Organic compound, light-emitting device, and display device

Abstract

Provided is a novel organic compound that is exceptional in terms of convenience, usability, and reliability. An organic compound represented by general formula (G0). In general formula (G0), X is a nitrogen atom or a carbon atom; when X is a carbon atom, X bonds with hydrogen or a substituent; one of R104 and R105 is a cyano group; at least one of R102 and R107 is a C1-6 alkyl group; and each of the rest of R101 to R111 independently is hydrogen or a substituent. Each of the substituents independently is a C1-6 alkyl group, a C3-7 cycloalkyl group, a substituted or unsubstituted C6-13 aryl group, a substituted or unsubstituted C1-5 heteroaryl group, an amino group, or a hydroxy group. Additionally, the substituents may bond to each other to form a ring. Also, n is an integer of 1 to 3, and L is a ligand.

Description

Organic compounds, light-emitting devices, display devices

[0001] One embodiment of the present invention relates to an organic compound, a light-emitting device, a display device, an electronic device, a light-emitting device, a lighting device, or a semiconductor device.

[0002] 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 this specification and the like relates to an object, a method, or a manufacturing method. Alternatively, one embodiment of the present invention relates to a process, a machine, manufacture, or a composition of matter. Therefore, more specifically, examples of the technical field of one embodiment of the present invention disclosed in this specification include a semiconductor device, a display device, a light-emitting device, a power storage device, a memory device, a driving method thereof, or a manufacturing method thereof.

[0003] For example, novel organic compounds containing twisted aryl groups are known. These organic compounds, in particular, contain 2-phenylpyridine ligands with twisted aryl groups at the pyridine moiety of the ligand. These compounds can be used, in particular, as luminescent dopants in organic light-emitting devices (Patent Document 1).

[0004] WO2010 / 028151

[0005] An object of one embodiment of the present invention is to provide a novel organic compound with excellent convenience, usefulness, or reliability. Another object is to provide a novel light-emitting device with excellent convenience, usefulness, or reliability. Another object is to provide a novel display device with excellent convenience, usefulness, or reliability. Another object is to provide a novel electronic device with excellent convenience, usefulness, or reliability. Another object is to provide a novel light-emitting device with excellent convenience, usefulness, or reliability. Another object is to provide a novel lighting device with excellent convenience, usefulness, or reliability. Another object is to provide a novel organic compound, a novel light-emitting device, a novel display device, a novel electronic device, a novel light-emitting device, a novel lighting device, or a novel semiconductor device.

[0006] Note that the description of these problems does not preclude the existence of other problems. Note that one embodiment of the present invention does not necessarily solve all of these problems. Note that problems other than these will become apparent from the description of the specification, drawings, claims, etc., and it is possible to extract other problems from the description of the specification, drawings, claims, etc.

[0007] (1) One embodiment of the present invention is an organic compound represented by General Formula (G0).

[0008]

[0009] In general formula (G0), X represents a nitrogen atom or a carbon atom, and when X represents a carbon atom, X is bonded to a hydrogen atom or a substituent.

[0010] Also, R １０４ and R １０５ is a cyano group, and R １０２ and R １０７ At least one of R is an alkyl group having 1 to 6 carbon atoms; １０１ ~R １１１ The others are each independently hydrogen or a substituent.

[0011] The above-mentioned substituents are each independently an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 5 carbon atoms, an amino group, or a hydroxy group, and may be bonded to each other to form a ring.

[0012] n is an integer of 1 or more and 3 or less, and L is a ligand represented by structural formula (L0).

[0013]

[0014] In structural formula (L0), R ２０１ ~R ２０８ are each independently a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and in general formula (G0), all of the hydrogen atoms may be deuterium atoms.

[0015] As a result, the cyano group introduced into the phenyl group can stabilize the bond energy within the molecule, thereby improving the thermal properties. Furthermore, the cyano group introduced into the phenyl group can stabilize the energy of the molecular orbital, thereby adjusting the emission wavelength. As a result, a novel organic compound with excellent convenience, usefulness, and reliability can be provided.

[0016] (2) Another embodiment of the present invention is an organic compound represented by General Formula (G1).

[0017]

[0018] In general formula (G1), X represents a nitrogen atom or a carbon atom, and when X represents a carbon atom, X is bonded to a hydrogen atom or a substituent.

[0019] Also, R １０２ and R １０７ At least one of R is an alkyl group having 1 to 6 carbon atoms; １０１ ~R １１１ The others are each independently hydrogen or a substituent.

[0020] The above-mentioned substituents are each independently an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 5 carbon atoms, an amino group, or a hydroxy group, and may be bonded to each other to form a ring.

[0021] n is an integer of 1 or more and 3 or less, and L is a ligand represented by structural formula (L1).

[0022]

[0023] In structural formula (L1), R ２０１ ~R ２０８ are each independently a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and in general formula (G1), all of the hydrogen atoms may be deuterium atoms.

[0024] In the organic compound represented by general formula (G1) having the above structure, R １０２ or R １０７The cyano group induces a steric hindrance effect between the phenyl group having the cyano group introduced therein and the phenylpyridine skeleton having the iridium coordinated thereto. This suppresses free rotation of the phenyl group having the cyano group introduced therein, improving the thermal properties of the compound, for example, suppressing thermal decomposition, and suppressing decomposition due to high-temperature heating during the synthesis reaction, thereby improving the synthesis yield. It also improves sublimability, i.e., sublimation without thermal decomposition. It also exhibits resistance to use in high-temperature environments. Furthermore, the twist occurring between the phenyl group having the cyano group introduced therein and the phenylpyridine skeleton having the iridium coordinated thereto shortens the emission wavelength. It also achieves high luminous efficiency. As a result, it is possible to provide a novel organic compound that is highly convenient, useful, and reliable.

[0025] (3) Another embodiment of the present invention is an organic compound represented by General Formula (G2).

[0026]

[0027] However, in general formula (G2), R １０２ and R １０７ At least one of R is an alkyl group having 1 to 6 carbon atoms; １０２ ~R １１２ The others are each independently hydrogen or a substituent.

[0028] The above-mentioned substituents are each independently an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 5 carbon atoms, an amino group, or a hydroxy group, and may be bonded to each other to form a ring.

[0029] In addition, in the general formula (G2), all of the hydrogen atoms may be deuterium atoms.

[0030] This allows the synthesis steps to be shortened and the yield to be improved. In addition, molecular orientation can be easily achieved, improving the luminous efficiency. As a result, a novel organic compound with excellent convenience, usefulness, and reliability can be provided.

[0031] (4) Another embodiment of the present invention is an organic compound represented by General Formula (G3).

[0032]

[0033] However, in general formula (G3), R １０２ and R １０７ At least one of R is an alkyl group having 1 to 6 carbon atoms; １０２ ~R １１２ The others are each independently hydrogen or a substituent.

[0034] The above-mentioned substituents are each independently an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 5 carbon atoms, an amino group, or a hydroxy group, and may be bonded to each other to form a ring.

[0035] In addition, in the general formula (G3), all of the hydrogen atoms may be deuterium atoms.

[0036] This can improve the synthesis yield, and as a result, it is possible to provide novel organic compounds that are highly convenient, useful, and reliable.

[0037] (5) Another embodiment of the present invention is an organic compound represented by General Formula (G4).

[0038]

[0039] However, in general formula (G4), R １０２ and R １０７ At least one of R is an alkyl group having 1 to 6 carbon atoms; １０２ ~R １０７ The others are each independently hydrogen or a substituent.

[0040] The above-mentioned substituents are each independently an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 5 carbon atoms, an amino group, or a hydroxy group, and may be bonded to each other to form a ring.

[0041] In addition, in the general formula (G4), all of the hydrogen atoms may be deuterium atoms.

[0042] This makes it possible to improve the thermal stability even in a homoleptic structure, thereby providing a novel organic compound that is highly convenient, useful, and reliable.

[0043] (6) Another embodiment of the present invention is a light-emitting device including a first electrode, a second electrode, and a first unit. The first unit is sandwiched between the first electrode and the second electrode and includes any of the above organic compounds.

[0044] As a result, the first unit includes the organic compound of one embodiment of the present invention. Furthermore, since the emission spectrum of the organic compound of one embodiment of the present invention includes light with a wavelength shorter than 500 nm, when the organic compound is used together with a fluorescent light-emitting material, energy can be efficiently transferred to the fluorescent light-emitting material. Furthermore, the phenomenon in which the luminance of the light-emitting device decreases with use can be suppressed. Furthermore, the reliability of the light-emitting device can be improved. Furthermore, the reliability of the light-emitting device can be improved, particularly at temperatures higher than room temperature. As a result, a novel light-emitting device with excellent convenience, usefulness, and reliability can be provided.

[0045] (7) Another embodiment of the present invention is a display device including a first light-emitting device and a second light-emitting device.

[0046] The first light-emitting device comprises a third electrode, a fourth electrode, a second unit, and a first layer, wherein the second unit is sandwiched between the third electrode and the fourth electrode, and the first layer is sandwiched between the second unit and the third electrode.

[0047] The second unit includes the organic compound described above, and the first layer includes a second organic compound including a halogen group or a cyano group, or a transition metal oxide.

[0048] The second light-emitting device is adjacent to the first light-emitting device, and the second light-emitting device includes a fifth electrode, a sixth electrode, a third unit, and a second layer. The fifth electrode has a gap between it and the third electrode. The third unit is sandwiched between the sixth electrode and the fifth electrode, and the third unit includes a light-emitting material. The second layer is sandwiched between the third unit and the fifth electrode.

[0049] The second layer includes a second organic compound or a transition metal oxide, and the second layer has a region between it and the first layer that is thinner than the first layer, and the region overlaps the gap.

[0050] This can suppress, for example, the current flowing through a thin film region. It can also suppress the current flowing between the first layer and the second layer. It can also suppress the phenomenon in which the adjacent second light-emitting device unintentionally emits light due to the operation of the first light-emitting device. As a result, a novel display device with excellent convenience, usefulness, and reliability can be provided.

[0051] (8) Another embodiment of the present invention is a display device including a first functional layer and a second functional layer.

[0052] The first functional layer overlaps the second functional layer, the first functional layer including a first pixel circuit and a second pixel circuit, and the second functional layer including a first light-emitting device and a second light-emitting device.

[0053] The first light-emitting device includes a third electrode, a fourth electrode, and a second unit, the second unit being sandwiched between the third electrode and the fourth electrode, the second unit including the organic compound, and the third electrode electrically connected to the first pixel circuit.

[0054] The second light-emitting device includes a fifth electrode, a sixth electrode, and a third unit, the third unit being sandwiched between the fifth electrode and the sixth electrode, the fifth electrode being electrically connected to the second pixel circuit, and the sixth electrode being electrically connected to the fourth electrode.

[0055] In the drawings accompanying this specification, components are classified by function and shown as block diagrams that are independent of each other, but in reality, it is difficult to completely separate components by function, and one component may be involved in multiple functions.

[0056] In this specification, the term "light-emitting device" includes an image display device using a light-emitting device. The term "light-emitting device" may also include a module in which a connector, such as an anisotropic conductive film or a TCP (Tape Carrier Package), is attached to a light-emitting device, a module in which a printed wiring board is provided at the end of a TCP, or a module in which an IC (integrated circuit) is directly mounted on a light-emitting device using a COG (Chip On Glass) method. Furthermore, lighting fixtures and the like may have a light-emitting device.

[0057] According to one embodiment of the present invention, a novel organic compound with excellent convenience, usefulness, or reliability can be provided. Another embodiment of the present invention can provide a novel light-emitting device with excellent convenience, usefulness, or reliability. Another embodiment of the present invention can provide a novel display device with excellent convenience, usefulness, or reliability. Another embodiment of the present invention can provide a novel electronic device with excellent convenience, usefulness, or reliability. Another embodiment of the present invention can provide a novel light-emitting device with excellent convenience, usefulness, or reliability. Another embodiment of the present invention can provide a novel lighting device with excellent convenience, usefulness, or reliability. Another embodiment of the present invention can provide a novel organic compound. Another embodiment of the present invention can provide a novel light-emitting device. Another embodiment of the present invention can provide a novel display device. Another embodiment of the present invention can provide a novel electronic device. Another embodiment of the present invention can provide a novel light-emitting device. Another embodiment of the present invention can provide a novel lighting device.

[0058] Note that the description of these effects does not preclude the existence of other effects. Note that one embodiment of the present invention does not necessarily have all of these effects. Note that effects other than these will become apparent from the description in the specification, drawings, claims, etc., and it is possible to extract other effects from the description in the specification, drawings, claims, etc.

[0059] FIGS. 1A and 1B are diagrams illustrating a configuration of a light-emitting device according to an embodiment. FIGS. 2A and 2B are diagrams illustrating a configuration of a light-emitting device according to an embodiment. FIGS. 3A and 3B are diagrams illustrating a configuration of a display device according to an embodiment. FIGS. 4A and 4B are diagrams illustrating a configuration of a display device according to an embodiment. FIGS. 5A to 5C are diagrams illustrating a configuration of a device according to an embodiment. FIG. 6 is a diagram illustrating a configuration of a device according to an embodiment. FIGS. 7A and 7B are diagrams illustrating a configuration of a device according to an embodiment. FIGS. 8A and 8B are diagrams illustrating a configuration of an active matrix light-emitting device according to an embodiment. FIGS. 9A and 9B are diagrams illustrating a configuration of an active matrix light-emitting device according to an embodiment. FIG. 10 is a diagram illustrating a configuration of an active matrix light-emitting device according to an embodiment. FIGS. 11A and 11B are diagrams illustrating a configuration of a passive matrix light-emitting device according to an embodiment. FIGS. 12A and 12B are diagrams illustrating a configuration of a lighting device according to an embodiment. FIGS. 13A to 13D are diagrams illustrating a configuration of an electronic device according to an embodiment. FIGS. 14A to 14C are diagrams illustrating a configuration of an electronic device according to an embodiment. FIG. 15 is a diagram illustrating the configuration of an illumination device according to an embodiment. FIG. 16 is a diagram illustrating the configuration of an illumination device according to an embodiment. FIG. 17 is a diagram illustrating the configurations of an in-vehicle display device and an illumination device according to an embodiment. FIGS. 18A to 18C are diagrams illustrating the configuration of an electronic device according to an embodiment. FIG. 19 is a diagram illustrating a proton NMR spectrum of an organic compound according to an example. FIG. 20 is a diagram illustrating an absorption spectrum and an emission spectrum of an organic compound according to an example. FIG. 21 is a diagram illustrating a proton NMR spectrum of an organic compound according to an example. FIG. 22 is a diagram illustrating an absorption spectrum and an emission spectrum of an organic compound according to an example. FIG. 23 is a diagram illustrating a proton NMR spectrum of an organic compound according to an example. FIG. 24 is a diagram illustrating an absorption spectrum and an emission spectrum of an organic compound according to an example. FIG. 25 is a diagram illustrating a proton NMR spectrum of an organic compound according to an example.FIG. 26 is a diagram illustrating the absorption spectrum and emission spectrum of an organic compound according to an example. FIG. 27 is a diagram illustrating the configuration of a light-emitting device according to an example. FIG. 28 is a diagram illustrating the current density-luminance characteristics of a light-emitting device according to an example. FIG. 29 is a diagram illustrating the luminance-current efficiency characteristics of a light-emitting device according to an example. FIG. 30 is a diagram illustrating the voltage-luminance characteristics of a light-emitting device according to an example. FIG. 31 is a diagram illustrating the voltage-current characteristics of a light-emitting device according to an example. FIG. 32 is a diagram illustrating the luminance-external quantum efficiency characteristics of a light-emitting device according to an example. FIG. 33 is a diagram illustrating the emission spectrum of a light-emitting device according to an example. FIG. 34 is a diagram illustrating the change over time in normalized luminance of a light-emitting device according to an example.

[0060] An organic compound of one embodiment of the present invention is represented by a general formula (G0).

[0061]

[0062] In general formula (G0), X represents a nitrogen atom or a carbon atom, and when X represents a carbon atom, X is bonded to a hydrogen atom or a substituent. １０４ and R １０５ is a cyano group, and R １０２ and R １０７ At least one of R is an alkyl group having 1 to 6 carbon atoms; １０１ ~R １１１ and the other groups are each independently hydrogen or a substituent. The above substituents are each independently an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 5 carbon atoms, an amino group, or a hydroxy group, and may be bonded to each other to form a ring. n is an integer of 1 to 3, and L is a ligand.

[0063] This allows R １０２ or R １０７creates a steric hindrance effect between the phenyl group to which the cyano group has been introduced and the phenylpyridine skeleton to which iridium is coordinated. Furthermore, the free rotation of the phenyl group to which the cyano group has been introduced is suppressed, improving the thermal properties of the compound, such as suppressing thermal decomposition and decomposition due to high-temperature heating during the synthesis reaction, thereby improving the synthesis yield. Furthermore, the sublimability of the compound, which allows it to sublimate without thermal decomposition, can be improved. Furthermore, the compound can exhibit resistance to use in high-temperature environments. Furthermore, a twist occurs between the phenyl group to which the cyano group has been introduced and the phenylpyridine skeleton to which iridium is coordinated. Furthermore, the emission wavelength can be shortened. Furthermore, high luminous efficiency can be achieved. As a result, a novel organic compound with excellent convenience, usefulness, and reliability can be provided.

[0064] The embodiments will be described in detail with reference to the drawings. However, the present invention is not limited to the following description, and it will be readily understood by those skilled in the art that various changes in form and details can be made without departing from the spirit and scope of the present invention. Therefore, the present invention should not be interpreted as being limited to the description of the embodiments shown below. In the configuration of the invention described below, the same parts or parts having similar functions will be denoted by the same reference numerals in different drawings, and repeated explanations will be omitted.

[0065] Embodiment 1 In this embodiment, an organic compound of one embodiment of the present invention will be described.

[0066] <Example 1 of Organic Compound> An organic compound of one embodiment of the present invention described in this embodiment is represented by a general formula (G0).

[0067]

[0068] In general formula (G0), X represents a nitrogen atom or a carbon atom, and when X represents a carbon atom, X is bonded to hydrogen or a substituent.

[0069] R １０１ ~R １１１ Among them, R １０４ and R １０５ is a cyano group, and R １０２ and R １０７at least one of R is an alkyl group having 1 to 6 carbon atoms; １０１ ~R １１１ The others are each independently hydrogen or a substituent.

[0070] The hydrogen may be substituted with deuterium. Examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. Some or all of the hydrogen atoms in the alkyl group having 1 to 6 carbon atoms may be substituted with deuterium.

[0071] When X is a carbon atom, the substituent bonded to X and R １０１ ~R １１１ are each independently an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 5 carbon atoms, an amino group, or a hydroxy group. The above substituents may be bonded to each other to form a ring.

[0072] Examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group.

[0073] Examples of the cycloalkyl group having 3 to 7 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-methylcyclohexyl group, a 2,6-dimethylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, etc. When these groups have a substituent, examples of the substituent include an alkyl group having 1 to 6 carbon atoms and a phenyl group.

[0074] Examples of the aryl group having 6 to 13 carbon atoms include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a mesityl group, an o-biphenyl group, an m-biphenyl group, a p-biphenyl group, a 1-naphthyl group, a 2-naphthyl group, and a fluorenyl group. When these groups have a substituent, examples of the substituent include an alkyl group having 1 to 6 carbon atoms and a phenyl group.

[0075] Examples of the heteroaryl group having 1 to 5 carbon atoms include a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, etc. When these groups have a substituent, examples of the substituent include an alkyl group having 1 to 6 carbon atoms and a phenyl group.

[0076] Examples of the amino group include a methylamino group, an ethylamino group, an isopropylamino group, an isobutylamino group, a phenylamino group, and a 2,6-dimethylphenylamino group.

[0077] When X is a carbon atom, the substituent bonded to X and R １０１ ~R １１１ The above description of the substituents of the organic compound according to one embodiment of the present invention is used throughout this specification.

[0078] n is an integer of 1 or more and 3 or less, and L is a ligand represented by structural formula (L0).

[0079]

[0080] In the structural formula (L0), R ２０１ ~R ２０８are each independently hydrogen or an alkyl group having 1 to 6 carbon atoms. The hydrogen may be substituted with deuterium. Examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. Some or all of the hydrogen atoms in the alkyl group having 1 to 6 carbon atoms may be substituted with deuterium. When n is 1 or 2, for example, 2-phenylpyridine can be used as the ligand L.

[0081] In addition, in general formula (G0), all of the hydrogen atoms may be deuterium atoms.

[0082] Specific examples of organic compounds having the above structure are shown below.

[0083]

[0084] <Example 2 of Organic Compound> An organic compound of one embodiment of the present invention is represented by general formula (G1).

[0085]

[0086] In general formula (G1), X represents a nitrogen atom or a carbon atom, and when X represents a carbon atom, X is bonded to a hydrogen atom or a substituent.

[0087] R １０２ and R １０７ At least one of R is an alkyl group having 1 to 6 carbon atoms; １０１ ~R １１１ The other groups are each independently hydrogen or a substituent. The substituents may be bonded to each other to form a ring.

[0088] The substituents are each independently an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 5 carbon atoms, an amino group, or a hydroxy group.

[0089] n is an integer of 1 or more and 3 or less, and L is a ligand represented by structural formula (L1).

[0090]

[0091] However, in structural formula (L1), R ２０１ ~R ２０８ are each independently hydrogen or an alkyl group having 1 to 6 carbon atoms.

[0092] In addition, in the general formula (G1), all of the hydrogen atoms may be deuterium atoms.

[0093] This allows R １０２ or R １０７ creates a steric hindrance effect between the phenyl group to which the cyano group has been introduced and the phenylpyridine skeleton to which iridium is coordinated. Furthermore, by suppressing the free rotation of the phenyl group to which the cyano group has been introduced, the thermal properties of the compound can be improved, for example, by suppressing thermal decomposition, and decomposition due to high-temperature heating during the synthesis reaction can be suppressed, thereby improving the synthesis yield. Furthermore, sublimability, which allows the compound to sublimate without thermal decomposition, can be improved. Furthermore, durability in use in high-temperature environments can be achieved. Furthermore, a twist occurs between the phenyl group to which the cyano group has been introduced and the phenylpyridine skeleton to which iridium is coordinated. Furthermore, the emission wavelength can be shortened. Furthermore, high luminous efficiency can be achieved. As a result, a novel organic compound with excellent convenience, usefulness, and reliability can be provided.

[0094] Specific examples of organic compounds having the above structure are shown below.

[0095]

[0096] <Organic Compound Example 3> An organic compound of one embodiment of the present invention is represented by general formula (G2).

[0097]

[0098] However, in general formula (G2), R １０２ and R １０７ At least one of R is an alkyl group having 1 to 6 carbon atoms; １０２ ~R １１２ The other groups are each independently hydrogen or a substituent. The substituents may be bonded to each other to form a ring.

[0099] The substituents are each independently an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 5 carbon atoms, an amino group, or a hydroxy group.

[0100] In addition, in the general formula (G2), all of the hydrogen atoms may be deuterium atoms.

[0101] Specific examples of organic compounds having the above structure are shown below.

[0102]

[0103] <Organic Compound Example 4> An organic compound of one embodiment of the present invention is represented by general formula (G3).

[0104]

[0105] However, in general formula (G3), R １０２ and R １０７ At least one of R is an alkyl group having 1 to 6 carbon atoms; １０２ ~R １１２ The other groups are each independently hydrogen or a substituent. The substituents may be bonded to each other to form a ring.

[0106] The substituents are each independently an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 5 carbon atoms, an amino group, or a hydroxy group.

[0107] In addition, in the general formula (G3), all of the hydrogen atoms may be deuterium atoms.

[0108] Specific examples of organic compounds having the above structure are shown below.

[0109]

[0110]

[0111]

[0112]

[0113]

[0114] <Organic Compound Example 5> An organic compound of one embodiment of the present invention is represented by general formula (G4).

[0115]

[0116] However, in general formula (G4), R １０２ and R １０７ At least one of R is an alkyl group having 1 to 6 carbon atoms; １０２ ~R １０７ The other groups are each independently hydrogen or a substituent. The substituents may be bonded to each other to form a ring.

[0117] The substituents are each independently an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 5 carbon atoms, an amino group, or a hydroxy group.

[0118] In addition, in the general formula (G4), all of the hydrogen atoms may be deuterium atoms.

[0119] This makes it possible to improve the thermal stability even in a homoleptic structure, thereby providing a novel organic compound that is highly convenient, useful, and reliable.

[0120] Specific examples of organic compounds having the above structure are shown below.

