Light-emitting device, light-emitting apparatus, light-emitting module, electronic appliance, and illumination apparatus

Abstract

To increase the luminous efficiency of a light-emitting device emitting near-infrared light, and increase the reliability of a light-emitting device emitting near-infrared light.SOLUTION: A light-emitting device using an organic compound emitting light with a maximum peak wavelength of 760 nm or more and 900 nm or less is provided. An organic metal complex represented by General Formula (G1) is provided.SELECTED DRAWING: None

Description

[Technical field]

[0001] One embodiment of the present invention is a light-emitting device, a light-emitting apparatus, a light-emitting module, an electronic device, a lighting apparatus, a photoelectric conversion device ... One aspect of the present invention relates to an organic metal complex, a light-emitting material, an organic compound, and a polynuclear complex. A light-emitting device, a light-emitting apparatus, a light-emitting module, an electronic device, a lighting apparatus, and a light-emitting element that emit near-infrared light. The present invention relates to an organometallic complex, a light-emitting material, an organic compound, and a polynuclear complex.

[0002] Note that one embodiment of the present invention is not limited to the above technical field. Examples of the semiconductor device include a semiconductor device, a display device, a light-emitting device, a power storage device, a memory device, an electronic device, a lighting device, Input devices (e.g., touch sensors, etc.), input / output devices (e.g., touch panels, etc.), These driving methods and manufacturing methods can be cited as examples. [Background technology]

[0003] Organic Electroluminescence (EL) Research and development of light-emitting devices that use electrons (also called organic EL devices or organic EL elements) is thriving. The basic structure of an organic electroluminescence (EL) device is a pair of electrodes between which a light-emitting organic compound is placed. The organic EL device is sandwiched between a layer containing a compound (hereinafter referred to as the light-emitting layer). By applying pressure, light can be emitted from the light-emitting organic compound.

[0004] Examples of light-emitting organic compounds include compounds that can convert a triplet excited state into light emission (phosphorescence In Patent Document 1, iridium is used as a phosphorescent material. Organometallic complexes having a central metal such as tungsten have been disclosed.

[0005] In addition, image sensors are used for various purposes such as personal authentication, defect analysis, medical diagnosis, and security-related applications. Image sensors use different wavelengths of light sources depending on the application. Image sensors use visible light, short-wavelength light such as X-rays, near-infrared light, etc. Various wavelengths of light are used, including long wavelength light.

[0006] In addition to display devices, light-emitting devices are also being considered for use as light sources for image sensors such as those mentioned above. is being defeated. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] JP 2007-137872 A Summary of the Invention [Problem to be solved by the invention]

[0008] One object of one embodiment of the present invention is to improve the emission efficiency of a light-emitting device that emits near-infrared light. One aspect of the present invention is to improve the reliability of a light-emitting device that emits near-infrared light. One object of the present invention is to extend the lifetime of a light-emitting device that emits near-infrared light. One of the goals is to

[0009] An object of one embodiment of the present invention is to provide an organometallic complex with high emission efficiency. An object of one embodiment of the present invention is to provide an organometallic complex with high chemical stability. An object of one embodiment of the present invention is to provide a novel organometallic complex that emits near-infrared light. In one embodiment of the present invention, a novel An object of the present invention is to provide an organometallic complex.

[0010] Note that the description of these problems does not preclude the existence of other problems. However, it is not necessary to solve all of these problems. It is possible to extract other issues from the description in the section. [Means for solving the problem]

[0011] One embodiment of the present invention is a light-emitting device (also referred to as a light-emitting element) having a light-emitting layer. The light emitting organic compound has a maximum peak wavelength (peak) of light emitted by the light emitting organic compound. The wavelength at which the radiation has the highest intensity is between 760 nm and 900 nm.

[0012] One embodiment of the present invention is a light-emitting device having a first electrode, a second electrode, and a light-emitting layer. The light-emitting layer is located between the first electrode and the second electrode. The light-emitting layer contains a light-emitting organic compound. The maximum peak wavelength of light emitted by luminescent organic compounds is between 760 nm and 900 nm. Below.

[0013] The maximum peak wavelength of the light emitted by the luminescent organic compound is preferably 780 nm or more. In addition, the maximum peak wavelength of the light emitted by the luminescent organic compound is 880 nm or less. is preferred.

[0014] The luminescent organic compound is preferably an organometallic complex having a metal-carbon bond. Among these, the light-emitting organic compound is more preferably a cyclometal complex. The light-emitting organic compound is preferably an orthometal complex. Preferably, the luminescent organic compound is an iridium complex. When the organometallic complex has a bond, the organometallic complex has a condensed complex having 2 to 5 rings. It is preferable that the condensed heteroaromatic ring has a metal atom and the condensed heteroaromatic ring is coordinated to a metal. The condensed heteroaromatic ring preferably has 3 or more rings. The condensed heteroaromatic ring preferably has 4 or less rings. It is preferable that there is.

[0015] One embodiment of the present invention is a light-emitting device having any of the above structures, and a transistor and a substrate. Alternatively, the light emitting device may have both of the above.

[0016] One embodiment of the present invention is a flexible printed circuit board (FPC) having the above-mentioned light-emitting device. ble printed circuit, hereafter referred to as FPC) or TCP (Ta Modules with connectors such as PE Carrier Package, or COG (Chip On Glass) or COF (Chip On Fi Light emitting modules, etc., in which integrated circuits (ICs) are mounted using the LM method, etc. The light-emitting module according to one aspect of the present invention has only one of a connector and an IC. It may have either one or both.

[0017] One aspect of the present invention is a light-emitting module including an antenna, a battery, a housing, a camera, a speaker, and the like. The electronic device has at least one of a speaker, a microphone, and an operation button.

[0018] One aspect of the present invention is a light-emitting device comprising at least one of a housing, a cover, and a support base. and a lighting device having the above structure.

[0019] One embodiment of the present invention is an organometallic complex represented by General Formula (G1). Another embodiment of the present invention is a light-emitting material represented by the general formula (G1). This is a material for light-emitting devices represented by (G1).

[0020] [ka]

[0021] In general formula (G1), R 1 ~R 11 are each independently hydrogen or a group having 1 to 6 carbon atoms. represents an alkyl group, R 1 ~R 4 At least two of the alkyl groups have 1 to 6 carbon atoms. represents a group, R 5 ~R 9 At least two of the groups represent alkyl groups having 1 to 6 carbon atoms. X represents a substituted or unsubstituted benzene ring or naphthalene ring, and n is 2 or 3. and L represents a monoanionic ligand.

[0022] One embodiment of the present invention is an organometallic complex represented by General Formula (G2). Another embodiment of the present invention is a light-emitting material represented by the general formula (G2). This is a material for light-emitting devices represented by (G2).

[0023] [ka]

[0024] In general formula (G2), R 1 , R 3 , R 6 , and R 8 Each independently has 1 to 6 carbon atoms. R represents the alkyl group below. 10 and R11 are each independently hydrogen or a group having one or more carbon atoms. 6 or less alkyl group, and X is a substituted or unsubstituted benzene ring or naphthalene ring. wherein n is 2 or 3, and L represents a monoanionic ligand.

[0025] The maximum light emitted by the organometallic complex, the light-emitting material, or the material for a light-emitting device according to one embodiment of the present invention The peak wavelength is preferably 760 nm or more and 900 nm or less.

[0026] One embodiment of the present invention is a light-emitting device having a light-emitting layer. The light-emitting device has an organometallic complex, a light-emitting material, or a material for a light-emitting device of up to It has the function of emitting light with a peak wavelength of 760 nm or more and 900 nm or less.

[0027] One embodiment of the present invention is an organic compound represented by general formula (G0).

[0028] [ka]

[0029] In general formula (G0), R 1 ~R 11 are each independently hydrogen or a group having 1 to 6 carbon atoms. represents an alkyl group, R 1 ~R 4 At least two of the alkyl groups have 1 to 6 carbon atoms. represents a group, R 5 ~R 9 At least two of the groups represent alkyl groups having 1 to 6 carbon atoms. , X represents a substituted or unsubstituted benzene ring or naphthalene ring.

[0030] One embodiment of the present invention is an organic compound represented by structural formula (200).

[0031] [ka]

[0032] One embodiment of the present invention is a dinuclear complex represented by general formula (B).

[0033] [ka]

[0034] In the general formula (B), Z represents a halogen, R 1 ~R 11 are each independently hydrogen or carbon Represents an alkyl group with a prime number of 1 to 6, and R 1 ~R 4 At least two of the Represents the six or fewer alkyl groups, R 5 ~R 9 At least two of the following have 1 to 6 carbon atoms: and X represents a substituted or unsubstituted benzene ring or naphthalene ring.

[0035] One embodiment of the present invention is a dinuclear complex represented by structural formula (210).

[0036] [ka] Effect of the Invention

[0037] According to one embodiment of the present invention, the light-emitting efficiency of a light-emitting device that emits near-infrared light can be improved. According to one embodiment of the present invention, the reliability of a light-emitting device that emits near-infrared light can be improved. According to one embodiment of the present invention, the lifetime of a light-emitting device that emits near-infrared light can be extended. .

[0038] According to one embodiment of the present invention, an organometallic complex with high emission efficiency can be provided. According to one embodiment of the present invention, an organometallic complex that can emit near-infrared light and has high chemical stability can be provided. According to one embodiment of the present invention, a novel organometallic complex that emits light can be provided. It is possible to provide a novel organometallic complex that can be used for the above-mentioned purposes.

[0039] The description of these effects does not preclude the existence of other effects. However, it is not necessary to have all of these effects. However, it is possible to extract effects other than these. [Brief description of the drawings]

[0040] [Figure 1] 1A, 1B, and 1C are cross-sectional views showing an example of a light-emitting device. [Diagram 2] Fig. 2A is a top view showing an example of a light emitting device, and Fig. 2B and Fig. 2C are cross-sectional views showing an example of the light emitting device. [Diagram 3] Fig. 3A is a top view showing an example of a light emitting device, and Fig. 3B is a cross-sectional view showing an example of the light emitting device. [Figure 4] 4A to 4E are diagrams showing an example of an electronic device. [Diagram 5] FIG. 5 is a 1H-NMR chart of the organic compound represented by the structural formula (200). [Figure 6] FIG. 6 is a 1H-NMR chart of the organometallic complex shown in structural formula (100). [Figure 7] FIG. 7 shows the ultraviolet-visible absorption spectrum and emission spectrum of the organometallic complex represented by the structural formula (100). [Figure 8] FIG. 8 is a graph showing the weight change rate of the organometallic complex represented by the structural formula (100). [Figure 9] 9A and 9B are cross-sectional views showing a light-emitting device according to an embodiment. [Figure 10] FIG. 10 is a graph showing the current density-radiant emittance characteristics of the light-emitting device 1. As shown in FIG. [Figure 11] FIG. 11 is a graph showing the voltage-current density characteristics of the light-emitting device 1. As shown in FIG. [Figure 12] FIG. 12 is a graph showing the current density-radiant flux characteristics of the light-emitting device 1. As shown in FIG. [Figure 13] FIG. 13 is a graph showing the voltage-radiant emittance characteristics of the light-emitting device 1. As shown in FIG. [Figure 14] FIG. 14 is a graph showing the current density-external quantum efficiency characteristics of the light-emitting device 1. As shown in FIG. [Figure 15] FIG. 15 is a diagram showing the emission spectrum of the light-emitting device 1. As shown in FIG. [Figure 16] FIG. 16 is a diagram showing the results of a reliability test of the light emitting device 1. As shown in FIG. [Figure 17] FIG. 17 is a graph showing the current density-radiant emittance characteristics of the light-emitting device 2. As shown in FIG. [Figure 18] FIG. 18 is a graph showing the voltage-current density characteristics of the light-emitting device 2. As shown in FIG. [Figure 19] FIG. 19 is a graph showing the current density-radiant flux characteristics of the light-emitting device 2. As shown in FIG. [Figure 20] FIG. 20 is a graph showing the voltage-radiant emittance characteristics of the light-emitting device 2. As shown in FIG. [Figure 21] FIG. 21 is a graph showing the current density-external quantum efficiency characteristics of the light-emitting device 2. As shown in FIG. [Figure 22] FIG. 22 is a diagram showing the emission spectrum of the light-emitting device 2. As shown in FIG. [Figure 23] FIG. 23 shows the results of a reliability test of the light emitting device 2. As shown in FIG. [Figure 24] FIG. 24 is a graph showing the current density-radiant emittance characteristics of the light-emitting device 3. As shown in FIG. [Diagram 25] FIG. 25 is a graph showing the voltage-current density characteristics of the light-emitting device 3. As shown in FIG. [Figure 26] FIG. 26 is a graph showing the current density-radiant flux characteristics of the light-emitting device 3. As shown in FIG. [Figure 27] FIG. 27 is a graph showing the voltage-radiant emittance characteristics of the light-emitting device 3. As shown in FIG. [Figure 28] FIG. 28 is a graph showing the current density-external quantum efficiency characteristics of the light-emitting device 3. As shown in FIG. [Figure 29] FIG. 29 is a graph showing the emission spectrum of the light-emitting device 3. As shown in FIG. [Diagram 30] FIG. 30 shows the results of a reliability test on the light emitting device 3. As shown in FIG. [Diagram 31] FIG. 31 is a graph showing the angle dependence of the relative intensity of the light emitting device 3. As shown in FIG. [Diagram 32] FIG. 32 is a graph showing the angle dependence of the normalized photon intensity of the light-emitting device 3. As shown in FIG. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0041] The embodiment will be described in detail with reference to the drawings. However, the present invention is not limited to the following description. The present invention is not limited to the above embodiment, and various changes and modifications may be made in the form and details without departing from the spirit and scope of the present invention. It will be easily understood by those skilled in the art that the above-mentioned invention can be obtained by the following embodiments. It should not be construed as being limited to the contents described.

[0042] In the configuration of the invention described below, the same parts or parts having similar functions are The same reference numerals are used in common between different drawings, and the repeated explanations are omitted. When referring to a function, the hatch pattern may be the same and no particular symbol may be used.

[0043] In addition, the position, size, range, etc. of each component shown in the drawings are not necessarily the same as in the actual embodiment, in order to facilitate understanding. Therefore, the disclosed invention may not necessarily represent the position, size, range, etc. Furthermore, the present invention is not limited to the position, size, range, etc. disclosed in the drawings.

[0044] The words "membrane" and "layer" may be interchangeable depending on the situation. For example, the term "conductive layer" can be used interchangeably with the term "conductive film." ". Alternatively, for example, the term "insulating film" may be changed to It is possible to change the term to "insulating layer."

[0045] (Embodiment 1) In this embodiment, an organometallic complex of one embodiment of the present invention will be described.

[0046] [Structure of an organometallic complex according to one embodiment of the present invention] The organometallic complex according to one embodiment of the present invention is a complex having a benzoquinoxaline skeleton and an iridium central metal. The structure has a ligand having a quinoxaline or naphthoquinoxaline skeleton. One embodiment of the present invention is an organometallic complex represented by General Formula (G1). Another embodiment of the present invention is a light-emitting material represented by the general formula (G1). This is a material for light-emitting devices represented by (G1).

