JP7275042B2 - Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device - Google Patents

Description

One embodiment of the present invention relates to organic compounds, light-emitting elements, light-emitting devices, electronic devices, and lighting devices. However, one embodiment of the present invention is not limited thereto. That is, one aspect of the present invention relates to an article, method, manufacturing method, or driving method. Alternatively, one aspect of the invention relates to a process, machine, manufacture, or composition of matter. Further, specifically, a semiconductor device, a display device, a liquid crystal display device, and the like can be given as examples.

A light-emitting element (also called an organic EL element), which has an EL layer sandwiched between a pair of electrodes, has characteristics such as thinness and lightness, high-speed response to input signals, and low power consumption. , is attracting attention as a next-generation flat panel display.

In a light-emitting element, when a voltage is applied between a pair of electrodes, electrons and holes injected from each electrode are recombined in the EL layer, and the light-emitting substance (organic compound) contained in the EL layer is excited. Light is emitted when the excited state returns to the ground state. As types of excited states, there are a singlet excited state (S ^* ) and a triplet excited state (T ^* ). Light emission from the singlet excited state is fluorescence, and light emission from the triplet excited state is phosphorescence. being called. Also, their statistical generation ratio in the light-emitting device is considered to be S ^* :T ^* =1:3.

Among the above-mentioned luminescent substances, compounds that can convert energy in a singlet excited state into luminescence are called fluorescent compounds (fluorescent materials), and can convert energy in a triplet excited state into luminescence. Such compounds are called phosphorescent compounds (phosphorescent materials).

Therefore, based on the above generation ratio, the theoretical limit of the internal quantum efficiency (ratio of photons generated to injected carriers) in a light emitting device using each of the above light emitting materials is is 25%, and when a phosphorescent material is used, it is 75%.

That is, a light-emitting element using a phosphorescent material can achieve higher efficiency than a light-emitting element using a fluorescent material. Therefore, in recent years, various types of phosphorescent materials have been actively developed. In particular, due to its high phosphorescence quantum yield, organometallic complexes having iridium or the like as a central metal are attracting attention (for example, Patent Document 1).

JP 2009-023938 A

As reported in the above-mentioned Patent Document 1, the development of phosphorescent materials exhibiting excellent properties is progressing, but the development of new materials exhibiting even better properties is desired.

Accordingly, one embodiment of the present invention provides a novel organometallic complex. Further, one embodiment of the present invention provides a novel organometallic complex with excellent heat resistance. Further, one embodiment of the present invention provides a novel organometallic complex that is less likely to decompose during sublimation. Further, one embodiment of the present invention provides a novel organometallic complex with high color purity. Another embodiment of the present invention provides a novel organometallic complex with high molecular orientation. Another embodiment of the present invention provides a novel organometallic complex that can be used for a light-emitting element. Further, one embodiment of the present invention provides a novel organometallic complex that can be used for an EL layer of a light-emitting element. Further, a highly efficient and highly reliable novel light-emitting element using the novel organometallic complex which is one embodiment of the present invention is provided. Further, a novel light-emitting device, a novel electronic device, or a novel lighting device is provided. The description of these problems does not preclude the existence of other problems. Moreover, one aspect of the present invention does not necessarily have to solve all of these problems. In addition, problems other than these are self-evident from the descriptions of the specification, drawings, claims, etc., and it is possible to extract problems other than these from the descriptions of the specification, drawings, claims, etc. is.

One aspect of the present invention is that the pyrimidine ring coordinated to Ir has at least one phenyl group having a cyano group as a substituent, and the phenyl group having a cyano group is attached to the 6-position of the pyrimidine ring. It is an organometallic complex represented by the following general formula (G1).

However, in general formula (G1), each of R ¹ to R ⁴ is independently hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring. , represents either a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms forming a ring. R ⁵ to R ⁹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or represents any one of 3 to 12 substituted or unsubstituted heteroaryl groups or cyano groups, at least one of which represents a cyano group; Moreover, L represents a monoanionic ligand. Moreover, n represents an integer of 1 to 3.

Another embodiment of the present invention is an organometallic complex represented by General Formula (G1) below.

However, in general formula (G1), each of R ¹ to R ⁴ is independently hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring. , represents either a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms forming a ring. R ⁵ to R ⁹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or It represents either 3 to 12 substituted or unsubstituted heteroaryl groups or cyano groups. Any one of R ⁶ to R ⁸ represents a cyano group. Moreover, L represents a monoanionic ligand. Moreover, n represents an integer of 1 to 3.

In the structure represented by General Formula (G1), n is 2.

In each of the above structures, the monoanionic ligand includes a monoanionic bidentate chelate ligand having a β-diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, a phenolic Monoanionic bidentate chelate ligands with a hydroxyl group, monoanionic bidentate chelate ligands in which both coordinating elements are nitrogen, or form metal-carbon bonds with iridium by cyclometallation Any one of aromatic heterocyclic bidentate ligands.

Further, in each of the above structures, the monoanionic ligand is any one of the following general formulas (L1) to (L8).

However, in the general formulas (L1) to (L8), R ⁷¹ to R ⁷⁷ and R ⁸⁷ to R ¹³¹ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, or a ring having 5 to 5 carbon atoms. 7 substituted or unsubstituted cycloalkyl group, halogen group, vinyl group, substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, substituted or unsubstituted It represents an alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. In addition, A ¹ to A ³ each independently represent an sp ^2- hybridized carbon bonding to nitrogen or hydrogen, or an sp ^2- hybridized carbon having a substituent, the substituent being an alkyl group having 1 to 6 carbon atoms, a halogen group, It represents either a haloalkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group.

In addition, n is 3 in the structure represented by General Formula (G1).

Another embodiment of the present invention is an organometallic complex represented by General Formula (G2) below.

However, in general formula (G2), each of R ¹ to R ⁴ is independently hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring. , represents either a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms forming a ring. R ⁵ to R ⁹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or represents any one of 3 to 12 substituted or unsubstituted heteroaryl groups or cyano groups, at least one of which represents a cyano group; R ⁷¹ and R ⁷³ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, a halogen group, a vinyl group, a substituted or an unsubstituted haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a ring having 6 carbon atoms to 13 substituted or unsubstituted aryl groups;

Another embodiment of the present invention is an organometallic complex represented by General Formula (G2) below.

However, in general formula (G2), each of R ¹ to R ⁴ is independently hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring. , represents either a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms forming a ring. R ⁵ to R ⁹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or It represents either 3 to 12 substituted or unsubstituted heteroaryl groups or cyano groups. Any one of R ⁶ to R ⁸ represents a cyano group. R ⁷¹ and R ⁷³ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, a halogen group, a vinyl group, a substituted or an unsubstituted haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a ring having 6 carbon atoms to 13 substituted or unsubstituted aryl groups;

Another aspect of the present invention is that the pyrimidine ring coordinated to Ir has at least one phenyl group having a cyano group as a substituent, and the phenyl group having a cyano group at the para- or meta-position is a pyrimidine It is an organometallic complex that binds to the 6-position of the ring.

Another embodiment of the present invention is an organometallic complex represented by Structural Formula (100).

Another aspect of the present invention is that the pyrimidine ring coordinated to Ir has at least one phenyl group having a cyano group as a substituent, and the phenyl group having a cyano group is bonded to the 6-position of the pyrimidine ring. It is a light-emitting element using an organometallic complex. Note that a light-emitting element including another organic compound in addition to the above organometallic complex is also included in one embodiment of the present invention.

Another embodiment of the present invention is a light-emitting element using the above-described organometallic complex of one embodiment of the present invention. Note that a light-emitting element formed using the organometallic complex of one embodiment of the present invention in an EL layer between a pair of electrodes and a light-emitting layer included in the EL layer is also included in one embodiment of the present invention. . In addition to light-emitting elements, light-emitting devices including transistors, substrates, and the like are also included in the scope of the invention. Furthermore, in addition to these light emitting devices, the scope of the invention also includes electronic devices and lighting devices having microphones, cameras, operation buttons, external connectors, housings, covers, support bases, speakers, and the like.

The organometallic complex that is one embodiment of the present invention can be used for a light-emitting layer of a light-emitting element in combination with another organic compound. That is, since it is possible to obtain light emission from the triplet excited state from the light emitting layer, it is possible to improve the efficiency of the light emitting device, which is very effective. Therefore, a light-emitting element in which an organometallic complex of one embodiment of the present invention is used in combination with another organic compound for a light-emitting layer is included in one embodiment of the present invention. Furthermore, in addition to the above, a structure in which a third substance is added to the light-emitting layer may be employed.

One embodiment of the present invention includes a light-emitting device including a light-emitting element, and further includes a lighting device including a light-emitting device. Accordingly, light-emitting devices herein refer to image display devices or light sources (including lighting devices). In addition, a module in which a connector such as FPC (Flexible printed circuit) or TCP (Tape Carrier Package) is attached to the light emitting device, a module in which a printed wiring board is provided at the end of TCP, or a COG (Chip On Glass) is attached to the light emitting device. All modules in which an IC (integrated circuit) is directly mounted are included in the light emitting device.

One embodiment of the present invention can provide a novel organometallic complex. Also, a novel organometallic complex having excellent heat resistance can be provided. In addition, it is possible to provide a novel organometallic complex that is difficult to decompose during sublimation. Further, one embodiment of the present invention can provide a novel organometallic complex with high color purity. Further, according to one embodiment of the present invention, a novel organometallic complex with high molecular orientation can be provided. Further, in one embodiment of the present invention, a novel organometallic complex that can be used for a light-emitting element can be provided. Further, one embodiment of the present invention can provide a novel organometallic complex that can be used for an EL layer of a light-emitting element. Further, a highly efficient and highly reliable novel light-emitting element using the novel organometallic complex which is one embodiment of the present invention can be provided. Further, a novel light-emitting device, a novel electronic device, or a novel lighting device can be provided. Note that the description of these effects does not preclude the existence of other effects. Note that one embodiment of the present invention does not necessarily have all of these effects. Effects other than these are self-evident from the descriptions of the specification, drawings, claims, etc., and it is possible to extract effects other than these from the descriptions of the specification, drawings, claims, etc. is.

4A and 4B illustrate the structure of a light-emitting element; 4A and 4B illustrate a light-emitting device; 4A and 4B illustrate a light-emitting device; 4A and 4B illustrate electronic devices; 1A and 1B illustrate electronic devices; A figure explaining a car. 4A and 4B illustrate a lighting device; ¹ H-NMR chart of the organometallic complex represented by Structural Formula (100). UV-visible absorption spectrum and emission spectrum in a solution of the organometallic complex represented by Structural Formula (100). 4A and 4B illustrate a light-emitting element; FIG. 4 is a diagram showing current density-luminance characteristics of Light-Emitting Element 1 and Comparative Light-Emitting Element 2; FIG. 4 is a diagram showing voltage-luminance characteristics of Light-Emitting Element 1 and Comparative Light-Emitting Element 2; FIG. 4 is a diagram showing luminance-current efficiency characteristics of Light-Emitting Element 1 and Comparative Light-Emitting Element 2; FIG. 4 is a diagram showing voltage-current characteristics of Light-Emitting Element 1 and Comparative Light-Emitting Element 2; FIG. 4 shows emission spectra of Light-Emitting Element 1 and Comparative Light-Emitting Element 2; FIG. 10 is a graph showing the reliability of Light-Emitting Element 1 and Comparative Light-Emitting Element 2; The figure which shows the measurement result by a quadrupole mass spectrometer. ¹ H-NMR chart of the organometallic complex represented by Structural Formula (112). UV-visible absorption spectrum and emission spectrum in a solution of the organometallic complex represented by Structural Formula (112). ¹ H-NMR chart of the organometallic complex represented by Structural Formula (114). UV-visible absorption spectrum and emission spectrum in a solution of the organometallic complex represented by Structural Formula (114).

Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. However, the present invention is not limited to the following description, and various changes in form and detail can be made without departing from the spirit and scope of the present invention. Therefore, the present invention should not be construed as being limited to the descriptions of the embodiments shown below.

Note that the position, size, range, etc. of each configuration shown in the drawings, etc. may not represent the actual position, size, range, etc. for ease of understanding. Therefore, the disclosed invention is not necessarily limited to the position, size, range, etc. disclosed in the drawings and the like.

Further, in this specification and the like, when describing the configuration of the invention using the drawings, the same reference numerals are commonly used between different drawings.

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

In the organometallic complex which is one embodiment of the present invention, the pyrimidine ring coordinated to Ir has at least one phenyl group having a cyano group as a substituent, and the phenyl group having a cyano group is 6 in the pyrimidine ring. It has a structure represented by the following general formula (G1), which is characterized by binding to a position.

In general formula (G1), R ¹ to R ⁴ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, a ring or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms forming a ring. R ⁵ to R ⁹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or represents any one of 3 to 12 substituted or unsubstituted heteroaryl groups or cyano groups, at least one of which represents a cyano group; Moreover, L represents a monoanionic ligand. Moreover, n represents an integer of 1 to 3.

An organometallic complex that is another embodiment of the present invention has a structure represented by General Formula (G1), wherein R ¹ to R ⁴ each independently represent hydrogen, It represents any one of an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. R ⁵ to R ⁹ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted hetero group having 3 to 12 carbon atoms. represents either an aryl group or a cyano group. Any one of R ⁶ to R ⁸ represents a cyano group. L represents a monoanionic ligand. Moreover, n represents an integer of 1 to 3.

In the organometallic complex that is another embodiment of the present invention, n is 2 in General Formula (G1).

In the organometallic complex that is another embodiment of the present invention, the monoanionic ligand in the general formula (G1) is a monoanionic bidentate chelate ligand having a β-diketone structure and a carboxyl group. a monoanionic bidentate chelate ligand with a phenolic hydroxyl group, a monoanionic bidentate chelate ligand with a phenolic hydroxyl , or an aromatic heterocyclic bidentate ligand that forms a metal-carbon bond with iridium upon cyclometallation.

Another embodiment of the present invention is an organometallic complex in which the monoanionic ligand in General Formula (G1) is represented by any one of General Formulas (L1) to (L8) below.

In general formulas (L1) to (L8), R ⁷¹ to R ⁷⁷ and R ⁸⁷ to R ¹³¹ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted group having 5 to 7 carbon atoms forming a ring. or unsubstituted cycloalkyl group, halogen group, vinyl group, substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, substituted or unsubstituted 1 carbon atom 6 to 6 alkylthio groups, or substituted or unsubstituted aryl groups having 6 to 13 carbon atoms forming a ring. In addition, A ¹ to A ³ each independently represent an sp ^2- hybridized carbon bonding to nitrogen or hydrogen, or an sp ^2- hybridized carbon having a substituent, the substituent being an alkyl group having 1 to 6 carbon atoms or a halogen group. , represents a haloalkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group.

In the organometallic complex that is another embodiment of the present invention, n is 3 in General Formula (G1).

An organometallic complex that is another embodiment of the present invention has a structure represented by General Formula (G2) below.

