WO2019097361A1

WO2019097361A1 - Organic compound, light-emitting element, light-emitting device, electronic device, and illumination device

Info

Publication number: WO2019097361A1
Application number: PCT/IB2018/058759
Authority: WO
Inventors: 山口知也; 吉住英子; 木戸裕允; 瀬尾哲史
Original assignee: 株式会社半導体エネルギー研究所
Priority date: 2017-11-17
Filing date: 2018-11-08
Publication date: 2019-05-23
Also published as: KR20200088367A; WO2019097361A8; JPWO2019097361A1; JP7275042B2; CN111727192A

Abstract

The present invention provides a novel organometallic complex. The present invention also provides a novel organometallic complex having superior heat resistance. The present invention additionally provides a novel organometallic complex having excellent color purity. Specifically provided is an organometallic complex represented by general formula (G1) and characterized in that: a pyrimidine ring coordinated to Ir has at least one phenyl group having a cyano group as a substituent; and the phenyl group having the cyano group is bound to position 6 of the pyrimidine ring. (In the formula, R1 to R4 each independently represent hydrogen, a C1–6 alkyl group, a substituted or unsubstituted cycloalkyl group having five to seven ring-forming carbon atoms, a substituted or unsubstituted aryl group having six to 13 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having three to 12 ring-forming carbon atoms. R5 to R9 each independently represent hydrogen, a C1-6 alkyl group, a substituted or unsubstituted aryl group having six to 13 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having three to 12 ring-forming carbon atoms, or a cyano group, with at least one of the radicals representing a cyano group. L represents a monoanionic ligand. n represents an integer from 1 to 3.)

Description

Organic compound, light emitting element, light emitting device, electronic device, and lighting device

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

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

In the 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 in an excited state. It emits light when the excited state returns to the ground state. The types of excited states include singlet excited state (S ^* ) and triplet excited state (T ^* ), and the light emission from the singlet excited state is fluorescence, the light emission from the triplet excited state is phosphorescence and the like. being called. Also, their statistical generation ratio in the light emitting element is considered to be S ^* : T ^* = 1: 3.

Further, among the above-mentioned light emitting substances, a compound capable of converting energy in a singlet excited state into light emission is called a fluorescent compound (fluorescent material) and can convert energy in a triplet excited state into light emission. Compounds are called phosphorescent compounds (phosphorescent materials).

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

That is, in the light emitting element using the phosphorescent material, higher efficiency can be obtained as compared with the light emitting element using the fluorescent material. Therefore, in recent years, various types of phosphorescent materials have been actively developed. In particular, an organometallic complex having iridium or the like as a central metal is attracting attention because of its high phosphorescence quantum yield (for example, Patent Document 1).

JP, 2009-023938, A

Although development of a phosphorescent material exhibiting excellent characteristics as reported in Patent Document 1 described above is in progress, development of a new material exhibiting further excellent characteristics is desired.

Thus, in one aspect of the present invention, novel organometallic complexes are provided. In one embodiment of the present invention, a novel organometallic complex excellent in heat resistance is provided. In one aspect of the present invention, there is provided a novel organometallic complex which is not easily decomposed upon sublimation. In one aspect of the present invention, a novel organometallic complex with high color purity is provided. In one aspect of the present invention, a novel organometallic complex with high molecular orientation is provided. In one embodiment of the present invention, a novel organometallic complex which can be used for a light-emitting element is provided. In one embodiment of the present invention, a novel organometallic complex which can be used for an EL layer of a light-emitting element is provided. Further, the present invention provides a highly efficient and highly reliable novel light-emitting element using the novel organometallic complex which is one embodiment of the present invention. In addition, a novel light emitting device, a novel electronic device, or a novel lighting device is provided. Note that the descriptions of these objects do not disturb the existence of other objects. Further, one aspect of the present invention does not necessarily have to solve all of these problems. In addition, problems other than these are naturally apparent from the description of the specification, drawings, claims, etc., and other problems can be extracted from the descriptions of the specification, drawings, claims, etc. It is.

In 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 a phenyl group having a cyano group is bonded to the 6 position of the pyrimidine ring. It is an organometallic complex represented by the following general formula (G1).

However, in the general formula (G1), 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. And a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming the ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms forming the 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 the ring, or a carbon number forming the ring It represents either a 3-12 substituted or unsubstituted heteroaryl group or a cyano group, and at least one represents a cyano group. L represents a monoanionic ligand. Also, n represents an integer of 1 to 3.

Another embodiment of the present invention is an organometallic complex represented by the following general formula (G1).

However, in the general formula (G1), 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. And a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming the ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms forming the 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 the ring, or a carbon number forming the ring It represents either a 3-12 substituted or unsubstituted heteroaryl group or a cyano group. In addition, any one of R ⁶ to R ⁸ represents a cyano group. L represents a monoanionic ligand. Also, n represents an integer of 1 to 3.

In the configuration represented by the above general formula (G1), n is 2.

Further, in each of the above configurations, the monoanionic ligand is a monoanionic bidentate chelating ligand having a β-diketone structure, a monoanionic bidentate chelating ligand having a carboxyl group, a phenolic A metal-carbon bond is formed with iridium by a monoanionic bidentate chelate ligand having a hydroxyl group, a monoanionic bidentate chelate ligand in which both coordination elements are nitrogen, or cyclometalation Any one of aromatic heterocyclic bidentate ligands.

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

However, in the above general formulas (L1) to (L8), R ⁷¹ to R ⁷⁷ and R ⁸⁷ to R ¹³¹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, or 5 to 6 carbon atoms forming a ring. 7 substituted or unsubstituted cycloalkyl groups, halogen groups, vinyl groups, substituted or unsubstituted haloalkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 6 carbon atoms, substituted or unsubstituted groups It represents an alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms which forms a ring. Further, A ¹ ~ A ³ represents a sp ² hybridized carbon, each having a sp ² hybridized carbon bonded to the nitrogen or independently hydrogen or a substituent, the substituent is 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 the configuration represented by the above general formula (G1), n is 3.

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

However, in the general formula (G2), 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. And a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming the ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms forming the 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 the ring, or a carbon number forming the ring It represents either a 3-12 substituted or unsubstituted heteroaryl group or a cyano group, and at least one represents a cyano group. R ⁷¹ and R ⁷³ 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 halogen group, a vinyl group, or a substituted group 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 Represents a substituted or unsubstituted aryl group of -13.

However, in the general formula (G2), 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. And a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming the ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms forming the 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 the ring, or a carbon number forming the ring It represents either a 3-12 substituted or unsubstituted heteroaryl group or a cyano group. In addition, any one of R ⁶ to R ⁸ represents a cyano group. R ⁷¹ and R ⁷³ 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 halogen group, a vinyl group, or a substituted group 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 Represents a substituted or unsubstituted aryl group of -13.

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 in the para or meta position is a pyrimidine It is an organometallic complex bonded 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 A light emitting element using an organometallic complex. Note that a light-emitting element having 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 organometallic complex which is one embodiment of the present invention described above. Note that an EL layer formed between a pair of electrodes and a light emitting element formed using the organometallic complex which is an embodiment of the present invention in the light emitting layer included in the EL layer are also included in an embodiment of the present invention. . In addition, a light-emitting device including a transistor, a substrate, and the like in addition to the light-emitting element is also included in the scope of the invention. Furthermore, in addition to these light emitting devices, electronic devices and lighting devices having a microphone, a camera, an operation button, an external connection portion, a housing, a cover, a support, a speaker, and the like are also included in the scope of the invention.

The organometallic complex which is one embodiment of the present invention can be used in the light emitting layer of a light emitting element in combination with another organic compound. That is, since light emission from the triplet excited state can be obtained from the light emitting layer, the efficiency of the light emitting element can be increased, which is very effective. Therefore, a light-emitting element in which the organometallic complex which is one embodiment of the present invention is combined with another organic compound and used for the light-emitting layer is included in one embodiment of the present invention. Furthermore, in addition to the above, a third substance may be added to the light emitting layer.

Further, one embodiment of the present invention includes a light-emitting device having a light-emitting element, and further includes a lighting device having a light-emitting device in its category. Accordingly, a light emitting device herein refers to an image display device, or a light source (including a lighting device). In addition, a module in which a connector such as a flexible printed circuit (FPC) or a TCP (Tape Carrier Package) is attached to a light emitting device, a module in which a printed wiring board is provided ahead of TCP, or a chip on glass (COG) for a light emitting device It is assumed that all light emitting devices include modules in which ICs (integrated circuits) are directly mounted by a method.

One aspect of the present invention can provide a novel organometallic complex. In addition, a novel organometallic complex excellent in heat resistance can be provided. In addition, it is possible to provide a novel organometallic complex which is difficult to be decomposed at the time of sublimation. In addition, one embodiment of the present invention can provide a novel organometallic complex with high color purity. In one embodiment of the present invention, a novel organometallic complex with high molecular orientation can be provided. In one embodiment of the present invention, a novel organometallic complex which can be used for a light-emitting element can be provided. In one embodiment of the present invention, a novel organometallic complex which can be used for an EL layer of a light-emitting element can be provided. In addition, 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. In addition, 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 disturb the existence of other effects. Note that one embodiment of the present invention does not necessarily have all of these effects. Note that effects other than these are naturally apparent from the description of the specification, drawings, claims and the like, and other effects can be extracted from the descriptions of the specification, drawings, claims and the like. It is.

5A to 5C illustrate structures of light-emitting elements. FIG. 7 illustrates a light-emitting device. FIG. 7 illustrates a light-emitting device. 5A to 5C illustrate electronic devices. 5A to 5C illustrate electronic devices. FIG. The figure explaining a lighting installation. ¹ H-NMR chart of an organometallic complex represented by a structural formula (100). UV-visible absorption spectrum and emission spectrum of an organometallic complex represented by a structural formula (100) in a solution. 5A to 5C illustrate light-emitting elements. FIG. 16 shows current density-luminance characteristics of the light-emitting element 1 and the comparative light-emitting element 2. FIG. 16 shows voltage-luminance characteristics of the light-emitting element 1 and the comparative light-emitting element 2. FIG. 16 shows luminance-current efficiency characteristics of the light-emitting element 1 and the comparative light-emitting element 2. FIG. 18 shows voltage-current characteristics of the light-emitting element 1 and the comparative light-emitting element 2. FIG. 16 shows emission spectra of the light-emitting element 1 and the comparative light-emitting element 2. FIG. 18 shows the reliability of the light-emitting element 1 and the comparative light-emitting element 2; The figure which shows the measurement result by a quadrupole mass spectrometer. ¹ H-NMR chart of an organometallic complex represented by a structural formula (112). 11 shows an ultraviolet-visible absorption spectrum and an emission spectrum of a solution of an organometallic complex represented by a structural formula (112). ¹ H-NMR chart of an organometallic complex represented by a structural formula (114). 16 shows an ultraviolet-visible absorption spectrum and an emission spectrum of a solution of an organometallic complex represented by a 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 description of the embodiments below.

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

Further, in the present specification and the like, when describing the configuration of the invention using the drawings, reference numerals denoting the same parts are used in common among different drawings.

Embodiment 1
In this embodiment, an organometallic complex which is one embodiment of the present invention is 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 It has a structure represented by the following general formula (G1) characterized by bonding to

In 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 the ring, or a ring Or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms that forms R.sup.13 or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms that forms 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 the ring, or a carbon number forming the ring It represents either a 3-12 substituted or unsubstituted heteroaryl group or a cyano group, and at least one represents a cyano group. L represents a monoanionic ligand. Also, n represents an integer of 1 to 3.

The organometallic complex which is another aspect of the present invention has a structure represented by the above general formula (G1), and in the above general formula (G1), R ¹ to R ⁴ are each independently hydrogen, It represents either 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 heteroaryl group having 3 to 12 carbon atoms. Further, 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, or a substituted or unsubstituted heterocycloalkyl having 3 to 12 carbon atoms. It represents either an aryl group or a cyano group. In addition, any one of R ⁶ to R ⁸ represents a cyano group. L represents a monoanionic ligand. Also, n represents an integer of 1 to 3.

In the organometallic complex which is another aspect of the present invention, n in the general formula (G1) is 2.

The organometallic complex which is another aspect of the present invention is characterized in that the monoanionic ligand in the general formula (G1) is a monoanionic bidentate chelating ligand having a β-diketone structure, a carboxyl group A monoanionic bidentate chelate ligand having a monobasic, a monoanionic bidentate chelate ligand having a phenolic hydroxyl group, and a monoanionic bidentate chelate ligand in which both coordination elements are nitrogen Or an aromatic heterocyclic bidentate ligand which forms a metal-carbon bond with iridium by cyclometalation.

