Organic compound, light-emitting device, display apparatus, electronic equipment, light-emitting apparatus, and lighting apparatus

Abstract

To provide a novel organic compound that is highly convenient, useful or reliable.SOLUTION: The organic compound is represented by Formula (G0) in the figure. In Formula (G0), n is 1 or 2, and L represents a ligand represented by General Formula (L0) in the figure. In Formula (L0), R201 to R208 each independently represent hydrogen, deuterium, or the like.SELECTED DRAWING: Figure 1

Description

[Technical Field]

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

[0002] Furthermore, one aspect of the present invention is not limited to the above-mentioned technical field. The technical field of one aspect of the invention disclosed herein relates to a product, method, or method of manufacture. Alternatively, one aspect of the present invention relates to a process, machine, manufacture, or composition of matter. More specifically, examples of the technical field of one aspect of the present invention disclosed herein include semiconductor devices, display devices, light-emitting devices, energy storage devices, memory devices, methods for driving them, or methods for manufacturing them. [Background technology]

[0003] For example, heteroreptic iridium compounds for use as light-emitting materials and light-emitting devices containing them are known (see Patent Document 1). [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2014-162796 [Overview of the project] [Problems that the invention aims to solve]

[0005] One aspect of the present invention aims to provide a novel organic compound that is excellent in convenience, usefulness, or reliability. Alternatively, it aims to provide a novel light-emitting device that is excellent in convenience, usefulness, or reliability. Alternatively, it aims to provide a novel display device that is excellent in convenience, usefulness, or reliability. Alternatively, it aims to provide a novel electronic device that is excellent in convenience, usefulness, or reliability. Alternatively, it aims to provide a novel light-emitting device that is excellent in convenience, usefulness, or reliability. Alternatively, it aims to provide a novel lighting device that is excellent in convenience, usefulness, or reliability. Alternatively, it aims 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] Furthermore, the description of these problems does not preclude the existence of other problems. Moreover, one aspect of the present invention does not need to solve all of these problems. Other problems will naturally become apparent from the description in the specification, drawings, and claims, and it is possible to extract other problems from the description in the specification, drawings, and claims. [Means for solving the problem]

[0007] (1) One aspect of the present invention is an organic compound represented by the general formula (G0).

[0008] [ka] However, in the general formula (G0), R 101 ~R 111 Each of these is independently either hydrogen or an alkyl group having 1 to 6 carbon atoms, n is 1 or 2, and L is a ligand represented by the general formula (L0).

[0009] [ka] Furthermore, in the general formula (L0), R 201 ~R 208 Each of these is independently hydrogen, deuterium, or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may have some or all of its hydrogen atoms deuterated.

[0010] (2) Another aspect of the present invention is an organic compound represented by the general formula (G1-1).

[0011] [ka]

[0012] However, in general formula (G1-1), n ​​is either 1 or 2, and L is a ligand represented by general formula (L0).

[0013] [ka] Furthermore, in the general formula (L0), R 201 ~R 208 Each of these is independently hydrogen, deuterium, or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may have some or all of its hydrogen atoms deuterated.

[0014] (3) Another aspect of the present invention is an organic compound represented by the general formula (G1-2).

[0015] [ka]

[0016] However, in general formula (G1-2), n is either 1 or 2, and L is a ligand represented by general formula (L0).

[0017] [ka]

[0018] Furthermore, in the general formula (L0), R 201 ~R 208 Each of these is independently hydrogen, deuterium, or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may have some or all of its hydrogen atoms deuterated.

[0019] (4) Another aspect of the present invention is the above-mentioned organic compound wherein ligand L comprises an alkyl group in which one or more hydrogen atoms are deuterated.

[0020] (5) In another aspect of the present invention, ligand L is the above-mentioned organic compound represented by structural formula (L1-1).

[0021] [ka]

[0022] (6) In another aspect of the present invention, ligand L is the above-mentioned organic compound represented by structural formula (L1-2).

[0023] [ka]

[0024] This allows for the introduction of a deuterated alkyl group to carbon atoms with high spin density in the triplet excited state, thereby improving the stability of the compound in the excited state. Furthermore, by introducing a deuterated alkyl group to carbon atoms where the distribution of the lowest unoccupied molecular orbital (LUMO) is concentrated, the stability of the compound in the reduced state, where electrons have been accepted into the LUMO, can be improved. Additionally, by introducing a phenyl group to carbon atoms adjacent to carbon atoms where the LUMO distribution is concentrated, the LUMO distribution can be broadened. This also stabilizes the LUMO and improves the stability of the compound in the reduced state. Moreover, the deuterated alkyl group can exert a steric hindrance effect on the phenyl group. Furthermore, it can suppress the rotation of the phenyl group, improving the thermophysical properties of the compound, such as sublimation. It can also suppress vibrations of the compound, suppressing thermal deactivation from the excited state. Furthermore, high luminescence efficiency can be achieved. Additionally, ligands can be selected to create a heteroreptic structure, allowing for adjustment of the emission spectrum shape. Furthermore, the emission spectrum shape can be adjusted to include shorter wavelengths of light compared to a homoreptic structure. Furthermore, the thermophysical properties of the compound, such as sublimation, can be improved. As a result, novel organic compounds with superior convenience, usefulness, or reliability can be provided.

[0025] (7) Another aspect of the present invention is a light-emitting device having a first electrode, a second electrode, and a first unit.

[0026] The first unit is sandwiched between the first electrode and the second electrode, and the first unit contains the above-mentioned organic compound.

[0027] As a result, the first unit contains an organic compound according to one aspect of the present invention. Furthermore, the first unit can be made more readily accepting of holes. Also, because the organic compound according to one aspect of the present invention has a broadened LUMO distribution, the first unit can be made more readily accepting of electrons. Furthermore, the driving voltage of the light-emitting device can be lowered. Additionally, since the light emitted by the organic compound according to one aspect of the present invention includes light with wavelengths shorter than 500 nm, and its emission spectrum extends to a range of wavelengths shorter than 500 nm, it can be used in conjunction with a fluorescent light-emitting material having an absorption spectrum that overlaps with the emission spectrum, for example, a fluorescent light-emitting material with a green emission color, to efficiently transfer energy to the fluorescent light-emitting material. Furthermore, the emission spectrum of the light-emitting device can be broadened. Furthermore, the phenomenon of the brightness of the light-emitting device decreasing 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 superior convenience, usefulness, and reliability can be provided.

[0028] (8) Another aspect of the present invention is a display device having a first light-emitting device and a second light-emitting device.

[0029] The first light-emitting device comprises a first electrode, a second electrode, a first unit, and a first layer. The first unit is sandwiched between the first electrode and the second electrode, and the first layer is sandwiched between the first unit and the first electrode.

[0030] The first unit comprises the above-mentioned organic compound, and the first layer comprises a second organic compound or transition metal oxide containing a halogen group or a cyano group.

[0031] The second light-emitting device is adjacent to the first light-emitting device, and the second light-emitting device comprises a third electrode, a fourth electrode, a second unit, and a second layer. The third electrode has a gap between it and the first electrode, the second unit is sandwiched between the third electrode and the fourth electrode, and the second layer is sandwiched between the second unit and the third electrode.

[0032] The second unit comprises a luminescent material, and the second layer comprises a second organic compound or transition metal oxide.

[0033] Furthermore, 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, and this region overlaps with the gap mentioned above.

[0034] This allows for, for example, suppression of current flowing through a region. It also allows for suppression of current flowing between the first and second layers. Furthermore, it suppresses the phenomenon where an adjacent second light-emitting device unintentionally emits light in conjunction with the operation of the first light-emitting device. As a result, a novel display device with superior convenience, usefulness, and reliability can be provided.

[0035] (9) Another aspect of the present invention is a display device having the above-mentioned light-emitting device and a transistor or substrate.

[0036] (10) Another aspect of the present invention is an electronic device having the above-mentioned display device, a sensor, an operation button, a speaker or a microphone.

[0037] (11) Another aspect of the present invention is a light-emitting device having the above-mentioned light-emitting device and a transistor or substrate.

[0038] (12) Another aspect of the present invention is a lighting device having the above-mentioned light-emitting device and a housing.

[0039] In the drawings attached to this specification, the components are classified by function and shown as independent blocks in block diagrams. However, in reality, it is difficult to completely separate the components by function, and one component may be involved in multiple functions.

[0040] In this specification, the term "light-emitting device" includes image display devices that use light-emitting devices. Furthermore, modules to which connectors, such as anisotropic conductive films or TCPs (Tape Carrier Packages), are attached to light-emitting devices, modules to which printed circuit boards are provided at the end of TCPs, or modules to which ICs (integrated circuits) are directly mounted using the COG (Chip On Glass) method may also be included as light-emitting devices. Additionally, lighting fixtures and the like may have light-emitting devices. [Effects of the Invention]

[0041] According to one aspect of the present invention, a novel organic compound with superior convenience, usefulness, or reliability can be provided. Furthermore, one aspect of the present invention can provide a novel light-emitting device with superior convenience, usefulness, or reliability. Furthermore, one aspect of the present invention can provide a novel display device with superior convenience, usefulness, or reliability. Furthermore, one aspect of the present invention can provide a novel electronic device with superior convenience, usefulness, or reliability. Furthermore, one aspect of the present invention can provide a novel light-emitting device with superior convenience, usefulness, or reliability. Furthermore, one aspect of the present invention can provide a novel lighting device with superior convenience, usefulness, or reliability. Furthermore, a novel organic compound can be provided. Furthermore, a novel light-emitting device can be provided. Furthermore, a novel display device can be provided. Furthermore, a novel electronic device can be provided. Furthermore, a novel light-emitting device can be provided. Furthermore, a novel lighting device can be provided.

[0042] Furthermore, the description of these effects does not preclude the existence of other effects. Moreover, one aspect of the present invention does not necessarily have to possess all of these effects. Other effects will naturally become apparent from the description in the specification, drawings, and claims, and it is possible to extract other effects from the description in the specification, drawings, and claims. [Brief explanation of the drawing]