[0047] [ka]

[0048] In general formula (G1), R 1 ~R 11 are each independently hydrogen or a group having 1 to 6 carbon atoms. represents an alkyl group, R 1 ~R 4 At least two of the alkyl groups have 1 to 6 carbon atoms. represents a group, R 5 ~R 9 At least two of the groups represent alkyl groups having 1 to 6 carbon atoms. X represents a substituted or unsubstituted benzene ring or naphthalene ring, and n is 2 or 3. and L represents a monoanionic ligand.

[0049] In general formula (G1), X is a substituted or unsubstituted benzene ring or naphthalene ring. In other words, by condensing a benzene ring or a naphthalene ring to a quinoxaline, a π-conjugated system can be formed. Stretching the molecule, deepening its lowest unoccupied molecular orbital (LUMO) level, and making it more energetically stable. Therefore, the emission wavelength can be made longer. An organometallic complex can be obtained.

[0050] One embodiment of the present invention is an organometallic complex represented by General Formula (G2). Another embodiment of the present invention is a light-emitting material represented by the general formula (G2). This is a material for light-emitting devices represented by (G2).

[0051] [ka]

[0052] In general formula (G2), R 1 , R 3 , R 6 , and R 8 Each independently has 1 to 6 carbon atoms. R represents the alkyl group below. 10 and R 11 are each independently hydrogen or a group having one or more carbon atoms. 6 or less alkyl group, and X is a substituted or unsubstituted benzene ring or naphthalene ring. wherein n is 2 or 3, and L represents a monoanionic ligand.

[0053] In general formula (G2), X is a substituted or unsubstituted benzene ring or naphthalene ring. In other words, by condensing a benzene ring or a naphthalene ring to a quinoxaline, a π-conjugated system can be formed. The LUMO level can be stretched, deepened, and energetically stabilized, resulting in light emission. The wavelength can be increased, thus obtaining an organometallic complex that emits near-infrared light. It is possible.

[0054] R 1 , R 3 , R 6 , and R 8 is an alkyl group having 1 to 6 carbon atoms, R 1 , R 3 , R 6 , and R 8 Compared to when hydrogen is used, the sublimability of the organometallic complex is increased, and the sublimation This is preferable because it allows the temperature to be lowered. 1 , R 3 , R 6 , and R 8 are, respectively, It is preferable that R is a ethyl group. 1 , R 3 , R 6 , and R 8 All of the above are A ethyl group is preferred.

[0055] In one embodiment of the present invention, X is a substituted or unsubstituted benzene ring or naphthalene ring, and X The sublimability of the organometallic complex tends to be lower than when R is not a condensed ring. 1 , R 3 , R 6 , and R 8 Since the alkyl group has 1 to 6 carbon atoms, the organometallic complex Therefore, the sublimation property can be improved. Metal complexes can be obtained.

[0056] R 1 and R 3 However, because it is an alkyl group with 1 to 6 carbon atoms, it is bonded to iridium. This increases the dihedral angle of the benzene ring, which is the luminescence spectrometer of the organometallic complex. It is theoretically possible to reduce the second peak in the spectrum and narrow the half-width. This makes it possible to efficiently obtain light of a desired wavelength.

[0057] In the general formula (G1) and the general formula (G2), the alkyl group having 1 to 6 carbon atoms is , methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, isopropyl group, isobutyl group, tert-butyl group, pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, neopentyl group, hexyl group, isohexyl group, 3-methylpentyl group butyl group, 2-methylpentyl group, 2-ethylbutyl group, 1,2-dimethylbutyl group, 2, Examples include a 3-dimethylbutyl group.

[0058] In the general formula (G1) and the general formula (G2), the benzene ring or the naphthalene ring has a substituent. When the aryl group has a substituent, examples of the substituent include an alkyl group having 1 to 6 carbon atoms. As for the alkyl group having a number of 1 to 6, the above description can be applied.

[0059] As monoanionic ligands, monoanionic bidentate ligands having a β-diketone structure are chelate ligand, monoanionic bidentate chelating ligand with carboxyl group, phenol A monoanionic bidentate chelating ligand having a neutral hydroxyl group, both of which are nitrogen-containing ligands. A monoanionic bidentate chelating ligand that can be cyclometallated to iridium and metal- and bidentate ligands that form carbon bonds.

[0060] The monoanionic ligand is preferably any one of the general formulas (L1) to (L7). In particular, the use of a ligand represented by the general formula (L1) is preferable because it enhances the sublimability. The ligand represented by the structural formula (L8) (dipivaloyl) is an example of the ligand represented by the general formula (Ll). Methane) and ligands having a benzoquinoxaline skeleton or naphthoquinoxaline skeleton are favorably related. This is a suitable combination, and the sublimability of the organometallic complex of one embodiment of the present invention is improved, and the sublimation temperature is reduced. This is preferable because it can reduce the

[0061] [ka]

[0062] In general formulas (L1) to (L7), R 51 ~R 89 are each independently hydrogen or an optionally substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, halogeno groups, vinyl groups, substituted or unsubstituted haloalkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 6 carbon atoms, or a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, A represents an aryl group having a carbon number of 6 to 13; 1 ~A 13 are independently bonded to nitrogen and hydrogen sp 2 Hybridized carbon or substituted sp 2 represents a hybrid carbon, and the substituent has 1 carbon atom an alkyl group having 1 to 6 carbon atoms, a halogeno group, a haloalkyl group having 1 to 6 carbon atoms, or a phenyl group; It represents either one.

[0063] The maximum peak wavelength (i.e., the wavelength at which the peak intensity is the highest) of the light emitted by the organometallic complex of one embodiment of the present invention. The wavelength of the light emitted from the light source is preferably 760 nm or more and 900 nm or less. Preferably, the wavelength is 780 nm or more. Also, the wavelength is 880 nm or less. is preferred.

[0064] Specific examples of the organometallic complex according to one embodiment of the present invention include those represented by structural formulas (100) to (111). However, the present invention is not limited to these. .

[0065] [ka]

[0066] [ka]

[0067] [ka]

[0068] [ka]

[0069] [Method for synthesizing an organometallic complex according to one embodiment of the present invention] As a synthesis method for the organometallic complex of one embodiment of the present invention, various reactions can be applied. A method for synthesizing the organometallic complex represented by the general formula (G1) is illustrated below.

[0070] First, an example of a method for synthesizing an organic compound represented by general formula (G0) will be described, and then the Using an organic compound represented by general formula (G0), an organometallic complex represented by general formula (G1) is produced. Hereinafter, the method for synthesizing the compound represented by the general formula (G1) will be described. (organometallic complexes represented by general formula (G1-1)) and n in general formula (G1) is The following will be explained separately for the case 3 (organometallic complex represented by general formula (G1-2)). Note that a synthesis method for the organometallic complex of one embodiment of the present invention is not limited to the synthesis method described below.

[0071] <Example of a method for synthesizing an organic compound represented by general formula (G0)> The organic compound represented by the general formula (G0) is a type of quinoxaline derivative, and is one of the compounds of the present invention. The organic compound represented by the general formula (G0) is, for example, the organic compound shown below. Using one of the three synthetic schemes (A-1), (A-1'), and (A-1''), It can be synthesized.

[0072] [ka]

[0073] General formula (G0) and synthetic schemes (A-1), (A-1'), and (A-1'') described later ) in R 1 ~R 11 are each independently a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R represents a cyclic group; 1 ~R 4 At least two of the above groups represent alkyl groups having 1 to 6 carbon atoms. S, R 5 ~R 9 At least two of the groups represent an alkyl group having 1 to 6 carbon atoms, and X represents , a substituted or unsubstituted benzene ring or naphthalene ring.

[0074] For example, the organic compound represented by the general formula (G0) can be prepared as shown in the synthesis scheme (A-1). The halogenated benzene derivative (A1) is lithiated with an alkyl lithium or the like to give quinoxaline. The compound (A-1) can be obtained by reacting the compound (A2) with the derivative (A3). ) in Z 1 represents a halogen.

[0075] [ka]

[0076] The organic compound represented by the general formula (G0) can be prepared as shown in the synthesis scheme (A-1'). The benzene derivative boronic acid (A1') and the quinoxaline halide (A2') were reacted with In the synthesis scheme (A-1'), , Z 2 represents a halogen.

[0077] [ka]

[0078] The organic compound represented by the general formula (G0) can be synthesized as shown in the synthesis scheme (A-1''). Then, a benzene derivative-substituted diketone (A1'') is reacted with a diamine (A2'') to form the aryl group. It can be obtained by:

[0079] [ka]

[0080] The synthesis method of the organic compound represented by the general formula (G0) is not limited to the above-mentioned three synthesis methods, Other synthesis methods may also be used.

[0081] The above-mentioned compounds (A1), (A2), (A1'), (A2'), (A1''), (A2'' ) are commercially available in various types or can be synthesized, so the general formula Many kinds of organic compounds represented by (G0) can be synthesized. The organometallic complex according to one embodiment of the present invention is characterized by a wide variety of ligands. be.

[0082] <Method for synthesizing organometallic complex represented by general formula (G1-1)> Next, an example of a method for synthesizing the organometallic complex represented by general formula (G1-1) will be described. The organometallic complex represented by the general formula (G1-1) is an organometallic complex according to one embodiment of the present invention. This corresponds to the case where n in general formula (G1) is 2.

[0083] [ka]

[0084] In the general formula (G1-1) and the synthetic schemes (A-2) and (A-3) described below, R 1 ~R 11 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R 1 ~R 4 At least two of R represent an alkyl group having 1 to 6 carbon atoms. 5 ~R 9 of At least two of them represent an alkyl group having 1 to 6 carbon atoms, and X is a substituted or unsubstituted alkyl group. represents a substituted benzene ring or naphthalene ring, and L represents a monoanionic ligand.

[0085] First, as shown in the synthesis scheme (A-2), an organic compound represented by general formula (G0) and Iridium compounds containing halogens (iridium chloride, iridium bromide, iridium iodide) etc.), and solvent-free, alcohol-based solvents (glycerol, ethylene glycol, 2-methylpropanediol, etc.). Alcohols (e.g., 2-ethoxyethanol, 2-methoxyethanol, etc.) alone or in combination with one or more By using a mixed solvent of an alcohol-based solvent and water and heating in an inert gas atmosphere, The dinuclear complex represented by (B) can be obtained. The heating means is not particularly limited, and oil A bath, a sand bath, or an aluminum block may be used. It is also possible to use it as

[0086] The binuclear complex represented by the general formula (B) is an organometallic complex having a halogen-bridged structure. This is one type of dinuclear complex and is one embodiment of the present invention.

[0087] [ka]

[0088] Furthermore, as shown in the synthesis scheme (A-3), a binuclear complex represented by the general formula (B) and a mononuclear complex represented by the general formula (B) can be synthesized. By reacting with the non-anionic ligand raw material HL in an inert gas atmosphere, H The proton of L is eliminated, and L is coordinated to the central metal (Ir), to form the compound represented by the general formula (G1-1). The organometallic complex can be obtained. The heating means is not particularly limited, and may be an oil bath, sand A bath or an aluminum block may be used. Microwaves may also be used as a heating means. It is also possible.

[0089] [ka]

[0090] In the synthetic schemes (A-2) and (A-3), Z represents a halogen.

[0091] <Method for synthesizing organometallic complex represented by general formula (G1-2)> Next, an example of a method for synthesizing the organometallic complex represented by general formula (G1-2) will be described. The organometallic complex represented by the general formula (G1-2) is an organometallic complex according to one embodiment of the present invention. This corresponds to the case where n in general formula (G1) is 3.

[0092] [ka]

[0093] In the general formula (G1-2) and the synthetic scheme (A-4) described later, R 1 ~R 11 Yes, that each independently represents hydrogen or an alkyl group having 1 to 6 carbon atoms; R 1 ~R 4 A small number of At least two of the alkyl groups each having 1 to 6 carbon atoms are R 5 ~R 9 At least Two represent an alkyl group having 1 to 6 carbon atoms, and X represents a substituted or unsubstituted benzene ring. or a naphthalene ring.

[0094] The organometallic complex represented by the general formula (G1-2) can be synthesized by the following synthesis scheme (A-4): Iridium compounds containing halogens (iridium chloride hydrate, iridium bromide, iridium iodide) iridium, iridium acetate, ammonium hexachloroiridate, etc.) or organic iridium Umium complexes (acetylacetonato complexes, diethylsulfide complexes, di-μ-chloro bridged binuclear complexes) complex, di-μ-hydroxo bridged dinuclear complex, etc.) and an organic compound represented by general formula (G0): , and mixed with no solvent or with an alcohol-based solvent (glycerol, ethylene glycol, 2 2-Methoxyethanol, 2-Ethoxyethanol, etc.) and then heated. It can be obtained.

[0095] [ka]

[0096] Although the synthesis method of an organometallic complex according to one embodiment of the present invention has been described above, the present invention is not limited thereto. The present invention is not limited to this, and other synthesis methods may be used.

[0097] As described above, the organometallic complex of one embodiment of the present invention emits near-infrared light and has high sublimability; The compound is suitable as a light-emitting material that emits near-infrared light and a material for a light-emitting device. By using organic metal complexes, it is possible to increase the luminous efficiency of light-emitting devices that emit near-infrared light. In addition, by using the organometallic complex of one embodiment of the present invention, a light-emitting device that emits near-infrared light can be obtained. This can improve the reliability of the chair.

[0098] This embodiment mode can be appropriately combined with other embodiment modes. In the case where a plurality of configuration examples are shown in one embodiment, the configuration examples may be appropriately combined. It is possible to do this.

[0099] (Embodiment 2) In this embodiment, a light-emitting device according to one embodiment of the present invention and a light-emitting apparatus according to one embodiment of the present invention will be described. This will be explained with reference to FIGS. 1 to 3.

[0100] A light-emitting device according to one embodiment of the present invention includes a light-emitting organic compound in a light-emitting layer. The maximum peak wavelength (the wavelength with the highest peak intensity) of the light emitted by the organic compound is 76 0 nm or more and 900 nm or less, and preferably 780 nm or more, and more preferably 880 nm or more. It is preferable that the thickness is less than nm.

[0101] The light-emitting device according to one embodiment of the present invention can be formed in a film shape and can be easily increased in area. Therefore, it can be used as a surface light source that emits near-infrared light.

[0102] When light-emitting organic compounds emit phosphorescence, they can increase the luminous efficiency of light-emitting devices. In particular, the luminescent organic compound is preferably an organometallic compound having a metal-carbon bond. Among them, the light-emitting organic compound is preferably a cyclometal complex. It is more preferable that the luminescent organic compound is an orthometal complex. These organic compounds are preferred because they tend to emit phosphorescence, which is important for the emission of light in light-emitting devices. Therefore, the light-emitting device according to one embodiment of the present invention can emit phosphorescence. Preferably, the device is a phosphorescent device.

[0103] Furthermore, organometallic complexes with metal-carbon bonds have the following advantages over porphyrin-based compounds: Since it has high luminous efficiency and high chemical stability, it is suitable as a luminescent organic compound.

[0104] In addition, the light-emitting layer uses a light-emitting organic compound as the guest material and another organic compound as the host material. When organic compounds are used, a large valley appears in the absorption spectrum of the luminescent organic compound (intensity Depending on the excitation energy of the host material, Energy transfer to the guest material is not smooth, resulting in reduced efficiency of energy transfer. Here, in the absorption spectrum of an organometallic complex having a metal-carbon bond, the triplet MLCT (Metal to Ligand Charge Transfer) transition Absorption band, absorption band due to singlet MLCT transition, and absorption due to triplet π-π* transition Since many absorption bands overlap, it is difficult for large valleys to appear in the absorption spectrum. Therefore, it is necessary to widen the range of excitation energy values ​​of materials that can be used as host materials. This allows a wider range of host materials to be selected.