Another aspect of the present invention is an organometallic complex in which the monoanionic ligand in the general formula (G1) is any one of the following general formulas (L1) to (L8).

In formulas (L1) to (L8), R ⁷¹ to R ⁷⁷ and R ⁸⁷ to R ¹³¹ each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituent having 5 to 7 carbon atoms forming a ring. Or an unsubstituted cycloalkyl group, 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 carbon atom having 1 And an alkylthio group of -6, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. Further, A ¹ ~ A ³ each represent a sp ² hybridized carbon bonded to the nitrogen or independently hydrogen or sp ² hybridized carbon having a substituent, said substituent is an alkyl group having 1 to 6 carbon atoms, a halogen group Or a haloalkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group.

In the organometallic complex which is another aspect of the present invention, n in the general formula (G1) is 3.

Further, an organometallic complex which is another embodiment of the present invention has a structure represented by the following general formula (G2).

In 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 which forms a ring, or a ring Or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms that forms R.sup.13 or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms that forms 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 the ring, or a carbon number forming the ring It represents either a 3-12 substituted or unsubstituted heteroaryl group or a cyano group, and at least one represents a cyano group. R ⁷¹ and R ⁷³ 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 halogen group, a vinyl group, or a substituted group 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 Represents a substituted or unsubstituted aryl group of -13.

The organometallic complex which is another aspect of the present invention has a structure represented by the above general formula (G2), and in the above 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, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring, or a ring Or represents a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. 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 the ring, or a carbon number forming the ring It represents either a 3-12 substituted or unsubstituted heteroaryl group or a cyano group. In addition, any one of R ⁶ to R ⁸ represents a cyano group. R ⁷¹ and R ⁷³ 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 halogen group, a vinyl group, or a substituted group 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 Represents a substituted or unsubstituted aryl group of -13.

In the organometallic complexes represented by the above general formula (G1) and the above general formula (G2), the substitution is preferably methyl group, ethyl group, n-propyl group, isopropyl group, sec-butyl group, alkyl group having 1 to 6 carbon atoms such as tert-butyl group, n-pentyl group, n-hexyl group, phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 1-naphthyl group, It represents substitution by a substituent such as an aryl group having 6 to 12 carbon atoms such as a 2-naphthyl group, a 2-biphenyl group, a 3-biphenyl group, and a 4-biphenyl group. In addition, 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 a substituent, the phenyl groups are bonded to each other to form a spiro-9,9'-bifluoren-2-yl group It is good. More specifically, for example, phenyl group, tolyl group, xylyl group, biphenyl group, indenyl group, naphthyl group, fluorenyl group and the like can be mentioned.

In the organometallic complexes represented by the above general formula (G1) and the above general formula (G2), examples of the alkyl group having 1 to 6 carbon atoms in R ¹ to R ⁹ in the formula include a methyl group. , Ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, hexyl, isohexyl 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. .

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

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

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

Next, specific structural formulas of the organometallic complex which is one embodiment of the present invention described above are shown below.

Note that the organometallic complex represented by the structural formulas (100) to (134) is an example of the organometallic complex represented by the general formula (G1), and the organometallic complex according to one aspect of the present invention is Not limited to this.

Next, an example of a synthesis method of an organometallic complex which is one embodiment of the present invention will be described. In addition, although the organometallic complex which is one aspect | mode of this invention is represented by the following general formula (G1), in the case here, in the formula, the organic metal in the case of n = 2 (the following general formula (G1-1)) A method of synthesizing a complex and an organometallic complex in the case of n = 3 (general formula (G1-2) shown below) will be described.

<< Synthesis Method of Pyrimidine Derivative Represented by General Formula (G0) >>
First, the synthesis method of the pyrimidine derivative (general formula (G0)) contained in the said general formula (G1) is demonstrated.

The pyrimidine derivative represented by the following general formula (G0) (ligand contained in the general formula (G1)) can be conveniently synthesized, for example, by the synthesis method shown below. Here, three types of synthesis methods are shown: a first synthesis method, a second synthesis method, and a third synthesis method.

In the above general formula (G0), 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 which forms a ring, The ring represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms forming the 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 the ring, or a carbon number forming the ring It represents either a 3-12 substituted or unsubstituted heteroaryl group or a cyano group, and at least one represents a cyano group.

<First synthesis method>
As shown in the following synthesis scheme (A-1), the pyrimidine derivative represented by the above general formula (G0) is lithiated with an alkyllithium or the like to give a halogenated benzene derivative (A1) with a pyrimidine halide (A2) It can be obtained by reaction.

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

<Second composition method>
As shown in the following synthesis scheme (A-1 ′), the pyrimidine derivative represented by the above general formula (G0) couples a boronic acid (A1 ′) of a benzene derivative with a halide (A2 ′) of pyrimidine It can be obtained by

In the above synthesis scheme (A-1 ′), X ³ represents a halogen, and B ¹ represents a boronic acid or a boronic ester, a cyclic triol borate salt or the like. In addition to the lithium salt, the cyclic triol borate salt may use 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 the ring, or 6 carbon atoms forming the ring It represents either a substituted or unsubstituted aryl group of ̃13 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 the ring, or a carbon number forming the ring It represents either a 3-12 substituted or unsubstituted heteroaryl group or a cyano group, and at least one represents a cyano group.

<Third synthesis method>
The pyrimidine derivative represented by the above general formula (G0) has a benzene derivative-substituted diketone (A1 ′ ′) and formamide (A2 ′ ′) as a microwave as shown in the following synthesis scheme (A-1 ′ ′) It can be obtained by reacting using

In the above synthesis scheme (A-1 ′ ′), R ¹ to R ⁴ each independently represent a hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted one having 5 to 7 carbon atoms forming a ring. The cycloalkyl group is 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 the ring, or a carbon number forming the ring It represents either a 3-12 substituted or unsubstituted heteroaryl group or a cyano group, and at least one represents a cyano group.

In addition, various types of the compounds (A1), (A2), (A1 ′), (A2 ′), (A1 ′ ′) and (A2 ′ ′) used in the above synthesis method are commercially available. Since pyrimidine derivatives can be synthesized, pyrimidine derivatives represented by General Formula (G0) can be easily synthesized in many types. Therefore, the organometallic complex which is one aspect of the present invention is characterized in being rich in variations of the ligand.

<< Synthesis Method of Organometallic Complex Represented by General Formula (G1-1) >>
The synthesis method of the organometallic complex represented by the above general formula (G1-1) will be described.

As shown in the following synthesis scheme (A-2), the organometallic complex represented by the above general formula (G1-1) is a metal compound of

Group

9 or 10 containing a halogen (rhodium chloride hydrate, Palladium chloride, iridium chloride, iridium bromide, iridium iodide, potassium tetrachloroplatinate, etc., and a pyrimidine derivative represented by the general formula (G0), as a solventless or alcohol solvent (glycerol, ethylene glycol, 2 -An organic metal having a structure crosslinked with a halogen by heating in an inert gas atmosphere using methoxyethanol, 2-ethoxyethanol etc.) alone or a mixed solvent of one or more alcohol solvents and water A dinuclear complex (B) which is a kind of complex and is a novel substance can be obtained. There is no limitation in particular as a heating means, An oil bath, a sand bath, or an aluminum block may be used. Moreover, it is also possible to use a microwave as a 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 substituent 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 the ring, or a carbon number forming the ring It represents either a 3-12 substituted or unsubstituted heteroaryl group or a cyano group, and at least one represents a cyano group.

Next, as shown in the following synthesis scheme (A-3), the binuclear complex (B) obtained in the above synthesis scheme (A-2) and the raw material HL of the monoanionic ligand are inactive By reacting in a gas atmosphere, the proton of HL is eliminated and L is coordinated to the central metal M, whereby an organometallic complex represented by General Formula (G1-1) can be obtained. There is no limitation in particular as a heating means, An oil bath, a sand bath, or an aluminum block may be used. Moreover, it is also possible to use a microwave as a 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 the ring, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming the ring, or 3 to 12 carbon atoms forming the ring Or a substituted or unsubstituted heteroaryl group of 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 the ring, or a carbon number forming the ring It represents either a 3-12 substituted or unsubstituted heteroaryl group or a cyano group, and at least one represents a cyano group.

<< Synthesis Method of Organometallic Complex Represented by General Formula (G1-2) >>
The synthesis method of the organometallic complex represented by the above general formula (G1-2) will be described.

As shown in the following synthesis scheme (A-4), the organometallic complex represented by the above general formula (G1-2) is an iridium compound containing halogen (iridium chloride hydrate, iridium bromide, iridium iodide, Iridium acetate, ammonium hexachloroiridate, etc., or organic iridium complex compounds (acetylacetonato complex, diethyl sulfide complex, di-μ-chloro bridged dinuclear complex, di-μ-hydroxo bridged dinuclear complex, etc.), Obtained by mixing with a pyrimidine derivative represented by (G0), dissolving it in a solventless or alcohol solvent (glycerol, ethylene glycol, 2-methoxyethanol, 2-ethoxyethanol etc.) and heating it. Be

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 having 5 to 7 carbon atoms forming a ring And a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming the ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms forming the 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 the ring, or a carbon number forming the ring It represents either a 3-12 substituted or unsubstituted heteroaryl group or a cyano group, and at least one represents a cyano group.

In the above, as an organometallic complex which is one embodiment of the present invention, a method of synthesizing an organometallic complex represented by General Formula (G1), General Formula (G1-1), and General Formula (G1-2) has been described. However, the present invention is not limited thereto, and may be synthesized by other synthesis methods.

In addition, by using 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. In addition, 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 has been described in this embodiment. Another embodiment of the present invention will be described in another embodiment. However, one embodiment of the present invention is not limited to these. That is, since various aspects of the invention are described in this embodiment and the other embodiments, one aspect of the present invention is not limited to a particular aspect. For example, although an example in the case of applying to a light-emitting element is shown as one embodiment of the present invention, one embodiment of the present invention is not limited thereto. Further, depending on the situation, one embodiment of the present invention may be applied to devices other than light-emitting elements. In addition, depending on the situation, one embodiment of the present invention may not be applied to a light-emitting element.

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

Second Embodiment
In this embodiment, a light-emitting element which is one embodiment of the present invention will be described. Note that the organometallic complex which 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 illustrates a light-emitting element in which an EL layer is sandwiched between a pair of electrodes. Specifically, the EL layer 103 including a light emitting layer is sandwiched between the first electrode 101 and the 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 the charge generation layer 104 is interposed between the EL layers. 6 shows a light emitting element with a stacked structure (tandem structure). Such a light emitting element having a tandem structure can realize a light emitting device which can be driven at low voltage and consumes low power.

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

The charge generation layer 104 preferably has transparency to visible light (specifically, the visible light transmittance of the charge generation layer 104 is 40% or more) from the viewpoint of light extraction efficiency. In addition, the charge generation layer 104 functions even when the conductivity is lower than that of the first electrode 101 and the second electrode 102.

FIG. 1C shows a stack structure of the EL layer 103. In FIG. 1C, in the case where the first electrode 101 functions as an anode, the EL layer 103 includes a hole injection layer 111, a hole transport layer 112, and the like over the first electrode 101. The light emitting layer 113, the electron transport layer 114, and the electron injection layer 115 are sequentially stacked. Also in the case where a plurality of EL layers are provided as in a tandem structure illustrated in FIG. 1B, each EL layer is sequentially stacked from the anode side as described above. When the first electrode 101 is a cathode and the second electrode 102 is an anode, the stacking order is reversed.

The light-emitting layers 113 included in the EL layers (103, 103a, and 103b) each have a light-emitting substance or a plurality of substances in combination as appropriate, and can be configured to obtain fluorescence or phosphorescence which exhibits a desired emission color. be able to. Alternatively, the light emitting layer 113 may have a stacked structure in which light emitting colors are different. In this case, different materials may be used for the light-emitting substance and the other substances used for the stacked light-emitting layers. Alternatively, different emission colors may be obtained from the plurality of EL layers (103a and 103b) illustrated in FIG. 1B. Also in this case, different materials may be used for the light-emitting substances and other substances used for each light-emitting layer.

In the light-emitting element which is one embodiment of the present invention, the obtained light emission may be strengthened by resonating the light emission obtained in the EL layers (103, 103a, 103b) between both electrodes. For example, in FIG. 1C, a minute optical resonator (microcavity) structure is formed by using the first electrode 101 as a reflective electrode and the second electrode 102 as a semi-transmissive and semi-reflective electrode, and an EL layer is formed. The light emission obtained from 103 can be intensified.