[0043] [Figure 1] Figures 1(A) and 1(B) illustrate the configuration of a light-emitting device according to an embodiment. [Figure 2] Figures 2(A) and 2(B) illustrate the configuration of a light-emitting device according to an embodiment. [Figure 3] Figures 3(A) and 3(B) illustrate the configuration of a display device according to an embodiment. [Figure 4] Figures 4(A) and 4(B) illustrate the configuration of a display device according to an embodiment. [Figure 5] Figures 5(A) to 5(C) illustrate the configuration of the apparatus according to the embodiment. [Figure 6] Figure 6 is a diagram illustrating the configuration of the apparatus according to the embodiment. [Figure 7] Figures 7(A) and 7(B) illustrate the configuration of the apparatus according to the embodiment. [Figure 8] Figures 8(A) and 8(B) illustrate the configuration of an active matrix type light-emitting device according to an embodiment. [Figure 9] Figures 9(A) and (B) illustrate the configuration of an active matrix type light-emitting device according to an embodiment. [Figure 10] Figure 10 is a diagram illustrating the configuration of an active matrix type light-emitting device according to an embodiment. [Figure 11] Figures 11(A) and (B) illustrate the configuration of a passive matrix type light-emitting device according to an embodiment. [Figure 12] Figures 12(A) and (B) illustrate the configuration of the lighting device according to the embodiment. [Figure 13] Figures 13(A) to (D) illustrate the configuration of the electronic device according to the embodiment. [Figure 14] Figures 14(A) to (C) illustrate the configuration of the electronic device according to the embodiment. [Figure 15] Figure 15 is a diagram illustrating the configuration of a lighting device according to an embodiment. [Figure 16]Figure 16 is a diagram illustrating the configuration of a lighting device according to an embodiment. [Figure 17] Figure 17 is a diagram illustrating the configuration of an in-vehicle display device and lighting device according to an embodiment. [Figure 18] Figures 18(A) to (C) illustrate the configuration of the electronic device according to the embodiment. [Figure 19] Figure 19 illustrates the results of measuring the 1H NMR spectrum of Ir(ppy)2(5m4dppy-d3) in the example. [Figure 20] Figure 20 illustrates the results of measuring the absorption and emission spectra of a dichloromethane solution containing Ir(ppy)2(5m4dppy-d3) according to the example. [Figure 21] Figure 21 illustrates the results of measuring the 1H NMR spectrum of Ir(5m4dppy-d3)2(ppy) in the example. [Figure 22] Figure 22 illustrates the results of measuring the absorption and emission spectra of a dichloromethane solution containing Ir(5m4dppy-d3)2(ppy) according to the example. [Figure 23] Figure 23 illustrates the results of measuring the 1H NMR spectrum of Ir(5iBu4mppy-d5)2(4mmtBup5mppy-d3) in the example. [Figure 24] Figure 24 illustrates the results of measuring the absorption and emission spectra of a dichloromethane solution containing Ir(5iBu4mppy-d5)2(4mmtBup5mppy-d3) according to the example. [Figure 25] Figure 25 is a diagram illustrating the configuration of a light-emitting device according to an embodiment. [Figure 26] Figure 26 illustrates the current density-luminance characteristics of the light-emitting device according to the embodiment. [Figure 27] Figure 27 illustrates the brightness-current efficiency characteristics of the light-emitting device according to the embodiment. [Figure 28] Figure 28 illustrates the voltage-luminance characteristics of the light-emitting device according to the embodiment. [Figure 29] FIG. 29 is a diagram for explaining the voltage-current characteristics of the light-emitting device according to the embodiment. [Figure 30] FIG. 30 is a diagram for explaining the luminance-external quantum efficiency characteristics of the light-emitting device according to the embodiment. [Figure 31] FIG. 31 is a diagram for explaining the emission spectrum of the light-emitting device according to the embodiment. [Figure 32] FIG. 32 is a diagram for explaining the change over time of the normalized luminance of the light-emitting device according to the embodiment. [Figure 33] [[ID=!!]]FIGS. 33(A) and (B) are diagrams for explaining the results of calculating the molecular orbitals of the organic compound.

MODE FOR CARRYING OUT THE INVENTION

[0044] The organic compound of one aspect of the present invention is represented by the general formula (G0).

[0045]

CHEM.

[0046]

CHEM.

[0047] Note: There seems to be a formatting issue in the original text where "図33(A)および(B)は、有機化合物の分子軌道を計算した結果を説明する図である。" is translated as "FIGS. 33(A) and (B) are diagrams for explaining the results of calculating the molecular orbitals of the organic compound." in the provided translation, but the original Chinese text has no "!!" in it. Also, there is an extra " " in the original text which is not translated in the provided output. Please check and correct if needed.As a result, in organic compounds represented by general formula (G0), the meta position of the pyridine ring coordinating to iridium has a high spin density in the triplet excited state, and therefore the compound can be stabilized by substituted with a deuterated alkyl group. Furthermore, in organic compounds represented by general formula (G0), the LUMO distribution is concentrated at the meta position of the pyridine ring coordinating to iridium, and therefore the stability of the compound in the state where electrons have been accepted by the LUMO, i.e., the reduced state, can be improved by substituted with a deuterated alkyl group. Furthermore, in ligands represented by general formula (L0), the spin density is high at the meta position of the pyridine ring coordinating to iridium in the triplet excited state, and therefore the compound can be stabilized by substituted with a deuterated alkyl group. Furthermore, in ligands represented by general formula (L0), the LUMO distribution is concentrated at the meta position of the pyridine ring coordinating to iridium, and therefore the stability of the compound in the state where electrons have been accepted by the LUMO, i.e., the reduced state, can be improved by substituted with a deuterated alkyl group. Furthermore, it is expected to have the effect of adjusting the shape of the emission spectrum to include light of shorter wavelengths. Also, when used with a fluorescent light-emitting material, it can suppress Dexter-type energy transfer from the organic compound represented by general formula (G0) to the fluorescent light-emitting material, and promote Förster-type energy transfer. In addition, in the organic compound represented by general formula (G0), by introducing a phenyl group as a substituent to the carbon atom adjacent to the meta position of the pyridine ring coordinating to iridium, the distribution of the LUMO can be broadened. Furthermore, the LUMO can be stabilized, improving the stability of the compound in the reduced state. Furthermore, the deuterated alkyl group can exhibit a steric hindrance effect on the phenyl group. Furthermore, the rotation of the phenyl group can be suppressed, improving the thermophysical properties of the compound, such as sublimation. Furthermore, vibrations of the compound can be suppressed, suppressing thermal deactivation from the excited state. Furthermore, high luminescence efficiency can be achieved. Additionally, ligands can be selected to create a heteroreptic structure, allowing for adjustment of the shape of the emission spectrum. Furthermore, the shape of the emission spectrum can be adjusted to include light of shorter wavelengths compared to a homoreptic structure.Furthermore, the thermophysical properties of the compound, such as sublimation, can be improved. As a result, novel organic compounds with superior convenience, usefulness, or reliability can be provided.

[0048] Embodiments will be described in detail with reference to the drawings. However, it will be readily apparent to those skilled in the art that the present invention is not limited to the following description, and that its form and details can be modified in various ways without departing from the spirit and scope of the present invention. Accordingly, the present invention is not to be interpreted as being limited to the contents of the embodiments shown below. In the configuration of the invention described below, the same reference numerals are used in common across different drawings for the same parts or parts having similar functions, and repeated descriptions are omitted.

[0049] (Embodiment 1) This embodiment describes an organic compound according to one aspect of the present invention.

[0050] <Example 1 of an organic compound> The organic compound according to one aspect of the present invention described in this embodiment is represented by the general formula (G0).

[0051] [ka]

[0052] However, in the general formula (G0), R 101 ~R 111 Each of these is independently either hydrogen or an alkyl group having 1 to 6 carbon atoms. n is either 1 or 2. Examples of alkyl groups having 1 to 6 carbon atoms include methyl, ethyl, propyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, and hexyl groups. Furthermore, the hydrogen may be deuterated, and some or all of the hydrogen atoms in the alkyl group having 1 to 6 carbon atoms may be deuterated.

[0053] Furthermore, L is a ligand represented by the general formula (L0).

[0054] [ka]

[0055] In the general formula (L0), R 201 ~R 208 Each of these is independently either hydrogen or an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups having 1 to 6 carbon atoms include methyl, ethyl, propyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, and hexyl groups. Furthermore, the hydrogen may be deuterated, and some or all of the hydrogen atoms of the alkyl group having 1 to 6 carbon atoms may be deuterated.

[0056] <Example of an organic compound 2> Furthermore, the organic compound according to one embodiment of the present invention described in this embodiment is represented by the general formula (G1-1).

[0057] [ka]

[0058] However, in the general formula (G1-1), n ​​is either 1 or 2.

[0059] Furthermore, L is a ligand represented by the general formula (L0).

[0060] [ka]

[0061] In the general formula (L0), R 201 ~R 208 Each of these is independently hydrogen, deuterium, or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may have some or all of its hydrogen atoms deuterated.

[0062] Specific examples of organic compounds having the above configuration are shown below.

[0063] [ka]

[0064] <Example 3 of organic compounds> Furthermore, the organic compound according to one embodiment of the present invention described in this embodiment is represented by the general formula (G1-2).

[0065] [ka]

[0066] However, in the general formula (G1-2), n is either 1 or 2.

[0067] Furthermore, L is a ligand represented by the general formula (L0).

[0068] [ka]

[0069] In the general formula (L0), R 201 ~R 208 Each of these is independently hydrogen, deuterium, or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may have some or all of its hydrogen atoms deuterated.

[0070] <Example 4 of organic compounds> Furthermore, the organic compound according to one embodiment of the present invention described in this embodiment comprises a ligand L which is a deuterated alkyl group with one or more hydrogen atoms. This makes it possible to increase the bond dissociation energy of the compound compared to the bond dissociation energy of the carbon-hydrogen bond by utilizing the carbon-deuterium bond. It also makes the molecular structure stable. It also suppresses bond dissociation within the compound structure in the excited state. Furthermore, it suppresses the degradation or alteration of the compound due to the dissociation of the carbon-deuterium bond. It can also be suitably used, for example, in the light-emitting layer of a light-emitting device. It can also be suitably used, for example, in a layer in contact with the light-emitting layer of a light-emitting device.

[0071] <Example 5 of organic compounds> Furthermore, in one embodiment of the present invention described in this embodiment, the ligand L is represented by the structural formula (L1-1).

[0072] [ka]

[0073] Specific examples of organic compounds having the above configuration are shown below.

[0074] [ka]

[0075] <Example 6 of organic compounds> Furthermore, in one embodiment of the present invention described in this embodiment, the ligand L is represented by the structural formula (L1-2).

[0076] [ka]

[0077] Specific examples of organic compounds having the above configuration are shown below.

[0078] [ka]

[0079] This allows for the introduction of a deuterated alkyl group to carbon atoms with high spin density in the triplet excited state, thereby improving the stability of the compound in the excited state. Furthermore, by introducing a deuterated alkyl group to carbon atoms where the LUMO distribution is concentrated, the stability of the compound in the reduced state, i.e., the state where electrons have been accepted by the LUMO, can be improved. Additionally, by introducing a phenyl group to carbon atoms adjacent to those where the LUMO distribution is concentrated, the LUMO distribution can be broadened. This also stabilizes the LUMO and improves the stability of the compound in the reduced state. Furthermore, the deuterated alkyl group can exert a steric hindrance effect on the phenyl group. This can also suppress the rotation of the phenyl group, improving the thermal properties of the compound, such as sublimation. It can also suppress vibrations of the compound, suppressing thermal deactivation from the excited state. High luminescence efficiency can also be achieved. Furthermore, ligands can be selected to create a heteroreptic structure, allowing for adjustment of the emission spectrum shape. The emission spectrum shape can also be adjusted to include shorter wavelengths of light compared to a homoreptic structure. Finally, the thermal properties of the compound, such as sublimation, can be improved. As a result, it is possible to provide novel organic compounds that are superior in terms of convenience, usefulness, or reliability.

[0080] <Examples of methods for synthesizing organic compounds> A method for synthesizing an organic compound according to one embodiment of the present invention will be described. However, the synthesis method is not limited to this. It can also be synthesized using other synthesis methods or known synthesis methods.

[0081] An organic compound according to one aspect of the present invention is represented by the general formula (G0).

[0082] [ka]

[0083] However, in the general formula (G0), R 101~R 111 Each of these is independently either hydrogen or an alkyl group having 1 to 6 carbon atoms.

[0084] Furthermore, L is a ligand represented by the general formula (L0).

[0085] [ka]

[0086] In the general formula (L0), R 201 ~R 208 Each of these is independently hydrogen, deuterium, or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may have some or all of its hydrogen atoms deuterated.