[0121]

[0122] <Example of Synthesis Method of Organic Compound> A synthesis method of an organic compound of one embodiment of the present invention will be described. Note that the synthesis method is not limited to this. Synthesis can also be performed using other synthesis methods or known synthesis methods.

[0123] <<Method for Synthesizing Organic Compound Represented by General Formula (G0)>> The organic compound represented by the following general formula (G0) can be synthesized by the method shown in the following synthesis scheme (a).

[0124]

[0125] In general formula (G0), X represents a nitrogen atom or a carbon atom, and when X represents a carbon atom, X is bonded to a hydrogen atom or a substituent.

[0126] Also, R １０４ and R １０５ is a cyano group, and R １０２ and R １０７ At least one of R is an alkyl group having 1 to 6 carbon atoms; １０１ ~R １１１ The others are each independently hydrogen or a substituent.

[0127] The above-mentioned substituents are each independently an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 5 carbon atoms, an amino group, or a hydroxy group, and may be bonded to each other to form a ring.

[0128] Here, n is an integer of 1 or more and 3 or less, and L is a ligand represented by structural formula (L0).

[0129]

[0130] In the structural formula (L0), R ２０１ ~R ２０８ are each independently a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and in general formula (G0), all of the hydrogen atoms may be deuterium atoms.

[0131] For example, as shown in synthesis scheme (a), an organic compound represented by general formula (G0) can be synthesized by mixing a pyridine derivative represented by general formula (Gpy0) with a halogen-containing metal compound of iridium (iridium chloride hydrate, ammonium hexachloroiridate, etc.) or an organometallic complex compound of iridium (acetylacetonato complex, diethylsulfide complex, etc.), followed by heating.

[0132] In addition, an organic compound represented by general formula (G0) can also be synthesized by dissolving a pyridine derivative represented by general formula (Gpy0) and a halogen-containing iridium metal compound or an iridium organometallic complex compound in an alcohol solvent (glycerol, ethylene glycol, 2-methoxyethanol, 2-ethoxyethanol, etc.) and then heating the mixture.

[0133]

[0134] In the above synthesis scheme (a), X is a nitrogen atom or a carbon atom, and when X is a carbon atom, X is bonded to hydrogen or a substituent.

[0135] Also, R １０４ and R １０５ is a cyano group, and R １０２ and R １０７ At least one of R is an alkyl group having 1 to 6 carbon atoms; １０１ ~R １１１ The others are each independently hydrogen or a substituent.

[0136] The above-mentioned substituents are each independently an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 5 carbon atoms, an amino group, or a hydroxy group, and may be bonded to each other to form a ring.

[0137] n is an integer of 1 or more and 3 or less, and L is a ligand represented by structural formula (L0).

[0138]

[0139] In structural formula (L0), R ２０１ ~R ２０８ are each independently a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and in general formula (G0), all of the hydrogen atoms may be deuterium atoms.

[0140] Note that various types of the above-described compounds (Gpy0) and (L0) are commercially available or can be synthesized, and therefore, many types of pyridine derivatives represented by General Formula (G0) can be synthesized. Therefore, the organometallic complex of one embodiment of the present invention is characterized by a wide variety of ligands.

[0141] Note that this embodiment mode can be appropriately combined with other embodiment modes described in this specification.

[0142] Embodiment 2 In this embodiment, a structure of a light-emitting device 550X of one embodiment of the present invention will be described with reference to FIGS. 1A and 1B.

[0143] FIG. 1A is a cross-sectional view illustrating a structure of a light-emitting device according to one embodiment of the present invention, and FIG. 1B is a diagram illustrating energy levels of materials used in the light-emitting device according to one embodiment of the present invention.

[0144] <Configuration Example of Light-Emitting Device 550X> A light-emitting device 550X described in this embodiment includes an electrode 551X, an electrode 552X, and a unit 103X. The electrode 552X overlaps with the electrode 551X, and the unit 103X is sandwiched between the electrode 552X and the electrode 551X.

[0145] <Configuration Example of Unit 103X> The unit 103X has a single layer structure or a laminated structure. For example, the unit 103X has a layer 111X, a layer 112, and a layer 113 (see FIG. 1A). The unit 103X has a function of emitting light ELX.

[0146] Layer 111X is sandwiched between layer 113 and layer 112, layer 113 is sandwiched between electrode 552X and layer 111X, and layer 112 is sandwiched between layer 111X and electrode 551X.

[0147] For example, a layer selected from layers having a function such as a light-emitting layer, a hole-transporting layer, an electron-transporting layer, a carrier-blocking layer, etc. can be used for the unit 103X. Also, a layer selected from functional layers such as a hole-injecting layer, an electron-injecting layer, an exciton-blocking layer, and a charge-generating layer can be used for the unit 103X.

[0148] <<Structure Example of Layer 112>> For example, a material having a hole-transporting property can be used for the layer 112. The layer 112 can also be referred to as a hole-transporting layer. Note that a structure in which a material having a larger band gap than that of the light-emitting material contained in the layer 111X is used for the layer 112 is preferable. This can suppress energy transfer from excitons generated in the layer 111X to the layer 112.

[0149] [Material having hole transport properties] A material having a hole mobility of 1×10 −６ cm ２ A material having a hole transporting property can be suitably used as a material having a hole transporting property.

[0150] For example, an amine compound or an organic compound having a π-electron-rich heteroaromatic ring skeleton can be used as a material having hole transport properties. Specifically, a compound having an aromatic amine skeleton, a compound having a carbazole skeleton, a compound having a thiophene skeleton, a compound having a furan skeleton, or the like can be used. In particular, a compound having an aromatic amine skeleton or a compound having a carbazole skeleton is preferable because it has good reliability, high hole transport properties, and contributes to reducing driving voltage.

[0151] Examples of compounds having an aromatic amine skeleton include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminobiphenyl (abbreviation: TPD), 4,4'-bis(9,9'-spirobi[9H-fluoren]-2-yl)-N,N'-diphenyl-4,4'-diaminobiphenyl (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), Examples of compounds that can be used include 4,4'-diphenyl-4"-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBiBP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4"-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), and N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: PCBASF).

[0152] Examples of compounds having a carbazole skeleton include 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviation: CzTP), and 9,9'-diphenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCP).

[0153] Examples of compounds having a thiophene skeleton that can be used include 4,4′,4″-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), and 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV).

[0154] Examples of compounds having a furan skeleton that can be used include 4,4′,4″-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II), 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II), and the like.

[0155] <<Structure Example of Layer 113>> For example, a material having an electron-transporting property, a material having an anthracene skeleton, a mixed material, or the like can be used for the layer 113. The layer 113 can also be referred to as an electron-transporting layer. Note that a structure in which a material having a larger band gap than that of the light-emitting material contained in the layer 111X is used for the layer 113 is preferable. This can suppress energy transfer from excitons generated in the layer 111X to the layer 113.

[0156] [Electron-Transporting Material] For example, a material having an electron mobility of 1×10 under the condition that the square root of the electric field strength [V / cm] is 600. −７ cm ２ / Vs or more, 5×10 −５ cm ２ A material having a .DELTA. / Vs or less can be suitably used as a material having electron transport properties. This can suppress the electron transport properties in the electron transport layer. Alternatively, it can control the amount of electrons injected into the light-emitting layer. Alternatively, it can prevent the light-emitting layer from becoming an electron-excess state.

[0157] For example, a metal complex or an organic compound having a π-electron-deficient heteroaromatic ring skeleton can be used as the material having electron transport properties.

[0158] Examples of metal complexes include 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), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), and the like can be used.

[0159] Examples of organic compounds having a π-electron-deficient heteroaromatic ring skeleton include heterocyclic compounds having a polyazole skeleton, heterocyclic compounds having a diazine skeleton, heterocyclic compounds having a pyridine skeleton, and heterocyclic compounds having a triazine skeleton. In particular, heterocyclic compounds having a diazine skeleton or heterocyclic compounds having a pyridine skeleton are preferred because of their high reliability. Furthermore, heterocyclic compounds having a diazine (pyrimidine or pyrazine) skeleton have high electron transport properties and can reduce driving voltage.

[0160] Examples of heterocyclic compounds having a polyazole skeleton include 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-triazole (abbreviation: TAZ), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: O XD-7), 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviation: CO11), 2,2′,2″-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), and the like can be used.

[0161] Examples of heterocyclic compounds having a diazine skeleton include 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: 2mDBTBPDBq-II), and 2-[3′-(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II). ]quinoxaline (abbreviation: 2mCzBPDBq), 4,6-bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,8-bis[3-(dibenzothiophen-4-yl)phenyl]benzo[h]quinazoline (abbreviation: 4,8mDBtP2Bqn), etc. can be used.

[0162] Examples of heterocyclic compounds having a pyridine skeleton include 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), and the like.

[0163] Examples of heterocyclic compounds having a triazine skeleton include 2-[3′-(9,9-dimethyl-9H-fluoren-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn), 2-[(1,1′-biphenyl)-4-yl]-4-phenyl-6-[9,9′-spirobi(9H-fluoren)-2-yl]-1,3,5-triazine (abbreviation: BP-SFT zn), 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-8-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mBnfBPTzn), 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-6-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mBnfBPTzn-02), and the like can be used.

[0164] [Material Having an Anthracene Skeleton] An organic compound having an anthracene skeleton can be used for the layer 113. In particular, an organic compound having both an anthracene skeleton and a heterocyclic skeleton can be preferably used.

[0165] For example, an organic compound including both an anthracene skeleton and a nitrogen-containing five-membered ring skeleton can be used for the layer 113. Alternatively, an organic compound including both an anthracene skeleton and a nitrogen-containing five-membered ring skeleton including two heteroatoms in the ring can be used for the layer 113. Specifically, a pyrazole ring, an imidazole ring, an oxazole ring, a thiazole ring, or the like can be preferably used as the heterocyclic skeleton.

[0166] For example, an organic compound including both an anthracene skeleton and a nitrogen-containing six-membered ring skeleton can be used for the layer 113. Alternatively, an organic compound including both an anthracene skeleton and a nitrogen-containing six-membered ring skeleton including two heteroatoms in the ring can be used for the layer 113. Specifically, a pyrazine ring, a pyrimidine ring, a pyridazine ring, or the like can be preferably used as the heterocyclic skeleton.

[0167] [Configuration Example of Mixed Material] A material in which a plurality of substances are mixed can be used for the layer 113. Specifically, a mixed material containing an alkali metal, an alkali metal compound, or an alkali metal complex, and a substance having an electron-transport property can be used for the layer 113. Note that the highest occupied molecular orbital (HOMO) level of the material having an electron-transport property is more preferably −6.0 eV or higher.

[0168] The alkali metal, alkali metal compound, or alkali metal complex is preferably present with a concentration difference (including zero) in the thickness direction of the layer 113 .

[0169] For example, a metal complex containing an 8-hydroxyquinolinato structure can be used. Also, a methyl-substituted metal complex containing an 8-hydroxyquinolinato structure (for example, a 2-methyl-substituted or 5-methyl-substituted metal complex) can be used.

[0170] Examples of metal complexes containing an 8-hydroxyquinolinato structure include 8-hydroxyquinolinato-lithium (abbreviation: Liq), 8-hydroxyquinolinato-sodium (abbreviation: Naq), etc. In particular, complexes of monovalent metal ions, especially lithium complexes, are preferred, with Liq being more preferred.

[0171] Note that the mixed material can be preferably used for the layer 113 in combination with a structure in which a composite material, which will be described separately, is used for the layer 104. For example, a composite material of a substance having an electron-accepting property and a material having a hole-transporting property can be used for the layer 104. Specifically, a composite material of a substance having an electron-accepting property and a substance having a relatively deep HOMO level HM1 of −5.7 eV or more and −5.4 eV or less can be used for the layer 104 (see FIG. 1B ). By using the mixed material for the layer 113 in combination with a structure in which such a composite material is used for the layer 104, the reliability of the light-emitting device can be improved.

[0172] It is also preferable to combine a structure in which the mixed material is used for the layer 113 and the composite material is used for the layer 104 with a structure in which a material having hole-transporting properties is used for the layer 112. For example, a substance having a HOMO level HM2 in the range of -0.2 eV to 0 eV, relative to the relatively deep HOMO level HM1, can be used for the layer 112 (see FIG. 1B). This can improve the reliability of the light-emitting device. Note that in this specification and the like, the above-described light-emitting device may be referred to as a Recombination-Site Tailoring Injection structure (ReSTI structure).

[0173] <<Structure Example 1 of Layer 111X>> For example, a light-emitting material, or a light-emitting material and a host material, can be used for the layer 111X. The layer 111X can also be referred to as a light-emitting layer. Note that a structure in which the layer 111X is disposed in a region where holes and electrons recombine is preferable. This allows energy generated by carrier recombination to be efficiently converted into light and emitted.

[0174] Furthermore, it is preferable to arrange the layer 111X away from metals used for the electrodes, etc. This makes it possible to suppress the quenching phenomenon caused by the metals used for the electrodes, etc.

[0175] Furthermore, it is preferable to adjust the distance from a reflective electrode or the like to the layer 111X and place the layer 111X at an appropriate position according to the emission wavelength. This allows the interference phenomenon between the light reflected by the electrode or the like and the light emitted by the layer 111X to be utilized to reinforce the amplitudes. Furthermore, it is possible to strengthen the light spectrum by strengthening the light of a specific wavelength. Furthermore, it is possible to obtain a vivid emission color with high intensity. In other words, it is possible to form a microresonator structure (microcavity) by placing the layer 111X at an appropriate position between the electrodes or the like.

[0176] The luminescent material may be, for example, a phosphorescent material, which allows the energy generated by carrier recombination to be emitted from the luminescent material as light ELX (see FIG. 1A).

[0177] [Phosphorescent Substance] A phosphorescent substance can be used for the layer 111X. For example, the organic compound of one embodiment of the present invention described in Embodiment 1 can be used for the layer 111X.

[0178] For example, {2-[5-(methyl-d3)-4-phenyl-2-pyridinyl-κN]phenyl-κC}bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(ppy) ２ (5m4dppy-d3)), bis{2-[5-(methyl-d3)-4-phenyl-2-pyridinyl-κN]phenyl-κC}[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(5m4dppy-d3) ２ (ppy)), or {2-[4-(3,5-di-tert-butylphenyl)-5-(methyl-d)-2-pyridinyl-κN]phenyl-κC}bis{2-[4-(methyl-d)-5-(2-methylpropyl-1,1-d)-2-pyridinyl-κN]phenyl-κC}iridium(III) (abbreviation: Ir(5iBu4mppy-d) ２(4mmtBup5mppy-d3)), etc. can be used for layer 111X.

[0179] The layer 111X includes an organic compound according to one embodiment of the present invention. This suppresses free rotation of the phenyl group having a cyano group introduced therein, thereby improving the thermal properties of the compound, for example, suppressing thermal decomposition. Furthermore, sublimation, which allows the compound to sublimate without thermal decomposition, can be improved. Furthermore, durability in use in high-temperature environments can be achieved. Furthermore, the twist generated between the phenyl group having a cyano group introduced therein and the phenylpyridine skeleton to which iridium is coordinated can shorten the emission wavelength. Furthermore, high luminous efficiency can be achieved. As a result, a novel light-emitting device with excellent convenience, usefulness, and reliability can be provided.

[0180] <<Structural Example 2 of Layer 111X>> A material having carrier transport properties can be used as the host material. For example, a material having hole transport properties, a material having electron transport properties, a substance exhibiting thermally activated delayed fluorescence (TADF), a material having an anthracene skeleton, or a mixed material selected from two or more of these can be used as the host material. Note that a structure in which a material having a larger band gap than the light-emitting material contained in the layer 111X is used as the host material is preferable. This can suppress energy transfer from excitons generated in the layer 111X to the host material.

[0181] [Material having hole transport properties] A material having a hole mobility of 1×10 −６ cm ２ For example, the material having a hole-transport property that can be used for the layer 112 can be used as the host material.

[0182] [Electron-Transporting Material] A metal complex or an organic compound having a π-electron-deficient heteroaromatic ring skeleton can be used as the electron-transporting material. For example, the electron-transporting material that can be used for the layer 113 can be used as the host material.

[0183] [Configuration Example 1 of Mixed Material] A material obtained by mixing a plurality of substances can be used as the host material. For example, a material having electron transport properties and a material having hole transport properties can be used as the mixed material. The weight ratio of the material having hole transport properties to the material having electron transport properties contained in the mixed material may be set to (material having hole transport properties / material having electron transport properties) = (1 / 19) or more and (19 / 1) or less. This allows the carrier transport properties of the layer 111X to be easily adjusted. Furthermore, the recombination region can be easily controlled.

[0184] [Configuration Example 2 of Mixed Material] The organic compound of one embodiment of the present invention can be used as a host material. The organic compound of one embodiment of the present invention is a phosphorescent substance, and when a fluorescent substance is used as a light-emitting substance, the phosphorescent substance can be used as an energy donor that provides excitation energy to the fluorescent substance.

[0185] As a result, the emission spectrum of the organic compound of one embodiment of the present invention includes light with a wavelength shorter than 500 nm. Therefore, when the organic compound of one embodiment of the present invention is used together with a fluorescent light-emitting material having an absorption spectrum overlapping with the emission spectrum, for example, a fluorescent light-emitting material emitting green light, energy can be efficiently transferred to the fluorescent light-emitting material. Furthermore, the phenomenon in which the luminance of the light-emitting device decreases with use can be suppressed. Furthermore, the reliability of the light-emitting device can be improved. As a result, a novel light-emitting device with excellent convenience, usefulness, and reliability can be provided.

[0186] [Structure Example 3 of Mixed Material] A mixed material containing a material that forms an exciplex can be used as a host material. For example, a material whose emission spectrum of the formed exciplex overlaps with the wavelength of the lowest-energy absorption band of the light-emitting substance can be used as a host material. Specifically, a mixed material containing a material having electron-transporting properties and a material having hole-transporting properties can be used as a material that forms an exciplex. This allows smooth energy transfer, improving light-emitting efficiency. Alternatively, driving voltage can be suppressed. With this structure, light emission can be efficiently obtained using Exciplex-Triple Energy Transfer (ExTET), which is energy transfer from the exciplex to the light-emitting substance (phosphorescent material).

[0187] At least one of the materials forming the exciplex can be a phosphorescent material, which allows for the utilization of reverse intersystem crossing and efficient conversion of triplet excitation energy to singlet excitation energy.

[0188] As a combination of materials for forming an exciplex, it is preferable that the HOMO level of the material having hole transport properties is equal to or higher than the HOMO level of the material having electron transport properties. Alternatively, it is preferable that the lowest unoccupied molecular orbital (LUMO) level of the material having hole transport properties is equal to or higher than the LUMO level of the material having electron transport properties. This allows for efficient formation of an exciplex. The LUMO level and HOMO level of a material can be derived from electrochemical properties (reduction potential and oxidation potential). Specifically, the reduction potential and oxidation potential can be measured using cyclic voltammetry (CV) measurement.

[0189] The formation of exciplexes can be confirmed, for example, by comparing the emission spectra of a material having hole transport properties, a material having electron transport properties, and a mixed film obtained by mixing these materials, and observing the phenomenon in which the emission spectrum of the mixed film is shifted to longer wavelengths than the emission spectra of each material (or has a new peak on the longer wavelength side). Alternatively, the formation of exciplexes can be confirmed by comparing the transient photoluminescence (PL) of a material having hole transport properties, the transient PL of a material having electron transport properties, and a mixed film obtained by mixing these materials, and observing differences in transient response, such as the transient PL lifetime of the mixed film having a longer-lifetime component or a larger proportion of delayed components than the transient PL lifetimes of the individual materials. The above-mentioned transient PL may also be interpreted as transient electroluminescence (EL). In other words, the formation of exciplexes can also be confirmed by comparing the transient EL of a material having hole transport properties, the transient EL of a material having electron transport properties, and a mixed film obtained by mixing these materials, and observing the differences in transient response.

[0190] Note that this embodiment mode can be appropriately combined with other embodiment modes described in this specification.

[0191] Embodiment 3 In this embodiment, a structure of a light-emitting device 550X of one embodiment of the present invention will be described with reference to FIGS. 1A and 1B.

[0192] <Structure Example of Light-Emitting Device 550X> The light-emitting device 550X described in this embodiment includes an electrode 551X, an electrode 552X, a unit 103X, and a layer 104. The electrode 552X overlaps with the electrode 551X, and the unit 103X is sandwiched between the electrode 551X and the electrode 552X. The layer 104 is sandwiched between the electrode 551X and the unit 103X. Note that the structure described in Embodiment 2 can be used for the unit 103X, for example.

[0193] <Structure Example of Electrode 551X> For example, a conductive material can be used for the electrode 551X. Specifically, a single layer or a stacked layer of a film containing a metal, an alloy, or a conductive compound can be used for the electrode 551X.

[0194] For example, a film that efficiently reflects light can be used for the electrode 551X. Specifically, a film of a metal such as an alloy containing silver and copper, an alloy containing silver and palladium, or aluminum can be used for the electrode 551X.

[0195] Furthermore, for example, a metal film that transmits part of the light and reflects the other part of the light can be used for the electrode 551X. This allows a microresonator structure (microcavity) to be provided in the light-emitting device 550X. Alternatively, light of a specific wavelength can be extracted more efficiently than other light. Alternatively, light with a narrow spectral half-width can be extracted. Alternatively, light of a vivid color can be extracted.

[0196] For example, a film that transmits visible light can be used for the electrode 551X. Specifically, a single layer or stacked layer of a metal film, an alloy film, a conductive oxide film, or the like that is thin enough to transmit light can be used for the electrode 551X.

[0197] In particular, a material having a work function of 4.0 eV or more can be suitably used for the electrode 551X.

[0198] For example, a conductive oxide containing indium can be used, such as indium oxide, indium oxide-tin oxide (abbreviation: ITO), indium oxide-tin oxide containing silicon or silicon oxide (abbreviation: ITSO), indium oxide-zinc oxide, or indium oxide containing tungsten oxide and zinc oxide (abbreviation: IWZO).

[0199] Alternatively, for example, a conductive oxide containing zinc can be used, such as zinc oxide, zinc oxide doped with gallium, or zinc oxide doped with aluminum.

[0200] Alternatively, for example, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), or a nitride of a metal material (e.g., titanium nitride) can be used. Alternatively, graphene can be used.

[0201] <<Structure Example 1 of Layer 104>> For example, a material having a hole-injecting property can be used for the layer 104. The layer 104 can also be referred to as a hole-injecting layer.

[0202] For example, the hole mobility is 1×10 when the square root of the electric field strength V / cm is 600. −３ A material having a resistivity of 1×10 cm / Vs or less can be used for the layer 104. ４ Ω・cm or more 1×10 ７ A film having an electrical resistivity of Ω·cm or less can be used for the layer 104. Preferably, the layer 104 has a resistivity of 5×10 ４ Ω・cm or more 1×10 ７ It has an electrical resistivity of Ω cm or less, and more preferably, 1×10 ５ Ω・cm or more 1×10 ７ It has an electrical resistivity of Ω·cm or less.

[0203] <<Structure Example 2 of Layer 104>> Specifically, a substance having an electron-accepting property can be used for the layer 104. Alternatively, a composite material containing a plurality of substances can be used for the layer 104. This can make it easier to inject holes from the electrode 551X, for example. Alternatively, the driving voltage of the light-emitting device 550X can be reduced.

[0204] [Substance with Electron Accepting Property] Organic compounds and inorganic compounds can be used as the substance with electron accepting property. The substance with electron accepting property can extract electrons from the adjacent hole transport layer or the material with hole transporting property by applying an electric field.

[0205] For example, a compound having an electron-withdrawing group (a halogen group or a cyano group) can be used as the electron-accepting substance. Note that organic compounds having electron-accepting properties can be easily vapor-deposited and easily formed into a film. This can increase the productivity of the light-emitting device 550X.

[0206] Specifically, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ), chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN), 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCCNNQ), 2-(7-dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyren-2-ylidene)malononitrile, and the like can be used.

[0207] In particular, a compound in which an electron-withdrawing group is bonded to a condensed aromatic ring having a plurality of heteroatoms, such as HAT-CN, is thermally stable and is therefore preferred.

[0208] [3] Radialene derivatives having an electron-withdrawing group (particularly a halogen group such as a fluoro group or a cyano group) are also preferred because they have very high electron-accepting properties.

[0209] Specifically, α,α',α''-1,2,3-cyclopropane triylidene tris[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α',α''-1,2,3-cyclopropane triylidene tris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], α,α',α''-1,2,3-cyclopropane triylidene tris[2,3,4,5,6-pentafluorobenzeneacetonitrile], and the like can be used.