In general formula (G2), R ¹ to R ⁴ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, a ring or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms forming a ring. R ⁵ to R ⁹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or represents any one of 3 to 12 substituted or unsubstituted heteroaryl groups or cyano groups, at least one of which represents a cyano group; R ⁷¹ and R ⁷³ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, a halogen group, a vinyl group, a substituted or an unsubstituted haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a ring having 6 carbon atoms to 13 substituted or unsubstituted aryl groups;

An organometallic complex that is another embodiment of the present invention has a structure represented by General Formula (G2), wherein R ¹ to R ⁴ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or a ring represents either a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms forming R ⁵ to R ⁹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or It represents either 3 to 12 substituted or unsubstituted heteroaryl groups or cyano groups. Any one of R ⁶ to R ⁸ represents a cyano group. R ⁷¹ and R ⁷³ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, a halogen group, a vinyl group, a substituted or an unsubstituted haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a ring having 6 carbon atoms to 13 substituted or unsubstituted aryl groups;

In addition, in the organometallic complex represented by the general formula (G1) or the general formula (G2), the substitution preferably means a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a sec-butyl group, Alkyl groups having 1 to 6 carbon atoms such as tert-butyl, n-pentyl and n-hexyl, phenyl, o-tolyl, m-tolyl, p-tolyl, 1-naphthyl, It represents substitution with a substituent such as an aryl group having 6 to 12 carbon atoms such as a 2-naphthyl group, 2-biphenyl group, 3-biphenyl group and 4-biphenyl group. Moreover, these substituents may be bonded to each other to form a ring. For example, when the aryl group is a 2-fluorenyl group having two phenyl groups at the 9-position as substituents, the phenyl groups are bonded to each other to form a spiro-9,9'-bifluoren-2-yl group. can be More specific examples include phenyl group, tolyl group, xylyl group, biphenyl group, indenyl group, naphthyl group, fluorenyl group and the like.

Further, in the organometallic complexes represented by the general formula (G1) and the general formula (G2), specific examples of the alkyl group having 1 to 6 carbon atoms in R ¹ to R ⁹ in the formulas include a methyl group , ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, isobutyl group, tert-butyl group, pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, neopentyl group, hexyl group, isohexyl group , sec-hexyl group, tert-hexyl group, neohexyl group, 3-methylpentyl group, 2-methylpentyl group, 2-ethylbutyl group, 1,2-dimethylbutyl group, 2,3-dimethylbutyl group and the like. .

Further, in the organometallic complexes represented by the general formula (G1) and the general formula (G2), in the formulas, a substituted or unsubstituted group having 5 to 7 carbon atoms forming a ring in R ¹ to R ⁹ Specific examples of cycloalkyl groups include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and the like.

Further, in the organometallic complexes represented by the general formula (G1) and the general formula (G2), in the formulas, a substituted or unsubstituted group having 6 to 13 carbon atoms forming a ring in R ¹ to R ⁹ Specific examples of aryl groups include phenyl, biphenyl, naphthyl, indenyl, and fluorenyl groups.

Further, in the organometallic complexes represented by the general formula (G1) and the general formula (G2), in the formulas, a substituted or unsubstituted group having 3 to 12 carbon atoms forming a ring in R ¹ to R ⁹ Specific examples of heteroaryl groups include a triazinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridinyl group, a quinolinyl group, an isoquinolinyl group, a benzothienyl group, a benzofuranyl group, an indolyl group, a dibenzothienyl group, a dibenzofuranyl group, and a carbazolyl group. is mentioned.

Next, specific structural formulas of the above-described organometallic complexes of one embodiment of the present invention are shown below.

Note that the organometallic complexes represented by the structural formulas (100) to (134) are examples of the organometallic complexes represented by the general formula (G1), and the organometallic complexes of one embodiment of the present invention are , but not limited to this.

Next, an example of a method for synthesizing an organometallic complex that is one embodiment of the present invention is described. Note that the organometallic complex that is one embodiment of the present invention is represented by the following general formula (G1). Here, when n = 2 (general formula (G1-1) below), A method for synthesizing a complex and an organometallic complex having n=3 (general formula (G1-2) below) will be described.

<<Method for Synthesizing Pyrimidine Derivative Represented by General Formula (G0)>>
First, a method for synthesizing the pyrimidine derivative (general formula (G0)) included in the general formula (G1) is described.

A pyrimidine derivative represented by general formula (G0) below (ligand included in general formula (G1)) can be easily synthesized, for example, by the synthesis method described below. Here, three types of synthesizing methods, a first synthesizing method, a second synthesizing method, and a third synthesizing method, are shown.

In the above general formula (G0), R ¹ to R ⁴ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, It represents either a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms forming a ring. R ⁵ to R ⁹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or represents any one of 3 to 12 substituted or unsubstituted heteroaryl groups or cyano groups, at least one of which represents a cyano group;

<First synthesis method>
The pyrimidine derivative represented by the general formula (G0) is obtained by lithiating the halogenated benzene derivative (A1) with alkyllithium or the like to obtain a pyrimidine halide (A2), as shown in the synthesis scheme (A-1) below. It can be obtained by reacting.

In the above synthesis scheme (A-1), X ¹ and X ² represent halogen, and R ¹ to R ⁴ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, or a ring having 5 carbon atoms. to 7 substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms forming a ring, or substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms forming a ring represents any of the groups. R ⁵ to R ⁹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or represents any one of 3 to 12 substituted or unsubstituted heteroaryl groups or cyano groups, at least one of which represents a cyano group;

<Second synthesis method>
The pyrimidine derivative represented by the general formula (G0) is obtained by coupling a benzene derivative boronic acid (A1′) and a pyrimidine halide (A2′) as shown in the synthesis scheme (A-1′) below. can be obtained by

In the synthesis scheme (A-1') above, ^X3 represents a halogen, and ^B1 represents a boronic acid, a boronate ester, a cyclic triol borate salt, or the like. In addition to the lithium salt, the cyclic triol borate salt may be a potassium salt or a sodium salt. R ¹ to R ⁴ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, or a ring having 6 carbon atoms. It represents either a substituted or unsubstituted aryl group of up to 13 or a substituted or unsubstituted heteroaryl group of 3 to 12 carbon atoms forming a ring. R ⁵ to R ⁹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or represents any one of 3 to 12 substituted or unsubstituted heteroaryl groups or cyano groups, at least one of which represents a cyano group;

<Third synthesis method>
The pyrimidine derivative represented by the above general formula (G0) is prepared by combining a benzene derivative-substituted diketone (A1'') and formamide (A2'') with microwaves as shown in the synthesis scheme (A-1'') below. It can be obtained by reacting using

In the above synthesis scheme (A-1''), R ¹ to R ⁴ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted group having 5 to 7 carbon atoms forming a ring. represents either a cycloalkyl group, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms forming a ring. R ⁵ to R ⁹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or represents any one of 3 to 12 substituted or unsubstituted heteroaryl groups or cyano groups, at least one of which represents a cyano group;

Various types of the compounds (A1), (A2), (A1′), (A2′), (A1″), and (A2″) used in the above synthesis method are commercially available. , or can be synthesized, a large number of pyrimidine derivatives represented by the general formula (G0) can be easily synthesized. Therefore, the organometallic complex, which is one embodiment of the present invention, is characterized by having a wide variety of ligands.

<<Method for Synthesizing Organometallic Complex Represented by General Formula (G1-1)>>
A method for synthesizing the organometallic complex represented by General Formula (G1-1) will be described.

As shown in the synthesis scheme (A-2) below, the organometallic complex represented by the above general formula (G1-1) is a group 9 or group 10 metal compound containing a halogen (rhodium chloride hydrate, Palladium chloride, iridium chloride, iridium bromide, iridium iodide, potassium tetrachloroplatinate, etc.) and the pyrimidine derivative represented by the general formula (G0) are mixed with no solvent or an alcoholic solvent (glycerol, ethylene glycol, 2 -Methoxyethanol, 2-ethoxyethanol, etc.) alone, or using a mixed solvent of one or more alcoholic solvents and water, by heating in an inert gas atmosphere, an organic metal having a structure crosslinked with a halogen A multinuclear complex (B), which is a kind of complex and a novel substance, can be obtained. A heating means is not particularly limited, and an oil bath, a sand bath, or an aluminum block may be used. It is also possible to use microwaves as heating means.

In the above synthesis scheme (A-2), X represents a halogen, and R ¹ to R ⁴ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted group having 5 to 7 carbon atoms forming a ring. or an unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms forming a ring represents R ⁵ to R ⁹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or represents any one of 3 to 12 substituted or unsubstituted heteroaryl groups or cyano groups, at least one of which represents a cyano group;

Next, as shown in the synthesis scheme (A-3) below, the binuclear complex (B) obtained in the above synthesis scheme (A-2) and the raw material HL of the monoanionic ligand are combined with an inert By reacting in a gas atmosphere, the protons of HL are eliminated and L is coordinated to the central metal M, whereby an organometallic complex represented by general formula (G1-1) can be obtained. A heating means is not particularly limited, and an oil bath, a sand bath, or an aluminum block may be used. It is also possible to use microwaves as heating means.

In the above synthesis scheme (A-3), L represents a monoanionic ligand, X represents a halogen, R ¹ to R ⁴ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or a ring having 3 to 12 carbon atoms represents either a substituted or unsubstituted heteroaryl group. R ⁵ to R ⁹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or represents any one of 3 to 12 substituted or unsubstituted heteroaryl groups or cyano groups, at least one of which represents a cyano group;

<<Method for Synthesizing Organometallic Complex Represented by General Formula (G1-2)>>
A method for synthesizing the organometallic complex represented by General Formula (G1-2) is described.

As shown in the synthesis scheme (A-4) below, the organometallic complex represented by the general formula (G1-2) is an iridium compound containing a halogen (iridium chloride hydrate, iridium bromide, iridium iodide, iridium acetate, ammonium hexachloroiridate, etc.), or an organic iridium complex compound (acetylacetonato complex, diethyl sulfide complex, di-μ-chloro-bridged binuclear complex, di-μ-hydroxo-bridged binuclear complex, etc.), and the general formula A pyrimidine derivative represented by (G0) is mixed, dissolved in no solvent or in an alcoholic solvent (glycerol, ethylene glycol, 2-methoxyethanol, 2-ethoxyethanol, etc.), and then heated. be done.

In the above synthesis scheme (A-4), R ¹ to R ⁴ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring. group, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms forming a ring. R ⁵ to R ⁹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or represents any one of 3 to 12 substituted or unsubstituted heteroaryl groups or cyano groups, at least one of which represents a cyano group;

The methods for synthesizing the organometallic complexes represented by general formula (G1), general formula (G1-1), and general formula (G1-2) as organometallic complexes of one embodiment of the present invention have been described above. However, the present invention is not limited to this, and may be synthesized by other synthetic methods.

Further, with the use of the organometallic complex which is one embodiment of the present invention, a light-emitting element, a light-emitting device, an electronic device, or a lighting device with high emission efficiency can be realized. Further, a highly reliable light-emitting element, light-emitting device, electronic device, or lighting device can be realized.

Note that one embodiment of the present invention is described in this embodiment. In addition, one aspect of the present invention will be described in another embodiment. However, one embodiment of the present invention is not limited to these. In other words, since various aspects of the invention are described in this embodiment and other embodiments, one aspect of the invention is not limited to any particular aspect. For example, an example of application to a light-emitting element is described as one embodiment of the present invention, but one embodiment of the present invention is not limited thereto. Depending on circumstances, one embodiment of the present invention may be applied to elements other than light-emitting elements. Further, one embodiment of the present invention may not be applied to a light-emitting element depending on circumstances.

The structure described in this embodiment can be combined as appropriate with any of the structures described in other embodiments.

(Embodiment 2)
In this embodiment, a light-emitting element that is one embodiment of the present invention will be described. Note that the organometallic complex that is one embodiment of the present invention can be used for the light-emitting element described in this embodiment.

<<Basic structure of light-emitting element>>
FIG. 1A shows a light-emitting element in which an EL layer is sandwiched between a pair of electrodes. Specifically, it has a structure in which an EL layer 103 including a light-emitting layer is sandwiched between a first electrode 101 and a second electrode 102 .

In FIG. 1B, a plurality of (two layers in FIG. 1B) EL layers (103a and 103b) are provided between a pair of electrodes, and a charge generation layer 104 is sandwiched between the EL layers. A light-emitting element with a laminated structure (tandem structure) is shown. Such a tandem-structured light-emitting element can realize a light-emitting device that can be driven at a low voltage and has low power consumption.

Note that when a voltage is applied to the first electrode 101 and the second electrode 102, the charge generation layer 104 injects electrons into one EL layer (103a or 103b) and ) has a function of injecting holes. Therefore, in FIG. 1B, when a voltage is applied to the first electrode 101 so that the potential thereof is higher than that of the second electrode 102, electrons are injected from the charge generation layer 104 into the EL layer 103a and the EL layer 103b. holes are injected into

From the viewpoint of light extraction efficiency, the charge generation layer 104 preferably has a property of transmitting visible light (specifically, the charge generation layer 104 has a visible light transmittance of 40% or more). Also, the charge generation layer 104 functions even if the conductivity is lower than that of the first electrode 101 and the second electrode 102 .

FIG. 1C shows the stacked structure of the EL layer 103 . In FIG. 1C, when the first electrode 101 functions as an anode, the EL layer 103 includes a hole-injection layer 111, a hole-transport layer 112, and a hole-injection layer 111 over the first electrode 101. It has a structure in which a light-emitting layer 113, an electron-transporting layer 114, and an electron-injecting layer 115 are sequentially stacked. Even in the case of having a plurality of EL layers as in the tandem structure shown in FIG. 1B, each EL layer is stacked sequentially from the anode side as described above. Note that when the first electrode 101 is the cathode and the second electrode 102 is the anode, the stacking order is reversed.

Each of the light-emitting layers 113 included in the EL layers (103, 103a, and 103b) includes a light-emitting substance or an appropriate combination of a plurality of substances, and has a structure in which fluorescent light emission or phosphorescent light emission with a desired emission color can be obtained. be able to. Further, the light-emitting layer 113 may have a laminated structure with different emission colors. Note that in this case, different materials may be used for the light-emitting substances and other substances used in the stacked light-emitting layers. Alternatively, a structure in which different emission colors can be obtained from the plurality of EL layers (103a and 103b) shown in FIG. 1B may be employed. In this case also, different materials may be used for the light-emitting substances and other substances used in the respective light-emitting layers.

Further, in the light-emitting element which is one embodiment of the present invention, the emitted light emitted from the EL layers (103, 103a, and 103b) may be resonated between the electrodes to enhance the emitted light. 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, thereby forming a micro optical resonator (microcavity) structure and forming an EL layer. The luminescence obtained from 103 can be enhanced.

Note that when the first electrode 101 of the light-emitting element is a reflective electrode having a laminated structure of a reflective conductive material and a light-transmitting conductive material (transparent conductive film), the transparent conductive film Optical tuning can be achieved by controlling the thickness. Specifically, the inter-electrode distance between the first electrode 101 and the second electrode 102 is approximately mλ/2 (where m is a natural number) with respect to the wavelength λ of light obtained from the light-emitting layer 113. It is preferable to adjust

In order to amplify desired light (wavelength: λ) obtained from the light-emitting layer 113, the optical distance from the first electrode 101 to the region (light-emitting region) of the light-emitting layer 113 from which desired light is obtained, The optical distance from the second electrode 102 to the region (light emitting region) of the light emitting layer 113 where desired light is obtained is adjusted to be near (2m′+1)λ/4 (where m′ is a natural number). preferably. Note that the light-emitting region here means a recombination region of holes and electrons in the light-emitting layer 113 .

By performing such optical adjustment, the spectrum of specific monochromatic light obtained from the light-emitting layer 113 can be narrowed, and light emission with good color purity can be obtained.

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 reflection area of the first electrode 101 to the reflection area of the second electrode 102. can. However, since it is difficult to strictly determine the reflective regions in the first electrode 101 and the second electrode 102, it is possible to assume arbitrary positions of the first electrode 101 and the second electrode 102 as reflective regions. can sufficiently obtain the above effects. Strictly speaking, the optical distance between the first electrode 101 and the light-emitting layer from which desired light is obtained is the optical distance between the reflection region in the first electrode 101 and the light-emitting region in the light-emitting layer from which desired light is obtained. It can be said that it is the distance. However, since it is difficult to strictly determine the reflective region in the first electrode 101 and the light-emitting region in the light-emitting layer from which desired light can be obtained, an arbitrary position of the first electrode 101 can be used as the reflective region and the desired light-emitting region. By assuming that an arbitrary position of the light-emitting layer from which light is obtained is the light-emitting region, the above effects can be sufficiently obtained.