[0087] Method for synthesizing organic compounds represented by general formula (G0) For example, an organic compound according to one embodiment of the present invention can be synthesized by reacting a dinuclear complex (A) with a pyridine compound (B) under an inert gas atmosphere (see synthesis scheme (a)).

[0088] [ka]

[0089] In the above synthesis scheme (a), X represents a halogen, and the dinuclear complex (A) has a structure bridged with the halogen. Also, R 201 ~R 208 Each of these is independently hydrogen, deuterium, or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may have some or all of its hydrogen atoms deuterated.

[0090] Furthermore, pyridine compound (B) is R 101 ~R 111 It has R 101 ~R 111 Each of these is independently either a hydrogen atom or an alkyl group having between 1 and 6 carbon atoms. Also, n is either 1 or 2.

[0091] Furthermore, the organic compound obtained by the above method may be further irradiated with light or heat to obtain geometric isomers, optical isomers, and other isomers, which are also organic compounds according to one embodiment of the present invention, represented by the general formula (G0).

[0092] Alternatively, a dinuclear complex (A) having a halogen-bridged structure may be reacted with a dehalogenating agent such as silver trifluoromethanesulfonate to precipitate silver halide, and then the supernatant liquid may be reacted with a pyridine compound (B) under an inert gas atmosphere.

[0093] Furthermore, various types of dinuclear complexes (A), various types of pyridine compounds (B), and various types of ligands represented by the general formula (L0) are commercially available and can also be synthesized. As a result, a wide variety of organic compounds can be synthesized using the method described above. In addition, the organic compound according to one embodiment of the present invention, represented by the general formula (G0), is characterized by a rich variety of ligands.

[0094] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0095] (Embodiment 2) In this embodiment, the configuration of a light-emitting device 550X according to one aspect of the present invention will be described with reference to Figures 1(A) and (B).

[0096] Figure 1(A) is a cross-sectional view illustrating the configuration of a light-emitting device 550X according to one embodiment of the present invention, and Figure 1(B) is a diagram illustrating the energy levels of the material used in the light-emitting device 550X according to one embodiment of the present invention.

[0097] <Example configuration of the 550X light-emitting device> The light-emitting device 550X described in this embodiment includes an electrode 551X, an electrode 552X, and a unit 103X. Electrode 552X overlaps with electrode 551X, and unit 103X is sandwiched between electrodes 552X and 551X.

[0098] <Example configuration of Unit 103X> Unit 103X has a single-layer or multi-layer structure. For example, unit 103X has layers 111X, 112, and 113 (see Figure 1(A)). Unit 103X has the function of emitting optical ELX.

[0099] Layer 111X is sandwiched between layers 113 and 112, layer 113 is sandwiched between electrode 552X and layer 111X, and layer 112 is sandwiched between layer 111X and electrode 551X.

[0100] For example, a layer selected from functional layers such as an emissive layer, a hole transport layer, an electron transport layer, and a carrier block layer can be used in unit 103X. Furthermore, a layer selected from functional layers such as a hole injection layer, an electron injection layer, an exciton block layer, and a charge generation layer can also be used in unit 103X.

[0101] Example of Layer 112 configuration For example, a material with hole-transporting properties can be used for layer 112. Layer 112 can also be referred to as a hole-transporting layer. It is preferable to use a material for layer 112 that has a larger band gap than the luminescent material contained in layer 111X. This suppresses energy transfer from excitons generated in layer 111X to layer 112.

[0102] [Materials with hole transport properties] The hole mobility is 1 × 10⁻⁶. -6 cm 2 Materials with a Vs of / Vs or higher can be suitably used as materials with hole transport properties.

[0103] For example, amine compounds or organic compounds having a π-electron-rich heteroaromatic ring skeleton can be used in hole-transporting materials. Specifically, compounds having an aromatic amine skeleton, a carbazole skeleton, a thiophene skeleton, a furan skeleton, etc., can be used. Compounds having an aromatic amine skeleton or a carbazole skeleton are particularly preferred because they offer good reliability, high hole transportability, and contribute to reducing the driving voltage.

[0104] Examples of compounds having an aromatic amine skeleton include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminobiphenyl (abbreviated as TPD), N,N'-bis(9,9'-spirobio[9H-fluoren]-2-yl)-N,N'-diphenyl-4,4'-diaminobiphenyl (abbreviated as BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated as BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated as mBPAFLP), and 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCBA1BP). 4,4'-diphenyl-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCBNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]fluoren-2-amine (abbreviated as PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9'-spirobio[9H-fluoren]-2-amine (abbreviated as PCBASF), etc. can be used.

[0105] Examples of compounds having a carbazole skeleton include 1,3-bis(N-carbazolyl)benzene (abbreviated as mCP), 4,4'-di(N-carbazolyl)biphenyl (abbreviated as CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviated as CzTP), 9,9'-diphenyl-9H,9'H-3,3'-bicarbazole (abbreviated as PCCP), and the like.

[0106] Examples of compounds having a thiophene skeleton include 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviated as DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviated as DBTFLP-III), 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviated as DBTFLP-IV), and others.

[0107] Examples of compounds having a furan skeleton 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 others.

[0108] Example of Layer 113 configuration For example, electron-transporting materials, materials with an anthracene skeleton, and mixed materials can be used for layer 113. Layer 113 can also be referred to as an electron transport layer. It is preferable to use a material for layer 113 that has a larger band gap than the luminescent material contained in layer 111X. This suppresses energy transfer from excitons generated in layer 111X to layer 113.

[0109] [Materials with electron transport properties] For example, under the condition that the square root of the electric field strength [V / cm] is 600, the electron mobility is 1 × 10⁻⁶. -7 cm 2 / Vs or more, 5×10 -5 cm 2 Materials with a Vs of 0.5 or less can be suitably used as electron-transporting materials. This makes it possible to suppress electron transport in the electron transport layer, control the amount of electrons injected into the light-emitting layer, or prevent the light-emitting layer from becoming electron-excessive.

[0110] For example, metal complexes or organic compounds having a π-electron-deficient heteroaromatic ring skeleton can be used as electron-transporting materials.

[0111] Examples of metal complexes that can be used include bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviated as BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviated as BAlq), bis(8-quinolinolato)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviated as ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviated as ZnBTZ), and the like.

[0112] Organic compounds having a π-electron-deficient heteroaromatic ring skeleton include, for example, 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 a pyridine skeleton are preferred due to their good reliability. Furthermore, heterocyclic compounds having a diazine (pyrimidine or pyrazine) skeleton have high electron transport properties, which can reduce the driving voltage.

[0113] Examples of heterocyclic compounds having a polyazole skeleton include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviated as TAZ), and 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as O XD-7), 9-[4-(5-phenyl-1,3,4-oxadiazole-2-yl)phenyl]-9H-carbazole (abbreviated as CO11), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviated as TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviated as mDBTBIm-II), etc. can be used.

[0114] 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), and 2-[3'-(9H-carbazole-9-yl)biphenyl-3-yl]dibenzo[f,h Quinoxaline (abbreviation: 2mCzBPDBq), 4,6-bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,8-bis[3-(dibenzothiophen-4-yl)phenyl]benzo[h]quinazoline (abbreviation: 4,8mDBtP2Bqn), etc. can be used.

[0115] Examples of heterocyclic compounds having a pyridine skeleton include 3,5-bis[3-(9H-carbazole-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), and others.

[0116] 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) and 2-[(1,1'-biphenyl)-4-yl]-4-phenyl-6-[9,9'-spirobi(9H-fluoren)-2-yl]-1,3,5-triazine (abbreviation: BP-SFT). You can use compounds such as 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), etc.

[0117] [Materials containing an anthracene skeleton] Organic compounds having an anthracene skeleton can be used in layer 113. In particular, organic compounds containing both an anthracene skeleton and a heterocyclic skeleton can be preferably used.

[0118] For example, an organic compound containing both an anthracene skeleton and a nitrogen-containing five-membered ring skeleton can be used in layer 113. Alternatively, an organic compound containing both a nitrogen-containing five-membered ring skeleton with two heteroatoms in the ring and an anthracene skeleton can be used in layer 113. Specifically, pyrazole rings, imidazole rings, oxazole rings, thiazole rings, etc., can be suitably used as the heterocyclic skeleton.

[0119] Furthermore, for example, an organic compound containing both an anthracene skeleton and a nitrogen-containing six-membered ring skeleton can be used in layer 113. Alternatively, an organic compound containing both a nitrogen-containing six-membered ring skeleton with two heteroatoms in the ring and an anthracene skeleton can be used in layer 113. Specifically, pyrazine rings, pyrimidine rings, pyridazine rings, etc., can be suitably used as the heterocyclic skeleton.

[0120] [Example of mixed material composition] Furthermore, a material composed of a mixture of multiple substances can be used in layer 113. Specifically, a mixed material containing an alkali metal, alkali metal compound, or alkali metal complex and an electron-transporting substance can be used in layer 113. It is more preferable that the highest occupied molecular orbital (HOMO) level of the electron-transporting material is -6.0 eV or higher.

[0121] Furthermore, the mixed material can be suitably used in layer 113 in combination with a configuration in which a composite material, as described separately, is used in layer 104. For example, a composite material of an electron-accepting material and a hole-transporting material can be used in layer 104. Specifically, a composite material of an electron-accepting material and a material having a relatively deep HOMO level HM1 between -5.7 eV and -5.4 eV can be used in layer 104 (see Figure 1(B)). By using the mixed material in layer 113 in combination with a configuration in which such a composite material is used in layer 104, the reliability of the light-emitting device can be improved.

[0122] Furthermore, it is preferable to combine the configuration in which the mixed material is used in layer 113 and the composite material in layer 104 with a configuration in which a hole-transporting material is used in layer 112. For example, a material having a HOMO level HM2 in the range of -0.2eV to 0eV relative to the relatively deep HOMO level HM1 can be used in layer 112 (see Figure 1(B)). This can improve the reliability of the light-emitting device. In this specification, the above light-emitting device may be referred to as a Recombination-Site Tailoring Injection structure (ReSTI structure).

[0123] A configuration in which alkali metals, alkali metal compounds, or alkali metal complexes are present in the thickness direction of layer 113 with a concentration difference (including cases where the concentration is zero) is preferred.

[0124] For example, metal complexes containing an 8-hydroxyquinolinate structure can be used. Alternatively, methyl-substituted metal complexes containing an 8-hydroxyquinolinate structure (e.g., 2-methyl-substituted or 5-methyl-substituted) can also be used.

[0125] As metal complexes containing the 8-hydroxyquinolinate structure, 8-hydroxyquinolinate-lithium (abbreviated as Liq), 8-hydroxyquinolinate-sodium (abbreviated as Naq), etc., can be used. In particular, monovalent metal ion complexes are preferred, among lithium complexes, and Liq is more preferred.

[0126] 《Example of Layer 111X Configuration 1》 For example, a luminescent material, or a luminescent material and a host material, can be used for layer 111X. Layer 111X can also be referred to as a light-emitting layer. It is preferable to place layer 111X in the region where holes and electrons recombine. This allows the energy generated by carrier recombination to be efficiently emitted as light.

[0127] Furthermore, it is preferable to position layer 111X away from the metal used for electrodes, etc. This makes it possible to suppress the quenching phenomenon caused by the metal used for electrodes, etc.

