JP6537877B2 - Organometallic complex, light emitting element, light emitting device, electronic device and lighting device - Google Patents

Description

  One embodiment of the present invention relates to an organometallic complex, a light-emitting element using the organometallic complex, a display module, a lighting module, a display device, a light-emitting device, an electronic device, and a lighting device. Note that one embodiment of the present invention is not limited to the above technical field. The technical field of one embodiment of the invention disclosed in the present specification and the like relates to an object, a method, or a method of manufacturing. Alternatively, one aspect of the present invention relates to a process, a machine, a manufacture, or a composition (composition of matter). Therefore, the technical field of one embodiment of the present invention disclosed in the present specification more specifically includes a semiconductor device, a display device, a liquid crystal display device, a light emitting device, a lighting device, a power storage device, a storage device, and a driving method thereof. Or their production methods can be mentioned as an example.

  A display using a light emitting element (organic EL element) using an organic compound or an organic metal complex as a light emitting material as a lighting device or a display device of the next generation from the potential of thin and light weight, high speed response to input signals, and low power consumption. Devices have been developed and announced.

  In the organic EL element, by applying a voltage across the light emitting layer between the electrodes, electrons and holes injected from the electrode recombine, the light emitting substance becomes an excited state, and light is emitted when the excited state returns to the ground state Do. The spectrum of light emitted from a light-emitting substance is specific to the light-emitting substance, and by using different kinds of light-emitting substances, light-emitting elements that emit light of various colors can be obtained.

  As described above, displays and lighting devices using light emitting elements are suitably applied to various electronic devices, but there is still room for improvement in their performance and cost competitiveness. Therefore, materials having better properties and handling are being sought every day.

Patent Document 1 presents an organometallic complex having a ligand containing a pyrazine skeleton and a dibenzofuran skeleton or a dibenzothiophene skeleton.

WO 2004/111066 pamphlet

An aspect of the present invention is to provide a novel organometallic complex. Alternatively, it is an object of the present invention to provide a highly heat-resistant organometallic complex. Another object is to provide an organometallic complex which emits light efficiently. Alternatively, it is an object of the present invention to provide an organometallic complex which emits light with good color purity. Another object of the present invention is to provide a light emitting element with high light emission efficiency. Alternatively, it is an object of the present invention to provide a light-emitting element that emits light with good color purity. Alternatively, it is an object of the present invention to provide a light emitting device having good color reproducibility. Another object is to provide a light emitting device with good energy efficiency.

  Alternatively, another object of the present invention is to provide a new light emitting element. Alternatively, another object is to provide a display module with low power consumption, a lighting module, a light-emitting device, a display device, an electronic device, and a lighting device.

  One aspect of the present invention should solve any one of the above-described problems. Note that the descriptions of these objects do not disturb the existence of other objects. Note that one embodiment of the present invention does not necessarily have to have all of these objects. In addition, problems other than these are naturally apparent from the description of the specification, drawings, claims and the like, and it is possible to extract the problems other than these from the description of the specification, drawings, claims and the like. It is.

In one embodiment of the present invention, an organometallic in which a nitrogen at position 3 of a pyrimidine ring is coordinated to a metal, a dibenzothiophene skeleton or a dibenzofuran skeleton is provided at position 4 of the pyrimidine ring, and a dibenzothiophene skeleton or a dibenzofuran skeleton is bonded to a metal A light emitting element having a complex as a light emitting center.

Another embodiment of the present invention is a light-emitting element having the above structure, wherein the metal is a group 9 element or a group 10 element.

Another embodiment of the present invention is a light-emitting element having the above structure, in which the metal is iridium.

Alternatively, another structure of the present invention is an organometallic complex having a structure represented by the following general formula (G0-1).

In the formula, R ¹ represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. R ^{2 to} R ^{9 each} represent hydrogen or an alkyl group having 1 to 6 carbon atoms. M represents a metal of a Group 9 element or a Group 10 element. Also, X represents an oxygen atom or a sulfur atom.

Another embodiment of the present invention is an organometallic complex represented by General Formula (G0-2).

In the formula, R ¹ represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. R ^{2 to} R ^{9 each} represent hydrogen or an alkyl group having 1 to 6 carbon atoms. M represents a metal of a Group 9 element or a Group 10 element. In addition, n is 3 when M is a Group 9 element and is 2 when M is a Group 10 element. Also, X represents an oxygen atom or a sulfur atom.

Another embodiment of the present invention is an organometallic complex represented by General Formula (G0-3).

In the formula, R ¹ represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. R ^{2 to} R ^{9 each} represent hydrogen or an alkyl group having 1 to 6 carbon atoms. M represents a metal of a Group 9 element or a Group 10 element, m is 2 when M is a Group 9 element, and 1 when M is a Group 10 element. L represents a monoanionic ligand. Also, X represents an oxygen atom or a sulfur atom.

Another structure of the present invention is that, in the above structure, the monoanionic ligand is a monoanionic bidentate chelate ligand having a beta diketone structure, or a monoanionic bidentate chelate coordination having a carboxyl group. A monoanionic bidentate chelate ligand having a phenolic hydroxyl group, a monoanionic bidentate chelate ligand in which both coordination elements are nitrogen, or a carbon atom forming a metal-carbon bond Is an organometallic complex which is a monoanionic ligand containing a coordinated N atom to form a 5- or 6-membered metallacycle.

Another structure of the present invention is an organometallic complex having the above structure in which the monoanionic ligand is any one of formulas (L1) to (L7).

In the formula, R ^{71 to} R ¹⁰⁹ each independently represent hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a halogen group, a vinyl group, a substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, It represents a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms. A ^{1 to} A ³ each independently represent nitrogen, an sp ² hybridized carbon bonded to hydrogen, or an sp ² carbon bonded to a substituent R, and the substituent R is an alkyl group having 1 to 6 carbon atoms And a halogen group, a haloalkyl group having 1 to 6 carbon atoms, or a phenyl group.

Another structure of the present invention is an organometallic complex represented by General Formula (G1-1).

In the formula, R ¹ represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. R ^{2 to} R ^{9 each} represent hydrogen or an alkyl group having 1 to 6 carbon atoms. Also, X represents an oxygen atom or a sulfur atom.

Another structure of the present invention is an organometallic complex represented by General Formula (G1-2).

In the formula, R ¹ represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. R ^{2 to} R ^{9 each} represent hydrogen or an alkyl group having 1 to 6 carbon atoms. Also, X represents an oxygen atom or a sulfur atom.

Another structure of the present invention is an organometallic complex in the above structure, wherein R ¹ is either an alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted phenyl group.

Another structure of the present invention is an organometallic complex in the above structure, wherein R ¹ is any of a C 4 to C 6 alkyl group.

Another structure of the present invention is an organometallic complex in which X is a sulfur atom in the above structure.

Another structure of the present invention is an organometallic complex in which X is an oxygen atom in the above structure.

Another structure of the present invention is a light emitting element using the organometallic complex having the above structure.

Another structure of the present invention is a light emitting device using the light emitting element having the above structure.

Another structure of the present invention is an electronic device using the light emitting device having the above structure.

Another configuration of the present invention is a lighting device using the light emitting device having the above configuration.

The light emitting device in the present specification includes an image display device using a light emitting element. In addition, a module in which a connector such as an anisotropic conductive film or TCP (Tape Carrier Package) is attached to a light emitting element, a module in which a printed wiring board is provided ahead of TCP, or a COG (Chip On Glass) method for a light emitting element A module on which an IC (integrated circuit) is directly mounted may have a light emitting device. Furthermore, the luminaire may have a light emitting device.

The organometallic complex of one embodiment of the present invention is a novel organometallic complex. Alternatively, it is an organic metal complex having high heat resistance. Alternatively, it is an organometallic complex which emits light efficiently. Alternatively, it is an organometallic complex which emits light with good color purity. Alternatively, a light-emitting element with high light emission efficiency can be provided. Alternatively, a light-emitting element can be provided which exhibits light emission with good color purity. Alternatively, a light-emitting device with favorable color reproducibility can be provided. Alternatively, a light-emitting device with high energy efficiency can be provided.

  Alternatively, another aspect of the present invention can provide a novel light emitting element. Alternatively, a display module with low power consumption, a lighting module, a light-emitting device, a display device, an electronic device, and a lighting device can be provided.

  One aspect of the present invention may be any one of the above-described effects. 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.

FIG. FIG. 2 is a conceptual diagram of an active matrix light-emitting device. FIG. 2 is a conceptual diagram of an active matrix light-emitting device. FIG. 2 is a conceptual diagram of an active matrix light-emitting device. FIG. 1 is a conceptual diagram of a passive matrix light-emitting device. FIG. FIG. FIG. FIG. FIG. FIG. 6 is a diagram illustrating an in-vehicle display device and a lighting device. FIG. NMR chart of [Ir (iBudbfpm) ₂ (acac)]. Absorption spectrum and emission spectrum of [Ir (iBudbfpm) ₂ (acac)]. MS spectrum of [Ir (iBudbfpm) ₂ (acac)]. NMR chart of [Ir (iBudbtpm) ₃ ]. Absorption spectrum and emission spectrum of [Ir (iBudbtpm) ₃ ]. MS spectrum of [Ir (iBudbtpm) ₃ ]. NMR chart of [Ir (iBudbfpm) ₃ ]. Absorption spectrum and emission spectrum of [Ir (iBudbfpm) ₃ ]. MS spectrum of [Ir (iBudbfpm) ₃ ]. Brightness-current efficiency characteristics of the light-emitting element 1 Voltage-luminance characteristics of the light-emitting element 1 Voltage-current characteristics of the light-emitting element 1 11 shows an emission spectrum of the light-emitting element 1. The luminance-current efficiency characteristic of the light emitting element 2 and the light emitting element 3 Voltage-luminance characteristics of the light-emitting element 2 and the light-emitting element 3 Voltage-current characteristics of the light-emitting element 2 and the light-emitting element 3 Emission spectra of the light-emitting element 2 and the light-emitting element 3

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 it can be easily understood by those skilled in the art that various changes can be made in the form and details without departing from the spirit and the scope of the present invention. Therefore, the present invention should not be construed as being limited to the description of the embodiments below.

In one embodiment of the present invention, the nitrogen at position 3 of the pyrimidine ring is coordinated to a metal, the carbon at position 4 of the pyrimidine ring is substituted with a dibenzothiophene skeleton or a dibenzofuran skeleton, and the dibenzothiophene skeleton or a dibenzofuran skeleton is bonded to a metal It is an organometallic complex.

This organometallic complex exhibits green light emission with good color purity and has high efficiency, and thus can be suitably used as a light-emitting substance of a light-emitting element. Note that although the organometallic complex of one embodiment of the present invention has a pyrimidine ring, a light-emitting element using the organometallic complex as a light emission center and a similar organometallic complex in which the pyrimidine ring is a pyridine ring As compared with the light-emitting element used, a light-emitting element using the organometallic complex of one embodiment of the present invention can be a light-emitting element that emits light more efficiently.

  The metal constituting the organometallic complex is preferably a metal belonging to Group 9 or 10 because light emission can be obtained with good efficiency.

In addition, the dibenzothiophene skeleton or the dibenzofuran skeleton in the organometallic complex is preferably bonded to the pyrimidine skeleton at the 2-position because good green emission can be obtained while maintaining the light emission efficiency.

Such an organometallic complex can also be referred to as an organometallic complex having a structure represented by the following general formula (G0-1).

In the formula, R ¹ represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. R ^{2 to} R ⁹ each independently represent hydrogen or an alkyl group having 1 to 6 carbon atoms. M represents a metal of a Group 9 element or a Group 10 element. Also, X represents an oxygen atom or a sulfur atom.

Specific examples of the alkyl group having 1 to 6 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, 1-methylbutyl group, 2-methylbutyl group, 3-methylbutyl group, 1-ethylpropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 2,2-dimethylpropyl group, branched or The hexyl group etc. which do not have are mention | raise | lifted. When the said phenyl group has a substituent, a C1-C4 alkyl group can be mentioned as the said substituent, for example. Specifically, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group and the like can be mentioned.

The organometallic complex of one embodiment of the present invention has a configuration in which only a ligand in which a dibenzothiophene skeleton or a dibenzofuran skeleton is bonded to the 4-position of a pyrimidine ring binds and coordinates to a central metal, and a configuration different from the ligand There is a configuration in which the bond bonds to and coordinates with one central metal.

An organometallic complex in which only a ligand in which a dibenzothiophene skeleton or a dibenzofuran skeleton is bonded to the 4-position of a pyrimidine ring bonds to a central metal and coordinates can be represented by the following general formula (G0-2).

In the formula, R ^{1 to} R ⁹ , M, and X are the same as those described for (G0-1). n is 3 when M is a Group 9 element and is 2 when M is a Group 10 element.

An organometallic complex in which a ligand different from the ligand is bonded to and coordinated with one central metal can be represented by the following general formula (G0-3).

In the formulae, since R ^{1 to} R ⁹ , M and X are the same as those described in (G0-1), duplicate descriptions will be omitted. m is 2 when M is a Group 9 element and 1 when M is a Group 10 element. L represents a monoanionic ligand.

Examples of the monoanionic ligand include a monoanionic bidentate chelating ligand having a beta diketone structure, a monoanionic bidentate chelating ligand having a carboxyl group, and a monoanionic dibasic having a phenolic hydroxyl group. 5- or 6-membered containing a N-chelate ligand, a monoanionic bidentate chelate ligand in which both coordination elements are nitrogen, and a carbon atom forming a metal-carbon bond A monoanionic ligand or the like that forms a metallacycle can be used.

The monoanionic ligand is preferably any one of the following general formulas (L1) to (L7).

In the formula, each of R ^{71 to} R ¹⁰⁹ independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted halogen group having 1 to 6 carbon atoms, a substituted or unsubstituted carbon Number 1 to 6 vinyl group, substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms Represents A ^{1 to} A ³ each independently represent either nitrogen, sp ² -hybridized carbon bonded to hydrogen, or sp ² carbon bonded to substituent R, and the substituent R has 1 to 6 carbon atoms Or an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, or a phenyl group.

In the organometallic complex of one embodiment of the present invention, M is preferably an element of Group 9, and iridium is particularly preferable. Moreover, as a monoanionic ligand, the ligand represented by the said General formula (L1) is preferable. That is, the organometallic complex of one embodiment of the present invention is an organometallic complex represented by the following general formula (G1-1).

In the formulae, since R ^{1 to} R ⁹ , M and X are the same as those described in (G0-1), duplicate descriptions will be omitted.

Another structure of the present invention is an organometallic complex represented by General Formula (G1-2).

In the formulae, since R ^{1 to} R ⁹ , M and X are the same as those described in (G0-1), duplicate descriptions will be omitted.

In these organometallic complexes, R ¹ is preferably one of an alkyl group having 1 to 6 carbon atoms and a phenyl group. In particular, a configuration in which the alkyl group has 4 to 6 carbon atoms is preferable because the solubility is high and synthesis and purification are easily performed.

In the above structure, an organometallic complex in which X is a sulfur atom is preferable because the heat resistance is improved.

In the above structure, an organic metal complex in which X is an oxygen atom is preferable because heat resistance is improved and more favorable green light emission can be obtained.

Some of the specific examples of the organometallic complex of one embodiment of the present invention having the above-described structure are described below.

  Various reactions can be applied as a method of synthesizing the organometallic complex of one embodiment of the present invention as described above.

<< Synthesis Method of Pyrimidine Derivative Represented by General Formula (G0) >>
First, a synthesis method of a pyrimidine derivative which is a ligand of an organometallic complex according to one aspect of this embodiment is described. The pyrimidine derivative is represented by the following general formula (G0).

In General Formula (G0), R ¹ represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. R ^{2 to} R ⁹ each independently represent hydrogen or an alkyl group having 1 to 6 carbon atoms.