When the light-emitting element shown in FIG. 1C has a microcavity structure, light of different wavelengths (monochromatic light) can be extracted even if the EL layer is common. Therefore, separate coloring (for example, RGB) for obtaining different emission colors is not necessary, and high definition can be achieved. A combination with a colored layer (color filter) is also possible. In addition, since it is possible to increase the emission intensity of the specific wavelength in the front direction, it is possible to reduce power consumption.

Note that in the light-emitting element which is one embodiment of the present invention, at least one of the first electrode 101 and the second electrode 102 is a light-transmitting electrode (a transparent electrode, a semi-transmissive/semi-reflective electrode, or the like). do. When the light-transmitting electrode is a transparent electrode, the visible light transmittance of the transparent electrode is set to 40% or more. In the case of a semi-transmissive/semi-reflective electrode, the visible light reflectance of the semi-transmissive/semi-reflective electrode should be 20% or more and 80% or less, preferably 40% or more and 70% or less. Moreover, these electrodes preferably have a resistivity of 1×10 ⁻² Ωcm or less.

Further, in the light-emitting element of one embodiment of the present invention described above, when one of the first electrode 101 and the second electrode 102 is a reflective electrode (reflective electrode), the reflective electrode is visible. The light reflectance is 40% or more and 100% or less, preferably 70% or more and 100% or less. Moreover, the electrode preferably has a resistivity of 1×10 ⁻² Ωcm or less.

<<Specific Structure and Manufacturing Method of Light-Emitting Element>>
Next, a specific structure and a manufacturing method of a light-emitting element that is one embodiment of the present invention are described. In addition, in FIGS. 1A to 1E, when the reference numerals are the same, the description is also the same.

<First electrode and second electrode>
As materials for forming the first electrode 101 and the second electrode 102, the following materials can be used in appropriate combination as long as the functions of both electrodes in the above-described element structure can be satisfied. For example, metals, alloys, electrically conductive compounds, mixtures thereof, and the like can be used as appropriate. Specifically, In--Sn oxide (also referred to as ITO), In--Si--Sn oxide (also referred to as ITSO), In--Zn oxide, and In--W--Zn oxide are given. In addition, aluminum (Al), titanium (Ti), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), gallium (Ga), zinc (Zn ), indium (In), tin (Sn), molybdenum (Mo), tantalum (Ta), tungsten (W), palladium (Pd), gold (Au), platinum (Pt), silver (Ag), yttrium (Y ), neodymium (Nd), and alloys containing appropriate combinations thereof can also be used. In addition, elements belonging to Group 1 or Group 2 of the periodic table of elements not exemplified above (e.g., lithium (Li), cesium (Cs), calcium (Ca), strontium (Sr)), europium (Eu), ytterbium Rare earth metals such as (Yb), alloys containing an appropriate combination thereof, graphene, and the like can be used.

In the case where the light-emitting element shown in FIG. 1 includes the EL layer 103 having a stacked-layer structure as shown in FIG. A hole injection layer 111 and a hole transport layer 112 are sequentially laminated by a vacuum deposition method. Further, as in FIG. 1D, when a plurality of EL layers (103a and 103b) having a stacked structure are stacked with the charge generation layer 104 interposed therebetween and the first electrode 101 is an anode, the first electrode Not only are the hole injection layer 111a and the hole transport layer 112a of the EL layer 103a successively laminated on the EL layer 101 by vacuum evaporation, but also the EL layer 103a and the charge generation layer 104 are successively laminated on the EL layer 103a. A hole-injecting layer 111b and a hole-transporting layer 112b of the EL layer 103b are sequentially laminated on the layer 104 in the same manner.

<Hole injection layer and hole transport layer>
The hole injection layers (111, 111a, 111b) are layers for injecting holes from the first electrode 101, which is an anode, and the charge generation layer (104) into the EL layers (103, 103a, 103b). , which is a layer containing a material having a high hole injection property.

Materials with high hole injection properties include transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide. In addition, phthalocyanine compounds such as phthalocyanine (abbreviation: H ₂ Pc) and copper phthalocyanine (abbreviation: CuPC) can be used.

In addition, 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 (abbreviation: DPAB), N, N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: DNTPD), 1, 3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]- 9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N- Aromatic amine compounds such as (1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) and the like can be used.

In addition, poly(N-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)- N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD) and the like can be used. Alternatively, poly (3,4-ethylenedioxythiophene) / poly (styrene sulfonic acid) (abbreviation: PEDOT / PSS), polyaniline / poly (styrene sulfonic acid) (abbreviation: PAni / PSS), etc. Molecular compounds and the like can also be used.

A composite material containing a hole-transporting material and an acceptor material (electron-accepting material) can also be used as a material having a high hole-injecting property. In this case, electrons are withdrawn from the hole-transporting material by the acceptor material to generate holes in the hole-injecting layers (111, 111a, 111b), and through the hole-transporting layers (112, 112a, 112b). Holes are injected into the light-emitting layers (113, 113a, 113b). The hole injection layers (111, 111a, 111b) may be formed of a single layer made of a composite material containing a hole-transporting material and an acceptor material (electron-accepting material). The material and the acceptor material (electron-accepting material) may be laminated in separate layers.

The hole transport layers (112, 112a, 112b) transfer holes injected from the first electrode 101 and the charge generation layer 104 to the light emitting layers (113, 113a, 113b) transport layer. The hole-transporting layers (112, 112a, 112b) are layers containing a hole-transporting material. The hole-transporting material used for the hole-transporting layers (112, 112a, 112b) should have a HOMO level that is the same as or close to the HOMO level of the hole-injecting layers (111, 111a, 111b). is preferred.

As an acceptor material used for the hole injection layers (111, 111a, 111b), oxides of metals belonging to groups 4 to 8 of the periodic table can be used. Specific examples include molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide, and rhenium oxide. Among them, molybdenum oxide is particularly preferred because it is stable even in the atmosphere, has low hygroscopicity, and is easy to handle. In addition, organic acceptors such as quinodimethane derivatives, chloranil derivatives, and hexaazatriphenylene derivatives can be used. Specifically, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F ₄ -TCNQ), chloranil, 2,3,6,7,10,11 -Hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN) and the like can be used. In particular, a compound such as HAT-CN in which an electron-withdrawing group is bound to a condensed aromatic ring having a plurality of heteroatoms is thermally stable and preferable. In addition, [3] radialene derivatives having an electron-withdrawing group (especially a halogen group such as a fluoro group or a cyano group) are preferable because they have very high electron-accepting properties. 1,2,3-cyclopropanetriylidene tris[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α',α''-1,2,3-cyclopropanetriylidene tris [2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], α,α′,α″-1,2,3-cyclopropanetriylidenetris[2,3,4 , 5,6-pentafluorobenzeneacetonitrile] and the like.

As the hole-transporting material used for the hole-injecting layers (111, 111a, 111b) and the hole-transporting layers (112, 112a, 112b), substances having a hole mobility of 10 ⁻⁶ cm ² /Vs or more are used. preferable. Note that any substance other than these can be used as long as it has a higher hole-transport property than electron-transport property.

As the hole-transporting material, a material having a high hole-transporting property such as a π-electron-rich heteroaromatic compound (for example, a compound having a carbazole skeleton or a compound having a furan skeleton) or a compound having an aromatic amine skeleton is preferable.

Specific examples of hole-transporting materials include 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N′-bis(3 -methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (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-3 '-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), N-(9,9-dimethyl-9H-fluoren-2-yl)-N-{9,9-dimethyl-2- [N'-phenyl-N'-(9,9-dimethyl-9H-fluoren-2-yl)amino]-9H-fluoren-7-yl}phenylamine (abbreviation: DFLADFL), N-(9,9- Dimethyl-2-diphenylamino-9H-fluoren-7-yl)diphenylamine (abbreviation: DPNF), 2-[N-(4-diphenylaminophenyl)-N-phenylamino]spiro-9,9'-bifluorene (abbreviation: : DPASF), 4-phenyl-4′-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), 3-[4-(9-phenanthryl)-phenyl]-9-phenyl -9H-carbazole (abbreviation: PCPPn), 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-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluorene-2 -amine (abbreviation: PCBBiF), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4 '-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 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-phenylcarbazole-3 -yl)-N,N'-diphenylbenzene-1,3-diamine (abbreviation: PCA2B), N,N',N''-triphenyl-N,N',N''-tris(9-phenylcarbazole -3-yl)benzene-1,3,5-triamine (abbreviation: PCA3B), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl] Fluorene-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]spiro-9,9′-bifluoren-2-amine (abbreviation: PCBASF), 2-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]spiro-9,9′-bifluorene (abbreviation: PCASF), 2,7-bis[N-(4-diphenyl aminophenyl)-N-phenylamino]spiro-9,9′-bifluorene (abbreviation: DPA2SF), N-[4-(9H-carbazol-9-yl)phenyl]-N-(4-phenyl)phenylaniline ( abbreviation: YGA1BP), N,N'-bis[4-(carbazol-9-yl)phenyl]-N,N'-diphenyl-9,9-dimethylfluorene-2,7-diamine (abbreviation: YGA2F), etc. An aromatic amine compound or the like can be used. Also, 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 4,4′,4″-tris(carbazol-9-yl)triphenylamine ( TCTA), 4,4′,4″-tris[N-(1-naphthyl)-N-phenylamino]triphenylamine (abbreviation: 1-TNATA), 4,4′,4″-tris (N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: m- MTDATA), N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N -phenylamino]biphenyl (abbreviation: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4 ,4′-diamine (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B) and other compounds having an aromatic amine skeleton, 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4′-di(N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9 -Phenylcarbazole (abbreviation: CzTP), 3,3′-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 3-[N-(4-diphenylaminophenyl)-N-phenylamino]-9 -Phenylcarbazole (abbreviation: PCzDPA1), 3,6-bis[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA2), 3,6-bis[N-( 4-diphenylaminophenyl)-N-(1-naphthyl)amino]-9-phenylcarbazole (abbreviation: PCzTPN2), 3-[N-(9-phenylcarbazol-3-yl)-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: PCzPCN1), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: : TCPB), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA) and other compounds having a carbazole skeleton, 4,4′,4″-(benzene-1 ,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: : DBTFLP-III), 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV) and other compounds having a thiophene skeleton, 4,4 ',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II), 4-{3-[3-(9-phenyl-9H-fluoren-9-yl) Examples include compounds having a furan skeleton such as phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II).

Furthermore, poly(N-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)-N,N'-bis(phenyl)benzidine] (abbreviation: Polymer compounds such as Poly-TPD) can also be used.

However, the hole-transporting material is not limited to the above, and the hole-transporting layer (111, 111a, 111b) and the hole-transporting layer are formed by combining one or a plurality of known various materials as a hole-transporting material. (112, 112a, 112b). The hole transport layers (112, 112a, 112b) may each be formed from a plurality of layers. That is, for example, a first hole transport layer and a second hole transport layer may be laminated.

In the light-emitting element shown in FIG. 1D, the light-emitting layer 113a is formed over the hole-transport layer 112a of the EL layer 103a by a vacuum evaporation method. After the EL layer 103a and the charge generation layer 104 are formed, the light emitting layer 113b is formed on the hole transport layer 112b of the EL layer 103b by vacuum deposition.

<Light emitting layer>
The light-emitting layers (113, 113a, 113b, 113c) are layers containing light-emitting substances. Note that as the light-emitting substance, a substance that emits light of blue, purple, blue-violet, green, yellow-green, yellow, orange, red, or the like is used as appropriate. In addition, by using different light-emitting substances for the plurality of light-emitting layers (113a, 113b, and 113c), a structure in which different emission colors are exhibited (for example, white light emission obtained by combining complementary emission colors) can be obtained. . Furthermore, a laminated structure in which one light-emitting layer contains different light-emitting substances may be used.

In addition, the light-emitting layers (113, 113a, 113b, 113c) may contain one or more organic compounds (host material, assist material) in addition to the light-emitting substance (guest material). Note that an organometallic complex that is one embodiment of the present invention can be used as the light-emitting substance. As one or more kinds of organic compounds, one or both of the hole-transporting material and the electron-transporting material described in this embodiment can be used.

A light-emitting substance that can be used in the light-emitting layers (113, 113a, 113b, 113c) is not particularly limited, and a light-emitting substance that converts singlet excitation energy into light emission in the visible light region, or a light-emitting substance that converts triplet excitation energy into light in the visible light region. can be used. Examples of the light-emitting substance include the following.

Examples of light-emitting substances that convert singlet excitation energy into light emission include substances that emit fluorescence (fluorescent materials). quinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives, phenanthrene derivatives, naphthalene derivatives and the like. Pyrene derivatives are particularly preferred because they have a high emission quantum yield. Specific examples of pyrene derivatives include N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6 -diamine (abbreviation: 1,6mMemFLPAPrn), N,N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: : 1,6FLPAPrn), N,N'-bis(dibenzofuran-2-yl)-N,N'-diphenylpyrene-1,6-diamine (abbreviation: 1,6FrAPrn), N,N'-bis(dibenzothiophene -2-yl)-N,N'-diphenylpyrene-1,6-diamine (abbreviation: 1,6ThAPrn), N,N'-(pyrene-1,6-diyl)bis[(N-phenylbenzo[b ] naphtho[1,2-d]furan)-6-amine] (abbreviation: 1,6BnfAPrn), N,N′-(pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[ 1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-02), N,N′-(pyrene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho [1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03) and the like.

In addition, 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl- 9-anthryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenyl Stilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-( 9H-carbazol-9-yl)-4′-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-diphenyl-N-[4-(10-phenyl-9- anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), 4-(10-phenyl-9-anthryl)-4′-(9-phenyl-9H-carbazol-3-yl)triphenylamine ( abbreviation: PCBAPA), 4-[4-(10-phenyl-9-anthryl)phenyl]-4′-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPBA), perylene, 2 ,5,8,11-tetra(tert-butyl)perylene (abbreviation: TBP), N,N''-(2-tert-butylanthracene-9,10-diyldi-4,1-phenylene)bis[N, N',N'-triphenyl-1,4-phenylenediamine] (abbreviation: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazole -3-amine (abbreviation: 2PCAPPA), N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA) ) etc. can be used.

Examples of light-emitting substances that convert triplet excitation energy into light emission include substances that emit phosphorescence (phosphorescent materials) and thermally activated delayed fluorescence (TADF) materials that exhibit thermally activated delayed fluorescence. .

Phosphorescent materials include organic metal complexes, metal complexes (platinum complexes), rare earth metal complexes, and the like. Since these exhibit different emission colors (emission peaks) depending on the substance, they are appropriately selected and used as necessary.

Examples of phosphorescent materials that exhibit blue or green color and have an emission spectrum with a peak wavelength of 450 nm or more and 570 nm or less include the following substances.

For example, tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium (III ) (abbreviation: [Ir(mpptz-dmp) ₃ ]), tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazolato)iridium (III) (abbreviation: [Ir(Mptz) ₃ ]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazolato]iridium (III) (abbreviation: [Ir(iPrptz-3b) ₃ ]), tris 4H-triazole skeletons such as [3-(5-biphenyl)-5-isopropyl-4-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPr5btz) ₃ ]), tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(Mptz1-mp) ₃ ]), 1H-triazoles such as tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Prptz1-Me) ₃ ]) organometallic complex having a skeleton, fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridium (III) (abbreviation: [Ir(iPrpmi) ₃ ]), tris[3- (2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium (III) (abbreviation: [Ir(dmpimpt-Me) ₃ ]) having an imidazole skeleton metal complex, bis[2-(4′,6′-difluorophenyl)pyridinato-N,C ^2′ ]iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4′, 6′-difluorophenyl)pyridinato-N,C ^2′ ]iridium (III) picolinate (abbreviation: FIrpic), bis{2-[3′,5′-bis(trifluoromethyl)phenyl]pyridinato-N,C ^{2 '} } iridium (III) picolinate (abbreviation: [Ir(CF ₃ ppy) ₂ (pic)]), bis[2-(4′,6′-difluorophenyl)pyridinato-N,C ^2′ ]iridium (III) Organometallic complexes in which a phenylpyridine derivative having an electron-withdrawing group such as acetylacetonate (abbreviation: FIracac) is used as a ligand.