[0128] Furthermore, it is preferable to adjust the distance from the reflective electrodes, etc., to the layer 111X and position the layer 111X at an appropriate location according to the emission wavelength. This allows for the amplification of the light amplitudes by utilizing the interference phenomenon between the light reflected by the electrodes, etc., and the light emitted by the layer 111X. In addition, it is possible to strengthen light of a predetermined wavelength and narrow the light spectrum. Furthermore, a vivid emission color can be obtained with high intensity. In other words, by positioning the layer 111X at an appropriate location between the electrodes, etc., a microcavity structure can be constructed.

[0129] For example, phosphorescent materials can be used as luminescent materials. This allows the energy generated by carrier recombination to be released from the luminescent material as photo-ELX (see Figure 1(A)).

[0130] [Phosphorescent material] A phosphorescent material can be used in layer 111X. For example, an organic compound according to one embodiment of the present invention described in Embodiment 1 can be used in layer 111X.

[0131] 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-d3)-2-pyridinyl-κN]phenyl-κC}bis{2-[4-(methyl-d3)-5-(2-methylpropyl-1,1-d2)-2-pyridinyl-κN]phenyl-κC}iridium(III) (abbreviation: Ir(5iBu4mppy-d5)2(4mmtBup5mppy-d3)), etc., can be used in layer 111X.

[0132] As a result, layer 111X contains an organic compound according to one embodiment of the present invention. Furthermore, layer 111X can be made more readily acceptable of holes. Also, because the organic compound according to one embodiment of the present invention has a broadened LUMO distribution, layer 111X can be made more readily acceptable of electrons. Furthermore, the driving voltage of the light-emitting device can be lowered. Furthermore, the emission spectrum of the light-emitting device can be broadened. Furthermore, the phenomenon of the brightness of the light-emitting device decreasing 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 superior convenience, usefulness, and reliability can be provided.

[0133] 《Example of Layer 111X Configuration 2》 Materials with carrier transport properties can be used as the host material. For example, materials with hole transport properties, materials with electron transport properties, materials that exhibit thermally activated delayed fluorescence (TADF) (also called TADF materials), materials with an anthracene skeleton, and mixed materials can be used as the host material. It is preferable to use a material with a larger band gap than the luminescent material contained in layer 111X as the host material. This makes it possible to suppress energy transfer from excitons generated in layer 111X to the host material.

[0134] [Materials with hole transport properties] The hole mobility is 1 × 10⁻⁶. -6 cm 2 Materials with a Vs of 1 / Vs or higher can be suitably used as hole-transporting materials. For example, a hole-transporting material that can be used in layer 112 can be used as a host material.

[0135] [Materials with electron transport properties] Metal complexes or organic compounds having a π-electron-deficient heteroaromatic ring skeleton can be used as electron-transporting materials. For example, an electron-transporting material that can be used in layer 113 can be used as a host material.

[0136] [Example of mixed material composition 1] Furthermore, a material composed of a mixture of multiple substances can be used as the host material. For example, a material with electron-transporting properties and a material with hole-transporting properties can be used in the mixture. The weight ratio of the material with hole-transporting properties to the material with electron-transporting properties in the mixture should be (material with hole-transporting properties / material with electron-transporting properties) = (1 / 19) or more and (19 / 1) or less. This allows for easy adjustment of the carrier transport properties of layer 111X. In addition, the recombination region can be easily controlled.

[0137] [Example of mixed material composition 2] An organic compound according to one aspect of the present invention can be used as a host material. The organic compound according to one aspect of the present invention is a phosphorescent material, and the phosphorescent material can be used as an energy donor that provides excitation energy to a fluorescent material when a fluorescent material is used as the light-emitting material.

[0138] As a result, the light emitted by the organic compound according to one aspect of the present invention includes light with wavelengths shorter than 500 nm, and its emission spectrum extends to a range of wavelengths shorter than 500 nm. Therefore, when used together with a fluorescent light-emitting material having an absorption spectrum that overlaps with the emission spectrum, for example, a fluorescent light-emitting material with a green emission color, energy can be efficiently transferred to the fluorescent light-emitting material. Furthermore, the phenomenon of the brightness of the light-emitting device decreasing with use can be suppressed. In addition, the reliability of the light-emitting device can be improved. As a result, a novel light-emitting device with superior convenience, usefulness, and reliability can be provided.

[0139] [Example of mixed material composition 3] A mixed material containing a material that forms an excited complex can be used as the host material. For example, a material in which the emission spectrum of the formed excited complex overlaps with the wavelength of the lowest energy absorption band of the luminescent material can be used as the host material. This allows for smoother energy transfer and improves luminescence efficiency. Alternatively, the driving voltage can be suppressed. With such a configuration, luminescence using ExTET (Exciplex-Triplet Energy Transfer), which is energy transfer from the excited complex to the luminescent material (phosphorescent material), can be efficiently obtained.

[0140] A phosphorescent material can be used in at least one of the materials forming the excitation complex. This allows for the utilization of reverse intersystem crossing. Alternatively, the triplet excitation energy can be efficiently converted to the singlet excitation energy.

[0141] For a combination of materials to form an excited complex, it is preferable that the HOMO level of the hole-transporting material is higher than or equal to the HOMO level of the electron-transporting material. Alternatively, it is preferable that the LUMO level of the hole-transporting material is higher than or equal to the LUMO level of the electron-transporting material. This allows for efficient formation of the excited complex. The LUMO and HOMO levels of the materials can be derived from their electrochemical properties (reduction potential and oxidation potential). Specifically, the reduction potential and oxidation potential can be measured using cyclic voltammetry (CV) measurement.

[0142] The formation of excited complexes can be confirmed, for example, by comparing the emission spectra of a hole-transporting material, an electron-transporting material, and a mixed film made by mixing these materials, and observing that the emission spectrum of the mixed film shifts to a longer wavelength than the emission spectra of each individual material (or has a new peak on the longer wavelength side). Alternatively, it can be confirmed by comparing the transient photoluminescence (PL) of a hole-transporting material, the transient PL of an electron-transporting material, and the transient PL of a mixed film made by mixing these materials, and observing differences in the transient response, such as the transient PL lifetime of the mixed film having a longer lifetime component or a larger proportion of the delayed component than the transient PL lifetime of each individual material. Furthermore, the transient PL mentioned above can be replaced with transient electroluminescence (EL). That is, the formation of excited complexes can also be confirmed by comparing the transient EL of a hole-transporting material, the transient EL of an electron-transporting material, and the transient EL of a mixed film made by mixing these materials, and observing the differences in the transient response.

[0143] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0144] (Embodiment 3) In this embodiment, the configuration of a light-emitting device 550X according to one aspect of the present invention will be described with reference to Figures 1(A) and 1(B).

[0145] <Example configuration of the 550X light-emitting device> The light-emitting device 550X described in this embodiment includes an electrode 551X, an electrode 552X, a unit 103X, and a layer 104. Electrode 552X overlaps with electrode 551X, and unit 103X is sandwiched between electrodes 551X and 552X. Layer 104 is also sandwiched between electrode 551X and unit 103X. For example, the configuration described in Embodiment 2 can be used for unit 103X.

[0146] <Example configuration of electrode 551X> For example, conductive materials can be used for electrode 551X. Specifically, films containing metals, alloys, or conductive compounds can be used for electrode 551X in a single layer or multilayer configuration.

[0147] For example, a film that efficiently reflects light can be used for electrode 551X. Specifically, an alloy containing silver and copper, an alloy containing silver and palladium, or a metal film such as aluminum can be used for electrode 551X.

[0148] Furthermore, for example, a metal film that transmits some of the light and reflects other parts of the light can be used for the electrode 551X. This allows for the creation of a microcavity structure in the light-emitting device 550X. Alternatively, it may be possible to extract light of a predetermined wavelength more efficiently than other light. Alternatively, it may be possible to extract light with a narrow spectral full width at half maximum. Alternatively, it may be possible to extract light of vivid colors.

[0149] Furthermore, for example, a film that is transparent to visible light can be used for the electrode 551X. Specifically, a thin metal film, alloy film, or conductive oxide film that is thin enough to transmit light can be used for the electrode 551X in a single layer or in a multilayer structure.

[0150] In particular, materials with a work function of 4.0 eV or higher can be suitably used for electrode 551X.

[0151] For example, conductive oxides containing indium can be used. Specifically, indium oxide, indium oxide-tin oxide (abbreviated as ITO), indium oxide-tin oxide containing silicon or silicon oxide (abbreviated as ITSO), indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide (abbreviated as IWZO), etc., can be used.

[0152] Furthermore, conductive oxides containing zinc can be used, for example. Specifically, zinc oxide, zinc oxide with added gallium, and zinc oxide with added aluminum can be used.

[0153] In addition, for example, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), or nitrides of metallic materials (e.g., titanium nitride) can be used. Alternatively, graphene can be used.

[0154] 《Example of Layer 104 Configuration 1》 For example, a material with hole-injection properties can be used for layer 104. Layer 104 can also be referred to as a hole-injection layer.

[0155] For example, when the square root of the electric field strength [V / cm] is 600, the hole mobility is 1 × 10⁻⁶. -3 cm 2 Materials with a Vs of 1 × 10 can be used in 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 layer 104. Preferably, layer 104 is 5 × 10 4 [Ω cm] or more 1×10 7 Having an electrical resistivity of [Ω·cm] or less, more preferably 1 × 10⁻⁶ 5 [Ω cm] or more 1×10 7 It has an electrical resistivity of [Ω·cm] or less.

[0156] 《Example of Layer 104 Configuration 2》 Specifically, an electron-accepting material can be used in layer 104. Alternatively, a composite material containing multiple types of materials can be used in layer 104. This makes it easier to inject holes, for example, from electrode 551X. Alternatively, the driving voltage of light-emitting device 550X can be reduced.

[0157] [Substances with electron-accepting properties] Organic and inorganic compounds can be used as electron-accepting materials. Electron-accepting materials can extract electrons from adjacent hole transport layers or hole-transporting materials by applying an electric field.

[0158] For example, compounds having electron-withdrawing groups (halogen groups or cyano groups) can be used in electron-accepting materials. Furthermore, electron-accepting organic compounds are easily vapor-deposited and readily formed into films. This can increase the productivity of the 550X light-emitting device.

[0159] Specifically, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviated as F4-TCNQ), chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviated as HAT-CN), 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviated as F6-TCNNQ), 2-(7-dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyrene-2-ylidene)malononitrile, etc. can be used.

[0160] In particular, compounds in which an electron-withdrawing group is bonded to a condensed aromatic ring having multiple heteroatoms, such as HAT-CN, are thermally stable and therefore preferred.

[0161] Furthermore, radialene derivatives having electron-withdrawing groups (especially halogen groups such as fluoro groups or cyano groups) [3] are preferred because they have very high electron-accepting properties.

[0162] Specifically, α,α',α''-1,2,3-cyclopropanetriylidenates[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α',α''-1,2,3-cyclopropanetriylidenates[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], α,α',α''-1,2,3-cyclopropanetriylidenates[2,3,4,5,6-pentafluorobenzeneacetonitrile], etc., can be used.

[0163] Furthermore, transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide can be used in materials that have electron-accepting properties.

[0164] Furthermore, phthalocyanine-based complex compounds such as phthalocyanine (abbreviated as H2Pc) and copper phthalocyanine (CuPc), and compounds having an aromatic amine skeleton such as 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated as DPAB) and N,N'-bis[4-bis(3-methylphenyl)aminophenyl]-N,N'-diphenyl-4,4'-diaminobiphenyl (abbreviated as DNTPD) can be used.

[0165] Furthermore, polymers such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) can be used.