The pyrimidine derivative represented by the above general formula (G0) is, for example, as shown in the following scheme (A), a boronic acid or a boronate ester or a cyclic triol borate salt (A1) and a halogenated pyrimidine compound (A2) It is obtained by coupling. The cyclic triol borate salt may use potassium salt or sodium salt in addition to lithium salt.

In the above synthesis scheme (A), Q represents a halogen, and B ¹ represents a boronic acid or a boronic ester, a cyclic triol borate salt or the like.

Further, as shown in the following scheme (A ′), the pyrimidine derivative represented by the above general formula (G0) can also be produced by reacting an aryl 1,3-diketone (A1 ′) with an amidine (A2 ′). can get.

Since various types of the compounds (A1), (A2), (A1 ′) and (A2 ′) described above are commercially available or can be synthesized, the pyrimidine derivative represented by the general formula (G0) is Many types can be synthesized. Therefore, the organometallic complex which is one embodiment of the present invention is characterized in being rich in variations of the ligand.

<< Synthesis Method of Organometallic Complex Represented by General Formula (G0-2) >>
As shown in the following synthesis scheme (B), the organometallic complex represented by the general formula (G0-2) is a pyrimidine derivative represented by the general formula (G0), and a group 9 or 10 containing a halogen Metal compounds (rhodium chloride hydrate, palladium chloride, iridium chloride hydrate, ammonium hexachloroiridate, potassium tetrachloroplatinate etc.), or group 9 or 10 organometallic complex compounds (acetylacetonato complexes) After mixing with diethyl sulfide complex etc.) and heating. In addition, this heating process is carried out by using a pyrimidine derivative represented by the general formula (G0), a metal compound of Group 9 or 10 containing a halogen, or an organometallic complex compound of Group 9 or 10 It may be carried out after being dissolved in a system solvent (glycerol, ethylene glycol, 2-methoxyethanol, 2-ethoxyethanol or the like). In the scheme (B), M represents a group 9 element or a group 10 element. When M is a group 9 element, n = 3, and when M is a group 10 element, n = 2.

In the synthesis scheme (B), R ¹ represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. R ^{2 to} R ⁹ each independently represent hydrogen or an alkyl group having 1 to 6 carbon atoms. M represents a metal of a Group 9 element or a Group 10 element. In addition, n is 3 when M is a Group 9 element and is 2 when M is a Group 10 element. Also, X represents an oxygen atom or a sulfur atom.

In the present invention, in order to obtain an ortho metal complex having a pyrimidine derivative as a ligand, it is preferable to introduce a substituent at the 6-position of pyrimidine (that is, R ¹ ). In particular, it is preferable to use either an alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted phenyl group as R ¹ . Thus, the organometallic complex substituent is introduced into R ¹ may be compared with the organometallic complex R ¹ is hydrogen, increase the yield in the synthesis scheme (B).

<< Synthesis Method of Organometallic Complex Represented by General Formula (G0-3) >>
First, as shown in the following synthesis scheme (C-1), a pyrimidine derivative represented by the general formula (G0) and a metal compound containing halogen (palladium chloride, iridium chloride, iridium bromide, iridium iodide, tetrachloro Using potassium platinate and the like as a solvent-free or alcoholic solvent (glycerol, ethylene glycol, 2-methoxyethanol, 2-ethoxyethanol etc.) alone or a mixed solvent of one or more alcoholic solvents and water, By heating in an inert gas atmosphere, a dinuclear complex (P) which is a kind of an organometallic complex having a halogen-bridged structure 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 synthesis scheme (C-1), Q represents a halogen, and R ¹ represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. R ^{2 to} R ⁹ each independently represent hydrogen or an alkyl group having 1 to 6 carbon atoms. M represents a metal of a Group 9 element or a Group 10 element, m is 2 when M is a Group 9 element, and 1 when M is a Group 10 element. L represents a monoanionic ligand. Also, X represents an oxygen atom or a sulfur atom.

Furthermore, as shown in the following synthesis scheme (C-2), the binuclear complex (P) obtained in the above synthesis scheme (C-1) and the raw material HL of the monoanionic ligand, an inert gas By reacting in an atmosphere, the proton of HL is eliminated and L is coordinated to the central metal M to obtain an organometallic complex which is an embodiment of the present invention represented by General Formula (G0-3). 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 synthesis scheme (C-2), L represents a monoanionic ligand, Q represents a halogen, R ¹ represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group Represents R ^{2 to} R ⁹ each independently represent hydrogen or an alkyl group having 1 to 6 carbon atoms. M represents a metal of a Group 9 element or a Group 10 element, m is 2 when M is a Group 9 element, and 1 when M is a Group 10 element. L represents a monoanionic ligand. Also, X represents an oxygen atom or a sulfur atom.

In the present invention, in order to obtain an ortho metal complex having a pyrimidine derivative as a ligand, it is preferable to introduce a substituent at the 6-position of pyrimidine (that is, R ¹ ). In particular, it is preferable to use either an alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted phenyl group as R ¹ . Thereby, the dinuclear metal complex bridged with halogen generated in the synthesis scheme (C-1) is decomposed during the reaction represented by the synthesis scheme (C-2) as compared to the case where hydrogen is used as R ¹ Can be suppressed, and a very high yield can be obtained. As a result, the organometallic complex can be obtained inexpensively.

In addition, the monoanionic ligand L in general formula (G0-3) is a monoanionic bidentate chelate ligand having a beta diketone structure, and a monoanionic bidentate chelate coordination having a carboxyl group. Preferably, it is a monoanionic bidentate chelating ligand having a phenolic hydroxyl group, or a monoanionic bidentate chelating ligand in which the two coordination elements are both nitrogen. In particular, when it is a monoanionic bidentate chelating ligand having a beta diketone structure, the solubility of the organometallic complex in an organic solvent is enhanced by having the beta diketone structure, which facilitates purification, which is preferable. In addition, by having a beta diketone structure, an organometallic complex having high emission efficiency can be obtained, which is preferable. Moreover, by having a beta diketone structure, there exists an advantage that sublimation property increases and it is excellent in vapor deposition performance.

The monoanionic ligand is preferably any one of formulas (L1) to (L7). These ligands are effective because they have high coordination ability and can be obtained inexpensively.

In the formula, each of R ^{71 to} R ¹⁰⁹ independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted halogen group having 1 to 6 carbon atoms, a substituted or unsubstituted carbon Number 1 to 6 vinyl group, substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms Represents A ^{1 to} A ³ each independently represent either nitrogen, sp ² -hybridized carbon bonded to hydrogen, or sp ² carbon bonded to substituent R, and the substituent R has 1 to 6 carbon atoms Or an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, or a phenyl group.

«Light-emitting element»
Then, an example of a light-emitting element which is one embodiment of the present invention will be described in detail below with reference to FIG.

  The light-emitting element in this embodiment includes a pair of electrodes including a first electrode 101 and a second electrode 102, and an EL layer 103 provided between the first electrode 101 and the second electrode 102. And consists of Note that the first electrode 101 functions as an anode and the second electrode 102 functions as a cathode in the following description.

  In order to function as the anode, the first electrode 101 is preferably formed using a metal having a high work function (specifically, 4.0 eV or more), an alloy, a conductive compound, a mixture thereof, or the like. Specifically, for example, indium oxide-tin oxide (ITO: Indium Tin Oxide), silicon or indium oxide-tin oxide containing silicon oxide, indium oxide-zinc oxide, tungsten oxide and indium oxide containing zinc oxide ( Such as IWZO). These conductive metal oxide films are generally formed by sputtering, but may be formed by applying sol-gel method or the like. As an example of a manufacturing method, there is a method in which indium oxide-zinc oxide is formed by a sputtering method using a target obtained by adding 1 to 20 wt% of zinc oxide to indium oxide. In addition, indium oxide containing tungsten oxide and zinc oxide (IWZO) is formed by sputtering using a target containing 0.5 to 5 wt% of tungsten oxide and 0.1 to 1 wt% of zinc oxide with respect to indium oxide You can also Besides, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium Pd) or nitrides of metal materials (eg, titanium nitride) and the like can be mentioned. Graphene can also be used. Note that by using a composite material described later for the layer in contact with the first electrode 101 in the EL layer 103, an electrode material can be selected regardless of the work function.

  The EL layer 103 preferably has a layered structure, and any layer of the layered structure preferably includes the organometallic complex of one embodiment of the present invention. The organometallic complex is preferably an organometallic complex represented by any one of the general formulas (G0-1) to (G0-3). In addition, the organometallic complex is more preferably an organometallic complex represented by General Formula (G1-1) or (G1-2).

The layered structure of the EL layer 103 can be formed by appropriately combining a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, a carrier blocking layer, an intermediate layer, and the like. In this embodiment mode, the EL layer 103 includes the hole injecting layer 111, the hole transporting layer 112, the light emitting layer 113, the electron transporting layer 114, and the electron injecting layer 115 sequentially stacked on the first electrode 101. Will be explained. Specific examples of materials constituting each layer are specifically shown below.

The hole injection layer 111 is a layer containing a substance having a high hole injection property. Molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide, or the like can be used. Other than these, phthalocyanine-based compounds such as phthalocyanine (abbreviation: H ₂ Pc) and copper phthalocyanine (CuPC); 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: The hole injection layer 111 may also be formed of an aromatic amine compound such as DNTPD) or a polymer such as poly (3,4-ethylenedioxythiophene) / poly (styrene sulfonic acid) (PEDOT / PSS). it can.

In addition, as the hole injecting layer 111, a composite material in which a substance having a hole transporting property contains an acceptor substance can be used. Note that by using a substance having a hole transporting property containing an acceptor substance, a material for forming an electrode can be selected regardless of the work function of the electrode. That is, not only a material with a large work function but also a material with a small work function can be used as the first electrode 101. Examples of the acceptor substance include 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F ₄ -TCNQ), chloranil, and the like. Also, transition metal oxides can be mentioned. 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 and rhenium oxide are preferable because they have high electron accepting properties. Among them, molybdenum oxide is particularly preferable because it is stable in the air, has low hygroscopicity, and is easy to handle.

As the hole transporting substance used for the composite material, various organic compounds such as an aromatic amine compound, a carbazole derivative, an aromatic hydrocarbon, a polymer compound (oligomer, dendrimer, polymer, etc.) can be used. In addition, as an organic compound used for a composite material, it is preferable that it is an organic compound with high hole transportability. Specifically, a substance having a hole mobility of 10 ⁻⁶ cm ² / Vs or more is preferable. Hereinafter, organic compounds which can be used as the hole transporting substance in the composite material are specifically listed.

  For example, as an aromatic amine compound which can be used for the composite material, N, N'-di (p-tolyl) -N, N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'- Bis [N- (4-diphenylaminophenyl) -N-phenylamino] biphenyl (abbreviation: DPAB), N, N′-bis {4- [bis (3-methylphenyl) amino] phenyl} -N, N ′ -Diphenyl- (1,1'-biphenyl) -4,4'-diamine (abbreviation: DNTPD), 1,3,5-tris [N- (4-diphenylaminophenyl) -N-phenylamino] benzene (abbreviation : DPA3B) etc. can be mentioned. Specific examples of the carbazole derivative include 3- [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA2), 3- [N- (1-naphthyl) -N- (9-phenylcarbazol-3-yl) Amino] -9-phenylcarbazole (abbreviation: PCzPCN1), 4,4′-di (N-carbazolyl) biphenyl (abbreviation: CBP), 1,3,5-tris [4- (N-carbazolyl) phenyl] benzene (benzene) Abbreviation: TCPB), 9- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole (abbreviation: CzPA), 1,4- Scan [4-(N-carbazolyl) phenyl] -2,3,5,6-tetraphenylbenzene, or the like can be used. As an aromatic hydrocarbon, for example, 2-tert-butyl-9,10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA), 2-tert-butyl-9,10-di (1-naphthyl) Anthracene, 9,10-bis (3,5-diphenylphenyl) anthracene (abbreviation: DPPA), 2-tert-butyl-9,10-bis (4-phenylphenyl) anthracene (abbreviation: t-BuDBA), 9, 10-di (2-naphthyl) anthracene (abbreviation: DNA), 9,10-diphenylanthracene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation: t-BuAnth), 9,10-bis (4-methyl) -1-Naphthyl) anthracene (abbreviation: DMNA), 2-tert-butyl-9,10-bis [2- (1-naphthyl) phenyl Nyl] anthracene, 9,10-bis [2- (1-naphthyl) phenyl] anthracene, 2,3,6,7-tetramethyl-9,10-di (1-naphthyl) anthracene, 2,3,6, 7-Tetramethyl-9,10-di (2-naphthyl) anthracene, 9,9'-bianthryl, 10,10'-diphenyl-9,9'-bianthryl, 10,10'-bis (2-phenylphenyl) -9,9'-bianthryl, 10,10'-bis [(2,3,4,5,6-pentaphenyl) phenyl] -9,9'-bianthryl, anthracene, tetracene, rubrene, perylene, 2,5 , 8, 11-tetra (tert-butyl) perylene and the like. Besides these, pentacene, coronene and the like can also be used. It may have a vinyl skeleton. Examples of the aromatic hydrocarbon having a vinyl group include 4,4′-bis (2,2-diphenylvinyl) biphenyl (abbreviation: DPVBi), 9,10-bis [4- (2,2- And diphenylvinyl) phenyl] anthracene (abbreviation: DPVPA) and the like.

  In addition, poly (N-vinylcarbazole) (abbreviation: PVK) or 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.

  By forming the hole injecting layer, the hole injecting property is improved, and a light emitting element with a small driving voltage can be obtained.

The hole transporting layer 112 is a layer containing a hole transporting substance. As the hole transporting substance, for example, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB) or N, N′-bis (3-methylphenyl) -N, N'-diphenyl- [1,1'-biphenyl] -4,4'-diamine (abbreviation: TPD), 4,4 ', 4''-tris (N, N-diphenylamino) triphenylamine (Abbreviation: TDATA), 4,4 ′, 4 ′ ′-tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine (abbreviation: MTDATA), 4,4′-bis [N- (4) Spiro-9,9′-bifluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: BSPB), 4-phenyl-4 ′-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: BPAFLP) Aromatic amine compounds such as Or the like can be used. The substance described here is a substance having a high hole transportability and mainly having a hole mobility of 10 ⁻⁶ cm ² / Vs or more. Further, the organic compounds mentioned as the hole transporting substance in the above-described composite material can also be used for the hole transporting layer 112. Alternatively, high molecular compounds such as poly (N-vinylcarbazole) (abbreviation: PVK) and poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used. Note that the layer containing a hole transporting substance is not limited to a single layer, and two or more layers containing the above substances may be stacked.

  The light emitting layer 113 may be a layer exhibiting fluorescence, a layer exhibiting phosphorescence, or a layer exhibiting thermally activated delayed fluorescence (TADF). In addition, it may be a single layer or a plurality of layers containing different light emitting substances. In the case of forming a light emitting layer including a plurality of layers, a layer containing a phosphorescent material and a layer containing a fluorescent material may be stacked. Under the present circumstances, it is preferable to utilize the below-mentioned exciplex in the layer in which a phosphorescence-emitting substance is contained.