In the case where 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 transmissive conductive material (transparent conductive film), a film of a transparent conductive film Optical control can be performed by controlling the thickness. Specifically, the inter-electrode distance between the first electrode 101 and the second electrode 102 is near 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 as follows.

In addition, in order to amplify a desired light (wavelength: λ) obtained from the light emitting layer 113, an optical distance from the first electrode 101 to a region (light emitting region) from which the desired light of the light emitting layer 113 can be obtained The optical distance from the electrode 102 of 2 to the region (light emitting region) from which desired light of the light emitting layer 113 can be obtained is adjusted to be (2 m ′ + 1) λ / 4 (where m ′ is a natural number) It is preferable to do. Note that the light emitting region referred to here indicates 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 high color purity can be obtained.

However, in the above case, the optical distance between the first electrode 101 and the second electrode 102 may be strictly referred to as the total thickness from the reflective region in the first electrode 101 to the reflective region in the second electrode 102. it can. However, since it is difficult to precisely determine the reflection area of the first electrode 101 and the second electrode 102, it is assumed that an arbitrary position of the first electrode 101 and the second electrode 102 is a reflection area. The above-mentioned effects can be sufficiently obtained. In addition, the optical distance between the first electrode 101 and the light emitting layer from which desired light is obtained is strictly the optical distance between the reflective region of 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 a 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 is obtained, any position of the first electrode 101 is a reflective region, Assuming that any position of the light emitting layer from which light is obtained is a light emitting region, the above effect can be sufficiently obtained.

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

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

In the light-emitting element which is one embodiment of the present invention described above, in the case where one of the first electrode 101 and the second electrode 102 is a reflective electrode (reflective electrode), visible light of the reflective electrode The light reflectance is 40% to 100%, preferably 70% to 100%. In addition, it is preferable that this electrode have 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 which is one embodiment of the present invention will be described. Note that, in FIG. 1 (A) to FIG. 1 (E), when the reference numerals are common, the description is also common.

<First electrode and second electrode>
As materials for forming the first electrode 101 and the second electrode 102, materials described below can be used in appropriate combination as long as the functions of the both electrodes in the above-described element structure can be satisfied. For example, metals, alloys, electrically conductive compounds, and mixtures thereof 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 can be mentioned. 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) And metals such as neodymium (Nd), and alloys containing these in combination as appropriate. In addition, elements (for example, lithium (Li), cesium (Cs), calcium (Ca), strontium (Sr)), europium (Eu), ytterbium, which belong to Group 1 or Group 2 of the periodic table of the elements not illustrated above. It is possible to use rare earth metals such as (Yb) and alloys containing these in combination as appropriate, graphene and the like.

When the light emitting element shown in FIG. 1 includes the EL layer 103 having a stacked structure as shown in FIG. 1C and the first electrode 101 is an anode, the positive electrode of the EL layer 103 is formed on the first electrode 101. The hole injection layer 111 and the hole transport layer 112 are sequentially laminated by vacuum evaporation. In addition, as illustrated in FIG. 1D, in the case where the 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 is formed. The hole injection layer 111a of the EL layer 103a and the hole transport layer 112a of the EL layer 103a are sequentially laminated by vacuum evaporation, and after the EL layer 103a and the charge generation layer 104 are sequentially laminated, charge generation is performed. The hole injection layer 111 b and the hole transport layer 112 b of the EL layer 103 b are similarly sequentially stacked on the layer 104.

Hole Injection Layer and Hole Transport Layer
The hole injection layer (111, 111a, 111b) is a layer for injecting holes from the first electrode 101 which is an anode or the charge generation layer (104) to the EL layer (103, 103a, 103b). And a layer containing a material having a high hole injection property.

Materials having high hole injection properties include transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide. In addition to these, phthalocyanine-based 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), which is a low molecular weight compound. -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, 1 3,5-Tris [N- (4-diphenylaminophenyl) -N-phenylamino] benzene (abbreviation: DPA3B), 3- [N- (9-phenylcarbazol-3-yl) -N-phenylamine [3]-9-phenylcarbazole (abbr .: PCzPCA1), 3, 6-bis [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole (abbr .: PCzPCA2), 3- Aromatic amine compounds such as [N- (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), which is a high molecular compound (oligomer, dendrimer, polymer, etc.) -{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) or the like can be used. Alternatively, an acid such as poly (3,4-ethylenedioxythiophene) / poly (styrene sulfonic acid) (abbr .: PEDOT / PSS), polyaniline / poly (styrene sulfonic acid) (abbr .: PAni / PSS), etc. Molecular compounds and the like can also be used.

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

The hole transport layer (112, 112a, 112b) emits holes injected from the first electrode 101 and the charge generation layer 104 by the hole injection layer (111, 111a, 111b) into the light emitting layer (113, 113a, 113b) transport layer. The hole transport layer (112, 112a, 112b) is a layer containing a hole transport material. As the hole transporting material used for the hole transporting layer (112, 112a, 112b), in particular, one having a HOMO level equal to or close to the HOMO level of the hole injecting layer (111, 111a, 111b) is used Is preferred.

As the acceptor property material used for the hole injecting layer (111, 111a, 111b), an oxide of a metal belonging to Groups 4 to 8 in the periodic table of elements can be used. Specifically, molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide, and rhenium oxide can be mentioned. Among them, molybdenum oxide is particularly preferable because it is stable in the air, 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) etc. can be used. In particular, a compound in which an electron withdrawing group is bonded to a condensed aromatic ring having a plurality of hetero atoms, such as HAT-CN, is thermally stable and preferable. Also, [3] radialene derivatives having an electron withdrawing group (in particular, a halogen group such as a fluoro group or a cyano group) are preferable because they have very high electron accepting properties, and specifically, α, α ′, α ′ ′- 1,2,3-cyclopropanetriylidenetris [4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α, α ′, α ′ ′-1,2,3-cyclopropanetriylidenetris [2,6-Dichloro-3,5-difluoro-4- (trifluoromethyl) benzeneacetonitrile], α, α ′, α ′ ′-1,2,3-cyclopropanetriylidenetris [2,3,4 , 5, 6-pentafluorobenzene acetonitrile] and the like.

As a hole transporting material used for the hole injection layer (111, 111a, 111b) and the hole transporting layer (112, 112a, 112b), a substance having a hole mobility of 10 ^-6 cm ² / Vs or more is used. preferable. Note that materials having hole transportability higher than electrons can be used other than these.

The hole transporting material is preferably a material having a high hole transporting property, such as a π electron excess 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.

Specific examples of the hole transporting material 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'-pheny -N '-(9,9-dimethyl-9H-fluoren-2-yl) amino] -9H-fluoren-7-yl} phenylamine (abbreviation: DFLADFL), N- (9,9-dimethyl-2-diphenyl) Amino-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 ( Abbreviations: 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-fluoren-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-carbazol-3-yl) triphenylamine (abbreviation: PCBNBB), 4-phenyldiphenyl- (9-phenyl-9H-carbazol-3-yl) amine Abbreviations: PC1 BP), N, N'-bis (9-phenylcarbazol-3-yl) -N, N'-diphenylbenzene-1,3-diamine (abbreviation: PCA2B), N, N ', N' '- Triphenyl-N, N ', N' '-tris (9-phenylcarbazol-3-yl) benzene-1,3,5-triamine (abbreviation: PCA3B), 9,9-dimethyl-N-phenyl-N- [4- (9-phenyl-9H-carbazol-3-yl) phenyl] fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N- [4- (9-phenyl-9H-carbazol-3-yl) ) Phenyl] 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-diphenylaminophenyl) -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 An aromatic amine compound such as -9,9-dimethylfluorene-2,7-diamine (abbreviation: YGA2F) can be used. In addition, 3- [4- (1-naphthyl) -phenyl] -9-phenyl-9H-carbazole (abbreviation: PCPN), 4,4 ′, 4 ′ ′-tris (carbazol-9-yl) triphenylamine Abbreviations: 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 - Nylamino] biphenyl (abbr .: DPAB), N, N'-bis {4- [bis (3-methylphenyl) amino] phenyl} -N, N'-diphenyl- (1,1'-biphenyl) -4,4 Compounds having an aromatic amine skeleton such as' -diamine (abbreviation: DNTPD), 1,3,5-tris [N- (4-diphenylaminophenyl) -N-phenylamino] benzene (abbreviation: DPA3B), 3-bis (N-carbazolyl) benzene (abbreviation: mCP), 4,4′-di (N-carbazolyl) biphenyl (abbreviation: CBP), 3,6-bis (3,5-diphenylphenyl) -9-phenyl Carbazole (abbreviation: CzTP), 3,3'-bis (9-phenyl-9H-carbazole) (abbreviation: PCCP), 3- [N- (4-diphenylaminophenyl) -N- 3, 4-bis [N- (4-diphenylaminophenyl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzDPA2), 3, 6-bisphenylamino] -9-phenylcarbazole (abbreviation: PCzDPA1) [N- (4-Diphenylaminophenyl) -N- (1-naphthyl) amino] -9-phenylcarbazole (abbreviation: PCzTPN2), 3- [N- (9-phenylcarbazol-3-yl) -N-phenyl Amino] -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-phenyl Carbazole (abbreviation: PCzPCN1), 1,3,5-tris [4- (N-carbazolyl) phenyl] benzene (abbreviation: TCPB), 9- [4- (10-phenyl-9-anthracenyl) phenyl] -9H- A compound having a carbazole skeleton such as carbazole (abbreviation: CzPA), 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] Compounds having a thiophene skeleton such as phenyl) -6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), 4, 4 ′, 4 ′ -(Benzene-1,3,5-triyl) tri (dibenzofuran) (abbreviation: DBF3P-II), 4- {3- [3- (9-phenyl-9H-fluoren-9-yl) phenyl] phenyl} dibenzofuran The compound which has furan skeletons, such as (abbreviation: mmDBFFLBi-II), is mentioned.

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 one or more known various materials may be combined to form a hole transporting layer (111, 111a, 111b) and a hole transporting layer as a hole transporting material. (112, 112a, 112b) can be used. The hole transport layers (112, 112a, 112b) may be formed of a plurality of layers, respectively. That is, for example, the first hole transport layer and the second hole transport layer may be stacked.

In the light emitting element shown in FIG. 1D, the light emitting layer 113a is formed on the hole transport layer 112a of the EL layer 103a by vacuum evaporation. 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 evaporation.

<Light emitting layer>
The light emitting layer (113, 113a, 113b, 113c) is a layer containing a light emitting substance. Note that as the light-emitting substance, a substance exhibiting a light-emitting color such as blue, purple, blue-purple, green, yellowish-green, yellow, orange, red and the like is appropriately used. In addition, by using different light-emitting substances for the plurality of light-emitting layers (113a, 113b, and 113c), different light-emitting colors can be obtained (for example, white light emission obtained by combining light-emitting colors in complementary relationship). . Furthermore, a stacked structure in which one light emitting layer has different light emitting substances may be employed.

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

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

Examples of light-emitting substances that convert singlet excitation energy into light emission include substances that emit fluorescence (fluorescent materials). For example, pyrene derivatives, anthracene derivatives, triphenylene derivatives, fluorene derivatives, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, dibenzo Examples include quinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives, phenanthrene derivatives, naphthalene derivatives and the like. Particularly, pyrene derivatives are preferable because of 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) N, N'-bis (dibenzofuran-2-yl) -N, N'-diphenylpyrene-1,6-diamine (abbreviation: 1,6 FrAPrn), 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 ] [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- (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- ( , 10-Diphenyl-2-anthryl) phenyl] -9H-carbazol-3-amine (abbreviation: 2PCAPPA), N- [4- (9,10-diphenyl-2-anthryl) phenyl] -N, N ′, N It is possible to use '-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA) or the like.

In addition, as a light-emitting substance that converts triplet excitation energy into light emission, for example, a substance that emits phosphorescence (phosphorescent material) and thermally activated delayed fluorescence (TADF) material that exhibits thermally activated delayed fluorescence can be mentioned. .

Examples of the phosphorescent material include organic metal complexes, metal complexes (platinum complexes), and rare earth metal complexes. Since these exhibit different emission colors (emission peaks) for each substance, they are appropriately selected and used as needed.

As a phosphorescent material which exhibits blue or green and has a peak wavelength of emission spectrum of 450 nm or more and 570 nm or less, the following substances may be mentioned.