[0166] [Example of composite material composition 1] Furthermore, for example, a composite material containing an electron-accepting substance and a hole-transporting material can be used for layer 104. This allows not only materials with a large work function but also materials with a small work function to be used for electrode 551X. Alternatively, the material to be used for electrode 551X can be selected from a wide range of materials, regardless of the work function.

[0167] For example, compounds having an aromatic amine skeleton, carbazole derivatives, aromatic hydrocarbons, aromatic hydrocarbons having a vinyl group, and polymer compounds (oligomers, dendrimers, polymers, etc.) can be used as hole transport materials in composite materials. Furthermore, if the hole mobility is 1 × 10⁻⁶ -6 cm 2 Materials with a Vs of 1 / Vs or higher can be suitably used as hole-transporting materials in composite materials. For example, a hole-transporting material that can be used in layer 112 can be used in composite materials.

[0168] Furthermore, materials with relatively deep HOMO levels can be suitably used as hole-transporting materials in composite materials. Specifically, it is preferable that the HOMO level is between -5.7 eV and -5.4 eV. This facilitates the injection of holes into unit 103X. It also facilitates the injection of holes into layer 112. In addition, it improves the reliability of the light-emitting device 550X.

[0169] Examples of compounds having an aromatic amine skeleton include N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviated as DTDPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated as DPAB), N,N'-bis[4-bis(3-methylphenyl)aminophenyl]-N,N'-diphenyl-4,4'-diaminobiphenyl (abbreviated as DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviated as DPA3B).

[0170] Examples of carbazole derivatives include 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarb You can use zole (abbreviated as PCzPCN1), 4,4'-di(N-carbazolyl)biphenyl (abbreviated as CBP), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene (abbreviated as TCPB), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as CzPA), 1,4-bis[4-(N-carbazolyl)phenyl]-2,3,5,6-tetraphenylbenzene, etc.

[0171] 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), and 2-tert-butyl-9,10 -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, etc. can be used.

[0172] Examples of aromatic hydrocarbons having a vinyl group include 4,4'-bis(2,2-diphenylvinyl)biphenyl (abbreviated as DPVBi), 9,10-bis[4-(2,2-diphenylvinyl)phenyl]anthracene (abbreviated as DPVPA), and the like.

[0173] Examples of polymer compounds that can be used include poly(N-vinylcarbazole) (abbreviated as PVK), poly(4-vinyltriphenylamine) (abbreviated as PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated as PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated as Poly-TPD), and the like.

[0174] Furthermore, for example, substances comprising any of the carbazole skeleton, dibenzofuran skeleton, dibenzothiophene skeleton, and anthracene skeleton can be suitably used as hole-transporting materials in composite materials. In addition, substances comprising aromatic amines having substituents including a dibenzofuran ring or a dibenzothiophene ring, aromatic monoamines having a naphthalene ring, or aromatic monoamines in which a 9-fluorenyl group is bonded to the nitrogen of the amine via an arylene group can be used as hole-transporting materials in composite materials. Moreover, using a substance having an N,N-bis(4-biphenyl)amino group can improve the reliability of the light-emitting device 550X.

[0175] 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), and 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'-(carbazole-9-yl)biphenyl-4-yl]triphenylamine (abbreviation: YGTBi1BP), 4'-[4-(3-phenyl-9H-carbazole-9-yl)phenyl] Ris(1,1'-biphenyl-4-yl)amine (abbreviation: YGTBi1BP-02), 4-[4'-(carbazole-9-yl)biphenyl-4-yl]-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: YGTBiβNB), N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-N-[4-(1-naphthyl)phenyl]-9,9'-spirobio[9H-fluorene]-2-amine (abbreviation: PCBNBSF), N,N-bis (biphenyl-4-yl)-9,9'-spirobio[9H-fluorene]-2-amine (abbreviation: BBASF), N,N-bis(biphenyl-4-yl)-9,9'-spirobio[9H-fluorene]-4-amine (abbreviation: BBASF(4)), N-(1,1'-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobio[9H-fluorene]-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-carbazole-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1 -Naphthyl)-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBNBB), N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: PCBASF), N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H-fluorene-2-amine (abbreviation: PCBBiF), N,N-bis( 9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio-9H-fluoren-4-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio-9H-fluoren-3-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio-9H-fluoren-2-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio-9H-fluoren-1-amine, etc. can be used.

[0176] [Example of composite material composition 2] For example, a composite material containing an electron-accepting substance, a hole-transporting material, and an alkali metal fluoride or alkaline earth metal fluoride can be used as a hole-injecting material. In particular, a composite material in which fluorine atoms make up 20% or more of the atomic ratio can be suitably used. This can lower the refractive index of 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.

[0177] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0178] (Embodiment 4) In this embodiment, the configuration of a light-emitting device 550X according to one aspect of the present invention will be described with reference to Figures 1(A) and 1(B).

[0179] <Example configuration of the 550X light-emitting device> The light-emitting device 550X described in this embodiment includes an electrode 551X, an electrode 552X, a unit 103X, and a layer 105. Electrode 552X has a region that overlaps with electrode 551X, and unit 103X has a region sandwiched between electrodes 551X and 552X. Layer 105 also has a region sandwiched between unit 103X and electrode 552X. For example, the configuration described in Embodiment 2 can be used for unit 103X.

[0180] <Example configuration of electrode 552X> For example, conductive materials can be used for electrode 552X. Specifically, materials containing metals, alloys, or conductive compounds can be used for electrode 552X in a single layer or in a multilayer structure.

[0181] For example, the material that can be used for electrode 551X described in Embodiment 3 can be used for electrode 552X. In particular, a material with a smaller work function than electrode 551X can be suitably used for electrode 552X. Specifically, a material with a work function of 3.8 eV or less is preferred.

[0182] 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 electrode 552X.

[0183] Specifically, lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), strontium (Sr), europium (Eu), ytterbium (Yb), and alloys containing these elements, such as a magnesium-silver alloy or an aluminum-lithium alloy, can be used in electrode 552X.

[0184] Example of Layer 105 configuration For example, an electron-injection material can be used for layer 105. Layer 105 can also be referred to as an electron-injection layer.

[0185] Specifically, electron-donating materials can be used in layer 105. Alternatively, a composite material of an electron-donating material and an electron-transporting material can be used in layer 105. Alternatively, an electride can be used in layer 105. This makes it easier to inject electrons from electrode 552X, for example. Alternatively, materials with a large work function, not just a small work function, can be used in electrode 552X. Alternatively, a material for electrode 552X can be selected from a wide range of materials, regardless of the work function. Specifically, Al, Ag, ITO, silicon, or indium oxide-tin oxide containing silicon oxide can be used in electrode 552X. Alternatively, the driving voltage of the light-emitting device 550X can be reduced.

[0186] [Substances that possess electron-donating properties] For example, an alkali metal, an alkaline earth metal, a rare earth metal, or a compound thereof (such as an oxide, a halide, a carbonate, etc.) can be used as a substance having an electron-donating property. Alternatively, an organic compound such as tetrathianaphthacene (abbreviation: TTN), nickelocene, decamethylnickelocene, etc. can also be used as a substance having an electron-donating property.

[0187] As the alkali metal compound (including an oxide, a halide, a carbonate), lithium oxide, lithium fluoride (LiF), cesium fluoride (CsF), lithium carbonate, cesium carbonate, 8-hydroxyquinolinate-lithium (abbreviation: Liq), etc. can be used.

[0188] As the alkaline earth metal compound (including an oxide, a halide, a carbonate), calcium fluoride (CaF2), etc. can be used.

[0189] [Composite material composition example 1] Moreover, a material obtained by compounding a plurality of substances can be used as a material having an electron-injecting property. For example, a substance having an electron-donating property and a material having an electron-transporting property can be used in the composite material.

[0190] [Material having an electron-transporting property] For example, under the condition that the square root of the electric field strength [V / cm] is 600, a material having an electron mobility of 1×10 -7 cm 2 / Vs or more and 5×10 -5 cm 2 / Vs or less can be suitably used as a material having an electron-transporting property. Thereby, the amount of electrons injected into the light-emitting layer can be controlled. Alternatively, it is possible to prevent the light-emitting layer from being in a state of excessive electrons.

[0191] A metal complex or an organic compound having a π-electron-deficient heteroaromatic ring skeleton can be used as a material having an electron-transporting property. For example, a material having an electron-transporting property that can be used for layer 113 can be used in the composite material.

[0192] [Example of composite material composition 2] Furthermore, a composite material can be made from a microcrystalline alkali metal fluoride and an electron-transporting material. Alternatively, a composite material can be made from a microcrystalline alkaline earth metal fluoride and an electron-transporting material. In particular, a composite material containing 50 wt% or more of alkali metal fluoride or alkaline earth metal fluoride can be suitably used. Alternatively, a composite material containing an organic compound having a bipyridine skeleton can be suitably used. This can reduce the refractive index of layer 105, or improve the external quantum efficiency of the light-emitting device 550X.

[0193] [Example of composite material composition 3] For example, a composite material containing a first organic compound having lone pairs of electrons and a first metal can be used for layer 105. Furthermore, it is preferable that the sum of the number of electrons in the first organic compound and the first metal is odd. The molar ratio of the first metal to one 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.

[0194] This allows the first organic compound, which has a lone pair of electrons, to interact with the first metal and form a partially occupied molecular orbital (SOMO). Furthermore, it reduces the barrier between the two when injecting electrons from electrode 552X into layer 105.

[0195] Furthermore, the spin density measured using electron spin resonance (ESR) is preferably 1 × 10⁻⁶. 16 spins / cm 3 The above is more comfortable 5x10 16 spins / cm 3 More preferably 1 × 10 17 spins / cm 3 The composite material described above can be used for layer 105.

[0196] [Organic compounds with lone pairs of electrons] For example, electron-transporting materials can be used in organic compounds containing lone pairs of electrons. For instance, compounds having electron-deficient heteroaromatic rings can be used. Specifically, compounds having at least one of a pyridine ring, a diazine ring (pyrimidine ring, pyrazine ring, pyridazine ring), or a triazine ring can be used. This allows for a reduction in the driving voltage of the light-emitting device 550X.

[0197] Furthermore, it is preferable that the LUMO level of the organic compound containing a lone pair of electrons is between -3.6 eV and -2.3 eV. In general, the HOMO and LUMO levels of the organic compound can be estimated by methods such as cyclic voltammetry (CV), photoelectron spectroscopy, optical absorption spectroscopy, and inverse photoelectron spectroscopy.

[0198] For example, 4,7-diphenyl-1,10-phenanthroline (abbreviated as BPhen), 2,9-di(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviated as NBPhen), diquinoxalino[2,3-a:2',3'-c]phenazine (abbreviated as HATNA), 2,4,6-tris[3'-(pyridine-3-yl)biphenyl-3-yl]-1,3,5-triazine (abbreviated as TmPPPyTz), and 2,2'-(1,3-phenylene)bis(9-phenyl-1,10-phenanthroline) (abbreviated as mPPhen2P) can be used in organic compounds containing lone pairs of electrons. NBPhen has a higher glass transition temperature (Tg) and superior heat resistance compared to BPhen.

[0199] Furthermore, copper phthalocyanine can be used, for example, in organic compounds that possess lone pairs of electrons. Note that copper phthalocyanine has an odd number of electrons.

[0200] [First Metal] For example, if the first organic compound having a lone pair of electrons has an even number of electrons, a composite material of the first metal and the first organic compound, which belong to an odd group in the periodic table, can be used for layer 105.