As the fluorescent substance, for example, the following substances can be used. In addition, other fluorescent substances can also be used. 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- (9-phenyl-9H-fluoren-9-yl) phenyl] -N, N'-diphenyl Pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), 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'-bis [4- (9H-carbazol-9-yl) phenyl] -N, N'-diphenylstilbene-4 4'-diamine (abbreviation: YGA2S), 4- (9H-carbazol-9-yl) -4 '-(10-phenyl-9-anthryl) triphenylamine (abbreviation: YGAPA), 4- (9H-carbazole-) 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), perylene, 2,5,8,11-tetra-tert-butylperylene (abbreviation: TBP), 4- (10-phenyl-9-anthryl) -4 ' -(9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBAPA), N, N ''-(2-tert-butyl anthra) -9,10-Diyldi-4,1-phenylene) bis [N, N ', N'-triphenyl-1,4-phenylenediamine] (abbreviation: DPABPA), N, 9-diphenyl-N- [4 -(9,10-Diphenyl-2-anthryl) phenyl] -9H-carbazol-3-amine (abbreviation: 2PCAPPA), N- [4- (9,10-diphenyl-2-anthryl) phenyl] -N, N ', N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA), N, N, N', N ', N' ', N' ', N' ', N' '', N '' '-octaphenyl Dibenzo [g, p] chrysene-2,7,10,15-tetraamine (abbreviation: DBC1), coumarin 30, N- (9,10-diphenyl-2-anthryl) -N, 9-diphenyl-9H-carbazole- 3 -Amine (abbreviation: 2PCAPA), N- [9,10-bis (1,1'-biphenyl-2-yl) -2-anthryl] -N, 9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N- (9,10-diphenyl-2-anthryl) -N, N ', N'-triphenyl-1,4-phenylenediamine (abbreviation: 2D PAPA), N- [9,10-bis (1) , 1′-biphenyl-2-yl) -2-anthryl] -N, N ′, N′-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), 9,10-bis (1,1′-) Biphenyl-2-yl) -N- [4- (9H-carbazol-9-yl) phenyl] -N-phenylanthracene-2-amine (abbreviation: 2YGABPhA), N, N, 9-triphenylant Sen-9-amine (abbreviation: DPhAPhA) coumarin 545T, N, N'-diphenylquinacridone, (abbreviation: DPQd), rubrene, 5,12-bis (1,1'-biphenyl-4-yl) -6,11 -Diphenyltetracene (abbreviation: BPT), 2- (2- {2- [4- (dimethylamino) phenyl] ethenyl} -6-methyl-4H-pyran-4-ylidene) propanedinitrile (abbreviation: DCM1), 2- {2-Methyl-6- [2- (2,3,6,7-tetrahydro-1H, 5H-benzo [ij] quinolidin-9-yl) ethenyl] -4H-pyran-4-ylidene} propanedi Nitrile (abbreviation: DCM2), N, N, N ′, N′-tetrakis (4-methylphenyl) tetracene-5, 11-diamine (abbreviation: p-mPhTD), 7, 14- Phenyl-N, N, N ′, N′-tetrakis (4-methylphenyl) acenaphtho [1,2-a] fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), 2- {2-isopropyl-6, -[2- (1,1,7,7-Tetramethyl-2,3,6,7-tetrahydro-1H, 5H-benzo [ij] quinolizine-9-yl) ethenyl] -4H-pyran-4-ylidene } Propane dinitrile (abbreviation: DCJTI), 2- {2-tert-butyl-6- [2- (1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H- Benzo [ij] quinolidin-9-yl) ethenyl] -4H-pyran-4-ylidene} propanedinitrile (abbreviation: DCJTB), 2- (2,6-bis {2- [4- (dimethylamino) phenyl]] Ethenyl } -4H-pyran-4-ylidene) propane dinitrile (abbreviation: BisDCM), 2- {2,6-bis [2- (8-methoxy-1,1,7,7-tetramethyl-2,3,3 6,7-Tetrahydro-1H, 5H-benzo [ij] quinolidin-9-yl) ethenyl] -4H-pyran-4-ylidene} propanedinitrile (abbreviation: BisDCJTM) and the like can be mentioned. In particular, fused aromatic diamine compounds represented by pyrene diamine compounds such as 1,6FLPAPrn and 1,6mMemFLPAPrn are preferable because they have high hole trapping properties and are excellent in luminous efficiency and reliability.

Examples of the material that can be used as the phosphorescent material in the light emitting layer 113 include the following. Tris {2- [5- (2-methylphenyl) -4- (2,6-dimethylphenyl) -4H-1,2,4-triazol-3-yl-κN2] phenyl-κC} iridium (III) ( Abbreviations: [Ir (mpptz-dmp) ₃ ]), tris (5-methyl-3,4-diphenyl-4H-1,2,4-triazolato) iridium (III) (abbreviation: [Ir (Mptz) ₃ ]) 4H, like tris [4- (3-biphenyl) -5-isopropyl-3-phenyl-4H-1,2,4-triazolato] iridium (III) (abbreviation: [Ir (iPrptz-3b) ₃ ]) -Organometallic iridium complex having a triazole skeleton, tris [3-methyl-1- (2-methylphenyl) -5-phenyl-1H-1,2,4-triazolato] iridium (II I) (abbreviation: [Ir (Mptz1-mp) ₃ ]), tris (1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato) iridium (III) (abbreviation: [Ir ( Organometallic iridium complexes having a 1H-triazole skeleton such as Prptz 1-Me) ₃ ]), fac-tris [(1-2,6-diisopropylphenyl) -2-phenyl-1H-imidazole] iridium (III) (III) Abbreviations: [Ir (iPrpmi) ₃ ]), tris [3- (2,6-dimethylphenyl) -7-methylimidazo [1,2-f] phenanthridinato] iridium (III) (abbreviation: [Ir (i) organometallic iridium complexes having an imidazole skeleton such as dmpimpt-Me) ₃ )), bis [2- (4 ', 6'-difluorophenyl) pyri] Dinato-N, C ^{2 ′} ] iridium (III) tetrakis (1-pyrazolyl) borate (abbreviation: FIr 6), 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)], phenyl having an electron withdrawing group such as bis [2- (4 ', 6'-difluorophenyl) pyridinato-N, C ^2' ] iridium (III) acetylacetonate (abbreviation: FIracac) The organic metal iridium complex which makes a pyridine derivative a ligand is mentioned. These are compounds which exhibit blue phosphorescence and are compounds having a light emission peak at 440 nm to 520 nm.

In addition, 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)]), (acetylacetonato) ) Bis [5-methyl-6- (2-methylphenyl) -4-phenylpyrimidinato] iridium (III) (abbreviation: [Ir (mpm ppm) ₂ (acac)]), (acetylacetonato) bis (4) Organometallic iridium complexes having a pyrimidine skeleton such as (6-, 6-diphenylpyrimidinato) iridium (III) (abbreviation: [Ir (dppm) ₂ (acac)]), (acetylacetonato) bis (3,5-) Dimethyl-2-phenylpyrazinato) iridium (III) (abbreviation: [Ir (mppr-Me) ₂ (acac)]), (acetylacetonato) bis (5-isopropyl-3-methyl-2-phenylpyrazina) Doo) iridium (III) _{(abbreviation: [Ir (mppr-iPr)} 2 (acac)] organometallic Ili with) pyrazine skeleton, such as And um complex, tris (2-phenylpyridinato--N, C ^{2 ')} iridium (III) _{(abbreviation: [Ir (ppy) 3]} ), bis (2-phenylpyridinato--N, C ^2') Iridium (III) acetylacetonate (abbreviation: [Ir (ppy) ₂ (acac)]), bis (benzo [h] quinolinato) iridium (III) acetylacetonate (abbreviation: [Ir (bzq) ₂ (acac)] ), Tris (benzo [h] quinolinato) iridium (III) (abbreviation: [Ir (bzq) ₃ ]), tris (2-phenylquinolinato-N, C ^{2 ′} ) iridium (III) (abbreviation: [Ir ( ^b ) pq) ₃ ]), bis (2-phenylquinolinato-N, C ^{2 ′} ) iridium (III) acetylacetonate (abbreviation: [Ir (pq) ₂ (acac)]) Other than organometallic iridium complexes having a lysine skeleton, rare earth metal complexes such as tris (acetylacetonato) (monophenanthroline) terbium (III) (abbreviation: [Tb (acac) ₃ (Phen)]) can be mentioned. These are compounds that mainly emit green phosphorescence and have emission peaks at 500 nm to 600 nm. Note that an organometallic iridium complex having a pyrimidine skeleton is particularly preferable because it is remarkably excellent in reliability and light emission efficiency.

In addition, (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)]), bis [4,6-di (naphthalen-1-yl) pyrimidinato] ( Organometallic iridium complexes having a pyrimidine skeleton such as dipivaloylmethanato) iridium (III) (abbreviation: [Ir (d1 npm) ₂ (dpm)]), (acetylacetonato) bis (2, 3, 5, 5) tri phenylpyrazinato) iridium (III) _{(abbreviation: [Ir (tppr) 2 (} acac)]), bis (2,3,5-triphenyl Rajinato) (dipivaloylmethanato) iridium (III) _{(abbreviation: [Ir (tppr) 2 (} dpm])]), ( acetylacetonato) bis [2,3-bis (4-fluorophenyl) quinoxalinato] iridium Organometallic iridium complexes having a pyrazine skeleton such as (III) (abbreviation: [Ir (Fdpq) ₂ (acac)]), or tris (1-phenylisoquinolinato-N, C ^{2 ′} ) iridium (III) (III) Abbreviations: [Ir (piq) ₃ ]), bis (1-phenylisoquinolinato-N, C ^{2 ′} ) iridium (III) (abbreviation: [Ir (piq) ₂ (acac)]) 2,3,7,8,12,13,17,18-octaethyl-21H, 23H-porphyrin platinum (II) (other than organometallic iridium complexes having) : Or platinum complexes such as PtOEP), tris (1,3-diphenyl-1,3-propanedionato) (monophenanthroline) europium (III) _{(abbreviation: [Eu (DBM) 3 (} Phen)]), tris Rare earth metal complexes such as [1- (2-thenoyl) -3,3,3-trifluoroacetonato] (monophenanthroline) europium (III) (abbreviation: [Eu (TTA) ₃ (Phen)]) Be These are compounds that exhibit red phosphorescence and have emission peaks at 600 nm to 700 nm. In addition, an organometallic iridium complex having a pyrazine skeleton can provide red light emission with good chromaticity.

  In addition to the phosphorescent compounds described above, various phosphorescent materials may be selected and used.

  Note that the organometallic complex of one embodiment of the present invention is preferably used as a phosphorescent material. Since the organometallic complex of one embodiment of the present invention emits light efficiently, a light-emitting element with high emission efficiency can be obtained. In addition, the organometallic complex of one embodiment of the present invention emits green light with good color purity. Therefore, a light-emitting device provided with a light-emitting element using the organometallic complex as a phosphorescent light-emitting substance can be a light-emitting device with favorable color reproducibility. In the case where the light emitting device uses a color filter or a microcavity structure, energy loss can be reduced, so that the light emitting device can have good energy efficiency.

  The following materials can be used as the TADF material.

Fullerene and derivatives thereof, acridine derivatives such as proflavin, eosin and the like. Metal-containing porphyrins including magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), palladium (Pd) and the like. Examples of the metal-containing porphyrin include protoporphyrin-tin fluoride complex (SnF ₂ (Proto IX)), mesoporphyrin-tin fluoride complex (SnF ₂ (Meso IX)), and hematoporphyrin represented by the following structural formula -Tin fluoride complex (SnF ₂ (Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complex (SnF ₂ (Copro III-4Me)), octaethyl porphyrin-tin fluoride complex (SnF ₂ (OEP)) And ethioporphyrin-tin fluoride complex (SnF ₂ (Etio I)), octaethyl porphyrin-platinum chloride complex (PtCl ₂ OEP), and the like.

Also, 2-biphenyl-4,6-bis (12-phenylindolo [2,3-a] carbazol-11-yl) -1,3,5-triazine (PIC-TRZ) represented by the following structural formula Heterocyclic compounds having a π electron excess heteroaromatic ring and a π electron deficient heteroaromatic ring can also be used. Since the heterocyclic compound has a π electron excess heteroaromatic ring and a π electron deficient heteroaromatic ring, it has high electron transportability and hole transportability, which is preferable. 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. The energy difference between the S ₁ level and the T ₁ level is particularly small.

  When the above 1,6-bis (diphenylamino) pyrene derivative is used as a host material of a light emitting layer, 9-phenyl-3- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole : PCzPA), 3- [4- (1-naphthyl) -phenyl] -9-phenyl-9H-carbazole (abbreviation: PCPN), 9- [4- (10-phenyl-9-anthracenyl) phenyl] -9H- Carbazole (abbreviation: 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: 2 m B n f PP A), 9-phenyl-10- {4- ( - phenyl -9H- fluoren-9-yl) - biphenyl-4'-yl} - anthracene (abbreviation: FLPPA) material having an anthracene skeleton of the like. When a substance having an anthracene skeleton is used as a host material, it is possible to realize a light emitting layer having good light emitting efficiency and durability. In particular, CzPA, cgDBCzPA, 2mBnfPPA, PCzPA are very preferable because they exhibit very good properties. The materials exemplified above are particularly suitable as host materials in the case of using a fluorescent substance.

When a material other than the above materials is used as a host material, various carrier transport materials such as a material having an electron transport property and a material having a hole transport property can be used.

As a material having an electron transporting property, for example, bis (10-hydroxybenzo [h] quinolinato) beryllium (II) (abbreviation: BeBq ₂ ), bis (2-methyl-8-quinolinolato) (4-phenylphenolato) Aluminum (III) (abbreviation: BAlq), bis (8-quinolinolato) zinc (II) (abbreviation: Znq), bis [2- (2-benzoxazolyl) phenolato] zinc (II) (abbreviation: ZnPBO), Metal complexes such as bis [2- (2-benzothiazolyl) phenolato] zinc (II) (abbreviation: ZnBTZ) or 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4 -Oxadiazole (abbreviation: PBD), 3- (4-biphenylyl) -4-phenyl-5- (4-tert-butylphenyl) -1,2,4-to Azole (abbreviation: TAZ), 1,3-bis [5- (p-tert-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD-7), 9- [6 4- (5-phenyl-1,3,4-oxadiazol-2-yl) phenyl] -9H-carbazole (abbreviation: CO11), 2,2 ′, 2 ′ ′-(1,3,5-benzene Triyl) tris (1-phenyl-1H-benzoimidazole) (abbreviation: TPBI), 2- [3- (dibenzothiophen-4-yl) phenyl] -1-phenyl-1H-benzoimidazole (abbreviation: mDBTBIm-II) 2) Heterocyclic compounds having a polyazole skeleton such as 2), 2- [3- (dibenzothiophen-4-yl) phenyl] dibenzo [f, h] quinoxaline (abbreviation: 2mDBTPDBq-II), 2 -[3 '-(dibenzothiophen-4-yl) biphenyl-3-yl] dibenzo [f, h] quinoxaline (abbreviation: 2mDBTBPDBq-II), 2- [3'-(9H-carbazol-9-yl) biphenyl -3-yl] dibenzo [f, h] quinoxaline (abbreviation: 2mCzBPDBq), 4,6-bis [3- (phenanthrene-9-yl) phenyl] pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis [b Heterocyclic compounds having a diazine skeleton such as 3- (4-dibenzothienyl) phenyl] pyrimidine (abbreviation: 4,6mDBTP2Pm-II) or 3,5-bis [3- (9H-carbazol-9-yl) phenyl] Pyridine (abbreviation: 35DCzPPy), 1,3,5-tri [3- (3-pyridyl) -phenyl] benzene (abbreviation: TmPy) B) and a heterocyclic compound having a pyridine skeleton such. Among the above-mentioned, a heterocyclic compound having a diazine skeleton and a heterocyclic compound having a pyridine skeleton are preferable because they have excellent reliability. In particular, a heterocyclic compound having a diazine (pyrimidine or pyrazine) skeleton has high electron transportability and also contributes to reduction in driving voltage.