[0105] The light-emitting organic compound is preferably an iridium complex. For example, The organic compound is preferably a cyclometal complex using iridium as the central metal. Iridium complexes have higher chemical stability than platinum complexes, making them suitable for use as luminescent organic compounds. By using an iridium complex as the dopant, the reliability of the light-emitting device can be improved. From the viewpoint of stability, cyclometal complexes of iridium are preferred, and iridium ortho complexes are preferred. The trimetal complexes are more preferred.

[0106] In order to obtain near-infrared emission, the ligand in the organometallic complex is preferably a compound having 2 to 5 rings. It is preferable that the condensed heteroaromatic ring has a structure in which the condensed heteroaromatic ring is coordinated to a metal. The condensed heteroaromatic ring preferably has 4 or less rings. The more rings that are bonded, the lower the LUMO level can be, and the longer the emission wavelength of the organometallic complex. In addition, the fewer the condensed heteroaromatic rings, the higher the sublimability. Therefore, by adopting condensed heteroaromatic rings with 2 to 5 rings, the LUMO of the ligand can be increased. The level is appropriately lowered, and while maintaining high sublimability, the organic transitions derived from the (triplet) MLCT transitions are The emission wavelength of the metal complex can be extended to the near infrared. The more nitrogen atoms (N) a compound has, the lower its LUMO level can be. The number of nitrogen atoms (N) in the condensed heteroaromatic ring is preferably 2 or more, and more preferably 2. It is.

[0107] [Example of light-emitting device configuration] <Basic structure of light-emitting devices> 1A to 1C show an example of a light-emitting device having an EL layer between a pair of electrodes.

[0108] The light-emitting device shown in FIG. 1A includes an EL layer 10 between a first electrode 101 and a second electrode 102. The EL layer 103 has at least a light-emitting layer. do.

[0109] A light-emitting device may have multiple EL layers between a pair of electrodes. Two EL layers (EL layer 103a and EL layer 103b) are provided between the electrodes. A light emitting device having a tandem structure and a charge generating layer 104 is shown. The device can be driven at a low voltage and consumes less power.

[0110] When a voltage is applied between the first electrode 101 and the second electrode 102, the charge generating layer 104 generates a charge of E Electrons are injected into one of the L layer 103a and the EL layer 103b, and holes are injected into the other. Therefore, in FIG. 1B, the first electrode 101 is connected to the second electrode 102. When a voltage is applied so that the potential becomes higher than Electrons are injected into the EL layer 103b, and holes are injected into the EL layer 103b.

[0111] From the viewpoint of light extraction efficiency, the charge generating layer 104 is made to transmit near-infrared light (specifically, It is preferable that the charge generating layer 104 has a near infrared light transmittance of 40% or more. The charge generating layer 104 has a lower electrical conductivity than the first electrode 101 and the second electrode 102. also works.

[0112] FIG. 1C shows an example of a laminated structure of the EL layer 103. In this embodiment, the first electrode 10 The case where the first electrode 101 functions as an anode and the second electrode 102 functions as a cathode will be described as an example. The EL layer 103 is formed by stacking a hole injection layer 111, a hole transport layer 112, a light emitting layer 113, and a light emitting layer 114 on the first electrode 101. The light emitting layer 113, the electron transport layer 114, and the electron injection layer 115 are laminated in this order. The electron injection layer 111, the hole transport layer 112, the light emitting layer 113, the electron transport layer 114, and the electron injection layer 1 Each of the layers 15 may have a single-layer structure or a multi-layer structure. Even in the case of a tandem structure having multiple EL layers as shown in FIG. 1C, each EL layer is The same laminated structure as that of the EL layer 103 shown in FIG. 1 can be applied. If the first electrode 102 is the cathode and the second electrode 102 is the anode, the stacking order is reversed.

[0113] The light-emitting layer 113 contains a light-emitting material or a combination of a plurality of materials, and emits fluorescent light of a desired wavelength. The light-emitting layer 113 can have a structure that can emit light or phosphorescence. In this case, the luminescent materials and the like used in each of the laminated luminescent layers may be different. The other materials may be different materials. The EL layer 103a and the EL layer 103b may be configured to emit light of different wavelengths. The light-emitting material and other materials used in the light-emitting layer may be different materials.

[0114] In the light-emitting device according to one embodiment of the present invention, light emitted from the EL layer is resonated between a pair of electrodes. For example, in FIG. 1C, The first electrode 101 is a reflective electrode, and the second electrode 102 is a semi-transmissive / semi-reflective electrode (resistant to near-infrared light). By using electrodes that have both transparency and reflectivity, a micro optical resonator (microcavity) can be created. By forming the T) structure, the light emission obtained from the EL layer 103 can be intensified.

[0115] The first electrode 101 of the light-emitting device is close to a conductive film having reflectivity to near-infrared light. In the case where the reflective electrode has a laminated structure with a conductive film having infrared light transmissibility, Optical adjustment can be performed by controlling the thickness of the conductive film having optical properties. is the wavelength λ of light obtained from the light emitting layer 113, the first electrode 101 and the second electrode 1 It is preferable to adjust the distance between the electrodes of the electrode 02 to be approximately mλ / 2 (where m is a natural number). I wish.

[0116] In order to amplify the desired light (wavelength: λ) obtained from the light emitting layer 113, the first electrode the optical distance from 101 to a region (light emitting region) of the light emitting layer 113 where desired light is obtained, and the optical distance from the electrode 102 to a region (light emitting region) of the light emitting layer 113 where desired light is obtained, , are adjusted to be close to (2m'+1)λ / 4 (where m' is a natural number). The light-emitting region here is preferably a region where holes and electrons are regenerated in the light-emitting layer 113. The binding regions are indicated.

[0117] By performing such optical adjustment, the spectrum of the light obtained from the light emitting layer 113 can be narrowed. By this, light of a desired wavelength can be obtained.

[0118] However, in the above case, strictly speaking, the optical distance between the first electrode 101 and the second electrode 102 is The total thickness from the reflective area of ​​the first electrode 101 to the reflective area of ​​the second electrode 102 is called However, it is necessary to strictly define the reflection area of ​​the first electrode 101 or the second electrode 102. Since it is difficult to determine the position of the first electrode 101 and the second electrode 102, It is assumed that the above-mentioned effect can be obtained by assuming the ray domain. The optical distance between the electrode 101 and the light-emitting layer from which the desired light is obtained is, strictly speaking, 101 / 100 . The optical distance between the reflection area in the light emitting layer and the light emitting area in the light emitting layer from which the desired light is obtained is called the optical distance. However, it is possible to change the reflecting area of ​​the first electrode 101 and the emitting area that can obtain the desired light. Since it is difficult to precisely determine the light-emitting region in the optical layer, the first electrode 101 may be arbitrarily selected. The position of the light source is assumed to be the reflection region, and any position on the light-emitting layer where the desired light is obtained is assumed to be the light-emitting region. It is assumed that the above-mentioned effects can be sufficiently obtained.

[0119] At least one of the first electrode 101 and the second electrode 102 is transparent to near-infrared light. The near-infrared light transmittance of the electrode that is transparent to near-infrared light is 40% or more. In addition, when the electrode having translucency to near infrared light is the semi-transmissive / semi-reflective electrode, In this case, the reflectance of the electrode to near infrared light is 20% or more, preferably 40% or more, and It is less than 100%, preferably 95% or less, and may be 80% or less or 70% or less. For example, the reflectance of the electrode to near infrared light is 20% or more and 80% or less, preferably 40%. The resistivity of the electrode is 1×10 -2 Ωcm or less is preferable .

[0120] The first electrode 101 or the second electrode 102 is an electrode having reflectivity to near-infrared light (reflecting In the case where the reflective electrode is a reflective electrode, the reflectance of the reflective electrode to near infrared light is preferably 40% or more and 100% or less. The resistivity of this electrode is 1×10 -2 Ωcm or more Below is preferred.

[0121] <Specific structure and manufacturing method of light-emitting device> Next, the specific structure and manufacturing method of the light-emitting device will be described. The following description will be given using a light-emitting device having a single structure shown in FIG.

[0122] <First electrode and second electrode> The materials for forming the first electrode 101 and the second electrode 102 are selected from materials having the above-mentioned functions of both electrodes. If the above requirements are met, the following materials can be used in appropriate combination. For example, , metals, alloys, electrically conductive compounds, and mixtures thereof can be used as appropriate. Specifically, In-Sn oxide (also called ITO), In-Si-Sn oxide (ITSO In-Zn oxide, In-W-Zn oxide, etc. Aluminum (Al), Titanium (Ti), Chromium (Cr), Manganese (Mn), Iron (Fe), Edge Copper (Co), Nickel (Ni), Copper (Cu), Gallium (Ga), Zinc (Zn), In In, Sn, Mo, Tantalum, Tungsten (W), palladium (Pd), gold (Au), platinum (Pt), silver (Ag), yttrium ( Metals such as Cr (Y), Neodymium (Nd), and alloys containing these in appropriate combinations are used. Other elements not listed above that belong to Group 1 or Group 2 of the Periodic Table (e.g. For example, lithium (Li), cesium (Cs), calcium (Ca), strontium (S r), europium (Eu), ytterbium (Yb), and other rare earth metals, An alloy containing an appropriate combination of these, graphene, etc. can be used.

[0123] In addition, when a light emitting device having a microcavity structure is to be manufactured, the first electrode 10 The first electrode 101 is formed as a reflective electrode, and the second electrode 102 is formed as a semi-transmissive and semi-reflective electrode. Therefore, the conductive material may be used singly or in a plurality of layers to form a single layer or a multilayer structure. The second electrode 102 can be formed by selecting a material in the same manner as described above after forming the EL layer 103. In addition, these electrodes are fabricated by sputtering or vacuum deposition. It is possible.

[0124] In the light-emitting device shown in FIG. 1C, when the first electrode 101 is an anode, A hole injection layer 111 and a hole transport layer 112 are sequentially formed on the substrate 01 by vacuum deposition. .

[0125] <Hole injection layer and hole transport layer> The hole injection layer 111 is a layer that injects holes from the first electrode 101, which is an anode, to the EL layer 103. and is a layer containing a material with high hole injection properties.

[0126] Materials with high hole injection properties include molybdenum oxide, vanadium oxide, and ruthenium oxide. transition metal oxides such as tungsten oxide and manganese oxide, phthalocyanine (abbreviation: Phthalocyanine compounds such as copper(II) phthalocyanine (H2Pc) and copper(II) phthalocyanine (CuPc) Materials and the like can be used.

[0127] As a material with high hole injection properties, 4,4',4''-tris(N,N-diphenylamino) ) Triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl) (N-phenylamino)triphenylamine (abbreviation: MTDATA), 4 ,4'-Bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl DPAB, 4,4'-bis(N-{4-[N'-(3-methylphenyl)- N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTP D) 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamine N-(9-phenylcarbazol-3-yl)benzene (abbreviation: DPA3B) )-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3, 6-Bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9- Phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-( 9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: P Aromatic amine compounds such as CzPCN1) can be used.

[0128] Materials with high hole injection properties include poly(N-vinylcarbazole) (abbreviation: PVK), poly(vinylcarbazole) (abbreviation: PVK), Poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'- [4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl ) methacrylamide] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)methacrylamide] (abbreviation: PTPDMA), N,N'-bis(phenyl)benzidine (abbreviation: Poly-TPD) and the like were used. Alternatively, poly(3,4-ethylenedioxythiophene) / poly(styrene Polyaniline / Poly(styrene sulfonic acid) (abbreviation: PEDOT / PSS), It is also possible to use a polymer compound to which an acid such as (PAni / PSS) has been added.

[0129] Materials with high hole injection properties include hole transport materials and acceptor materials (electron acceptor materials). In this case, a composite material containing an acceptor material can be used. Electrons are extracted from the conductive material, generating holes in the hole injection layer 111, which then pass through the hole transport layer 112. Holes are injected into the light-emitting layer 113 through the hole-injection layer 111. The insulating layer may be formed of a single layer of a composite material containing a hole-transporting material and an acceptor material. The acceptor material may be laminated in separate layers.

[0130] The hole transport layer 112 transports holes injected from the first electrode 101 by the hole injection layer 111. The hole transport layer 112 is a layer that transports the hole to the light emitting layer 113. The hole transport layer 112 is a layer that contains a hole transport material. The hole transporting material used for the hole transport layer 112 is particularly suitable for the highest occupied molecular orbital (HOM) of the hole injection layer 111. It is preferable to use a compound having a HOMO level that is the same as or close to the HOMO level of the cation. It is nice.

[0131] The acceptor material used for the hole injection layer 111 is, for example, a material of Group 4 to Oxides of metals belonging to Group 8 can be used. Specifically, molybdenum oxide, Vanadium, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide Among them, molybdenum oxide is particularly stable in the atmosphere and has a low absorption rate. It is preferred because it has low moisture resistance and is easy to handle. Other examples include quinodimethane derivatives and chloranil derivatives. Organic acceptors such as hexaazatriphenylene derivatives can be used. As an example of a compound having an attractive group (halogen group or cyano group), 7,7,8,8-tetracyano -2,3,5,6-Tetrafluoroquinodimethane (abbreviation: F4-TCNQ), Chloranil , 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaaza Triphenylene (abbreviation: HAT-CN), 1,3,4,5,7,8-hexafluorotetrafluoroethylene Examples include aryl naphthoquinodimethane (abbreviation: F6-TCNNQ). In the case of HAT-CN, an electron-withdrawing group is bonded to a condensed aromatic ring having multiple heteroatoms. The compound is preferably thermally stable. In addition, the compound may be a halogen atom such as an electron-withdrawing group (especially a halogen atom such as a fluoro group). Radialene derivatives that have a phenyl or cyano group are preferred because of their high electron-accepting properties. Preferably, specifically, α,α',α''-1,2,3-cyclopropane triylidene tris [4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α', α''-1,2,3-Cyclopropanetriylidenetris[2,6-dichloro-3,5- Difluoro-4-(trifluoromethyl)benzeneacetonitrile], α,α',α'' -1,2,3-cyclopropanetriylidenetris[2,3,4,5,6-pentafluoro Examples include benzeneacetonitrile.

[0132] The hole transport material used in the hole injection layer 111 and the hole transport layer 112 is 10 -6 cm 2 A material having a hole mobility of 1 / Vs or more is preferable. Other substances may also be used as long as they are suitable.

[0133] As the hole transport material, π-electron-rich heteroaromatic compounds (e.g., carbazole derivatives, Thiophene derivatives, furan derivatives, etc.) and aromatic amines (compounds with an aromatic amine skeleton) Materials having high hole transport properties such as ZnO, Fe, and Cu are preferred.

[0134] Carbazole derivatives (compounds having a carbazole skeleton) include bicarbazole derivatives. (e.g., 3,3'-bicarbazole derivatives), aromatic amines having a carbazolyl group etc.