[0201] For example, manganese (Mn), a metal of Group 7; cobalt (Co), a metal of Group 9; copper (Cu), silver (Ag), and gold (Au), metals of Group 11; and aluminum (Al) and indium (In), metals of Group 13, are all odd-numbered groups in the periodic table. Furthermore, elements of Group 11 have lower melting points compared to elements of Group 7 or 9, making them suitable for vacuum deposition. Ag, in particular, is preferred due to its low melting point. Additionally, using a metal with poor reactivity with water or oxygen as the first metal can improve the moisture resistance of the light-emitting device 550X.

[0202] Furthermore, by using Ag in the electrode 552X and layer 105, the adhesion between layer 105 and electrode 552X can be improved.

[0203] Furthermore, if the number of electrons in the first organic compound, which has a lone pair of electrons, is odd, a composite material of the first metal and the first organic compound, which belong to an even group in the periodic table, can be used for layer 105. For example, iron (Fe), a metal in group 8, belongs to an even group in the periodic table.

[0204] [Electride] For example, a material obtained by adding a high concentration of electrons to a mixed oxide of calcium and aluminum can be used as an electron-injection material.

[0205] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0206] (Embodiment 5) In this embodiment, the configuration of a light-emitting device 550X according to one aspect of the present invention will be described with reference to Figure 2(A).

[0207] Figure 2(A) is a cross-sectional view illustrating the configuration of a light-emitting device according to one embodiment of the present invention.

[0208] <Example configuration of the 550X light-emitting device> In addition, 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. 2(A)). 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.

[0209] 《Configuration Example 1 of Layer 106》 By applying a voltage, the layer 106 has a function of supplying electrons to the anode side and holes to the cathode side. Also, the layer 106 can be referred to as a charge generation layer.

[0210] For example, a material having hole injection properties that can be used for the layer 104 described in Embodiment 3 can be used for the layer 106. Specifically, a composite material can be used for the layer 106.

[0211] [[ID=​​​​​​​​​​​​​​​A film having an electrical resistivity of [Ω·cm] or less can be used for layer 106_1. Preferably, layer 106_1 is 5 × 10 4 [Ω cm] or more 1×10 7 Having an electrical resistivity of [Ω·cm] or less, more preferably 1 × 10⁻⁶ 5 [Ω cm] or more 1×10 7 It has an electrical resistivity of [Ω·cm] or less.

[0214] Example of layer 106_2 configuration For example, the material that can be used for layer 105 described in Embodiment 4 can be used for layer 106_2.

[0215] 《Example of Layer 106 Configuration 3》 A laminated film formed by stacking layers 106_1, 106_2, and 106_3 can be used for layer 106. Layer 106_3 includes a region sandwiched between layers 106_1 and 106_2.

[0216] 《Example of Layer 106_3 Configuration》 For example, an electron-transporting material can be used for layer 106_3. Layer 106_3 can also be called an electron relay layer. Using layer 106_3 allows the layer in contact with the anode side of layer 106_3 to be separated from the layer in contact with the cathode side of layer 106_3. This reduces the interaction between the layer in contact with the anode side of layer 106_3 and the layer in contact with the cathode side of layer 106_3. Electrons can be smoothly supplied to the layer in contact with the anode side of layer 106_3.

[0217] A material having a LUMO level between the LUMO level of an electron-accepting material contained in the layer in contact with the cathode side of layer 106_3 and the LUMO level of a material contained in the layer in contact with the anode side of layer 106_3 can be suitably used.

[0218] For example, a material having a LUMO level in the range of -5.0 eV or higher, preferably -5.0 eV to -3.0 eV, can be used for layer 106_3.

[0219] Specifically, phthalocyanine-based materials can be used in layer 106_3. For example, copper phthalocyanine (abbreviated as CuPc) or a metal complex having a metal-oxygen bond and an aromatic ligand can be used in layer 106_3.

[0220] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0221] (Embodiment 6) In this embodiment, the configuration of a light-emitting device 550X according to one aspect of the present invention will be described with reference to Figure 2(B).

[0222] Figure 2(B) is a cross-sectional view illustrating the configuration of a light-emitting device according to one embodiment of the present invention, which has a configuration different from that shown in Figure 2(A).

[0223] <Example configuration of the 550X light-emitting device> The 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 Figure 2(B)).

[0224] Unit 103X is sandwiched between electrodes 552X and 551X, and layer 106 is sandwiched between electrodes 552X and unit 103X.

[0225] Unit 103X2 is sandwiched between electrode 552X and layer 106. Unit 103X2 also has the function of emitting light ELX2.

[0226] In other words, the light-emitting device 550X has multiple stacked units between electrodes 551X and 552X. The number of stacked units is not limited to two; three or more units can be stacked. A configuration comprising multiple stacked units sandwiched between electrodes 551X and 552X, and a layer 106 sandwiched between these units, is sometimes referred to as a stacked light-emitting device or a tandem light-emitting device.

[0227] This allows for high-brightness light emission while maintaining a low current density. Alternatively, reliability can be improved. Alternatively, the drive voltage can be reduced when comparing at the same brightness. Alternatively, power consumption can be suppressed.

[0228] 《Example Configuration of Unit 103X2 1》 Unit 103X2 comprises layers 111X2, 112_2, and 113_2. Layer 111X2 is sandwiched between layers 112_2 and 113_2.

[0229] The configuration used in unit 103X can also be used in unit 103X2. For example, the same configuration as unit 103X can be used in unit 103X2.

[0230] 《Example Configuration of Unit 103X2 2》 Furthermore, a different configuration from that of unit 103X can be used for unit 103X2. For example, a configuration that emits light with a different hue than the emitted color of unit 103X can be used for unit 103X2.

[0231] Specifically, a unit 103X that emits red and green light and a unit 103X2 that emits blue light can be stacked and used. This makes it possible to provide a light-emitting device that emits light of a desired color. For example, a light-emitting device that emits white light can be provided.

[0232] Example of Layer 106 configuration Layer 106 has the function of supplying electrons to one of unit 103X or unit 103X2 and holes to the other. For example, the layer 106 described in Embodiment 5 can be used.

[0233] <Method for fabricating the 550X light-emitting device> For example, the electrodes 551X, 552X, unit 103X, layer 106, and unit 103X2 can be formed using dry, wet, vapor deposition, droplet ejection, coating, or printing methods. Furthermore, different methods can be used to form each component.

[0234] Specifically, the light-emitting device 550X can be manufactured using vacuum deposition equipment, inkjet equipment, coating equipment such as spin coaters, gravure printing equipment, offset printing equipment, and screen printing equipment.

[0235] For example, electrodes can be formed using a wet method or a sol-gel method with a paste of a metallic material. Furthermore, an indium oxide-zinc oxide film can be formed by sputtering using a target containing 1 wt% to 20 wt% zinc oxide relative to indium oxide. Additionally, an indium oxide (IWZO) film containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5 wt% to 5 wt% tungsten oxide and 0.1 wt% to 1 wt% zinc oxide relative to indium oxide.

[0236] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0237] (Embodiment 7) In this embodiment, the configuration of a display device 700 according to one aspect of the present invention will be described with reference to Figures 3(A) and 3(B).

[0238] Figure 3(A) is a cross-sectional view illustrating the configuration of a display device 700 according to one embodiment of the present invention, and Figure 3(B) is a cross-sectional view illustrating the configuration of a display device 700 according to a different embodiment of the present invention from Figure 3(A).

[0239] In this specification, variables that take integer values ​​of 1 or more may be used as signs. For example, (p), which includes a variable p that takes an integer value of 1 or more, may be used as part of a sign that identifies any of up to p components. Also, for example, (m,n), which includes a variable m and a variable n that take integer values ​​of 1 or more, may be used as part of a sign that identifies any of up to m × n components.

[0240] <Example of display device 700 configuration 1> 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 Figure 3(A)). The light-emitting device 550Y(i,j) is adjacent to the light-emitting device 550X(i,j).

[0241] The display device 700 has a substrate 510 and a functional layer 520. The functional layer 520 includes an insulating film 521, and the light-emitting devices 550X(i,j) and 550Y(i,j) are formed on the insulating film 521. The functional layer 520 is sandwiched between the substrate 510 and the light-emitting devices 550X(i,j).

[0242] 《Example configuration of the 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). Electrode 552X(i,j) overlaps with electrode 551X(i,j), and unit 103X(i,j) is sandwiched between electrodes 552X(i,j) and 551X(i,j). The light-emitting device 550X(i,j) also has layers 104X(i,j) and 105X(i,j), with layer 104X(i,j) sandwiched between unit 103X(i,j) and electrode 551X(i,j), and layer 105X(i,j) sandwiched between electrode 552X(i,j) and unit 103X(i,j). Unit 103X(i,j) comprises layers 111X(i,j), 112X(i,j), and 113X(i,j).

[0243] For example, the light-emitting device 550X described in Embodiments 2 to 6 can be used for the light-emitting device 550X(i,j). Specifically, a configuration that can be used for electrode 551X can be used for electrode 551X(i,j), and a configuration that can be used for electrode 552X can be used for electrode 552X(i,j). Also, a configuration that can be used for unit 103X can be used for unit 103X(i,j). Furthermore, a configuration that can be used for layer 104 can be used for layer 104X(i,j), and a configuration that can be used for layer 105 can be used for layer 105X(i,j). Also, a configuration that can be used for layer 111X can be used for layer 111X(i,j), a configuration that can be used for layer 112 can be used for layer 112X(i,j), and a configuration that can be used for layer 113 can be used for layer 113X(i,j).

[0244] 《Example configuration of the 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). Electrode 552Y(i,j) overlaps with electrode 551Y(i,j), and unit 103Y(i,j) is sandwiched between electrodes 552Y(i,j) and 551Y(i,j). The light-emitting device 550Y(i,j) also has layers 104Y(i,j) and 105Y(i,j), with layer 104Y(i,j) sandwiched between unit 103Y(i,j) and electrode 551Y(i,j), and layer 105Y(i,j) sandwiched between electrode 552Y(i,j) and unit 103Y(i,j).

[0245] Electrode 551Y(i,j) is adjacent to electrode 551X(i,j), and electrode 551Y(i,j) has a gap 551XY(i,j) between it and electrode 551X(i,j).

[0246] Furthermore, some of the components that can be used in the configuration of the light-emitting device 550X(i,j) can be used in the configuration of the light-emitting device 550Y(i,j). For example, some of the conductive film that can be used in electrode 552X(i,j) can be used in electrode 552Y(i,j). Components that can be used in electrode 551X can be used in electrode 551Y(i,j). Also, components that can be used in layer 104 can be used in layer 104Y(i,j), and components that can be used in layer 105 can be used in layer 105Y(i,j). This allows for the commonality of some components. In addition, the manufacturing process can be simplified.

[0247] Furthermore, a configuration that emits light of the same hue as the light-emitting device 550X(i,j) can be used for the light-emitting device 550Y(i,j).

[0248] For example, both the light-emitting device 550X(i,j) and the light-emitting device 550Y(i,j) may emit white light. Furthermore, by placing a colored layer on top of the light-emitting device 550X(i,j), light of a predetermined hue can be extracted from the white light. Alternatively, by placing another colored layer on top of the light-emitting device 550Y(i,j), light of a different predetermined hue can be extracted from the white light.

[0249] Furthermore, 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 can be superimposed on the light-emitting device 550X(i,j) to convert blue light into light of a predetermined hue. Alternatively, another color conversion layer can be superimposed on the light-emitting device 550Y(i,j) to convert blue light into light of another predetermined hue. Blue light can be converted, for example, into green light or red light.