Examples of phosphorescent materials that exhibit green or yellow color and have an emission spectrum with a peak wavelength of 495 nm or more and 590 nm or less include the following substances.

For example, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mpm) ₃ ]), tris(4-t-butyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm) ₃ ]), (acetylacetonato)bis(6-methyl-4-phenylpyrimidinato)iridium (III) (abbreviation: [Ir(mppm) ₂ (acac)]), ( acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm) ₂ (acac)]), (acetylacetonato)bis[6-(2- norbornyl)-4-phenylpyrimidinato]iridium (III) (abbreviation: [Ir(nbppm) ₂ (acac)]), (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4 -phenylpyrimidinato]iridium(III) (abbreviation: [Ir(mpmpm) ₂ (acac)]), (acetylacetonato)bis{4,6-dimethyl-2-[6-(2,6-dimethylphenyl )-4-pyrimidinyl-κN]phenyl-κC}iridium (III) (abbreviation: [Ir(dmpm-dmp) ₂ (acac)]), (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium (III) (abbreviation: [Ir(dppm) ₂ (acac)]), an organometallic complex having a pyrimidine skeleton such as (acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium ( III) (abbreviation: [Ir(mppr-Me) ₂ (acac)]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazinato)iridium (III) (abbreviation: [Ir (mppr-iPr) ₂ (acac)]), an organometallic complex having a pyrazine skeleton such as tris(2-phenylpyridinato-N,C ^2′ ) iridium (III) (abbreviation: [Ir(ppy) ₃ ]), bis(2-phenylpyridinato-N,C ^2′ )iridium (III) acetylacetonate (abbreviation: [Ir(ppy) ₂ (acac)]), bis(benzo[h]quinolinato)iridium ( III) acetylacetonate (abbreviation: [Ir(bzq) ₂ (acac)]), tris(benzo[h]quinolinato)iridium (III) (abbreviation: [Ir(bzq) ₃ ]), tris(2-phenylquino linato-N,C ^2′ )iridium(III) (abbreviation: [Ir(pq) ₃ ]), bis(2-phenylquinolinato-N,C ^2′ )iridium(III) acetylacetonate (abbreviation: [Ir (pq) ₂ (acac)]), bis(2,4-diphenyl-1,3-oxazolato-N,C ^2′ )iridium (III) acetylacetonate (abbreviation: [Ir(dpo) ₂ (acac)]), bis{2-[4′-(perfluorophenyl)phenyl]pyridinato-N,C ^2′ }iridium(III) acetylacetonate (abbreviation: [Ir(p- PF-ph) ₂ (acac)]), bis(2-phenylbenzothiazolato-N,C ^2′ ) iridium (III) acetylacetonate (abbreviation: [Ir(bt) ₂ (acac)]), etc. In addition to organometallic complexes, rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [Tb(acac) ₃ (Phen)]) can be used.

Examples of phosphorescent materials that exhibit yellow or red color and have an emission spectrum with a peak wavelength of 570 nm or more and 750 nm or less include the following substances.

For example, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium (III) (abbreviation: [Ir (5mdppm) ₂ (dibm)]), bis[4,6-bis ( 3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium (III) (abbreviation: [Ir(5mdppm) ₂ (dpm)]), (dipivaloylmethanato)bis[4,6-di(naphthalene- 1-yl)pyrimidinato]iridium(III) (abbreviation: [Ir(d1npm) ₂ (dpm)]), an organometallic complex having a pyrimidine skeleton, (acetylacetonato)bis(2,3,5-triphenyl pyrazinato)iridium (III) (abbreviation: [Ir(tppr) ₂ (acac)]), bis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium (III) (abbreviation: : [Ir(tppr) ₂ (dpm)]), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq) ₂ (acac)] ) and organometallic complexes having a pyrazine skeleton such as tris(1-phenylisoquinolinato-N,C ^2′ )iridium (III) (abbreviation: [Ir(piq) ₃ ]), bis(1-phenyliso Organometallic complexes having a pyridine skeleton such as quinolinato-N,C ^2′ )iridium (III) acetylacetonate (abbreviation: [Ir(piq) ₂ (acac)]), 2,3,7,8,12 , 13,17,18-octaethyl-21H,23H-porphyrin platinum (II) (abbreviation: [PtOEP]), platinum complexes such as tris(1,3-diphenyl-1,3-propanedionate) (monophenanthroline ) europium (III) (abbreviation: [Eu(DBM) ₃ (Phen)]), tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline) europium (III) ( Abbreviations: [Eu(TTA) ₃ (Phen)]) and other rare earth metal complexes.

As the organic compound (host material, assist material) used in the light-emitting layers (113, 113a, 113b, 113c), one or more substances having an energy gap larger than that of the light-emitting substance (guest material) are selected. You can use it. It should be noted that the materials exemplified as the hole-transporting materials described above and the materials exemplified as the electron-transporting materials described later can also be used as such an organic compound (host material, assist material).

When the light-emitting substance is a fluorescent material, an organic compound having a high singlet excited energy level and a low triplet excited energy level is preferably used as the host material. Note that in addition to the hole-transporting material and the electron-transporting material described in this embodiment, a bipolar material can be used as the host material, but any substance that satisfies the above conditions is more preferable. For example, anthracene derivatives and tetracene derivatives are also suitable.

Therefore, host materials combined with fluorescent light-emitting substances include, for example, 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA), PCPN, CzPA, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl] -benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-{4-(9-phenyl-9H-fluoren-9-yl)biphenyl-4′-yl}anthracene (abbreviation: FLPPA), 5,12-diphenyltetracene, 5,12-bis(biphenyl-2-yl)tetracene and the like.

When the light-emitting substance is a phosphorescent material, an organic compound having triplet excitation energy higher than the triplet excitation energy (the energy difference between the ground state and the triplet excited state) of the light-emitting substance may be selected as the host material. Note that in addition to the hole-transporting material and the electron-transporting material described in this embodiment, a bipolar material can be used as the host material, but any substance that satisfies the above conditions is more preferable. For example, condensed polycyclic aromatic compounds such as anthracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives, and dibenzo[g,p]chrysene derivatives are also suitable.

Therefore, host materials combined with a phosphorescent light-emitting substance include, for example, 9,10-diphenylanthracene (abbreviation: DAnth), N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl] -9H-carbazol-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), YGAPA, PCAPA, PCAPBA, N-(9,10-diphenyl-2) -anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), 6,12-dimethoxy-5,11-diphenylchrysene, N,N,N',N',N'', N″,N′″,N′″-octaphenyldibenzo[g,p]chrysene-2,7,10,15-tetramine (abbreviation: DBC1), CzPA,3,6-diphenyl-9-[ 4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9,10-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) and the like.

In the case where a plurality of organic compounds are used for the light-emitting layers (113, 113a, 113b, and 113c), it is preferable to mix a compound that forms an exciplex with a phosphorescent substance. Note that with such a structure, light emission using ExTET (Exciplex-Triplet Energy Transfer), which is energy transfer from an exciplex to a light-emitting substance, can be obtained. In this case, various organic compounds can be used in combination as appropriate. transportable materials) are particularly preferred.

A TADF material is a material that can up-convert (reverse intersystem crossing) a triplet excited state to a singlet excited state with a small amount of thermal energy, and efficiently exhibits light emission (fluorescence) from the singlet excited state. be. In addition, as a condition for efficiently obtaining thermally activated delayed fluorescence, the energy difference between the triplet excitation level and the singlet excitation level is 0 eV or more and 0.2 eV or less, preferably 0 eV or more and 0.1 eV or less. mentioned. In addition, delayed fluorescence in the TADF material refers to light emission having a spectrum similar to that of normal fluorescence and having a significantly long lifetime. Its lifetime is 10 ⁻⁶ seconds or more, preferably 10 ⁻³ seconds or more.

Examples of TADF materials include fullerenes and derivatives thereof, acridine derivatives such as proflavine, and eosin. Also included are metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd). Examples of metal-containing porphyrins include protoporphyrin-tin fluoride complex (SnF ₂ (Proto IX)), mesoporphyrin-tin fluoride complex (SnF ₂ (Meso IX)), hematoporphyrin-tin fluoride complex (SnF ₂ (Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complex (SnF ₂ (Copro III-4Me)), octaethylporphyrin-tin fluoride complex (SnF ₂ (OEP)), ethioporphyrin-tin fluoride complex (SnF ₂ (Etio I)), octaethylporphyrin-platinum chloride complex (PtCl ₂ OEP), and the like.

Other TADF materials include 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine ( Abbreviations: PIC-TRZ), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3, 5-triazine (abbreviation: PCCzPTzn), 2-[4-(10H-phenoxazin-10-yl)phenyl]-4,6-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: ACRXTN), 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. A heterocyclic compound having a ring can be used. In a substance in which a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring are directly bonded, both the donor property of the π-electron-rich heteroaromatic ring and the acceptor property of the π-electron-deficient heteroaromatic ring are strengthened. , is particularly preferable because the energy difference between the singlet excited state and the triplet excited state is small.

In addition, when using a TADF material, it can also be used in combination with other organic compounds.

The light-emitting layers (113, 113a, 113b, and 113c) can be formed by appropriately using the above materials. Further, the above materials can be used for forming the light-emitting layers (113, 113a, 113b, 113c) by combining them with low-molecular-weight materials or high-molecular-weight materials.

In the light-emitting element shown in FIG. 1D, the electron-transport layer 114a is formed over the light-emitting layer 113a of the EL layer 103a. After the EL layer 103a and the charge generation layer 104 are formed, the electron transport layer 114b is formed on the light emitting layer 113b of the EL layer 103b.

<Electron transport layer>
The electron transport layers (114, 114a, 114b) use the electron injection layers (115, 115a, 115b) to transfer electrons injected from the second electrode 102 and the charge generation layer (104) to the light emitting layers (113, 113a, 113b). ). The electron-transporting layers (114, 114a, 114b) are layers containing an electron-transporting material. The electron-transporting material used for the electron-transporting layers (114, 114a, 114b) preferably has an electron mobility of 1×10 ⁻⁶ cm ² /Vs or more. Note that any substance other than these substances can be used as long as it has a higher electron-transport property than hole-transport property.

Examples of electron-transporting materials include metal complexes having a quinoline skeleton, metal complexes having a benzoquinoline skeleton, metal complexes having an oxazole skeleton, metal complexes having a thiazole skeleton, oxadiazole derivatives, triazole derivatives, imidazole derivatives, π electron deficient including oxazole derivatives, thiazole derivatives, phenanthroline derivatives, quinoline derivatives with quinoline ligands, benzoquinoline derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, pyridine derivatives, bipyridine derivatives, pyrimidine derivatives, and other nitrogen-containing heteroaromatic compounds A material having a high electron transport property such as a type heteroaromatic compound can be used.

Specific examples of electron-transporting materials include tris(8-quinolinolato)aluminum(III) (abbreviation: Alq ₃ ), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq ₃ ), bis( 10-hydroxybenzo[h]quinolinato)beryllium (II) (abbreviation: BeBq ₂ ), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum (III) (abbreviation: BAlq), bis(8 -quinolinolato) zinc (II) (abbreviation: Znq) and other metal complexes having a quinoline skeleton or benzoquinoline skeleton, bis[2-(2-benzoxazolyl)phenolato]zinc (II) (abbreviation: ZnPBO), bis oxazole skeletons such as [2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), bis[2-(2-hydroxyphenyl)benzothiazolato]zinc(II) (abbreviation: Zn(BTZ) ₂ ), or Examples thereof include metal complexes having a thiazole skeleton.

In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-( p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-7-enyl-1,3,4-oxadi azol-2-yl)phenyl]-9H-carbazole (abbreviation: CO11) and other oxadiazole derivatives, 3-(4′-tert-butylphenyl)-4-phenyl-5-(4″-biphenyl)- 1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: : p-EtTAZ) and other triazole derivatives, 2,2′,2″-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[ 3-(Dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II) and other imidazole derivatives (including benzimidazole derivatives), and 4,4′-bis(5- oxazole derivatives such as methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs), bathophenanthroline (abbreviation: Bphen), bathocuproine (abbreviation: BCP), 2,9-bis(naphthalen-2-yl)-4,7 -phenanthroline derivatives such as diphenyl-1,10-phenanthroline (abbreviation: NBphen), 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-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]quinoxaline (abbreviation: 2mCzBPDBq), 2-[4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq) -III), 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPDBq-II), and 6-[3-(dibenzothiophen-4-yl)phenyl ] quinoxaline derivatives such as dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II), or dibenzoquinoxaline derivatives, 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy) , 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB) and other pyridine derivatives, 4,6-bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazol-9-yl)phenyl ] Pyrimidine derivatives such as pyrimidine (abbreviation: 4,6mCzP2Pm), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6 A triazine derivative such as -diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn) can be used.

In addition, 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-BPy) Molecular compounds can also be used.

Further, the electron transport layers (114, 114a, 114b) are not limited to a single layer, and may have a structure in which two or more layers made of the above substances are laminated.

Next, in the light-emitting element shown in FIG. 1D, an electron-injecting layer 115a is formed over the electron-transporting layer 114a of the EL layer 103a by a vacuum evaporation method. After that, the EL layer 103a and the charge generation layer 104 are formed, and after the electron transport layer 114b of the EL layer 103b is formed, the electron injection layer 115b is formed thereon by vacuum deposition.

<Electron injection layer>
The electron injection layers (115, 115a, 115b) are layers containing substances with high electron injection properties. The electron injection layers (115, 115a, 115b) include alkali metals and alkalis such as lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride ( _CaF2 ), lithium oxide ( _LiOx ), and the like. Earth metals or their compounds can be used. Also, rare earth metal compounds such as erbium fluoride (ErF ₃ ) can be used. Electride may also be used for the electron injection layers (115, 115a, 115b). Examples of the electride include a mixed oxide of calcium and aluminum to which electrons are added at a high concentration. In addition, the substance which comprises the electron transport layer (114, 114a, 114b) mentioned above can also be used.

A composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layers (115, 115a, 115b). Such a composite material has excellent electron-injecting and electron-transporting properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material excellent in transporting generated electrons. Specifically, for example, an electron-transporting material (metal complex and heteroaromatic compounds) can be used. As the electron donor, any substance can be used as long as it exhibits an electron donating property with respect to an organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples include lithium, cesium, magnesium, calcium, erbium, and ytterbium. Further, alkali metal oxides and alkaline earth metal oxides are preferred, and examples thereof include lithium oxide, calcium oxide and barium oxide. Lewis bases such as magnesium oxide can also be used. An organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used.

Note that in the case of amplifying light obtained from the light-emitting layer 113b in the light-emitting element illustrated in FIG. It is preferably formed to be less than 1/4 of the wavelength λ. In this case, it can be adjusted by changing the film thickness of the electron transport layer 114b or the electron injection layer 115b.

<Charge generation layer>
In the light-emitting element shown in FIG. 1D, the charge generation layer 104 generates electrons in the EL layer 103a when a voltage is applied between the first electrode (anode) 101 and the second electrode (cathode) 102. to inject holes into the EL layer 103b. The charge-generating layer 104 may have a structure in which an electron acceptor (acceptor) is added to the hole-transporting material or a structure in which an electron donor (donor) is added to the electron-transporting material. good. Also, both of these configurations may be stacked. Note that by forming the charge-generating layer 104 using the above material, an increase in driving voltage in the case where EL layers are stacked can be suppressed.