  As a material having a hole transporting property, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB), 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), 4-phenyl-4 ′-(9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBA1BP), 4 4′-diphenyl-4 ′ ′-(9-phenyl-9-H-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 Abbreviations: PCBNBB), 9,9-Dimethyl-N-phenyl-N- [4- (9-phenyl-9H-carbazol-3-yl) phenyl] -fluoren-2-amine (abbr .: PCBAF), N-phenyl Aroma such as -N- [4- (9-phenyl-9H-carbazol-3-yl) phenyl] -spiro-9,9'-bifluoren-2-amine (abbreviation: PCBASF) A compound having an amine skeleton, 1,3-bis (N-carbazolyl) benzene (abbreviation: mCP), 4,4′-di (N-carbazolyl) biphenyl (abbreviation: CBP), 3,6-bis (3, Compounds having a carbazole skeleton such as 5-diphenylphenyl) -9-phenylcarbazole (abbreviation: CzTP), 3,3'-bis (9-phenyl-9H-carbazole) (abbreviation: PCCP), or 4,4 ', 4 ′ ′-(benzene-1,3,5-triyl) tri (dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4- [4- (9-phenyl-9H-fluorene-9-) [Illyl] phenyl] dibenzothiophene (abbreviation: DBTFLP-III), 4- [4- (9-phenyl-9H-fluoren-9-yl) phenyl] -6-phenyldiben Compounds having a thiophene skeleton such as zothiophene (abbreviation: DBTFLP-IV), 4, 4 ′, 4 ′ ′-(benzene-1,3,5-triyl) tri (dibenzofuran) (abbr .: DBF 3 P-II), 4 A compound having a furan skeleton such as-{3- [3- (9-phenyl-9H-fluoren-9-yl) phenyl] phenyl} dibenzofuran (abbreviation: mmDBFFLBi-II) can be mentioned. Among the above, a compound having an aromatic amine skeleton and a compound having a carbazole skeleton are preferable because they have good reliability, have high hole transportability, and contribute to reduction in driving voltage. In addition to the hole transport material described above, the hole transport material may be used from various materials.

  Note that the host material may be a material in which a plurality of substances are mixed, and in the case of using a mixed host material, it is preferable to mix a material having an electron transporting property and a material having a hole transporting property . By mixing the material having the electron transporting property and the material having the hole transporting property, the transportability of the light emitting layer 113 can be easily adjusted, and the control of the recombination region can be easily performed. The ratio of the content of the material having a hole transporting property to the content of the material having an electron transporting property may be a material having a hole transporting property: a material having an electron transporting property = 1: 9 to 9: 1.

  In addition, an exciplex may be formed between these mixed host materials. The energy transfer of the exciplex is selected by forming an exciplex that emits light that overlaps with the wavelength of the absorption band at the lowest energy side of the fluorescent substance, the phosphorescent substance, and the TADF material. Smooth and efficient light emission can be obtained. The configuration is also preferable because the driving voltage is also reduced.

  The light emitting layer 113 having the above-described configuration can be manufactured by co-evaporation using a vacuum evaporation method, or a mixed solution using an inkjet method, a spin coating method, a dip coating method, or the like.

  The electron-transporting layer 114 is a layer containing a substance having an electron-transporting property, and as the substance having an electron-transporting property, a material mentioned as a material having an electron-transporting property which can be used for the host material, anthracene skeleton The material which it has can be used.

  In addition, a layer that controls the movement of electron carriers may be provided between the electron transporting layer and the light emitting layer. This is a layer in which a small amount of a substance having a high electron trapping property is added to the material having a high electron transporting property as described above, and the carrier balance can be adjusted by suppressing the movement of electron carriers. Such a configuration exerts a great effect in suppressing a problem (for example, a decrease in the device life) caused by electrons penetrating through the light emitting layer.

In addition, an electron injecting layer 115 may be provided between the electron transporting layer 114 and the second electrode 102 in contact with the second electrode 102. As the electron injection layer 115, an alkali metal or an alkaline earth metal such as lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ) or the like or a compound thereof can be used. For example, a layer formed of a substance having an electron transporting property can be used which contains an alkali metal or an alkaline earth metal or a compound thereof. Alternatively, electride may be used for the electron injection layer 115. 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. Note that electron injection from the second electrode 102 is efficiently performed by using an electron injection layer 115 in which an alkali metal or an alkaline earth metal is contained in a layer formed of a substance having an electron transporting property. Therefore, it is more preferable.

  As a material for forming the second electrode 102, a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like with a low work function (specifically, 3.8 eV or less) can be used. Specific examples of such cathode materials include alkali metals such as lithium (Li) and cesium (Cs), and Group 1 of the periodic table of elements such as magnesium (Mg), calcium (Ca), and strontium (Sr). Elements belonging to Group 2, alloys containing these (MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb) and alloys containing these are listed. However, by providing an electron injecting layer between the second electrode 102 and the electron transporting layer, indium oxide-tin oxide containing Al, Ag, ITO, silicon or silicon oxide regardless of the magnitude of work function Various conductive materials can be used as the second electrode 102. These conductive materials can be deposited by a sputtering method, an inkjet method, a spin coating method, or the like.

  Further, as a method of forming the EL layer 103, various methods can be used regardless of a dry method or a wet method. For example, a vacuum evaporation method, an inkjet method, a spin coating method, or the like may be used. In addition, each electrode or each layer may be formed using different film formation methods.

  The electrode may also be formed by a wet method using a sol-gel method, or may be formed by a wet method using a paste of a metal material. Alternatively, a dry method such as a sputtering method or a vacuum evaporation method may be used.

  Light emitted from the light-emitting element is extracted outside through one or both of the first electrode 101 and the second electrode 102. Therefore, one or both of the first electrode 101 and the second electrode 102 are formed using a light-transmitting electrode.

  Subsequently, an embodiment of a light-emitting element (hereinafter, also referred to as a stacked element) having a structure in which a plurality of light-emitting units are stacked will be described with reference to FIG. This light emitting element is a light emitting element having a plurality of light emitting units between a pair of electrodes formed of a first electrode and a second electrode. One light emitting unit has a structure similar to that of the EL layer 103 shown in FIG. That is, the light-emitting element illustrated in FIG. 1A can be referred to as a light-emitting element including one light-emitting unit, and the light-emitting element illustrated in FIG. 1B can be referred to as a light-emitting element including a plurality of light-emitting units.

  In FIG. 1B, an EL including a stack of a first light emitting unit 511, a charge generation layer 513, and a second light emitting unit 512 between the first electrode 501 and the second electrode 502. The layer 503 is formed. The first electrode 501 and the second electrode 502 correspond to the first electrode 101 and the second electrode 102 in FIG. 1A, respectively, and the same ones described in the description of FIG. 1A are applied. can do. The first light emitting unit 511 and the second light emitting unit 512 may have the same configuration or different configurations.

  As the charge generation layer 513, a composite material containing an organic compound and a metal oxide is preferably used. As the composite material of the organic compound and the metal oxide, the composite material described as a preferable material of the hole injection layer 111 illustrated in FIG. 1A can be used. A composite material including an organic compound and a metal oxide is excellent in carrier injection property and carrier transport property, so that low voltage drive and low current drive can be realized. When the anode side surface of the light emitting unit is in contact with the charge generation layer, the charge generation layer also plays a role of the hole injection layer of the light emission unit, so the light emitting unit may not be provided with the hole injection layer. .

  Note that the charge generation layer 513 may be formed as a stacked structure in which a layer containing the above composite material and a layer formed of another material are combined. For example, it may be formed by laminating a layer containing a composite material and a layer containing one compound selected from electron donating substances and a compound having a high electron transporting property. Alternatively, the conductive layer may be formed by stacking a layer containing a composite material containing an organic compound and a metal oxide, and a transparent conductive film.

  In addition, an electron injection buffer layer may be provided between the charge generation layer 513 and the light emitting unit on the anode side of the charge generation layer. The electron injection buffer layer is formed by laminating a very thin film of an alkali metal and an electron relay layer containing an electron transporting substance. The extremely thin film of alkali metal corresponds to the electron injection layer 115 and has a function of reducing the electron injection barrier. The electron relay layer prevents interaction between the alkali metal film and the charge generation layer 513, and has a function of delivering electrons smoothly.

The electron transporting substance contained in the electron relay layer is contained in a layer in which the LUMO level of the substance is in contact with the LUMO level of the acceptor substance in the charge generation layer 513 and the electron injecting buffer layer in the light emitting unit on the anode side. It is selected to be between the LUMO level of the substance to be As a specific numerical value of the energy level, the LUMO level of the electron transporting substance contained in the electron relay layer is preferably -5.0 eV or more, preferably -5.0 eV or more and -3.0 eV or less. It is preferable to use a phthalocyanine material or a metal complex having a metal-oxygen bond and an aromatic ligand as the electron transporting substance contained in the electron relay layer. In the case where the electron injection buffer layer is provided, the very thin film of alkali metal of the layer plays a role of the electron injection layer in the light emitting unit on the anode side, and therefore it is not necessary to form the electron injection layer on the light emitting unit.

  In any case, when a voltage is applied to the first electrode 501 and the second electrode 502, the charge generation layer 513 sandwiched between the first light emission unit 511 and the second light emission unit 512 is one light emission unit. What is necessary is just to inject an electron into and to inject a hole into the other light emitting unit. For example, in FIG. 1B, in the case where a voltage is applied such that the potential of the first electrode is higher than the potential of the second electrode, the charge generation layer 513 includes electrons in the first light emitting unit 511. And the holes may be injected into the second light emitting unit 512.

  Although FIG. 1B illustrates a light emitting element having two light emitting units, the present invention can be applied to a light emitting element in which three or more light emitting units are stacked. By arranging a plurality of light emitting units by a charge generation layer between a pair of electrodes, high luminance light emission is possible while maintaining a low current density, and a device having a longer life can be realized. In addition, a light-emitting device which can be driven at low voltage and consumes low power can be realized.

  Further, by making the light emission colors of the respective light emitting units different, light emission of a desired color tone can be obtained as the whole light emitting element. For example, in a light emitting element having two light emitting units, a light emitting element emitting white light as a whole light emitting element by obtaining red and green light emitting colors in the first light emitting unit and blue light emitting color in the second light emitting unit It is easy to get.

<< Micro optical resonator (micro cavity) structure >>
A light emitting element having a microcavity structure can be obtained by forming the pair of electrodes from a reflective electrode and a semitransparent / semireflective electrode. The reflective electrode and the semi-transmissive and semi-reflective electrode correspond to the first electrode and the second electrode described above. At least an EL layer is provided between the reflective electrode and the semi-transmissive and semi-reflective electrode, and the EL layer has a light-emitting layer to be at least a light emitting region.

The light emitted from the light emitting layer included in the EL layer is reflected by the reflective electrode and the semi-transmissive and semi-reflective electrode to resonate. The reflective electrode is formed of a conductive material having reflectivity, and the visible light reflectance thereof is 40% to 100%, preferably 70% to 100%, and the resistivity is 1 × 10 ^−. Suppose that it is ² Ωcm or less. In addition, the semi-transmissive and semi-reflective electrode is formed of a conductive material having reflectivity and transmissivity, and the visible light reflectance to it is 20% to 80%, preferably 40% to 70%, It is assumed that the resistivity is 1 × 10 ⁻² Ωcm or less.

  In the light emitting element, the optical distance between the reflective electrode and the semitransparent / semireflective electrode can be changed by changing the thickness of the transparent conductive film, the above-described composite material, the carrier transport material, or the like. Thus, light of a resonating wavelength can be intensified between the reflective electrode and the semi-transmissive / semi-reflective electrode, and light of a non-resonant wavelength can be attenuated.

  Of the light emitted from the light emitting layer, light (first reflected light) reflected and returned by the reflective electrode is light (first incident light) directly incident on the semi-transmissive and semi-reflective electrode from the light emitting layer It is preferable to adjust the optical distance between the reflective electrode and the light emitting layer to (2 n-1) λ / 4 (where n is a natural number of 1 or more and λ is the wavelength of the color to be amplified). Thereby, the phases of the first reflected light and the first incident light can be matched to further amplify the light emission from the light emitting layer.

  In the above structure, the EL layer may have a plurality of light emitting layers or may have a single light emitting layer. For example, in combination with the above-described tandem light emitting element, The present invention may be applied to a configuration in which a plurality of EL layers are provided in one light emitting element with a charge generation layer interposed therebetween, and one or more light emitting layers are formed in each of the EL layers.

«Light-emitting device»
A light-emitting device of one embodiment of the present invention is described with reference to FIG. Note that FIG. 2A is a top view of the light emitting device, and FIG. 2B is a cross-sectional view of FIG. 2A taken along the lines A-B and C-D. The light emitting device includes a drive circuit portion (source line drive circuit) 601, a pixel portion 602, and a drive circuit portion (gate line drive circuit) 603, which are shown by dotted lines, for controlling light emission of the light emitting element. In addition, reference numeral 604 denotes a sealing substrate, reference numeral 605 denotes a sealing material, and the inside surrounded by the sealing material 605 is a space 607.

  Note that the lead wiring 608 is a wiring for transmitting a signal input to the source line driver circuit 601 and the gate line driver circuit 603, and a video signal and a clock signal from an FPC (flexible printed circuit) 609 serving as an external input terminal. Receive start signal, reset signal, etc. Although only the FPC is illustrated here, a printed wiring board (PWB) may be attached to the FPC. The light emitting device in the present specification includes not only the light emitting device main body but also a state in which an FPC or a PWB is attached thereto.

  Next, the cross-sectional structure will be described with reference to FIG. Although a driver circuit portion and a pixel portion are formed over the element substrate 610, here, a source line driver circuit 601 which is a driver circuit portion and one pixel in the pixel portion 602 are shown.

  Note that the source line driver circuit 601 is formed with a CMOS circuit in which an n-channel FET 623 and a p-channel FET 624 are combined. Further, the driver circuit may be formed of various CMOS circuits, PMOS circuits, or NMOS circuits. Further, although the driver integrated type in which the drive circuit is formed on the substrate is shown in this embodiment mode, the driver circuit is not necessarily required, and the drive circuit can be formed not on the substrate but on the outside.

  Although the pixel portion 602 is formed of a plurality of pixels including the switching FET 611, the current control FET 612, and the first electrode 613 electrically connected to the drain thereof, the present invention is not limited to this. The pixel portion may be a combination of three or more FETs and a capacitor.

  There is no particular limitation on the type and crystallinity of the semiconductor used for the FET, and an amorphous semiconductor or a crystalline semiconductor may be used. As an example of a semiconductor used for the FET, a Group 13 (gallium etc.) semiconductor, a Group 14 (silicon etc.) semiconductor, a compound semiconductor, an oxide semiconductor, an organic semiconductor material can be used, and in particular, the oxide semiconductor can be used. It is preferable to use. As the oxide semiconductor, for example, In-Ga oxide, In-M-Zn oxide (M is Al, Ga, Y, Zr, La, Ce, or Nd), and the like can be given. Note that by using an oxide semiconductor material with an energy gap of 2 eV or more, preferably 2.5 eV or more, more preferably 3 eV or more, the off-state current of the transistor can be reduced, which is a preferable structure.

  Note that an insulator 614 is formed to cover an end portion of the first electrode 613. Here, it can be formed by using a positive photosensitive acrylic resin film.

  In addition, in order to improve coverage, a curved surface having a curvature is formed at the upper end portion or the lower end portion of the insulator 614. For example, in the case of using positive photosensitive acrylic as the material of the insulator 614, it is preferable that only the upper end portion of the insulator 614 have a curved surface with a curvature radius (0.2 μm to 3 μm). Further, as the insulator 614, any of negative photosensitive resin and positive photosensitive resin can be used.

  Over the first electrode 613, an EL layer 616 and a second electrode 617 are formed. These are the first electrode 101, the EL layer 103, and the second electrode 102 described in FIG. 1A, or the first electrode 501, the EL layer 503, and the second electrode 502 described in FIG. 1B. It corresponds to

  The EL layer 616 preferably contains the organometallic complex of one embodiment of the present invention. The organometallic complex is preferably used as a luminescent center substance in the light emitting layer.