[0210] Furthermore, transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide can be used as the electron-accepting substance.

[0211] In addition, phthalocyanine compounds or complex compounds such as phthalocyanine (abbreviation: HPc) and copper phthalocyanine (abbreviation: CuPc), and compounds having an aromatic amine skeleton such as 4,4′-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB) and N,N′-bis[4-bis(3-methylphenyl)aminophenyl]-N,N′-diphenyl-4,4′-diaminobiphenyl (abbreviation: DNTPD) can be used.

[0212] Furthermore, polymers such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) can also be used.

[0213] [Structure Example 1 of Composite Material] Furthermore, for example, a composite material containing a substance having an electron-accepting property and a material having a hole-transporting property can be used for the layer 104. As a result, not only a material having a high work function but also a material having a low work function can be used for the electrode 551X. Alternatively, a material for the electrode 551X can be selected from a wide range of materials regardless of the work function.

[0214] For example, compounds having an aromatic amine skeleton, carbazole derivatives, aromatic hydrocarbons, aromatic hydrocarbons having a vinyl group, and polymeric compounds (oligomers, dendrimers, polymers, etc.) can be used as the material having hole transport properties for the composite material. −６ cm ２ For example, the material having a hole-transport property that can be used for the layer 112 can be used for the composite material.

[0215] Furthermore, a substance having a relatively deep HOMO level can be preferably used as the material having hole-transporting properties of the composite material. Specifically, the HOMO level is preferably −5.7 eV or more and −5.4 eV or less. This facilitates injection of holes into the unit 103X. Furthermore, it facilitates injection of holes into the layer 112. Furthermore, it improves the reliability of the light-emitting device 550X.

[0216] Examples of compounds having an aromatic amine skeleton that can be used include 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)aminophenyl]-N,N'-diphenyl-4,4'-diaminobiphenyl (abbreviation: DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B).

[0217] 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, and carbazole (abbreviation: PCzPCN1), 4,4′-di(N-carbazolyl)biphenyl (abbreviation: CBP), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), 1,4-bis[4-(N-carbazolyl)phenyl]-2,3,5,6-tetraphenylbenzene, and the like can be used.

[0218] Examples of aromatic hydrocarbons include 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 10,10'-bis[2-(1-naphthyl)phenyl]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, pentacene, coronene, and the like can be used.

[0219] Examples of aromatic hydrocarbons having a vinyl group include 4,4'-bis(2,2-diphenylvinyl)biphenyl (abbreviation: DPVBi), 9,10-bis[4-(2,2-diphenylvinyl)phenyl]anthracene (abbreviation: DPVPA), and the like.

[0220] Examples of polymer compounds that can be used include poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD).

[0221] For example, a substance having a carbazole skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton, or an anthracene skeleton can be suitably used as the material having hole transport properties for the composite material. Furthermore, a substance having an aromatic amine with a substituent containing a dibenzofuran ring or a dibenzothiophene ring, an aromatic monoamine with a naphthalene ring, or an aromatic monoamine in which a 9-fluorenyl group is bonded to the nitrogen of the amine via an arylene group can be used as the material having hole transport properties for the composite material. Note that the use of a substance having an N,N-bis(4-biphenyl)amino group can improve the reliability of the light-emitting device 550X.

[0222] Examples of these materials include N-(4-biphenyl)-6,N-diphenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BnfABP), N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf), 4,4′-bis(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)-4″-phenyltriphenylamine (abbreviation: BnfBB1BP), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2 -d]furan-6-amine (abbreviation: BBABnf(6)), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf(8)), N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviation: BBABnf(II)(4)), N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP), N-[4-(dibenzothiophen-4-yl)phenyl]-N-phenyl -4-biphenylamine (abbreviation: ThBA1BP), 4-(2-naphthyl)-4',4''-diphenyltriphenylamine (abbreviation: BBAβNB), 4-[4-(2-naphthyl)phenyl]-4',4''-diphenyltriphenylamine (abbreviation: BBAβNBi), 4,4'-diphenyl-4''-(6;1'-binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβNB), 4,4'-diphenyl-4''-(7;1'-binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβNB-0 3), 4,4'-diphenyl-4''-(7-phenyl)naphthyl-2-yltriphenylamine (abbreviation: BBAPβNB-03), 4,4'-diphenyl-4''-(6;2'-binaphthyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B), 4,4'-diphenyl-4''-(7;2'-binaphthyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B-03), 4,4'-diphenyl-4''-(4;2'-binaphthyl-1-yl)triphenylamine (abbreviation: BBAβNαNB), 4,4'-Diphenyl-4''-(5;2'-binaphthyl-1-yl)triphenylamine (abbreviation: BBAβNαNB-02), 4-(4-biphenylyl)-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: TPBiAβNB), 4-(3-biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: mTPBiAβNBi), 4-(4-biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4'' -phenyltriphenylamine (abbreviation: TPBiAβNBi), 4-phenyl-4′-(1-naphthyl)triphenylamine (abbreviation: αNBA1BP), 4,4′-bis(1-naphthyl)triphenylamine (abbreviation: αNBB1BP), 4,4′-diphenyl-4″-[4′-(carbazol-9-yl)biphenyl-4-yl]triphenylamine (abbreviation: YGTBi1BP), 4′-[4-(3-phenyl-9H-carbazol-9-yl)phenyl]tris(1,1′ -biphenyl-4-yl)amine (abbreviation: YGTBi1BP-02), 4-[4'-(carbazol-9-yl)biphenyl-4-yl]-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: YGTBiβNB), N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-N-[4-(1-naphthyl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: PCBNBSF), N,N-bis([1,1'-biphenyl N-(1,1'-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[9H-fluoren]-4-amine (abbreviation: oFBiSF), N-(biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzofuran-4-amine (abbreviation: FrBiF), N-[4-(1-naphthyl)phenyl]-N-[3-(6-phenyldibenzofuran-4-yl)phenyl]-1-naphthylamine (abbreviation: mPDBfBNBN), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-phenyl-4'-[ 4-(9-phenylfluoren-9-yl)phenyl]triphenylamine (abbreviation: BPAFLBi), 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1 -naphthyl)-4"-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: PCBASF), N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluorene-2-amine (abbreviation: PCBBiF), N,N-bis( 9,9-dimethyl-9H-fluoren-2-yl)-9,9′-spirobi-9H-fluoren-4-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9′-spirobi-9H-fluoren-3-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9′-spirobi-9H-fluoren-2-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9′-spirobi-9H-fluoren-1-amine, etc. can be used.

[0223] [Configuration Example 2 of Composite Material] For example, a composite material containing a substance having an electron-accepting property, a material having a hole-transporting property, and an alkali metal fluoride or an alkaline earth metal fluoride can be used as the material having a hole-injecting property. In particular, a composite material containing fluorine atoms at an atomic ratio of 20% or more can be preferably used. This can reduce the refractive index of the layer 104. Alternatively, a layer with a low refractive index can be formed inside the light-emitting device 550X. Alternatively, the external quantum efficiency of the light-emitting device 550X can be improved.

[0224] Note that this embodiment mode can be appropriately combined with other embodiment modes described in this specification.

[0225] Embodiment 4 In this embodiment, a structure of a light-emitting device 550X of one embodiment of the present invention will be described with reference to FIGS. 1A and 1B.

[0226] <Structure Example of Light-Emitting Device 550X> The light-emitting device 550X described in this embodiment includes an electrode 551X, an electrode 552X, a unit 103X, and a layer 105. The electrode 552X has a region overlapping with the electrode 551X, and the unit 103X has a region sandwiched between the electrode 551X and the electrode 552X. The layer 105 also has a region sandwiched between the unit 103X and the electrode 552X. Note that the structure described in Embodiment 2 can be used for the unit 103X, for example.

[0227] <Structure Example of Electrode 552X> For example, a conductive material can be used for the electrode 552X. Specifically, a material containing a metal, an alloy, or a conductive compound can be used as a single layer or a stacked layer for the electrode 552X.

[0228] For example, the material that can be used for the electrode 551X described in Embodiment 3 can be used for the electrode 552X. In particular, a material having a work function smaller than that of the electrode 551X can be suitably used for the electrode 552X. Specifically, a material having a work function of 3.8 eV or less is preferable.

[0229] For example, elements belonging to Group 1 of the periodic table, elements belonging to Group 2 of the periodic table, rare earth metals, and alloys containing these can be used for the electrode 552X.

[0230] Specifically, lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), strontium (Sr), europium (Eu), ytterbium (Yb), and alloys containing these, such as an alloy of magnesium and silver or an alloy of aluminum and lithium, can be used for the electrode 552X.

[0231] <Structure Example of Layer 105> For example, a material having an electron injecting property can be used for the layer 105. The layer 105 can also be referred to as an electron injecting layer.

[0232] Specifically, a substance having electron donating properties can be used for the layer 105. Alternatively, a composite material of a substance having electron donating properties and a material having electron transporting properties can be used for the layer 105. Alternatively, an electride can be used for the layer 105. This can facilitate electron injection from the electrode 552X, for example. Alternatively, not only a material having a low work function but also a material having a high work function can be used for the electrode 552X. Alternatively, a material for the electrode 552X can be selected from a wide range of materials regardless of the work function. Specifically, Al, Ag, ITO, indium oxide-tin oxide containing silicon or silicon oxide, or the like can be used for the electrode 552X. Alternatively, the driving voltage of the light-emitting device 550X can be reduced.

[0233] [Electron-donating substance] For example, alkali metals, alkaline earth metals, rare earth metals, or compounds thereof (oxides, halides, carbonates, etc.) can be used as the electron-donating substance. Alternatively, organic compounds such as tetrathianaphthacene (abbreviation: TTN), nickelocene, and decamethylnickelocene can also be used as the electron-donating substance.

[0234] Examples of alkali metal compounds (including oxides, halides, and carbonates) that can be used include lithium oxide, lithium fluoride (LiF), cesium fluoride (CsF), lithium carbonate, cesium carbonate, and 8-hydroxyquinolinato-lithium (abbreviated as Liq).

[0235] Alkaline earth metal compounds (including oxides, halides, and carbonates) include calcium fluoride (CaF ２ ), etc. can be used.

[0236] [Configuration Example 1 of Composite Material] A composite material of a plurality of substances can be used as a material having an electron injecting property. For example, a material having an electron donating property and a material having an electron transporting property can be used as a composite material.

[0237] [Electron-Transporting Material] For example, a material having an electron mobility of 1×10 under the condition that the square root of the electric field strength V / cm is 600. −７ cm ２ / Vs or more, 5×10 −５ cm ２ A material having a .DELTA..times ...

[0238] A metal complex or an organic compound having a π-electron-deficient heteroaromatic skeleton can be used as the material having an electron-transport property. For example, the material having an electron-transport property that can be used for the layer 113 can be used as the composite material.

[0239] [Configuration Example 2 of Composite Material] A microcrystalline alkali metal fluoride and a material having an electron transport property can be used for the composite material. Alternatively, a microcrystalline alkaline earth metal fluoride and a material having an electron transport property can be used for the composite material. In particular, a composite material containing 50 wt % or more of an alkali metal fluoride or an alkaline earth metal fluoride can be preferably used. Alternatively, a composite material containing an organic compound having a bipyridine skeleton can be preferably used. This can reduce the refractive index of the layer 105. Alternatively, the external quantum efficiency of the light-emitting device 550X can be improved.

[0240] [Structure Example 3 of Composite Material] For example, a composite material containing a first organic compound having an unshared electron pair and a first metal can be used for the layer 105. The sum of the number of electrons in the first organic compound and the number of electrons in the first metal is preferably an odd number. The molar ratio of the first metal to 1 mole of the first organic compound is preferably 0.1 to 10, more preferably 0.2 to 2, and even more preferably 0.2 to 0.8.

[0241] This allows the first organic compound having an unshared electron pair to interact with the first metal to form a Singly Occupied Molecular Orbital (SOMO), and also reduces the barrier between the electrode 552X and the layer 105 when electrons are injected from the electrode 552X to the layer 105.

[0242] The spin density measured by electron spin resonance (ESR) is preferably 1×10 １６ spins / cm ３ or more, more preferably 5 × 10 １６ spins / cm ３ More preferably, 1×10 １７ spins / cm ３ The above composite material can be used for the layer 105 .

[0243] [Organic Compound Having an Unshared Electron Pair] For example, a material having electron transport properties can be used as the organic compound having an unshared electron pair. For example, a compound having an electron-deficient heteroaromatic ring can be used. Specifically, a compound having at least one of a pyridine ring, a diazine ring (pyrimidine ring, pyrazine ring, pyridazine ring), and a triazine ring can be used. This can reduce the driving voltage of the light-emitting device 550X.

[0244] The organic compound having an unshared electron pair preferably has a lowest unoccupied molecular orbital (LUMO) level of −3.6 eV to −2.3 eV. Generally, the HOMO level and LUMO level of an organic compound can be estimated by cyclic voltammetry (CV), photoelectron spectroscopy, optical absorption spectroscopy, inverse photoelectron spectroscopy, or the like.

[0245] For example, 4,7-diphenyl-1,10-phenanthroline (abbreviation: BPhen), 2,9-di(2-naphthyl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen), diquinoxalino[2,3-a:2',3'-c]phenazine (abbreviation: HATNA), 2,4,6-tris[3'-(pyridin-3-yl)biphenyl-3-yl]-1,3,5-triazine (abbreviation: TmPPPyTz), 2,2'-(1,3-phenylene)bis(9-phenyl-1,10-phenanthroline) (abbreviation: mPPhen2P), etc. can be used as the organic compound having an unshared electron pair. Note that NBPhen has a higher glass transition temperature (Tg) and is superior in heat resistance compared to BPhen.

[0246] Furthermore, for example, copper phthalocyanine, which has an odd number of electrons, can be used as the organic compound having an unshared electron pair.

[0247] [First Metal] For example, when the number of electrons in the first organic compound having an unshared electron pair is even, a composite material of the first organic compound and a metal belonging to an odd group in the periodic table can be used for the layer 105.

[0248] For example, manganese (Mn), a Group 7 metal; cobalt (Co), a Group 9 metal; copper (Cu), silver (Ag), and gold (Au), which are Group 11 metals; and aluminum (Al) and indium (In), which are Group 13 metals, are odd-numbered groups in the periodic table. The elements of Group 11 have lower melting points than the elements of Groups 7 and 9, making them suitable for vacuum deposition. Ag, in particular, is preferred due to its low melting point. Furthermore, by using a metal with poor reactivity with water or oxygen as the first metal, the moisture resistance of the light-emitting device 550X can be improved.

[0249] Note that by using Ag for the electrode 552X and the layer 105, the adhesion between the layer 105 and the electrode 552X can be improved.

[0250] When the number of electrons in the first organic compound having an unshared electron pair is odd, a composite material of the first metal and the first organic compound that belong to an even group in the periodic table can be used for the layer 105. For example, iron (Fe), which is a metal in Group 8 of the periodic table, belongs to an even group in the periodic table.

[0251] [Electride] For example, a substance in which electrons are added to a mixed oxide of calcium and aluminum at a high concentration can be used as a material having electron injection properties.

[0252] Note that this embodiment mode can be appropriately combined with other embodiment modes described in this specification.

[0253] Embodiment 5 In this embodiment, a structure of a light-emitting device 550X of one embodiment of the present invention will be described with reference to FIG. 2A.

[0254] FIG. 2A is a cross-sectional view illustrating a structure of a light-emitting device according to one embodiment of the present invention.

[0255] <Configuration Example of Light-Emitting Device 550X> The light-emitting device 550X described in this embodiment includes an electrode 551X, an electrode 552X, a unit 103X, and a layer 106 (see FIG. 2A ). The electrode 552X has a region overlapping with the electrode 551X, and the unit 103X has a region sandwiched between the electrode 551X and the electrode 552X. The layer 106 has a region sandwiched between the electrode 552X and the unit 103X.

[0256] <<Configuration Example 1 of Layer 106>> The layer 106 has a function of supplying electrons to the anode side and holes to the cathode side when a voltage is applied. The layer 106 can also be called a charge generation layer.

[0257] For example, the material having a hole-injecting property which can be used for the layer 104 described in Embodiment 3 can be used for the layer 106. Specifically, the layer 106 can be a composite material.

[0258] Furthermore, for example, a stacked film in which a film containing the composite material and a film containing a material having a hole-transporting property are stacked can be used for the layer 106. Note that the film containing the material having a hole-transporting property is sandwiched between the film containing the composite material and the cathode.

[0259] <<Structure Example 2 of Layer 106>> A stacked film in which a layer 106_1 and a layer 106_2 are stacked can be used as the layer 106. The layer 106_1 includes a region sandwiched between the unit 103X and the electrode 552X, and the layer 106_2 includes a region sandwiched between the unit 103X and the layer 106_1.

[0260] <Structure Example of Layer 106_1> For example, the material having a hole-injecting property that can be used for the layer 104 described in Embodiment 3 can be used for the layer 106_1. Specifically, a composite material can be used for the layer 106_1. ４ [Ω・cm] or more 1×10 ７ A film having an electrical resistivity of 5×10 [Ω·cm] or less can be used for the layer 106_1. ４ [Ω・cm] or more 1×10 ７ [Ω cm] or less, and more preferably, 1×10 ５ [Ω・cm] or more 1×10 ７ It has an electrical resistivity of [Ω·cm] or less.

[0261] <Structure Example of Layer 106_2> For example, the material that can be used for the layer 105 described in Embodiment 4 can be used for the layer 106_2.

[0262] <Structure Example 3 of Layer 106> A stacked film including a layer 106_1, a layer 106_2, and a layer 106_3 can be used as the layer 106. The layer 106_3 includes a region sandwiched between the layer 106_1 and the layer 106_2.

[0263] <<Structure Example of Layer 106_3>> For example, a material having electron transport properties can be used for the layer 106_3. The layer 106_3 can also be referred to as an electron relay layer. By using the layer 106_3, a layer in contact with the anode side of the layer 106_3 can be separated from a layer in contact with the cathode side of the layer 106_3. The interaction between the layer in contact with the anode side of the layer 106_3 and the layer in contact with the cathode side of the layer 106_3 can be reduced. Electrons can be smoothly supplied to the layer in contact with the anode side of the layer 106_3.

[0264] A substance having a LUMO level between the LUMO level of an electron-accepting substance included in a layer in contact with the cathode side of the layer 106_3 and the LUMO level of a substance included in a layer in contact with the anode side of the layer 106_3 can be suitably used for the layer 106_3.

[0265] For example, a material having a LUMO level in the range of −5.0 eV or higher, preferably −5.0 eV or higher and −3.0 eV or lower, can be used for the layer 106_3.

[0266] Specifically, a phthalocyanine-based material can be used for the layer 106_3. For example, copper phthalocyanine (abbreviation: CuPc) or a metal complex having a metal-oxygen bond and an aromatic ligand can be used for the layer 106_3.

[0267] Note that this embodiment mode can be appropriately combined with other embodiment modes described in this specification.

[0268] Embodiment 6 In this embodiment, a structure of a light-emitting device 550X of one embodiment of the present invention will be described with reference to FIG. 2B.

[0269] FIG. 2B is a cross-sectional view illustrating a structure of a light-emitting device according to one embodiment of the present invention, which has a structure different from that illustrated in FIG. 2A.

[0270] <Structure Example of Light-Emitting Device 550X> A light-emitting device 550X described in this embodiment includes an electrode 551X, an electrode 552X, a unit 103X, a layer 106, and a unit 103X2 (see FIG. 2B).

[0271] Unit 103X is sandwiched between electrode 552X and electrode 551X, and layer 106 is sandwiched between electrode 552X and unit 103X.

[0272] The unit 103X2 is sandwiched between the electrode 552X and the layer 106. The unit 103X2 has the function of emitting light ELX2.

[0273] In other words, the light-emitting device 550X has a plurality of stacked units between the electrode 551X and the electrode 552X. The number of stacked units is not limited to two, and three or more units may be stacked. A configuration including a plurality of stacked units sandwiched between the electrode 551X and the electrode 552X and the layer 106 sandwiched between the plurality of units may be referred to as a stacked light-emitting device or a tandem light-emitting device.

[0274] This allows for high-luminance light emission while maintaining a low current density, improves reliability, reduces the driving voltage compared to the same luminance, and reduces power consumption.

[0275] <<Configuration Example 1 of Unit 103X2>> The unit 103X2 includes a layer 111X2, a layer 112_2, and a layer 113_2. The layer 111X2 is sandwiched between the layer 112_2 and the layer 113_2.

[0276] The configuration that can be used for the unit 103X can be used for the unit 103X2. For example, the same configuration as the unit 103X can be used for the unit 103X2.

[0277] <<Configuration Example 2 of Unit 103X2>> Furthermore, a configuration different from that of the unit 103X can be used for the unit 103X2. For example, a configuration that emits light having a different hue from the emission color of the unit 103X can be used for the unit 103X2.

[0278] Specifically, a unit 103X that emits red light and green light and a unit 103X2 that emits blue light can be stacked together to provide a light-emitting device that emits light of a desired color, such as a light-emitting device that emits white light.

[0279] <Structural Example of Layer 106> The layer 106 has a function of supplying electrons to one of the unit 103X and the unit 103X2 and supplying holes to the other. For example, the layer 106 described in Embodiment 5 can be used.

[0280] <Method for manufacturing light-emitting device 550X> For example, the electrode 551X, the electrode 552X, the unit 103X, the layer 106, and the unit 103X2 can be formed by a dry method, a wet method, a vapor deposition method, a droplet discharge method, a coating method, a printing method, etc. Different methods can be used to form each component.

[0281] Specifically, the light-emitting device 550X can be produced using a vacuum deposition device, an inkjet device, a coating device such as a spin coater, a gravure printing device, an offset printing device, a screen printing device, or the like.

[0282] For example, an electrode can be formed by a wet method using a paste of a metal material or a sol-gel method. Also, an indium oxide-zinc oxide film can be formed by a sputtering method using a target containing 1 wt % to 20 wt % of zinc oxide added to indium oxide. Also, an indium oxide (IWZO) film containing tungsten oxide and zinc oxide can be formed by a sputtering method using a target containing 0.5 wt % to 5 wt % of tungsten oxide and 0.1 wt % to 1 wt % of zinc oxide added to indium oxide.

[0283] Note that this embodiment mode can be appropriately combined with other embodiment modes described in this specification.

[0284] Embodiment 7 In this embodiment, a structure of a display device 700 of one embodiment of the present invention will be described with reference to FIGS. 3A and 3B.

[0285] 3A is a cross-sectional view illustrating a structure of a display device 700 of one embodiment of the present invention, and FIG. 3B is a cross-sectional view illustrating a structure of the display device 700 of one embodiment of the present invention, which is different from that in FIG. 3A.

[0286] In this specification, variables that take on integer values ​​of 1 or greater may be used as symbols. For example, (p) including a variable p that takes on an integer value of 1 or greater may be used as part of a symbol specifying any one of up to p components. Also, for example, (m, n) including variables m and n that take on integer values ​​of 1 or greater may be used as part of a symbol specifying any one of up to m×n components.

[0287] <Configuration Example 1 of Display Device 700> The display device 700 described in this embodiment includes a light-emitting device 550X(i,j) and a light-emitting device 550Y(i,j) (see FIG. 3A). The light-emitting device 550Y(i,j) is adjacent to the light-emitting device 550X(i,j).

[0288] The display device 700 includes a substrate 510 and a functional layer 520. The functional layer 520 includes an insulating film 521, and the light-emitting device 550X(i,j) and the light-emitting device 550Y(i,j) are formed on the insulating film 521. The functional layer 520 is sandwiched between the substrate 510, the light-emitting device 550X(i,j), and the light-emitting device 550Y(i,j).

[0289] <<Configuration Example of Light-Emitting Device 550X(i,j)>> The light-emitting device 550X(i,j) has an electrode 551X(i,j), an electrode 552X(i,j), and a unit 103X(i,j). The electrode 552X(i,j) overlaps the electrode 551X(i,j), and the unit 103X(i,j) is sandwiched between the electrode 552X(i,j) and the electrode 551X(i,j). The light-emitting device 550X(i,j) also has a layer 104X(i,j) and a layer 105X(i,j), and the layer 104X(i,j) is sandwiched between the unit 103X(i,j) and the electrode 551X(i,j), and the layer 105X(i,j) is sandwiched between the electrode 552X(i,j) and the unit 103X(i,j). The unit 103X(i,j) includes a layer 111X(i,j), a layer 112X(i,j), and a layer 113X(i,j).