[0135] Specific examples of bicarbazole derivatives (e.g., 3,3'-bicarbazole derivatives) include 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 9,9 '-Bis(1,1'-biphenyl-4-yl)-3,3'-bi-9H-carbazole, 9 ,9'-Bis(1,1'-biphenyl-3-yl)-3,3'-bi-9H-carbazole , 9-(1,1'-biphenyl-3-yl)-9'-(1,1'-biphenyl-4-yl )-9H,9'H-3,3'-bicarbazole (abbreviation: mBPCCBP), 9-(2-naphthalene β-N-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: βNCC P) and others.

[0136] Specific examples of aromatic amines having a carbazolyl group include 4-phenyl-4'-(9 -phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1B P), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl )-9-phenyl-9H-carbazol-3-amine (abbreviation: PCBiF), N-(1, 1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3- PCBB iF), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazole-3-yl 1-naphthyl)-4'-( 9-Phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAN) B) 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazole- 3-yl)triphenylamine (abbreviation: PCBNBB), 4-phenyldiphenyl-(9 -phenyl-9H-carbazol-3-yl)amine (abbreviation: PCA1BP), N,N' -Bis(9-phenylcarbazol-3-yl)-N,N'-diphenylbenzene-1, 3-Diamine (abbreviation: PCA2B), N,N',N''-triphenyl-N,N',N' '-Tris(9-phenylcarbazol-3-yl)benzene-1,3,5-triamine (abbreviation: PCA3B), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl- 9H-Carbazol-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF ), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl [R]spiro-9,9'-bifluorene-2-amine (abbreviation: PCBASF), PCzPC A1, PCzPCA2, PCzPCN1, 3-[N-(4-diphenylaminophenyl) -N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA1), 3,6 -Bis[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenyl Carbazole (abbreviation: PCzDPA2), 3,6-bis[N-(4-diphenylamino phenyl)-N-(1-naphthyl)amino]-9-phenylcarbazole (abbreviation: PCzT PN2), 2-[N-(9-phenylcarbazol-3-yl)-N-phenylamino] Spiro-9,9'-bifluorene (abbreviation: PCASF), N-[4-(9H-carbazolyl) [4-phenyl-9-ylphenyl]-N-(4-phenyl)phenylaniline (abbreviation: YGA1B P), N,N'-bis[4-(carbazol-9-yl)phenyl]-N,N'-diphenyl Nyl-9,9-dimethylfluorene-2,7-diamine (abbreviation: YGA2F), 4,4' ,4''-Tris(carbazol-9-yl)triphenylamine (abbreviation: TCTA) Some examples include:

[0137] In addition to the above, the carbazole derivatives include 3-[4-(9-phenanthryl)- 3-[4-(1-naphthyl]-9-phenyl-9H-carbazole (abbreviation: PCPPn), 1,3-phenyl)-9-phenyl-9H-carbazole (abbreviation: PCPN), -Bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl) Biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9- Phenylcarbazole (abbreviation: CzTP), 1,3,5-tris[4-(N-carbazolyl 9-[4-(10-phenyl-9-anthrenyl)phenyl]benzene (abbreviation: TCPB), racenyl)phenyl]-9H-carbazole (abbreviation: CzPA), and the like.

[0138] Thiophene derivatives (compounds having a thiophene skeleton) and furan derivatives (compounds having a furan skeleton) Specifically, the compound that yl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl- 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene DBTFLP-III, 4-[4-(9-phenyl-9H-fluorene-9 -yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV) Which compound has a thiophene skeleton, 4,4',4''-(benzene-1,3,5-trimethylphenyl) 4-{3-[3-(9-furanyl)tri(dibenzofuran)(abbreviation: DBF3P-II) mphenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mDBFFLBi-II) etc.

[0139] Specific examples of aromatic amines include 4,4'-bis[N-(1-naphthyl)-N-phenyl]amine. N,N'-bis(3-methylamino)biphenyl (abbreviation: NPB or α-NPD), N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl )-N-phenylamino]biphenyl (abbreviation: BSPB), 4-phenyl-4'-(9- Phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl mBP AFLP), N-(9,9-dimethyl-9H-fluoren-2-yl)-N-{9,9- Dimethyl-2-[N'-phenyl-N'-(9,9-dimethyl-9H-fluorene-2- yl)amino]-9H-fluoren-7-yl}phenylamine (abbreviation: DFLADFL ), N-(9,9-dimethyl-2-diphenylamino-9H-fluoren-7-yl)di Phenylamine (abbreviation: DPNF), 2-[N-(4-diphenylaminophenyl)-N -phenylamino]spiro-9,9'-bifluorene (abbreviation: DPASF), 2,7-bi 9,9'-[N-(4-diphenylaminophenyl)-N-phenylamino]spiro Bifluorene (abbreviation: DPA2SF), 4,4',4''-tris[N-(1-naphthyl )-N-phenylamino]triphenylamine (abbreviation: 1'-TNATA), TDATA , m-MTDATA, N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenyl Examples include diamine (abbreviation: DTDPPA), DPAB, DNTPD, and DPA3B. do.

[0140] Hole transport materials include PVK, PVTPA, PTPDMA, and Poly-TPD. Polymeric compounds can also be used.

[0141] The hole transport material is not limited to the above, and may be one or a combination of various known materials. In combination, they can be used for the hole injection layer 111 and the hole transport layer 112 .

[0142] In the light-emitting device shown in FIG. 1C, a light-emitting layer 113 is formed on a hole-transporting layer 112 by vacuum deposition. is formed.

[0143] <Light-emitting layer> The light-emitting layer 113 is a layer containing a light-emitting substance.

[0144] The light-emitting device according to one embodiment of the present invention includes a light-emitting organic compound as a light-emitting substance. The light-emitting organic compound emits near-infrared light. The maximum peak wavelength is greater than 780 nm and less than or equal to 900 nm.

[0145] As the light-emitting organic compound, for example, the organometallic complex shown in Embodiment 1 can be used. In addition, the organometallic complex shown in the examples described later can be used as the luminescent organic compound. It is also possible.

[0146] Light-emitting layer 113 can have one or more light-emitting materials.

[0147] The light-emitting layer 113 contains one or more organic compounds (homogeneous compounds) in addition to the light-emitting substance (guest material). The organic compound may include one or more organic compounds. The hole transporting material and / or the electron transporting material described in this embodiment may be used. In addition, a bipolar material can be used as one or more organic compounds. This is also fine.

[0148] The light-emitting material that can be used in the light-emitting layer 113 is not particularly limited, and may be any material having a singlet excitation energy. A luminescent material that converts the energy of triplet excitation into light in the near infrared region, or a luminescent material that converts the energy of triplet excitation into light in the near infrared region. A luminescent material can be used that changes the light emitted in the region.

[0149] Luminescent materials that convert singlet excitation energy into light include fluorescent materials. Examples of such derivatives include pyrene derivatives, anthracene derivatives, triphenylene derivatives, and fluoro derivatives. Oleno derivatives, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives , dibenzoquinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives derivatives, phenanthrene derivatives, naphthalene derivatives, etc.

[0150] Examples of luminescent materials that convert triplet excitation energy into luminescence include phosphorescent materials ( Thermally activated delayed fluorescence (TDF) and thermally activated delayed fluorescence (TDF) Examples of such materials include TADF (transduced delayed fluorescence).

[0151] Examples of phosphorescent materials include 4H-triazole skeletons, 1H-triazole skeletons, imidazoline skeletons, and Organometallic complexes having a zole skeleton, a pyrimidine skeleton, a pyrazine skeleton, or a pyridine skeleton (especially iridium complexes), and the use of phenylpyridine derivatives with electron-withdrawing groups as ligands. Examples of the complex include organometallic complexes (particularly iridium complexes), platinum complexes, and rare earth metal complexes.

[0152] In addition, the light-emitting device according to one embodiment of the present invention may include a light-emitting substance other than the light-emitting substance that emits near-infrared light. The light-emitting device according to one embodiment of the present invention may include, for example, a light-emitting material that emits near-infrared light. In addition, the light-emitting element may have a light-emitting substance that emits visible light (red, blue, green, etc.).

[0153] The organic compounds (host materials, assist materials, etc.) used in the light-emitting layer 113 are light-emitting materials. One or more substances with a larger energy gap than the It can be used selectively.

[0154] When the luminescent material used in the luminescent layer 113 is a fluorescent material, the active material used in combination with the luminescent material As an organic compound, the energy level of the singlet excited state is large, and the energy level of the triplet excited state is large. It is preferable to use an organic compound having a low Gamma level.

[0155] Although some of the above specific examples overlap, preferred combinations with luminescent materials (fluorescent materials, phosphorescent materials) From this viewpoint, specific examples of organic compounds are shown below.

[0156] When the luminescent material is a fluorescent material, an organic compound that can be used in combination with the luminescent material Examples include anthracene derivatives, tetracene derivatives, phenanthrene derivatives, and pyrene derivatives. These include condensed polycyclic aromatic compounds such as chrysene derivatives, dibenzo[g,p]chrysene derivatives, etc. Can be obtained.

[0157] A specific example of an organic compound (host material) used in combination with a fluorescent material is 9-phenylene. 3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole ( Abbreviation: PCzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthracene DPCzPA, PCPN, 9,10-diphenyl Phenylanthracene (abbreviation: DPAnth), N,N-diphenyl-9-[4-(10 -phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: C zA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: D PhPA), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-azolyl) N,9-diphenyl-N-[4- (10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation Name: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-an Tolyl)phenyl]phenyl}-9H-carbazol-3-amine (abbreviation: PCAPBA ), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-cal 2PCAPA (abbreviation: 2PCAPA), 6,12-dimethoxy-5,11-difluoro phenylchrysene, N,N,N',N',N'',N'',N''',N'''-octave Phenyldibenzo[g,p]chrysene-2,7,10,15-tetraamine (abbreviation: DBC 1), CzPA, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-di Benzo[c,g]carbazole (abbreviation: cgDBCzPA), 6-[3-(9,10-di Phenyl-2-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviation Name: 2mBnfPPA), 9-phenyl-10-{4-(9-phenyl-9H-fluorene 9,10-phenyl-4'-yl}biphenyl-4'-yl}anthracene (abbreviation: FLPPA), -Bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di (2-Naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di (2-Naphthyl)anthracene (abbreviation: t-BuDNA), 9,9'-bianthryl (abbreviation BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviation :DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviation: DPNS2), 1,3,5-tri(1-pyrenyl)benzene (abbreviation: TPB3), 5,1 2-Diphenyltetracene, 5,12-bis(biphenyl-2-yl)tetracene, etc. Some examples include:

[0158] When the luminescent substance is a phosphorescent material, the organic compound used in combination with the luminescent substance is The triplet excitation energy of the optical substance (energy difference between the ground state and the triplet excited state) is three times higher than that of the optical substance. An organic compound with high doublet excitation energy may be selected.

[0159] A plurality of organic compounds (e.g., a first host material and a second host material) are reacted to form an exciplex. When using a light-emitting material in combination with a support material (or assist material, etc.), It is preferred to use a mixture of a plurality of organic compounds with a phosphorescent material (particularly an organometallic complex).

[0160] With this structure, the energy transfer from the exciplex to the luminescent material, Ex Using TET (Exciplex-Triplet Energy Transfer) In addition, the combination of multiple organic compounds can be used as the excitation light source. It is preferable to use a compound that easily forms an electron-emitting complex and that easily receives holes (hole transport material). It is particularly preferable to combine the compound with a compound that easily accepts electrons (electron transporting material). Specific examples of the hole transporting material and the electron transporting material are the same as those described in this embodiment. This configuration allows the light-emitting device to simultaneously achieve high efficiency, low voltage, and long life. It can be achieved at some point.

[0161] Organic compounds that can be used in combination with the luminescent material when the luminescent material is a phosphorescent material Examples of the amines include aromatic amines, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, and the like. Orchid derivatives, zinc and aluminum metal complexes, oxadiazole derivatives, triazoles Derivatives, benzimidazole derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives , pyrimidine derivatives, triazine derivatives, pyridine derivatives, bipyridine derivatives, phenanthone thoroline derivatives and the like.

[0162] Among the above, aromatic amines (aromatic amine skeletons) which are organic compounds with high hole transport properties Compounds having the formula (I), carbazole derivatives, dibenzothiophene derivatives (thiophene derivatives ) and specific examples of dibenzofuran derivatives (furan derivatives) include the above-mentioned hole transporting The same specific examples of materials as those mentioned above can be mentioned.

[0163] Specific examples of zinc and aluminum metal complexes, which are organic compounds with high electron transport properties, include , tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4- Methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq3), bis(10 -Hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis (2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), etc. Examples of the metal complex include a metal complex having a quinoline skeleton or a benzoquinoline skeleton.

[0164] In addition, bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: Zn PBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: Zn Metal complexes with oxazole or thiazole ligands such as BTZ can also be used. can be done.

[0165] Oxadiazole derivatives, triazole derivatives, and benzaldehyde derivatives, which are organic compounds with high electron transport properties, Benzoimidazole derivatives, benzimidazole derivatives, quinoxaline derivatives, dibenzoxazole Specific examples of the noxaline derivatives and phenanthroline derivatives include 2-(4-biphenylyl )-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: P BD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazine Azole-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1, 3,4-Oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviation: CO1 1), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl) )-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl )-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazo p-EtTAZ, 2,2',2''-(1,3,5-benzenetriyl) Tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(diphenyl Benzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole ( Abbreviation: mDBTBIm-II), 4,4'-bis(5-methylbenzoxazole-2- yl)stilbene (abbreviation: BzOs), bathophenanthroline (abbreviation: Bphen), Cuproin (abbreviation: BCP), 2,9-bis(naphthalene-2-yl)-4,7-difluoro phenyl-1,10-phenanthroline (abbreviation: NBphen), 2-[3-(dibenzothiophene 2mDibenzo[f,h]quinoxaline (abbreviation: 2mDBTP DBq-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl ]Dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3' -(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinox Sarin (abbreviation: 2mCzBPDBq), 2-[4-(3,6-diphenyl-9H-carba 2CzPDBq -III), 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h ]quinoxaline (abbreviation: 7mDBTPDBq-II) and 6-[3-(dibenzothiophene 6m-4-phenyl)dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDB q-II).

[0166] Heterocyclic compounds with diazine skeletons and triazine skeletons, which are organic compounds with high electron transport properties, Specific examples of heterocyclic compounds having a pyridine skeleton include 4,6 -Bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPn P2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation : 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazole-9-yl) 4,6mCzP2Pm, 2-{4-[3-(N-phenyl)phenyl]pyrimidine phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl} -4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 9-[3 -(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl mPCCzPTzn-02, 3,5 -Bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCz PPy), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmP yPB) etc.

[0167] As an organic compound with high electron transport properties, poly(2,5-pyridinediyl) (abbreviation: PPy ), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3 ,5-diyl)] (abbreviation: PF-Py), poly[(9,9-dioctylfluorene-2, 7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-B Polymers such as .Py can also be used.

[0168] TADF materials are materials that convert triplet excited states into singlet excited states using a small amount of thermal energy. It is possible to convert the light into a singlet state (reverse intersystem crossing), and efficiently emit light (fluorescence) from the singlet excited state. The conditions for efficiently obtaining thermally activated delayed fluorescence are as follows: The energy difference between the doublet excitation level and the singlet excitation level is 0 eV or more and 0.2 eV or less, preferably In addition, the delayed fluorescence in TADF materials is The light is an emission that has a spectrum similar to that of normal fluorescence, but has a significantly longer lifespan. The lifespan of -6 seconds or more, preferably 10 -3 More than seconds.