  Furthermore, by bonding the sealing substrate 604 to the element substrate 610 with the sealant 605, the light emitting element 618 is provided in the space 607 surrounded by the element substrate 610, the sealing substrate 604, and the sealant 605. There is. In addition to the case where the space 607 is filled with a filler and an inert gas (such as nitrogen or argon) is filled, the space 607 may be filled with a sealant 605. When a concave portion is formed in the sealing substrate and a desiccant is provided there, deterioration due to the influence of moisture can be suppressed, which is a preferable configuration.

  It is preferable to use an epoxy resin or glass frit as the sealing material 605. In addition, it is desirable that these materials do not transmit moisture and oxygen as much as possible. Further, as a material used for the element substrate 610 and the sealing substrate 604, in addition to a glass substrate and a quartz substrate, a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (polyvinyl fluoride), polyester, acrylic, or the like can be used.

  For example, in this specification and the like, various substrates can be used to form a transistor or a light-emitting element. The type of substrate is not limited to a specific one. 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 substrate film. Examples of the glass substrate include barium borosilicate glass, aluminoborosilicate glass, or soda lime glass. Examples of the flexible substrate, the laminated film, the base film and the like include the following. For example, there are plastics represented by polyethylene terephthalate (PET), polyethylene naphthalate (PEN) and polyether sulfone (PES). Alternatively, as an example, there is a synthetic resin such as acrylic. Alternatively, examples include polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride and the like. Alternatively, examples include polyamide, polyimide, aramid, epoxy, inorganic vapor deposited film, or papers. In particular, by manufacturing a transistor using a semiconductor substrate, a single crystal substrate, an SOI substrate, or the like, a transistor with small variation in characteristics, size, or shape, high current ability, and small size can be manufactured. . When a circuit is formed using such a transistor, power consumption of the circuit can be reduced or integration of the circuit can be increased.

  Alternatively, a flexible substrate may be used as the substrate, and a transistor or a light emitting element may be formed directly on the flexible substrate. Alternatively, a peeling layer may be provided between the substrate and the transistor, or between the substrate and the light emitting element. The release layer can be used for separation from a substrate and reprinting on another substrate after the semiconductor device is partially or completely completed thereon. At that time, the transistor can also be transferred to a substrate with poor heat resistance or a flexible substrate. Note that for the above-described release layer, for example, a configuration of a stacked structure of an inorganic film of a tungsten film and a silicon oxide film, a configuration in which an organic resin film such as polyimide is formed on a substrate, or the like can be used.

That is, a transistor or a light emitting element may be formed using a certain substrate, and then, the transistor or the light emitting element may be transposed to another substrate, and the transistor or the light emitting element may be disposed on another substrate. As an example of a substrate on which a transistor or a light emitting element is transferred, a paper substrate, a cellophane substrate, an aramid film substrate, a polyimide film substrate, a stone substrate, a wood substrate, a cloth substrate, in addition to a substrate capable of forming the above transistor (Natural fibers (silk, cotton, hemp), synthetic fibers (nylon, polyurethane, polyester) or regenerated fibers (acetate, cupra, rayon, regenerated polyester, etc. are included), leather substrates, rubber substrates, etc. By using these substrates, formation of a transistor with good characteristics, formation of a transistor with low power consumption, manufacture of a device that is not easily broken, provision of heat resistance, weight reduction, or thickness reduction can be achieved.

  FIG. 3 illustrates an example of a light-emitting device in which a light-emitting element exhibiting white light emission is formed and a full color is achieved by providing a coloring layer (color filter) or the like. In FIG. 3A, a substrate 1001, a base insulating film 1002, a gate insulating film 1003, gate electrodes 1006, 1007, and 1008, a first interlayer insulating film 1020, a second interlayer insulating film 1021, a peripheral portion 1042, a pixel portion. 1040, a driver circuit portion 1041, first electrodes 1024W, 1024R, 1024G and 1024B of light emitting elements, partition walls 1025, an EL layer 1028, second electrodes 1029 of light emitting elements, a sealing substrate 1031, a sealing material 1032, and the like are illustrated. ing.

  In FIG. 3A, the coloring layers (red coloring layer 1034R, green coloring layer 1034G, blue coloring layer 1034B) are provided over the transparent base 1033. In addition, a black layer (black matrix) 1035 may be further provided. The transparent substrate 1033 provided with the colored layer and the black layer is aligned and fixed to the substrate 1001. The colored layer and the black layer are covered with an overcoat layer 1036. Further, in FIG. 3A, there are a light emitting layer where light does not pass through the colored layer but goes outside, and a light emitting layer where light passes through the colored layer of each color and the light goes out, and the light passes through the colored layer. Since the non-light is white and the light passing through the colored layer is red, blue, and green, the image can be represented by pixels of four colors.

  Note that a light-emitting element using the organometallic complex of one embodiment of the present invention as one of light-emitting substances is a light-emitting element that can provide light emission with good color purity. In addition, a light-emitting element with high light emission efficiency can be provided, and a light-emitting element with low power consumption can also be provided. In addition, the light-emitting element can have high heat resistance.

  FIG. 3B shows an example of forming a coloring layer (red coloring layer 1034R, green coloring layer 1034G, blue coloring layer 1034B) between the gate insulating film 1003 and the first interlayer insulating film 1020. . As described above, the coloring layer may be provided between the substrate 1001 and the sealing substrate 1031.

  In the light emitting device described above, although the light emitting device has a structure (bottom emission type) for extracting light to the side of the substrate 1001 where the FET is formed, a structure for extracting light emission to the sealing substrate 1031 side (top emission type The light emitting device of A cross-sectional view of the top emission type light emitting device is shown in FIG. In this case, a substrate which does not transmit light can be used as the substrate 1001. Until a connection electrode for connecting the FET and the anode of the light emitting element is manufactured, it is formed in the same manner as the bottom emission type light emitting device. Thereafter, a third interlayer insulating film 1037 is formed to cover the electrode 1022. This insulating film may play a role of planarization. The third interlayer insulating film 1037 can be formed using various other materials in addition to the same material as the second interlayer insulating film.

  The first electrodes 1024 W, 1024 R, 1024 G, and 1024 B of the light emitting element are here an anode, but may be a cathode. In the case of a top emission type light emitting device as shown in FIG. 4, it is preferable that the first electrode be a reflective electrode. The structure of the EL layer 1028 is a structure as described for the EL layer 103 in FIG. 1A or the EL layer 503 in FIG. 1B, and has a device structure in which white light emission can be obtained.

  In the top emission structure as illustrated in FIG. 4, sealing can be performed with a sealing substrate 1031 provided with colored layers (red colored layer 1034 R, green colored layer 1034 G, and blue colored layer 1034 B). A black layer (black matrix) 1035 may be provided on the sealing substrate 1031 so as to be located between the pixels. The colored layer (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B) or the black layer may be covered with the overcoat layer 1036. Note that a light-transmitting substrate is used for the sealing substrate 1031.

  In addition, although an example of performing full color display with four colors of red, green, blue and white is shown here, it is not particularly limited, and full color with three colors of red, green and blue or four colors of red, green, blue and yellow You may display it.

  FIG. 5 illustrates a passive matrix light-emitting device which is one embodiment of the present invention. 5A is a perspective view of the light emitting device, and FIG. 5B is a cross-sectional view of FIG. 5A taken along the line X-Y. In FIG. 5, an EL layer 955 is provided between the electrode 952 and the electrode 956 over the substrate 951. The end of the electrode 952 is covered with an insulating layer 953. A partition layer 954 is provided over the insulating layer 953. The side walls of the partition layer 954 have a slope such that the distance between one side wall and the other side wall becomes narrower as the wall surface becomes closer to the substrate surface. That is, the cross section in the short side direction of the partition layer 954 has a trapezoidal shape, and the base (the side similar to the surface direction of the insulating layer 953 and the side in contact with the insulating layer 953) is the upper side (the surface of the insulating layer 953). It is oriented in the same direction as the direction and shorter than the side not in contact with the insulating layer 953). By providing the partition layer 954 in this manner, defects of the light-emitting element due to static electricity or the like can be prevented.

  The above-described light-emitting device can control a large number of minute light-emitting elements arranged in a matrix with the FETs formed in the pixel portion, and thus is preferably used as a display device for expressing an image. It is a light emitting device that can be used.

«Lighting device»
A lighting device which is an embodiment of the present invention will be described with reference to FIG. FIG. 6 (B) is a top view of the lighting device, and FIG. 6 (A) is a cross-sectional view taken along the line e-f in FIG.

  In the lighting device, the first electrode 401 is formed over a light-transmitting substrate 400 which is a support. The first electrode 401 corresponds to the first electrode 101 in FIGS. 1A and 1B. In the case of extracting light emission from the first electrode 401 side, the first electrode 401 is formed of a light-transmitting material.

  A pad 412 for applying a voltage to the second electrode 404 is formed on the substrate 400.

  An EL layer 403 is formed over the first electrode 401. The EL layer 403 corresponds to the EL layer 103 or the EL layer 503 in FIGS. 1A and 1B. In addition, please refer to the said description about these structures.

  The second electrode 404 is formed to cover the EL layer 403. The second electrode 404 corresponds to the second electrode 102 in FIG. In the case where light emission is extracted from the first electrode 401 side, the second electrode 404 is formed to include a material with high reflectance. The second electrode 404 is connected to the pad 412 to supply a voltage.

  A light emitting element is formed by the first electrode 401, the EL layer 403, and the second electrode 404. The sealing substrate 407 is fixed and sealed using the sealants 405 and 406 to complete the lighting device. Either of the sealing materials 405 and 406 may be used. In addition, a desiccant can be mixed with the inner sealing material 406 (not shown in FIG. 6B), which can adsorb moisture, which leads to improvement in reliability.

  In addition, the pad 412 and a part of the first electrode 401 can be extended outside the sealants 405 and 406 to be an external input terminal. In addition, an IC chip 420 or the like mounted with a converter or the like may be provided thereon.

«Electronic equipment»
An example of an electronic device which is an embodiment of the present invention is described. As an electronic device, for example, a television device (also referred to as a television or a television receiver), a monitor for a computer, a digital camera, a digital video camera, a digital photo frame, a mobile phone (also referred to as a mobile phone or a mobile phone device) And large game machines such as portable game machines, portable information terminals, sound reproduction devices, and pachinko machines. Specific examples of these electronic devices are shown below.

FIG. 7A illustrates an example of a television set. In a television set, a display portion 7103 is incorporated in a housing 7101. Further, here, a structure in which the housing 7101 is supported by the stand 7105 is shown. Images can be displayed by the display portion 7103. The display portion 7103 is configured by arranging light emitting elements in a matrix.

The television set can be operated by an operation switch of the housing 7101 or a separate remote controller 7110. Channels and volume can be controlled with an operation key 7109 of the remote controller 7110, and an image displayed on the display portion 7103 can be manipulated. Further, the remote control 7110 may be provided with a display portion 7107 for displaying information output from the remote control 7110.

Note that the television set is provided with a receiver, a modem, and the like. Receivers can receive general television broadcasts, and by connecting to a wired or wireless communication network via a modem, one-way (sender to receiver) or two-way (sender and receiver) It is also possible to perform information communication between receivers or between receivers.

FIG. 7B1 illustrates a computer, which includes a main body 7201, a housing 7202, a display portion 7203, a keyboard 7204, an external connection port 7205, a pointing device 7206, and the like. Note that this computer is manufactured by arranging light emitting elements in a matrix and using them for the display portion 7203. The computer shown in FIG. 7 (B1) may have a form as shown in FIG. 7 (B2). The computer illustrated in FIG. 7B2 is provided with a second display portion 7210 instead of the keyboard 7204 and the pointing device 7206. The second display portion 7210 is a touch panel type, and an input can be performed by operating the display for input displayed on the second display portion 7210 with a finger or a dedicated pen. Further, the second display unit 7210 can display not only the input display but also other images. The display portion 7203 may also be a touch panel. By connecting the two screens with a hinge, it is possible to prevent the occurrence of troubles such as damage to the screen during storage and transportation.

FIGS. 7C and 7D show an example of a portable information terminal. The portable information terminal includes an operation button 7403, an external connection port 7404, a speaker 7405, a microphone 7406, and the like in addition to the display portion 7402 incorporated in a housing 7401. Note that the portable information terminal includes a display portion 7402 which is manufactured by arranging light emitting elements in a matrix.

The portable information terminals illustrated in FIGS. 7C and 7D can have a structure in which information can be input by touching the display portion 7402 with a finger or the like. In this case, operations such as making a call and creating an e-mail can be performed by touching the display portion 7402 with a finger or the like.

The screen of the display portion 7402 mainly has three modes. The first is a display mode mainly for displaying an image, and the second is an input mode mainly for inputting information such as characters. The third is a display + input mode in which two modes of the display mode and the input mode are mixed.

For example, in the case of making a call or text messaging, the display portion 7402 may be in a text input mode mainly for text input, and text input operation can be performed on the screen. In this case, it is preferable to display a keyboard or a number button on most of the screen of the display portion 7402.

In addition, by providing a detection device having a sensor that detects inclination, such as a gyro or an acceleration sensor, inside the mobile phone, the orientation (longitudinal or horizontal) of the mobile phone is determined, and the screen display of the display portion 7402 is automatically performed. Can be switched.

The screen mode is switched by touching the display portion 7402 or operating the operation button 7403 of the housing 7401. In addition, switching can be performed according to the type of image displayed on the display portion 7402. For example, the display mode is switched if the image signal displayed on the display unit is data of a moving image, and the input mode is switched if the data is text data.

In the input mode, a signal detected by the light sensor of the display portion 7402 is detected, and when there is no input by a touch operation on the display portion 7402, the screen mode is switched from the input mode to the display mode. You may control.

The display portion 7402 can also function as an image sensor. For example, personal identification can be performed by touching the display portion 7402 with a palm or a finger and capturing a palm print, a fingerprint, or the like. In addition, when a backlight which emits near-infrared light or a sensing light source which emits near-infrared light is used for the display portion, an image of a finger vein, a palm vein, or the like can be taken.

Note that the above electronic devices can be used in appropriate combination with the structures shown in this specification.

  Further, it is preferable to use a light-emitting element including the organometallic complex of one embodiment of the present invention in the display portion. Since the light-emitting element can be a light-emitting element with high light emission efficiency, an electronic device with low power consumption can be obtained. In addition, it is easy to obtain an electronic device with high heat resistance. In addition, since the light-emitting element has high color purity, electronic devices with high display quality can be obtained.

  FIG. 8 shows an example of a liquid crystal display device in which a light emitting element is applied to a backlight. The liquid crystal display device illustrated in FIG. 8 includes a housing 901, a liquid crystal layer 902, a backlight unit 903, and a housing 904. The liquid crystal layer 902 is connected to a driver IC 905. A light emitting element is used for the backlight unit 903, and current is supplied from the terminal 906.

  It is preferable to use a light-emitting element including the organometallic complex of one embodiment of the present invention for the light-emitting element, and by applying the light-emitting element to a backlight of a liquid crystal display device, a backlight with reduced power consumption can be obtained. . In addition, a backlight having excellent heat resistance can be obtained.

  FIG. 9 is an example of a desk lamp which is an embodiment of the present invention. The desk lamp illustrated in FIG. 9 includes a housing 2001 and a light source 2002, and a lighting device using a light-emitting element as the light source 2002 is used.

  FIG. 10 shows an example of the indoor lighting device 3001. It is preferable to use a light-emitting element including the organometallic complex of one embodiment of the present invention for the lighting device 3001.