[0290] For example, the light-emitting device 550X described in any of Embodiments 2 to 6 can be used for the light-emitting device 550X(i,j). Specifically, a structure that can be used for the electrode 551X can be used for the electrode 551X(i,j), and a structure that can be used for the electrode 552X can be used for the electrode 552X(i,j). A structure that can be used for the unit 103X can be used for the unit 103X(i,j). A structure that can be used for the layer 104 can be used for the layer 104X(i,j), and a structure that can be used for the layer 105 can be used for the layer 105X(i,j). A structure that can be used for the layer 111X can be used for the layer 111X(i,j), a structure that can be used for the layer 112 can be used for the layer 112X(i,j), and a structure that can be used for the layer 113 can be used for the layer 113X(i,j).

[0291] <<Configuration Example of Light-Emitting Device 550Y(i,j)>> The light-emitting device 550Y(i,j) has an electrode 551Y(i,j), an electrode 552Y(i,j), and a unit 103Y(i,j). The electrode 552Y(i,j) overlaps the electrode 551Y(i,j), and the unit 103Y(i,j) is sandwiched between the electrode 552Y(i,j) and the electrode 551Y(i,j). The light-emitting device 550Y(i,j) also has a layer 104Y(i,j) and a layer 105Y(i,j), and the layer 104Y(i,j) is sandwiched between the unit 103Y(i,j) and the electrode 551Y(i,j), and the layer 105Y(i,j) is sandwiched between the electrode 552Y(i,j) and the unit 103Y(i,j).

[0292] The electrode 551Y(i,j) is adjacent to the electrode 551X(i,j), and there is a gap 551XY(i,j) between the electrode 551Y(i,j) and the electrode 551X(i,j).

[0293] Note that part of the structure that can be used for the light-emitting device 550X(i,j) can be used for the light-emitting device 550Y(i,j). For example, part of the conductive film that can be used for the electrode 552X(i,j) can be used for the electrode 552Y(i,j). A structure that can be used for the electrode 551X can be used for the electrode 551Y(i,j). A structure that can be used for the layer 104 can be used for the layer 104Y(i,j), and a structure that can be used for the layer 105 can be used for the layer 105Y(i,j). This allows part of the structure to be common. Furthermore, the manufacturing process can be simplified.

[0294] Furthermore, a configuration that emits light of the same hue as the light emitted by the light-emitting device 550X(i,j) can be used for the light-emitting device 550Y(i,j).

[0295] For example, both the light-emitting device 550X(i,j) and the light-emitting device 550Y(i,j) may emit white light. A colored layer may be placed over the light-emitting device 550X(i,j) to extract light of a predetermined hue from the white light. Another colored layer may be placed over the light-emitting device 550Y(i,j) to extract light of another predetermined hue from the white light.

[0296] Alternatively, for example, both the light-emitting device 550X(i,j) and the light-emitting device 550Y(i,j) may emit blue light. A color conversion layer may be disposed over the light-emitting device 550X(i,j) to convert the blue light into light of a predetermined hue. Another color conversion layer may be disposed over the light-emitting device 550Y(i,j) to convert the blue light into light of another predetermined hue. The blue light may be converted into, for example, green light or red light.

[0297] Furthermore, a configuration that emits light of a hue different from the emission color of the light-emitting device 550X(i,j) can be used for the light-emitting device 550Y(i,j). For example, the hue of the light ELY emitted by the unit 103Y(i,j) can be made different from the hue of the light ELX.

[0298] <<Configuration Example of Unit 103Y(i,j)>> The light-emitting device 550Y(i,j) differs from the light-emitting device 550X(i,j) in the configuration of the layer 111Y(i,j). Here, the differences will be described in detail, and the above description will be applied to the parts having the same configuration.

[0299] <<Configuration Example of Layer 111Y(i,j)>> For example, a light-emitting material, or a light-emitting material and a host material, can be used for the layer 111Y(i,j). The layer 111Y(i,j) can also be referred to as a light-emitting layer. Note that a configuration in which the layer 111Y(i,j) is disposed in a region where holes and electrons recombine can be preferable. This allows the energy generated by carrier recombination to be efficiently converted into light and emitted.

[0300] Furthermore, it is preferable to arrange the layer 111Y(i,j) away from metals used for electrodes, etc. This makes it possible to suppress the quenching phenomenon caused by metals used for electrodes, etc.

[0301] Furthermore, it is preferable to adjust the distance from a reflective electrode or the like to the layer 111Y(i,j) and place the layer 111Y(i,j) at an appropriate position according to the emission wavelength. This allows the interference phenomenon between the light reflected by the electrode or the like and the light emitted by the layer 111Y(i,j) to be utilized to reinforce the amplitude. Furthermore, it is possible to strengthen the light spectrum by intensifying light of a specific wavelength. Furthermore, it is possible to obtain a vivid emission color with high intensity. In other words, it is possible to form a microresonator structure (microcavity) by placing the layer 111Y(i,j) at an appropriate position between the electrodes or the like.

[0302] For example, the light-emitting material can be a fluorescent material, a phosphorescent material, or a material exhibiting thermally activated delayed fluorescence (TADF) (also called a TADF material), which allows the energy generated by carrier recombination to be emitted from the light-emitting material as light ELY (see FIGS. 3A and 3B).

[0303] [Fluorescent Material] A fluorescent material can be used in the layer 111Y(i,j). For example, the fluorescent materials exemplified below can be used in the layer 111Y(i,j). However, the present invention is not limited to these, and various known fluorescent materials can be used in the layer 111Y(i,j).

[0304] Specifically, 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′-diphenyl-N,N′-bis[4-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N′-bis(3-methylphenyl)-N,N′-bis[3-(9-phenyl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-bis[4-(9H-carbazol-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-carbazol-9-yl)-4'-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviation: YGAPA), : 2YGAPPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra(tert-butyl)perylene (abbreviation: TBP), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), N,N''-(2-tert-butylanthracene-9,10-diyldi-4,1-phenylene)bis[N,N',N '-triphenyl-1,4-phenylenediamine] (abbreviation: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: 2PCAPPA), N,N'-(pyrene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03), 3,10-bis[N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nbf(IV)-02), 3,10-bis[N-(dibenzofuran-3-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10FrA2Nbf(IV)-02), etc. can be used.

[0305] In particular, condensed aromatic diamine compounds typified by pyrenediamine compounds such as 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6BnfAPrn-03 are preferred because they have high hole trapping properties and are excellent in luminous efficiency or reliability.

[0306] Also, 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'''-octaphenyldibenzo[g,p]chrysene-2,7,10,15-tetraamine (abbreviation: DBC1), Coumarin 30, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-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) ... Nyl-1,4-phenylenediamine (abbreviation: 2DPAPA), 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-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-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), and the like can be used.

[0307] Further, 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]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N',N'-tetrakis(2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene)propanedinitrile (abbreviation: DCM3), (4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-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]ki] 2-{2-tert-butyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTB), 2-(2,6-bis{2-[4-(di 2-{2,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: BisDCM), 2-{2,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: BisDCJ™), and the like can be used.

[0308] [Phosphorescent Material] A phosphorescent material can be used in the layer 111Y(i,j). For example, the phosphorescent materials exemplified below can be used in the layer 111Y(i,j). Note that the present invention is not limited to these materials, and various known phosphorescent materials can be used in the layer 111Y(i,j).

[0309] For example, organometallic iridium complexes having a 4H-triazole skeleton, organometallic iridium complexes having a 1H-triazole skeleton, organometallic iridium complexes having an imidazole skeleton, organometallic iridium complexes having a phenylpyridine derivative having an electron-withdrawing group as a ligand, organometallic iridium complexes having a pyrimidine skeleton, organometallic iridium complexes having a pyrazine skeleton, organometallic iridium complexes having a pyridine skeleton, rare earth metal complexes, platinum complexes, and the like can be used for the layer 111Y(i, j).

[0310] [Phosphorescent Material (Blue)] Examples of organometallic iridium complexes having a 4H-triazole skeleton include tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN]phenyl-κC}iridium(III) (abbreviation: [Ir(mpptz-dmp) ３ ]), tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Mptz) ３ ]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPrptz-3b) ３ ]), etc. can be used.

[0311] Examples of organometallic iridium complexes having a 1H-triazole skeleton include tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(Mptz1-mp) ３ ]), tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Prptz1-Me) ３ ]), etc. can be used.

[0312] Examples of organometallic iridium complexes having an imidazole skeleton include fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpim) ３]), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmpimpt-Me) ３ ]), etc. can be used.

[0313] Examples of organometallic iridium complexes having a phenylpyridine derivative having an electron-withdrawing group as a ligand include bis[2-(4′,6′-difluorophenyl)pyridinato-N,C ２’ ]iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C ２’ ]iridium(III) picolinate (abbreviation: FIrpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N,C ２’} Iridium(III) picolinate (abbreviation: [Ir(CF ３ ppy) ２ (pic)]), bis[2-(4',6'-difluorophenyl)pyridinato-N,C ２’ ] Iridium (III) acetylacetonate (abbreviation: FIracac), etc. can be used.

[0314] These compounds exhibit blue phosphorescence and have a peak emission wavelength in the range of 440 nm to 520 nm.

[0315] [Phosphorescent Material (Green)] Examples of organometallic iridium complexes having a pyrimidine skeleton include 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-norbornyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(nbppm) ２ (acac)]), (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm) ２ (acac)]), (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm) ２ (acac)]), etc. can be used.

[0316] Examples of organometallic iridium complexes having a pyrazine skeleton include (acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-Me) ２ (acac)]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-iPr) ２ (acac)]), etc. can be used.

[0317] Examples of organometallic iridium complexes having a pyridine skeleton include 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(pq) ３ ]), bis(2-phenylquinolinato-N,C ２’ ) iridium(III) acetylacetonate (abbreviation: [Ir(pq) ２(acac)]), [2-d ３ -methyl-8-(2-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(5-d ３ -methyl-2-pyridinyl-κN ２ )phenyl-κC]iridium(III) (abbreviation: [Ir(5mppy-d ３ ) ２ (mbfpypy-d ３ ) )]), [2-d ３ [2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(ppy) ２ (mbfpypy-d ３ ) )]), etc. can be used.

[0318] Examples of rare earth metal complexes include tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [Tb(acac) ３ (Phen)]), etc.

[0319] These compounds mainly exhibit green phosphorescence, with a peak emission wavelength between 500 nm and 600 nm. Organometallic iridium complexes having a pyrimidine skeleton are also remarkably superior in reliability and luminous efficiency.

[0320] [Phosphorescent Material (Red)] Examples of organometallic iridium complexes having a pyrimidine skeleton include (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](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(dpm) ２ (dpm)]), etc. can be used.

[0321] Examples of organometallic iridium complexes having a pyrazine skeleton include (acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III) (abbreviation: [Ir(tppr) ２ (acac)]), bis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(tppr) ２ (dpm)]), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq) ２ (acac)]), etc. can be used.

[0322] Examples of organometallic iridium complexes having a pyridine skeleton include tris(1-phenylisoquinolinato-N,C ２’ ) Iridium(III) (abbreviation: [Ir(piq) ３ ]), bis(1-phenylisoquinolinato-N,C ２’ ) iridium(III) acetylacetonate (abbreviation: [Ir(piq) ２ (acac)]), etc. can be used.

[0323] Examples of rare earth metal complexes include tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: [Eu(DBM) ３ (Phen)]), tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: [Eu(TTA) ３ (Phen)]), etc. can be used.

[0324] As the platinum complex, for example, 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP) can be used.

[0325] These compounds exhibit red phosphorescence, with an emission peak at 600 nm to 700 nm. The organometallic iridium complexes having a pyrazine skeleton emit red light with a chromaticity suitable for use in display devices.

[0326] [Substance Exhibiting Thermally Activated Delayed Fluorescence (TADF)] A TADF material can be used for the layer 111Y(i,j). When a TADF material is used as a light-emitting material, the S1 level of the host material is preferably higher than the S1 level of the TADF material. In addition, the T1 level of the host material is preferably higher than the T1 level of the TADF material.

[0327] For example, the TADF materials listed below can be used as the light-emitting material. However, the light-emitting material is not limited to these, and various known TADF materials can be used.

[0328] In addition, the difference between the S1 and T1 levels of TADF materials is small, and reverse intersystem crossing (upconversion) from the triplet excited state to the singlet excited state can be achieved with a small amount of thermal energy. This allows efficient generation of the singlet excited state from the triplet excited state. Furthermore, the triplet excited energy can be converted into luminescence.

[0329] Furthermore, an exciplex (also called an exciplex) that forms an excited state with two types of substances has an extremely small difference between the S1 level and the T1 level, and functions as a TADF material that can convert triplet excitation energy into singlet excitation energy.

[0330] The T1 level can be determined by using a phosphorescence spectrum observed at low temperatures (e.g., 77 K to 10 K). When a tangent line is drawn at the base of the fluorescence spectrum on the short wavelength side of the TADF material, and the energy of the wavelength of the extrapolated line is defined as the S1 level, and when a tangent line is drawn at the base of the phosphorescence spectrum on the short wavelength side of the TADF material, and the energy of the wavelength of the extrapolated line is defined as the T1 level, the difference between the S1 level and the T1 level is preferably 0.3 eV or less, and more preferably 0.2 eV or less.

[0331] For example, TADF materials can include fullerene and its derivatives, acridine and its derivatives, eosin derivatives, etc. Also, metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), palladium (Pd), etc. can be used as TADF materials.

[0332] Specifically, protoporphyrin-tin fluoride complex (SnF), whose structural formula is shown below, ２ (Proto IX)), mesoporphyrin-tin fluoride complex (SnF ２ (Meso IX)), hematoporphyrin-tin fluoride complex (SnF ２ (Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complex (SnF ２ (Copro III-4Me)), octaethylporphyrin-tin fluoride complex (SnF ２ (OEP)), etioporphyrin-tin fluoride complex (SnF ２ (Etio I)), octaethylporphyrin-platinum chloride complex (PtCl ２ OEP), etc. can be used.

[0333]

[0334] Furthermore, for example, a heterocyclic compound having one or both of a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring can be used as the TADF material.

[0335] Specifically, the structural formulas of these compounds are as follows: 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ), 9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9′-phenyl-9H,9′H-3,3′-bicarbazole (abbreviation: PCCzTzn), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 2-[4-(10H-phenoxazin-10-yl)phenyl]-4 ,6-diphenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4-(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-dimethyl-9H-acridin-10-yl)-9H-xanthen-9-one (abbreviation: ACRXTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10′H-spiro[acridin-9,9′-anthracene]-10′-one (abbreviation: ACRSA), and the like can be used.

[0336]

[0337] The heterocyclic compound has a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring, and therefore has high electron transport and hole transport properties, and is therefore preferred. In particular, among skeletons having a π-electron-deficient heteroaromatic ring, pyridine skeletons, diazine skeletons (pyrimidine skeletons, pyrazine skeletons, pyridazine skeletons), and triazine skeletons are preferred because they are stable and reliable. In particular, benzofuropyrimidine skeletons, benzothienopyrimidine skeletons, benzofuropyrazine skeletons, and benzothienopyrazine skeletons are preferred because they have high electron acceptability and good reliability.

[0338] Among skeletons having a π-electron-rich heteroaromatic ring, it is preferable to have at least one of an acridine skeleton, a phenoxazine skeleton, a phenothiazine skeleton, a furan skeleton, a thiophene skeleton, and a pyrrole skeleton because they are stable and reliable. Note that the dibenzofuran skeleton is preferable as the furan skeleton, and the dibenzothiophene skeleton is preferable as the thiophene skeleton. Furthermore, the indole skeleton, the carbazole skeleton, the indolocarbazole skeleton, the bicarbazole skeleton, and the 3-(9-phenyl-9H-carbazol-3-yl)-9H-carbazole skeleton are particularly preferable as the pyrrole skeleton.

[0339] In addition, a substance in which a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring are directly bonded is particularly preferred because the electron-donating property of the π-electron-rich heteroaromatic ring and the electron-accepting property of the π-electron-deficient heteroaromatic ring are both strong, and the energy difference between the S1 level and the T1 level is small, thereby enabling efficient thermally activated delayed fluorescence to be obtained. In addition, an aromatic ring bonded to an electron-withdrawing group such as a cyano group may be used instead of the π-electron-deficient heteroaromatic ring. In addition, an aromatic amine skeleton, a phenazine skeleton, or the like may be used as the π-electron-rich skeleton.

[0340] Furthermore, examples of the π-electron-deficient skeleton that can be used include a xanthene skeleton, a thioxanthene dioxide skeleton, an oxadiazole skeleton, a triazole skeleton, an imidazole skeleton, an anthraquinone skeleton, a boron-containing skeleton such as phenylborane or boranthrene, an aromatic ring or heteroaromatic ring having a nitrile group or a cyano group such as benzonitrile or cyanobenzene, a carbonyl skeleton such as benzophenone, a phosphine oxide skeleton, and a sulfone skeleton.

[0341] In this way, a π-electron-deficient skeleton and a π-electron-rich skeleton can be used in place of at least one of a π-electron-deficient heteroaromatic ring and a π-electron-rich heteroaromatic ring.

[0342] <<Structure Example 2 of Layer 111Y(i,j)>> A material having carrier transport properties can be used as the host material. For example, a material having hole transport properties, a material having electron transport properties, a substance exhibiting thermally activated delayed fluorescence (TADF), a material having an anthracene skeleton, a mixed material, or the like can be used as the host material. Note that a structure in which a material having a larger band gap than the light-emitting material contained in the layer 111Y(i,j) is used as the host material is preferable. This can suppress energy transfer from excitons generated in the layer 111Y(i,j) to the host material.

[0343] [Material having hole transport properties] A material having a hole mobility of 1×10 −６ cm ２ For example, the material having a hole-transport property that can be used for the layer 112 can be used as the host material.

[0344] [Electron-Transporting Material] A metal complex or an organic compound having a π-electron-deficient heteroaromatic ring skeleton can be used as the electron-transporting material. For example, the electron-transporting material that can be used for the layer 113 can be used as the host material.

[0345] [Materials Having an Anthracene Skeleton] Organic compounds having an anthracene skeleton can be used as host materials. In particular, when a fluorescent material is used as the light-emitting material, organic compounds having an anthracene skeleton are suitable. This allows for the realization of light-emitting devices with good luminous efficiency and durability.

[0346] As the organic compound having an anthracene skeleton, an organic compound having a diphenylanthracene skeleton, particularly a 9,10-diphenylanthracene skeleton, is preferred because it is chemically stable. Furthermore, when the host material has a carbazole skeleton, it is preferred because it has improved hole injection and transport properties. In particular, when the host material contains a dibenzocarbazole skeleton, it is preferred because its HOMO level is shallower by about 0.1 eV than that of carbazole, making it easier for holes to enter, and it also has excellent hole transport properties and high heat resistance. From the viewpoint of hole injection and transport properties, a benzofluorene skeleton or a dibenzofluorene skeleton may be used instead of the carbazole skeleton.

[0347] Therefore, a substance having both a 9,10-diphenylanthracene skeleton and a carbazole skeleton, a substance having both a 9,10-diphenylanthracene skeleton and a benzocarbazole skeleton, or a substance having both a 9,10-diphenylanthracene skeleton and a dibenzocarbazole skeleton is preferable as the host material.

[0348] For example, 6-[3-(9,10-diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-[4-(9-phenyl-9H-fluoren-9-yl)biphenyl-4′-yl]anthracene (abbreviation: FLPPA), 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth), 9-phenyl-3-[4-(10-phenyl [4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA), 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), 3-[4-(1-naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), and the like can be used.

[0349] In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA exhibit very good properties.

[0350] [Substances Exhibiting Thermally Activated Delayed Fluorescence (TADF)] A TADF material can be used as a host material. When a TADF material is used as a host material, triplet excitation energy generated in the TADF material can be converted to singlet excitation energy by reverse intersystem crossing. Furthermore, the excitation energy can be transferred to a light-emitting material. In other words, the TADF material functions as an energy donor, and the light-emitting material functions as an energy acceptor. This can improve the luminous efficiency of a light-emitting device.

[0351] This is very effective when the luminescent material is a fluorescent luminescent material. Furthermore, in this case, in order to obtain high luminous efficiency, it is preferable that the S1 level of the TADF material is higher than the S1 level of the fluorescent luminescent material. Furthermore, it is preferable that the T1 level of the TADF material is higher than the S1 level of the fluorescent luminescent material. Therefore, it is preferable that the T1 level of the TADF material is higher than the T1 level of the fluorescent luminescent material.

[0352] It is also preferable to use a TADF material that emits light that overlaps with the wavelength of the lowest-energy absorption band of the fluorescent material, since this allows for smooth transfer of excitation energy from the TADF material to the fluorescent material, resulting in efficient light emission.

[0353] Furthermore, in order to efficiently generate singlet excitation energy from triplet excitation energy through reverse intersystem crossing, it is preferable that carrier recombination occurs in the TADF material. It is also preferable that the triplet excitation energy generated in the TADF material does not transfer to the triplet excitation energy of the fluorescent material. To this end, it is preferable that the fluorescent material has a protecting group around the luminophore (the skeleton responsible for luminescence) possessed by the fluorescent material. The protecting group is preferably a substituent that does not have a π bond, and is preferably a saturated hydrocarbon. Specific examples include alkyl groups having 3 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 carbon atoms, and trialkylsilyl groups having 3 to 10 carbon atoms. It is even more preferable that there are multiple protecting groups. Substituents that do not have a π bond have poor carrier transport function, so the distance between the TADF material and the luminophore of the fluorescent material can be increased without significantly affecting carrier transport or carrier recombination.

[0354] Here, the term "luminophore" refers to an atomic group (skeleton) that causes light emission in a fluorescent substance. The luminophore preferably has a skeleton having a π bond, preferably contains an aromatic ring, and preferably has a fused aromatic ring or a fused heteroaromatic ring.

[0355] Examples of the fused aromatic ring or fused heteroaromatic ring include a phenanthrene skeleton, a stilbene skeleton, an acridone skeleton, a phenoxazine skeleton, a phenothiazine skeleton, etc. In particular, fluorescent substances having a naphthalene skeleton, an anthracene skeleton, a fluorene skeleton, a chrysene skeleton, a triphenylene skeleton, a tetracene skeleton, a pyrene skeleton, a perylene skeleton, a coumarin skeleton, a quinacridone skeleton, or a naphthobisbenzofuran skeleton are preferred because of their high fluorescence quantum yield.

[0356] For example, a TADF material that can be used as a light-emitting material can be used as a host material.

[0357] [Configuration Example 1 of Mixed Material] A material obtained by mixing a plurality of substances can be used as the host material. For example, a material having electron transport properties and a material having hole transport properties can be used as the mixed material. The weight ratio of the material having hole transport properties to the material having electron transport properties contained in the mixed material may be set to (material having hole transport properties / material having electron transport properties) = (1 / 19) or more and (19 / 1) or less. This allows the carrier transport properties of the layer 111Y(i,j) to be easily adjusted. Furthermore, the recombination region can be easily controlled.

[0358] [Configuration Example 2 of Mixed Material] A material mixed with a phosphorescent material can be used as a host material. When a fluorescent material is used as an emitting material, the phosphorescent material can be used as an energy donor that provides excitation energy to the fluorescent material.

[0359] [Structure Example 3 of Mixed Material] A mixed material containing a material that forms an exciplex can be used as a host material. For example, a material whose emission spectrum of the formed exciplex overlaps with the wavelength of the lowest-energy absorption band of the light-emitting material can be used as a host material. This makes energy transfer smooth, thereby improving light-emitting efficiency. Alternatively, driving voltage can be suppressed. With such a structure, light emission can be efficiently obtained using Exciplex-Triple Energy Transfer (ExTET), which is energy transfer from the exciplex to the light-emitting material (phosphorescent material).

[0360] At least one of the materials forming the exciplex can be a phosphorescent material, which allows for the utilization of reverse intersystem crossing or the efficient conversion of triplet excitation energy to singlet excitation energy.

[0361] As a combination of materials for forming an exciplex, it is preferable that the HOMO level of the material having hole transport properties is equal to or higher than the HOMO level of the material having electron transport properties. Alternatively, it is preferable that the LUMO level of the material having hole transport properties is equal to or higher than the LUMO level of the material having electron transport properties. This allows for efficient formation of an exciplex. The LUMO level and HOMO level of the material can be derived from electrochemical properties (reduction potential and oxidation potential). Specifically, the reduction potential and oxidation potential can be measured using cyclic voltammetry (CV) measurement.

