, and argon was bubbled through for 15 minutes. The mixture was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 2 hours. Dimethylphenylboronic acid 0.408g, sodium carbonate 0.288g, Pd(PPh 3 ) 2 Cl 2 0.021 g was added, and argon bubbling was performed for 15 minutes.

[0489] Next, the mixture was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 4 hours. Acetonitrile 7mL, 2,6-dimethylphenylboronic acid 0.214g, sodium carbonate 0.273g, Pd(PPh 3 ) 2 Cl 2 Add 0.020g and argon bubbling for 1 The test was performed for 5 minutes. The test was then irradiated with microwaves (2.45 GHz, 100 W) for 2.5 hours. The organic layer was extracted with dichloromethane, and the extract was washed with water and saturated saline. The solution was filtered and the solvent was removed by distillation. A residue was obtained.

[0490] The two residues obtained were subjected to silica gel column chromatography using dichloromethane as a developing solvent. The fractions were concentrated, and the resulting solid was dissolved in dichloromethane and purified by chromatography. Dissolve and filter through a filter aid layered in the following order: Celite, alumina, Celite. This gave 0.3 g of crude crystals (yellow).

[0491] Next, the 4-chloro-6-(3, 5-Dimethylphenyl)pyrimidine 1.10g, 2,6-dimethylphenylboronic acid 0. 753g, sodium carbonate 0.534g, Pd(PPh 3 ) 2 Cl 2 0.038g, 1, 3-Dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidinone (abbreviation: DMP U) 20 mL of acetone and 20 mL of water were placed in a round-bottom flask equipped with a reflux condenser and argon was bubbled through the flask. After that, the sample was irradiated with microwaves (2.45 GHz, 100 W) for 1 hour. The mixture was heated with 0.376 g of 2,6-dimethylphenylboronic acid and 0. 269g, Pd(PPh 3 ) 2 Cl 2 Add 0.011g and argon bubble for 15 minutes. Went for a while.

[0492] Next, the mixture was heated by irradiating it with microwaves (2.45 GHz, 100 W) for 2 hours. The organic layer was extracted with dichloromethane, and the extract was washed with water and saturated saline to obtain magnesium sulfate. The solution after drying was filtered, and the solvent was distilled off to obtain a residue. The residue and the yellow crude crystals were combined and then eluted on silica gel using dichloromethane and ethyl acetate as the developing solvent. The desired pyrimidine derivative, Hdmppm-dmp, was obtained by purification using column chromatography. (abbreviation) was obtained (yellow oil, yield 34%). The synthesis scheme of step 2 is shown below (j-2 ) as shown in

[0493] [ka]

[0494] <Step 3: Di-μ-chloro-tetrakis{4,6-dimethyl-2-[6-(2,6- Dimethylphenyl)-4-pyrimidinyl-κN3]phenyl-κC}diiridium(II I) (Abbreviation: [Ir(dmppm-dmp) 2 Cl] 2 Synthesis of Next, 30 mL of 2-ethoxyethanol, 10 mL of water, and the Hdmppm obtained in step 2 were added to -dmp (abbreviation) 1.00 g, iridium chloride hydrate (IrCl 3 H 2 O)(Sigm 0.568 g of a-Aldrich was placed in a round-bottom flask equipped with a reflux condenser. The inside of the container was replaced with argon. After that, it was irradiated with microwaves (2.45 GHz, 100 W) for 1 hour. After the solvent was removed by distillation, the resulting residue was suction filtered and washed with hexane. Nuclear complex [Ir(dmppm-dmp) 2 Cl] 2 (abbreviation) was obtained (black solid, yield 79 %). The synthetic scheme of step 3 is shown below in (j-3).

[0495] [ka]

[0496] Step 4: Bis{4,6-dimethyl-2-[6-(2,6-dimethylphenyl)-4 -pyrimidinyl-κN3]phenyl-κC}(2,4-pentanedionato-κ 2 O,O' ) Iridium(III) (abbreviation: [Ir(dmppm-dmp) 2 (acac)]) > Next, 30 mL of 2-ethoxyethanol and the binuclear complex [Ir(dm ppm-dmp) 2 Cl] 2 (abbreviation) 0.606g, Acetylacetone (abbreviation: Haca c) 0.138 g of sodium chloride and 0.489 g of sodium carbonate are placed in a round-bottom flask equipped with a reflux condenser. The atmosphere in the flask was replaced with argon. Then, microwaves (2.45 GHz, 120 W) were applied. The mixture was heated by irradiation for 1 hour. The solvent was removed by distillation, and the resulting residue was dissolved in ethyl acetate:hexane. After purification by flash column chromatography using a developing solvent of 1:2, dichloromethane was The organometallic compound according to one embodiment of the present invention is recrystallized in a mixed solvent of methane and hexane. Complex [Ir(dmppm-dmp) 2 (acac)] (abbreviation) was obtained as a dark red powder ( The synthesis scheme of step 4 is shown below in (j-4).