[0250] Furthermore, a configuration that emits light of a different hue than the light-emitting 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 unit 103Y(i,j) can be made different from the hue of the light ELX.

[0251] 《Example configuration 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 layer 111Y(i,j). Here, the differences are described in detail, and the parts that have the same configuration are described in the above explanation.

[0252] 《Example of layer 111Y(i,j) configuration 1》 For example, a luminescent material, or a luminescent material and a host material, can be used for layer 111Y(i,j). Layer 111Y(i,j) can also be referred to as the luminescent layer. It is preferable to place layer 111Y(i,j) in the region where holes and electrons recombine. This allows the energy generated by carrier recombination to be efficiently emitted as light.

[0253] Furthermore, it is preferable to arrange layer 111Y(i,j) away from the metal used for electrodes, etc. This makes it possible to suppress the quenching phenomenon caused by the metal used for electrodes, etc.

[0254] Furthermore, it is preferable to adjust the distance from the reflective electrodes, etc., to layer 111Y(i,j) and position layer 111Y(i,j) at an appropriate location according to the emission wavelength. This allows for amplification by utilizing the interference phenomenon between the light reflected by the electrodes, etc., and the light emitted by layer 111Y(i,j). In addition, it is possible to strengthen light of a predetermined wavelength and narrow the light spectrum. Furthermore, a vivid emission color can be obtained with high intensity. In other words, a microcavity structure can be constructed by positioning layer 111Y(i,j) at an appropriate location between the electrodes, etc.

[0255] For example, fluorescent materials, phosphorescent materials, or TADF materials can be used as luminescent materials. This allows the energy generated by carrier recombination to be released from the luminescent material as photo-ELY (see Figures 3(A) and 3(B)).

[0256] [Fluorescent material] A fluorescent material can be used in layer 111Y(i,j). For example, the fluorescent materials exemplified below can be used in layer 111Y(i,j). However, this is not limited to these examples, and various known fluorescent materials can be used in layer 111Y(i,j).

[0257] Specifically, these include 5,6-bis[4-(10-phenyl-9-antryl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl-9-antryl)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), and N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl] Nyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N,N'-bis[4-(9H-carbazole-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazole-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazole-9-yl)-4'-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviation :2YGAPPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra(tert-butyl)perylene (abbreviation: TBP), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazole-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-carbazole-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-carbazole-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.

[0258] In particular, condensed aromatic diamine compounds, such as pyrenediamine compounds like 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6BnfAPrn-03, are preferred because they exhibit high hole-trapping properties and excellent luminescence efficiency or reliability.

[0259] 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]chrysen-2,7,10,15-tetraamine (abbreviation: DBC1), coumarin 30, 9,10-diphenyl-2-[N-phenyl-N-(9-phenylcarbazole-3-yl)-amino]-anthracene (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-to Riphenyl-1,4-phenylenediamine (abbreviated as 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPABPhA), 9,10-bis(1,1'-biphenyl-2-yl)-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracene-2-amine (abbreviated as 2YGABPhA), N,N,9-triphenylanthracene-9-amine (abbreviated as DPhAPhA), coumarin 545T, N,N'-diphenylquinacridone (abbreviated as DPQd), rubren, 5,12-bis(1,1'-biphenyl-4-yl)-6,11-diphenyltetracene (abbreviated as BPT), etc. can be used.

[0260] Also, 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]quinoridine-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N',N'-tetrakis (4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluorantene-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]k [Noridin-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]quinoridin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTB), 2-(2,6-bis{2-[4-(di You can use methylamino)phenyl]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]quinoridine-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: BisDCJTM), etc.

[0261] [Phosphorescent material] A phosphorescent material can be used in layer 111Y(i,j). For example, the phosphorescent materials exemplified below can be used in layer 111Y(i,j). However, this is not limited to these, and various known phosphorescent materials can be used in layer 111Y(i,j).

[0262] 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 with 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, etc., can be used in layer 111Y(i,j).

[0263] [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-triazole-3-yl-κN2]phenyl-κC}iridium(III) (abbreviation: [Ir(mpptz-dmp)3]), tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Mptz)3]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPrptz-3b)3]), and others.

[0264] 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]), and others.

[0265] 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]phenanthridine]iridium(III) (abbreviation: [Ir(dmpimpt-Me)3]), and others.

[0266] Examples of organometallic iridium complexes using phenylpyridine derivatives having electron-withdrawing groups as ligands include bis[2-(4',6'-difluorophenyl)pyridinate-N,C 2’ Iridium(III) tetrakis(1-pyrazolyl) borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridinate-N,C 2’ Iridium(III) picolinate (abbreviation: Firpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinate-N,C 2’ Iridium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyridinate-N,C 2’ Iridium(III) acetylacetonate (abbreviated as FIracac), etc., can be used.

[0267] These compounds exhibit blue phosphorescence and have emission wavelength peaks between 440 nm and 520 nm.

[0268] [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.

[0269] Examples of organometallic iridium complexes having a pyrazine skeleton include (acetylacetonato)bis(3,5-dimethyl-2-phenylpyradinato)iridium(III) (abbreviation: [Ir(mppr-Me)2(acac)]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyradinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]), and others.

[0270] Examples of organometallic iridium complexes having a pyridine skeleton include tris(2-phenylpyridinato-N,C) 2’ Iridium(III) (abbreviation: [Ir(ppy)3]), bis(2-phenylpyridinate-N,C) 2’Iridium(III) acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), bis(benzo[h]quinolinate)iridium(III) acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), tris(benzo[h]quinolinate)iridium(III) (abbreviation: [Ir(bzq)3]), tris(2-phenylquinolinate-N,C) 2’ Iridium(III) (abbreviation: [Ir(pq)3]), bis(2-phenylquinolinato-N,C) 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(pq)2(acac)]), [2-d3-methyl-8-(2-pyridinyl-κN)benzoflof[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridinyl-κN 2 [Ir(5mppy-d3)2(mbfpypy-d3)], [2-d3-methyl-(2-pyridinyl-κN)benzofl[2,3-b]pyridine-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(ppy)2(mbfpypy-d3)]), etc. can be used.

[0271] Examples of rare earth metal complexes include tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [Tb(acac)3(Phen)]).

[0272] These compounds primarily exhibit green phosphorescence and have emission wavelength peaks between 500 nm and 600 nm. Furthermore, organometallic iridium complexes with a pyrimidine skeleton are remarkably superior in terms of reliability or luminescence efficiency.

[0273] [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](dipvaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)]), bis[4,6-di(naphthalene-1-yl)pyrimidinato](dipvaloylmethanato)iridium(III) (abbreviation: [Ir(d1npm)2(dpm)]), etc.

[0274] Examples of organometallic iridium complexes having a pyrazine skeleton include (acetylacetonato)bis(2,3,5-triphenylpyradinato)iridium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2,3,5-triphenylpyradinato)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(tppr)2(dpm)]), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq)2(acac)]), etc.

[0275] 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.

[0276] Examples of rare earth metal complexes that can be used include tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: [Eu(DBM)3(Phen)]), tris[1-(2-tenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: [Eu(TTA)3(Phen)]), etc.

[0277] Examples of platinum complexes that can be used include 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviated as PtOEP).

[0278] These compounds exhibit red phosphorescence and have an emission peak between 600 nm and 700 nm. Furthermore, organometallic iridium complexes with a pyrazine skeleton produce red emission with a chromaticity suitable for use in display devices.

[0279] [TADF material] TADF material can be used in layer 111Y(i,j). When TADF material is used as a light-emitting material, it is preferable that the S1 level of the host material is higher than the S1 level of the TADF material. Also, it is preferable that the T1 level of the host material is higher than the T1 level of the TADF material.

[0280] For example, the TADF materials exemplified below can be used as luminescent materials. However, the materials are not limited to these, and various known TADF materials can be used.

[0281] Furthermore, TADF materials have a small difference between the S1 and T1 energy levels, allowing for reverse intersystem crossing (upconversion) from a triplet excited state to a singlet excited state with only a small amount of thermal energy. This enables efficient generation of singlet excited states from triplet excited states. In addition, the triplet excitation energy can be converted into luminescence.

[0282] Furthermore, an excited complex (also called an exciplex) that forms an excited state with two types of substances has an extremely small difference between the S1 and T1 levels and functions as a TADF material that can convert triplet excitation energy into singlet excitation energy.

[0283] Furthermore, the phosphorescence spectrum observed at low temperatures (e.g., 77K to 10K) can be used as an indicator of the T1 level. For TADF materials, when a tangent is drawn at the short-wavelength tail of the fluorescence spectrum and the energy at the wavelength of the extrapolation is taken as the S1 level, and when a tangent is drawn at the short-wavelength tail of the phosphorescence spectrum and the energy at the wavelength of the extrapolation is taken as the T1 level, it is preferable that the difference between the S1 level and the T1 level is 0.3 eV or less, and more preferably 0.2 eV or less.

[0284] For example, fullerenes and their derivatives, acridines and their derivatives, eosin derivatives, etc., can be used as TADF materials. In addition, metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd), etc., can be used as TADF materials.

[0285] Specifically, the following can be used: protoporphyrin-tin fluoride complex (SnF2(Proto IX)), mesoporphyrin-tin fluoride complex (SnF2(Meso IX)), hematoporphyrin-tin fluoride complex (SnF2(Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complex (SnF2(Copro III-4Me)), octaethylporphyrin-tin fluoride complex (SnF2(OEP)), etioporphyrin-tin fluoride complex (SnF2(Etio I)), octaethylporphyrin-platinum chloride complex (PtCl2OEP), etc., whose structural formulas are shown below.

[0286] [ka]

[0287] Furthermore, for example, heterocyclic compounds having one or both of a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring can be used as TADF materials.

[0288] Specifically, the structural formulas are as follows: 2-(biphenyl-4-yl)-4,6-bis(12-phenylindoro[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'-bicarbazol (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-phenoxazine-10-yl)phenyl]-4 ,6-diphenyl-1,3,5-triazine (abbreviated as PXZ-TRZ), 3-[4-(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (abbreviated as PPZ-3TPT), 3-(9,9-dimethyl-9H-acridine-10-yl)-9H-xanthene-9-one (abbreviated as ACRXTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviated as DMAC-DPS), 10-phenyl-10H,10'H-spiro[acridine-9,9'-anthracene]-10'-one (abbreviated as ACRSA), etc. can be used.

[0289] [ka]

[0290] The heterocyclic compound is preferred because it has both a π-electron-excess heteroaromatic ring and a π-electron-deficient heteroaromatic ring, resulting in high electron transport and hole transport properties. In particular, among the skeletons having a π-electron-deficient heteroaromatic ring, the pyridine skeleton, diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton), and triazine skeleton are preferred because they are stable and reliable. In particular, the benzoflopyrimidine skeleton, benzothienopyrimidine skeleton, benzoflopyrazine skeleton, and benzothienopyrazine skeleton are preferred because they have high electron-accepting properties and are reliable.

[0291] Furthermore, among skeletons having a π-electron-excess heteroaromatic ring, the acridine skeleton, phenoxazine skeleton, phenothiazine skeleton, furan skeleton, thiophene skeleton, and pyrrole skeleton are stable and reliable, and therefore it is preferable to have at least one of these skeletons. Dibenzofuran is preferred as the furan skeleton, and dibenzothiophene is preferred as the thiophene skeleton. Indole, carbazole, indrocarbazole, bicarbazole, and 3-(9-phenyl-9H-carbazole-3-yl)-9H-carbazole are particularly preferred as the pyrrole skeleton.