In the case where the charge-generating layer 104 has a structure in which an electron acceptor is added to a hole-transporting material, the material described in this embodiment mode can be used as the hole-transporting material. Examples of electron acceptors include 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F ₄ -TCNQ) and chloranil. In addition, oxides of metals belonging to groups 4 to 8 in the periodic table can be mentioned. Specific examples include vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide.

In the case where the charge-generating layer 104 has a structure in which an electron donor is added to an electron-transporting material, the materials described in this embodiment can be used as the electron-transporting material. As the electron donor, alkali metals, alkaline earth metals, rare earth metals, metals belonging to groups 2 and 13 in the periodic table, oxides and carbonates thereof can be used. Specifically, it is preferable to use lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), ytterbium (Yb), indium (In), lithium oxide, cesium carbonate, or the like. Alternatively, an organic compound such as tetrathianaphthacene may be used as an electron donor.

<Substrate>
The light-emitting element described in this embodiment can be formed over various substrates. Note that the type of substrate is not limited to a specific one. Examples of substrates include semiconductor substrates (e.g. single crystal substrates or silicon substrates), SOI substrates, glass substrates, quartz substrates, plastic substrates, metal substrates, stainless steel substrates, substrates with stainless steel foil, tungsten substrates, Substrates with tungsten foils, flexible substrates, laminated films, papers containing fibrous materials, or substrate films may be mentioned.

Examples of materials for the glass substrate include barium borosilicate glass, aluminoborosilicate glass, soda lime glass, and the like. Examples of flexible substrates, laminated films, and base films include plastics such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), and polyethersulfone (PES), and acrylic resins. Synthetic resin, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyamide, polyimide, aramid resin, epoxy resin, inorganic deposition film, paper, and the like.

Note that a vacuum process such as an evaporation method or a solution process such as a spin coating method or an inkjet method can be used for manufacturing the light-emitting element described in this embodiment mode. When vapor deposition is used, physical vapor deposition (PVD) such as sputtering, ion plating, ion beam vapor deposition, molecular beam vapor deposition, vacuum vapor deposition, or chemical vapor deposition (CVD) is used. be able to. In particular, the functional layers (hole injection layers (111, 111a, 111b), hole transport layers (112, 112a, 112b), light emitting layers (113, 113a, 113b, 113c), electron transport layers included in the EL layer of the light emitting device) Layers (114, 114a, 114b), electron injection layers (115, 115a, 115b)), and charge generation layers (104, 104a, 104b) may be formed by a vapor deposition method (vacuum vapor deposition method, etc.), a coating method (dip coating method, etc.). , 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, flexographic (letterpress printing) method, gravure method, microcontact method, nanoimprint method, etc.).

Note that each functional layer (hole-injection layers (111, 111a, 111b) and hole-transport layers (112, 112a, 112b) constituting the EL layers (103, 103a, 103b) of the light-emitting element described in this embodiment mode , light-emitting layers (113, 113a, 113b, 113c), electron-transporting layers (114, 114a, 114b), electron-injecting layers (115, 115a, 115b)) and charge-generating layers (104, 104a, 104b). The materials are not limited, and other materials can be used in combination as long as they can satisfy the functions of each layer. Examples include polymer compounds (oligomers, dendrimers, polymers, etc.), middle-molecular-weight compounds (compounds in the intermediate region between low-molecular-weight and high-molecular-weight compounds: molecular weight 400 to 4000), inorganic compounds (quantum dot materials, etc.), and the like. can. As the quantum dot material, a colloidal quantum dot material, an alloy quantum dot material, a core-shell quantum dot material, a core quantum dot material, or the like can be used.

The structure described in this embodiment can be combined as appropriate with any of the structures described in other embodiments.

(Embodiment 3)
In this embodiment, a light-emitting device that is one embodiment of the present invention will be described. Note that the light-emitting device shown in FIG. 2A is an active matrix light-emitting device in which a transistor (FET) 202 over a first substrate 201 and light-emitting elements (203R, 203G, 203B, and 203W) are electrically connected. In the device, a plurality of light emitting elements (203R, 203G, 203B, 203W) have a common EL layer 204, and the optical distance between the electrodes of each light emitting element varies depending on the color of light emitted from each light emitting element. It has a tuned microcavity structure. In addition, it is a top emission light emitting device in which light emitted from the EL layer 204 is emitted through color filters (206R, 206G, 206B) formed on the second substrate 205. FIG.

In the light-emitting device shown in FIG. 2A, the first electrode 207 is formed to function as a reflective electrode. Also, the second electrode 208 is formed so as to function as a semi-transmissive/semi-reflective electrode. Note that electrode materials for forming the first electrode 207 and the second electrode 208 may be appropriately used with reference to the description of other embodiments.

Further, in FIG. 2A, for example, when the light emitting element 203R is a red light emitting element, the light emitting element 203G is a green light emitting element, the light emitting element 203B is a blue light emitting element, and the light emitting element 203W is a white light emitting element, the light emitting element 203W is a white light emitting element. ), the light emitting element 203R is adjusted so that the optical distance between the first electrode 207 and the second electrode 208 is 200R, and the light emitting element 203G is adjusted so that the first electrode 207 and the second electrode 208 is adjusted to have an optical distance of 200G, and the light emitting element 203B is adjusted to have an optical distance of 200B between the first electrode 207 and the second electrode 208 . Note that as shown in FIG. 2B, optical adjustment can be performed by stacking a conductive layer 210R over the first electrode 207 in the light emitting element 203R and stacking a conductive layer 210G in the light emitting element 203G.

Color filters ( 206 R, 206 G, 206 B) are formed on the second substrate 205 . Note that the color filter is a filter that allows a specific wavelength range of visible light to pass through and blocks a specific wavelength range of visible light. Therefore, as shown in FIG. 2A, by providing a color filter 206R that passes only the red wavelength band at a position overlapping with the light emitting element 203R, red light emission can be obtained from the light emitting element 203R. Further, by providing a color filter 206G that allows only the green wavelength band to pass through at a position overlapping with the light emitting element 203G, green light emission can be obtained from the light emitting element 203G. Further, by providing a color filter 206B that allows only a blue wavelength band to pass through at a position overlapping with the light emitting element 203B, blue light emission can be obtained from the light emitting element 203B. However, the light emitting element 203W can emit white light without providing a color filter. A black layer (black matrix) 209 may be provided at the end of one type of color filter. Furthermore, the color filters (206R, 206G, 206B) and black layer 209 may be covered with an overcoat layer using a transparent material.

FIG. 2A shows a light-emitting device having a structure (top emission type) for extracting light from the second substrate 205 side, but the first substrate provided with the FET 202 is used as shown in FIG. 2C. A light emitting device having a structure (bottom emission type) in which light is extracted to the 201 side may be used. Note that in the case of a bottom emission type light emitting device, the first electrode 207 is formed to function as a semi-transmissive/half-reflective electrode, and the second electrode 208 is formed to function as a reflective electrode. At least a translucent substrate is used as the first substrate 201 . Further, the color filters (206R', 206G', 206B') may be provided closer to the first substrate 201 than the light emitting elements (203R, 203G, 203B) as shown in FIG. 2C.

FIG. 2A shows the case where the light-emitting element is a red-light-emitting element, a green-light-emitting element, a blue-light-emitting element, or a white-light-emitting element; however, the light-emitting element that is one embodiment of the present invention is limited to these structures. However, a structure including a yellow light-emitting element or an orange light-emitting element may be used. Materials used for the EL layer (light-emitting layer, hole-injection layer, hole-transport layer, electron-transport layer, electron-injection layer, charge-generating layer, etc.) for manufacturing these light-emitting elements include other materials. The description of the form may be referred to and used as appropriate. In that case, it is also necessary to appropriately select a color filter according to the emission color of the light emitting element.

With the structure as described above, a light-emitting device including a light-emitting element emitting light of a plurality of colors can be obtained.

Note that the structure described in this embodiment can be used in combination with any of the structures described in other embodiments as appropriate.

(Embodiment 4)
In this embodiment, a light-emitting device that is one embodiment of the present invention will be described.

By applying the element structure of the light-emitting element which is one embodiment of the present invention, an active matrix light-emitting device or a passive matrix light-emitting device can be manufactured. Note that an active matrix light-emitting device has a structure in which a light-emitting element and a transistor (FET) are combined. Therefore, both a passive matrix light-emitting device and an active matrix light-emitting device are included in one embodiment of the present invention. Note that the light-emitting element described in any of the other embodiments can be applied to the light-emitting device described in this embodiment.

In this embodiment mode, an active matrix light-emitting device will be described with reference to FIGS.

3A is a top view showing the light emitting device 21, and FIG. 3B is a cross-sectional view taken along the chain line A-A' in FIG. 3A. The active matrix light emitting device includes a pixel portion 302, a driver circuit portion (source line driver circuit) 303, and driver circuit portions (gate line driver circuits) (304a and 304b) provided over a first substrate 301. . The pixel portion 302 and the driver circuit portions (303, 304a, 304b) are sealed between the first substrate 301 and the second substrate 306 with a sealing material 305. FIG.

Further, a lead wiring 307 is provided on the first substrate 301 . The routing wiring 307 is electrically connected to the FPC 308 which is an external input terminal. Note that the FPC 308 transmits external signals (for example, video signals, clock signals, start signals, reset signals, etc.) and potentials to the drive circuit units (303, 304a, 304b). Also, a printed wiring board (PWB) may be attached to the FPC 308 . The state in which these FPCs and PWBs are attached is included in the light emitting device.

Next, FIG. 3B shows a cross-sectional structure.

The pixel portion 302 is formed of a plurality of pixels having a FET (switching FET) 311 , a FET (current control FET) 312 , and a first electrode 313 electrically connected to the FET 312 . Note that the number of FETs included in each pixel is not particularly limited, and can be appropriately provided as necessary.

The FETs 309, 310, 311, and 312 are not particularly limited, and for example, staggered or reverse staggered transistors can be applied. Moreover, a transistor structure such as a top-gate type or a bottom-gate type may be used.

The crystallinity of semiconductors that can be used for these FETs 309, 310, 311, and 312 is not particularly limited. or a semiconductor partially having a crystal region) may be used. Note that it is preferable to use a crystalline semiconductor because deterioration of transistor characteristics can be suppressed.

Moreover, as these semiconductors, for example, Group 14 elements, compound semiconductors, oxide semiconductors, organic semiconductors, and the like can be used. Typically, a semiconductor containing silicon, a semiconductor containing gallium arsenide, an oxide semiconductor containing indium, or the like can be used.

The drive circuit section 303 has an FET 309 and an FET 310 . Note that the FET 309 and FET 310 may be formed of a circuit including a unipolar (either N-type or P-type) transistor, or may be formed of a CMOS circuit including an N-type transistor and a P-type transistor. can be Further, a structure having an external driving circuit may be employed.

An end of the first electrode 313 is covered with an insulator 314 . Note that for the insulator 314, an organic compound such as a negative photosensitive resin or a positive photosensitive resin (acrylic resin) or an inorganic compound such as silicon oxide, silicon oxynitride, or silicon nitride can be used. . Preferably, the insulator 314 has a curved surface with a curvature at the upper end or the lower end. Accordingly, the coverage of the film formed over the insulator 314 can be improved.

An EL layer 315 and a second electrode 316 are stacked over the first electrode 313 . The EL layer 315 has a light-emitting layer, a hole-injection layer, a hole-transport layer, an electron-transport layer, an electron-injection layer, a charge generation layer, and the like.

Note that the structure and materials described in other embodiments can be applied to the structure of the light-emitting element 317 described in this embodiment. Although not shown here, the second electrode 316 is electrically connected to the FPC 308 which is an external input terminal.

Although only one light-emitting element 317 is illustrated in the cross-sectional view of FIG. 3B, a plurality of light-emitting elements are arranged in matrix in the pixel portion 302 . In the pixel portion 302, light-emitting elements capable of emitting light of three types (R, G, and B) are selectively formed, whereby a light-emitting device capable of full-color display can be formed. In addition to the light-emitting elements that can emit light of three types (R, G, and B), for example, light-emitting elements that can emit light of white (W), yellow (Y), magenta (M), cyan (C), etc. elements may be formed. For example, by adding a light-emitting element capable of emitting light of several types described above to a light-emitting element capable of emitting light of three types (R, G, B), effects such as improvement of color purity and reduction of power consumption can be obtained. can be done. Further, a light-emitting device capable of full-color display may be obtained by combining with a color filter. As types of color filters, red (R), green (G), blue (B), cyan (C), magenta (M), yellow (Y), and the like can be used.

The FETs (309, 310, 311, 312) and the light-emitting element 317 on the first substrate 301 are formed by bonding the second substrate 306 and the first substrate 301 together with the sealing material 305. 301 , a second substrate 306 , and a space 318 surrounded by a sealant 305 . Note that the space 318 may be filled with an inert gas (nitrogen, argon, or the like) or an organic substance (including the sealant 305).

Epoxy resin or glass frit can be used for the sealant 305 . Note that it is preferable to use a material that does not transmit moisture and oxygen as much as possible for the sealant 305 . For the second substrate 306, the substrate that can be used for the first substrate 301 can also be used. Therefore, various substrates described in other embodiments can be used as appropriate. As a substrate, in addition to a glass substrate and a quartz substrate, a plastic substrate made of FRP (Fiber-Reinforced Plastics), PVF (Polyvinyl Fluoride), polyester, acrylic resin, or the like can be used. When glass frit is used as the sealant, the first substrate 301 and the second substrate 306 are preferably glass substrates from the viewpoint of adhesiveness.

As described above, an active matrix light-emitting device can be obtained.

Further, when an active matrix light-emitting device is formed on a flexible substrate, the FET and the light-emitting element may be directly formed on the flexible substrate, but the FET and the light-emitting element may be formed on another substrate having a peeling layer. , the FET and the light-emitting element may be separated by a separation layer by applying heat, force, laser irradiation, or the like, and transferred to a flexible substrate. As the separation layer, for example, a laminate of inorganic films such as a tungsten film and a silicon oxide film, an organic resin film such as polyimide, or the like can be used. In addition to substrates on which transistors can be formed, flexible substrates include paper substrates, cellophane substrates, aramid film substrates, polyimide film substrates, cloth substrates (natural fibers (silk, cotton, linen), synthetic fibers ( nylon, polyurethane, polyester) or recycled fiber (including acetate, cupra, rayon, recycled polyester), leather substrate, or rubber substrate. By using these substrates, durability and heat resistance are excellent, and weight reduction and thickness reduction can be achieved.

Note that the structure described in this embodiment can be combined with any of the structures described in other embodiments as appropriate.

(Embodiment 5)
In this embodiment, examples of various electronic devices and automobiles completed by applying the light-emitting element of one embodiment of the present invention and the light-emitting device including the light-emitting element of one embodiment of the present invention will be described. Note that the light-emitting device can be mainly applied to a display portion in the electronic devices described in this embodiment.

The electronic devices illustrated in FIGS. 4A to 4E include a housing 7000, a display portion 7001, a speaker 7003, an LED lamp 7004, operation keys 7005 (including a power switch or an operation switch), connection terminals 7006, Sensor 7007 (force, displacement, position, speed, acceleration, angular velocity, number of rotations, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity , tilt, vibration, smell, or infrared), a microphone 7008, and the like.

FIG. 4A shows a mobile computer, which can have a switch 7009, an infrared port 7010, etc. in addition to those described above.

FIG. 4B shows a portable image reproducing device (for example, a DVD reproducing device) provided with a recording medium, which may include a second display portion 7002, a recording medium reading portion 7011, and the like in addition to the components described above. can.

FIG. 4C shows a digital camera with a television image receiving function, which can have an antenna 7014, a shutter button 7015, an image receiving portion 7016, and the like in addition to the above.