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 [3- (5-biphenyl) -5-isopropyl-4-phenyl-4H-1,2,4-triazolato] iridium (III) _{(abbreviation: [Ir (iPr5btz) 3]} ), like An organometallic complex having a 4H-triazole skeleton, tris [3-methyl-1- (2-methylphenyl) -5-phenyl-1H-1,2,4-triazolato] iridium (III) (abbreviation: [Ir (Mptz1) -Mp) ₃ ]), tris (1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato) iridium (III) (abbreviation: [Ir (Prptz1-Me) ₃ ]) and the like Organometallic complex having a 1H-triazole 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) _{: [Ir (dmpimpt-Me)} 3] an organometallic complex having an imidazole skeleton, such as), 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) acetylacetonate (abbreviation: FIracac) having a electron-withdrawing group such as Organometallic complexes of phenylpyridine derivative ligand.

As a phosphorescent material which exhibits a green or yellow color and has a peak wavelength of emission spectrum of 495 nm or more and 590 nm or less, the following substances can be mentioned.

For example, tris (4-methyl-6-phenylpyrimidinato) iridium (III) (abbreviation: [Ir (mppm) 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- (2-) Norbornyl) -4-phenylpyrimidinato] iridium (III) (abbreviation: [Ir (nbppm) ₂ (acac)]), (acetylacetona) G) Bis [5-methyl-6- (2-methylphenyl) -4-phenylpyrimidinato] iridium (III) (abbreviation: [Ir (mpm ppm) ₂ (acac)]), (acetylacetonato) bis { 4,6-Dimethyl-2- [6- (2,6-dimethylphenyl) -4-pyrimidinyl-κN3] phenyl-κC} iridium (III) (abbreviation: [Ir (dmppm-dmp) ₂ (acac)]) , (Acetylacetonato) bis (4,6-diphenylpyrimidinato) iridium (III) (abbreviation: Organometallic complex having a pyrimidine skeleton such as [Ir (dppm) ₂ (acac)]), (acetylacetonato) ) bis (3,5-dimethyl-2-phenylpyrazinato) iridium (III) _{(abbreviation: [Ir (mppr-Me)} 2 (acac)]), ( Sechiruasetonato) bis (5-isopropyl-3-methyl-2-phenylpyrazinato) iridium (III) _{(abbreviation: [Ir (mppr-iPr)} 2 (acac)]) organometallic complex having a pyrazine skeleton, such as, Tris (2-phenylpyridinato-N, C ^{2 ′} ) iridium (III) (abbreviation: [Ir (ppy) ₃ ]), bis (2-phenyl pyridinato-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-phenylquinolinato -N, C ^{2 ')} b Indium (III) _{(abbreviation: [Ir (pq) 3]} ), bis (2-phenylquinolinato--N, C ^{2 ')} iridium (III) acetylacetonate _{(abbreviation: [Ir (pq) 2 (} acac)] An organometallic complex having a pyridine skeleton such as bis), 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) An organic compound such as bis (2-phenylbenzothiazolato-N, C ^{2 ′} ) iridium (III) acetylacetonate (abbreviation: [Ir (bt) ₂ (acac)]) Other than metal complexes, rare earth metal complexes such as tris (acetylacetonato) (monophenanthroline) terbium (III) (abbreviation: [Tb (acac) ₃ (Phen)]) can be given.

As a phosphorescent material which exhibits yellow or red and has a peak wavelength of 570 nm or more and 750 nm or less in the light emission spectrum, the following substances may be mentioned.

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 (d1 npm) ₂ (dpm)]), an organometallic complex having a pyrimidine skeleton, (acetylacetonato) bis (2,3,5-triphenyl) Pirajinato) 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) An organometallic complex having a pyrazine skeleton such as (abbreviation: [Ir (Fdpq) ₂ (acac)]), tris (1-phenylisoquinolinato-N, C ^{2 ′} ) iridium (III) (abbreviation: [Ir (Piq) ₃ ]), bis (1-phenylisoquinolinato-N, C ^{2 ′} ) iridium (III) acetylacetonate (abbreviation: [Ir (piq) ₂ (acac)]) has a pyridine skeleton such as Organometallic complexes, 2,3,7,8,12,13,17,18-octaethyl-21H, 23H-porphyrin platinum (II) (abbreviation: [PtOEP ) Platinum complex, tris such as (1,3-diphenyl-1,3-propanedionato) (monophenanthroline) europium (III) _{(abbreviation: [Eu (DBM) 3 (} Phen)]), tris [1- Examples include rare earth metal complexes such as (2-thenoyl) -3,3,3-trifluoroacetonato] (monophenanthroline) europium (III) (abbreviation: [Eu (TTA) ₃ (Phen)]).

As organic compounds (host materials and assist materials) used for the light emitting layer (113, 113a, 113b, 113c), one or plural kinds of substances having energy gaps larger than the energy gap of the light emitting substance (guest material) are selected It may be used. In addition, materials listed as the above-mentioned hole transporting material and materials listed as the electron transporting material described later can also be used as such an organic compound (host material, assist material).

When the light-emitting substance is a fluorescent material, it is preferable to use, as the host material, an organic compound having a large energy level in a singlet excited state and a small energy level in a triplet excited state. 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 a host material, but a substance that satisfies the above conditions is more preferable. For example, anthracene derivatives and tetracene derivatives are also suitable.

Therefore, as a host material to be combined with a fluorescent light-emitting substance, 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 a triplet excitation energy larger than the triplet excitation energy of the light-emitting substance (the energy difference between the ground state and the triplet excited state) 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 a host material, but a substance that satisfies the above conditions is more preferable. For example, fused polycyclic aromatic compounds such as anthracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives, dibenzo [g, p] chrysene derivatives, and the like are also suitable.

Therefore, as a host material to be combined with a phosphorescent light-emitting substance, for example, 9,10-diphenylanthracene (abbreviation: DPAnth), 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-tetraa (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 layer (113, 113a, 113b, 113c), it is preferable to use a compound which forms an exciplex with a phosphorescent substance. Note that, with such a configuration, 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 appropriately combined and used, but in order to efficiently form an excited complex, a compound that easily receives holes (hole transportable material) and a compound that easily receives electrons (electrons It is particularly preferred to combine with a transportable material).

TADF material refers to a material that can up-convert a triplet excited state to a singlet excited state with slight thermal energy (reverse intersystem crossing) and efficiently exhibit light emission (fluorescence) from the singlet excited state. is there. In addition, as a condition under which thermally activated delayed fluorescence can be efficiently obtained, 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 It can be mentioned. Moreover, the delayed fluorescence in the TADF material refers to light emission having a remarkably long life while having the same spectrum as normal fluorescence. The lifetime is 10 ^-6 seconds or more, preferably 10 ^-3 seconds or more.

Examples of TADF materials include fullerene and derivatives thereof, acridine derivatives such as proflavin, eosin and the like. In addition, metal-containing porphyrins including magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), palladium (Pd) and the like can be mentioned. Examples of the metal-containing porphyrin 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-4 Me)), octaethylporphyrin-tin fluoride complex (SnF ₂ (OEP)), ethioporphyrin-tin fluoride complex (SnF ₂ (Etio I)), octaethyl porphyrin-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-dihydrophenazine-10-yl) phenyl] -4,5-diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3- (9, 9- Dimethyl- H-acridin-10-yl) -9H-xanthen-9-one (abbreviation: ACRXTN), bis [4- (9,9-dimethyl-9,10-dihydroacridine) phenyl] sulfone (abbreviation: DMAC-DPS) Π-electron excess heteroaromatic ring and π electron-deficient heteroaromatic ring such as 10-phenyl-10H, 10'H-spiro [acridin-9,9'-anthracene] -10'-one (abbreviation: ACRSA) The heterocyclic compound which it has can be used. The substance in which the π electron excess heteroaromatic ring and the π electron deficiency heteroaromatic ring are directly bonded has both the donor property of the π electron excess heteroaromatic ring and the acceptor activity of the π electron deficiency heteroaromatic ring. It is particularly preferable because the energy difference between the singlet excited state and the triplet excited state is reduced.

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

The light emitting layers (113, 113a, 113b, 113c) can be formed by appropriately using the above materials. Further, the above materials can be used to form 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 transporting layer 114a is formed over the light emitting layer 113a of the EL layer 103a. In addition, after the EL layer 103a and the charge generation layer 104 are formed, the electron transport layer 114b is formed over the light emitting layer 113b of the EL layer 103b.

<Electron transport layer>
The electron transport layer (114, 114a, 114b) emits light injected from the second electrode 102 or the charge generation layer (104) by the electron injection layer (115, 115a, 115b) to the light emitting layer (113, 113a, 113b). Transport to the Note that the electron transporting layers (114, 114a, 114b) are layers containing an electron transporting material. The electron transporting material used for the electron transporting layer (114, 114a, 114b) is preferably a substance having an electron mobility of 1 × 10 ⁻⁶ cm ² / Vs or more. Note that materials that can transport electrons more than holes can be used.

As the electron transporting material, metal complexes having a quinoline skeleton, metal complexes having a benzoquinoline skeleton, metal complexes having an oxazole skeleton, metal complexes having a thiazole skeleton, etc., oxadiazole derivatives, triazole derivatives, imidazole derivatives, 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 π-electron deficiency including nitrogen-containing heteroaromatic compounds Materials having high electron transportability such as heteroaromatic compounds can be used.

Specific examples of the electron transporting material include tris (8-quinolinolato) aluminum (III) (abbreviation: Alq ₃ ), tris (4-methyl-8-quinolinolato) aluminum (III) (abbreviation: Almq ₃ ), and bis ( 10-hydroxybenzo [h] quinolinato) beryllium (II) (abbreviation: BeBq ₂ ), bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (III) (abbreviation: BAlq), bis (8) -Quinolinolato) metal complexes having a quinoline skeleton such as zinc (II) (abbreviation: Znq) or a benzoquinoline skeleton, bis [2- (2-benzoxazolyl) phenolato] zinc (II) (abbreviation: ZnPBO), bis [2- (2-Benzothiazolyl) phenolato] zinc (II) (abbreviation: ZnBTZ), bis [2- (2- (2-) Rokishifeniru) -benzothiazolato] zinc (II) (abbreviation: Zn _{(BTZ) 2)} metal complex having oxazole skeleton or thiazole skeleton of the like.

In addition to metal complexes, 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis [5- (4) p-tert-Butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD-7), 9- [4- (5-phenyl-1,3,4-oxadiazole) Oxadiazole derivatives such as -2-yl) phenyl] -9H-carbazole (abbreviation: CO11), 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: such as p-EtTAZ) An azole derivative, 2,2 ′, 2 ′ ′-(1,3,5-benzenetriyl) tris (1-phenyl-1H-benzoimidazole) (abbreviation: TPBI), 2- [3- (dibenzothiophene-4) Imidazole derivatives (including benzimidazole derivatives) such as -yl) phenyl] -1-phenyl-1H-benzoimidazole (abbreviation: mDBTBIm-II) and 4,4'-bis (5-methylbenzoxazol-2-yl) ) Oxazole derivatives such as stilbene (abbreviation: BzOs), bathophenanthroline (abbreviation: Bphen), bathocuproin (abbreviation: BCP), 2,9-bis (naphthalen-2-yl) -4,7-diphenyl-1,10- Phenanthroline derivatives such as phenanthroline (abbreviation: NBphen), 2- [3- (dibenzothione) -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] dibe Quinoxaline derivatives such as nzo [f, h] quinoxaline (abbr .: 6mDBTPDBq-II) or dibenzoquinoxaline derivatives, 3,5-bis [3- (9H-carbazol-9-yl) phenyl] pyridine (abbr .: 35DCzPPy) And pyridine derivatives such as 1,3,5-tri [3- (3-pyridyl) phenyl] benzene (abbreviation: TmPyPB); 4,6-bis [3- (phenanthrene-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 A pyrimidine derivative such as pyrimidine (abbreviation: 4,6mCzP2Pm), 2- {4- [3- (N-phenyl-) H- carbazol-3-yl) -9H- carbazol-9-yl] phenyl} -4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn) can be used triazine derivatives and the like.

In addition, poly (2,5-pyridinediyl) (abbreviation: PPy), poly [(9,9-dihexylfluorene-2,7-diyl) -co- (pyridine-3,5-diyl)] (abbreviation: PF -Py), as high as poly [(9,9-dioctyl fluorene-2,7-diyl) -co- (2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy) Molecular compounds can also be used.