  An automobile according to one aspect of the present invention is shown in FIG. The car has a light emitting element mounted on a windshield or a dashboard. The display area 5000 to the display area 5005 are display areas provided using light-emitting elements. The organometallic complex of one embodiment of the present invention is preferably used, and by using the organometallic complex, a light-emitting element with low power consumption can be obtained. Further, the display area 5000 to the display area 5005 can reduce power consumption, which is suitable for on-vehicle use. In addition, since the organometallic complex has high heat resistance and can also improve the heat resistance of the display region 5000 to the display region 5005, the organometallic complex is suitable for use in vehicles.

  A display area 5000 and a display area 5001 are display devices using light emitting elements provided on a windshield of a car. By manufacturing the light-emitting element using the light-transmitting electrode as the first electrode and the second electrode, a display device in a so-called see-through state can be obtained in which the opposite side can be seen through. If it is a see-through display, even if it is installed on the windshield of a car, it can be installed without obstructing the view. Note that in the case where a transistor or the like for driving is provided, a light-transmitting transistor such as an organic transistor made of an organic semiconductor material or a transistor using an oxide semiconductor is preferably used.

  A display region 5002 is a display device using a light emitting element provided in a pillar portion. By projecting an image from the imaging means provided in the vehicle body in the display area 5002, the view blocked by the pillar can be complemented. Also, similarly, the display area 5003 provided in the dashboard part compensates for the blind spot and improves the safety by projecting the image from the imaging means provided outside the car, as the view blocked by the vehicle body. Can. By projecting the image so as to complement the invisible part, it is possible to check the safety more naturally and without discomfort.

  The display area 5004 and the display area 5005 can provide various other information such as navigation information, speedometer, number of revolutions, traveling distance, oil supply amount, gear state, setting of air conditioning, and the like. The display items can be changed as appropriate in accordance with the preference of the user. These pieces of information can also be provided in the display area 5000 to the display area 5003. The display region 5000 to the display region 5005 can also be used as lighting devices.

  12A and 12B illustrate an example of a foldable tablet terminal. FIG. 12A shows an open state, and the tablet terminal includes a housing 9630, a display portion 9631a, a display portion 9631b, a display mode switching switch 9034, a power switch 9035, a power saving mode switching switch 9036, and a fastener 9033. , And an operation switch 9038. Note that the tablet terminal is manufactured using the light-emitting device including the light-emitting element including the organometallic complex of one embodiment of the present invention for one or both of the display portion 9631 a and the display portion 9631 b.

  A portion of the display portion 9631 a can be a touch panel area 9632 a, and data can be input by touching the displayed operation key 9637. Note that in the display portion 9631 a, as an example, a structure in which a half area has a display only function and the other half area has a structure having a touch panel function is not limited thereto. The whole area of the display portion 9631 a may have a touch panel function. For example, the entire surface of the display portion 9631 a can be displayed as a keyboard button to be a touch panel, and the display portion 9631 b can be used as a display screen.

  Further, in the display portion 9631 b, as in the display portion 9631 a, part of the display portion 9631 b can be used as the touch panel area 9632 b. In addition, the keyboard button can be displayed on the display portion 9631 b by touching the position where the keyboard display switching button 9639 on the touch panel is displayed with a finger, a stylus, or the like.

  Further, touch input can be performed simultaneously on the touch panel area 9632 a and the touch panel area 9632 b.

  Further, the display mode switching switch 9034 can switch the display orientation such as vertical display or horizontal display, and can select switching between black and white display and color display. The power saving mode switching switch 9036 can optimize the display brightness in accordance with the amount of external light at the time of use detected by the light sensor incorporated in the tablet type terminal. The tablet type terminal may incorporate not only an optical sensor but also other detection devices such as a sensor for detecting inclination of a gyro, an acceleration sensor or the like.

  12A shows an example in which the display areas of the display portion 9631 b and the display portion 9631 a are the same, but is not particularly limited, one size may be different from the other size, and the display quality is also shown. It may be different. For example, a display panel in which one can perform higher definition display than the other may be used.

  FIG. 12B shows a closed state, and the tablet terminal in this embodiment includes the housing 9630, a solar cell 9633, a charge and discharge control circuit 9634, a battery 9635, and a DCDC converter 9636. Note that FIG. 12B illustrates a structure including a battery 9635 and a DCDC converter 9636 as an example of the charge and discharge control circuit 9634.

  Note that since the tablet terminal can be folded in half, the housing 9630 can be closed when not in use. Therefore, since the display portion 9631 a and the display portion 9631 b can be protected, it is possible to provide a tablet terminal which is excellent in durability and excellent in reliability even from the viewpoint of long-term use.

  In addition to this, the tablet type terminal shown in FIGS. 12A and 12B has a function of displaying various information (still image, moving image, text image, etc.), a calendar, a date or time, etc. A function of displaying on the display portion, a touch input function of performing touch input operation or editing of information displayed on the display portion, a function of controlling processing by various software (programs), and the like can be provided.

  Electric power can be supplied to the touch panel, the display portion, the video signal processing portion, or the like by the solar battery 9633 mounted on the surface of the tablet terminal. Note that the solar battery 9633 is preferably provided on one surface or two surfaces of the housing 9630 because efficient charging of the battery 9635 can be performed.

  The structure and operation of the charge and discharge control circuit 9634 illustrated in FIG. 12B will be described with reference to a block diagram in FIG. FIG. 12C illustrates a solar cell 9633, a battery 9635, a DCDC converter 9636, a converter 9638, switches SW1 to SW3, and a display portion 9631. The battery 9635, a DCDC converter 9636, a converter 9638, and switches SW1 to SW3 are illustrated. 12B corresponds to the charge / discharge control circuit 9634 shown in FIG.

  First, an example of operation in the case where electric power is generated by the solar battery 9633 by external light will be described. The electric power generated by the solar cell is boosted or lowered by DCDC converter 9636 to a voltage for charging battery 9635. Then, when the power charged by the solar cell 9633 is used for the operation of the display portion 9631, the switch SW 1 is turned on, and the converter 9638 boosts or steps down the voltage necessary for the display portion 9631. In addition, when display on the display portion 9631 is not performed, the switch SW1 may be turned off, the switch SW2 may be turned on, and the battery 9635 may be charged.

  Although the solar cell 9633 is illustrated as an example of the power generation means, the power generation means is not particularly limited, and charging of the battery 9635 is performed by another power generation means such as a piezoelectric element (piezo element) or a thermoelectric conversion element (Peltier element). May be configured to A non-contact power transmission module that charges by transmitting and receiving power wirelessly (without contact) may be combined with another charging unit, or may not have a power generation unit.

  Note that the organometallic complex of one embodiment of the present invention can be used for an organic thin film solar cell. More specifically, since it has carrier transportability, it can be used for a carrier transport layer. Moreover, since it excites light, it can be used as a power generation layer.

  Further, as long as the display portion 9631 is provided, the present invention is not limited to the tablet terminal having the shape shown in FIG.

In this example, bis {2- [6- (2-methylpropyl) -4-pyrimidinyl-κN3] dibenzofuran-3-yl-κC} (2,4-pentanedionato-κ ² O, O ') iridium A method of synthesizing (III) (abbreviation: [Ir (iBudbfpm) ₂ (acac)]) will be described. The structural formula of [Ir (iBudbfpm) ₂ (acac)] is shown below.

Step 1: Synthesis of 4-chloro-6- (2-methylpropyl) pyrimidine
First, 1.02 g of 4,6-dichloropyrimidine, 0.14 g of tris (2,4-pentanedionato) iron (III) (abbreviation: Fe (acac) ₃ ), 67 mL of dry THF, 1-methyl-2-pyrrolidone ( Abbreviation: After putting 5.6 mL of NMP) into a 200 mL three-necked flask, the inside of the flask was purged with nitrogen. After ice-cooling the flask, 6.7 mL of a 1 M THF solution of isobutyl magnesium bromide (abbreviation: iBuMgBr) was added, and the mixture was stirred at room temperature for 20 and a half hours. Thereafter, 1 M hydrochloric acid was added, and the organic layer was extracted with ethyl acetate. The obtained extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over magnesium sulfate. The dried solution was filtered. After evaporating the solvent of this solution, the obtained residue was purified by flash column chromatography using dichloromethane: ethyl acetate = 10: 1 (volume ratio) as a developing solvent to obtain the desired product (yellow oil , Yield 65%). The synthesis scheme of Step 1 is shown in the following (a-1).

<Step 2; Synthesis of 4- (dibenzofuran-2-yl) -6- (2-methylpropyl) pyrimidine (abbreviation: HiBudbfpm)>
Next, 1.49 g of 4-chloro-6- (2-methylpropyl) pyrimidine obtained in Step 1 above and 2.78 g of dibenzofuran-2-ylboronic acid, 1.39 g of sodium carbonate, bis (triphenylphosphine) palladium ( II) 0.077 g of dichloride (abbreviation: Pd (PPh ₃ ) ₂ Cl ₂ ), 20 mL of water, and 20 mL of DMF were placed in an eggplant flask equipped with a reflux condenser, and the inside was purged with argon. The reaction vessel was heated by irradiating with microwave (2.45 GHz 100 W) for 2 hours. Thereafter, water was added to the solution, and the organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and saturated brine and dried over magnesium sulfate. The dried solution was filtered. After evaporating the solvent of this solution, the obtained residue was purified by flash column chromatography using hexane: ethyl acetate = 2: 1 (volume ratio) as a developing solvent to obtain the target pyrimidine derivative HiBudbfpm ( Yellow oil, yield 98%). Note that microwave irradiation was performed using a microwave synthesis apparatus (Discover, manufactured by CEM Corporation). The synthesis scheme of Step 2 is shown in (b-1) below.

<Step 3; Di-μ-chloro-tetrakis {2- [6- (2-methylpropyl) -4-pyrimidinyl-κN3] dibenzofuran-3-yl-κC} diiridium (III) (abbreviation: [Ir (iBudbfpm) )) ₂ Cl] ₂ ) synthesis>
Next, 15 mL of 2-ethoxyethanol, 5 mL of water, 1.17 g of HiBudbfpm obtained in the above step 2, and 0.57 g of iridium chloride hydrate (IrCl ₃ .nH ₂ O) (manufactured by Heraeus) were attached to a reflux tube. The flask was placed in an eggplant flask, and the inside of the flask was purged with argon. Thereafter, microwave (2.45 GHz 100 W) was irradiated for 1 hour to react. After distilling off the solvent, the obtained residue was suction-filtered and washed with methanol to obtain a dinuclear complex [Ir (iBudbfpm) ₂ Cl] ₂ (greenish brown powder, yield 82%). Moreover, the synthesis scheme of Step 3 is shown in the following (c-1).

<Step 4; Bis {2- [6- (2-methylpropyl) -4-pyrimidinyl-κN3] dibenzofuran-3-yl-κC} (2,4-pentanedionato-κ ² O, O ′) iridium III) (abbreviation: Synthesis of [Ir (iBudbfpm) ₂ (acac)]>
Furthermore, 30 mL of 2-ethoxyethanol, 1.03 g of the binuclear complex [Ir (iBudbfpm) ₂ Cl] ₂ obtained in step 3 above, 0.18 g of acetylacetone (abbreviation: Hacac) and 0.64 g of sodium carbonate are attached to a reflux condenser. The flask was placed in an eggplant flask, and the inside of the flask was purged with argon. Then, it heated by irradiating a microwave (2.45 GHz 120 W) for 60 minutes. Here, 0.18 g of Hacac was further added, and the reaction vessel was heated by irradiating with microwave (2.45 GHz 120 W) for 60 minutes. The resulting mixture was suction filtered with methanol, washed with water and methanol. The obtained solid is dissolved in dichloromethane, filtered through a filter aid laminated in the order of celite, alumina and celite, and then recrystallized in a mixed solvent of dichloromethane and methanol to obtain the organometallic complex [Ir (i) of the present invention. iBudbfpm) ₂ (acac)] was obtained as a yellow-orange powder (yield 26%). 0.28 g of the obtained yellow-orange powder solid was sublimated and purified by a train sublimation method. The sublimation purification was performed under the conditions of a pressure of 2.7 Pa, an argon gas flow rate of 5 mL / min, and a heating temperature of 310 ° C. After sublimation purification, the target yellow-orange solid was obtained in a yield of 71%. The synthesis scheme of Step 4 is shown in (d-1) below.

Incidentally, showing the nuclear magnetic resonance spectroscopy yellowish orange powder obtained in Step 4 the analysis result by ^{(1 H-NMR)} is shown below. Moreover, a ¹ H-NMR chart is shown in FIG. From this result, it was found that the organometallic complex [Ir (iBudbfpm) ₂ (acac)] of the present invention represented by the above-mentioned structural formula (100) was obtained in this Synthesis Example 1.

¹ H-NMR. δ (CDCl ₃ ): 1.14 (t, 12 H), 1.82 (s, 6 H), 2.35-2.40 (m, 2 H), 2.94 (d, 4 H), 5.32 ( s, 1H), 6.50 (s, 2H), 7.22 (t, 2H), 7.31 (t, 4H), 7.76 (s, 2H), 7.82 (d, 2H), 8.27 (s, 2H), 9.06 (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 (iBudbfpm) ₂ (acac)] were measured. For measurement of absorption spectrum, a dichloromethane solution (0.082 mmol / L) of [Ir (iBudbfpm) ₂ (acac)] is placed in a quartz cell using an ultraviolet-visible spectrophotometer (V550 type manufactured by JASCO Corporation). The measurement was performed at room temperature. In addition, the measurement of the emission spectrum is carried out by using a fluorometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.) and degassing a dichloromethane solution (0.082 mmol / L) of [Ir (iBudbfpm) ₂ (acac)] in a quartz cell. The measurement was performed at room temperature. The obtained absorption spectrum and emission spectrum are shown in FIG. In addition, the absorption spectrum shown in FIG. 14 has shown the result which deducted the absorption spectrum which put only dichloromethane in the quartz cell and was measured from the measured absorption spectrum.

As shown in FIG. 14, the dichloromethane solution of [Ir (iBudbfpm) ₂ (acac)] showed an absorption peak at around 469 nm. Further, the peak of the emission wavelength of the dichloromethane solution was around 537 nm, and green emission was observed.

Next, [Ir (iBudbfpm) ₂ (acac)] obtained in this example was analyzed by liquid chromatography mass spectrometry (abbreviation: LC / MS analysis).

LC / MS analysis was carried out by LC (liquid chromatography) separation by Acquity UPLC manufactured by Waters, and MS analysis (mass spectrometry) by Xevo G2 Tof MS manufactured by Waters. The column used for LC separation was Acquity UPLC BEH C8 (2.1 × 100 mm 1.7 μm), and the column temperature was 40 ° C. Mobile phase A was acetonitrile, and mobile phase B was 0.1% aqueous solution of formic acid. In addition, the sample was prepared by dissolving [Ir (iBudbfpm) ₂ (acac)] of arbitrary concentration in chloroform and diluting with acetonitrile, and the injection volume was 5.0 μL.

  For LC separation, a gradient method that changes the composition of the mobile phase is used, and from 0 minutes to 1 minute after the start of measurement, mobile phase A: mobile phase B = 60: 40, and then change the composition, mobile phase A at 10 minutes And the ratio of the mobile phase B to the mobile phase B was 95: 5. The composition was varied linearly.

  In MS analysis, ionization was performed by electrospray ionization (abbr .: ESI), capillary voltage was 3.0 kV, sample cone voltage was 30 V, and detection was performed in positive mode. The mass range to be measured was m / z 100 to 1200.

  Under the above conditions, the separated and ionized components of m / z = 895.28 collide with argon gas in a collision cell to dissociate into product ions. The energy (collision energy) at the time of collision with argon was 70 eV. The results of detection of the dissociated product ions by time of flight (TOF) MS are shown in FIG.