[0497] [ka]

[0498] The dark red powder obtained in step 4 above was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 65. In this Synthesis Example 10, an organometallic compound represented by the above structural formula (127) according to one embodiment of the present invention was synthesized. Complexes [Ir(dmppm-dmp) 2 (acac)] (abbreviation) was obtained. Ta.

[0499] 1 H-NMR.δ(DMSO-d6): 1.43(s,6H), 1.70(s,6H) , 2.19(s,12H), 2.18(s,6H), 5.34(s,1H), 6.54( s,2H), 7.23(d,4H), 7.30-7.33(m,2H), 7.79(s, 2H), 8.23(s,2H), 8.95(ds,2H). EXAMPLES

[0500] <Synthesis Example 11> In this Synthesis Example 11, the compound represented by the structural formula (106) of the embodiment 1 of the present invention is synthesized. Organometallic complexes, bis{4,6-dimethyl-2-[6-tert-butyl-4-pyrimidinyl -κN3]phenyl-κC}(2,4-pentanedionato-κ 2 O,O') Iridium ( III) (Abbreviation: [Ir(tBudmppm) 2 The synthesis method of (acac)] is described below. In addition, [Ir(tBudmppm)2 The structure of (acac)] (abbreviation) is shown below. vinegar.

[0501] [ka]

[0502] <Step 1; Synthesis of 4-tert-butyl-6-hydroxypyrimidine> First, 7.2 g of formamidine hydrochloride, 7.5 g of sodium methoxide, 7 g of methanol Add 4,4-dimethyl-3-oxopropane to a 100-mL three-neck flask and add 100 mL of 10 g of methyl valerate was added and stirred at room temperature for 24 hours. A mixed solution of 7.2 mL of acetic acid was added and stirred at room temperature. The mixture was concentrated, and the resulting residue was The residue was dissolved in water and extracted with ethyl acetate. The resulting extract was washed with saturated saline and diluted with dimethyl sulfuric acid. The solution was dried over magnesium. After drying, the solution was filtered. After distilling off the solvent, The resulting solid was washed with ethyl acetate to obtain the desired pyrimidine derivative (white solid, yield 4 9%). The synthesis scheme for step 1 is shown below (k-1).

[0503] [ka]

[0504] <Step 2: Synthesis of 4-tert-butyl-6-chloropyrimidine> Next, 4-tert-butyl-6-hydroxypyrimidine 4.7 obtained in step 1 above was g, 14 mL of phosphoryl chloride was placed in a 50 mL three-neck flask and heated to reflux for 1.5 hours. After refluxing, phosphoryl chloride was distilled off under reduced pressure. The resulting residue was dissolved in dichloromethane. The mixture was washed with water and a saturated aqueous solution of sodium bicarbonate, and then 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 mixture was purified by silica gel column chromatography using ethyl acetate / ethyl acetate 10:1 as a developing solvent. The desired pyrimidine derivative was obtained (white solid, 78% yield). The model is shown in (k-2) below.

[0505] [ka]

[0506] <Step 3; 4-tert-butyl-6-(3,5-dimethylphenyl)pyrimidine Synthesis of (abbreviation: HtBudmppm)> Next, 2.01 g of 4-tert-butyl-6-chloropyrimidine obtained in step 2 above 3.63 g of 3,5-dimethylphenylboronic acid, 2.48 g of sodium carbonate, bis(t Triphenylphosphine)palladium(II) dichloride (abbreviation: Pd(PPh 3 ) 2 Cl 2 0.10 g of ) and 20 mL of water and 20 mL of DMF were placed in a recovery flask equipped with a reflux condenser. Argon was bubbled for 15 minutes. The reaction vessel was heated in a microwave (2.45 GHz, 100 W) was heated by irradiation for 60 minutes. Here, 3,5-dimethylphenylboronic acid 0.90g, sodium carbonate 0.64g, Pd(PPh 3 ) 2 Cl 2 0.025g The reaction vessel was placed in a lasso and bubbled with argon for 15 minutes. The reaction vessel was again placed in a microwave (2. The solution was heated by irradiating it with a 45 GHz (100 W) for 60 minutes. Water was then added to the solution. The organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and saturated saline, and The solution was dried over magnesium sulfate. After drying, the solution was filtered. The solvent was removed by distillation. The residue was then eluted on silica gel using a developing solvent of dichloromethane:ethyl acetate = 10:1. The pyrimidine derivative HtBudmppm was purified by column chromatography. (abbreviation) was obtained (light yellow oil, 96% yield). The synthesis scheme of step 3 is shown below. k-3).