The electron-transporting layer (114, 114a, 114b) is not limited to a single layer, and may have a structure in which two or more layers containing the above substances are stacked.

Next, in the light emitting element shown in FIG. 1D, the electron injection layer 115a is formed on the electron transporting layer 114a of the EL layer 103a by a vacuum evaporation method. Thereafter, the EL layer 103a and the charge generation layer 104 are formed, and the electron transport layer 114b of the EL layer 103b is formed, and then the electron injection layer 115b is formed thereon by a vacuum evaporation method.

<Electron injection layer>
The electron injection layer (115, 115a, 115b) is a layer containing a substance having a high electron injection property. In the electron injection layer (115, 115a, 115b), an alkali metal such as lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), lithium oxide (LiO _x ), etc., alkali Earth metals or compounds thereof can be used. Alternatively, a rare earth metal compound such as erbium fluoride (ErF ₃ ) can be used. Alternatively, electride may be used for the electron injection layer (115, 115a, 115b). Examples of electride include a substance in which electrons are added to a mixed oxide of calcium and aluminum at a high concentration, and the like. In addition, the substance which comprises the electron carrying layer (114, 114a, 114b) mentioned above can also be used.

Alternatively, a composite material formed by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer (115, 115a, 115b). Such a composite material is excellent in electron injectability and electron transportability 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, and specifically, for example, an electron transporting material (metal complex used for the electron transporting layer (114, 114a, 114b) described above And heteroaromatic compounds etc. can be used. As the electron donor, any substance may be used as long as it exhibits an electron donating property to the organic compound. Specifically, alkali metals, alkaline earth metals and rare earth metals are preferable, and lithium, cesium, magnesium, calcium, erbium, ytterbium and the like can be mentioned. Further, alkali metal oxides and alkaline earth metal oxides are preferable, and lithium oxide, calcium oxide, barium oxide and the like can be mentioned. Also, Lewis bases such as magnesium oxide can be used. Alternatively, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used.

In the light-emitting element illustrated in FIG. 1D, in the case of amplifying light obtained from the light-emitting layer 113b, the optical distance between the second electrode 102 and the light-emitting layer 113b is equal to that of light that the light-emitting layer 113b exhibits. Preferably, it is formed to be less than 1⁄4 of the wavelength λ. In this case, the thickness can be adjusted by changing the film thickness of the electron transport layer 114 b or the electron injection layer 115 b.

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

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

In the case where the charge generation layer 104 has a structure in which an electron donor is added to the electron transport material, the material described in this embodiment can be used as the electron transport material. As the electron donor, an alkali metal, an alkaline earth metal, a rare earth metal, a metal belonging to Groups 2 and 13 of the periodic table, or an oxide or carbonate thereof can be used. Specifically, lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), ytterbium (Yb), indium (In), lithium oxide, cesium carbonate or the like is preferably used. In addition, an organic compound such as tetrathianaphthacene may be used as the electron donor.

<Board>
The light-emitting elements described in this embodiment can be formed over various substrates. In addition, the kind of board | substrate is not limited to a specific thing. Examples of the substrate include a semiconductor substrate (for example, a single crystal substrate or a silicon substrate), an SOI substrate, a glass substrate, a quartz substrate, a plastic substrate, a metal substrate, a stainless steel still substrate, a substrate having a stainless steel foil, a tungsten substrate, A substrate having a tungsten foil, a flexible substrate, a laminated film, a paper containing a fibrous material, or a base film may be mentioned.

In addition, barium borosilicate glass, alumino borosilicate glass, soda lime glass etc. are mentioned as an example of the material of a glass substrate. In addition, as an example of a flexible substrate, a laminated film, a base film, etc., plastics represented by polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyether sulfone (PES), acrylic resins, etc. Synthetic resins, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyamide, polyimide, aramid resin, epoxy resin, inorganic vapor deposition film, papers, etc. may be mentioned.

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. In the case of using vapor deposition, physical vapor deposition (PVD) such as sputtering, ion plating, ion beam deposition, molecular beam deposition, vacuum deposition, chemical vapor deposition (CVD) or the like is used. be able to. In particular, functional layers (hole injection layers (111, 111a, 111b), hole transport layers (112, 112a, 112b), light emitting layers (113, 113a, 113b, 113c), and electron transport included in the EL layer of the light emitting device) For the layer (114, 114a, 114b), the electron injection layer (115, 115a, 115b), and the charge generation layer (104, 104a, 104b), a vapor deposition method (vacuum vapor deposition method etc.), a coating method (dip coat method) , Die coating method, bar coating method, spin coating method, spray coating method, etc., printing method (ink jet method, screen (stencil printing) method, offset (planographic printing) method, flexo (letterpress printing) method, gravure method, micro contact It can form by methods, such as a method and a nanoimprint method.

Note that functional layers (hole injection layers (111, 111a, and 111b) and hole transport layers (112, 112a, and 112b) included in the EL layers (103, 103a, and 103b) of the light-emitting element described in this embodiment mode) , The light emitting layer (113, 113a, 113b, 113c), the electron transport layer (114, 114a, 114b), the electron injection layer (115, 115a, 115b)) and the charge generation layer (104, 104a, 104b) are described above. There is no limitation to the materials, and any other materials can be used in combination as long as they can satisfy the function of each layer. As an example, it is possible to use a high molecular compound (oligomer, dendrimer, polymer etc.), a medium molecular compound (compound of intermediate region of low molecule and high molecule: molecular weight 400 to 4000), inorganic compound (quantum dot material etc.) it can. In addition, as the quantum dot material, a colloidal quantum dot material, an alloy type quantum dot material, a core / shell type quantum dot material, a core type quantum dot material, or the like can be used.

The structure described in this embodiment can be used in appropriate combination with the structure described in any of the other embodiments.

Third Embodiment
In this embodiment mode, a light-emitting device which is one embodiment of the present invention will be described. Note that in the light-emitting device illustrated in FIG. 2A, active matrix light emission in which a transistor (FET) 202 on a first substrate 201 and a light-emitting element (203R, 203G, 203B, 203W) are electrically connected to each other The 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 is different according to the light emitting color of each light emitting element. It has a tuned microcavity structure. In addition, it is a top emission type light emitting device in which light emission obtained from the EL layer 204 is emitted through the color filters (206R, 206G, and 206B) formed on the second substrate 205.

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

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 203R is adjusted so that the optical distance 200R is between the first electrode 207 and the second electrode 208, and the light emitting element 203G includes the first electrode 207 and the second electrode. The light distance between the light emitting element 203B and the second electrode 208 is adjusted to be an optical distance 200B. Note that as shown in FIG. 2B, optical adjustment can be performed by stacking the conductive layer 210R over the first electrode 207 in the light emitting element 203R and stacking the conductive layer 210G in the light emitting element 203G.

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

Although FIG. 2A shows a light emitting device having a structure (top emission type) for emitting light to the second substrate 205 side, a first substrate in which an FET 202 is formed as shown in FIG. 2C. The light-emitting device may have a structure (bottom emission type) in which light is extracted to the side 201. 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 and semi-reflective electrode, and the second electrode 208 is formed to function as a reflective electrode. In addition, the first substrate 201 uses at least a light-transmitting substrate. The color filters (206R ′, 206G ′, and 206B ′) may be provided closer to the first substrate 201 than the light-emitting elements (203R, 203G, and 203B) as illustrated in FIG. 2C.

Although 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, the light-emitting element of one embodiment of the present invention is limited to that structure. Alternatively, a yellow light emitting element or an orange light emitting element may be provided. In addition, as materials used for an EL layer (a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge generation layer, etc.) for producing these light emitting elements, other embodiments are It may be used as appropriate with reference to the description of the embodiment. In that case, it is also necessary to appropriately select a color filter in accordance with the light emission color of the light emitting element.

By adopting the above-described configuration, it is possible to obtain a light emitting device provided with a light emitting element exhibiting a plurality of light emitting colors.

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

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

By applying the element configuration 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 passive matrix light-emitting devices and active matrix light-emitting devices 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 is described with reference to FIG.

3A is a top view showing the light emitting device 21, and FIG. 3B is a cross-sectional view of FIG. 3A taken along a dashed line A-A '. 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, 304 a, 304 b) are sealed between the first substrate 301 and the second substrate 306 by the sealant 305.

In addition, over the first substrate 301, a lead wiring 307 is provided. The lead wiring 307 is electrically connected to the FPC 308 which is an external input terminal. Note that the FPC 308 transmits signals (eg, video signals, clock signals, start signals, reset signals, and the like) and potentials from the outside to the driver circuit units (303, 304a, and 304b). In addition, a printed wiring board (PWB) may be attached to the FPC 308. Note that the state in which the FPC and the PWB are attached is included in the light emitting device.

Next, a cross-sectional structure is shown in FIG.

The pixel portion 302 is formed of a plurality of pixels including a FET (switching FET) 311, an 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 set as needed.

The

FETs

309, 310, 311, and 312 are not particularly limited, and, for example, transistors such as a staggered transistor or an inverted staggered transistor can be applied. In addition, a top gate type or bottom gate type transistor structure may be employed.

The crystallinity of the semiconductor that can be used for these

FETs

309, 310, 311, and 312 is not particularly limited, and an amorphous semiconductor, a semiconductor having crystallinity (a microcrystalline semiconductor, a polycrystalline semiconductor, a single crystal semiconductor, Alternatively, any of semiconductors each having a crystal region in part may be used. Note that using a semiconductor having crystallinity is preferable because deterioration of transistor characteristics can be suppressed.

Moreover, as these semiconductors, for example, an element of Group 14, a compound semiconductor, an oxide semiconductor, an organic semiconductor, or 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 driver circuit portion 303 includes an FET 309 and an FET 310. Note that the FET 309 and the FET 310 may be formed by a circuit including a unipolar (N-type or P-type) transistor, or may be formed by a CMOS circuit including an N-type transistor and a P-type transistor. It is good. In addition, a driver circuit may be provided outside.

The 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. . The insulator 314 preferably has a curved surface having a curvature at the upper end or the lower end. Thereby, the coverage of the film formed in the upper layer of the insulator 314 can be made favorable.

An EL layer 315 and a second electrode 316 are stacked over the first electrode 313. The EL layer 315 includes a light emitting layer, a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron injecting layer, a charge generation layer, and the like.

Note that the structure and materials described in the 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 in FIG. 3B, a plurality of light emitting elements are arranged in a matrix in the pixel portion 302. Light-emitting elements which can emit light of three types (R, G, and B) can be selectively formed in the pixel portion 302, so that a light-emitting device capable of full-color display can be formed. In addition to light emitting elements that can obtain three types (R, G, B) of light emissions, light emissions such as white (W), yellow (Y), magenta (M), cyan (C), etc. An element may be formed. For example, by adding light emitting elements that can obtain the above-described several types of light emission to light emitting elements that can obtain three types of light emission (R, G, B), effects such as improvement in color purity and reduction in power consumption can be obtained. Can. Alternatively, a light emitting device capable of full color display may be provided by combining with a color filter. In addition, as a kind of color filter, red (R), green (G), blue (B), cyan (C), magenta (M), yellow (Y) etc. can be used.

The FETs (309, 310, 311, and 312) and the light emitting element 317 on the first substrate 301 are attached to each other with the sealant 305 so that the second substrate 306 and the first substrate 301 are bonded to each other. A structure provided in a space 318 surrounded by the second substrate 301 and the sealing material 305 is provided. The space 318 may be filled with an inert gas (such as nitrogen or argon) or an organic substance (including the sealant 305).

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

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

In the case of forming an active matrix light-emitting device over a flexible substrate, the FET and the light-emitting element may be formed directly on the flexible substrate, but the FET and the light-emitting element may be formed over another substrate having a peeling layer. After that, the FET and the light emitting element may be separated by a peeling layer by applying heat, force, laser irradiation or the like, and may be further transferred to a flexible substrate. Note that as the peeling layer, for example, a lamination of an inorganic film of a tungsten film and a silicon oxide film, an organic resin film such as polyimide, or the like can be used. As a flexible substrate, in addition to a substrate capable of forming a transistor, a paper substrate, a cellophane substrate, an aramid film substrate, a polyimide film substrate, a cloth substrate (natural fiber (silk, cotton, linen), synthetic fiber ( Examples include nylon, polyurethane, polyester) or regenerated fibers (including acetate, cupra, rayon, regenerated polyester), leather substrates, rubber substrates and the like. By using such a substrate, it is possible to achieve excellent durability and heat resistance, and to achieve weight reduction and thickness reduction.