[0362] The formation of exciplexes can be confirmed, for example, by comparing the emission spectra of a material having hole transport properties, a material having electron transport properties, and a mixed film obtained by mixing these materials, and observing the phenomenon in which the emission spectrum of the mixed film is shifted to longer wavelengths than the emission spectra of each material (or has a new peak on the longer wavelength side). Alternatively, the formation of exciplexes can be confirmed by comparing the transient photoluminescence (PL) of a material having hole transport properties, the transient PL of a material having electron transport properties, and a mixed film obtained by mixing these materials, and observing differences in transient response, such as the transient PL lifetime of the mixed film having a longer-lifetime component or a larger proportion of delayed components than the transient PL lifetimes of the individual materials. The above-mentioned transient PL may also be interpreted as transient electroluminescence (EL). In other words, the formation of exciplexes can also be confirmed by comparing the transient EL of a material having hole transport properties, the transient EL of a material having electron transport properties, and a mixed film obtained by mixing these materials, and observing the differences in transient response.

[0363] <Configuration Example 2 of Display Device 700> The display device 700 described in this embodiment includes an insulating film 528 (see FIG. 3A).

[0364] <<Configuration Example of Insulating Film 528>> The insulating film 528 has openings, one of which overlaps with the electrode 551X(i,j) and the other of which overlaps with the electrode 551Y(i,j). The insulating film 528 also overlaps with the gap 551XY(i,j).

[0365] <<Configuration Example of Gap 551XY(i,j)>> The gap 551XY(i,j) sandwiched between the electrode 551X(i,j) and the electrode 551Y(i,j) has, for example, a groove-like shape. This forms a step along the groove. Furthermore, a discontinuity or a thin film thickness is formed between the film deposited on the gap 551XY(i,j) and the film deposited on the electrode 551X(i,j).

[0366] For example, when an anisotropic film formation method such as a thermal evaporation method is used, a discontinuity or a thin film thickness is formed along the step in the region 104XY(i,j) sandwiched between the layer 104X(i,j) and the layer 104Y(i,j).

[0367] This can suppress, for example, the current flowing through the region 104XY(i,j). It can also suppress the current flowing between the layer 104X(i,j) and the layer 104Y(i,j). It can also suppress the phenomenon in which the adjacent light-emitting device 550Y(i,j) unintentionally emits light due to the operation of the light-emitting device 550X(i,j).

[0368] <Configuration Example 3 of Display Device 700> The display device 700 described in this embodiment includes a light-emitting device 550X(i,j) and a light-emitting device 550Y(i,j) (see FIG. 3B). The light-emitting device 550Y(i,j) is adjacent to the light-emitting device 550X(i,j).

[0369] 3A , the display device 700 differs from the display device 700 described using FIG. 3A in that part or all of the configuration of the light-emitting device 550X(i,j) or the light-emitting device 550Y(i,j) is removed in the portion overlapping the gap 551XY(i,j), that discontinuities or thin portions are formed in the region 106XY1(i,j) and the region 106XY2(i,j), and that films 529_1, 529_2, and 529_3 are provided instead of the insulating film 528. Here, the different portions will be described in detail, and the above description will be used for the portions having the same configuration.

[0370] <<Configuration Example of the Film 529_1>> The film 529_1 has openings, one of which overlaps with the electrode 551X(i,j) and the other of which overlaps with the electrode 551Y(i,j) (see FIG. 3B ). The film 529_1 also has openings that overlap with the gaps 551XY(i,j). For example, a film containing a metal, a metal oxide, an organic material, or an inorganic insulating material can be used for the film 529_1. Specifically, a light-blocking metal film can be used. This can protect the light-emitting device from light irradiated during the processing step.

[0371] The film 529_2 has openings, one of which overlaps with the electrode 551X(i, j) and the other of which overlaps with the electrode 551Y(i, j). The film 529_2 also overlaps with the gap 551XY(i, j).

[0372] The film 529_2 has a region in contact with the layer 104X(i,j) and the unit 103X(i,j).

[0373] The film 529_2 also has a region in contact with the layer 104Y(i,j) and the unit 103Y(i,j).

[0374] The film 529_2 has a region in contact with the insulating film 521. For example, the film 529_2 can be formed by atomic layer deposition (ALD). This allows a film with good coverage to be formed. Specifically, a metal oxide film or the like can be used for the film 529_2. For example, aluminum oxide can be used.

[0375] <<Configuration Example of the Film 529_3>> The film 529_3 has openings, one of which overlaps with the electrode 551X(i,j) and the other of which overlaps with the electrode 551Y(i,j). The film 529_3 fills a groove formed in the region overlapping with the gap 551XY(i,j). For example, the film 529_3 can be formed using a photosensitive resin. Specifically, an acrylic resin or the like can be used.

[0376] This allows, for example, electrical insulation between the layer 104X(i,j) and the layer 104Y(i,j). It also allows, for example, suppression of current flowing through the region 104XY(i,j). It also allows suppression of the phenomenon in which the adjacent light-emitting device 550Y(i,j) unintentionally emits light due to operation of the light-emitting device 550X(i,j). It also allows reduction of the size of the step between the upper surface of the unit 103X(i,j) and the upper surface of the unit 103Y(i,j). It also allows suppression of the phenomenon in which a discontinuity or a thin portion is formed between the electrode 552X(i,j) and the electrode 552Y(i,j). It also allows the use of a single conductive film for the electrode 552X(i,j) and the electrode 552Y(i,j).

[0377] For example, photolithography can be used to remove part or all of the components that can be used in light-emitting device 550X(i,j) or light-emitting device 550Y(i,j) from the portion that overlaps gap 551XY(i,j). In this specification, etc., a device fabricated using a metal mask or a fine metal mask (FMM) may be referred to as a device with an MM (metal mask) structure. Also, in this specification, etc., a device fabricated without using a metal mask or an FMM may be referred to as a device with an MML (metal maskless) structure.

[0378] In a fabrication method using a fine metal mask, it is difficult to reduce the spacing between adjacent light-emitting devices to, for example, less than 10 μm. In a fabrication method using photolithography on a glass substrate, the spacing between adjacent light-emitting devices can be reduced to, for example, less than 10 μm, 5 μm or less, 3 μm or less, 2 μm or less, 1.5 μm or less, 1 μm or less, or 0.5 μm or less. In a fabrication method using photolithography on a silicon wafer, for example, using an exposure device designed for LSIs, the spacing between adjacent light-emitting devices can be reduced to 500 nm or less, 200 nm or less, 100 nm or less, or even 50 nm or less.

[0379] This allows the area of ​​a non-light-emitting region between adjacent light-emitting devices to be significantly reduced, and also allows the aperture ratio to approach 100%. For example, in a display device according to one embodiment of the present invention, the aperture ratio can be 40% or more, 50% or more, 60% or more, 70% or more, 80% or more, or even 90% or more, but less than 100%.

[0380] Specifically, in the first step, a film that will later become the unit 103Y(i,j) is formed on the gap 551XY(i,j).

[0381] In a second step, a first film, which will become film 529_1, is formed on the film that will become unit 103Y(i,j).

[0382] In a third step, openings overlapping the gaps 551XY(i,j) are formed in the first film using photolithography.

[0383] In the fourth step, the first film is used as a resist to remove part or all of the components of the light-emitting device 550Y(i,j) from the region overlapping the gap 551XY(i,j). For example, the unit 103Y is removed using a dry etching method. Specifically, the organic compound can be removed using a gas containing oxygen. As a result, a groove-like structure is formed in the region overlapping the gap 551XY(i,j).

[0384] In a fifth step, a second film, which will become film 529_2, is formed on the first film, for example, using atomic layer deposition (ALD).

[0385] In a sixth step, a film 529_3 is formed using, for example, a photosensitive polymer, so that the film 529_3 fills the groove-like structure formed in the region overlapping the gap 551XY(i, j).

[0386] In a seventh step, openings that overlap the electrode 551Y(i,j) are formed in the first film and the second film by photolithography to form films 529_1 and 529_2.

[0387] In the eighth step, a layer 105Y(i,j) is formed on the unit 103Y2(i,j), and an electrode 552Y(i,j) is formed on the layer 105Y(i,j).

[0388] Note that this embodiment mode can be appropriately combined with other embodiment modes described in this specification.

[0389] Embodiment 8 In this embodiment, a structure of a display device 700 of one embodiment of the present invention will be described with reference to FIGS. 4A and 4B.

[0390] FIG. 4A is a cross-sectional view illustrating a structure of a display device 700 of one embodiment of the present invention, and FIG. 4B is a cross-sectional view illustrating a structure of the display device 700 of one embodiment of the present invention, which is different from that in FIG. 4A .

[0391] <Configuration Example 1 of Display Device 700> The display device 700 described in this embodiment includes a light-emitting device 550X(i,j) and a photoelectric conversion device 550S(i,j) (see FIG. 4A). The photoelectric conversion device 550S(i,j) is adjacent to the light-emitting device 550X(i,j).

[0392] The display device 700 also has a substrate 510 and a functional layer 520. The functional layer 520 includes an insulating film 521, and the light-emitting device 550X(i, j) and the light-emitting device 550Y(i, j) are formed on the insulating film 521. The functional layer 520 is sandwiched between the substrate 510 and the light-emitting device 550X(i, j).

[0393] <<Configuration Example of Light-Emitting Device 550X(i,j)>> The light-emitting device 550X(i,j) has an electrode 551X(i,j), an electrode 552X(i,j), and a unit 103X(i,j). The electrode 552X(i,j) overlaps the electrode 551X(i,j), and the unit 103X(i,j) is sandwiched between the electrode 552X(i,j) and the electrode 551X(i,j). The light-emitting device 550X(i,j) also has a layer 104X(i,j) and a layer 105X(i,j), and the layer 104X(i,j) is sandwiched between the unit 103X(i,j) and the electrode 551X(i,j), and the layer 105X(i,j) is sandwiched between the electrode 552X(i,j) and the unit 103X(i,j).

[0394] For example, the light-emitting device 550X described in any of Embodiments 2 to 6 can be used for the light-emitting device 550X(i, j). Specifically, a structure that can be used for the electrode 551X can be used for the electrode 551X(i, j), and a structure that can be used for the electrode 552X can be used for the electrode 552X(i, j). A structure that can be used for the unit 103X can be used for the unit 103X(i, j). A structure that can be used for the layer 104 can be used for the layer 104X(i, j), and a structure that can be used for the layer 105 can be used for the layer 105X(i, j).

[0395] <<Configuration Example of Photoelectric Conversion Device 550S(i,j)>> The photoelectric conversion device 550S(i,j) has an electrode 551S(i,j), an electrode 552S(i,j), and a unit 103S(i,j). The electrode 552S(i,j) overlaps with the electrode 551S(i,j), and the unit 103S(i,j) is sandwiched between the electrode 552S(i,j) and the electrode 551S(i,j). Furthermore, photoelectric conversion device 550S(i,j) has layer 104S(i,j) and layer 105S(i,j), layer 104S(i,j) is sandwiched between unit 103S(i,j) and electrode 551S(i,j), and layer 105S(i,j) is sandwiched between electrode 552S(i,j) and unit 103S(i,j).

[0396] The electrode 551S(i,j) is adjacent to the electrode 551X(i,j), and there is a gap 551XS(i,j) between the electrode 551S(i,j) and the electrode 551X(i,j).

[0397] Note that part of the structure that can be used for the light-emitting device 550X(i,j) described in any of Embodiments 2 to 6 can be used for the photoelectric conversion device 550S(i,j). For example, part of the conductive film that can be used for the electrode 552X(i,j) can be used for the electrode 552S(i,j), and part of the structure that can be used for the electrode 551X can be used for the electrode 551S(i,j). Furthermore, part of the structure that can be used for the layer 104 can be used for the layer 104S(i,j), and part of the structure that can be used for the layer 105 can be used for the layer 105S(i,j). This allows part of the structure to be shared. Furthermore, the manufacturing process can be simplified.

[0398] Note that photoelectric conversion device 550S(i,j) differs from light-emitting device 550X(i,j) in that it has unit 103S(i,j) having a function of converting light into electric current, instead of unit 103X(i,j) having a function of emitting light. Here, the differences will be described in detail, and the above description will be used for the parts having the same configuration.

[0399] <<Configuration Example of Unit 103S(i,j)>> The unit 103S(i,j) has a single-layer structure or a laminated structure. For example, in addition to a photoelectric conversion layer, a layer selected from functional layers such as a hole transport layer, an electron transport layer, and a carrier block layer can be used for the unit 103S(i,j).

[0400] Unit 103S(i,j) comprises layer 114S(i,j), layer 112S(i,j), and layer 113S(i,j) (see FIG. 4A). Layer 114S(i,j) is sandwiched between layer 112S(i,j) and layer 113S(i,j). Note that layer 112S(i,j) is sandwiched between electrode 551S(i,j) and layer 114S(i,j), and layer 113S(i,j) is sandwiched between electrode 552S(i,j) and layer 114S(i,j).

[0401] The unit 103S(i,j) has a function of absorbing light hv and supplying electrons to one electrode and holes to the other electrode. For example, the unit 103S(i,j) supplies holes to the electrode 551S(i,j) and electrons to the electrode 552S(i,j).

[0402] Note that part of the structure that can be used for the unit 103X described in Embodiment 2 can be used for the structure of the unit 103S(i,j). For example, a structure that can be used for the layer 112 can be used for the layer 112S(i,j), and a structure that can be used for the layer 113 can be used for the layer 113S(i,j). This allows part of the structure to be shared. Furthermore, the manufacturing process can be simplified.

[0403] <<Configuration Example 1 of Layer 114S(i,j)>> The layer 114S(i,j) can be referred to as a photoelectric conversion layer. The layer 114S(i,j) absorbs light hv and supplies electrons to a layer in contact with one side and holes to a layer in contact with the other side. For example, the layer 114S(i,j) supplies holes to the layer 112 and electrons to the layer 113. For example, a material that can be used in an organic solar cell can be used for the layer 114S(i,j). Specifically, an electron-accepting material and an electron-donating material can be used for the layer 114S(i,j).

[0404] [Examples of Electron Accepting Materials] For example, fullerene derivatives, non-fullerene electron acceptors, etc. can be used as the electron accepting material.

[0405] Examples of electron-accepting materials include C ６０ Fullerene, C ７０ Fullerene, [6,6]-phenyl-C ７１ -Butyric acid methyl ester (abbreviation: PC71BM), [6,6]-phenyl-C ６１ -butyric acid methyl ester (abbreviation: PC61BM), 1',1'',4',4''-tetrahydro-di[1,4]methanonaphthaleno[1,2:2',3',56,60:2'',3''][5,6]fullerene-C ６０ (abbreviation: ICBA) etc. can be used.

[0406] Examples of non-fullerene electron acceptors that can be used include perylene derivatives, compounds having a dicyanomethyleneindanone group, and N,N'-dimethyl-3,4,9,10-perylenedicarboximide (abbreviation: Me-PTCDI).

[0407] [Examples of Electron-Donating Materials] For example, phthalocyanine compounds, tetracene derivatives, quinacridone derivatives, rubrene derivatives, etc. can be used as electron-donating materials.

[0408] Examples of electron-donating materials that can be used include copper (II) phthalocyanine (abbreviation: CuPc), tin (II) phthalocyanine (abbreviation: SnPc), zinc phthalocyanine (abbreviation: ZnPc), tetraphenyldibenzoperiflanthene (abbreviation: DBP), and rubrene.

[0409] <<Configuration Example 2 of Layer 114S(i,j)>> For example, a single-layer structure or a stacked structure can be used for the layer 114S(i,j). Specifically, a bulk heterojunction structure can be used for the layer 114S(i,j). Alternatively, a heterojunction structure can be used for the layer 114S(i,j).

[0410] [Example of Bulk Heterojunction] For example, a mixed material containing an electron-accepting material and an electron-donating material can be used for the layer 114S(i,j) (see FIG. 4A). Note that a structure in which a mixed material containing an electron-accepting material and an electron-donating material is used for the layer 114S(i,j) can be referred to as a bulk heterojunction.

[0411] Specifically, C ７０ A mixed material including fullerenes and DBPs can be used for layer 114S(i,j).

[0412] [Heterojunction Example] Layer 114N(i,j) and layer 114P(i,j) can be used for layer 114S(i,j) (see FIG. 4B). Layer 114N(i,j) is sandwiched between one electrode and layer 114P(i,j), and layer 114P(i,j) is sandwiched between layer 114N(i,j) and the other electrode. For example, layer 114N(i,j) is sandwiched between electrode 552S(i,j) and layer 114P(i,j), and layer 114P(i,j) is sandwiched between layer 114N(i,j) and electrode 551S(i,j).

[0413] An n-type semiconductor can be used for the layer 114N(i,j). For example, Me-PTCDI can be used for the layer 114N(i,j).

[0414] Alternatively, a p-type semiconductor can be used for the layer 114P(i,j). For example, rubrene can be used for the layer 114P(i,j).

[0415] The photoelectric conversion device 550S(i,j) having a configuration in which the layer 114P(i,j) is in contact with the layer 114N(i,j) can be called a PN junction photodiode.

[0416] Embodiment 9 In this embodiment, a structure of a device according to one embodiment of the present invention will be described with reference to FIGS.

[0417] 5A and 5B are diagrams illustrating a configuration of a device according to one embodiment of the present invention. Fig. 5A is a top view of the device according to one embodiment of the present invention, and Fig. 5B is a top view illustrating a part of Fig. 5A. Fig. 5C is a cross-sectional view along the cutting lines X1-X2 and X3-X4 and along a pair of pixels 703(i, j) illustrated in Fig. 5A.

[0418] FIG. 6 is a circuit diagram illustrating a configuration of a device according to one embodiment of the present invention.

[0419] 7A and 7B are diagrams illustrating a configuration of a device according to one embodiment of the present invention, in which Fig. 7A is a cross-sectional view of the device according to one embodiment of the present invention, and Fig. 7B is a cross-sectional view different from Fig. 7A.

[0420] <Configuration Example 1 of Display Device 700> A display device 700 of one embodiment of the present invention includes a region 231 (see FIG. 5A ). The region 231 includes a set of pixels 703(i, j).

[0421] <<Configuration Example of a Set of Pixels 703(i,j)>> A set of pixels 703(i,j) includes a pixel 702X(i,j) (see FIGS. 5B and 5C).

[0422] The pixel 702X(i,j) includes a pixel circuit 530X(i,j) and a light-emitting device 550X(i,j). The light-emitting device 550X(i,j) is electrically connected to the pixel circuit 530X(i,j).

[0423] For example, any of the light-emitting devices described in any of Embodiments 2 to 6 can be used as the light-emitting device 550X(i, j). The display device 700 has a function of displaying an image.

[0424] <Structure Example 2 of Display Device 700> A display device 700 of one embodiment of the present invention includes a functional layer 540 and a functional layer 520 (see FIG. 5C).

[0425] The functional layer 540 includes a light-emitting device 550X(i,j).

[0426] The functional layer 520 includes pixel circuits 530X(i,j) and wiring (see FIG. 5C ). The pixel circuits 530X(i,j) are electrically connected to the wiring. For example, a conductive film provided in the opening 591X or the opening 591Y of the functional layer 520 can be used for the wiring. The wiring electrically connects the terminal 519B and the pixel circuit 530X(i,j). A conductive material CP electrically connects the terminal 519B and the flexible printed circuit FPC1.

[0427] <Structure Example 3 of Display Device 700> The display device 700 of one embodiment of the present invention includes a driver circuit GD and a driver circuit SD (see FIG. 5A).

[0428] <<Configuration Example of the Driver Circuit GD>> The driver circuit GD supplies a first selection signal and a second selection signal.

[0429] <<Configuration Example of Driver Circuit SD>> The driver circuit SD supplies a first control signal and a second control signal.

[0430] <<Wiring Configuration Example 1>> The wiring includes conductive film G1(i), conductive film G2(i), conductive film S1(j), conductive film S2(j), conductive film ANO, conductive film VCOM2, and conductive film V0 (see FIG. 6).

[0431] The conductive film G1(i) is supplied with a first selection signal, and the conductive film G2(i) is supplied with a second selection signal.

[0432] The conductive film S1(j) is supplied with a first control signal, and the conductive film S2(j) is supplied with a second control signal.

[0433] <<Configuration Example 1 of Pixel Circuit 530X(i,j)>> The pixel circuit 530X(i,j) is electrically connected to a conductive film G1(i) and a conductive film S1(j). The conductive film G1(i) supplies a first selection signal, and the conductive film S1(j) supplies a first control signal.

[0434] The pixel circuit 530X(i,j) drives the light-emitting device 550X(i,j) based on the first selection signal and the first control signal. The light-emitting device 550X(i,j) emits light.

[0435] The light emitting device 550X(i,j) has one electrode electrically connected to the pixel circuit 530X(i,j) and the other electrode electrically connected to the conductive film VCOM2.

[0436] <<Configuration Example 2 of Pixel Circuit 530X(i,j)>> The pixel circuit 530X(i,j) includes a switch SW21, a switch SW22, a transistor M21, a capacitor C21, and a node N21.

[0437] The transistor M21 has a gate electrode electrically connected to the node N21, a first electrode electrically connected to the light-emitting device 550X(i, j), and a second electrode electrically connected to the conductive film ANO.

[0438] The switch SW21 has a first terminal electrically connected to the node N21, a second terminal electrically connected to the conductive film S1(j), and a gate electrode having the function of controlling the conductive state or non-conductive state based on the potential of the conductive film G1(i).

[0439] The switch SW22 includes a first terminal electrically connected to the conductive film S2(j) and a gate electrode having a function of controlling the conductive state or non-conductive state based on the potential of the conductive film G2(i).

[0440] The capacitor C21 includes a conductive film electrically connected to the node N21 and a conductive film electrically connected to the second electrode of the switch SW22.

[0441] This allows an image signal to be stored in node N21. Alternatively, the potential of node N21 can be changed using switch SW22. Alternatively, the intensity of light emitted by light-emitting device 550X(i, j) can be controlled using the potential of node N21. As a result, a novel device with excellent convenience, usability, and reliability can be provided.

[0442] <<Configuration Example 3 of Pixel Circuit 530X(i,j)>> The pixel circuit 530X(i,j) includes a switch SW23, a node N22, and a capacitor C22.

[0443] The switch SW23 has a first terminal electrically connected to the conductive film V0, a ​​second terminal electrically connected to the node N22, and a gate electrode having the function of controlling the conductive state or non-conductive state based on the potential of the conductive film G2(i).

[0444] The capacitor C22 includes a conductive film electrically connected to the node N21 and a conductive film electrically connected to the node N22.

[0445] The first electrode of the transistor M21 is electrically connected to a node N22.

[0446] <<Configuration Example 1 of Pixel 702X(i,j)>> The pixel 702X(i,j) includes a light-emitting device 550X(i,j) and a pixel circuit 530X(i,j) (see FIG. 7A ). The functional layer 540 includes the light-emitting device 550X(i,j) and the colored layer CFX, and the functional layer 520 includes the pixel circuit 530X(i,j).

[0447] The light-emitting device 550X(i,j) is a top-emission type light-emitting device, and the light-emitting device 550X(i,j) emits light ELX to the side where the functional layer 520 is not arranged.

[0448] The coloring layer CFX transmits a portion of the light emitted by the light-emitting device 550X(i, j). For example, it can transmit a portion of white light and extract blue, green, or red light. Note that a color conversion layer can be used instead of the coloring layer CFX. This allows light with a short wavelength to be converted into light with a long wavelength.

[0449] 7B, the pixel 702X(i,j) includes a bottom-emission light-emitting device 550X(i,j). The light-emitting device 550X(i,j) emits light ELX toward the side where the functional layer 520 is disposed.

[0450] The functional layer 520 includes a region 520T that transmits light ELX. The functional layer 520 also includes a colored layer CFX that overlaps the region 520T.

[0451] Note that this embodiment mode can be appropriately combined with other embodiment modes described in this specification.

[0452] Embodiment Mode 10 In this embodiment mode, a light-emitting device using the light-emitting device described in any one of Embodiment Modes 2 to 6 will be described.

[0453] In this embodiment, a light-emitting device manufactured using the light-emitting device described in any one of Embodiments 2 to 6 will be described with reference to Fig. 8. Fig. 8A is a top view showing the light-emitting device, and Fig. 8B is a cross-sectional view taken along lines A-B and C-D in Fig. 8A. This light-emitting device has a pixel portion 602 and a driver circuit portion indicated by dotted lines to control light emission from the light-emitting device, and the driver circuit portion includes a source line driver circuit 601 and a gate line driver circuit 603. The light-emitting device also includes a sealing substrate 604 and a sealant 605, and the sealant 605 surrounds a space 607.