[0169] Examples of TADF materials include fullerenes and their derivatives, and acridines such as proflavine. Derivatives, eosin, etc. Also, magnesium (Mg), zinc (Zn), cadmium (Cd) Cd, Sn, Pt, In, or Palladium Examples of metal-containing porphyrins include those containing Pd. For example, protoporphyrin-tin fluoride complex (abbreviation: SnF2(Proto IX)) , mesoporphyrin-tin fluoride complex (abbreviation: SnF2(Meso IX)), hematopoietin Lufirin-Tin Fluoride Complex (abbreviation: SnF2 (Hemato IX)), Coproporf Fluorine tetramethyl ester-tin fluoride complex (abbreviation: SnF2(Copro III- 4Me), Octaethylporphyrin-Tin Fluoride Complex (abbreviation: SnF2(OEP)) , etioporphyrin-tin fluoride complex (abbreviation: SnF2(Etio I)), octaethylene Examples include thylporphyrin-platinum chloride complex (abbreviation: PtCl2OEP).

[0170] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[ 2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-T RZ), PCCzPTzn, 2-[4-(10H-phenoxazin-10-yl)phenyl 3,6-diphenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[ 4-(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5 -Diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9- Dimethyl-9H-acridin-10-yl)-9H-xanthen-9-one (abbreviation: AC RXTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl ]sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10'H-spiro[ Acridine-9,9'-anthracene]-10'-one (abbreviation: ACRSA), etc. Heterocyclic compounds having a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring can be used. In addition, substances in which a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring are directly bonded are The donor properties of the π-electron rich heteroaromatic ring and the acceptor properties of the π-electron deficient heteroaromatic ring are both This is particularly preferred because it makes the energy difference between the singlet excited state and the triplet excited state smaller. It is nice.

[0171] In addition, when using a TADF material, it can also be used in combination with other organic compounds. In particular, it can be combined with the host material, hole transport material, and electron transport material described above.

[0172] In addition, the above materials can be used in combination with low molecular weight materials or high molecular weight materials to form the light emitting layer 113. The film can be formed by a known method (such as vapor deposition, coating, or printing). ) can be used as appropriate.

[0173] In the light-emitting device shown in FIG. 1C, an electron-transporting layer 114 is formed on light-emitting layer 113 .

[0174] <Electron transport layer> The electron transport layer 114 is formed by transporting electrons injected from the second electrode 102 through the electron injection layer 115. The electron transport layer 114 is a layer that transports electrons to the light emitting layer 113. The electron transport material used in the electron transport layer 114 is 1×10 -6 cm 2 / Vs or more It is preferable that the material has an electron mobility of 100 nm or more. Other materials may also be used.

[0175] As the electron transporting material, there are metal complexes having a quinoline skeleton, Metal complexes, metal complexes having an oxazole skeleton, metal complexes having a thiazole skeleton, etc. , oxadiazole derivatives, triazole derivatives, imidazole derivatives, oxazole derivatives Conductors, thiazole derivatives, phenanthroline derivatives, quinoline derivatives with quinoline ligands Conductors, benzoquinoline derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, pyrimidine These include aryl, bipyridine, pyrimidine, and other nitrogen-containing heteroaromatic compounds. For example, a material having a high electron transporting property, such as a π-electron deficient heteroaromatic compound, can be used.

[0176] As specific examples of the electron transporting material, the materials listed above can be used.

[0177] Next, in the light-emitting device shown in FIG. 1C, an electron injection layer 115 is formed on the electron transport layer 114. It is formed by vacuum deposition.

[0178] <Electron injection layer> The electron injection layer 115 is a layer containing a substance with high electron injection properties. Lithium fluoride (LiF), Cesium fluoride (CsF), Calcium fluoride (CaF2), Lithium oxide (LiO x ) and the like, alkali metals, alkaline earth metals, or Compounds of the formula: In addition, an electride may be used for the electron injection layer 115. For example, an electride is a mixture of calcium and aluminum oxide with electrons added. In addition, the above-mentioned material constituting the electron transport layer 114 may be a material containing a high concentration of the above-mentioned It can also be used.

[0179] The electron injection layer 115 contains an electron transport material and a donor material (electron donor material). Composite materials may also be used. Such composite materials are made by adding electrons to organic compounds by electron donors. Since the organic compound is It is preferable that the material is excellent in transporting the generated electrons. Specifically, for example, The electron transporting material (metal complex, heteroaromatic compound, etc.) used for the electron transport layer 114 is The electron donor can 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, Examples include cesium, magnesium, calcium, erbium, and ytterbium. In addition, alkali metal oxides and alkaline earth metal oxides are preferred, and lithium oxide, calcium oxide, etc. Examples of the oxides include ammonium oxide and barium oxide. Lewis salts such as magnesium oxide are also included. In addition, organic compounds such as tetrathiafulvalene (TTF) can be used. can also be used.

[0180] <Charge generation layer> In the light-emitting device shown in FIG. 1B, the charge generating layer 104 is connected to the first electrode 101 (anode). When a voltage is applied between the second electrode 102 (cathode) and the EL layer 103a, electrons are injected into the EL layer 103a. It also has a function of injecting holes into the EL layer 103b.

[0181] The charge generating layer 104 contains a hole transporting material and an acceptor material (electron accepting material). The composition may be a composition including an electron transport material and a donor material. By forming the charge generating layer 104 having such a configuration, it is possible to improve the driving efficiency when the EL layer is laminated. The voltage rise can be suppressed.

[0182] The hole transport material, the acceptor material, the electron transport material, and the donor material are The materials mentioned above can be used.

[0183] Note that the light-emitting device shown in this embodiment mode can be manufactured by a vacuum process such as an evaporation method or a spin Solution processes such as the ink-jet method and the deposition method can be used. In this case, sputtering, ion plating, ion beam deposition, and molecular beam deposition are used. , physical vapor deposition (PVD) method such as vacuum deposition method, chemical vapor deposition (CVD) method, etc. In particular, the functional layers included in the EL layer (hole injection layer, hole transport layer, light-emitting layer, electron transport layer , electron injection layer) and charge generation layer are formed by deposition (vacuum deposition, etc.), coating (dip coating method, die coating method, bar coating method, spin coating method, spray coating method, etc.), printing method (inkjet method, screen (stencil printing) method, offset (lithographic printing) method, flex It can be formed by a method such as letterpress printing, gravure printing, microcontact printing, etc. This can be done.

[0184] The materials of the functional layer and the charge generating layer constituting the EL layer 103 are not limited to the above-mentioned materials. For example, polymer compounds (oligomers, dendrimers, polymers) can be used as materials for the functional layer. mers, etc.), medium molecular weight compounds (compounds in the intermediate range between low molecular weight and high molecular weight: molecular weight 400 to 400 0), inorganic compounds (quantum dot materials, etc.), etc. may also be used. colloidal quantum dot materials, alloy quantum dot materials, core-shell quantum dot materials , core-type quantum dot materials, etc. can be used.

[0185] [Light emitting device configuration example 1] FIG. 2A shows a top view of the light emitting device, and FIGS. 2B and 2C show the area between the dashed dotted line X1-Y1 and 2A to 2C are cross-sectional views taken along the line X2-Y2. The light-emitting device shown in FIG. 2A to FIG. 2C is used in, for example, a lighting device. The light emitting device can be a bottom emission, a top emission, a dual emission, The emission may be either.

[0186] The light emitting device shown in FIG. 2B includes a substrate 490a, a substrate 490b, a conductive layer 406, a conductive layer 416, Insulating layer 405, organic EL device 450 (first electrode 401, EL layer 402, and second The organic EL device 450 includes a light-emitting element, an organic The EL layer 402 may be called an EL element, a light-emitting device, etc. As the organic compound, the organometallic complex described in Embodiment 1 is preferably used.

[0187] The organic EL device 450 includes a first electrode 401 on a substrate 490a and a The EL layer 402 and the second electrode 403 on the EL layer 402. Organic EL device 450 is encapsulated by layer 407 and substrate 490b.

[0188] The ends of the first electrode 401 , the conductive layer 406 , and the conductive layer 416 are covered with an insulating layer 405 . The conductive layer 406 is electrically connected to the first electrode 401, and the conductive layer 416 is electrically connected to the second electrode 403. The conductive layer 406 covered with the insulating layer 405 via the first electrode 401 is It functions as an auxiliary wiring and is electrically connected to the first electrode 401. Organic EL device 450 By providing auxiliary wiring electrically connecting the electrodes, the voltage drop caused by the resistance of the electrodes can be suppressed. The conductive layer 406 may be provided on the first electrode 401. In addition, an auxiliary wiring electrically connected to the second electrode 403 may be provided on the insulating layer 405 or the like. good.

[0189] The substrate 490a and the substrate 490b are made of glass, quartz, ceramic, or sapphire, respectively. The substrate 490a and the substrate 490b may be flexible. The material allows for increased flexibility of the display device.

[0190] The light-emitting surface of the light-emitting device is equipped with a light extraction structure to increase the light extraction efficiency and a structure to prevent dust from adhering. Antistatic film that prevents adhesion of dirt, water-repellent film that prevents scratches caused by use A hard coat film, an impact absorbing layer, etc. may be disposed.

[0191] Examples of insulating materials that can be used for the insulating layer 405 include acrylic resin and epoxy. Resins such as resins, silicon oxide, silicon oxynitride, silicon nitride oxide, silicon nitride, Examples of the insulating material include inorganic insulating materials such as aluminum oxide.

[0192] The adhesive layer 407 may be a photo-curable adhesive such as an ultraviolet-curable adhesive, a reaction-curable adhesive, or a heat-curable adhesive. Various curing adhesives such as adhesives, anaerobic adhesives, etc. can be used. The following resins are available: epoxy resin, acrylic resin, silicone resin, phenolic resin, polyimide resin, Imide resin, PVC (polyvinyl chloride) resin, PVB (polyvinyl butyral) resin Examples of the resin include ethylene vinyl acetate (EVA) resin. In particular, the permeability of epoxy resin and the like is improved. A material with low wettability is preferable. A two-part mixed resin may also be used. etc. may also be used.

[0193] The light emitting device shown in FIG. 2C includes a barrier layer 490c, a conductive layer 406, a conductive layer 416, and an insulating layer 40 5, an organic EL device 450, an adhesive layer 407, a barrier layer 423, and a substrate 490b. do.

[0194] The barrier layer 490c shown in FIG. 2C is made of a substrate 420, an adhesive layer 422, and a highly insulating It has a layer 424.

[0195] In the light-emitting device shown in FIG. 2C, a conductive layer is provided between the insulating layer 424 having a high barrier property and the barrier layer 423. The organic EL device 450 is disposed on the substrate 420. Even if a resin film with relatively low waterproofing is used, impurities such as water may enter the OLED device. It is possible to suppress a decrease in the life span due to the embedding.

[0196] The substrate 420 and the substrate 490b are each made of, for example, polyethylene terephthalate (P Polyester resins such as polyethylene naphthalate (PEN), polyacrylonitrile resin, acrylic resin, polyimide resin, polymethyl methacrylate resin, polycarbonate Polyethersulfone (PC) resin, Polyethersulfone (PES) resin, Polyamide resin (nylon , aramid, etc.), polysiloxane resin, cycloolefin resin, polystyrene resin, poly Amide-imide resin, polyurethane resin, polyvinyl chloride resin, polyvinylidene chloride resin, Polypropylene resin, polytetrafluoroethylene (PTFE) resin, ABS resin, cell The substrate 420 and the substrate 490b may be made of a flexible material. Alternatively, glass having a thickness sufficient to provide the desired properties may be used.

[0197] The insulating layer 424 having high barrier properties is preferably an inorganic insulating film. Examples of the thin film include a silicon nitride film, a silicon oxynitride film, a silicon oxide film, and a silicon oxynitride film. A silicon film, an aluminum oxide film, an aluminum nitride film, etc. can be used. Hafnium oxide film, yttrium oxide film, zirconium oxide film, gallium oxide film, tantalum oxide film tantalum film, magnesium oxide film, lanthanum oxide film, cerium oxide film, and neodymium oxide film The insulating film may be a laminate of two or more of the above insulating films.

[0198] The barrier layer 423 preferably has at least one inorganic film. The layer 423 may have a single layer structure of an inorganic film or a laminate structure of an inorganic film and an organic film. As the inorganic film, the above-mentioned inorganic insulating film is suitable. As the laminated structure, for example, A silicon nitride film, a silicon oxide film, an organic film, a silicon oxide film, and a silicon nitride film. The protective layer may have a laminated structure of an inorganic film and an organic film. This removes impurities (typically hydrogen, water, etc.) that may enter the organic EL device 450. It can be suitably suppressed.

[0199] The insulating layer 424 with high barrier properties and the organic EL device 450 are mounted on a flexible substrate 420. In this case, the adhesive layer 422 is not necessary. The organic EL device 450 is formed on a hard substrate via a release layer, and then the substrate 42 is For example, the peeling layer can be transformed into a 0 state by applying heat, force, laser light, etc. After the insulating layer 424 and the organic EL device 450 are peeled off from the hard substrate, the adhesive layer 422 is The substrate 420 may be attached to the film 420 using a peeling layer. For example, the insulating film may be a laminated structure of inorganic films including a tungsten film and a silicon oxide film, or a polyimide film. In the case of using a hard substrate, compared to a resin substrate, etc., an organic resin film, etc. can be used. Since the insulating layer 424 can be formed at high temperatures, the insulating layer 424 can be made dense and extremely It is possible to provide an insulating film with high barrier properties.

[0200] [Light-emitting device configuration example 2] The light-emitting device according to one embodiment of the present invention is a passive matrix type or an active matrix type. An active matrix light emitting device will be described with reference to FIG.

[0201] FIG. 3A shows a top view of the light-emitting device. FIG. 3B shows a cross-sectional view taken along the dashed line A-A' shown in FIG. It is.

[0202] The active matrix type light emitting device shown in FIG. 3A and FIG. 3B includes a pixel section 302, a circuit section 303, and a light emitting device shown in FIG. 3, circuit portion 304a, and circuit portion 304b.

[0203] The circuit portion 303, the circuit portion 304a, and the circuit portion 304b are each a scanning line driving circuit (gate The pixel circuit can function as a gate driver (signal line driver) or a signal line driver circuit (source driver). Alternatively, an external gate driver or source driver and the pixel section 302 are electrically connected to each other. It may also be a circuit for connecting.

[0204] A lead wiring 307 is provided on the first substrate 301. The lead wiring 307 is The FPC 308 is electrically connected to the circuit unit 303, which is a part input terminal. The circuit unit 304a and the circuit unit 304b receive signals from the outside (for example, a video signal, a clock The FPC308 also has a pre-connected The configuration shown in FIG. 3A and FIG. 3B may be a laser printer. It can also be called a light emitting module having an optical device (or light emitting apparatus) and an FPC.

[0205] The pixel section 302 includes an organic EL device 317, a transistor 311, and a transistor 31 The transistor 312 has an organic EL device 317. The transistor 311 is electrically connected to a first electrode 313 that is a switching The transistor 312 functions as a current control transistor. The number of transistors in each pixel is not particularly limited, and may be increased as necessary. It can be set appropriately according to the situation.

[0206] The circuit section 303 includes a plurality of transistors including a transistor 309, a transistor 310, etc. The circuit section 303 has a transistor of a single polarity (either N-type or P-type). The circuit may be formed of a transistor including an N-type transistor and a P-type transistor. The pixel may be formed of a CMOS circuit or may have an external driver circuit.