[0507] [ka]

[0508] <Step 4; Di-μ-chloro-tetrakis{4,6-dimethyl-2-[6-tert- Butyl-4-pyrimidinyl-κN]phenyl-κC}diiridium(III) (abbreviation: [Ir(tBudmppm) 2 Cl] 2 Synthesis of Next, 30 mL of 2-ethoxyethanol, 10 mL of water, and the HtBu 2.69 g of dmppm (abbreviation), iridium chloride hydrate (IrCl 3 H 2 O)(Sig 1.48 g of 1.48 g of 1.25 ... The inside of the container was replaced with argon. After that, it was irradiated with microwaves (2.45 GHz, 100 W) for 1 hour. After the solvent was removed by distillation, the resulting residue was suction filtered and washed with ethanol. Dinuclear complex [Ir(tBudmppm) 2 Cl] 2 (abbreviation) was obtained (green powder, yield 62 %). The synthetic scheme of step 4 is shown below in (k-4).

[0509] [ka]

[0510] Step 5: Bis{4,6-dimethyl-2-[6-tert-butyl-4-pyrimidinyl {2,4-pentanedionato-κN3}phenyl-κC 2 O,O') Iridescence (III) (abbreviation: [Ir(tBudmppm) 2 Synthesis of (acac)] In addition, 30 mL of 2-ethoxyethanol and the binuclear complex [Ir(t Budmppm) 2 Cl] 2 (abbreviation) 0.98g, Acetylacetone (abbreviation: Hacac 0.21 g of ethyl acetate and 0.73 g of sodium carbonate were placed in a recovery flask equipped with a reflux condenser. The inside of the scope was replaced with argon. Then, microwaves (2.45 GHz, 200 W) were used for 60 minutes. Then, 0.21 g of Hacac (abbreviation) was added and the mixture was again exposed to microwaves (2.4 The mixture was heated by irradiation with a 5 GHz 100 W for 60 minutes. The solvent was removed by distillation, and the resulting residue was The solid was filtered off with ethanol and the solid was washed with water and ethanol. Dissolve in dichloromethane and layer celite, alumina, and celite in this order to form a filter aid. After filtering through a filter, the mixture was recrystallized from a mixture of dichloromethane and ethanol to obtain An organometallic complex according to one embodiment of the present invention [Ir(tBudmppm) 2 (acac)] (abbreviation ) was obtained as a yellow-orange powder (yield 61%). The synthesis scheme of step 5 is shown below (k-5). As shown in.

[0511] [ka]

[0512] The yellow-orange powder obtained in step 5 above was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 66. In this Synthesis Example 11, an organometallic compound represented by the above structural formula (106) according to one embodiment of the present invention was synthesized. Group complexes [Ir(tBudmppm) 2 (acac)] (abbreviation) was obtained. .

[0513] 1 H-NMR.δ(CDCl 3 ):1.38(s,6H),1.46(s,18H), 1.69(s,6H),2.26(s,6H),5.17(s,1H),6.55(s, 2H),7.43(s,2H),7.71(s,2H),8.87(s,2H). [Explanation of symbols]