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

Fifth Embodiment
In this embodiment, an example of a light-emitting element which is one embodiment of the present invention and various electronic devices and vehicles which are completed by applying a light-emitting device including the light-emitting element which is 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 device 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, an operation key 7005 (including a power switch or an operation switch), a connection terminal 7006, Sensor 7007 (force, displacement, position, velocity, acceleration, angular velocity, rotation number, distance, light, liquid, magnetism, temperature, chemical substance, voice, time, hardness, electric field, current, voltage, electric power, radiation, flow rate, humidity (Including the function of measuring inclination, vibration, odor, or infrared), a microphone 7008, and the like.

FIG. 4A illustrates a mobile computer, which can include a switch 7009, an infrared port 7010, and the like in addition to the above components.

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

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

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 is shown in which the information 7052, the information 7053, and the information 7054 are displayed on different sides. For example, the user can check the information 7053 displayed at a position where it can be observed from the upper side of the portable information terminal while the portable information terminal is stored in the chest pocket of the clothes. The user can confirm the display without taking out the portable 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 the display portion 7001, an operation key 7005, and the like in the housing 7000. Note that the portable information terminal may be provided with a speaker 7003, a connection terminal 7006, a sensor 7007, and the like. In addition, the portable information terminal can display text and image information on its multiple faces. Here, an example in which three icons 7050 are displayed is shown. Further, information 7051 indicated by a dashed rectangle can be displayed on another surface of the display portion 7001. Examples of the information 7051 include notification of arrival of e-mail, SNS, telephone etc., title of e-mail or SNS, sender's name, date, time, remaining amount of battery, strength of antenna reception, etc. 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 set (also referred to as a television or a television receiver), which can include the housing 7000, the display portion 7001, and the like. Further, here, a structure in which the housing 7000 is supported by the stand 7018 is shown. In addition, the television set can be operated by a separate remote control 7111 or the like. Note that the display portion 7001 may be provided with a touch sensor, or may be operated by touching the display portion 7001 with a finger or the like. The remote controller 7111 may have a display unit for displaying information output from the remote controller 7111. Channels and volume can be controlled with an operation key or a touch panel included in the remote controller 7111, and an image displayed on the display portion 7001 can be manipulated.

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 date or time, etc., 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 out a program or data recorded in a recording medium A function to display on the display portion can be provided. Furthermore, in an electronic device having a plurality of display units, the function of displaying image information mainly on one display unit and displaying character information mainly on another display unit or considering parallax in a plurality of display units It is possible to have a function of displaying a three-dimensional image and the like by displaying the captured image. Furthermore, in an electronic device having an image receiving unit, the function of capturing a still image, the function of capturing a moving image, the function of automatically or manually correcting the captured image, the captured image in a recording medium (externally or built in a camera) A function to save, a function to display a captured image on a display portion, and the like can be provided. Note that the electronic devices illustrated in FIGS. 4A to 4F can have various functions without limitation to the above.

FIG. 4G illustrates a watch-type portable information terminal, which can be used, for example, as a smart watch. 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 can perform hands-free communication by, for example, mutual communication with a headset capable of wireless communication. Note that data can be transmitted to another information terminal with each other and charging can be performed by the connection terminal 7024. The charging operation can also be performed by wireless power feeding.

The display portion 7001 mounted in a housing 7000 which also serves as a bezel portion has a non-rectangular display area. The display unit 7001 can display an icon indicating time, another icon, and the like. Further, the display unit 7001 may be a touch panel (input / output device) on which a touch sensor (input device) is mounted.

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 date or time, etc., 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 out a program or data recorded in a recording medium A function to display on the display portion can be provided.

Also, inside the housing 7000, a speaker, a sensor (force, displacement, position, velocity, acceleration, angular velocity, rotation number, distance, light, liquid, magnetism, temperature, chemical substance, voice, time, hardness, electric field, current Voltage, power, radiation, flow rate, humidity, inclination, vibration, odor or infrared (including the function of measuring infrared), a microphone, and the like.

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

Further, as an electronic device to which the light emitting device is applied, a foldable portable information terminal as shown in FIGS. 5A to 5C can be given. FIG. 5A shows a portable information terminal 9310 in a developed state. FIG. 5B shows the portable information terminal 9310 in the middle of changing from one of the expanded state or the folded state to the other. Further, FIG. 5C shows a portable information terminal 9310 in a folded state. The portable information terminal 9310 is excellent in portability in the folded state, and in the expanded state, is excellent in viewability of display due to a wide seamless display area.

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) on which a touch sensor (input device) is mounted. In addition, the display portion 9311 can be reversibly deformed into a folded state from the expanded state by bending the space between the two housings 9315 through the hinges 9313. Note that the light-emitting device of one embodiment of the present invention can be used for the display portion 9311. In addition, a long-life electronic device 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 a folded state. An information icon, a frequently used application, a shortcut of a program, and the like can be displayed in the display area 9312, and information confirmation and activation of the application and the like can be performed 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, the present invention can be applied to the light 5101 (including the rear of the vehicle body) outside the automobile shown in FIG. 6A, the wheel 5102 of the tire, part or all of the door 5103, and the like. Further, the present invention can be applied to the display 5104, the handle 5105, the shift lever 5106, the seat 5107, the inner rear view mirror 5108, and the like inside the automobile shown in FIG. 6B. In addition, you may apply to a part of glass window.

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

Sixth Embodiment
In this embodiment, a structure of a lighting device manufactured using the light-emitting device which is one embodiment of the present invention or a light-emitting element which is a part of the light-emitting device is described with reference to FIG.

7A and 7B show an example of a cross-sectional view of the lighting device. 7A shows a bottom emission type lighting device which extracts light to the substrate side, and FIG. 7B shows a top emission type lighting device which extracts light to the sealing substrate side.

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

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

Further, the substrate 4001 and the sealing substrate 4011 are attached to each other by a sealing material 4012. In addition, 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 illustrated in FIG. 7A, the light extraction efficiency of the light-emitting element 4002 can be improved.

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

The first electrode 4204 is electrically connected to the electrode 4207, and the second electrode 4206 is electrically connected to the electrode 4208. In addition, an auxiliary wiring 4209 electrically connected to the second electrode 4206 may be provided. In addition, an insulating layer 4210 may be provided below the auxiliary wiring 4209.

The substrate 4201 and the sealing substrate 4211 with unevenness are attached with a sealant 4212. In addition, 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 the sealing substrate 4211 has unevenness as illustrated in FIG. 7B, so that the light extraction efficiency of the light-emitting element 4202 can be improved.

Moreover, as an application example of these illuminating devices, the ceiling light which is for indoor illumination is mentioned. The ceiling lights include a ceiling direct attachment type and an in-ceiling type. Note that such a lighting device is configured by combining a light emitting device with a housing or a cover.

In addition to this, it is also possible to apply the light to the floor surface to improve the safety of the foot. For example, it is effective to use a foot lamp for a bedroom, a staircase, or a passage. In that case, the size and shape can be changed as appropriate according to the size and structure of the room. Moreover, it is also possible to set it as the stationary type illuminating device comprised combining a light-emitting device and a support stand.

Moreover, it is also possible to apply as a sheet-like illuminating device (sheet-like illumination). Sheet-like lighting can be used for a wide range of applications without taking up space because it is used by being attached to a wall surface. In addition, it is easy to increase the area. In addition, it can also be used for the wall surface and case which have a curved surface.

Note that in addition to the above, the light-emitting device of one embodiment of the present invention or a light-emitting element that is a portion thereof is applied to part of furniture provided in a room, and a lighting device having a function as furniture is provided. Can.

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.

«Synthesis example 1»
In this example, an organometallic complex which is one embodiment of the present invention represented by Structural Formula (100) of Embodiment 1, bis {2- [6- (4-cyano-2,6-dimethylphenyl)- Description of the synthesis method of 4-pyrimidinyl-κN ³ ] phenyl-κC} (2,4-pentanedionato-κO, O ') iridium (III) (abbreviation: [Ir (ppm-dmCP) ₂ (acac)]) 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>
A 3-neck flask equipped with a reflux condenser was charged with 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 dimethyl sulfoxide, and the interior was nitrogen-substituted . After degassing the inside of the flask by stirring under reduced pressure, [1,1′-bis (diphenylphosphino) ferrocene] palladium (II) dichloride dichloromethane adduct (abbreviation: Pd (dppf) Cl ₂ · CH ₂ Cl ₂ ₂ ) 0.59 g and 0.59 g of 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl (abbreviation: S-Phos) were added, and the mixture was stirred at 100 DEG C. for 32 hours. After a predetermined time, extraction with toluene was performed. Then, the residue 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 the following formula (a-1).

<Step 2: Synthesis of 4- (4-cyano-2,6-dimethylphenyl) -6-phenylpyrimidine (abbreviation: Hppm-dmCP)>
Next, 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) 1.28 g of benzonitrile, 3.23 g of tripotassium phosphate, 43 mL of toluene, and 4.3 mL of water were placed in a three-necked flask equipped with a reflux condenser, and the inside was purged with nitrogen.

The inside of the flask is stirred and degassed under reduced pressure, and then 0.094 g of tris (dibenzylideneacetone) dipalladium (0) (abbreviation: Pd ₂ (dba) ₃ ), tris (2,6-dimethoxyphenyl) phosphine ( Abbreviation: 0.19 g of P (2, 6- MeOPh) ₃ ) was added, and the mixture was stirred at 110 ° C for 23 hours. After a predetermined time, extraction with toluene was performed. Then, it refine | purified by silica gel column chromatography using hexane: ethyl acetate = 5: 1 as a developing solvent, and obtained the target pyrimidine derivative, Hppm-dmCP (white solid, yield 0.97 g, yield 88%). The synthesis scheme of Step 2 is shown in the following Formula (a-2).

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

<Step 4: Synthesis of [Ir (ppm-dmCP) ₂ (acac)]>
20 mL of 2-ethoxyethanol, the binuclear complex obtained in the above step 3, 1.44 g of [Ir (ppm-dmCP) ₂ Cl] ₂ , 0.41 g of acetylacetone (abbreviation: Hacac), 0.93 g of sodium carbonate, The flask was placed in a fitted eggplant flask, and the inside of the flask was purged with argon. Thereafter, it was irradiated with microwave (2.45 GHz 100 W) for 4 hours. The obtained residue was suction filtered with dichloromethane and the filtrate was concentrated. The obtained solid is 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 obtain an organometallic complex, [Ir (ppm) -DmCP) ₂ (acac)] was obtained as a yellowish orange powder (yield 0.19 g, 7%). 0.19 g of the obtained yellow-orange powder was purified by sublimation using a train sublimation method. The sublimation purification conditions were such that the solid was heated at 355 ° C. while flowing a pressure of 2.7 Pa and flowing argon gas at a flow rate of 11 mL / min. After sublimation purification, the objective yellow-orange solid was obtained in a yield of 0.092 g, 48%. The synthesis scheme of Step 4 is shown in the following formula (a-4).

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

¹ H-NMR. δ (CDCl ₃ ): 1.86 (s, 6 H), 2. 29 (s, 12 H), 5. 36 (s, 1 H), 6. 44 (d, 2 H), 6. 86 (t, 2 H) , 6.91 (t, 2H), 7.52 (s, 4H), 7.66 (d, 2H), 7.68 (s, 2H), 9.25 (s, 2H).

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

For measurement of the absorption spectrum, a dichloromethane solution (0.011 mmol / L) was put in a quartz cell using a UV-visible spectrophotometer (V550 type manufactured by JASCO Corporation), and measurement was performed at room temperature. In addition, for the measurement of the emission spectrum, a dichloromethane deoxygenated solution (0.011 mmol / L) is put in a quartz cell under a nitrogen atmosphere using an absolute PL quantum yield measurement apparatus (C11347-01 manufactured by Hamamatsu Photonics Co., Ltd.) Sealed tightly and measured at room temperature.

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

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

In this example, as a light-emitting element which is one embodiment of the present invention, bis {2- [6- (4-cyano-2,6-dimethylphenyl) -4-pyrimidinyl-κN ³ ] phenyl described in Example 1 is described. -ΚC} (2,4-pentanedionato-κO, O ') iridium (III) (abbreviation: [Ir (ppm-dmCP) ₂ (acac)]) (structural formula (100)) was used for the light emitting layer Light-emitting element 1 and, as a light-emitting element for comparison, bis {2- [6- (2,6-dimethylphenyl) -4-pyrimidinyl-κN ³ ] phenyl-κC} (2,4-pentanedionato-κO , O ′) Iridium (III) (abbreviation: [Ir (ppm-dmp) ₂ (acac)]) (Structural Formula (200)) for the light emitting layer of the comparative light emitting element 2 Describe the characteristics . The element structure of the light emitting element used in this embodiment is shown in FIG. 10, and the specific configuration is shown in Table 1. In addition, chemical formulas of materials used in this example are shown below.