[0207] The structure of a transistor included in the light-emitting device of this embodiment is not particularly limited. Uses transistors of the same type, staggered type, inverted staggered type, etc. In addition, the present invention can be applied to any of the top-gate and bottom-gate transistor structures. Alternatively, gates may be provided above and below the semiconductor layer in which the channel is formed. Good too.

[0208] The crystallinity of the semiconductor material used in the transistor is not particularly limited. A semiconductor having crystallinity (microcrystalline semiconductor, polycrystalline semiconductor, single crystal semiconductor, or semiconductor with partially crystalline regions) If a semiconductor having crystallinity is used, the This is preferable because it is possible to suppress deterioration of the resistor characteristics.

[0209] The semiconductor layer of the transistor preferably contains a metal oxide (also called an oxide semiconductor). Alternatively, the semiconductor layer of the transistor may include silicon. is amorphous silicon, crystalline silicon (low-temperature polysilicon, single crystal silicon, etc.) ) etc.

[0210] The semiconductor layer may be, for example, a combination of indium and M (where M is gallium, aluminum, silicon, or phosphide). Uranium, yttrium, tin, copper, vanadium, beryllium, titanium, iron, nickel, gel Manium, zirconium, molybdenum, lanthanum, cerium, neodymium, hafnium, tantalum one or more selected from the group consisting of tantalum, tungsten, and magnesium; zinc; In particular, M is aluminum, gallium, yttrium, and sulphur. It is preferable that the polysaccharide is one or more selected from the above.

[0211] In particular, the semiconductor layer contains indium (In), gallium (Ga), and zinc (Zn). It is preferable to use IGZO (intermetallic oxide).

[0212] When the semiconductor layer is an In-M-Zn oxide, a film of the In-M-Zn oxide is formed. In the sputtering target, the atomic ratio of In is preferably equal to or greater than the atomic ratio of M. The atomic ratio of the metal elements in such a sputtering target is In:M:Zn= 1:1:1, In:M:Zn=1:1:1.2, In:M:Zn=2:1:3, In:M :Zn=3:1:2, In:M:Zn=4:2:3, In:M:Zn=4:2:4.1, In:M:Zn=5:1:6, In:M:Zn=5:1:7, In:M:Zn=5:1: 8, In:M:Zn=6:1:6, In:M:Zn=5:2:5, etc.

[0213] The transistors included in the circuit portion 303, the circuit portion 304a, and the circuit portion 304b, and the pixel portion 302 The transistors in the circuit section may have the same structure or different structures. The structures of the transistors in the circuit portion 303, the circuit portion 304a, and the circuit portion 304b are all the same. Similarly, the pixel unit 302 may have a plurality of transistors. The transistors may all have the same structure, or there may be two or more types.

[0214] The end of the first electrode 313 is covered with an insulating layer 314. , negative photosensitive resin, positive photosensitive resin (acrylic resin), and other organic compounds, Inorganic compounds such as silicon, silicon oxynitride, and silicon nitride can be used. The layer 314 preferably has a curved surface at the upper or lower end. This allows the film formed on the insulating layer 314 to have good coverage.

[0215] An EL layer 315 is provided on the first electrode 313, and a second electrode 316 is provided on the EL layer 315. The EL layer 315 includes a light-emitting layer, a hole-injecting layer, a hole-transporting layer, an electron-transporting layer, an electron-injecting layer, and a hole-transporting layer. The EL layer 315 has an insertion layer, a charge generation layer, etc. It is preferable to have the organometallic complex shown in Embodiment 1.

[0216] The transistors and the organic EL devices 317 are disposed on a first substrate 301 and a second substrate 302. The first substrate 301 and the second substrate 302 are sealed by a plate 306 and a sealant 305. The space 318 surrounded by the plate 306 and the seal material 305 is filled with an inert gas (such as nitrogen or argon). ) or an organic material (including a sealant 305).

[0217] The sealing material 305 can be made of epoxy resin or glass frit. It is preferable to use a material that is as impermeable to moisture and oxygen as possible for the sealing material 305. When glass frit is used as the bonding material, the first substrate 301 and The second substrate 306 is preferably a glass substrate.

[0218] This embodiment mode can be combined with other embodiment modes as appropriate.

[0219] (Embodiment 3) In this embodiment, electronic devices in which the light-emitting device of one embodiment of the present invention can be used will be described. This will be explained with reference to FIG.

[0220] FIG. 4A shows a biometric authentication device for finger veins, which includes a housing 911, a light source 912, and a detection stage. The finger is placed on the detection stage 913 to capture an image of the shape of the veins. A light source 912 that emits near-infrared light is installed above the detection stage 913. The detection stage 913 is made of a material that transmits near-infrared light. The near-infrared light emitted from the light source 912 and transmitted through the finger is captured by the image capture device 914. An optical system is provided between the detection stage 913 and the imaging device 914. The above-mentioned device configuration may be used for a biometric authentication device targeting the veins of the palm. It is also possible.

[0221] The light-emitting device according to one embodiment of the present invention can be used as the light source 912. The light-emitting device can be installed in a curved shape and can illuminate the target object with uniform light. The strongest peak intensity is observed at wavelengths between 760 nm and 900 nm. It is preferable that the device is a light-emitting device that emits near-infrared light that transmits through fingers, palms, etc. By receiving light and imaging it, the position of the veins can be detected. This action is biometric authentication. In addition, by combining it with the global shutter method, High-precision sensing is possible even if the subject is moving.

[0222] In addition, the light source 912 may include a plurality of light emitting units, such as light emitting units 915, 916, and 917 shown in FIG. Each of the light emitting units 915, 916, and 917 can have an emission wavelength of They may be different, and each may be irradiated with light at a different time. Therefore, by changing the wavelength and angle of the irradiated light, different images can be captured continuously. This allows multiple images to be used for authentication, achieving high security. .

[0223] FIG. 4C shows a biometric authentication device for palm veins, which includes a housing 921, an operation button 92, 2, a detection unit 923, a light source 924 that emits near-infrared light, etc. By doing so, the shape of the veins in the palm of the hand can be recognized. A light source 924 is arranged around the detection unit 923. The object (hand) is illuminated. Then, the reflected light from the object is incident on the detection unit 923. The light-emitting device according to the embodiment can be used as the light source 924. The imaging device 925 is arranged to capture an image of the object (the whole image of the hand). An optical system may be provided between the sensor 923 and the image capture device 925. It can also be used in biometric authentication devices that target finger veins.

[0224] FIG. 4D shows a non-destructive testing device, which includes a housing 931, an operation panel 932, a transport mechanism 933, and a monitor. The sensor 934 includes a sensor unit 935, a light source 938 that emits near-infrared light, and the like. A light emitting device such as the above may be used as the light source 938. The member to be inspected 936 is conveyed by the conveying mechanism 9 The member to be inspected 936 is transported to a position directly below the detection unit 935 by a light source 938. Infrared light is irradiated, and the transmitted light is captured by an imaging device 937 provided in the detection unit 935. The captured image is displayed on a monitor 934. The products are transported by a meter, and defective products are separated and collected. It is possible to detect defective elements such as internal defects and foreign objects non-destructively and quickly.

[0225] FIG. 4E shows a mobile phone, which includes a housing 981, a display unit 982, an operation button 983, and an external connection port. 984, a speaker 985, a microphone 986, a first camera 987, and a second camera 988. The mobile phone includes a touch sensor in a display portion 982. The display unit 982 is flexible. It can be used for all operations such as making a call or entering text. The operation can be performed by touching the display unit 982 with a finger or a stylus. The first camera 987 can capture visible light images, and the second camera 988 can capture infrared light images (nearby). The mobile phone or display unit 982 shown in FIG. 4E can acquire a The light-emitting device according to one embodiment of the present invention may be included.

[0226] This embodiment mode can be combined with other embodiment modes as appropriate. EXAMPLES

[0227] (Synthesis Example 1) In this example, a synthesis method of an organometallic complex of one embodiment of the present invention will be described. is bis{4,6-dimethyl-2-[3-( 3,5-Dimethylphenyl)-2-benzo[g]quinoxalinyl-κN]phenyl-κC }(2,2,6,6-tetramethyl-3,5-heptanedionato-κ 2O,O') Iridescent This article describes the synthesis method of Ir(III) (abbreviation: [Ir(dmdpbq)2(dpm)]). Reveal.

[0228] [ka]

[0229] <Step 1: 2,3-bis-(3,5-dimethylphenyl)-2-benzo[g]quinoxadia Synthesis of Sarin (abbreviation: Hdmdpbq) First, in step 1, an organic compound according to one embodiment of the present invention, which is represented by structural formula (200), Hdmdpbq was synthesized. 3,3',5,5'-Tetramethylbenzyl 3.20g, 2 1.97 g of 3-diaminonaphthalene and 60 mL of ethanol were placed in a three-neck flask equipped with a reflux condenser. The inside of the flask was replaced with nitrogen and the flask was stirred at 90°C for 7.5 hours. After that, the product was purified by silica gel column chromatography using toluene as a developing solvent. The product was purified and the target product was obtained (yellow solid, yield 3.73 g, 79%). The scheme is shown in (a-1).

[0230] [ka]

[0231] Nuclear magnetic resonance spectroscopy of the yellow solid obtained in step 1 ( 1 The results of the analysis using H-NMR are shown below. As shown below. 1 The H-NMR chart is shown in FIG. It was found that Hdmdpbq, shown in structural formula (200), was obtained.

[0232] The obtained material 1 The 1 H NMR data is shown below. 1 H-NMR.δ(CD2Cl2):2.28(s,12H),7.01(s,2H) ,7.16(s,4H),7.56-7.58(m,2H),8.11-8.13(m, 2H),8.74(s,2H).

[0233] <Step 2: Di-μ-chloro-tetrakis{4,6-dimethyl-2-[3-(3,5- Dimethylphenyl)-2-benzo[g]quinoxalinyl-κN]phenyl-κC}diyl Synthesis of Ir(III) (abbreviation: [Ir(dmdpbq)2Cl]2) Next, in step 2, a dinuclear complex according to one embodiment of the present invention, represented by structural formula (210), Ir(dmdpbq)2Cl2 was synthesized using 15 mL of 2-ethoxyethanol and 5 mL of water. L, 1.81 g of Hdmdpbq obtained in step 1, and iridium chloride hydrate (IrC 0.66 g of 1.3·H2O (Furuya Metals) was placed in a recovery flask equipped with a reflux condenser. The atmosphere in the flask was replaced with argon. Then, microwaves (2.45 GHz, 100 W) were applied for 2 After the specified time had elapsed, the resulting residue was suction filtered and washed with methanol. The target product was obtained (black solid, yield 1.76 g, 81%). The model is shown in (a-2).

[0234] [ka]

[0235] <Step 3: Synthesis of [Ir(dmdpbq)2(dpm)]> In step 3, an organometallic complex according to one embodiment of the present invention, which is represented by structural formula (100), is We synthesized [Ir(dmdpbq)2(dpm)]. 2-Ethoxyethanol 20m L, 1.75 g of [Ir(dmdpbq)2Cl]2 obtained in step 2, 0.50 g of Hdpm and 0.95 g of sodium carbonate were added to a The mixture was placed in a recovery flask and the atmosphere in the flask was replaced with argon. Then, the mixture was heated in a microwave oven (2.45 G). The residue was suction filtered with methanol, then, The solid was washed with methanol. The resulting solid was mixed with silica gel using dichloromethane as a developing solvent. After purification by column chromatography, the product was dissolved in a mixture of dichloromethane and methanol. The target compound was obtained by recrystallization from the above-mentioned solution (dark green solid, yield 0.42 g, 21%). The dark green solid (0.41 g) obtained was purified by train sublimation. The purification conditions were a pressure of 2.7 Pa and argon gas at a flow rate of 10.5 mL / min. The dark green solid was heated at 300°C for 10 min. After purification by sublimation, a dark green solid was obtained in 78% yield. The synthetic scheme of trip 3 is shown in (a-3).

[0236] [ka]

[0237] Nuclear magnetic resonance spectroscopy of the dark green solid obtained in step 3 ( 1 H-NMR) analysis results As shown below. Also, 1 The H-NMR chart is shown in FIG. As a result, it was found that [Ir(dmdpbq)2(dpm)] shown in structural formula (100) was obtained. It was.

[0238] The obtained material 1 The 1 H NMR data is shown below. 1H-NMR.δ(CD2Cl2):0.75(s,18H),0.97(s,6H) ,2.01(s,6H),2.52(s,12H),4.86(s,1H),6.39( s,2H),7.15(s,2H),7.31(s,2H),7.44-7.51(m, 4H),7.80(d,2H),7.86(s,4H),8.04(d,2H),8.4 2(s,2H),8.58(s,2H).

[0239] Next, the UV-visible absorption spectrum of the dichloromethane solution of [Ir(dmdpbq)2(dpm)] The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured.

[0240] The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V550, manufactured by JASCO Corporation). Then, put the dichloromethane solution (0.010mmol / L) into a quartz cell and perform the measurement at room temperature. The emission spectrum was measured using a fluorometer (FS9 manufactured by Hamamatsu Photonics Co., Ltd.). 20) was used to prepare a deoxygenated dichloromethane solution (0.010 mmol / L) under a nitrogen atmosphere. The solution was placed in a quartz cell, which was then sealed, and the measurement was carried out at room temperature.

[0241] The measurement results of the absorption spectrum and emission spectrum are shown in Figure 7. The horizontal axis is the wavelength, and the vertical axis is The thin solid lines in Fig. 7 show the absorption spectrum, and the thick solid lines show the emission intensity. The lines indicate the emission spectrum. The absorption spectrum shown in FIG. 7 was obtained by 10mmol / 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.

[0242] As shown in FIG. 7, an organometallic complex according to one embodiment of the present invention, [Ir(dmdpbq)2( dpm)] has an emission peak at 807 nm, and from a dichloromethane solution, it emits near-infrared light. was observed.

[0243] The weight loss rate of the obtained [Ir(dmdpbq)2(dpm)] was measured using a high vacuum differential spectrometer. Measured using a thermobalance (Bruker AXS, TG-DTA2410SA). The vacuum level was set at 10 Pa, and the heating rate was set at 10°C / min. As shown in FIG. 8, the organometallic complex of one embodiment of the present invention, [Ir(dmdpbq)2(d pm)] is a weight loss rate of 100% (corresponding to the weight loss rate of -100% in Figure 8). It was found that the polymer exhibited good sublimation properties.

[0244] For the above reasons, in this example, the organometallic complex [Ir(dmd pbq)2(dpm)] was successfully synthesized. [Ir(dmdpbq)2(dpm) It was confirmed that the compound can emit near-infrared light and has good sublimation properties.