[0514] 101 First electrode 102 EL layer 103 Second electrode 111 Hole injection layer 112 Hole transport layer 113 Light-emitting layer 114 Electron transport layer 115 Electron injection layer 116 Charge generation layer 201 Anode 202 Cathode 203 EL layer 204 Light-emitting layer 205 Phosphorescent compounds 206 The first organic compound 207 Second organic compound 301 First electrode 302(1) First EL layer 302(2) Second EL layer 302(n-1) EL layer (n-1) 302(n) EL layer (n) 304 Second electrode 305 Charge generation layer (I) 305(1) First charge generating layer (I) 305(2) Second charge generating layer (I) 305(n-2) (n-2)th charge generating layer (I) 305(n-1) th (n-1) charge generating layer (I) 401 Reflecting electrode 402 Semi-transparent / semi-reflective electrode 403a First transparent conductive layer 403b Second transparent conductive layer 404B First light-emitting layer (B) 404G Second light-emitting layer (G) 404R Third light-emitting layer (R) 405 EL layer 410R First light emitting element (R) 410G Second light-emitting element (G) 410B Third light-emitting element (B) 501 Element substrate 502 Pixel section 503 Driver circuit section (source line driver circuit) 504a, 504b Drive circuit section (gate line drive circuit) 505 Sealing material 506 Sealing substrate 507 Wiring 508 FPC (Flexible Printed Circuit) 509 n-channel TFT 510 p-channel TFT 511 Switching TFT 512 Current control TFT 513 First electrode (anode) 514 Insulation 515 EL layer 516 Second electrode (cathode) 517 Light emitting element 518 Space 1100 Substrate 1101 First electrode 1102 EL layer 1103 Second electrode 1111 Hole injection layer 1112 Hole transport layer 1113 Light-emitting layer 1114 Electron transport layer 1115 Electron injection layer 7100 Television equipment 7101 Case 7103 Display section 7105 Stand 7107 Display section 7109 Operation key 7110 Remote control device 7201 Main unit 7202 Case 7203 Display section 7204 Keyboard 7205 External connection port 7206 Pointing Device 7301 Case 7302 Case 7303 Connection section 7304 Display section 7305 Display section 7306 Speaker section 7307 Recording medium insertion section 7308 LED Lamp 7309 Operation key 7310 Connection terminal 7311 Sensor 7312 Microphone 7400 Mobile Phone 7401 Case 7402 Display section 7403 Operation button 7404 External connection port 7405 Speaker 7406 Mike 8001 Lighting equipment 8002 Lighting equipment 8003 Lighting equipment 8004 Lighting equipment 9033 Fastener 9034 Display mode change switch 9035 Power Switch 9036 Power saving mode switch 9038 Operation switch 9630 Case 9631 Display section 9631a Display section 9631b Display section 9632a Touch Panel Area 9632b Touch Panel Area 9633 Solar Cells 9634 Charge / discharge control circuit 9635 Battery 9636 DC-DC Converter 9637 Operation key 9638 Converter 9639 Button

Claims

1. A first light-emitting layer and a second light-emitting layer are disposed between a pair of electrodes, an aromatic amine compound and an electron acceptor are provided between the first light-emitting layer and the second light-emitting layer; The first light-emitting layer has an organometallic complex represented by formula (G1). 【Chemistry 1】 (In formula (G1), X represents any one of formulas (X1) to (X3). １ ~R ４ represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. 【Chemistry 2】 (In the formulas (X1) to (X3), R ５ ~R １３ each represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group.

2. A first light-emitting layer and a second light-emitting layer are disposed between a pair of electrodes, an aromatic amine compound and an electron acceptor are provided between the first light-emitting layer and the second light-emitting layer; The first light-emitting layer has an organometallic complex represented by formula (G2). 【Chemistry 3】 (In the formula (G2), R １ ~R ４ each represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; R ５ , R ６ each represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group; R ７ represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group.

3. A first light-emitting layer and a second light-emitting layer are disposed between a pair of electrodes, an aromatic amine compound and an electron acceptor are provided between the first light-emitting layer and the second light-emitting layer; The first light-emitting layer has an organometallic complex represented by formula (G3). 【Chemistry 4】 (In the formula (G3), R １ ~R ４ Each of R represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. ８ , R １０ R each represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. ９ represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group.

4. A first light-emitting layer and a second light-emitting layer are disposed between a pair of electrodes, an aromatic amine compound and an electron acceptor are provided between the first light-emitting layer and the second light-emitting layer; The first light-emitting layer has an organometallic complex represented by formula (G4). 【Chemistry 5】 (In the formula (G4), R １ ~R ４ Each of R represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. １１ represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. １２ , R １３ Each of R represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. １２ Or R １３ Either one of the groups may be hydrogen.)

5. In any one of claims 1 to 4, R １ and R ２ A light-emitting element having an organometallic complex in which

6. A first light-emitting layer and a second light-emitting layer are disposed between a pair of electrodes, an aromatic amine compound and an electron acceptor are provided between the first light-emitting layer and the second light-emitting layer; The first light-emitting layer has an organometallic complex represented by any one of formulas (100) to (105) and (121) to (125). 【Chemistry 6】 【Chemistry 7】

7. A first light-emitting layer and a second light-emitting layer are disposed between a pair of electrodes, an aromatic amine compound and an electron acceptor are provided between the first light-emitting layer and the second light-emitting layer; The first light-emitting layer has an organometallic complex represented by any one of formulas (106) to (111) and (127). 【Chemistry 8】

8. A first light-emitting layer and a second light-emitting layer are disposed between a pair of electrodes, an aromatic amine compound and an electron acceptor are provided between the first light-emitting layer and the second light-emitting layer; The first light-emitting layer has an organometallic complex represented by any one of formulas (112) to (117) and (126). 【Chemistry 9】

9. A light emitting device comprising the light emitting element according to claim 1 .

10. 9. A lighting device comprising the light-emitting element according to claim 1 as a light source.

11. 9. An electronic device comprising the light-emitting element according to claim 1.

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