FIG. 4D shows a portable information terminal. The portable information terminal has a function of displaying information on three or more sides of the display portion 7001 . Here, an example in which information 7052, information 7053, and information 7054 are displayed on different surfaces is shown. For example, the user can confirm the information 7053 displayed at a position that can be observed from above the mobile information terminal while the mobile information terminal is stored in the chest pocket of the clothes. The user can confirm the display without taking out the mobile information terminal from the pocket, and can determine, for example, whether or not to receive a call.

FIG. 4E illustrates a portable information terminal (including a smartphone) which can include a housing 7000, a display portion 7001, operation keys 7005, and the like. Note that the portable information terminal may be provided with a speaker 7003, a connection terminal 7006, a sensor 7007, and the like. Also, the portable information terminal can display characters and image information on its multiple surfaces. Here, an example of displaying three icons 7050 is shown. Information 7051 indicated by a dashed rectangle can also be displayed on another surface of the display portion 7001 . Examples of the information 7051 include notification of incoming e-mail, SNS, telephone, etc., title of e-mail, SNS, etc., sender name, date and time, remaining battery level, strength of antenna reception, and the like. Alternatively, an icon 7050 or the like may be displayed at the position where the information 7051 is displayed.

FIG. 4F illustrates a large television device (also referred to as a television or a television receiver), which can include a housing 7000, a display portion 7001, and the like. Also, here, a configuration in which the housing 7000 is supported by a stand 7018 is shown. Further, the operation of the television apparatus can be performed by a separate remote controller 7111 or the like. Note that the display portion 7001 may be provided with a touch sensor, and the display portion 7001 may be operated by touching the display portion 7001 with a finger or the like. The remote controller 7111 may have a display section for displaying information output from the remote controller 7111 . A channel and a volume can be operated with operation keys or a touch panel included in the remote controller 7111 , and an image displayed on the display portion 7001 can be operated.

The electronic devices illustrated in FIGS. 4A to 4F can have various functions. For example, a function to display various information (still images, moving images, text images, etc.) on the display unit, a touch panel function, a calendar, a function to display the date or time, a function to control processing by various software (programs). , wireless communication function, function to connect to various computer networks using wireless communication function, function to transmit or receive various data using wireless communication function, read programs or data recorded on recording media It can have a function of displaying on a display portion, and the like. Furthermore, in an electronic device having a plurality of display units, one display unit mainly displays image information, and another display unit mainly displays character information, or a parallax is considered for a plurality of display units. It is possible to have a function of displaying a three-dimensional image by displaying an image that has been drawn, and the like. In addition, in electronic devices with an image receiving unit, there is a function to shoot still images, a function to shoot moving images, a function to correct the shot images automatically or manually, and a function to save the shot images to a recording medium (external or built in the camera). It can have a function of saving, a function of displaying a captured image on a display portion, and the like. Note that the functions that the electronic devices illustrated in FIGS. 4A to 4F can have are not limited to these, and can have various functions.

FIG. 4G shows a wristwatch-type portable information terminal that can be used as a smart watch, for example. This wristwatch-type portable information terminal includes a housing 7000, a display portion 7001, operation buttons 7022 and 7023, a connection terminal 7024, a band 7025, a microphone 7026, a sensor 7029, a speaker 7030, and the like. The display portion 7001 has a curved display surface and can perform display along the curved display surface. In addition, this portable information terminal is capable of hands-free communication by mutual communication with a headset capable of wireless communication, for example. Note that the connection terminal 7024 enables mutual data transmission and charging with another information terminal. The charging operation can also be performed by wireless power supply.

A display portion 7001 mounted on a housing 7000 that also serves as a bezel portion has a non-rectangular display area. The display unit 7001 can display an icon representing time, other icons, and the like. Further, the display portion 7001 may be a touch panel (input/output device) equipped with a touch sensor (input device).

Note that the smart watch illustrated in FIG. 4G can have various functions. For example, a function to display various information (still images, moving images, text images, etc.) on the display unit, a touch panel function, a calendar, a function to display the date or time, a function to control processing by various software (programs). , wireless communication function, function to connect to various computer networks using wireless communication function, function to transmit or receive various data using wireless communication function, read programs or data recorded on recording media It can have a function of displaying on a display portion, and the like.

In addition, inside the housing 7000, there are speakers, sensors (force, displacement, position, speed, acceleration, angular velocity, number of revolutions, distance, light, liquid, magnetism, temperature, chemical substances, sound, time, hardness, electric field, current , voltage, power, radiation, flow, humidity, gradient, vibration, odor or infrared), microphone, etc.

Note that the light-emitting device of one embodiment of the present invention and the display device including the light-emitting element of one embodiment of the present invention can be used for each display portion of the electronic device described in this embodiment, and the electronic device has a long life. can be realized.

Further, as an electronic device to which a light-emitting device is applied, there is a foldable portable information terminal as shown in FIGS. FIG. 5A shows a portable information terminal 9310 in an unfolded state. FIG. 5B shows the portable information terminal 9310 in the middle of changing from one of the unfolded state and the folded state to the other. Further, FIG. 5C shows a portable information terminal 9310 in a folded state. The portable information terminal 9310 has excellent portability in the folded state, and has excellent display visibility due to a seamless wide display area in the unfolded state.

The display portion 9311 is supported by three housings 9315 connected by hinges 9313 . Note that the display portion 9311 may be a touch panel (input/output device) equipped with a touch sensor (input device). In addition, the display portion 9311 can be reversibly transformed from the unfolded state to the folded state by bending between the two housings 9315 via the hinges 9313 . Note that the light-emitting device of one embodiment of the present invention can be used for the display portion 9311 . Also, an electronic device with a long life can be realized. A display area 9312 in the display portion 9311 is a display area located on the side surface of the portable information terminal 9310 in the folded state. In the display area 9312, information icons, frequently used apps, shortcuts of programs, and the like can be displayed, so that information can be checked and apps can be started smoothly.

6A and 6B show an automobile to which the light emitting device is applied. That is, the light emitting device can be provided integrally with the automobile. Specifically, it can be applied to a part or the whole of a light 5101 (including the rear part of the vehicle body), a tire wheel 5102, and a door 5103 on the outside of an automobile shown in FIG. 6(A). Further, it can be applied to a display portion 5104, a steering wheel 5105, a shift lever 5106, a seat 5107, an inner rear view mirror 5108, etc. inside an automobile shown in FIG. 6B. In addition, you may apply to a part of glass window.

As described above, electronic devices and automobiles to which the light-emitting device or the display device of one embodiment of the present invention is applied can be obtained. In that case, an electronic device with a long life can be realized. Note that applicable electronic devices and automobiles are not limited to those shown in the present embodiment, and can be applied in all fields.

Note that the structure described in this embodiment can be combined with any of the structures described in other embodiments as appropriate.

(Embodiment 6)
In this embodiment, a structure of a lighting device manufactured using a light-emitting device that is one embodiment of the present invention or a light-emitting element that is part of the device will be described with reference to FIGS.

FIGS. 7A and 7B show examples of cross-sectional views of lighting devices. Note that FIG. 7A shows a bottom emission type lighting device in which light is extracted to the substrate side, and FIG. 7B shows a top emission type lighting device in which light is extracted to the sealing substrate side.

A lighting device 4000 illustrated in FIG. 7A has a light-emitting element 4002 over a substrate 4001 . In addition, a substrate 4003 having unevenness is provided outside the substrate 4001 . A light emitting element 4002 has a first electrode 4004 , an EL layer 4005 and a second electrode 4006 .

The first electrode 4004 is electrically connected with the electrode 4007 and the second electrode 4006 is electrically connected with the electrode 4008 . Further, an auxiliary wiring 4009 electrically connected to the first electrode 4004 may be provided. Note that an insulating layer 4010 is formed on the auxiliary wiring 4009 .

Also, the substrate 4001 and the sealing substrate 4011 are bonded with a sealing material 4012 . A desiccant 4013 is preferably provided between the sealing substrate 4011 and the light emitting element 4002 . Note that since the substrate 4003 has unevenness as shown in FIG. 7A, the extraction efficiency of light generated in the light emitting element 4002 can be improved.

A lighting device 4200 in FIG. 7B has a light-emitting element 4202 over a substrate 4201 . A light emitting element 4202 has a first electrode 4204 , an EL layer 4205 and a second electrode 4206 .

First electrode 4204 is electrically connected to electrode 4207 and second electrode 4206 is electrically connected to electrode 4208 . Further, an auxiliary wiring 4209 electrically connected to the second electrode 4206 may be provided. Further, an insulating layer 4210 may be provided under the auxiliary wiring 4209 .

A substrate 4201 and an uneven sealing substrate 4211 are bonded with a sealing material 4212 . A barrier film 4213 and a planarization film 4214 may be provided between the sealing substrate 4211 and the light emitting element 4202 . Note that since the sealing substrate 4211 has unevenness as shown in FIG. 7B, the extraction efficiency of light generated in the light emitting element 4202 can be improved.

Further, as an application example of these lighting devices, there is a ceiling light for indoor lighting. Ceiling lights include a type directly attached to the ceiling, a type embedded in the ceiling, and the like. Note that such a lighting device is configured by combining a light emitting device with a housing or a cover.

In addition, it can be applied to a foot light or the like that can improve the safety of the foot by irradiating the floor with light. Footlights are useful, for example, for use in bedrooms, stairs, corridors, and the like. In that case, the size and shape can be appropriately changed according to the size and structure of the room. In addition, a stationary lighting device configured by combining a light emitting device and a support base is also possible.

Moreover, it is also possible to apply it as a sheet-shaped illuminating device (sheet-shaped illumination). Since the sheet-like lighting is used by attaching it to a wall surface, it does not take up much space and can be used for a wide range of purposes. In addition, it is easy to increase the area. In addition, it can also be used for walls and housings having curved surfaces.

In addition to the above, a lighting device having a function as furniture can be obtained by applying the light-emitting device of one embodiment of the present invention or a light-emitting element that is part of the furniture to a part of furniture provided in a room. can be done.

As described above, various lighting devices to which the light-emitting device is applied can be obtained. Note that these lighting devices are included in one embodiment of the present invention.

Further, the structure described in this embodiment can be combined with any of the structures described in other embodiments as appropriate.

<<Synthesis Example 1>>
In this example, an organometallic complex, bis{2-[6-(4-cyano-2,6-dimethylphenyl)- Synthesis of ⁴ -pyrimidinyl-κN ]phenyl-κC}(2,4-pentanedionato-κO,O′)iridium (III) (abbreviation: [Ir(ppm-dmCP) ₂ (acac)]) is described. do. The structure of [Ir(ppm-dmCP) ₂ (acac)] is shown below.

<Step 1: Synthesis of 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile>
10.06 g of 4-bromo-3,5-dimethylbenzonitrile, 18.35 g of bis(pinacolato)diboron, 21.73 g of potassium acetate, and 240 mL of dimethylsulfoxide were placed in a three-necked flask equipped with a reflux tube, and the inside was replaced with nitrogen. . After degassing by stirring the inside of the flask under reduced pressure, [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (abbreviation: Pd(dppf)Cl ₂ CH ₂ Cl ₂ ) 0.59 g and 0.59 g of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (abbreviation: S-Phos) were added and stirred at 100° C. for 32.5 hours. After a predetermined period of time, extraction with toluene was performed. Thereafter, the product was purified by silica gel column chromatography using hexane:ethyl acetate=10:1 as a developing solvent to obtain the desired product (white solid, yield: 5.89 g, yield: 48%). The synthesis scheme of step 1 is shown in formula (a-1) below.

<Step 2: Synthesis of 4-(4-cyano-2,6-dimethylphenyl)-6-phenylpyrimidine (abbreviation: Hppm-dmCP)>
Then 0.74 g of 4-chloro-6-phenylpyrimidine, 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane, obtained in step 1 above -2-yl)benzonitrile 1.28 g, tripotassium phosphate 3.23 g, toluene 43 mL, and water 4.3 mL were placed in a three-necked flask equipped with a reflux tube, and the inside was replaced with nitrogen.

After deaeration by stirring the inside of the flask under reduced pressure, 0.094 g of tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd ₂ (dba) ₃ ), tris(2,6-dimethoxyphenyl)phosphine ( Abbreviations: 0.19 g of P(2,6MeOPh) ₃ ) was added and stirred at 110° C. for 23 hours. After a predetermined period of time, extraction with toluene was performed. Thereafter, purification was performed by silica gel column chromatography using hexane:ethyl acetate=5:1 as a developing solvent to obtain the desired pyrimidine derivative, Hppm-dmCP (white solid, yield: 0.97 g, yield: 88%). The synthesis scheme of step 2 is shown in formula (a-2) below.

<Step 3: Di-μ-chloro-tetrakis{2-[6-(4-cyano-2,6-dimethylphenyl)-4-pyrimidinyl- ^κN ]phenyl-κC} diiridium (III) (abbreviation: [ Synthesis of Ir(ppm-dmCP) ₂ Cl] ₂ )>
Next, 15 mL of 2-ethoxyethanol, 5 mL of water, 1.60 g of Hppm-dmCP obtained in step 2 above, and 0.81 g of iridium chloride hydrate (IrCl ₃ ·H ₂ O) (manufactured by Furuya Metal Co., Ltd.) were added to a reflux tube. was placed in an eggplant flask fitted with , and the inside of the flask was replaced with argon. Then, it was irradiated with microwaves (2.45 GHz, 100 W) for 3 hours to react. After a predetermined period of time, the resulting residue was suction filtered and washed with methanol to obtain a binuclear complex [Ir(ppm-dmCP) ₂ Cl] ₂ (orange solid, yield 1.45 g, yield 67%). The synthesis scheme of step 3 is shown in formula (a-3) below.

<Step 4: Synthesis of [Ir(ppm-dmCP) ₂ (acac)]>
20 mL of 2-ethoxyethanol, 1.44 g of the binuclear complex obtained in step 3 above, [Ir(ppm-dmCP) ₂ Cl] ₂ , 0.41 g of acetylacetone (abbreviation: Hacac), and 0.93 g of sodium carbonate were passed through the reflux tube. The mixture was placed in an eggplant flask equipped with a vacuum cleaner, and the inside of the flask was replaced with argon. After that, it was irradiated with microwaves (2.45 GHz, 100 W) for 4 hours. The obtained residue was suction-filtered with dichloromethane, and the filtrate was concentrated. The resulting solid was purified by silica gel column chromatography using hexane:ethyl acetate = 2:1 as a developing solvent, and then recrystallized with a mixed solvent of dichloromethane and methanol to give an organometallic complex, [Ir (ppm -dmCP) ₂ (acac)] was obtained as a yellow-orange powder (0.19 g, 7% yield). 0.19 g of the obtained yellow-orange powder was purified by sublimation by the train sublimation method. The conditions for sublimation purification were that the solid was heated at 355° C. while flowing argon gas at a pressure of 2.7 Pa and a flow rate of 11 mL/min. After purification by sublimation, 0.092 g of the target yellow-orange solid was obtained at a yield of 48%. The synthesis scheme of step 4 is shown in formula (a-4) below.

Analysis results by nuclear magnetic resonance spectroscopy ( ¹ H-NMR) of the yellow-orange solid obtained in step 4 above are shown below. Also, a ¹ H-NMR chart is shown in FIG. From this result, it was found that the organometallic complex [Ir(ppm-dmCP) ₂ (acac)] represented by the above structural formula (100) was obtained in this example.

¹ H-NMR. δ(CDCl ₃ ): 1.86 (s, 6H), 2.29 (s, 12H), 5.36 (s, 1H), 6.44 (d, 2H), 6.86 (t, 2H) , 6.91 (t, 2H), 7.52 (s, 4H), 7.66 (d, 2H), 7.68 (s, 2H), 9.25 (s, 2H).