From the results in FIG. 15, the organometallic complex which is one embodiment of the present invention, which is represented by a structural formula (100), [Ir (iBudbfpm) ₂ (acac)] is mainly m / z = 795.23 and m / z It was found that product ions were detected around z = 750.17 and m / z = 487.05. Incidentally, the results shown in FIG. 15, the _{[Ir (iBudbfpm) 2 (acac} )] Since shows the characteristic results from a, contained in the mixture _{[Ir (iBudbfpm) 2 (acac} )] It can be said that it is important data for identification.

The product ion around m / z = 795.23 is a cation in the compound of structural formula (100) in which protons are separated from acetylacetone, and the product ion around m / z = 487.05 is divalent. It is presumed to be an ion, which is one of the features of the organometallic complex which is one embodiment of the present invention. In addition, the product ion in the vicinity of m / z = 750.17 is presumed to be the elimination of a propyl group derived from the product ion in the vicinity of m / z = 795.23. It is suggested that (iBudbfpm) ₂ (acac)] contains a propyl group.

In this example, tris {2- [6- (2-methylpropyl) -4-pyrimidinyl-κN3] dibenzothiophen-3-yl-κC} iridium (III) (abbreviation: [Ir (iBudbtpm) ₃ ]) is used. The synthesis method will be described. The structural formula of [Ir (iBudbtpm) ₃ ] is shown below.

<Step 1: Synthesis of 2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzothiophene>
First, 2.99 g of 2-bromodibenzothiophene, 3.08 g of bis (pinacolate) diboron, 3.47 g of potassium acetate, and 55 mL of dry DMSO were placed in a 200 mL three-necked flask, and the inside of the flask was purged with nitrogen. After degassing by stirring the inside of the flask under reduced pressure, 0.77 g of bis (triphenylphosphine) palladium (II) dichloride (abbreviation: Pd (PPh ₃ ) ₂ Cl ₂ ) is added, and the reaction is continued at 90 ° C. for 20 hours. Heated. Thereafter, water was added to the solution, and the organic layer was extracted with chloroform. The obtained organic layer was washed with water and saturated brine and dried over magnesium sulfate. The dried solution was filtered. After evaporating the solvent of this solution, the obtained residue was purified by silica gel column chromatography using toluene as a developing solvent to obtain the desired product (light yellow oil, yield 54%). The synthesis scheme of Step 1 is shown in (a-2).

<Step 2; Synthesis of 4- (dibenzothiophen-2-yl) -6- (2-methylpropyl) pyrimidine (abbreviation: HiBudbtpm)>
Next, 1.86 g of 2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzothiophene obtained in step 1 above and 4-chloro-6- (2- 0.87 g of methylpropyl) pyrimidine, 7.6 mL of 1 M aqueous potassium acetate solution, 7.6 mL of 1 M aqueous sodium carbonate solution, and 20 mL of acetonitrile were placed in a 100 mL round bottom flask equipped with a reflux condenser, and the inside of the flask was purged with argon. To this mixture, 0.35 g of tetrakis (triphenylphosphine) palladium (0) (abbreviation: Pd (PPh ₃ ) ₄ ) was added, and the reaction vessel was heated by being irradiated with a microwave (2.45 GHz 100 W) for 2 hours. Water was added to this solution, and the organic layer was extracted with dichloromethane. The obtained organic layer was washed with saturated brine and dried over magnesium sulfate. The dried solution was filtered. After evaporating the solvent of this solution, the obtained residue was purified by flash column chromatography using hexane: ethyl acetate = 2: 1 (volume ratio) as a developing solvent to obtain the target pyrimidine derivative HiBudbtpm ( Yellow oil, 92% yield). Note that microwave irradiation was performed using a microwave synthesis apparatus (Discover, manufactured by CEM Corporation). The synthesis scheme of Step 2 is shown in (b-2).

<Step 3; Di-μ-chloro-tetrakis {2- [6- (2-methylpropyl) -4-pyrimidinyl-κN3] dibenzothiophen-3-yl-κC} diiridium (III) (abbreviation: [Ir ( Synthesis of iBudbtpm) ₂ Cl] ₂ )>
Next, add 15 mL of 2-ethoxyethanol and 5 mL of water, 0.83 g of HiBudbtpm (0.83 g, iridium chloride hydrate (IrCl ₃ · n H ₂ O) (Heraeus)) obtained in Step 2 above, The flask was then purged with argon for 1 hour, and then the reaction mixture was irradiated with microwave (2.45 GHz 100 W) for 1 hour, the solvent was distilled off, and the resulting residue was suction-filtered with methanol. The compound was washed to obtain a binuclear complex [Ir (iBudbtpm) ₂ Cl] ₂ (yellow-brown powder, 85% yield), and the synthesis scheme of Step 3 is shown in (c-2) below.

<Step 4; Synthesis of tris {2- [6- (2-methylpropyl) -4-pyrimidinyl-κN3] dibenzothiophen-3-yl-κC} iridium (III) (abbreviation: [Ir (iBudbtpm) ₃ ]>
Furthermore, 8 g of phenol, 0.69 g of the binuclear complex [Ir (iBudbtpm) ₂ Cl] ₂ obtained in step 3 above, 0.64 g of HiBuddpm and 0.55 g of potassium carbonate are placed in a 200 mL three-necked flask equipped with a reflux condenser, Were replaced with nitrogen. Thereafter, the mixture was reacted by heating at 185 ° C. for 7 and a half hours. The resulting mixture was suction filtered with methanol, washed with water and methanol. The obtained solid was recrystallized with a mixed solvent of dichloromethane and methanol to obtain [Ir (iBudbtpm) ₃ ] as a yellow powder (yield 43%). The synthesis scheme of Step 4 is shown in (d-2).

Incidentally, showing nuclear magnetic resonance spectroscopy of the yellow powder obtained in Step 4 the analysis result by ^{(1 H-NMR)} is shown below. In addition, a ¹ H-NMR chart is shown in FIG. From this, it was found that the organometallic complex [Ir (iBudbtpm) ₃ ] of the present invention represented by the above-mentioned structural formula (200) was obtained in this synthesis example.

¹ H-NMR. δ (CD ₂ Cl ₂ ): 0.96 (t, 18 H), 2.13-2.18 (m, 3 H), 2.69 (d, 6 H), 7.23 (s, 3 H), 7. 36 (t, 3 H), 7.41 (t, 3 H), 7.69 (d, 3 H), 7.87 (s, 3 H), 8. 18 (d, 3 H), 8. 28 (s, 3 H) ), 8.61 (s, 3H).

Next, an ultraviolet-visible absorption spectrum (hereinafter simply referred to as “absorption spectrum”) and an emission spectrum of a dichloromethane solution of [Ir (iBudbtpm) ₃ ] were measured. For measurement of the absorption spectrum, a dichloromethane solution (0.061 mmol / L) was put in a quartz cell using an ultraviolet-visible spectrophotometer (V550 type manufactured by JASCO Corporation), and the measurement was performed at room temperature. In addition, for measurement of the emission spectrum, the degassed dichloromethane solution (0.061 mmol / L) was put in a quartz cell using a fluorometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.), and the measurement was performed at room temperature. The measurement results of the obtained absorption spectrum and emission spectrum are shown in FIG. The absorption spectrum shown in FIG. 17 shows the result of subtracting the absorption spectrum measured by putting only dichloromethane into the quartz cell from the measured absorption spectrum.

As shown in FIG. 17, the organometallic complex [Ir (iBudbtpm) ₃ ] of the present invention has a light emission peak at 538 nm, and green light emission is observed from the dichloromethane solution.

Next, [Ir (iBudbtpm) ₃ ] obtained in this example was analyzed by liquid chromatography mass spectrometry (abbreviation: LC / MS analysis).

LC / MS analysis was carried out by LC (liquid chromatography) separation by Acquity UPLC manufactured by Waters, and MS analysis (mass spectrometry) by Xevo G2 Tof MS manufactured by Waters. The column used for LC separation was Acquity UPLC BEH C8 (2.1 × 100 mm 1.7 μm), and the column temperature was 40 ° C. Mobile phase A was acetonitrile, and mobile phase B was 0.1% aqueous solution of formic acid. The sample was prepared by dissolving [Ir (iBudbtpm) ₃ ] of any concentration in chloroform and diluting with acetonitrile to make the injection volume 5.0 μL.

  For LC separation, use a gradient method that changes the composition of the mobile phase, and from 0 minutes to 1 minute after the start of measurement, mobile phase A: mobile phase B = 75:25, and then change the composition. And the ratio of the mobile phase B to the mobile phase B was 95: 5. The composition was varied linearly.

  In MS analysis, ionization was performed by electrospray ionization (abbr .: ESI), capillary voltage was 3.0 kV, sample cone voltage was 30 V, and detection was performed in positive mode. The mass range to be measured was m / z 100 to 1300.

  Under the above conditions, the separated and ionized components of m / z = 1145.31 collide with argon gas in a collision cell to dissociate into product ions. The energy (collision energy) at the time of collision with argon was 70 eV. The results of detection of the dissociated product ions by time of flight (TOF) MS are shown in FIG.

From the results in FIG. 18, the organometallic complex which is one embodiment of the present invention, which is represented by a structural formula (200), [Ir (iBudbtpm) ₃ ] mainly has m / z = 825.17 and m / z = 507. It was found that product ions were detected around .05, m / z = 319.13 and m / z = 276.07. Incidentally, the results shown in FIG. 18, since shows the characteristic results from a [Ir _{(iBudbtpm) 3],} important in identifying contained in the mixture [Ir _{(iBudbtpm) 3]} Data.

The product ion in the vicinity of m / z = 825.17 is derived from the cation of the compound of the structural formula (200) in a state where one molecule and a proton are separated in the ligand HiBudbtpm, and m / z = around 50.05 The product ion is estimated to be derived from a cation in a state where one additional molecule HiBudbtpm from the product ion near m / z = 825.17 is separated, which is one of the features of the organometallic complex which is one embodiment of the present invention It is one. Also, the product ion in the vicinity of m / z = 319.13 is presumed to be a cation in a state in which a proton is added to the ligand HiBudbtpm. In addition, the product ion in the vicinity of m / z = 275.06 is presumed to be the removal of a propyl group from the product ion in the vicinity of m / z = 319.13, and the organometallic complex [Ir ( It is suggested that iBudbtpm) ₃ ] contains a propyl group.

In this example, the synthesis of tris {2- [6- (2-methylpropyl) -4-pyrimidinyl-κN3] dibenzofuran-3-yl-κC} iridium (III) (abbreviation: [Ir (iBudbfpm) ₃ ]) The method will be described. The structural formula of [Ir (iBudbfpm) ₃ ] is shown below.

Step 1: Synthesis of 4-chloro-6- (2-methylpropyl) pyrimidine
It synthesize | combined similarly to the step 1 of the synthesis example 1.

<Step 2; Synthesis of 4- (dibenzofuran-2-yl) -6- (2-methylpropyl) pyrimidine (abbreviation: HiBudbfpm)>
It synthesize | combined similarly to the step 2 of the synthesis example 1.

<Step 3; Di-μ-chloro-tetrakis {2- [6- (2-methylpropyl) -4-pyrimidinyl-κN3] dibenzofuran-3-yl-κC} diiridium (III) (abbreviation: [Ir (iBudbfpm) )) ₂ Cl] ₂ ) synthesis>
It synthesize | combined similarly to the step 3 of the synthesis example 1.
<Step 4; Synthesis of tris {2- [6- (2-methylpropyl) -4-pyrimidinyl-κN3] dibenzofuran-3-yl-κC} iridium (III) (abbreviation: [Ir (iBudbfpm) ₃ ]>
9 g of phenol, 1.28 g of [Ir (iBudbfpm) ₂ Cl] ₂ , 1.36 g of HiBudbfpm, 1.13 g of potassium carbonate were placed in a 200 mL three-necked flask equipped with a reflux condenser, and the inside of the flask was purged with nitrogen. Then, it heated at 195 degreeC for 7 hours, and was made to react. The resulting mixture was suction filtered with methanol, washed with water and methanol. The obtained solid is purified by flash column chromatography using dichloromethane: ethyl acetate = 10: 1 (volume ratio) as a developing solvent, and recrystallized with a mixed solvent of dichloromethane and methanol to obtain [Ir (iBudbfpm) ₃ ] was obtained as a yellow powder (yield 2%). The synthesis scheme of Step 4 is shown in (d-1) below.

Incidentally, showing nuclear magnetic resonance spectroscopy of the yellow powder obtained above analysis result by ^{(1 H-NMR)} is shown below. In addition, a ¹ H-NMR chart is shown in FIG. From this, it is understood that [Ir (iBudbfpm) ₃ ] represented by the above-mentioned structural formula (300) was obtained in this synthesis example.

¹ H-NMR. δ (CD ₂ Cl ₂ ): 0.95 (t, 18 H), 2.11-2.17 (m, 3 H), 2.68 (d, 6 H), 6.88 (s, 3 H), 7. 26-7.31 (m, 3H), 7.33-7.34 (s, 6H), 7.80 (s, 3H), 7.93 (d, 3H), 8.29 (s, 3H) , 8.46 (s, 3H).

Next, the UV-visible absorption spectrum and the emission spectrum of a dichloromethane solution of [Ir (iBudbfpm) ₃ ] were measured. For measurement of the absorption spectrum, a dichloromethane solution (0.027 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, the degassed dichloromethane solution (0.027 mmol / L) was put in a quartz cell using a fluorometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.), and measurement was performed at room temperature. The measurement results of the obtained absorption spectrum and emission spectrum are shown in FIG. The absorption spectrum shown in FIG. 20 shows the result of subtracting the absorption spectrum measured by putting only dichloromethane into the quartz cell from the measured absorption spectrum.

As shown in FIG. 20, [Ir (iBudbfpm) ₃ ] has a light emission peak at 529 nm, and green light emission was observed from the dichloromethane solution.

Next, [Ir (iBudbfpm) ₃ ] obtained in this example was analyzed by liquid chromatography mass spectrometry (abbreviation: LC / MS analysis).

LC / MS analysis was carried out by LC (liquid chromatography) separation by Acquity UPLC manufactured by Waters, and MS analysis (mass spectrometry) by Xevo G2 Tof MS manufactured by Waters. The column used for LC separation was Acquity UPLC BEH C8 (2.1 × 100 mm 1.7 μm), and the column temperature was 40 ° C. Mobile phase A was acetonitrile, and mobile phase B was 0.1% aqueous solution of formic acid. In addition, the sample was prepared by dissolving [Ir (iBudbfpm) ₃ ] of any concentration in chloroform and diluting with acetonitrile to make the injection volume 5.0 μL.

  For LC separation, a gradient method that changes the composition of the mobile phase is used, and from 0 minutes to 1 minute after the start of measurement, mobile phase A: mobile phase B = 65: 35, and then change the composition. The ratio of A to B was 90 to 10 for mobile phase A, and the mobile phase B was 95 for 5 minutes at 10 minutes. The composition change was changed linearly.

  In MS analysis, ionization was performed by electrospray ionization (abbr .: ESI), capillary voltage was 3.0 kV, sample cone voltage was 30 V, and detection was performed in positive mode. The mass range to be measured was m / z 100 to 1300.

  Under the above conditions, the separated and ionized components of m / z = 1097.37 collide with argon gas in a collision cell to dissociate them into product ions. The energy (collision energy) at the time of collision with argon was 70 eV. The results of detection of the dissociated product ions by time of flight (TOF) MS are shown in FIG.

From the results in FIG. 21, the organometallic complex which is one embodiment of the present invention, which is represented by the structural formula (300), [Ir (iBudbfpm) ₃ ] is mainly around m / z = 793.22, m / z = 489 It was found that product ions were detected around .07, m / z = 303.15, m / z = 295.09 and m / z = 260.09. Incidentally, the results shown in FIG. 21, since shows the characteristic results from a [Ir _{(iBudbfpm) 3],} important in identifying contained in the mixture [Ir _{(iBudbfpm) 3]} Data.