«Fabrication of light emitting element»
In the light emitting element shown in this embodiment, a hole injecting layer 911, a hole transporting layer 912, a light emitting layer 913, an electron transporting layer 914, and a first electrode 901 formed on a substrate 900 as shown in FIG. The electron injection layer 915 is sequentially stacked, and the second electrode 903 is stacked on the electron injection layer 915.

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

Here, as pretreatment, the surface of the substrate was washed with water, baked at 200 ° C. for 1 hour, and subjected to UV ozone treatment for 370 seconds. After that, the substrate is introduced into a vacuum deposition apparatus whose inside is depressurized to about 10 ^-4 Pa, and vacuum baking is performed at 170 ° C. for 30 minutes in a heating chamber in the vacuum deposition apparatus, and then the substrate is released for about 30 minutes. It was cold.

Next, the hole injecting layer 911 was formed over the first electrode 901. After reducing the pressure in the vacuum evaporation system to 10 ⁻⁴ Pa, the hole injection layer 911 is 4,4 ′, 4 ′ ′-(benzene-1,3,5-triyl) tri (dibenzothiophene) (abbreviation: DBT3P) -II) and molybdenum oxide were formed by co-evaporation such that the film thickness was 55 nm, with DBT3P-II: molybdenum oxide = 2: 1 (mass ratio).

Next, the hole transport layer 912 was formed on the hole injection layer 911. The hole transporting layer 912 was formed by evaporation using 4-phenyl-4 ′-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: BPAFLP) so that the film thickness was 20 nm.

Next, the light emitting layer 913 was formed over the hole transporting layer 912.

The light-emitting layer 913 in the case of the light-emitting element 1 uses 2mDBTBPDBq-II as a host material, PCBBiF as an assist material, and an organometallic complex which is one embodiment of the present invention as a guest material (phosphorescent material); 6- (4-Cyano-2,6-dimethylphenyl) -4-pyrimidinyl-κN ³ ] phenyl-κC} (2,4-pentanedionato-κO, O ′) iridium (III) (abbreviation: [Ir ( Using ppm-dmCP) ₂ (acac)]) (structural formula: 100), the weight ratio is 2mDBTBPDBq-II: PCBBiF: [Ir (ppm-dmCP) ₂ (acac)] = 0.75: 0.25: 0 The co-evaporation was performed so as to be .075. The film thickness was 40 nm.

The light emitting layer 913 in the case of the comparative light emitting element 2 uses 2mDBTBPDBq-II as a host material, PCBBiF as an assist material, bis {2- [6- (2, 6-dimethylphenyl) as a guest material (phosphorescent material) -4-Pyrimidinyl-κN ³ ] phenyl-κC} (2,4-pentanedionato-κO, O ') iridium (III) (abbreviation: [Ir (ppm-dmp) ₂ (acac)]), by weight The co-evaporation was performed such that the ratio was 2 m DBT BP DB q-II: PCBBiF: [Ir (ppm-dmp) ₂ (acac)] = 0.75: 0.25: 0.075. The film thickness was 40 nm.

Next, the electron transporting layer 914 was formed over the light emitting layer 913. The electron-transporting layer 914 has a film thickness of 20 nm of 2mDBTBPDBq-II and a film thickness of 15 nm of 2,9-bis (naphthalen-2-yl) -4,7-diphenyl-1,10-phenanthroline (abbr .: NBphen). It vapor-deposited one by one so that it might become.

Next, the electron injection layer 915 was formed over the electron transport layer 914. The electron injection layer 915 was formed by evaporation using lithium fluoride (LiF) so as to have 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 depositing aluminum to a thickness of 200 nm. In the present embodiment, the second electrode 903 functions as a cathode.

Through the above steps, a light-emitting element in which the EL layer 902 is sandwiched between the pair of electrodes is formed over the substrate 900. Note that the hole injecting layer 911, the hole transporting layer 912, the light emitting layer 913, the electron transporting layer 914, and the electron injecting layer 915 described in the above steps are functional layers which form the EL layer in one embodiment of the present invention. Further, in the vapor deposition step in the above-described manufacturing method, all vapor deposition methods using resistance heating were used.

In addition, the light emitting element manufactured as described above is sealed by another substrate (not shown). Note that when sealing using another substrate (not shown), another substrate (not shown) coated with a sealant that solidifies with ultraviolet light is placed on the substrate 900 in a glove box under a nitrogen atmosphere. The substrates were fixed so that the sealant was attached around the light emitting element formed on the substrate 900. At the time of sealing, the sealing agent was solidified by irradiating ultraviolet light of 365 nm at 6 J / cm ^2, and the sealing agent was stabilized by heat treatment at 80 ° C. for 1 hour.

<< Operation characteristics of light emitting element >>
It measured about the operating characteristic of each produced light emitting element. The measurement was performed at room temperature (in the atmosphere kept at 25 ° C.). The results are shown in FIG. 11 to FIG.

Table 2 below shows main initial characteristic values of each light emitting element in the vicinity of 1000 cd / m ² .

From the above results, the light emitting device 1 exhibits excellent device characteristics, but in particular, high external quantum efficiency is obtained as compared to the comparative light emitting device 2. This can be understood as the effect of using the organometallic complex which is one embodiment of the present invention, [Ir (ppm-dmCP) ₂ (acac)], in the light emitting layer of the light emitting element 1.

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

In addition, FIG. 15 shows emission spectra when current is supplied 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, the light-emitting element 1 has a light emission spectrum having a peak in the vicinity of 574 nm, which is derived from light emission of an organometallic complex contained in the light-emitting layer 913, [Ir (ppm-dmCP) ₂ (acac)]. The comparative light-emitting element 2 also has a light emission spectrum having a peak at around 559 nm, which is derived from light emission of an organometallic complex contained in the light-emitting layer 913, [Ir (ppm-dmp) ₂ (acac)]. The maximum light emission wavelength of the light emitting element 1 is shifted in the long wavelength direction compared to the comparative light emitting element 2. This is because, in the light-emitting element 1, an organic metal complex contained in the light-emitting layer 913, [Ir (ppm-dmCP) ₂ (acac)], the phenyl group which the pyrimidine ring of the ligand has has a cyano group as a substituent By having it, it is because LUMO of a ligand falls. Therefore, when it is desired to shift the maximum light emission wavelength to the long wavelength direction and adjust the light emission wavelength to the red light emission region, it can be said that the organometallic complex which is one embodiment of the present invention is suitable.

Next, the reliability test for the light emitting element 1 and the comparative light emitting element 2 was performed. The results of the reliability test are shown in FIG. In FIG. 16, the vertical axis represents normalized luminance (%) when the initial luminance is 100%, and the horizontal axis represents driving time (h) of the element. 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 the effect of using the organometallic complex which is one embodiment of the present invention, [Ir (ppm-dmCP) ₂ (acac)] (structural formula (100)) for the light emitting layer of the light emitting element 1. [Ir (ppm-dmCP) ₂ (acac)] has a feature that it is difficult to be decomposed and has high heat resistance despite having a high sublimation temperature because of having a cyano group as a substituent on the molecular structure. Therefore, since high purity [Ir (ppm-dmCP) ₂ (acac)] can be used without causing thermal decomposition by sublimation purification, it can be said that the reliability of the light-emitting element 1 is improved.

Also, in order to analyze the desorbed gas generated in the deposition chamber during deposition of the light emitting layers of the light emitting element 1 and the comparative light emitting element 2, a quadrupole mass spectrometer (residue gas analyzer Qulee BGM-, manufactured by ULVAC, Inc.) The pressure (detection partial pressure: Pa) of the specific gas corresponding to the mass-to-charge ratio in the measurement gas inside the chamber was measured using 202). The results are shown in FIG. In FIG. 17, the abscissa represents the mass-to-charge ratio (m / z), and the ordinate represents the pressure of a specific gas (detected partial pressure: Pa) corresponding to the mass-to-charge ratio. In addition, B. in FIG. G. These are the results of measuring the pressure (detection partial pressure: Pa) of the specific gas 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 for the light emitting layer of the light emitting element 1 was used for the light emitting layer of the comparative light emitting element 2, [Ir (ppm-dmp) ₂ (acac) Although the sublimation temperature was high, the detection of the desorbed gas component was less than that of the above. From this, it can be said that [Ir (ppm-dmCP) ₂ (acac)] is less likely to be thermally decomposed than [Ir (ppm-dmp) ₂ (acac)]. That is, although the organometallic complex [Ir (ppm-dmCP) ₂ (acac)] synthesized in this example contains a cyano group as a substituent, it is difficult to be thermally decomposed although the sublimation temperature is increased. It was confirmed that this was a structure (it was difficult to form low molecular weight degradation products).

«Synthesis example 2»
In this example, an organometallic complex which is one embodiment of the present invention, which is represented by a structural formula (112) of Embodiment 1, bis {4,6-dimethyl-2- [6- (5-cyano-2-) Methylphenyl) -4-pyrimidinyl-κN ³ ] phenyl-κC} (2,2,6,6-tetramethyl-3,5-heptanedionato-κ ² O, O ′) iridium (III) (abbreviation: [Ir ( The synthesis method of dmppm-m5CP) ₂ (dpm)] is demonstrated. The structure of [Ir (dmppm-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 2 M aqueous sodium carbonate solution, and 360 mL of ethylene glycol dimethyl ether (abbreviation: DME) are placed in a three-necked flask equipped with a reflux condenser, Were replaced with nitrogen. After degassing the inside of the flask by stirring under reduced pressure, 0.67 g of palladium (II) acetate (abbreviation: Pd (OAc) ₂ ) and 1.61 g of triphenylphosphine (abbreviation: PPh ₃ ) are added, and 110 ° C. is added. The mixture was stirred for 11 hours. After a predetermined time, extraction with ethyl acetate was performed. Then, the residue 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 the following formula (b-1).

<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, 15.32 g of tripotassium phosphate Then, 240 mL of toluene and 24 mL of water were placed in a three-necked flask equipped with a reflux condenser, and the inside was purged with nitrogen.

The inside of the flask is stirred and degassed under reduced pressure, and then 0.88 g of tris (dibenzylideneacetone) dipalladium (0) (abbreviation: Pd ₂ (dba) ₃ ), tris (2,6-dimethoxyphenyl) phosphine ( Abbreviation: 1.68 g of (2,6-MeOPh) ₃ P) was added, and the mixture was stirred at 110 ° C. for half an hour. After a predetermined time, extraction with toluene was performed. Then, the target pyrimidine derivative, Hdmppm-m5CP, was obtained by purification with silica gel column chromatography using dichloromethane: ethyl acetate = 20: 1 as a developing solvent (white solid, yield 4.31 g, yield 60%). The synthesis scheme of step 2 is shown in the following formula (b-2).

<Step 3: Di-μ-chloro-tetrakis {4,6-dimethyl-2- [6- (5-cyano-2-methylphenyl) -4-pyrimidinyl-κN ³ ] phenyl-κC} diiridium (III) Synthesis of (abbreviation: [Ir (dmppm-m5CP) ₂ Cl] ₂ )>
Next, 30 mL of 2-ethoxyethanol and 10 mL of water, 3.92 g of Hdmppm-m5CP (abbreviation) obtained in the above step 2, and 1.81 g of iridium chloride hydrate (IrCl ₃ · H ₂ O) (manufactured by Furuya Metal Co., Ltd.) Was placed in a round-bottomed flask equipped with a reflux condenser, and the inside of the flask was purged with argon. Thereafter, microwave (2.45 GHz 100 W) was irradiated for 3 and a half hours to cause reaction. After a predetermined time elapsed, the obtained residue was suction-filtered and washed with methanol to obtain a dinuclear complex [Ir (dmppm-m5CP) ₂ Cl] ₂ (orange solid, yield 4.49 g, yield 91%). In addition, a 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 ³ ] phenyl-κC} (2,2,6,6-tetramethyl Synthesis of 3,5-heptanedionato-κ ² O, O ') iridium (III) (abbreviation: [Ir (dmppm-m5CP) ₂ (dpm)]>
Next, 20 mL of 2-ethoxyethanol, the binuclear complex obtained in the above step 3, 4.48 g of [Ir (dmppm-m5CP) ₂ Cl] ₂ , 1.51 g of dipivaloylmethane (abbreviation: Hdpm), sodium carbonate 2 .90g was put into an eggplant flask equipped with a reflux condenser, and the inside of the flask was purged with argon.