[0245] [Ir(dmdpbq)2(dpm)] is a compound represented by the general formula (G1) in which X is an unsubstituted benzene This is an example of a case where X is a benzene ring. The π-conjugated system is extended, and LU The MO level can be deepened and made energetically stable, resulting in near-infrared emission. It is considered that [Ir(dmdpbq)2(dpm)] is the compound represented by the general formula (G1). R 1 , R 3 , R 6 , and R 8 This is an example where R is a methyl group. 1 , R 3 , R 6 , and R 8are both methyl groups, so that X is a condensed ring (benzene ring) Since the decrease in sublimability can be suppressed, the organic metal complex has good sublimability and emits near infrared light. It is believed that the above results were obtained. EXAMPLES

[0246] In this example, the results of manufacturing a light-emitting device according to one embodiment of the present invention will be described. The bis{4,6-dimethyl-2-[3-(3,5-dimethylphenyl)phenyl]phenylene sulfonate described in Example 1 was used. {2,2,6,6-nyl)-2-benzo[g]quinoxalinyl-κN]phenyl-κC}(2,2,6,6- Tetramethyl-3,5-heptanedionato-κ 2 O,O') Iridium(III) (abbreviation :[Ir(dmdpbq)2(dpm)]) (structural formula (100)) was used as the light-emitting layer. The structure, fabrication method, and characteristics of device 1 will be described.

[0247] The light-emitting device 1 produced in this example has a light-emitting organic compound in the light-emitting layer. The maximum peak wavelength of the light emitted by the organic compound is 760 nm or more and 900 nm or less. The light-emitting device 1 is an example of an optical device. The light-emitting device 1 is a light-emitting organic compound having a metal-carbon bond. This is an example of a light-emitting device using an organometallic complex having a bond.

[0248] The structure of the light-emitting device 1 used in this embodiment is shown in FIG. 9A, and the specific configuration is shown in Table 1. The chemical formulas of the materials used in this example are shown below.

[0249] [Table 1]

[0250] [ka]

[0251] <<Creating light-emitting device 1>> The light emitting device 1 shown in this embodiment has a first electrode 801 on a substrate 800 as shown in FIG. A hole injection layer 811, a hole transport layer 812, and a light emitting layer 813 are formed on the first electrode 801. , an electron transport layer 814, and an electron injection layer 815 are laminated in this order, and a second The electrode 803 has a laminated structure.

[0252] First, a first electrode 801 was formed on a substrate 800. The electrode area was 4 mm 2 (2mm x 2 The substrate 800 was a glass substrate. The first electrode 801 was made of silicon oxide. The indium tin oxide (ITSO) containing the fluorine atom was deposited by sputtering to a thickness of 110 nm. In this embodiment, the first electrode 801 functions as an anode.

[0253] As a pretreatment, the surface of the substrate is washed with water, baked at 200°C for 1 hour, and then UV-treated. The treatment was carried out for 370 seconds. -4 Vacuum deposition equipment with the inside pressure reduced to about Pa The substrate was placed in the vacuum deposition apparatus and vacuum baked at 170°C for 30 minutes in the heating chamber of the vacuum deposition apparatus. After that, the substrate was allowed to cool for about 30 minutes.

[0254] Next, a hole injection layer 811 was formed on the first electrode 801. The hole injection layer 811 was formed by vacuum evaporation. 10 -4 After reducing the pressure to 100 Pa, 1,3,5-tri(dibenzothiophene-4-isotope DBT3P-II: benzene (abbreviation: DBT3P-II) and molybdenum oxide The molybdenum oxide was mixed with molybdenum chloride at a weight ratio of 2:1, and the film was co-deposited to a thickness of 60 nm. .

[0255] Next, a hole transport layer 812 was formed on the hole injection layer 811. The hole transport layer 812 was made of 4-fluorophenyl ether. 4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BP The film was formed by deposition using AFLP to a thickness of 20 nm.

[0256] Next, a light-emitting layer 813 was formed on the hole-transporting layer 812. (Dibenzothiophene-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxa Phosphorus (abbreviation: 2mDBTBPDBq-II) was used as the assist material, and N-(1,1 '-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl] PCBBi F) is used as a guest material (phosphorescent material), and the organometallic complex of one embodiment of the present invention, Ir(dmdpbq)2(dpm)] was used with a weight ratio of 2mDBTBPDBq-II:P CBBiF:[Ir(dmdpbq)2(dpm)]=0.7:0.3:0.1 The film thickness was 40 nm.

[0257] Next, an electron transport layer 814 was formed on the light emitting layer 813. The electron transport layer 814 was made of 2mDBT The thickness of BPDBq-II is 20 nm, and 2,9-bis(naphthalene-2-yl)-4,7- The thickness of the diphenyl-1,10-phenanthroline (NBphen) film is 70 nm. The layers were deposited in sequence as shown in FIG.

[0258] Next, the electron injection layer 815 was formed on the electron transport layer 814. The electron injection layer 815 was made of fluoride. Lithium (LiF) was used and the film was formed by vapor deposition to a thickness of 1 nm.

[0259] Next, a second electrode 803 was formed on the electron injection layer 815. The second electrode 803 was made of aluminum. The aluminum was deposited by vapor deposition to a thickness of 200 nm. Thus, the second electrode 803 functions as a cathode.

[0260] Through the above steps, a light-emitting device is formed on the substrate 800, which has an EL layer 802 sandwiched between a pair of electrodes. The hole injection layer 811, the hole transport layer 812, and the light emitting layer 813 were formed. The organic electroluminescent layer 813, the electron transport layer 814, and the electron injection layer 815 constitute an EL layer in one embodiment of the present invention. In addition, the deposition process in the above-mentioned manufacturing method is all performed by resistance heating. The deposition method was used.

[0261] The light-emitting device fabricated as described above is sealed with another substrate (not shown). When sealing using another substrate (not shown), the device is sealed in a glove box with a nitrogen atmosphere. In the above, another substrate (not shown) coated with an adhesive that is hardened by ultraviolet light is placed on the substrate 800. The substrate 800 is fixed to the substrate 800 so that the adhesive adheres to the periphery of the light emitting device formed on the substrate 800. The sealing was performed by applying 365 nm ultraviolet light at 6 J / cm. 2 Irradiate the adhesive to harden it, The adhesive was stabilized by heat treatment at 80° C. for 1 hour.

[0262] <Operation characteristics of light-emitting device 1> The operating characteristics of the light-emitting device 1 were measured. The measurements were performed in an atmosphere maintained at room temperature (25°C). I went there with a feeling of excitement.

[0263] FIG. 10 shows the current density-radiant emittance characteristics of the light-emitting device 1. FIG. FIG. 12 shows the current density-radiant flux characteristic of the light-emitting device 1. Figure 13 shows the voltage-radiant emittance characteristics of the light-emitting device 1. Figure 14 shows the voltage-radiant emittance characteristics of the light-emitting device 1. The current density-external quantum efficiency characteristics of 1 are shown in Fig. 1. The radiant emittance, radiant flux, and external quantum efficiency are shown in Fig. was calculated using radiance, assuming that the light distribution characteristic of the light-emitting device is a Lambertian type. .

[0264] Table 2 shows 7.4 W / sr / m 2 4 shows main initial characteristic values ​​of the light emitting device 1 in the vicinity.

[0265] [Table 2]

[0266] As shown in FIGS. 10 to 14 and Table 2, it is clear that the light emitting device 1 exhibits excellent characteristics. I did.

[0267] In addition, 51 mA / cm2 was applied to the light-emitting device 1. 2 Emission spectrum when a current is applied at a current density of The emission spectrum was measured using a near-infrared spectroradiometer (SR-NIR, As shown in FIG. 15, the light-emitting device 1 includes a light-emitting layer 813. The maximum peak at around 796 nm is due to the emission of [Ir(dmdpbq)2(dpm)]. The emission spectrum showed

[0268] The half-width of the emission spectrum was 67 nm. This is approximately 0.13 eV, which is quite narrow for emission from an organometallic complex. Device 1 is light between 760nm and 900nm (or between 780nm and 880nm) It efficiently emits light of 1000 nm, making it highly effective as a light source for sensors and other applications.

[0269] <Reliability test of light-emitting device 1> Next, a reliability test was performed on the light emitting device 1. The results of the reliability test are shown in FIG. In FIG. 16, the vertical axis indicates normalized luminescence intensity (%) when the initial luminescence intensity is set to 100%. The horizontal axis indicates the driving time (h). The reliability test was performed at a current density of 75 mA / cm 2 Set up The light emitting device 1 was then driven.

[0270] The results of the reliability test showed that the light-emitting device 1 exhibited high reliability. This is because: The organometallic complex according to one embodiment of the present invention, [Ir(dmdpbq)2(dpm)] (structural formula This is believed to be an effect of using a ZnO(100)) for the light-emitting layer of the light-emitting device 1. EXAMPLES

[0271] In this example, the results of manufacturing a light-emitting device according to one embodiment of the present invention will be described. The light-emitting device 2 produced in this example has a light-emitting organic compound in the light-emitting layer. The maximum peak wavelength of the light emitted by the organic compound is 760 nm or more and 900 nm or less. The following describes the results of fabricating a light-emitting device 2 and measuring its characteristics. Reveal.

[0272] In the light-emitting device 2, the light-emitting organic compound is bis(dibenzo[a,i]naphtho[2 ,1-c]phenazin-10-yl-κC 10 ,κN 11 )(2,2,6,6-tetramethyl Tyl-3,5-heptanedionate-κ2 O,O') Iridium(III) (abbreviation: [Ir In other words, the light-emitting device 2 was This is an example of a light-emitting device that uses an organometallic complex with a metal-carbon bond in a non-polar organic compound. A synthesis example of [Ir(dbnphz)2(dpm)] will be described later in the Reference Examples.

[0273] The specific configuration of the light-emitting device 2 used in this example is shown in Table 3. The structure of the light-emitting device 2 is the same as that of the light-emitting device 1 (FIG. 9A), and the fabrication method thereof is as described in Example 2. The chemical formulas of the materials used in this example are shown below.

[0274] [Table 3]

[0275] [ka]

[0276] <Operation characteristics of light-emitting device 2> The operating characteristics of the light-emitting device 2 were measured. The measurements were performed in an atmosphere maintained at room temperature (25°C). I went there with a feeling of excitement.

[0277] FIG. 17 shows the current density-radiant emittance characteristics of the light-emitting device 2. FIG. FIG. 19 shows the voltage-current density characteristics of the light-emitting device 2. Figure 20 shows the voltage-radiant emittance characteristics of the light-emitting device 2. Figure 21 shows the voltage-radiant emittance characteristics of the light-emitting device 3. The current density-external quantum efficiency characteristics of 2 are shown in Fig. 1. The radiant emittance, radiant flux, and external quantum efficiency are shown in Fig. 1. was calculated using radiance, assuming that the light distribution characteristic of the light-emitting device is a Lambertian type. .

[0278] Table 4 shows 0.11 W / sr / m 2 4 shows main initial characteristic values ​​of the light emitting device 2 in the vicinity.

[0279] [Table 4]

[0280] As shown in FIGS. 17 to 21 and Table 4, the light-emitting device 2 exhibits excellent element characteristics. Understood.

[0281] In addition, 15 mA / cm2 is applied to the light-emitting device 2. 2 Emission spectrum when a current is applied at a current density of is shown in FIG. 22. In FIG. 22, the emission spectrum was measured using a near-infrared spectroradiometer (S The light-emitting device 2 was made of [I r(dbnphz)2(dpm)] has a maximum peak at around 870 nm. The emission spectrum is shown.

[0282] The half-width of the emission spectrum was 63 nm. This is approximately 0.10 eV, which is quite narrow for emission from an organometallic complex. Vise 2 is for light between 760nm and 900nm (or between 780nm and 880nm) It efficiently emits light of 1000 nm, making it highly effective as a light source for sensors and other applications.

[0283] <Reliability test of light-emitting device 2> Next, a reliability test was performed on the light emitting device 2. The results of the reliability test are shown in FIG. In FIG. 23, the vertical axis indicates normalized luminescence intensity (%) when the initial luminescence intensity is set to 100%. The horizontal axis indicates the operation time (h) of the element. The reliability test was performed at a current density of 75 mA / cm 2 and the light-emitting device 2 was driven.

[0284] The results of the reliability test showed that the light emitting device 2 exhibited high reliability. EXAMPLES

[0285] In this example, the results of manufacturing a light-emitting device according to one embodiment of the present invention will be described. In the example, [Ir(dmdpbq)2(dpm)] was used as the light-emitting layer. The structure, fabrication method, and characteristics of Device 3 will be described.

[0286] The light-emitting device 3 produced in this example has a light-emitting organic compound in the light-emitting layer. The maximum peak wavelength of the light emitted by the organic compound is 760 nm or more and 900 nm or less. The light-emitting device 3 is an example of an optical device. The light-emitting device 3 is a light-emitting organic compound having a metal-carbon bond. This is an example of a light-emitting device using an organometallic complex having a bond.

[0287] The structure of the light-emitting device 3 used in this embodiment is shown in FIG. 3 is a two-layer EL layer (EL layer 803) between a pair of electrodes (a first electrode 801 and a second electrode 803). 802a and 802b), and a charge generating layer 816 is provided between the two EL layers. This is a light-emitting device with a tandem structure.

[0288] The specific configuration of the light-emitting device 3 used in this example is shown in Table 5. The chemical formula of the material used is shown below.

[0289] [Table 5]

[0290] [ka]

[0291] <<Creating light-emitting device 3>> The light-emitting device 3 shown in this embodiment has a first electrode 801 on a substrate 800 as shown in FIG. On the first electrode 801, an EL layer 802a (hole injection layer 811a, hole transport layer 8 12a, a light-emitting layer 813a, an electron transport layer 814a, and an electron injection layer 815a), a charge generating layer 816, and the EL layer 802b (hole injection layer 811b, hole transport layer 812b, light emitting layer 813 b, an electron transport layer 814b, and an electron injection layer 815b) are laminated in this order on the EL layer 802b. The second electrode 803 is laminated on the first electrode 802 .

[0292] First, a first electrode 801 was formed on a substrate 800. The electrode area was 4 mm 2 (2mm x 2 The thickness of the substrate 800 was 1 mm. The substrate 800 was a glass substrate. The first electrode 801 was a silver (Ag) and an alloy of palladium (Pd) and copper (Cu) (Ag-Pd-Cu (APC)) was sputtered. The film was formed to a thickness of 100 nm by the sputtering method, and ITSO was deposited by the sputtering method. In this embodiment, the first electrode 801 is formed to a thickness of 10 nm. It functions as an anode.

[0293] As a pretreatment, the surface of the substrate is washed with water, baked at 200°C for 1 hour, and then UV-treated. The treatment was carried out for 370 seconds. -4 Vacuum deposition equipment with the inside pressure reduced to about Pa The substrate was placed in the vacuum deposition apparatus and vacuum baked at 170°C for 30 minutes in the heating chamber of the vacuum deposition apparatus. After that, the substrate was allowed to cool for about 30 minutes.

[0294] Next, a hole injection layer 811a was formed on the first electrode 801. The hole injection layer 811a was formed of a crystalline silicon. 10 minutes inside the empty deposition chamber -4 After depressurizing to 100 Pa, DBT3P-II and molybdenum oxide were The ratio of BT3P-II to molybdenum oxide was 2:1 (by weight), and the film thickness was set to 10 nm. It was formed by co-evaporation.

[0295] Next, a hole transport layer 812a was formed on the hole injection layer 811a. The hole transport layer 812a was The film was formed by vapor deposition using PCBBiF to a thickness of 30 nm.

[0296] Next, the light-emitting layer 813a was formed on the hole-transporting layer 812a. TBPDBq-II was used as the assist material, PCBBiF was used as the guest material (phosphorus As an example of an optical material, an organometallic complex according to one embodiment of the present invention, [Ir(dmdpbq)2(d pm)] was used, and the weight ratio was 2mDBTBPDBq-II:PCBBiF:[Ir(dmd pbq)2(dpm)] = 0.7:0.3:0.1. was set to 40 nm.