[0454] The routing wiring 608 is wiring for transmitting signals input to the source line driver circuit 601 and the gate line driver circuit 603, and receives video signals, clock signals, start signals, reset signals, etc. from an FPC (flexible print circuit) that serves as an external input terminal 609. Although only the FPC is shown here, a printed wiring board (PWB) may be attached to this FPC. In this specification, the light-emitting device includes not only the light-emitting device itself but also a state in which an FPC or PWB is attached to it.

[0455] Next, the cross-sectional structure will be described with reference to Fig. 8B. A driver circuit portion and a pixel portion are formed on an element substrate 610, and here, a source line driver circuit 601, which is the driver circuit portion, and one pixel in a pixel portion 602 are shown.

[0456] The element substrate 610 may be made of a substrate made of glass, quartz, organic resin, metal, alloy, semiconductor, or the like, or a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (Polyvinyl Fluoride), polyester, acrylic resin, or the like.

[0457] The structure of a transistor used in a pixel or a driver circuit is not particularly limited. For example, an inverted staggered transistor or a staggered transistor may be used. Furthermore, a top-gate transistor or a bottom-gate transistor may be used. The semiconductor material used for the transistor is not particularly limited, and examples thereof include silicon, germanium, silicon carbide, and gallium nitride. Alternatively, an oxide semiconductor containing at least one of indium, gallium, and zinc, such as an In—Ga—Zn-based metal oxide, may be used.

[0458] The crystallinity of a semiconductor material used for a transistor is not particularly limited, and any of an amorphous semiconductor and a crystalline semiconductor (a microcrystalline semiconductor, a polycrystalline semiconductor, a single crystal semiconductor, or a semiconductor having a crystalline region in part) may be used. The use of a crystalline semiconductor is preferable because it can suppress deterioration of transistor characteristics.

[0459] Here, it is preferable to use an oxide semiconductor for the transistors provided in the pixel or the driver circuit, as well as for semiconductor devices such as transistors used in touch sensors, which will be described later. In particular, it is preferable to use an oxide semiconductor having a wider band gap than silicon. By using an oxide semiconductor having a wider band gap than silicon, the current in the off state of the transistor can be reduced.

[0460] The oxide semiconductor preferably contains at least indium (In) or zinc (Zn), and more preferably contains an oxide represented by In-M-Zn-based oxide (M is a metal such as Al, Ti, Ga, Ge, Y, Zr, Sn, La, Ce, or Hf).

[0461] In particular, it is preferable to use, as the semiconductor layer, an oxide semiconductor film which has a plurality of crystal parts whose c-axes are oriented perpendicular to a surface on which the semiconductor layer is formed or a top surface of the semiconductor layer and which does not have grain boundaries between adjacent crystal parts.

[0462] By using such a material for the semiconductor layer, fluctuations in electrical characteristics are suppressed, and a highly reliable transistor can be realized.

[0463] Furthermore, a transistor having the above-described semiconductor layer can retain charge stored in a capacitor through the transistor for a long period of time due to its low off-state current. By applying such a transistor to a pixel, it is possible to stop the driver circuit while maintaining the gray level of an image displayed in each display region. As a result, an electronic device with extremely low power consumption can be realized.

[0464] For example, to stabilize the characteristics of a transistor, it is preferable to provide a base film. The base film can be formed as a single layer or a stacked layer using an inorganic insulating film such as a silicon oxide film, a silicon nitride film, a silicon oxynitride film, or a silicon nitride oxide film. The base film can be formed by a sputtering method, a CVD (Chemical Vapor Deposition) method (such as a plasma CVD method, a thermal CVD method, or a MOCVD (Metal Organic CVD) method), an ALD (Atomic Layer Deposition) method, a coating method, a printing method, or the like. Note that the base film need not be provided if it is not necessary.

[0465] Note that the FET 623 represents one of the transistors formed in the source line driver circuit 601. The driver circuit may be formed of various CMOS circuits, PMOS circuits, or NMOS circuits. In addition, although this embodiment shows a driver-integrated type in which the driver circuit is formed on a substrate, this is not necessarily required, and the driver circuit may also be formed externally rather than on the substrate.

[0466] Furthermore, the pixel portion 602 is formed by a plurality of pixels including a switching FET 611, a current control FET 612, and a first electrode 613 electrically connected to the drain of the FET, but is not limited to this, and the pixel portion may be formed by combining three or more FETs and a capacitance element.

[0467] An insulator 614 is formed to cover an end portion of the first electrode 613. Here, the insulator 614 can be formed by using a positive photosensitive acrylic resin film.

[0468] Furthermore, in order to improve the coverage of an EL layer or the like to be formed later, a curved surface having a curvature is formed at the upper or lower end of the insulator 614. For example, when a positive photosensitive acrylic resin is used as the material of the insulator 614, it is preferable that only the upper end of the insulator 614 has a curved surface having a curvature radius (0.2 μm or more and 3 μm or less). Furthermore, either a negative photosensitive resin or a positive photosensitive resin can be used as the insulator 614.

[0469] An EL layer 616 and a second electrode 617 are formed on the first electrode 613. Here, it is desirable to use a material with a large work function as the material used for the first electrode 613, which functions as an anode. For example, a single layer film such as an ITO film, an indium tin oxide film containing silicon, an indium oxide film containing 2 wt % to 20 wt % of zinc oxide, a titanium nitride film, a chromium film, a tungsten film, a Zn film, or a Pt film can be used. It is also possible to use a stacked structure of a titanium nitride film and a film mainly composed of aluminum, or a three-layer structure of a titanium nitride film, a film mainly composed of aluminum, and a titanium nitride film. The stacked structure provides low resistance as a wiring, good ohmic contact, and the first electrode 613 can function as an anode.

[0470] The EL layer 616 is formed by various methods such as an evaporation method using an evaporation mask, an ink-jet method, or a spin coating method. The EL layer 616 has the structure described in any one of Embodiments 2 to 6. Other materials constituting the EL layer 616 may be low-molecular-weight compounds or high-molecular-weight compounds (including oligomers and dendrimers).

[0471] Furthermore, as a material used for the second electrode 617 formed on the EL layer 616 and functioning as a cathode, a material having a small work function (Al, Mg, Li, Ca, or an alloy or compound thereof (MgAg, MgIn, AlLi, etc.)) is preferably used. Note that, when light generated in the EL layer 616 is transmitted through the second electrode 617, it is preferable to use a stack of a thin metal thin film and a transparent conductive film (ITO, indium oxide containing 2 wt % to 20 wt % zinc oxide, indium tin oxide containing silicon, zinc oxide (ZnO), etc.) as the second electrode 617.

[0472] Note that a light-emitting device is formed with the first electrode 613, the EL layer 616, and the second electrode 617. The light-emitting device is the light-emitting device described in any one of Embodiments 2 to 6. Note that a plurality of light-emitting devices are formed in the pixel portion, and the light-emitting device in this embodiment may include both the light-emitting device described in any one of Embodiments 2 to 6 and light-emitting devices having other structures.

[0473] Furthermore, by bonding the sealing substrate 604 to the element substrate 610 with a sealing material 605, a structure is formed in which a light-emitting device 618 is provided in a space 607 surrounded by the element substrate 610, the sealing substrate 604, and the sealing material 605. The space 607 is filled with a filler, and in some cases, the space is filled with an inert gas (nitrogen, argon, etc.), or with a sealing material. Although not shown in Fig. 8B, a recess is formed in the sealing substrate and a desiccant is provided therein, which is a preferable configuration because it can suppress deterioration due to the influence of moisture.

[0474] It is preferable to use an epoxy resin or glass frit for the sealing material 605. It is also desirable that these materials be moisture and oxygen impermeable as much as possible. The sealing substrate 604 may be made of a glass substrate, a quartz substrate, or a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (Polyvinyl Fluoride), polyester, acrylic resin, or the like.

[0475] Although not shown in Figures 8A and 8B, a protective film may be provided on the second electrode. The protective film may be formed of an organic resin film or an inorganic insulating film. The protective film may also be formed so as to cover the exposed portion of the sealing material 605. The protective film may also be provided so as to cover the surfaces and side surfaces of the pair of substrates, the exposed side surfaces of the sealing layer, the insulating layer, etc.

[0476] The protective film can be made of a material that is impermeable to impurities such as water, and therefore can effectively prevent impurities such as water from diffusing from the outside to the inside.

[0477] The protective film may be made of an oxide, nitride, fluoride, sulfide, ternary compound, metal, polymer, or the like. For example, a material containing aluminum oxide, hafnium oxide, hafnium silicate, lanthanum oxide, silicon oxide, strontium titanate, tantalum oxide, titanium oxide, zinc oxide, niobium oxide, zirconium oxide, tin oxide, yttrium oxide, cerium oxide, scandium oxide, erbium oxide, vanadium oxide, indium oxide, or the like; a material containing aluminum nitride, hafnium nitride, silicon nitride, tantalum nitride, titanium nitride, niobium nitride, molybdenum nitride, zirconium nitride, gallium nitride, or the like; a nitride containing titanium and aluminum; an oxide containing titanium and aluminum; an oxide containing aluminum and zinc; a sulfide containing manganese and zinc; a sulfide containing cerium and strontium; an oxide containing erbium and aluminum; or an oxide containing yttrium and zirconium.

[0478] The protective film is preferably formed using a film formation method that provides good step coverage. One such method is atomic layer deposition (ALD). It is preferable to use a material that can be formed using the ALD method for the protective film. By using the ALD method, it is possible to form a dense protective film with reduced defects such as cracks or pinholes, or with a uniform thickness. Furthermore, it is possible to reduce damage to the workpiece when forming the protective film.

[0479] For example, by forming a protective film using the ALD method, it is possible to form a uniform protective film with few defects on a surface having a complex uneven shape or on the top, side and back surfaces of a touch panel.

[0480] In the above manner, a light-emitting device manufactured using the light-emitting device described in any one of Embodiments 2 to 6 can be obtained.

[0481] The light-emitting device in this embodiment can have favorable characteristics because it uses the light-emitting device described in any one of Embodiments 2 to 6. Specifically, the light-emitting device described in any one of Embodiments 2 to 6 has favorable emission efficiency, and therefore can have low power consumption.

[0482] 9A shows an example of a full-color light-emitting device in which a light-emitting device that emits white light is formed and a colored layer (color filter) is provided, etc. Fig. 9A illustrates a substrate 1001, a base insulating film 1002, a gate insulating film 1003, a gate electrode 1006, a gate electrode 1007, a gate electrode 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, an electrode 1024W, an electrode 1024R, an electrode 1024G, an electrode 1024B of the light-emitting device, a partition wall 1025, an EL layer 1028, an electrode 1029 of the light-emitting device, a sealing substrate 1031, a sealant 1032, etc.

[0483] 9A , the colored layers (red colored layer 1034R, green colored layer 1034G, and blue colored layer 1034B) are provided on a transparent base material 1033. A black matrix 1035 may also be provided. The transparent base material 1033 on which the colored layers and black matrix are provided is aligned and fixed to the substrate 1001. The colored layers and black matrix 1035 are covered with an overcoat layer 1036. Also, in FIG. 9A , there are light-emitting layers from which light does not pass through the colored layers and exits to the outside, and light-emitting layers from which light passes through the colored layers of each color and exits to the outside. Light that does not pass through the colored layers is white, and light that passes through the colored layers is red, green, and blue, so that an image can be expressed using four color pixels.

[0484] 9B shows an example in which colored layers (a red colored layer 1034R, a green colored layer 1034G, and a blue colored layer 1034B) are formed between the gate insulating film 1003 and the first interlayer insulating film 1020. In this manner, the colored layers may be provided between the substrate 1001 and the sealing substrate 1031.

[0485] Furthermore, the light-emitting device described above has a structure (bottom emission type) in which light is extracted from the substrate 1001 on which the FET is formed, but a structure (top emission type) in which light is extracted from the sealing substrate 1031 may also be used. A cross-sectional view of a top emission type light-emitting device is shown in FIG. 10 . In this case, a light-opaque substrate can be used as the substrate 1001. The process is the same as for a bottom emission type light-emitting device until a connection electrode connecting the FET and the anode of the light-emitting device is formed. Thereafter, a third interlayer insulating film 1037 is formed to cover the electrode 1022. This insulating film may also serve as a planarizing film. The third interlayer insulating film 1037 can be formed using the same material as the second interlayer insulating film, as well as other known materials.

[0486] Although the electrodes 1024W, 1024R, 1024G, and 1024B of the light-emitting device are herein defined as anodes, they may be cathodes. In addition, in the case of a top-emission light-emitting device as shown in FIG. 10 , the electrodes 1024W, 1024R, 1024G, and 1024B are preferably reflective electrodes. The EL layer 1028 has a structure similar to that described as the unit 103X in any one of Embodiments 2 to 6, and has an element structure that can emit white light.

[0487] In the top-emission structure shown in FIG. 10 , sealing can be performed using a sealing substrate 1031 provided with colored layers (a red colored layer 1034R, a green colored layer 1034G, and a blue colored layer 1034B). A black matrix 1035 may be provided on the sealing substrate 1031 so as to be positioned between pixels. The colored layers (the red colored layer 1034R, the green colored layer 1034G, and the blue colored layer 1034B) or the black matrix 1035 may be covered with an overcoat layer. Note that a light-transmitting substrate is used as the sealing substrate 1031. While an example of full-color display using four colors, red, green, blue, and white, is shown here, this is not particularly limited, and full-color display using four colors, red, yellow, green, and blue, or three colors, red, green, and blue, may also be performed.

[0488] A top-emission light-emitting device can be suitably configured with a microcavity structure. A light-emitting device having a microcavity structure can be obtained by using a reflective electrode as the first electrode and a semi-transmissive / semi-reflective electrode as the second electrode. At least an EL layer is provided between the reflective electrode and the semi-transmissive / semi-reflective electrode, and at least a light-emitting layer that serves as a light-emitting region is provided.

[0489] The reflectance of the reflective electrode to visible light is 40% to 100%, preferably 70% to 100%, and the resistivity is 1×10 −２ The semi-transmitting and semi-reflective electrode has a visible light reflectance of 20% to 80%, preferably 40% to 70%, and a resistivity of 1×10 −２ It is assumed that the film has a resistivity of Ω·cm or less.

[0490] 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, causing resonance.

[0491] In the light-emitting device, the optical distance between the reflective electrode and the semi-transmitting / semi-reflective electrode can be changed by changing the thickness of the transparent conductive film or the above-mentioned composite material, carrier transport material, etc. This makes it possible to intensify light of a resonant wavelength and attenuate light of a non-resonant wavelength between the reflective electrode and the semi-transmitting / semi-reflective electrode.

[0492] Note that, since the light reflected by the reflective electrode and returned (first reflected light) significantly interferes with the light (first incident light) that directly enters the semi-transmissive / 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 (2n-1)λ / 4 (where n is a natural number of 1 or more, and λ is the wavelength of the light emission to be amplified). By adjusting the optical distance, the phases of the first reflected light and the first incident light can be matched, thereby further amplifying the light emission from the light-emitting layer.

[0493] In the above configuration, the EL layer may have a structure having multiple light-emitting layers or a structure having a single light-emitting layer. For example, it may be combined with the above-mentioned tandem light-emitting device configuration, in which multiple EL layers are provided in one light-emitting device with a charge-generating layer sandwiched therebetween, and one or more light-emitting layers are formed in each EL layer.

[0494] The microcavity structure makes it possible to increase the light emission intensity of a specific wavelength in the front direction, thereby reducing power consumption. In the case of a light-emitting device that displays images using four sub-pixels of red, yellow, green, and blue, not only can the yellow light be used to improve brightness, but the microcavity structure that matches the wavelength of each color can be applied to all sub-pixels, resulting in a light-emitting device with good characteristics.

[0495] The light-emitting device in this embodiment can have favorable characteristics because it uses the light-emitting device described in any one of Embodiments 2 to 6. Specifically, the light-emitting device described in any one of Embodiments 2 to 6 has favorable emission efficiency, and therefore can have low power consumption.

[0496] Up to this point, active matrix light-emitting devices have been described. From now on, passive matrix light-emitting devices will be described. FIG. 11 shows a passive matrix light-emitting device manufactured by applying the present invention. FIG. 11A is a perspective view showing the light-emitting device, and FIG. 11B is a cross-sectional view taken along X-Y in FIG. 11A. In FIG. 11, an EL layer 955 is provided between an electrode 952 and an electrode 956 on a substrate 951. An end of the electrode 952 is covered with an insulating layer 953. A partition layer 954 is provided on the insulating layer 953. The sidewalls of the partition layer 954 are inclined so that the distance between one sidewall and the other sidewall becomes narrower as the sidewall approaches the substrate surface. That is, the cross section of the partition layer 954 in the short side direction is trapezoidal, and the bottom side (the side facing the same direction as the surface of the insulating layer 953 and in contact with the insulating layer 953) is shorter than the top side (the side facing the same direction as the surface of the insulating layer 953 and not in contact with the insulating layer 953). By providing the partition layer 954 in this manner, defects in the light-emitting device due to static electricity or the like can be prevented. Furthermore, a passive matrix light-emitting device using the light-emitting device described in any one of Embodiments 2 to 6 can be a highly reliable light-emitting device or a light-emitting device with low power consumption.

[0497] The light emitting device described above is capable of individually controlling a large number of minute light emitting devices arranged in a matrix, and is therefore suitable for use as a display device for displaying images.

[0498] This embodiment mode can be freely combined with other embodiment modes.

[0499] In this embodiment, an example in which the light-emitting device described in any one of Embodiments 2 to 6 is used as a lighting device will be described with reference to Fig. 12. Fig. 12B is a top view of the lighting device, and Fig. 12A is a cross-sectional view taken along the line e-f in Fig. 12B.

[0500] In the lighting device in this embodiment, a first electrode 401 is formed over a light-transmitting substrate 400 which serves as a support. The first electrode 401 corresponds to the electrode 551X in any one of Embodiments 2 to 6. When light is extracted from the first electrode 401 side, the first electrode 401 is formed using a light-transmitting material.

[0501] A pad 412 for supplying a voltage to the second electrode 404 is formed on the substrate 400 .

[0502] An EL layer 403 is formed over the first electrode 401. The EL layer 403 corresponds to a combination of the layer 104, the unit 103X, and the layer 105, or a combination of the layer 104, the unit 103X, the layer 106, the unit 103X2, and the layer 105 in any one of Embodiments 2 to 6. For details of these structures, see the descriptions thereof.

[0503] A second electrode 404 is formed to cover the EL layer 403. The second electrode 404 corresponds to the electrode 552X in any one of Embodiments 2 to 6. When light is extracted from the first electrode 401 side, the second electrode 404 is formed using a material with high reflectivity. The second electrode 404 is connected to a pad 412 to supply a voltage.

[0504] As described above, the lighting device described in this embodiment has a light-emitting device including the first electrode 401, the EL layer 403, and the second electrode 404. Since the light-emitting device has high emission efficiency, the lighting device in this embodiment can have low power consumption.

[0505] The lighting device is completed by bonding and sealing the substrate 400 on which the light-emitting device having the above structure is formed and the sealing substrate 407 using a sealant 405 and a sealant 406. Either the sealant 405 or the sealant 406 may be used alone. A desiccant may also be mixed into the inner sealant 406 (not shown in FIG. 12B ), which can absorb moisture and improve reliability.

[0506] Furthermore, the pad 412 and a part of the first electrode 401 can be provided as an external input terminal by extending them outside the sealing materials 405 and 406. An IC chip 420 or the like on which a converter or the like is mounted may also be provided thereon.

[0507] As described above, the lighting device described in this embodiment uses the light-emitting device described in any one of Embodiments 2 to 6 as an EL element, and can be a lighting device with low power consumption.

[0508] Embodiment 12 In this embodiment, an example of an electronic device including the light-emitting device described in any one of Embodiments 2 to 6 will be described. The light-emitting device described in any one of Embodiments 2 to 6 has high light-emitting efficiency and low power consumption. As a result, the electronic device described in this embodiment can be an electronic device having a light-emitting portion with low power consumption.

[0509] Examples of electronic devices to which the light-emitting devices are applied include television sets (also called televisions or television receivers), computer monitors, digital cameras, digital video cameras, digital photo frames, mobile phones (also called mobile phones or mobile phone devices), portable game machines, personal digital assistants, sound reproducing devices, large game machines such as pachinko machines, etc. Specific examples of these electronic devices are shown below.

[0510] 13A illustrates an example of a television set. The television set has a display portion 7103 incorporated in a housing 7101. Here, the housing 7101 is supported by a stand 7105. Images can be displayed on the display portion 7103, and the display portion 7103 includes light-emitting devices described in any one of Embodiments 2 to 6 arranged in a matrix.

[0511] The television set can be operated using operation switches on the housing 7101 or a separate remote control 7110. Channels or volume can be controlled using operation keys 7109 on the remote control 7110, and images displayed on the display portion 7103 can be controlled. A display portion 7107 may be provided on the remote control 7110 to display information to be output.

[0512] The television device is configured to include a receiver, a modem, etc. The receiver can receive general television broadcasts, and by connecting to a wired or wireless communication network via the modem, it is also possible to perform one-way (from sender to receiver) or two-way (between sender and receiver, or between receivers, etc.) information communication.

[0513] FIG. 13B shows a computer including 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 using the light-emitting devices described in any one of Embodiments 2 to 6 arranged in a matrix for the display portion 7203. The computer in FIG. 13B may have a configuration as shown in FIG. 13C. The computer in FIG. 13C 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 input can be performed by operating an input display displayed on the second display portion 7210 with a finger or a dedicated pen. The second display portion 7210 can display not only an input display but also other images. The display portion 7203 may also be a touch panel. The two screens are connected by a hinge, which can prevent the screens from being scratched or broken during storage or transportation.

[0514] 13D illustrates an example of a mobile terminal. The mobile terminal includes a display portion 7402 incorporated in a housing 7401, operation buttons 7403, an external connection port 7404, a speaker 7405, a microphone 7406, and the like. Note that the mobile terminal includes the display portion 7402 in which the light-emitting devices described in any one of Embodiments 2 to 6 are arranged in a matrix.

[0515] 13D can be configured so that 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 or creating an email can be performed by touching the display portion 7402 with a finger or the like.

[0516] The screen of the display portion 7402 has three main modes. The first is a display mode mainly for displaying images, the second is an input mode mainly for inputting information such as characters, and the third is a display+input mode that combines the display mode and the input mode.

[0517] For example, when making a call or creating an email, the display portion 7402 may be set to a character input mode mainly for inputting characters, and characters displayed on the screen may be input. In this case, it is preferable to display a keyboard or number buttons on most of the screen of the display portion 7402.

[0518] In addition, by providing a detection device having a sensor that detects tilt, such as a gyro sensor or an acceleration sensor, inside the mobile terminal, the orientation of the mobile terminal (portrait or landscape) can be determined and the screen display of the display portion 7402 can be automatically switched.

[0519] The screen mode can be switched by touching the display portion 7402 or by operating the operation buttons 7403 on the housing 7401. The screen mode can also be switched depending on the type of image displayed on the display portion 7402. For example, if the image signal to be displayed on the display portion is moving image data, the display mode is selected, and if it is text data, the input mode is selected.

[0520] In addition, in the input mode, a signal detected by an optical sensor in the display portion 7402 may be detected, and if there is no input by touch operation on the display portion 7402 for a certain period of time, the screen mode may be controlled to switch from the input mode to the display mode.

[0521] The display portion 7402 can also function as an image sensor. For example, personal authentication can be performed by touching the display portion 7402 with a palm or a finger to capture an image of a palm print, a fingerprint, or the like. Furthermore, by using a backlight that emits near-infrared light or a sensing light source that emits near-infrared light for the display portion, finger veins, palm veins, or the like can also be captured.

[0522] FIG. 14A is a schematic diagram showing an example of a cleaning robot.

[0523] The cleaning robot 5100 has a display 5101 arranged on its top surface, multiple cameras 5102 arranged on its side, a brush 5103, and an operation button 5104. Although not shown, the cleaning robot 5100 is also provided with tires, a suction port, and the like on its bottom surface. The cleaning robot 5100 is also provided with various other sensors, such as an infrared sensor, an ultrasonic sensor, an acceleration sensor, a piezoelectric sensor, an optical sensor, and a gyro sensor. The cleaning robot 5100 is also provided with wireless communication means.

[0524] The cleaning robot 5100 can move by itself, detect dust 5120, and suck up the dust from a suction port provided on the bottom surface.

[0525] The cleaning robot 5100 can also analyze the image captured by the camera 5102 to determine whether there are any obstacles such as walls, furniture, or steps. If the image analysis detects an object that may become tangled in the brush 5103, such as a wire, the cleaning robot 5100 can stop the rotation of the brush 5103.