Next, the ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum of a dichloromethane solution of [Ir(ppm-dmCP) ₂ (acac)] were measured.

An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used to measure the absorption spectrum. In addition, an absolute PL quantum yield measurement device (C11347-01, manufactured by Hamamatsu Photonics Co., Ltd.) was used to measure the emission spectrum, and a dichloromethane deoxygenated solution (0.011 mmol/L) was placed in a quartz cell under a nitrogen atmosphere. , was sealed and measurements were made at room temperature.

FIG. 9 shows the measurement results of the obtained absorption spectrum and emission spectrum. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. In addition, the thin solid line in FIG. 9 indicates the absorption spectrum, and the thick solid line indicates the emission spectrum. The absorption spectrum shown in FIG. 9 is obtained by subtracting the absorption spectrum measured by putting only dichloromethane in a quartz cell from the absorption spectrum measured by putting a dichloromethane solution (0.011 mmol/L) in a quartz cell.

From the results in FIG. 9, the organometallic complex [Ir(ppm-dmCP) ₂ (acac)], which is one embodiment of the present invention, exhibited an emission peak at 571 nm, and yellow light emission was observed from the dichloromethane solution.

In this example, bis{2-[6-(4-cyano-2,6-dimethylphenyl)-4-pyrimidinyl-κN ³ ]phenyl described in Example 1 was used as a light-emitting element that is one embodiment of the present invention. -κC}(2,4-pentanedionato-κO,O′)iridium (III) (abbreviation: [Ir(ppm-dmCP) ₂ (acac)]) (structural formula (100)) was used for the light-emitting layer. Bis{2-[6-(2,6-dimethylphenyl)-4-pyrimidinyl- ^κN ]phenyl-κC}(2,4-pentanedionato-κO , O′) iridium (III) (abbreviation: [Ir(ppm-dmp) ₂ (acac)]) (structural formula (200)) for the light-emitting layer. Describe the characteristics. Note that FIG. 10 shows an element structure of a light-emitting element used in this example, and Table 1 shows a specific structure. Chemical formulas of materials used in this example are shown below.

<<Fabrication of light-emitting element>>
In the light-emitting element shown in this example, a hole-injection layer 911, a hole-transport layer 912, a light-emitting layer 913, an electron-transport layer 914, and It has a structure in which electron injection layers 915 are sequentially stacked and a second electrode 903 is stacked on the electron injection layers 915 .

First, a first electrode 901 was formed over a substrate 900 . The electrode area was 4 mm ² (2 mm×2 mm). A glass substrate was used as the substrate 900 . The first electrode 901 was formed by sputtering indium tin oxide containing silicon oxide (ITSO) to a thickness of 70 nm.

Here, as a pretreatment, the surface of the substrate was washed with water, baked at 200° C. for 1 hour, and then subjected to UV ozone treatment for 370 seconds. After that, the substrate was introduced into a vacuum deposition apparatus whose interior was evacuated to about 10 ⁻⁴ Pa, vacuum baked at 170° C. for 30 minutes in a heating chamber in the vacuum deposition apparatus, and then exposed to heat for about 30 minutes. chilled.

Next, a hole-injection layer 911 was formed over the first electrode 901 . The hole injection layer 911 is formed by reducing the pressure in the vacuum deposition apparatus to 10 ⁻⁴ Pa, and then applying 4,4′,4″-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P). -II) and molybdenum oxide were formed by co-evaporating DBT3P-II:molybdenum oxide=2:1 (mass ratio) so that the film thickness would be 55 nm.

Next, a hole-transport layer 912 was formed over the hole-injection layer 911 . The hole transport layer 912 was formed using 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP) by evaporation to a thickness of 20 nm.

Next, a light-emitting layer 913 was formed over the hole-transport layer 912 .

In the light-emitting layer 913 of the light-emitting element 1, 2mDBTBPDBq-II is used as a host material, PCBBiF is used as an assist material, and bis{2-[ 6-(4-cyano-2,6-dimethylphenyl)-4-pyrimidinyl-κN ^] phenyl-κC}(2,4-pentanedionato-κO,O′)iridium (III) (abbreviation: [Ir( ppm-dmCP) ₂ (acac)]) (structural formula: 100) with a weight ratio of 2 mDBTBPDBq-II: PCBBiF: [Ir(ppm-dmCP) ₂ (acac)] = 0.75:0.25:0 It was co-evaporated so as to be 0.075. In addition, the film thickness was set to 40 nm.

The light-emitting layer 913 of the comparative light-emitting element 2 uses 2mDBTBPDBq-II as the host material, PCBBiF as the assist material, and bis{2-[6-(2,6-dimethylphenyl) as the guest material (phosphorescent material). -4-pyrimidinyl- ^κN ]phenyl-κC}(2,4-pentanedionato-κO,O′)iridium (III) (abbreviation: [Ir(ppm-dmp) ₂ (acac)]), weight They were co-deposited in a ratio of 2mDBTBPDBq-II:PCBBiF:[Ir(ppm-dmp) ₂ (acac)]=0.75:0.25:0.075. In addition, the film thickness was set to 40 nm.

Next, an electron-transporting layer 914 was formed over the light-emitting layer 913 . In the electron-transporting layer 914, 2mDBTBPDBq-II has a thickness of 20 nm and 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen) has a thickness of 15 nm. It was formed by sequentially vapor-depositing.

Next, an electron injection layer 915 was formed over the electron transport layer 914 . The electron injection layer 915 was formed by vapor deposition using lithium fluoride (LiF) to a thickness of 1 nm.

Next, a second electrode 903 was formed over the electron injection layer 915 . The second electrode 903 was formed by vapor deposition of aluminum so as to have a thickness of 200 nm. Note that the second electrode 903 functions as a cathode in this embodiment.

Through the above steps, a light-emitting element having the EL layer 902 interposed between a pair of electrodes was formed over the substrate 900 . Note that the hole-injection layer 911, the hole-transport layer 912, the light-emitting layer 913, the electron-transport layer 914, and the electron-injection layer 915 described in the above steps are functional layers forming the EL layer in one embodiment of the present invention. In the vapor deposition process in the manufacturing method described above, a vapor deposition method using a resistance heating method was used in all cases.

Further, the light-emitting device manufactured as described above is sealed with another substrate (not shown). When sealing using another substrate (not shown), another substrate (not shown) coated with a sealant that is cured by ultraviolet light is placed on the substrate 900 in a nitrogen atmosphere glove box. The substrates were fixed, and the substrates were adhered so that the sealing agent adhered around the light emitting element formed on the substrate 900 . At the time of sealing, ultraviolet light of 365 nm was irradiated at 6 J/cm ² to solidify the sealant, and the sealant was stabilized by heat treatment at 80° C. for 1 hour.

<<Operating characteristics of light-emitting element>>
The operating characteristics of each manufactured light-emitting device were measured. The measurement was performed at room temperature (atmosphere maintained at 25°C). 11 to 14 show the results.

Table 2 below shows main initial characteristic values of each light-emitting element near 1000 cd/m ² .

From the above results, Light-Emitting Element 1 exhibits favorable device characteristics, and in particular, a higher external quantum efficiency than Comparative Light-Emitting Element 2 is obtained. This can be attributed to the use of the organometallic complex [Ir(ppm-dmCP) ₂ (acac)], which is one embodiment of the present invention, for the light-emitting layer of the light-emitting element 1 .

That is, in the organometallic complex [Ir(ppm-dmCP) ₂ (acac)] which is one embodiment of the present invention, the pyrimidine ring coordinated to Ir has at least one phenyl group having a cyano group as a substituent. And, since it has a structure in which a phenyl group having a cyano group is bonded to the 6-position of the pyrimidine ring, due to the phenyl group having a cyano group bonded to the 6-position of the pyrimidine ring, the horizontal direction with respect to the vapor deposition substrate surface It is thought that the light extraction efficiency is improved because the orientation of the molecules of is increased.

Further, FIG. 15 shows emission spectra when a current was applied to the light-emitting element 1 and the comparative light-emitting element 2 at a current density of 2.5 mA/cm ² . In FIG. 15, Light-Emitting Element 1 exhibits an emission spectrum with a peak near 574 nm, which is derived from light emitted from the organometallic complex [Ir(ppm-dmCP) ₂ (acac)] contained in the light-emitting layer 913 . Further, Comparative Light-Emitting Element 2 exhibits an emission spectrum having a peak near 559 nm, which is derived from light emitted from the organometallic complex [Ir(ppm-dmp) ₂ (acac)] contained in the light-emitting layer 913 . Note that the maximum emission wavelength of the light-emitting element 1 is shifted in the longer wavelength direction than that of the comparative light-emitting element 2 . This is because, in the light-emitting element 1, in the organometallic complex [Ir(ppm-dmCP) ₂ (acac)] included in the light-emitting layer 913, the phenyl group of the pyrimidine ring of the ligand has a cyano group as a substituent. This is because the LUMO of the ligand is lowered by having it. Therefore, it can be said that the organometallic complex of one embodiment of the present invention is suitable for shifting the maximum emission wavelength to a longer wavelength and adjusting the emission wavelength to a red emission region.

Next, a reliability test was performed on the light-emitting element 1 and the comparative light-emitting element 2. FIG. FIG. 16 shows the results of the reliability test. In FIG. 16, the vertical axis indicates the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis indicates the driving time (h) of the device. Note that in the reliability test, the current density was set to 50 mA/cm ² to drive the light emitting element.

From the results of the reliability test, it was found that Light-Emitting Element 1 exhibited higher reliability than Comparative Light-Emitting Element 2. This can be said to be due to the use of the organometallic complex [Ir(ppm-dmCP) ₂ (acac)] (Structural Formula (100)), which is one embodiment of the present invention, for the light-emitting layer of Light-Emitting Element 1 . Note that [Ir(ppm-dmCP) ₂ (acac)] has a cyano group as a substituent in its molecular structure, so it has the characteristics of being resistant to decomposition and having high heat resistance, although it has a high sublimation temperature. Therefore, high-purity [Ir(ppm-dmCP) ₂ (acac)] can be used without thermal decomposition due to sublimation purification, so it can be said that the reliability of the light-emitting element 1 is improved.

In addition, a quadrupole mass spectrometer (manufactured by ULVAC, residual gas analyzer Qulee BGM-) was used to analyze the desorption gas generated in the vapor deposition chamber during vapor deposition of the light-emitting layers of Light-Emitting Element 1 and Comparative Light-Emitting Element 2. 202) was used to measure the pressure (detected partial pressure: Pa) of a specific gas corresponding to the mass-to-charge ratio in the measured gas inside the chamber. The results are shown in FIG. In FIG. 17, the horizontal axis indicates the mass-to-charge ratio (m/z), and the vertical axis indicates the pressure of the specific gas (detected partial pressure: Pa) corresponding to the mass-to-charge ratio. Also, B. in FIG. G. is the result of measuring the pressure of a specific gas (detected partial pressure: Pa) corresponding to the mass-to-charge ratio in the gas measured inside the chamber immediately before vapor deposition of each light-emitting element. From this result, [Ir(ppm-dmCP) ₂ (acac)] used in the light-emitting layer of Light-Emitting Element 1 is equivalent to [Ir(ppm-dmCP) ₂ (acac) ], less desorbed gas components were detected despite the high sublimation temperature. From this, it can be said that [Ir(ppm-dmCP) ₂ (acac)] is more difficult to thermally decompose than [Ir(ppm-dmp) ₂ (acac)]. In other words, the organometallic complex [Ir(ppm-dmCP) ₂ (acac)] synthesized in this example is difficult to thermally decompose even though the sublimation temperature is increased by including the cyano group in the substituent. It was confirmed to have a structure (that makes it difficult to generate low-molecular-weight decomposition products).

<<Synthesis Example 2>>
In this example, an organometallic complex, bis{4,6-dimethyl-2-[6-(5-cyano-2- methylphenyl)-4-pyrimidinyl- ^κN ]phenyl-κC}(2,2,6,6-tetramethyl-3,5-heptanedionato-κ ² O,O′) iridium (III) (abbreviation: [Ir( A method for synthesizing dmpm-m5CP) ₂ (dpm)]) will be described. The structure of [Ir(dmpm-m5CP) ₂ (dpm)] is shown below.

<Step 1: Synthesis of 4-chloro-6-(3,5-dimethylphenyl)pyrimidine>
8.97 g of 4,6-dichloropyrimidine, 9.01 g of 3,5-dimethylphenylboronic acid, 95 mL of 2M aqueous sodium carbonate solution, and 360 mL of ethylene glycol dimethyl ether (abbreviation: DME) were placed in a three-necked flask equipped with a reflux tube, and the inside was was replaced with nitrogen. After deaeration by stirring the inside of the flask under reduced pressure, 0.67 g of palladium (II) acetate (abbreviation: Pd(OAc) ₂ ) and 1.61 g of triphenylphosphine (abbreviation: PPh ₃ ) were added, and the temperature was 110°C. and stirred for 11 hours. After a predetermined period of time, extraction was performed with ethyl acetate. Thereafter, the product was purified by silica gel column chromatography using dichloromethane as a developing solvent to obtain the desired product (yellowish white solid, yield: 7.60 g, yield: 58%). The synthesis scheme of step 1 is shown in formula (b-1) below.

<Step 2: Synthesis of 4-(5-cyano-2-methylphenyl)-6-(3,5-dimethylphenyl)pyrimidine>
Next, 5.21 g of 4-chloro-6-(3,5-dimethylphenyl)pyrimidine obtained in step 1 above, 5.00 g of 5-cyano-2-methylphenylboronic acid, and 15.32 g of tripotassium phosphate , 240 mL of toluene, and 24 mL of water were placed in a three-necked flask equipped with a reflux tube, and the inside was replaced with nitrogen.

After deaeration by stirring the inside of the flask under reduced pressure, 0.88 g of tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd ₂ (dba) ₃ ), tris(2,6-dimethoxyphenyl)phosphine ( Abbreviation: (2,6-MeOPh) ₃ P) (1.68 g) was added and stirred at 110° C. for 65 hours and a half. After a predetermined period of time, extraction with toluene was performed. After that, it was purified by silica gel column chromatography using dichloromethane:ethyl acetate=20:1 as a developing solvent to obtain the desired pyrimidine derivative, Hdmpm-m5CP (white solid, yield: 4.31 g, yield: 60%). The synthesis scheme of step 2 is shown in formula (b-2) below.

<Step 3: Di-μ-chloro-tetrakis{4,6-dimethyl-2-[6-(5-cyano-2-methylphenyl)-4-pyrimidinyl- ^κN ]phenyl-κC}diiridium (III) Synthesis of (Abbreviation: [Ir(dmpm-m5CP) ₂ Cl] ₂ )>
Next, 30 mL of 2-ethoxyethanol and 10 mL of water, 3.92 g of Hdmpm-m5CP (abbreviation) obtained in step 2 above, and 1.81 g of iridium chloride hydrate (IrCl ₃ ·H ₂ O) (manufactured by Furuya Metal Co., Ltd.) was placed in an eggplant flask equipped with a reflux tube, and the inside of the flask was replaced with argon. Then, it was irradiated with microwaves (2.45 GHz, 100 W) for 3 hours and a half to react. After a predetermined period of time, the resulting residue was suction filtered and washed with methanol to obtain a binuclear complex [Ir(dmpm-m5CP) ₂ Cl] ₂ (orange solid, yield 4.49 g, yield 91%). Also, the synthesis scheme of step 3 is shown in the following formula (b-3).