Thereafter, microwave (2.45 GHz 100 W) was irradiated for 6 hours. The obtained residue was suction filtered with dichloromethane and the filtrate was concentrated. The obtained solid was purified by silica gel column chromatography using dichloromethane as a developing solvent to obtain an organic metal complex, [Ir (dmppm-m5CP) ₂ (dpm)] as a red solid (yield: 0.028 g, Yield 0.5%). The synthesis scheme of Step 4 is shown in the following formula (b-4).

The analysis result by nuclear magnetic resonance spectroscopy ( ¹ H-NMR) of the red solid obtained in Step 4 is shown below. In addition, a ¹ H-NMR chart is shown in FIG. From this result, it is found that the organometallic complex represented by the above structural formula (112), [Ir (dmppm-m5CP) ₂ (dpm)] was obtained in this example.

¹ H-NMR. δ (CDCl ₃ ): 0.89 (s, 18 H), 1.52 (s, 6 H), 2. 29 (s, 6 H), 2.54 (s, 6 H), 5.62 (s, 1 H) , 6.66 (s, 2 H), 7.48-7.52 (m, 4 H), 7.68 (d, 2 H), 7.86 (d, 4 H), 8.89 (s, 2 H).

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

For measurement of the absorption spectrum, a dichloromethane solution (0.010 mmol / L) was put in a quartz cell using a UV-visible spectrophotometer (V550 type manufactured by JASCO Corporation), and measurement was performed at room temperature. In addition, for measurement of the emission spectrum, a dichloromethane deoxygenated solution (0.010 mmol / L) is put into a quartz cell under a nitrogen atmosphere using an absolute PL quantum yield measurement apparatus (C11347-01 manufactured by Hamamatsu Photonics Co., Ltd.) Sealed tightly and measured at room temperature.

The measurement results of the obtained absorption spectrum and emission spectrum are shown in FIG. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. The thin solid line in FIG. 19 indicates the absorption spectrum, and the thick solid line indicates the emission spectrum. In addition, the absorption spectrum shown in FIG. 19 shows the result which deducted the absorption spectrum which put only dichloromethane into the quartz cell and measured it from the absorption spectrum which put the dichloromethane solution (0.010 mmol / L) into the quartz cell and measured.

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

«Synthesis example 3»
In this example, an organometallic complex which is one embodiment of the present invention, which is represented by a structural formula (114) of Embodiment 1, bis {4,6-dimethyl-2- [6- (2-cyano-6-) Methylphenyl) -4-pyrimidinyl-κN ³ ] phenyl-κC} (2,2,6,6-tetramethyl-3,5-heptanedionato-κ ² O, O ′) iridium (III) (abbreviation: [Ir ( The synthesis method of dmppm-m2CP) ₂ (dpm)] is demonstrated. The structure of [Ir (dmppm-m2CP) ₂ (dpm)] is shown below.

<Step 1: Synthesis of 4- (2-cyano-6-methylphenyl) -6- (3,5-dimethylphenyl) pyrimidine>
2.18 g of 4-chloro-6- (3,5-dimethylphenyl) pyrimidine, 2.90 g of 3-methyl-2- (tetramethyl-1,3,2-dioxaborolan-2-yl) benzonitrile, phosphoric acid 3 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 condenser, and the inside was purged with nitrogen.

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

<Step 2: Di-μ-chloro-tetrakis {4,6-dimethyl-2- [6- (2-cyano-6-methylphenyl) -4-pyrimidinyl-κN ³ ] phenyl-κC} diiridium (III) Synthesis of (abbreviation: [Ir (dmppm-m2CP) ₂ Cl] ₂ )>
Next, 30 mL of 2-ethoxyethanol and 10 mL of water, 2.08 g of Hdmppm-m2CP (abbreviation) obtained in the above step 1, and 1.01 g of iridium chloride hydrate (IrCl ₃ · H ₂ O) (manufactured by Furuya Metal Co., Ltd.) Was placed in a round-bottomed flask equipped with a reflux condenser, and the inside of the flask was purged with argon. Thereafter, microwave (2.45 GHz 100 W) was irradiated for 2 hours to react. After lapse of a predetermined time, the obtained residue was suction-filtered and washed with methanol to obtain a dinuclear complex [Ir (dmppm-m2CP) ₂ Cl] ₂ (reddish brown solid, yield 1.88 g, yield 69%). In addition, a synthesis scheme of Step 2 is shown in the following formula (c-2).

<Step 3: Synthesis of [Ir (dmppm-m2CP) ₂ (dpm)]>
Next, 30 mL of 2-ethoxyethanol, the binuclear complex obtained in the above step 2, 1.86 g of [Ir (dmppm-m2CP) ₂ Cl] _2, 0.61 g of dipivaloylmethane (abbreviation: Hdpm), sodium carbonate 1 18 g of the solution was placed in a round-bottomed flask equipped with a reflux condenser, and the inside of the flask was purged with argon. Then, it was irradiated for 5 hours with microwave (2.45 GHz 100 W). The obtained residue was suction filtered with dichloromethane and the filtrate was concentrated. The obtained solid was purified by silica gel column chromatography using dichloromethane as a developing solvent to obtain an organic metal complex, [Ir (dmppm-m2CP) ₂ (dpm)] as a red solid (yield 0.050 g, 2% yield). The synthesis scheme of Step 3 is shown in the following formula (c-3).

The analysis result by nuclear magnetic resonance spectroscopy ( ¹ H-NMR) of the red solid obtained in Step 3 is shown below. In addition, a ¹ H-NMR chart is shown in FIG. From this result, it is found that the organometallic complex represented by the above structural formula (114), [Ir (dmppm-m2CP) ₂ (dpm)] was obtained in this example.

¹ H-NMR. δ (CDCl ₃ ): 0.92 (s, 18 H), 1.53 (s, 6 H). 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, 2 H), 7. 70 (d, 2 H), 7. 85 (s, 2 H), 8. 97 (s, 2 H).

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

The measurement results of the obtained absorption spectrum and emission spectrum are shown in FIG. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. The thin solid line in FIG. 21 indicates the absorption spectrum, and the thick solid line indicates the emission spectrum. In addition, the absorption spectrum shown in FIG. 21 shows the result which deducted the absorption spectrum which put only dichloromethane into the quartz cell and measured it from the absorption spectrum which put the dichloromethane solution (0.010 mmol / L) into the quartz cell and measured.

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

«Synthesis example 4»
In this example, an organometallic complex which is one embodiment of the present invention represented by a structural formula (117) of Embodiment 1, bis {4,6-dimethyl-2- [6- (2,6-dicyanophenyl ) -4-Pyrimidinyl-κN ³ ] phenyl-κC} (2,2,6,6-tetramethyl-3,5-heptanedionato-κO, O ′) iridium (III) (abbreviation: [Ir (dmppm-dCP)] _A method of synthesizing ₂ (dpm)] will be described. The structure of [Ir (dmppm-dCP) ₂ (dpm)] is shown below.

In addition, a synthesis method of [Ir (dmppm-dCP) ₂ (dpm)] is shown in a synthesis scheme of the following formula (d-1) to the following formula (d-4).

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), 10R, 210G: conductive layer, 301: first substrate, 302: pixel portion, 303: drive circuit portion (source line drive circuit), 304a, 304b: drive circuit portion (gate line drive circuit), 305: seal material, 306: second substrate, 307: lead wiring, 308: FPC, 309: FET, 310: FET, 311: FET, 312: FET, 313: first electrode, 314: insulator, 315: EL layer, 316 A second electrode, 317: a light emitting element, 318: space, 900: a substrate, 901: a first electrode, 902: an EL layer, 903: a second electrode, 911: a hole injection layer, 912: a 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 400 : 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: flattening film, 4215: diffusion plate, 5101: light, 5102: wheel, 5103: door, 5104: display portion, 5105: handle, 5106 : Shift lever, 5107: Seat, 5108: Inner rear view mirror, 7000: Housing, 7001: Table Display portion 7002: second display portion 7003: speaker 7004: LED lamp 7005: operation key 7006: connection terminal 7007: sensor 7008: microphone 7009: switch 7010: infrared port 7011: recording medium Reading unit 7012: Support unit 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 indicating time, 7028: Other icon, 7029: Sensor, 7030: Speaker, 7052, 7053, 7054: Information, 9310: Personal Digital Assistant, 9311: Display Department 9 12: display area, 9313: Hinge, 9315: casing,

Claims

An organometallic complex represented by General Formula (G1).

(In the 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 which forms a ring, the number of carbon atoms carbon atoms in a ring to form a 6 substituted or unsubstituted aryl group having to 13 or ring, represents one of a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. also, R 5 - R 9 independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming the ring, or a substituent having 3 to 12 carbon atoms forming the ring Or at least one represents a cyano group, and L represents a monoanionic ligand, and n is 1 to 3. Represents an integer)
An organometallic complex represented by General Formula (G1).

(In the 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 which forms a ring, the number of carbon atoms carbon atoms in a ring to form a 6 substituted or unsubstituted aryl group having to 13 or ring, represents one of a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. also, R 5 - R 9 independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming the ring, or a substituent having 3 to 12 carbon atoms forming the ring Or a substituted heteroaryl group or a cyano group, and any one of R 6 to R 8 represents a cyano group, and L represents a monoanionic ligand. And n represents an integer of 1 to 3.)
In claim 1 or claim 2,
The organometallic complex wherein n is 2.
In any one of claims 1 to 3,
The monoanionic ligand is a monoanionic bidentate chelate ligand having a β-diketone structure, a monoanionic bidentate chelate ligand having a carboxyl group, a monoanionic property having a phenolic hydroxyl group , A monoanionic bidentate chelate ligand in which both coordination elements are nitrogen, or an aromatic heterocyclic bidentate which forms a metal-carbon bond with iridium by cyclometalation An organometallic complex which is any one of ligands.
In any one of claims 1 to 3,
An organometallic complex in which the monoanionic ligand is any one of the following general formulas (L1) to (L8).

(Wherein, R 71 to R 77 and R 87 to R 131 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 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 A substituted or unsubstituted aryl group having 6 to 13 carbon atoms which forms a ring, or A 1 to A 3 are sp 2 hybrid carbons independently bonded to nitrogen or hydrogen, or sp having a substituent. 2 represents a mixed carbon, and the substituent represents 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.)
In claim 1 or claim 2,
The organometallic complex in which n is 3.
An organometallic complex represented by General Formula (G2).

(In the 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, R 5 to R represent a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming the ring, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms forming the ring. 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 the ring, a substitution or 3 to 12 carbon atoms forming the ring R 71 and R 73 each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, or a ring, each of which represents a cyano group. Or substituted carbon atoms having 5 to 7 carbon atoms Aroalkyl group, 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 a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming the ring)
An organometallic complex represented by General Formula (G2).

(In the 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, the number of carbon atoms carbon atoms in a ring to form a 6 substituted or unsubstituted aryl group having to 13 or ring, represents one of a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. also, R 5 - R 9 independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming the ring, or a substituent having 3 to 12 carbon atoms forming the ring Or a substituted or unsubstituted heteroaryl group or a cyano group, and any one of R 6 to R 8 represents a cyano group, and R 71 and R 73 each independently represent hydrogen or carbon; The alkyl group of the number 1-6, the carbon number which forms a ring is 5 To 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 group Or an alkylthio group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms which forms a ring).
An organometallic complex represented by the following structural formula (100).
A light emitting device using the organometallic complex according to any one of claims 1 to 9.
Has an EL layer between a pair of electrodes,
A light emitting device comprising the organometallic complex according to any one of claims 1 to 9, wherein the EL layer.
Has an EL layer between a pair of electrodes,
The EL layer has a light emitting layer,
A light emitting device comprising the organometallic complex according to any one of claims 1 to 9, wherein the light emitting layer.
Has an EL layer between a pair of electrodes,
The EL layer has a light emitting layer,
The light emitting layer comprises a plurality of organic compounds,
A light emitting device in which one of the plurality of organic compounds is the organometallic complex according to any one of claims 1 to 9.
A light emitting element according to any one of claims 10 to 13;
A transistor, or a substrate,
A light emitting device having
A light emitting device according to claim 14;
Microphone, camera, operation button, external connection unit, or speaker
Electronic equipment having.
A light emitting device according to claim 14;
A housing, a cover, or a support,
A lighting device having