[0526] The display 5101 can display the remaining battery level, the amount of dust that has been sucked up, etc. The path traveled by the cleaning robot 5100 may be displayed on the display 5101. The display 5101 may also be a touch panel, and an operation button 5104 may be provided on the display 5101.

[0527] The cleaning robot 5100 can communicate with a portable electronic device 5140 such as a smartphone. Images captured by the camera 5102 can be displayed on the portable electronic device 5140. This allows the owner of the cleaning robot 5100 to know the state of the room even when they are away from home. In addition, the display on the display 5101 can be confirmed on the portable electronic device 5140 such as a smartphone.

[0528] The light-emitting device of one embodiment of the present invention can be used for the display 5101 .

[0529] The robot 2100 shown in FIG. 14B includes a computing device 2110, a microphone 2102, an upper camera 2103, a speaker 2104, a display 2105, a lower camera 2106, an obstacle sensor 2107, and a movement mechanism 2108.

[0530] The microphone 2102 has a function of detecting the user's voice, environmental sounds, etc. The speaker 2104 has a function of emitting sound. The robot 2100 can communicate with the user using the microphone 2102 and the speaker 2104.

[0531] The display 2105 has a function of displaying various information. The robot 2100 can display information desired by the user on the display 2105. The display 2105 may be equipped with a touch panel. The display 2105 may also be a detachable information terminal, which can be installed in a fixed position on the robot 2100 to enable charging and data transfer.

[0532] The upper camera 2103 and the lower camera 2106 have a function of capturing images of the surroundings of the robot 2100. In addition, the obstacle sensor 2107 can detect the presence or absence of an obstacle in the moving direction when the robot 2100 moves forward using the moving mechanism 2108. The robot 2100 can recognize the surrounding environment and move safely using the upper camera 2103, the lower camera 2106, and the obstacle sensor 2107. The light-emitting device of one embodiment of the present invention can be used for the display 2105.

[0533] 14C is a diagram showing an example of a goggle-type display. The goggle-type display includes, for example, a housing 5000, a display unit 5001, a speaker 5003, an LED lamp 5004, operation keys (including a power switch or an operation switch), a connection terminal 5006, a sensor 5007 (having a function of measuring force, displacement, position, velocity, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared light), a microphone 5008, a display unit 5002, a support unit 5012, and earphones 5013.

[0534] The light-emitting device of one embodiment of the present invention can be used for the display portion 5001 and the display portion 5002 .

[0535] 15 shows an example in which the light-emitting device described in any one of Embodiments 2 to 6 is used in a desk lamp, which is a lighting device. The desk lamp shown in Fig. 15 includes a housing 2001 and a light source 2002, and the lighting device described in Embodiment 11 may be used as the light source 2002.

[0536] 16 shows an example in which the light-emitting device described in any one of Embodiments 2 to 6 is used as an indoor lighting device 3001. Since the light-emitting device described in any one of Embodiments 2 to 6 has high emission efficiency, the lighting device can have low power consumption. Furthermore, since the light-emitting device described in any one of Embodiments 2 to 6 can be made large, it can be used as a large-area lighting device. Furthermore, since the light-emitting device described in any one of Embodiments 2 to 6 is thin, it can be used as a thin lighting device.

[0537] The light-emitting device described in any one of Embodiments 2 to 6 can also be mounted on a windshield or a dashboard of an automobile. Figure 17 shows one mode in which the light-emitting device described in any one of Embodiments 2 to 6 is used on a windshield or a dashboard of an automobile. Display regions 5200 to 5203 are display regions provided using the light-emitting device described in any one of Embodiments 2 to 6.

[0538] The display region 5200 and the display region 5201 are display devices provided on the windshield of an automobile, and are equipped with the light-emitting device described in any one of Embodiments 2 to 6. The light-emitting device described in any one of Embodiments 2 to 6 can be a so-called see-through display device, in which the opposite side can be seen through, by forming the first electrode and the second electrode using light-transmitting electrodes. A see-through display can be installed on the windshield of an automobile without obstructing the view. When 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.

[0539] The display area 5202 is a display device provided in a pillar portion and equipped with the light-emitting device described in any one of Embodiments 2 to 6. The display area 5202 can complement the view blocked by the pillar by displaying an image from an imaging means provided on the vehicle body. Similarly, the display area 5203 provided on the dashboard can complement the view blocked by the vehicle body by displaying an image from an imaging means provided on the outside of the vehicle, thereby compensating for blind spots and improving safety. Displaying an image to complement the invisible part allows a driver to check for safety more naturally and without discomfort.

[0540] The display area 5203 can provide various information by displaying navigation information, speed or revolutions, mileage, remaining fuel, gear status, air conditioning settings, etc. The display items or layout can be changed as appropriate to suit the user's preferences. Note that this information can also be provided in the display areas 5200 to 5202. The display areas 5200 to 5203 can also be used as lighting devices.

[0541] 18A to 18C show a foldable portable information terminal 9310. Fig. 18A shows the portable information terminal 9310 in an unfolded state. Fig. 18B shows the portable information terminal 9310 in a state in the process of changing from one of the unfolded state and the folded state to the other. Fig. 18C shows the portable information terminal 9310 in a folded state. The portable information terminal 9310 has excellent portability in a folded state, and has excellent display visibility due to a seamless, wide display area in an unfolded state.

[0542] The display panel 9311 is supported by three housings 9315 connected by hinges 9313. Note that the display panel 9311 may be a touch panel (input / output device) equipped with a touch sensor (input device). Furthermore, the display panel 9311 can be reversibly transformed from an unfolded state to a folded state by bending the two housings 9315 via the hinges 9313. The light-emitting device of one embodiment of the present invention can be used for the display panel 9311.

[0543] Note that the structure described in this embodiment mode can be used by appropriately combining any of the structures described in Embodiment Modes 2 to 6.

[0544] As described above, the light-emitting device having the light-emitting device described in any one of Embodiments 2 to 6 has a very wide range of application, and the light-emitting device can be applied to electronic devices in a variety of fields. By using the light-emitting device described in any one of Embodiments 2 to 6, electronic devices with low power consumption can be obtained.

[0545] Note that this embodiment mode can be appropriately combined with other embodiment modes described in this specification.

[0546] In this example, physical properties and synthesis examples of organic compounds of one embodiment of the present invention will be described with reference to FIGS.

[0547] FIG. 19 shows Ir(mppy-3CP) ３ of １ FIG. 1 is a diagram illustrating the results of measuring a H NMR spectrum.

[0548] FIG. 20 shows Ir(mppy-3CP) ３ 1 is a diagram illustrating the results of measuring the absorption spectrum and the emission spectrum of a dichloromethane solution containing

[0549] FIG. 21 shows Ir(mppy-dmCP) ３ of １ FIG. 1 is a diagram illustrating the results of measuring a H NMR spectrum.

[0550] FIG. 22 shows Ir(mppy-dmCP) ３ 1 is a diagram illustrating the results of measuring the absorption spectrum and the emission spectrum of a dichloromethane solution containing

[0551] FIG. 23 shows Ir(mppy-m5CP) ３ of １ FIG. 1 is a diagram illustrating the results of measuring a H NMR spectrum.

[0552] FIG. 24 shows Ir(mppy-m5CP) ３ 1 is a diagram illustrating the results of measuring the absorption spectrum and the emission spectrum of a dichloromethane solution containing

[0553] FIG. 25 shows Ir(ppy-m5CP) ３ of １ FIG. 1 is a diagram illustrating the results of measuring a H NMR spectrum.

[0554] FIG. 26 shows Ir(ppy-m5CP) ３ 1 is a diagram illustrating the results of measuring the absorption spectrum and the emission spectrum of a dichloromethane solution containing

[0555] Synthesis Example 1 In Synthesis Example 1, tris[2-(4-methyl-5-(3-cyanophenyl)-2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(mppy-3CP)) represented by structural formula (136) in Embodiment 1 was synthesized. ３ An example of a method for synthesizing the compound (II) will be described.

[0556]

[0557] Step 1: Synthesis of 4-methyl-2-phenyl-5-(3-cyanophenyl)pyridine (abbreviation: Hmppy-3CP) 2.36 g of 5-bromo-4-methyl-2-phenylpyridine, 1.77 g of 3-cyanophenylboronic acid, 2.54 g of tripotassium phosphate, 35 mL of toluene, and 3.5 mL of water were placed in a three-necked flask equipped with a reflux condenser, and the inside of the flask was replaced with nitrogen. The contents of the flask were degassed by stirring under reduced pressure, and then tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd ２ (dba) ３ 0.089 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (abbreviation: S-Phos) and 0.16 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (abbreviation: S-Phos) were added. The mixture was reacted at 110°C for 7.5 hours with stirring. The synthesis scheme (1a) of Step 1 is shown below.

[0558] After a predetermined time had elapsed, the solvent was distilled off, water was added, and the target product was extracted with toluene. The toluene was distilled off from the extract, and the residue was separated by silica gel column chromatography using a mixed solvent of hexane and ethyl acetate (hexane:ethyl acetate=5:1) as the mobile phase. The mobile phase was then distilled off to obtain 2.43 g (yield 92%) of a white solid pyridine derivative.

[0559]

[0560] Step 2: Tris[2-(4-methyl-5-(3-cyanophenyl)-2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(mppy-3CP) ３2.42 g of 4-methyl-2-phenyl-5-(3-cyanophenyl)pyridine (abbreviation: Hmppy-3CP) obtained in Step 1 above and tris(2,4-pentanedionato)iridium(III) (abbreviation: Ir(acac) ３ 0.88 g of 2-(2-methyl-2-propanol) was placed in a reaction vessel equipped with a three-way stopcock, and the atmosphere in the reaction vessel was replaced with argon. The reaction was carried out at 250°C for 71 hours with stirring. The synthesis scheme (1b) of Step 2 is shown below.

[0561] After a predetermined time had elapsed, the resulting solid was separated using silica gel column chromatography using dichloromethane as the mobile phase. Furthermore, 0.22 g of a yellow solid was obtained (yield 12%) by recrystallization from the solid obtained by distilling off the mobile phase and a mixed solution of dichloromethane and methanol. This yellow solid (0.22 g) was purified by train sublimation to obtain 0.15 g of the target product in the form of a yellow solid (yield 68%). The sublimation purification conditions were a pressure of 2.7 Pa, an argon gas flow rate of 10.5 mL / min, and a heating temperature of 370°C.

[0562]

[0563] Nuclear magnetic resonance spectroscopy ( １ As a result of measurement using H-NMR, it was found that the yellow solid obtained in step 2 above was Ir(mppy-3CP). ３ ) was confirmed. １ The H-NMR chart is shown in FIG. 19, and the analysis results are shown below.

[0564] １ H-NMR. δ(CD ２ Cl ２ ): 2.34 (s, 9H), 6.79 (d, 3H), 6.84 (t, 3H), 6.92 (t, 3H), 7.29 (s, 3H), 7.32 (d, 3H), 7.41 (s, 3H), 7.52 (t, 3H), 7.64 (d, 3H), 7.71 (d, 3H), 7.83 (s, 3H).

[0565] Ir(mppy-3CP) ３The results of measuring the ultraviolet-visible absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and emission spectrum of a dichloromethane solution containing Ir(mppy-3CP) are shown in Figure 20. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity or emission intensity. ３ had an emission peak at 540 nm, and green emission was observed from dichloromethane. The absorption spectrum shown in Figure 20 was obtained by subtracting the absorption spectrum measured by placing only dichloromethane in a quartz cell from the absorption spectrum measured by placing a dichloromethane solution (0.010 mmol / L) in a quartz cell.

[0566] The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation) at room temperature after placing a dichloromethane solution (0.010 mmol / L) in a quartz cell.

[0567] The emission spectrum was measured using a fluorometer (FS920 manufactured by Hamamatsu Photonics K.K.) in a glove box (LABstar M13 (1250 / 780) manufactured by Bright Corporation) at room temperature under a nitrogen atmosphere, with a deoxygenated dichloromethane solution (0.010 mmol / L) placed in a quartz cell, which was then sealed.

[0568] Ir(mppy-3CP) ３ is R of the pyridine ring １０７ The methyl group restricts the free rotation of the phenyl group to which the cyano group is introduced. ３ exhibits excellent thermal properties. It also narrows the width of the emission spectrum and improves the color purity of the emitted color. It can also be suitably used as a green light-emitting material.

[0569] Synthesis Example 2 In Synthesis Example 2, tris[2-(4-methyl-5-(4-cyano-2,6-dimethylphenyl)-2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(mppy-dmCP)) represented by structural formula (104) in Embodiment 1 was synthesized. ３ An example of a method for synthesizing the compound (II) will be described.

[0570]

[0571] Step 1: Synthesis of 5-bromo-4-methyl-2-phenylpyridine 15.87 g of 2,5-dibromo-4-methylpyridine, 9.27 g of phenylboronic acid, 23.51 g of potassium carbonate, 530 mL of acetonitrile, and 265 mL of methanol were placed in a three-necked flask equipped with a reflux condenser, and the inside of the flask was purged with nitrogen. After degassing by stirring under reduced pressure, dipalladium(II) acetate (abbreviated as Pd(OAc)) was added. ２ ) 0.56 g, and triphenylphosphine (abbreviation: PPh ３ The mixture was stirred at 50° C. for 19.5 hours to react. The synthesis scheme (2a) of Step 1 is shown below.

[0572] After a predetermined time had elapsed, the solvent was distilled off, water was added, and the target product was extracted with dichloromethane. The residue obtained by distilling off dichloromethane from the extract was separated by silica gel column chromatography using a mixed solvent of hexane and ethyl acetate (hexane:ethyl acetate=10:1) as the mobile phase to obtain 13.40 g (yield 85%) of a colorless oily pyridine derivative.

[0573]

[0574] Step 2: Synthesis of 4-methyl-2-phenyl-5-(4-cyano-2,6-dimethylphenyl)pyridine (abbreviation: Hmppy-dmCP) 3.25 g of 5-bromo-4-methyl-2-phenylpyridine obtained in Step 1 above, 4.09 g of 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile, 10.96 g of tripotassium phosphate, 4.13 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (abbreviation: S-Phos), and 160 mL of toluene were placed in a three-neck flask equipped with a reflux condenser, and the inside of the flask was replaced with nitrogen. The contents of the flask were degassed by stirring under reduced pressure, and then tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd ２ (dba) ３ 2.25 g of HCl was added to the reaction mixture, and the mixture was stirred at 130° C. for 15 hours. The synthesis scheme (2b) of Step 2 is shown below.

[0575] After a predetermined time had elapsed, the resulting mixture was subjected to suction filtration, and the dichloromethane was distilled off from the filtrate to obtain a residue, which was then separated by silica gel column chromatography using a mixed solvent of hexane and ethyl acetate (hexane:ethyl acetate=10:1) as the mobile phase to obtain 2.18 g (yield 55%) of a yellowish-white solid pyridine derivative.

[0576]

[0577] Step 3: Di-μ-chloro-tetrakis[2-(4-methyl-5-(4-cyano-2,6-dimethylphenyl)-2-pyridinyl-κN)phenyl-κC]diiridium(III) (abbreviation: [Ir(mppy-dmCP) ２ Cl] ２ Synthesis of iridium chloride hydrate (IrCl) ３ ・H ２ 0.99 g of methyl methyl ketone (Furuya Metal Co., Ltd.) was placed in a recovery flask equipped with a reflux condenser, and the atmosphere in the flask was replaced with argon. The flask was then irradiated with 2.45 GHz microwaves at 100 W output for 2 hours to induce a reaction. The synthesis scheme (2c) of Step 3 is shown below.

[0578] After a predetermined time has elapsed, the resulting residue is suction filtered and washed with methanol to obtain a yellow solid binuclear complex di-μ-chloro-tetrakis[2-(4-methyl-5-(4-cyano-2,6-dimethylphenyl)-2-pyridinyl-κN)phenyl-κC]diiridium(III) (abbreviation: [Ir(mppy-dmCP) ２ Cl] ２ ) 1.82 g (yield 67%) was obtained.

[0579]

[0580] Step 4: Tris[2-(4-methyl-5-(4-cyano-2,6-dimethylphenyl)-2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(mppy-dmCP) ３Synthesis of di-μ-chloro-tetrakis[2-(4-methyl-5-(4-cyano-2,6-dimethylphenyl)-2-pyridinyl-κN)phenyl-κC]diiridium(III) (abbreviation: [Ir(mppy-dmCP) ２ Cl] ２ 1.82 g of 4-methyl-2-phenyl-5-(4-cyano-2,6-dimethylphenyl)pyridine (abbreviation: Hmppy-dmCP) obtained in Step 2, 1.70 g of 4-methyl-2-phenyl-5-(4-cyano-2,6-dimethylphenyl)pyridine (abbreviation: Hmppy-dmCP), 1.51 g of potassium carbonate, and 8 g of phenol were placed in a three-neck flask equipped with a reflux condenser, and the inside of the flask was replaced with nitrogen. The mixture was then reacted at 185°C for 24 hours with stirring. The synthesis scheme (2d) of Step 4 is shown below.

[0581] After a predetermined time had elapsed, the resulting mixture was suction filtered and washed with water and methanol. The resulting solid was separated using silica gel column chromatography using dichloromethane as the mobile phase. Furthermore, 0.16 g of a yellow solid was obtained (7% yield) using a recrystallization method from a mixed solution of the solid obtained by distilling off the mobile phase and dichloromethane and methanol. This 0.16 g of yellow solid was purified by train sublimation to obtain 0.10 g of the target product in the form of a yellow solid (63% yield). The sublimation purification conditions were a pressure of 2.6 Pa, an argon gas flow rate of 11 mL / min, and a heating temperature of 360°C.

[0582]

[0583] Nuclear magnetic resonance spectroscopy ( １ As a result of measurement using H-NMR, it was found that the yellow solid obtained in Step 4 above was Ir(mppy-dmCP). ３ It was confirmed that this was the case. １ The H-NMR chart is shown in FIG. 21, and the analysis results are shown below.

[0584] １ H-NMR. δ(CDCl ３ ): 1.38 (s, 9H), 1.65 (s, 9H), 1.96 (s, 9H), 6.88-6.96 (m, 9H), 7.30 (s, 3H), 7.32 (d, 6H), 7.63 (d, 3H), 7.75 (s, 3H).

[0585] Ir(mppy-dmCP) ３ The results of measuring the ultraviolet-visible absorption spectrum and emission spectrum of a dichloromethane solution containing Ir(mppy-dmCP) are shown in Figure 22. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity or emission intensity. ３ had an emission peak at 519 nm, and green emission was observed from dichloromethane. The absorption spectrum shown in Figure 22 is the result of subtracting the absorption spectrum measured by placing only dichloromethane in a quartz cell from the absorption spectrum measured by placing a dichloromethane solution (0.0105 mmol / L) in a quartz cell.

[0586] The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation) at room temperature after placing a dichloromethane solution (0.0105 mmol / L) in a quartz cell.

[0587] The emission spectrum was measured using an absolute PL quantum yield measurement apparatus (Model C11347-01, manufactured by Hamamatsu Photonics K.K.) in a glove box (LABstar M13 (1250 / 780), manufactured by Bright Co., Ltd.) under a nitrogen atmosphere. A deoxygenated dichloromethane solution (0.0105 mmol / L) was placed in a quartz cell, which was then sealed, and the measurement was carried out at room temperature.

[0588] Ir(mppy-dmCP) ３ represents a group represented by the general formula (G0) shown in Embodiment 1 in which a cyano group is R １０４ The two ortho positions (R １０２ and R １０６ ) has a methyl group. １０７ These three methyl groups strongly restrict the free rotation of the phenyl group. This results in Ir(mppy-dmCP) ３ exhibits excellent thermal properties. It also narrows the width of the emission spectrum and improves the color purity of the emitted color. It can also be suitably used as a green light-emitting material.

[0589] Synthesis Example 3 In Synthesis Example 3, an organometallic complex of the present invention represented by structural formula (137) in Embodiment 1, tris[2-(4-methyl-5-(5-cyano-2-methylphenyl)-2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(mppy-m5CP) ３ ) synthesis method will be explained.

[0590]

[0591] Step 1: Synthesis of 4-methyl-2-phenyl-5-(5-cyano-2-methylphenyl)pyridine (abbreviation: Hmppy-3CP) 2.31 g of 5-bromo-4-methyl-2-phenylpyridine, 2.23 g of 5-cyano-2-phenylboronic acid, 7.88 g of tripotassium phosphate, and 115 mL of toluene were placed in a three-necked flask equipped with a reflux condenser, and the inside of the flask was replaced with nitrogen. The contents of the flask were degassed by stirring under reduced pressure, and then tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd ２ (dba) ３ To the resulting mixture, 1.08 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (abbreviation: S-Phos) and 2.01 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (abbreviation: S-Phos) were added. The mixture was reacted at 130°C for 7.5 hours with stirring. The synthesis scheme (3a) of Step 1 is shown below.

[0592] After a predetermined time had elapsed, the solvent was distilled off, water was added, and the target product was extracted with toluene. The residue obtained by distilling off the toluene from the extract was separated by silica gel column chromatography using a mixed solvent of toluene and ethyl acetate (toluene:ethyl acetate=30:1) as the mobile phase to obtain 2.12 g (yield 80%) of a yellow oily pyridine derivative.

[0593]

[0594] Step 2: Tris[2-(4-methyl-5-(5-cyano-2-methylphenyl)-2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(mppy-m5CP) ３2.42 g of 4-methyl-2-phenyl-5-(5-cyano-2-methylphenyl)pyridine (abbreviation: Hmppy-m5CP) obtained in Step 1 above and tris(2,4-pentanedionato)iridium(III) (abbreviation: Ir(acac) ３ 0.88 g of 2-methyl-2-propanol (3-methyl-2-propanol) was placed in a reaction vessel equipped with a three-way stopcock, and the atmosphere in the reaction vessel was replaced with argon. The reaction was carried out at 250°C for 67.5 hours with stirring. The synthesis scheme (3b) of Step 2 is shown below.

[0595] After a predetermined time had elapsed, the obtained solid was separated using silica gel column chromatography using dichloromethane as the mobile phase. Furthermore, 0.24 g of a yellow solid was obtained (yield 19%) by recrystallization from the solid obtained by distilling off the mobile phase and a mixed solution of dichloromethane and methanol. This yellow solid (0.24 g) was purified by train sublimation to obtain 0.18 g of the target product in the form of a yellow solid (yield 75%). The sublimation purification conditions were a pressure of 2.6 Pa, an argon gas flow rate of 11 mL / min, and a heating temperature of 375°C.

[0596]

[0597] Nuclear magnetic resonance spectroscopy ( １ As a result of measurement using H-NMR, it was found that the yellow solid obtained in step 2 above was Ir(mppy-m5CP). ３ ) was confirmed. １ The H-NMR chart is shown in FIG. 23, and the analysis results are shown below.

[0598] １ H-NMR. δ(CD ２ Cl ２ ): 1.38 (s, 3H), 1.49 (d, 3H), 2.04 (s, 6H), 2.07 (s, 6H), 6.84-6.96 (m, 9H), 7.15-7 .36 (m, 8H), 7.44 (d, 1H), 7.54-7.58 (m, 3H), 7.65-7.73 (m, 3H), 7.78-7.86 (m, 3H).

[0599] Ir(mppy-m5CP) ３The results of measuring the ultraviolet-visible absorption spectrum and emission spectrum of a dichloromethane solution containing Ir(mppy-m5CP) are shown in Figure 24. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity or emission intensity. ３ had an emission peak at 523 nm, and green emission was observed from dichloromethane. The absorption spectrum shown in Figure 24 was obtained by subtracting the absorption spectrum measured by placing only dichloromethane in a quartz cell from the absorption spectrum measured by placing a dichloromethane solution (0.0109 mmol / L) in a quartz cell.

[0600] The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation) at room temperature after placing a dichloromethane solution (0.0109 mmol / L) in a quartz cell.

[0601] The emission spectrum was measured using a fluorometer (FS920 manufactured by Hamamatsu Photonics K.K.) in a glove box (LABstar M13 (1250 / 780) manufactured by Bright Corporation) at room temperature under a nitrogen atmosphere, with a deoxygenated dichloromethane solution (0.0109 mmol / L) placed in a quartz cell, which was then sealed.

[0602] Ir(mppy-m5CP) ３ represents a group represented by the general formula (G0) shown in Embodiment 1 in which a cyano group is R １０５ R at the ortho position of the phenyl group introduced into １０２ The R of the pyridine ring has a methyl group. １０７ These two methyl groups strongly restrict the free rotation of the phenyl group. This results in Ir(mppy-m5CP) ３ exhibits excellent thermal properties. It also narrows the width of the emission spectrum and improves the color purity of the emitted color. It can also be suitably used as a green light-emitting material.