<Step 4: Bis{4,6-dimethyl-2-[6-(5-cyano-2-methylphenyl)-4-pyrimidinyl- ^κN ]phenyl-κC}(2,2,6,6-tetramethyl Synthesis of -3,5-heptanedionato-κ ² O,O′)iridium (III) (abbreviation: [Ir(dmpm-m5CP) ₂ (dpm)]>
Next, 20 mL of 2-ethoxyethanol, the binuclear complex obtained in step 3 above, 4.48 g of [Ir(dmpm-m5CP) ₂ Cl] ₂ , dipivaloylmethane (abbreviation: Hdpm) 1.51 g, sodium carbonate 2 90 g was placed in an eggplant flask equipped with a reflux tube, and the inside of the flask was replaced with argon.

After that, it was irradiated with microwaves (2.45 GHz, 100 W) for 6 hours. The obtained residue was suction-filtered with dichloromethane, and the filtrate was concentrated. The resulting solid was purified by silica gel column chromatography using dichloromethane as a developing solvent to obtain the organometallic complex [Ir(dmpm-m5CP) ₂ (dpm)] as a red solid (yield: 0.028 g, Yield 0.5%). The synthesis scheme of step 4 is shown in formula (b-4) below.

Analysis results of the red solid obtained in step 4 by nuclear magnetic resonance spectroscopy ( ¹ H-NMR) are shown below. A ¹ H-NMR chart is shown in FIG. From this result, it was found that the organometallic complex [Ir(dmpm-m5CP) ₂ (dpm)] represented by the above structural formula (112) was obtained in this example.

¹ H-NMR. δ(CDCl ₃ ): 0.89 (s, 18H), 1.52 (s, 6H), 2.29 (s, 6H), 2.54 (s, 6H), 5.62 (s, 1H) , 6.66 (s, 2H), 7.48-7.52 (m, 4H), 7.68 (d, 2H), 7.86 (d, 4H), 8.89 (s, 2H).

Next, the ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum of a dichloromethane solution of [Ir(dmpm-m5CP) ₂ (dpm)] were measured.

An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used to measure the absorption spectrum, a dichloromethane solution (0.010 mmol/L) was placed in a quartz cell, and the measurement was performed at room temperature. In addition, an absolute PL quantum yield measurement device (C11347-01, manufactured by Hamamatsu Photonics Co., Ltd.) was used to measure the emission spectrum, and a dichloromethane deoxygenated solution (0.010 mmol/L) was placed in a quartz cell under a nitrogen atmosphere. , was sealed and measurements were made at room temperature.

FIG. 19 shows the measurement results of the obtained absorption spectrum and emission spectrum. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. In addition, the thin solid line in FIG. 19 indicates the absorption spectrum, and the thick solid line indicates the emission spectrum. The absorption spectrum shown in FIG. 19 is obtained by subtracting the absorption spectrum measured by putting only dichloromethane in a quartz cell from the absorption spectrum measured by putting a dichloromethane solution (0.010 mmol/L) in a quartz cell.

From the results in FIG. 19, the organometallic complex [Ir(dmpm-m5CP) ₂ (dpm)], which is one embodiment of the present invention, exhibited an emission peak at 613 nm, and red light emission was observed from the dichloromethane solution.

<<Synthesis Example 3>>
In this example, an organometallic complex, bis{4,6-dimethyl-2-[6-(2-cyano-6- methylphenyl)-4-pyrimidinyl- ^κN ]phenyl-κC}(2,2,6,6-tetramethyl-3,5-heptanedionato-κ ² O,O′) iridium (III) (abbreviation: [Ir( A method for synthesizing dmppm-m2CP) ₂ (dpm)]) will be described. The structure of [Ir(dmpm-m2CP) ₂ (dpm)] is shown below.

<Step 1: Synthesis of 4-(2-cyano-6-methylphenyl)-6-(3,5-dimethylphenyl)pyrimidine>
4-chloro-6-(3,5-dimethylphenyl)pyrimidine 2.18 g, 3-methyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile 2.90 g, triphosphate 6.36 g of potassium, 100 mL of toluene, and 10 mL of water were placed in a three-necked flask equipped with a reflux tube, and the inside was replaced with nitrogen.

After deaeration by stirring the flask under reduced pressure, tris (dibenzylideneacetone) dipalladium (0) (abbreviation: Pd ₂ (dba) ₃ ) 0.28 g, tris (2,6-dimethoxyphenyl) phosphine ( Abbreviation: (2,6-MeOPh) ₃ P) (0.54 g) was added and stirred at 110° C. for 17 hours. After a predetermined period of time, extraction with toluene was performed. After that, it was purified by flash column chromatography using hexane:ethyl acetate=2:1 as a developing solvent to obtain the desired pyrimidine derivative, Hdmpm-m2CP (white solid, yield: 2.08 g, yield: 70%). The synthesis scheme of step 1 is shown in formula (c-1) below.

<Step 2: Di-μ-chloro-tetrakis{4,6-dimethyl-2-[6-(2-cyano-6-methylphenyl)-4-pyrimidinyl- ^κN ]phenyl-κC}diiridium (III) Synthesis of (Abbreviation: [Ir(dmpm-m2CP) ₂ Cl] ₂ )>
Next, 30 mL of 2-ethoxyethanol and 10 mL of water, 2.08 g of Hdmpm-m2CP (abbreviation) obtained in step 1 above, and 1.01 g of iridium chloride hydrate (IrCl ₃ ·H ₂ O) (manufactured by Furuya Metal Co., Ltd.) was placed in an eggplant flask equipped with a reflux tube, and the inside of the flask was replaced with argon. Then, it was irradiated with microwaves (2.45 GHz, 100 W) for 2 hours to react. After a predetermined period of time, the resulting residue was suction filtered and washed with methanol to obtain a binuclear complex [Ir(dmpm-m2CP) ₂ Cl] ₂ (reddish brown solid, yield 1.88 g, yield 69%). Also, the synthesis scheme of step 2 is shown in the following formula (c-2).

<Step 3: Synthesis of [Ir(dmpm-m2CP) ₂ (dpm)]>
Next, 30 mL of 2-ethoxyethanol, the binuclear complex obtained in step 2 above, 1.86 g of [Ir(dmpm-m2CP) ₂ Cl] ₂ , dipivaloylmethane (abbreviation: Hdpm) 0.61 g, sodium carbonate 1 0.18 g was placed in an eggplant flask equipped with a reflux tube, and the inside of the flask was replaced with argon. Then, it was irradiated with microwaves (2.45 GHz, 100 W) for 5 hours. The obtained residue was suction-filtered with dichloromethane, and the filtrate was concentrated. The resulting solid was purified by silica gel column chromatography using dichloromethane as a developing solvent to obtain the organometallic complex [Ir(dmpm-m2CP) ₂ (dpm)] as a red solid (yield: 0.050 g, 2% yield). The synthesis scheme of step 3 is shown in formula (c-3) below.

Analysis results of the red solid obtained in step 3 by nuclear magnetic resonance spectroscopy ( ¹ H-NMR) are shown below. A ¹ H-NMR chart is shown in FIG. From this result, it was found that the organometallic complex [Ir(dmpm-m2CP) ₂ (dpm)] represented by the above structural formula (114) was obtained in this example.

¹ H-NMR. δ(CDCl ₃ ): 0.92 (s, 18H), 1.53 (s, 6H), 2.27 (s, 6H), 2.31 (s, 6H), 5.65 (s, 1H) , 6.65 (s, 2H), 7.48-7.51 (m, 4H), 7.61 (d, 2H), 7.70 (d, 2H), 7.85 (s, 2H), 8.97 (s, 2H).

Next, the ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum of a dichloromethane solution of [Ir(dmpm-m2CP) ₂ (dpm)] were measured.

An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used to measure the absorption spectrum, a dichloromethane solution (0.010 mmol/L) was placed in a quartz cell, and the measurement was performed at room temperature. In addition, an absolute PL quantum yield measurement device (C11347-01, manufactured by Hamamatsu Photonics Co., Ltd.) was used to measure the emission spectrum, and a dichloromethane deoxygenated solution (0.010 mmol/L) was placed in a quartz cell under a nitrogen atmosphere. , was sealed and measurements were made at room temperature.

FIG. 21 shows the measurement results of the obtained absorption spectrum and emission spectrum. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. In FIG. 21, thin solid lines indicate absorption spectra, and thick solid lines indicate emission spectra. The absorption spectrum shown in FIG. 21 is obtained by subtracting the absorption spectrum measured by putting only dichloromethane in a quartz cell from the absorption spectrum measured by putting a dichloromethane solution (0.010 mmol/L) in a quartz cell.

From the results in FIG. 21, the organometallic complex [Ir(dmpm-m2CP) ₂ (dpm)], which is one embodiment of the present invention, exhibited an emission peak at 621 nm, and red light emission was observed from the dichloromethane solution.

<<Synthesis Example 4>>
In this example, an organometallic complex, bis{4,6-dimethyl-2-[6-(2,6-dicyanophenyl), which is one embodiment of the present invention represented by Structural Formula (117) in Embodiment 1 )-4-pyrimidinyl- ^κN ]phenyl-κC}(2,2,6,6-tetramethyl-3,5-heptanedionato-κO,O′)iridium (III) (abbreviation: [Ir(dmpm-dCP) ₂ (dpm)]) will be described. The structure of [Ir(dmpm-dCP) ₂ (dpm)] is shown below.

Further, a method for synthesizing [Ir(dmpm-dCP) ₂ (dpm)] is shown in the synthesis schemes of formulas (d-1) to (d-4) below.

101: first electrode, 102: second electrode, 103: EL layer, 103a, 103b: EL layer, 104: charge generation layer, 111, 111a, 111b: hole injection layer, 112, 112a, 112b: positive Hole transport layer 113, 113a, 113b, 113c: light emitting layer 114, 114a, 114b: electron transport layer 115, 115a, 115b: electron injection layer 200R, 200G, 200B: optical distance 201: first substrate 202: Transistor (FET) 203R, 203G, 203B, 203W: Light emitting element 204: EL layer 205: Second substrate 206R, 206G, 206B: Color filter 206R', 206G', 206B': Color Filter, 207: first electrode, 208: second electrode, 209: black layer (black matrix), 210R, 210G: conductive layer, 301: first substrate, 302: pixel section, 303: drive circuit section ( source line drive circuit), 304a, 304b: drive circuit portion (gate line drive circuit), 305: sealing material, 306: second substrate, 307: lead-out wiring, 308: FPC, 309: FET, 310: FET, 311 : FET 312: FET 313: first electrode 314: insulator 315: EL layer 316: second electrode 317: light emitting element 318: space 900: substrate 901: first electrode , 902: EL layer, 903: Second electrode, 911: Hole injection layer, 912: Hole transport layer, 913: Light emitting layer, 914: Electron transport layer, 915: Electron injection layer, 4000: Lighting device, 4001 : substrate 4002: light emitting element 4003: substrate 4004: first electrode 4005: EL layer 4006: second electrode 4007: electrode 4008: electrode 4009: auxiliary wiring 4010: insulating layer 4011 : Sealing substrate 4012: Sealing material 4013: Desiccant 4015: Diffusion plate 4200: Lighting device 4201: Substrate 4202: Light emitting element 4204: First electrode 4205: EL layer 4206: Second electrode, 4207: electrode, 4208: electrode, 4209: auxiliary wiring, 4210: insulating layer, 4211: sealing substrate, 4212: sealing material, 4213: barrier film, 4214: planarization film, 4215: diffusion plate, 5101: Light 5102: Wheel 5103: Door 5104: Display 5105: Handle 5106: Shift lever 5107: Seat 5108: Inner rear view mirror 7000: Housing 7001: Display 7002: Second display Part 7003: Speaker 7004: LED lamp 7005: Operation key 7006: Connection terminal 7007: Sensor 7008: Microphone 7009: Switch 7010: Infrared port 7011: Recording medium reading part 7012: Support part 7013: earphone 7014: antenna 7015: shutter button 7016: image receiving unit 7018: stand 7020: camera 7021: external connection unit 7022, 7023: operation button 7024: connection terminal 7025: band 7026: Microphone, 7027: Icon representing time, 7028: Other icons, 7029: Sensor, 7030: Speaker, 7052, 7053, 7054: Information, 9310: Personal digital assistant, 9311: Display unit, 9312: Display area, 9313 : hinge, 9315: housing,

Claims (13)

An organometallic complex represented by General Formula (G1).

(In general formula (G1), R ¹ to R ⁴ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, represents either a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms forming ^a ring. Each R ⁹ is independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or a substituted group having 3 to 12 carbon atoms forming a ring. or an unsubstituted heteroaryl group or a cyano group, at least one of which is a cyano group, L is a monoanionic ligand, and n is 1 to 3 represents an integer.) An organometallic complex represented by General Formula (G1).

(In general formula (G1), R ¹ to R ⁴ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, represents either a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms forming ^a ring. Each R ⁹ is independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or a substituted group having 3 to 12 carbon atoms forming a ring. or an unsubstituted heteroaryl group, or a cyano group, any one of R ⁶ to R ⁸ represents a cyano group, and L represents a monoanionic ligand. Also, n represents an integer of 1 to 3.) In claim 1 or claim 2,
The monoanionic ligand includes a monoanionic bidentate chelate ligand having a β-diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, and a monoanionic monoanionic ligand having a phenolic hydroxyl group. bidentate chelating ligands, monoanionic bidentate chelating ligands in which both coordinating atoms are nitrogen, or aromatic heterocyclic bidentate that form metal-carbon bonds with iridium by cyclometallation An organometallic complex that is either one of the ligands. In claim 1 or claim 2,
The monoanionic ligand is an organometallic complex represented by any one of the following general formulas (L1) to (L8).

(Wherein, R ⁷¹ to R ⁷⁷ and R ⁸⁷ to R ¹³¹ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring , a halogen group, a vinyl group, a substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, and A ¹ to A ³ each independently represents an sp ^2- hybridized carbon bonded to nitrogen or hydrogen, or an sp having a substituent represents ^a dihydric carbon, and the substituent represents either an alkyl group having 1 to 6 carbon atoms, a halogen group, a haloalkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group.) An organometallic complex represented by General Formula (G2).

(In the general formula (G2), R ¹ to R ⁴ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, represents either a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms forming a ring, and R ⁵ to R ⁹ is each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, a substituted or unsubstituted aryl group having 3 to 12 carbon atoms forming a ring, represents either an unsubstituted heteroaryl group or a cyano group, at least one of which represents a cyano group, and R ⁷¹ and R ⁷³ each independently form a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a ring; a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms, a halogen group, a vinyl group, a substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms , represents a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring.) An organometallic complex represented by General Formula (G2).

(In the general formula (G2), R ¹ to R ⁴ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, represents either a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms forming ^a ring. Each R ⁹ is independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or a substituted group having 3 to 12 carbon atoms forming a ring. or an unsubstituted heteroaryl group, or a cyano group, any one of R ⁶ to R ⁸ represents a cyano group, and R ⁷¹ and R ⁷³ each independently represent hydrogen, carbon 1 to 6 alkyl groups, substituted or unsubstituted cycloalkyl groups having 5 to 7 carbon atoms forming a ring, halogen groups, vinyl groups, substituted or unsubstituted haloalkyl groups having 1 to 6 carbon atoms, substituted or represents an unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring.) An organometallic complex represented by Structural Formula (100) , Structural Formula (112), Structural Formula (114) or Structural Formula (117) .

A light-emitting device using the organometallic complex according to claim 1 . Having a light-emitting layer between a pair of electrodes,
8. A light-emitting device, wherein the light-emitting layer comprises the organometallic complex according to claim 1. Having a light-emitting layer between a pair of electrodes,
The light emitting layer has a plurality of organic compounds,
8. A light-emitting device, wherein one of the plurality of organic compounds is the organometallic complex according to claim 1. A light-emitting device comprising the light-emitting element according to claim 8 and a transistor or a substrate. a light emitting device according to claim 11;
An electronic device having a microphone, a camera, operation buttons, an external connector, or a speaker. a light emitting device according to claim 11;
A lighting device having a housing, a cover, or a support base.

Images