The product ion in the vicinity of m / z = 793.22 is derived from the cation of the compound of the structural formula (300) in which one molecule and a proton are separated in the ligand HiBudbfpm, and the m / z is around 48.07. Product ion is estimated to be derived from a cation in a state where one additional molecule HiBedbbfpm from the product ion near m / z = 793.22 is separated, which is one of the features of the organometallic complex according to an aspect of the present invention It is. Also, the product ion near m / z = 303.15 is presumed to be a cation in a state in which a proton is added to the ligand HiBudbfpm. In addition, the product ion in the vicinity of m / z = 260.09 is estimated to be the removal of a propyl group from the product ion in the vicinity of m / z = 303.15, and the organometallic complex [Ir ( It is suggested that iBudbfpm ₃ ] contains a propyl group.

In this example, a light-emitting element (light-emitting element 1) of one embodiment of the present invention will be described. Structural formulas of organic compounds used in the light-emitting element 1 are shown below.

(Method for Manufacturing Light-Emitting Element 1)
First, indium tin oxide (ITSO) containing silicon oxide was deposited over a glass substrate by a sputtering method to form a first electrode 101. The film thickness was 110 nm, and the electrode area was 2 mm × 2 mm. Here, the first electrode 101 is an electrode which functions as an anode of the light-emitting element.

Next, as pretreatment for forming a light-emitting element over the substrate, the substrate surface was washed with water and baked at 200 ° C. for 1 hour, and then UV ozone treatment was performed 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 substrate on which the first electrode 101 is formed is fixed to a substrate holder provided in a vacuum vapor deposition apparatus so that the surface on which the first electrode 101 is formed is downward, and it is about 10 ⁻⁴ Pa After reducing the pressure down to 4,4 ′, 4 ′ ′-(benzene-1,3,5-triyl represented by the above structural formula (i) by vapor deposition using resistance heating on the first electrode 101 The hole injection layer 111 was formed by co-evaporation of tri) (dibenzothiophene) (abbreviation: DBT3P-II) and molybdenum (VI) oxide. The film thickness was 20 nm, and the weight ratio of DBT3P-II to molybdenum oxide was adjusted to be 4: 2 (= DBT3P-II: molybdenum oxide).

Next, a film of 20 nm of 4-phenyl-4 ′-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: BPAFLP) represented by the above structural formula (ii) is formed on the hole injection layer 111. The film was formed to have a thickness to form a hole transport layer 112.

Furthermore, on the hole transporting layer 112, 2- [3 ′-(dibenzothiophen-4-yl) biphenyl-3-yl] dibenzo [f, h] quinoxaline represented by the above structural formula (iii) (abbreviation: 2mDBTBPDB q-II), N- (1,1'-biphenyl-4-yl) -9,9-dimethyl-N- [4- (9-phenyl-9H-carbazole-) represented by the above structural formula (iv) 3-yl) phenyl] -9H-fluoren-2-amine (abbreviation: PCBBiF) and bis {2- [6- (2-methylpropyl) -4-pyrimidinyl-κN3] represented by the above structural formula (v) Dibenzofuran-3-yl-κC} (2,4-pentanedionato-κ ² O, O ′) iridium (III) (abbreviation: [Ir (iBudbfpm) ₂ (acac)]) in a weight ratio of 0.8: 0.2: 0. A light emitting layer 113 was formed by co-evaporation to a thickness of 40 nm so as to be 05 (= 2 m DBTBP DB q-II: PCBBiF: [Ir (iBudbfpm) ₂ (acac)]).

Subsequently, 2mDBTBPDBq-II is formed to have a thickness of 20 nm on the light emitting layer 113, and then, bathosophenanthroline (abbreviation: Bphen) represented by the above structural formula (vi) is formed to have a thickness of 10 nm. Thus, the electron transport layer 114 was formed.

After the electron transporting layer 114 is formed, lithium fluoride (LiF) is deposited to a thickness of 1 nm to form an electron injecting layer 115. Finally, as a second electrode 102 which functions as a cathode, Aluminum was vapor-deposited to a film thickness of 200 nm to fabricate a light-emitting element 1 of this example.

The table | surface which put together the element structure of the light emitting element 1 is shown.

Sealing the light-emitting element 1 with a glass substrate so that the light-emitting element is not exposed to the atmosphere in a glove box under a nitrogen atmosphere (a sealing material is applied around the element, and UV treatment is performed at 80.degree. After heat treatment was performed for 1 hour, measurement was performed on initial characteristics. The measurement was performed at room temperature (in the atmosphere kept at 25 ° C.).

The luminance-current efficiency characteristics of the light-emitting element 1 are illustrated in FIG. 22, the voltage-luminance characteristics are illustrated in FIG. 23, the voltage-current characteristics are illustrated in FIG. 24, and the emission spectrum is illustrated in FIG. From the above results, it was found that Light-emitting Element 1 exhibited excellent characteristics.

In this example, the light-emitting element (the light-emitting element 2 and the light-emitting element 3) of one embodiment of the present invention will be described. Structural formulas of organic compounds used in the light-emitting element 2 and the light-emitting element 3 are shown below.

(Method for Manufacturing Light-Emitting Element 2)
First, indium tin oxide (ITSO) containing silicon oxide was deposited over a glass substrate by a sputtering method to form a first electrode 101. The film thickness was 110 nm, and the electrode area was 2 mm × 2 mm. Here, the first electrode 101 is an electrode which functions as an anode of the light-emitting element.

Next, as pretreatment for forming a light-emitting element over the substrate, the substrate surface was washed with water and baked at 200 ° C. for 1 hour, and then UV ozone treatment was performed 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 substrate on which the first electrode 101 is formed is fixed to a substrate holder provided in a vacuum vapor deposition apparatus so that the surface on which the first electrode 101 is formed is downward, and it is about 10 ⁻⁴ Pa After reducing the pressure down to 4,4 ′, 4 ′ ′-(benzene-1,3,5-triyl represented by the above structural formula (i) by vapor deposition using resistance heating on the first electrode 101 The hole injection layer 111 was formed by co-evaporation of tri) (dibenzothiophene) (abbreviation: DBT3P-II) and molybdenum (VI) oxide. The film thickness was 20 nm, and the weight ratio of DBT3P-II to molybdenum oxide was adjusted to be 4: 2 (= DBT3P-II: molybdenum oxide).

Next, a film of 20 nm of 4-phenyl-4 ′-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: BPAFLP) represented by the above structural formula (ii) is formed on the hole injection layer 111. The film was formed to have a thickness to form a hole transport layer 112.

Furthermore, on the hole transporting layer 112, 2- [3 ′-(dibenzothiophen-4-yl) biphenyl-3-yl] dibenzo [f, h] quinoxaline represented by the above structural formula (iii) (abbreviation: 2mDBTBPDB q-II), N- (1,1'-biphenyl-4-yl) -9,9-dimethyl-N- [4- (9-phenyl-9H-carbazole-) represented by the above structural formula (iv) 3-yl) phenyl] -9H-fluoren-2-amine (abbreviation: PCBBiF) and tris {2- [6- (2-methylpropyl) -4-pyrimidinyl-κN3] represented by the above structural formula (vii) dibenzothiophene-3-yl-KC} iridium (III (abbreviation: [Ir _(iBudbtpm) 3] a) a weight ratio of 0.8: 0.2: 0.05 (= 2mDBTBPDBq -II: PCBB F: it was formed [Ir _{(iBudbtpm) 3])} and the light-emitting layer 113 was deposited 40nm co so.

Subsequently, 2mDBTBPDBq-II is formed to have a thickness of 20 nm on the light emitting layer 113, and then, bathosophenanthroline (abbreviation: Bphen) represented by the above structural formula (vi) is formed to have a thickness of 10 nm. Thus, the electron transport layer 114 was formed.

After the electron transporting layer 114 is formed, lithium fluoride (LiF) is deposited to a thickness of 1 nm to form an electron injecting layer 115. Finally, as a second electrode 102 which functions as a cathode, Aluminum was vapor-deposited to a film thickness of 200 nm to fabricate a light-emitting element 1 of this example.

(Method of Manufacturing Light-Emitting Element 3)
The light-emitting element 3 has tris {2- [6- (2-methylpropyl) -4-pyrimidinyl-κN ₃ represented by the above structural formula (v) in [Ir (iBudbtpm) ₃ ] in the light emitting layer of the light emitting element 2 Except that it was changed to dibenzofuran-3-yl- イ リ ジ ウ ム C iridium (III) (abbreviation: [Ir (iBudbfpm) ₃ ]), it was manufactured similarly to the light emitting element 2.

The table | surface which put together the element structure of the light emitting element 2 and the light emitting element 3 is shown.

An operation of sealing the light emitting element 2 and the light emitting element 3 with a glass substrate so that the light emitting element is not exposed to the atmosphere in a glove box under a nitrogen atmosphere (a sealing material is applied around the element, UV treatment at the time of sealing, After heat treatment at 80 ° C. for 1 hour, measurement of initial characteristics was performed. The measurement was performed at room temperature (in the atmosphere kept at 25 ° C.).

The luminance-current efficiency characteristics of the light-emitting elements 2 and 3 are shown in FIG. 26, the voltage-luminance characteristics are shown in FIG. 27, the voltage-current characteristics are shown in FIG. 28, and the emission spectrum is shown in FIG. From the above results, it was found that Light-emitting Element 2 and Light-emitting Element 3 exhibited favorable characteristics.

101 First electrode 102 Second electrode 103 EL layer 111 Hole injection layer 112 Hole transport layer 113 Light emitting layer 114 Electron transport layer 115 Electron injection layer 400 Substrate 401 First electrode 403 EL layer 404 Second electrode 405 Sealing material 406 Sealing material 407 Sealing substrate 412 Pad 420 IC chip 501 First electrode 502 Second electrode 503 EL layer 511 First light emitting unit 512 Second light emitting unit 513 Charge generation layer 601 Driving circuit portion (source line Drive circuit)
602 pixel portion 603 driver circuit portion (gate line driver circuit)
604 sealing substrate 605 sealing material 607 space 608 wiring 609 FPC (flexible printed circuit)
610 element substrate 611 FET for switching
612 FET for current control
613 first electrode 614 insulator 616 EL layer 617 second electrode 618 light emitting element 623 n channel type FET
624 p-channel FET
901 housing 902 liquid crystal layer 903 backlight unit 904 housing 905 driver IC
906 terminal 951 substrate 952 electrode 953 insulating layer 954 partition layer 955 EL layer 956 electrode 1001 substrate 1002 base insulating film 1003 gate insulating film 1006 gate electrode 1007 gate electrode 1008 gate electrode 1020 first interlayer insulating film 1021 second interlayer insulating film 1022 electrode 1024 W first electrode of light emitting element 1024 R first electrode of light emitting element 1024 G first electrode of light emitting element 1024 B first electrode of light emitting element 1025 partition wall 1028 EL layer 1029 second electrode of light emitting element 1031 sealing Substrate 1032 Sealing material 1033 Transparent base 1034R Red colored layer 1034G Green colored layer 1034B Blue colored layer 1035 Black layer (black matrix)
1037 third interlayer insulating film 1040 pixel portion 1041 drive circuit portion 1042 peripheral portion 2001 housing 2002 light source 3001 lighting device 5000 display area 5001 display area 5002 display area 5003 display area 5004 display area 5005 display area 7101 housing 7103 display area 7105 Stand 7107 Display unit 7109 Operation key 7110 Remote controller 7201 Main unit 7202 Case 7203 Display unit 7204 Keyboard 7205 External connection port 7206 Pointing device 7210 Second display unit 7401 Case 7402 Display unit 7403 Operation button 7404 External connection port 7405 Speaker 7406 Microphone 9033 Fastener 9034 Switch 9035 Power switch 9036 Switch 9038 Operation switch 9630 Case 9631 Display 96 1a display unit 9631b display unit 9632a touch region 9632b panel region 9633 a solar cell 9634 charge and discharge control circuit 9635 battery 9636 DCDC converter 9637 operating keys 9638 Converter 9639 button

Claims (18)

An organometallic complex having a pyrimidine ring,
It has a dibenzothiophene skeleton or a dibenzofuran skeleton at the 4-position of the pyrimidine ring,
The nitrogen at position 3 of the pyrimidine ring coordinates to a metal,
A light emitting device having an organometallic complex, which is characterized in that the dibenzothiophene skeleton or the dibenzofuran skeleton is bonded to the metal, as a light emission center. In claim 1,
The light-emitting element, wherein the metal is a group 9 element or a group 10 element. In claim 1 or claim 2,
The light-emitting element, wherein the metal is iridium. An organometallic complex including a structure represented by General Formula (G0-1).

(Wherein, R ¹ represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. R ^{2 to} R ⁹ represent hydrogen or an alkyl group having 1 to 6 carbon atoms) And M represents a metal of a Group 9 element or a Group 10 element, and X represents an oxygen atom or a sulfur atom. An organometallic complex represented by a general formula (G0-2).

(Wherein, R ¹ represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. R ^{2 to} R ⁹ represent hydrogen or an alkyl group having 1 to 6 carbon atoms) M represents a metal of a Group 9 element or a Group 10 element, n represents 3 when M is a Group 9 element, and n represents a group 10 element And X represents an oxygen atom or a sulfur atom.) An organometallic complex represented by a general formula (G0-3).

(Wherein, R ¹ represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. R ^{2 to} R ⁹ represent hydrogen or an alkyl group having 1 to 6 carbon atoms) M represents a metal of a Group 9 element or a Group 10 element, m is 2 when M is a Group 9 element, and 1 when M is a Group 10 element. And L represents a monoanionic ligand, and X represents an oxygen atom or a sulfur atom. In claim 6,
The monoanionic ligand is a monoanionic bidentate chelating ligand having a beta diketone structure, a monoanionic bidentate chelating ligand having a carboxyl group, a monoanionic difunctional one having a phenolic hydroxyl group. 5 or 6 member containing N atom coordinated by a carbon atom that forms a metal _- carbon bond, or a monoanionic bidentate chelate ligand in which both coordination elements are nitrogen An organometallic complex which is any of monoanionic ligands forming a metallacycle. In claim 6 or claim 7,
An organometallic complex in which the monoanionic ligand is any one of formulas (L1) to (L7).

(Wherein, R ^{71 to} R ¹⁰⁹ each independently represent hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a halogen group, a vinyl group, or a substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms Or a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, and each of A ^{1 to} A ³ independently represents a bond to nitrogen or hydrogen. sp ² hybridized represent carbon, or a sp ² carbon bonded to a substituent R is the substituent R represents an alkyl group, a halogen group, a haloalkyl group having 1 to 6 carbon atoms or a phenyl group, having 1 to 6 carbon atoms .) An organometallic complex represented by General Formula (G1-1).

(Wherein, R ¹ represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. R ^{2 to} R ⁹ represent hydrogen or an alkyl group having 1 to 6 carbon atoms) And X represents an oxygen atom or a sulfur atom.) An organometallic complex represented by General Formula (G1-2).

(Wherein, R ¹ represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. R ^{2 to} R ⁹ represent hydrogen or an alkyl group having 1 to 6 carbon atoms) And X represents an oxygen atom or a sulfur atom.) The organometallic complex according to any one of claims 4 to 10, wherein R ¹ is either an alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted phenyl group. An organometallic complex according to any one of claims 4 to 10, wherein R ¹ is any of a C 4 to C 6 alkyl group. An organometallic complex according to any one of claims 4 to 12, wherein X is a sulfur atom. An organometallic complex according to any one of claims 4 to 12, wherein X is an oxygen atom. A light emitting device using the organometallic complex according to any one of claims 2 to 14. A light emitting element according to any one of claims 1 to 3 or 15;
A transistor or a substrate,
A light emitting device having A light emitting device according to claim 16;
Sensor, operation button, speaker or microphone,
Electronic equipment having. A light emitting device according to claim 16;
And
A lighting device having