[0603] Synthesis Example 4 In Synthesis Example 4, tris[2-(5-(5-cyano-2-methylphenyl)-2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(ppy-m5CP)) represented by structural formula (138) in Embodiment 1 was synthesized. ３ An example of a method for synthesizing the compound (II) will be described.

[0604]

[0605] Step 1: Synthesis of 5-(5-cyano-2-methylphenyl)-2-phenylpyridine (abbreviation: Hppy-m5CP) 9.82 g of 5-bromo-2-methylpyridine, 8.03 g of 5-cyano-2-methylphenylboronic acid, 10.62 g of tripotassium phosphate, 150 mL of toluene, and 15 mL of water were placed in a three-neck flask equipped with a reflux condenser, and the inside of the flask was replaced with nitrogen. The contents of the flask were degassed by stirring under reduced pressure, and then tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd ２ (dba) ３ 0.38 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (abbreviation: S-Phos) and 0.70 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (abbreviation: S-Phos) were added. The reaction was carried out at 110°C for 2 hours with stirring. The synthesis scheme (4a) of Step 1 is shown below.

[0606] After a predetermined time had elapsed, the solvent was distilled off, water was added, and the target product was extracted with toluene. The toluene was distilled off from the extract, and the residue was separated by silica gel column chromatography using a mixed solvent of hexane and ethyl acetate (hexane:ethyl acetate=10:1) as the mobile phase, to obtain 11.21 g (yield 98%) of a colorless oily pyridine derivative.

[0607]

[0608] Step 2: Tris[2-(5-(5-cyano-2-methylphenyl)-2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(ppy-m5CP) ３ Synthesis of 5-(5-cyano-2-methylphenyl)-2-phenylpyridine (abbreviation: Hppy-m5CP) obtained in Step 1 above and tris(2,4-pentanedionato)iridium(III) (abbreviation: Ir(acac) ３ 0.78 g of 4-methyl-2-propanol (4) and 0.78 g of 4-methyl-2-propanol (4) were placed in a reaction vessel equipped with a three-way stopcock, and the atmosphere in the reaction vessel was replaced with argon. The reaction was carried out at 250°C for 78 hours with stirring. The synthesis scheme (4b) of Step 2 is shown below.

[0609] After a predetermined time had elapsed, the resulting solid was separated using silica gel column chromatography with a mixed solvent of hexane and ethyl acetate (hexane:ethyl acetate = 2:1) as the mobile phase. The mobile phase was then distilled off to obtain a solid, which was then separated using silica gel column chromatography with dichloromethane as the mobile phase. Furthermore, the solid obtained by distilling off the mobile phase and a mixed solution of dichloromethane and methanol were recrystallized to obtain 0.30 g (yield 19%) of the target product as a yellow solid.

[0610]

[0611] Nuclear magnetic resonance spectroscopy ( １ H-NMR) revealed that the yellow solid obtained in step 2 was Ir(ppy-m5CP). ３ ) was confirmed. １ The H-NMR chart is shown in FIG. 25, and the analysis results are shown below.

[0612] １ H-NMR. δ(CDCl ３ ): 1.93 (s, 9H), 6.92 (d, 6H), 6.96-6.99 (m, 3H), 7.22 (d, 3H), 7.29 (d, 3H), 7.49-7.51 (m, 6H), 7.55 (dd, 3H), 7.72 (d, 3H), 7.98 (d, 3H).

[0613] Ir(ppy-m5CP) ３ The results of measuring the ultraviolet-visible absorption spectrum and emission spectrum of a dichloromethane solution containing Ir(ppy-m5CP) are shown in Figure 26. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity or emission intensity. ３ had an emission peak at 540 nm, and green emission was observed from dichloromethane. The absorption spectrum shown in Figure 26 was obtained by subtracting the absorption spectrum measured by placing only dichloromethane in a quartz cell from the absorption spectrum measured by placing a dichloromethane solution (0.0099 mmol / L) in a quartz cell.

[0614] The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation) at room temperature after placing a dichloromethane solution (0.0099 mmol / L) in a quartz cell.

[0615] The emission spectrum was measured using a fluorometer (FS920 manufactured by Hamamatsu Photonics K.K.) in a glove box (LABstar M13 (1250 / 780) manufactured by Bright Corporation) at room temperature under a nitrogen atmosphere, with a deoxygenated dichloromethane solution (0.0099 mmol / L) placed in a quartz cell, which was then sealed.

[0616] Ir(ppy-m5CP) ３ is a cyano group R １０５ and R at the ortho position of the other phenyl group. １０２ This methyl group strongly inhibits the free rotation of the phenyl group. ３ exhibits excellent thermal properties. It also narrows the width of the emission spectrum and improves the color purity of the emitted color. It can also be suitably used as a green light-emitting material.

[0617] In this example, a light-emitting device 1 according to one embodiment of the present invention will be described with reference to FIGS.

[0618] FIG. 27 is a diagram illustrating the configuration of the light-emitting device 550X.

[0619] FIG. 28 is a diagram illustrating the current density-luminance characteristics of light-emitting device 1 and light-emitting device 2.

[0620] FIG. 29 is a diagram illustrating the luminance-current efficiency characteristics of the light-emitting device 1 and the light-emitting device 2. In FIG.

[0621] FIG. 30 is a diagram illustrating the voltage-luminance characteristics of the light-emitting device 1 and the light-emitting device 2. In FIG.

[0622] FIG. 31 is a diagram illustrating the voltage-current characteristics of the light-emitting device 1 and the light-emitting device 2. In FIG.

[0623] 32 is a diagram illustrating the luminance-external quantum efficiency characteristics of light-emitting device 1 and light-emitting device 2. The external quantum efficiency was calculated from the luminance, assuming that the light distribution characteristics of the light-emitting device are Lambertian type.

[0624] FIG. 33 shows the light emitting device 1 and the light emitting device 2 at 1000 cd / m ２10 is a diagram illustrating an emission spectrum when light is emitted at a luminance of 1000 .mu.m.

[0625] FIG. 34 shows the results of the experiment using a constant current density (50 mA / cm ２ 10 is a diagram illustrating the change over time in normalized luminance of the light-emitting device 1 when the light-emitting device 1 is caused to emit light at a temperature of 1000 K.

[0626] <Light-Emitting Device 1> The light-emitting device 1 fabricated and described in this example has the same configuration as the light-emitting device 550X (see FIG. 27).

[0627] <Configuration of Light-Emitting Device 1> The configuration of light-emitting device 1 is shown in Table 1. The structural formulas of the materials used in the light-emitting device described in this example are shown below. Note that in the tables of this example, subscripts and superscripts are written in standard size for convenience. For example, subscripts used for abbreviations and superscripts used for units are written in standard size in the tables. These descriptions in the tables can be interpreted in accordance with the descriptions in the specification.

[0628]

[0629]

[0630]

[0631] <<Method of Fabricating Light-Emitting Device 1>> The light-emitting device 1 described in this example was fabricated using a method including the following steps.

[0632] [First Step] In the first step, the electrode 551X was formed. Specifically, the electrode 551X was formed by a sputtering method using indium oxide-tin oxide (abbreviation: ITSO) containing silicon or silicon oxide as a target. The electrode 551X contained ITSO and had a thickness of 70 nm and a thickness of 4 mm. ２ It has an area of ​​(2 mm x 2 mm).

[0633] Next, the workpiece on which the electrodes were formed was washed with water, baked at 200°C for 1 hour, and then subjected to UV ozone treatment for 370 seconds. −４The mixture was introduced into a vacuum deposition apparatus whose internal pressure had been reduced to about Pa, and then vacuum-baked at 170° C. for 30 minutes in a heating chamber of the vacuum deposition apparatus. Thereafter, the mixture was allowed to cool for about 30 minutes.

[0634] [Second Step] In the second step, a layer 104X was formed over the electrode 551X. Specifically, materials were co-evaporated using a resistance heating method. The layer 104X contained 4,4′,4″-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II) and molybdenum oxide (abbreviation: MoOx) in a weight ratio of DBT3P-II:MoOx=2:1, and had a thickness of 40 nm.

[0635] [Third Step] In the third step, a layer 112X was formed on the layer 104X. Specifically, a material was evaporated by resistive heating. The layer 112X contained 4,4′-diphenyl-4″-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBiBP) and had a thickness of 20 nm.

[0636] [Fourth Step] In the fourth step, a layer 111X was formed on the layer 112X. Specifically, materials were co-evaporated by resistance heating. The layer 111X was formed using 9-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9′-phenyl-2,3′-bi-9H-carbazole (abbreviation: mPCCzPTzn-02), 9,9′-diphenyl-9H,9′H-3,3′-bicarbazole (abbreviation: PCCP), and tris[2-(4-methyl-5-(3-cyanophenyl)-2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(mppy-3CP) ３ ) to mPCCzPTzn-02:PCCP:Ir(mppy-3CP) ３ = 0.6:0.4:0.1 (weight ratio) and had a thickness of 40 nm.

[0637] [Fifth Step] In the fifth step, a layer 113X1 was formed on the layer 111X. Specifically, a material was evaporated using a resistance heating method. The layer 113X1 contained mPCCzPTzn-02 and had a thickness of 20 nm.

[0638] In the sixth step, a layer 113X2 was formed on the layer 113X1. Specifically, a material was evaporated by resistive heating. The layer 113X2 contained 2,9-di(2-naphthyl)-4,7-diphenyl-1,10-phenanthroline (NBphen) and had a thickness of 10 nm.

[0639] [Seventh Step] In the seventh step, a layer 105X was formed on the layer 113X2. Specifically, a material was evaporated using a resistance heating method. The layer 105X contained lithium fluoride (LiF) and had a thickness of 1 nm.

[0640] [Eighth Step] In the eighth step, an electrode 552X was formed on the layer 105X. Specifically, a material was evaporated using a resistance heating method. The electrode 552X contained aluminum (Al) and had a thickness of 200 nm.

[0641] <<Operating Characteristics of Light-Emitting Device 1>> When power was supplied, the light-emitting device 1 emitted light EL1 (see FIG. 27). The operating characteristics of the light-emitting device 1 were measured at room temperature (23°C) (see FIGS. 28 to 33). The luminance and CIE chromaticity were measured using a color luminance meter (BM-5A, manufactured by Topcon Corporation), and the emission spectrum was measured using a multichannel spectrometer (PMA-11, manufactured by Hamamatsu Photonics K.K.).

[0642] The fabricated light-emitting device had a brightness of 1000 cd / m ２ The main initial characteristics when the light-emitting device was irradiated at a constant current density (50 mA / cm) in an environment of 85°C are shown in Table 2. ２ ) and measured the time LT50 until the luminance decreased to 50% of the initial luminance. The LT50 values ​​are shown in Table 3. Table 2 also shows the properties of other light-emitting devices whose configurations will be described later.

[0643]

[0644]

[0645] It was found that the light-emitting device 1 exhibited good characteristics. For example, the light-emitting device 1 was able to extend the elapsed time LT50 until the luminance decreased to 50% of the initial luminance in a severe high-temperature environment of 85°C. Furthermore, compared with the comparative device 1, the configuration of which will be described in Reference Example 1 below, it achieved a longer operating life. Furthermore, the introduction of a cyano group improved heat resistance without impairing the characteristics of good operating voltage and good external quantum efficiency.

[0646] <Light-emitting device 2> The light-emitting device 2 fabricated in this example has the same configuration as the light-emitting device 550X (see FIG. 27). The configuration of the light-emitting device 2 differs from that of the light-emitting device 1 in the layer 111X. Specifically, the layer 111X is made of Ir(mppy-3CP). ３ Instead of tris[2-(4-methyl-5-(5-cyano-2-methylphenyl)-2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(mppy-m5CP) ３ ) is included in the light-emitting device 1.

[0647] <<Method of Fabricating Light-Emitting Device 2>> The light-emitting device 2 described in this example was fabricated using a method having the following steps.

[0648] In the fourth step of the method for producing the light-emitting device 2, Ir(mppy-3CP) ３ Instead, Ir(mppy-m5CP) ３ The method for fabricating the light-emitting device 1 differs from that for fabricating the light-emitting device 1 in that the method for fabricating the light-emitting device 1 is used. Here, the differences will be described in detail, and the above description will be used for the parts in which the same method is used.

[0649] [Fourth Step] In the fourth step, a layer 111X was formed on the layer 112X. Specifically, materials were co-evaporated using a resistance heating method. The layer 111X was formed by co-evaporating mPCCzPTzn-02, PCCP, and Ir(mppy-m5CP). ３ mPCCzPTzn-02:PCCP:Ir(mppy-m5CP) ３ = 0.6:0.4:0.1 (weight ratio) and had a thickness of 40 nm.

[0650] <<Operating Characteristics of Light-Emitting Device 2>> When power was supplied, light-emitting device 1 and light-emitting device 2 emitted light EL1 (see FIG. 27). The operating characteristics of light-emitting device 2 were measured at room temperature (see FIGS. 28 to 33).

[0651] The fabricated light-emitting device had a brightness of 1000 cd / m ２ Table 2 shows the main initial characteristics when light was emitted at about 1000 kJ / s.

[0652] It was found that the light-emitting device 2 exhibited good characteristics. For example, the light-emitting device 2 emitted green light with high color purity. The color purity was also suitable for use in a full-color display.

[0653] Reference Example 1 The comparative device 1 fabricated in this reference example has the same configuration as the light-emitting device 550X (see FIG. 27).

[0654] The structure of the comparative device 1 differs from that of the light-emitting device 1 in the layer 111X. Specifically, the layer 111X is made of Ir(mppy-3CP). ３ [2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(ppy) ２ The light-emitting device 1 differs from the light-emitting device 1 in that it includes a .lambda.

[0655] <<Method for Fabricating Comparative Device 1>> Comparative device 1 described in this example was fabricated using a method including the following steps.

[0656] In the fourth step of the method for producing the comparative device 1, Ir(mppy-3CP) ３ Instead, Ir(ppy) ２ The method of fabricating the light-emitting device 1 differs from that of fabricating the light-emitting device 1 in that a compound (mdppy) was used. Here, the differences will be described in detail, and the above description will be used for the parts in which the same method was used.

[0657] [Fourth Step] In the fourth step, a layer 111X was formed on the layer 112X. Specifically, materials were co-evaporated using a resistance heating method. The layer 111X was formed by co-evaporating mPCCzPTzn-02, PCCP, and Ir(ppy). ２ (mdppy) to mPCCzPTzn-02:PCCP:Ir(ppy) ２ The weight ratio of mdppy to mdppy was 0.6:0.4:0.1, and the thickness of the film was 40 nm.

[0658] <<Operating Characteristics of Comparative Device 1>> When power was applied, comparative device 1 emitted light EL1 (see FIG. 27). The operating characteristics of comparative device 1 were measured at room temperature (see FIGS. 28 to 33).

[0659] The comparative device 1 thus fabricated was tested at a luminance of 1000 cd / m ２ Table 2 shows the main initial characteristics when the comparative device 1 was irradiated with a constant current density (50 mA / cm) in an environment of 85°C. ２ The LT50, the time it took for the luminance to decrease to 50% of the initial luminance, was measured. The LT50 values ​​are shown in Table 3.

[0660] ANO: conductive film, C21: capacitor, C22: capacitor, CFX: colored layer, CP: conductive material, GD: drive circuit, hv: light, M21: transistor, N21: node, N22: node, SD: drive circuit, SW21: switch, SW22: switch, SW23: switch, ELX: light, ELY: light, 103S: unit, 103X: unit, 103Y: unit, 104S: layer, 104X: layer, 104XY: region, 104Y: layer, 104: layer, 105S: layer, 105X: layer, 105Y: layer, 105: layer, 106_1: layer, 106_2: layer, 106_3: layer, 10 6: layer, 111X: layer, 111Y: layer, 112_2: layer, 112S: layer, 112X: layer, 112: layer, 113_2: layer, 113S: layer, 113X: layer, 113: layer, 114N: layer, 114P: layer, 114S: layer, 231: region, 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, 510: substrate, 519B: terminal, 520T: region, 520: functional layer, 521: insulating film, 528: insulating film, 529_1: film, 529_2: film, 529 _3: film, 530X: pixel circuit, 540: functional layer, 550S: photoelectric conversion device, 550X: light-emitting device, 550Y: light-emitting device, 551S: electrode, 551X: electrode, 551XS: gap, 551XY: gap, 551Y: electrode, 552S: electrode, 552X: electrode, 552Y: electrode, 591X: opening, 591Y: opening, 601: source line driving circuit, 602: pixel portion, 603: gate line driving circuit, 604: sealing substrate, 605: sealing material, 607: space, 608: routing wiring, 609: external input terminal, 610: element substrate, 611: switching FE T, 612: current control FET, 613: first electrode, 614: insulator, 616: EL layer, 617: second electrode, 618: light emitting device, 623: FET, 700: display device, 702X: pixel, 703: pixel, 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, 1024B: electrode,1024G: electrode, 1024R: electrode, 1024W: electrode, 1025: partition wall, 1028: EL layer, 1029: electrode, 1031: sealing substrate, 1032: sealing material, 1033: base material, 1034B: colored layer, 1034G: colored layer, 1034R: colored layer, 1035: black matrix, 1036: overcoat layer, 1037: third interlayer insulating film, 1040: pixel portion, 1041: driver circuit portion, 1042: peripheral portion, 2001: housing , 2002: Light source, 2100: Robot, 2102: Microphone, 2103: Upper camera, 2104: Speaker, 2105: Display, 2106: Lower camera, 2107: Obstacle sensor, 2108: Moving mechanism, 2110: Computing device, 3001: Lighting device, 5000: Housing, 5001: Display unit, 5002: Display unit, 5003: Speaker, 5004: LED lamp, 5006: Connection terminal, 5007: Sensor, 5008 : microphone, 5012: support part, 5013: earphone, 5100: cleaning robot, 5101: display, 5102: camera, 5103: brush, 5104: operation button, 5120: dust, 5140: portable electronic device, 5200: display area, 5201: display area, 5202: display area, 5203: display area, 7101: housing, 7103: display part, 7105: stand, 7107: display part, 7109: operation key, 71 10: remote control device, 7201: main body, 7202: housing, 7203: display unit, 7204: keyboard, 7205: external connection port, 7206: pointing device, 7210: second display unit, 7401: housing, 7402: display unit, 7403: operation button, 7404: external connection port, 7405: speaker, 7406: microphone, 9310: mobile information terminal, 9311: display panel, 9313: hinge, 9315: housing,

Claims

1. An organic compound represented by the general formula (G0). 【Chemistry 1】 (In the above general formula (G0), X is a nitrogen atom or a carbon atom, When X is a carbon atom, X is bonded to hydrogen or a substituent. R １０４ and R １０５ Either one of them is a cyano group, R １０２ and R １０７ At least one of them is an alkyl group having 1 to 6 carbon atoms. R １０１ ~R １１１ The others are each independently bonded to hydrogen or a substituent. Each of the substituents is independently a C1 to C6 alkyl group, a C3 to C7 cycloalkyl group, a substituted or unsubstituted C6 to C13 aryl group, a substituted or unsubstituted C1 to C5 heteroaryl group, an amino group, or a hydroxyl group. The substituents may be bonded to each other to form a ring. n is an integer between 1 and 3, L is a ligand represented by the structural formula (L0). However, if R 104 is a cyano group, R 102 and R 106 are bonded to substituents. 【Chemistry 2】 (In the above structural formula (L0), R ２０１ ~R ２０８ Each of these is independently hydrogen or an alkyl group having 1 to 6 carbon atoms. Furthermore, in the general formula (G0), all hydrogen atoms may be deuterium.

2. An organic compound represented by the general formula (G1). 【Transformation 3】 (In the above general formula (G1), X is a nitrogen atom or a carbon atom, When X is a carbon atom, X is bonded to hydrogen or a substituent. R １０２ and R １０７ at least one of which is an alkyl group having 1 to 6 carbon atoms, R １０１ ~R １１１ The others are each independently bonded to hydrogen or a substituent. Each of the substituents is independently a C1 to C6 alkyl group, a C3 to C7 cycloalkyl group, a substituted or unsubstituted C6 to C13 aryl group, a substituted or unsubstituted C1 to C5 heteroaryl group, an amino group, or a hydroxyl group. The substituents may be bonded to each other to form a ring. n is an integer between 1 and 3, L is a ligand represented by the structural formula (L1). 【Chemistry 4】 (In the above structural formula (L1), R ２０１ ~R ２０８ Each of these is independently hydrogen or an alkyl group having 1 to 6 carbon atoms. Furthermore, in general formula (G1), all hydrogen atoms may be deuterium.

3. An organic compound represented by the general formula (G2). 【Transformation 5】 (In the above general formula (G2), R １０２ and R １０７ At least one of them is an alkyl group having 1 to 6 carbon atoms. R １０２ ~R １１２ The others are each independently bonded to hydrogen or a substituent. Each of the substituents is independently a C1 to C6 alkyl group, a C3 to C7 cycloalkyl group, a substituted or unsubstituted C6 to C13 aryl group, a substituted or unsubstituted C1 to C5 heteroaryl group, an amino group, or a hydroxyl group. The substituents may be bonded to each other to form a ring. Furthermore, in general formula (G2), all hydrogen atoms may be deuterium.

4. An organic compound represented by the general formula (G3). 【Transformation 6】 (In the above general formula (G3), R １０２ and R １０７ At least one of them is an alkyl group having 1 to 6 carbon atoms. R １０２ ~R １１２ The others are each independently bonded to hydrogen or a substituent. Each of the substituents is independently a C1 to C6 alkyl group, a C3 to C7 cycloalkyl group, a substituted or unsubstituted C6 to C13 aryl group, a substituted or unsubstituted C1 to C5 heteroaryl group, an amino group, or a hydroxyl group. The substituents may be bonded to each other to form a ring. Furthermore, in general formula (G3), all hydrogen atoms may be deuterium.

5. An organic compound represented by the general formula (G4). 【Transformation 7】 (In the above general formula (G4), R １０２ and R １０７ At least one of them is an alkyl group having 1 to 6 carbon atoms. R １０２ ~R １０７ The others are each independently bonded to hydrogen or a substituent. Each of the substituents is independently a C1 to C6 alkyl group, a C3 to C7 cycloalkyl group, a substituted or unsubstituted C6 to C13 aryl group, a substituted or unsubstituted C1 to C5 heteroaryl group, an amino group, or a hydroxyl group. The substituents may be bonded to each other to form a ring. Furthermore, in general formula (G4), all hydrogen atoms may be deuterium.

6. The first electrode and The second electrode and Having a first unit, The first unit is sandwiched between the first electrode and the second electrode, The first unit is a light-emitting device comprising the organic compound described in any one of claims 1 to 5.

7. A first light-emitting device and It has a second light-emitting device, The first light-emitting device comprises a third electrode, a fourth electrode, a second unit, and a first layer. The second unit is sandwiched between the third electrode and the fourth electrode, The first layer is sandwiched between the second unit and the third electrode. The second unit comprises the organic compound described in any one of claims 1 to 5. The first layer comprises a second organic compound or transition metal oxide containing a halogen group or a cyano group. The second light-emitting device is adjacent to the first light-emitting device, The second light-emitting device comprises a fifth electrode, a sixth electrode, a third unit, and a second layer. The fifth electrode has a gap between it and the third electrode, The third unit is sandwiched between the sixth electrode and the fifth electrode, The third unit comprises a luminescent material, The second layer is sandwiched between the third unit and the fifth electrode. The second layer comprises the second organic compound or the transition metal oxide, The second layer has a region between it and the first layer in which the film thickness is thinner than that of the first layer. The aforementioned region is a display device that overlaps with the aforementioned gap.

8. The first functional layer, It has a second functional layer, The first functional layer overlaps with the second functional layer, The first functional layer includes a first pixel circuit and a second pixel circuit, The second functional layer includes a first light-emitting device and a second light-emitting device. The first light-emitting device comprises a third electrode, a fourth electrode, and a second unit. The second unit is sandwiched between the third electrode and the fourth electrode, The second unit comprises the organic compound described in any one of claims 1 to 5. The third electrode is electrically connected to the first pixel circuit. The second light-emitting device comprises a fifth electrode, a sixth electrode, and a third unit. The third unit is sandwiched between the fifth electrode and the sixth electrode, The fifth electrode is electrically connected to the second pixel circuit. The sixth electrode is electrically connected to the fourth electrode, and is a display device.

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