[0297] Next, the electron transport layer 814a was formed on the light emitting layer 813a. The thickness of DBTBPDBq-II was 20 nm, and the thickness of NBphen was 90 nm. The layers were formed by sequential deposition.

[0298] Next, the electron injection layer 815a was formed on the electron transport layer 814a. Lithium oxide (Li2O) was used and formed by vapor deposition to a film thickness of 0.1 nm.

[0299] Next, a charge generation layer 816 was formed on the electron injection layer 815a. The charge generation layer 816 was made of copper ( II) Phthalocyanine (CuPc) was used and evaporated to a thickness of 2 nm. .

[0300] Next, a hole injection layer 811b was formed on the charge generation layer 816. The hole injection layer 811b was formed of D BT3P-II and molybdenum oxide were mixed at a ratio of DBT3P-II:molybdenum oxide=2:1 (heavy) The film was formed by co-evaporation at a ratio of 1:1 to 1:10.

[0301] Next, a hole transport layer 812b was formed on the hole injection layer 811b. The hole transport layer 812b was The film was formed by vapor deposition using PCBBiF to a thickness of 60 nm.

[0302] Next, the light-emitting layer 813b was formed on the hole-transporting layer 812b. TBPDBq-II was used as the assist material, PCBBiF was used as the guest material (phosphorus As an example of an optical material, an organometallic complex according to one embodiment of the present invention, [Ir(dmdpbq)2(d pm)] was used, and the weight ratio was 2mDBTBPDBq-II:PCBBiF:[Ir(dmd pbq)2(dpm)] = 0.7:0.3:0.1. was set to 40 nm.

[0303] Next, the electron transport layer 814b was formed on the light emitting layer 813b. The thickness of DBTBPDBq-II was 20 nm, and the thickness of NBphen was 65 nm. The layers were formed by sequential deposition.

[0304] Next, the electron injection layer 815b was formed on the electron transport layer 814b. The electron injection layer 815b was Lithium fluoride (LiF) was used and was deposited to a thickness of 1 nm.

[0305] Next, a second electrode 803 was formed on the electron injection layer 815b. The second electrode 803 was made of silver ( The volume ratio of Ag to magnesium (Mg) was 10:1, and the film thickness was 20 In this embodiment, the second electrode 803 was formed by co-evaporation so as to have a thickness of about 1 nm. It functions as a cathode.

[0306] Next, a buffer layer 804 was formed on the second electrode 803. The buffer layer 804 was made of DBT. The film was formed by deposition using 3P-II so as to have a thickness of 110 nm.

[0307] Through the above steps, the light-emitting device 3 was formed on the substrate 800. In the deposition process, deposition by resistance heating was used for all the layers.

[0308] The light emitting device 3 is sealed by another substrate (not shown). Similar to Device 1, see Example 2.

[0309] The light emitting device 3 has a microcavity structure. The optical distance between a pair of reflective electrodes (APC film and Ag:Mg film) is the maximum distance for the emission of the guest material. It was made to be approximately one wavelength with respect to the large peak wavelength.

[0310] <Operation characteristics of light-emitting device 3> The operating characteristics of the light-emitting device 3 were measured. The measurements were performed in an atmosphere maintained at room temperature (25° C.). I went there with a feeling of excitement.

[0311] FIG. 24 shows the current density-radiant emittance characteristics of the light-emitting device 3. FIG. FIG. 26 shows the current density-radiant flux characteristics of the light-emitting device 3. Figure 27 shows the voltage-radiant emittance characteristics of the light-emitting device 3. Figure 28 shows the voltage-radiant emittance characteristics of the light-emitting device 3. The current density-external quantum efficiency characteristics of 3 are shown in Fig. 3. The radiant emittance, radiant flux, and external quantum efficiency are shown in Fig. 3. was calculated using radiance, assuming that the light distribution characteristic of the light-emitting device is a Lambertian type. .

[0312] 6.8W / sr / m in Table 6 2 4 shows main initial characteristic values ​​of the light emitting device 3 in the vicinity.

[0313] [Table 6]

[0314] As shown in FIGS. 24 to 28 and Table 6, it is clear that the light emitting device 3 exhibits excellent characteristics. The light-emitting device 3 has a tandem structure, and therefore has a high peak EL intensity. We were able to obtain highly efficient results.

[0315] In addition, 10 mA / cm2 was applied to the light-emitting device 3. 2 Emission spectrum when a current is applied at a current density of The emission spectrum was measured using a near-infrared spectroradiometer (SR-NIR, As shown in FIG. 29, the light-emitting device 3 includes a light-emitting layer 813a and a light-emitting The emission of [Ir(dmdpbq)2(dpm)] contained in layer 813b is The emission spectrum showed a maximum peak at around 1 nm.

[0316] In addition, the use of a microcavity structure narrows the emission spectrum, The half-width was 32 nm. (or light between 780nm and 880nm) efficiently, and is suitable for sensor applications, etc. It can be said to be highly effective as a light source.

[0317] <Reliability test of light-emitting device 3> Next, a reliability test was carried out on the light emitting device 3. The results of the reliability test are shown in FIG. In FIG. 30, the vertical axis indicates the normalized luminescence intensity (%) when the initial luminescence intensity is set to 100%. The horizontal axis indicates the driving time (h). The reliability test was performed at a current density of 75 mA / cm 2 Set up The light emitting device 3 was then driven.

[0318] The results of the reliability test showed that the light-emitting device 3 exhibited high reliability. This is because: The organometallic complex according to one embodiment of the present invention, [Ir(dmdpbq)2(dpm)] (structural formula This is believed to be an effect of using the (100)) for the light-emitting layer of the light-emitting device 3.

[0319] <Viewing angle characteristics of light-emitting device 3> Next, the viewing angle characteristics of the EL spectrum of the light-emitting device 3 were examined.

[0320] First, the EL spectrum of the light-emitting element in the front direction and the EL spectrum in the oblique direction were measured. Specifically, the direction perpendicular to the light-emitting surface of the light-emitting device 3 is set to 0°, and the angle is set to a range from −80° to 80°. The emission spectrum was measured at 17 points every 10°. A photometer (Hamamatsu Photonics, PMA-12) was used. From the measurement results, The EL spectrum and photon intensity ratio of the light-emitting device were obtained.

[0321] FIG. 31 shows the EL spectrum of light-emitting device 3 from 0° to 60°.

[0322] FIG. 32 shows the photon intensity at each angle ( Normalized photon intensity at Angle sity) is shown. Figure 32 further illustrates the Lambertian characteristics.

[0323] As shown in FIGS. 31 and 32, the light emitting device 3 has a large viewing angle dependency. It was found that strong light was emitted. This was because the device used a microcavity structure. This is because the light emitted in the front direction was strengthened while the light emitted in the oblique direction was weakened. In this way, the viewing angle characteristic with strong emission in the front direction is suitable for use as a light source for sensors such as vein sensors. It is suitable as a source.

[0324] (Reference example) The bis(dibenzo[a,i]naphtho[2,1-c]phenazine-10 used in Example 3 above -Ile-κC 10 ,κN 11 )(2,2,6,6-tetramethyl-3,5-heptanedioate Nat-κ 2 O,O') Iridium(III) (abbreviation: [Ir(dbnphz)2(dpm The synthesis method of [Ir(dbnphz)2(dpm)] will be specifically explained. The structure is shown below.

[0325] [ka]

[0326] <Step 1: Dibenzo[a,i]naphtho[2,1-c]phenazine (abbreviation: Hdbnp hz) synthesis> First, 1.0 g (4.0 mmol) of chrysene-5,6-dione and 2,3-diaminonaphthalene were Put 0.67 g (4.3 mmol) of toluene and 20 mL of ethanol into a reaction vessel and heat for 5 hours. After a predetermined time had passed, the resulting mixture was filtered by suction, and the solid was washed with ethanol. This solid was dissolved in heated toluene and filtered through a layer of Celite, alumina, and Celite. The filtrate was concentrated and then diluted with a mixture of toluene and ethanol. The target product was obtained by recrystallization (1.1 g, 74% yield). The synthesis scheme for step 1 is shown below (b- 1).

[0327] [ka]

[0328] <Step 2: Synthesis of [Ir(dbnphz)2(dpm)]> Next, 1.1 g (2.9 mmol) of Hdbnphz obtained in step 1 and iridium chloride aqueous solution The reaction volume was 0.39 g (1.3 mmol) of the solvate and 30 mL of dimethylformamide (DMF). The inside of the vessel was replaced with nitrogen, and the mixture was heated and stirred at 160°C for 7.5 hours. 0.55 g (5.2 mmol) of sodium carbonate and 0.72 g (3.9 mmol) of dipivaloylmethane The mixture was then heated and stirred at 140° C. for 14 hours. The obtained solid was washed with water and ethanol.

[0329] Next, this was purified by silica gel column chromatography using dichloromethane as a developing solvent. The solid was purified and the obtained fraction was concentrated to obtain a solid. After washing, 133 mg of the desired product was obtained.

[0330] The filtrate was then concentrated and purified by silica gel column chromatography using toluene as a developing solvent. The fraction was then concentrated, and the solid was purified by toluene and ethanol. The product was recrystallized using a mixed solvent of ethanol and methanol to obtain the target product (80 mg) (total yield 213 mg, The synthetic scheme of step 2 is shown in formula (b-2).

[0331] [ka]

[0332] The protons ( 1 H) measured by nuclear magnetic resonance (NMR) The values ​​obtained are shown below. From the measurement results, [Ir(dbnphz)2(dpm)] ) was found to be obtained.

[0333] 1 H-NMR δ(CDCl3):0.52(s,18H),5.04(s,1H), 6.80(d,2H),6.97(t,2H),7.48(d,2H),7.59(t, 2H),7.74(t,2H),7.88(d,2H),7.98(t,2H),8.0 6(d,2H),8.10(d,2H),8.26(d,4H),8.64(d,2H) ,9.13(s,2H),9.19(s,2H),11.21(d,2H). [Explanation of symbols]

[0334] 101: first electrode, 102: second electrode, 103: EL layer, 103a: EL layer, 103 b: EL layer, 104: charge generation layer, 111: hole injection layer, 112: hole transport layer, 113: Light-emitting layer, 114: electron transport layer, 115: electron injection layer, 301: first substrate, 302: pixel part, 303: circuit part, 304a: circuit part, 304b: circuit part, 305: sealing material, 306 : second substrate, 307: wiring, 308: FPC, 309: transistor, 310: transistor 311: transistor; 312: transistor; 313: first electrode; 314: Insulating layer, 315: EL layer, 316: second electrode, 317: organic EL device, 318: space Between the electrodes, 401: first electrode, 402: EL layer, 403: second electrode, 405: insulating layer, 40 6: Conductive layer, 407: Adhesive layer, 416: Conductive layer, 420: Substrate, 422: Adhesive layer, 423 : Barrier layer, 424: Insulating layer, 450: Organic EL device, 490a: Substrate, 490b: Substrate, 490c: Barrier layer, 800: Substrate, 801: First electrode, 802: EL layer, 80 2a: EL layer, 802b: EL layer, 803: second electrode, 804: buffer layer, 811: Hole injection layer, 811a: hole injection layer, 811b: hole injection layer, 812: hole transport layer, 81 2a: hole transport layer, 812b: hole transport layer, 813: light emitting layer, 813a: light emitting layer, 813 b: light-emitting layer, 814: electron transport layer, 814a: electron transport layer, 814b: electron transport layer, 81 5: electron injection layer, 815a: electron injection layer, 815b: electron injection layer, 816: charge generation layer, 911: housing, 912: light source, 913: detection stage, 914: imaging device, 915: light emission part, 916: light-emitting part, 917: light-emitting part, 921: housing, 922: operation button, 923: detection sensor, 924: light source, 925: imaging device, 931: housing, 932: operation panel, 933: Conveyor mechanism, 934: monitor, 935: detection unit, 936: inspected member, 937: imaging Device, 938: light source, 981: housing, 982: display unit, 983: operation button, 984: exterior External connection port, 985: Speaker, 986: Microphone, 987: Camera, 988: Camera

Claims

1. A first electrode, a second electrode, a first light-emitting layer, a second light-emitting layer, and a charge generating layer, the first light-emitting layer is located between the first electrode and the charge generating layer; the charge generating layer is located between the first light emitting layer and the second light emitting layer; the second light-emitting layer is located between the charge generating layer and the second electrode; At least one of the first light-emitting layer and the second light-emitting layer includes a light-emitting organic compound, a first organic compound, and a second organic compound; the first organic compound and the second organic compound are a combination that forms an exciplex, the luminescent organic compound is an organometallic complex having a metal-carbon bond; The organometallic complex has two to five fused heteroaromatic rings and a first benzene ring, the fused heteroaromatic ring and the first benzene ring are each coordinated to the metal; the first benzene ring is bonded to the fused heteroaromatic ring; A light-emitting device, wherein the maximum peak wavelength of light emitted by the light-emitting organic compound is 760 nm or more and 900 nm or less.

2. A first electrode, a second electrode, a first light-emitting layer, a second light-emitting layer, and a charge generating layer, the first light-emitting layer is located between the first electrode and the charge generating layer; the charge generating layer is located between the first light emitting layer and the second light emitting layer; the second light-emitting layer is located between the charge generating layer and the second electrode; At least one of the first light-emitting layer and the second light-emitting layer includes a light-emitting organic compound, a first organic compound, and a second organic compound; the first organic compound and the second organic compound are a combination that forms an exciplex, the luminescent organic compound is an organometallic complex having a metal-carbon bond; The organometallic complex has two or more and five or less fused heteroaromatic rings, a first benzene ring, and a second benzene ring, the fused heteroaromatic ring and the first benzene ring are each coordinated to the metal; the first benzene ring and the second benzene ring are bonded to the fused heteroaromatic ring; A light-emitting device, wherein the maximum peak wavelength of light emitted by the light-emitting organic compound is 760 nm or more and 900 nm or less.

3. In claim 1 or 2, A light-emitting device, wherein the light-emitting organic compound is a cyclometal complex.

4. In any one of claims 1 to 3, A light-emitting device, wherein the luminescent organic compound is an ortho-metal complex.

5. In any one of claims 1 to 4, A light-emitting device, wherein the luminescent organic compound is an iridium complex.

6. In any one of claims 1 to 5, A light-emitting device, wherein the maximum peak wavelength of light emitted by the light-emitting organic compound is 780 nm or more and 880 nm or less.

7. In any one of claims 1 to 6, A light-emitting device, wherein the charge generating layer has a near-infrared light transmittance of 40% or more.

8. In any one of claims 1 to 7, A light emitting device, wherein the electrical conductivity of the charge generating layer is lower than the electrical conductivity of the first electrode and the electrical conductivity of the second electrode.

9. A light emitting device according to any one of claims 1 to 8; A light emitting device comprising: a transistor and / or a substrate.

10. A light emitting device according to claim 9 ; A light emitting module having a connector and / or an integrated circuit.

11. A light emitting module according to claim 10; An electronic device having at least one of an antenna, a battery, a housing, a camera, a speaker, a microphone, and an operation button.

12. A light emitting device according to claim 9 ; A lighting device having at least one of a housing, a cover, and a support base.

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