[0292] Furthermore, materials in which a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring are directly bonded are particularly preferred because both the electron-donating ability of the π-electron-rich heteroaromatic ring and the electron-accepting ability of the π-electron-deficient heteroaromatic ring are strengthened, and the energy difference between the S1 and T1 levels is reduced, thus efficiently obtaining thermally activated delayed fluorescence. Alternatively, 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. Additionally, aromatic amine skeletons, phenazine skeletons, and the like can be used as the π-electron-rich skeleton.

[0293] Furthermore, as π-electron-deficient skeletons, xanthene skeletons, thioxanthene dioxide skeletons, oxadiazole skeletons, triazole skeletons, imidazole skeletons, anthraquinone skeletons, boron-containing skeletons such as phenylborane or volanthrene, aromatic rings or heteroaromatic rings having a nitrile group or cyano group such as benzonitrile or cyanobenzene, carbonyl skeletons such as benzophenone, phosphine oxide skeletons, sulfone skeletons, and the like can be used.

[0294] Thus, a π-electron-deficient skeleton and a π-electron-excess skeleton can be used instead of at least one of a π-electron-deficient heteroaromatic ring and a π-electron-excess heteroaromatic ring.

[0295] 《Example of layer 111Y(i,j) configuration 2》 Materials with carrier transport properties can be used as the host material. For example, materials with hole transport properties, materials with electron transport properties, TADF materials, materials with anthracene skeletons, and mixed materials can be used as the host material. It is preferable to use a material with a larger band gap than the luminescent material contained in layer 111Y(i,j) as the host material. This makes it possible to suppress energy transfer from excitons generated in layer 111Y(i,j) to the host material.

[0296] [Materials with hole transport properties] The hole mobility is 1 × 10⁻⁶. -6 cm 2 Materials with a Vs of 1 / Vs or higher can be suitably used as hole-transporting materials. For example, a hole-transporting material that can be used in layer 112 can be used as a host material.

[0297] [Materials with electron transport properties] Metal complexes or organic compounds having a π-electron-deficient heteroaromatic ring skeleton can be used as electron-transporting materials. For example, an electron-transporting material that can be used in layer 113 can be used as a host material.

[0298] [Materials containing an anthracene skeleton] Organic compounds having an anthracene skeleton can be used as host materials. In particular, organic compounds having an anthracene skeleton are suitable when fluorescent materials are used as the light-emitting material. This makes it possible to realize light-emitting devices with good luminescence efficiency and durability.

[0299] Among organic compounds having an anthracene skeleton, organic compounds having a diphenylanthracene skeleton, particularly a 9,10-diphenylanthracene skeleton, are preferred because they are chemically stable. Furthermore, when the host material has a carbazole skeleton, it is preferred because the hole injection and transport properties are enhanced. In particular, when the host material contains a dibenzocarbazole skeleton, the HOMO level becomes about 0.1 eV shallower than that of carbazole, making it easier for holes to enter, and it is also preferred because it 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 a carbazole skeleton.

[0300] Therefore, substances having both a 9,10-diphenylanthracene skeleton and a carbazole skeleton, substances having both a 9,10-diphenylanthracene skeleton and a benzocarbazole skeleton, and substances having both a 9,10-diphenylanthracene skeleton and a dibenzocarbazole skeleton are preferred as host materials.

[0301] 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 [Lu-9-anthryl)phenyl]-9H-carbazole (abbreviated as PCzPA), 9-[4-(10-phenyl-9-antracenyl)phenyl]-9H-carbazole (abbreviated as CzPA), 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated as cgDBCzPA), 3-[4-(1-naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviated as PCPN), etc. can be used.

[0302] In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA exhibit very good characteristics.

[0303] [TADF material] TADF materials can be used as host materials. When TADF materials are used as host materials, the triplet excitation energy generated by the TADF material can be converted into singlet excitation energy through reverse intersystem crossing. Furthermore, the excitation energy can be transferred to the 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 increase the luminescence efficiency of the light-emitting device.

[0304] This is particularly effective when the light-emitting material is a fluorescent material. Furthermore, in order to obtain high luminescence efficiency, it is preferable that the S1 level of the TADF material is higher than that of the fluorescent material. Also, it is preferable that the T1 level of the TADF material is higher than that of the fluorescent material. Therefore, it is preferable that the T1 level of the TADF material is higher than that of the fluorescent material.

[0305] Furthermore, it is preferable to use a TADF material that exhibits emission that overlaps with the wavelength of the lowest-energy absorption band of the fluorescent material. This is preferable because it allows for smooth transfer of excitation energy from the TADF material to the fluorescent material, resulting in efficient emission.

[0306] Furthermore, for singlet excitation energy to be efficiently generated from triplet excitation energy by 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 substance. To achieve this, it is preferable that the fluorescent substance has protecting groups around the luminescent phosphoform (the skeleton that causes luminescence). Preferred protecting groups are substituents without π bonds, and saturated hydrocarbons are preferred. Specifically, 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 to have multiple protecting groups. Substituents without π bonds have poor carrier transport function, and therefore can increase the distance between the TADF material and the luminescent phosphoform of the fluorescent substance with little effect on carrier transport or carrier recombination.

[0307] Here, the term "luminescent phosphat" refers to the group of atoms (skeleton) that causes light emission in a fluorescent material. The luminescent phosphat preferably has a skeleton with π bonds, preferably contains an aromatic ring, and preferably has a fused aromatic ring or a fused heteroaromatic ring.

[0308] Examples of condensed aromatic rings or condensed heteroaromatic rings include phenanthrene skeletons, stilbene skeletons, acridone skeletons, phenoxazine skeletons, and phenothiazine skeletons. In particular, fluorescent materials having naphthalene skeletons, anthracene skeletons, fluorene skeletons, chrysene skeletons, triphenylene skeletons, tetracene skeletons, pyrene skeletons, perylene skeletons, coumarin skeletons, quinacridone skeletons, and naphthobisbenzofuran skeletons are preferred because they have high fluorescence quantum yields.

[0309] For example, TADF material, which can be used as a luminescent material, can be used as a host material.

[0310] [Example of mixed material composition 1] Furthermore, a material composed of a mixture of multiple substances can be used as the host material. For example, a material with electron-transporting properties and a material with hole-transporting properties can be used in the mixture. The weight ratio of the material with hole-transporting properties to the material with electron-transporting properties in the mixture should be (material with hole-transporting properties / material with electron-transporting properties) = (1 / 19) or more and (19 / 1) or less. This allows for easy adjustment of the carrier transport properties of layer 111Y(i,j). In addition, the recombination region can be easily controlled.

[0311] [Example of mixed material composition 2] Materials mixed with phosphorescent materials can be used as host materials. When using fluorescent materials as the light-emitting material, the phosphorescent material can be used as an energy donor to supply excitation energy to the fluorescent material.

[0312] [Example of mixed material composition 3] A mixed material containing a material that forms an excited complex can be used as the host material. For example, a material in which the emission spectrum of the formed excited complex overlaps with the wavelength of the lowest energy absorption band of the luminescent material can be used as the host material. This allows for smoother energy transfer and improves luminescence efficiency. Alternatively, the driving voltage can be suppressed. With such a configuration, luminescence using ExTET (Exciplex-Triplet Energy Transfer), which is energy transfer from the excited complex to the luminescent material (phosphorescent material), can be efficiently obtained.

[0313] A phosphorescent material can be used in at least one of the materials forming the excitation complex. This allows for the utilization of reverse intersystem crossing. Alternatively, the triplet excitation energy can be efficiently converted to the singlet excitation energy.

[0314] For a combination of materials to form an excited complex, it is preferable that the HOMO level of the hole-transporting material is higher than or equal to the HOMO level of the electron-transporting material. Alternatively, it is preferable that the LUMO level of the hole-transporting material is higher than or equal to the LUMO level of the electron-transporting material. This allows for efficient formation of the excited complex. The LUMO and HOMO levels of the materials can be derived from their electrochemical properties (reduction potential and oxidation potential). Specifically, the reduction potential and oxidation potential can be measured using cyclic voltammetry (CV) measurement.

[0315] The formation of excited complexes can be confirmed, for example, by comparing the emission spectra of a hole-transporting material, an electron-transporting material, and a mixed film made by mixing these materials, and observing that the emission spectrum of the mixed film shifts to a longer wavelength than the emission spectra of each individual material (or has a new peak on the longer wavelength side). Alternatively, it can be confirmed by comparing the transient photoluminescence (PL) of a hole-transporting material, the transient PL of an electron-transporting material, and the transient PL of a mixed film made by mixing these materials, and observing differences in the transient response, such as the transient PL lifetime of the mixed film having a longer lifetime component or a larger proportion of the delayed component than the transient PL lifetime of each individual material. Furthermore, the transient PL mentioned above can be replaced with transient electroluminescence (EL). That is, the formation of excited complexes can also be confirmed by comparing the transient EL of a hole-transporting material, the transient EL of an electron-transporting material, and the transient EL of a mixed film made by mixing these materials, and observing the differences in the transient response.

[0316] <Example configuration of display device 700 2> Furthermore, the display device 700 described in this embodiment has an insulating film 528 (see Figure 3(A)).

[0317] 《Example of the configuration of insulating film 528》 The insulating film 528 has openings, one of which overlaps with electrode 551X(i,j), and the other opening overlaps with electrode 551Y(i,j). The insulating film 528 also overlaps with the gap 551XY(i,j).

[0318] 《Example of the configuration of gap 551XY(i,j)》 The gap 551XY(i,j) sandwiched between electrodes 551X(i,j) and 551Y(i,j) has, for example, a groove-like shape. This creates a step along the groove. In addition, a discontinuity or a thin film portion is formed between the film deposited on the gap 551XY(i,j) and the film deposited on electrode 551X(i,j).

[0319] For example, when an anisotropic film deposition method such as thermal deposition is used, discontinuities or thin film portions are formed along the above-mentioned step in region 104XY(i,j) sandwiched between layers 104X(i,j) and 104Y(i,j).

[0320] This allows for the suppression of current flowing through region 104XY(i,j), for example. It also allows for the suppression of current flowing between layers 104X(i,j) and 104Y(i,j). Furthermore, it suppresses the phenomenon where an adjacent light-emitting device 550Y(i,j) unintentionally emits light in conjunction with the operation of light-emitting device 550X(i,j).

[0321] <Example configuration of display device 700 3> 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 Figure 3(B)). The light-emitting device 550Y(i,j) is adjacent to the light-emitting device 550X(i,j).

[0322] Note that the display device 700 described using Figure 3(B) differs from the display device 700 described using Figure 3(A) in that, in the portion overlapping with the gap 551XY(i,j), part or all of the configuration of the light-emitting device 550X(i,j) or light-emitting device 550Y(i,j) is removed, and the insulating film 528 is replaced with films 529_1, 529_2, and 529_3. Here, the differing parts will be described in detail, and the above description will be used as a reference for parts that have the same configuration.

[0323] 《Example of membrane 529_1 configuration》 The film 529_1 has openings, one of which overlaps with electrode 551X(i,j) and the other overlaps with electrode 551Y(i,j) (see Figure 3(B)). The film 529_1 also has openings that overlap with the gap 551XY(i,j). For example, films containing metal, metal oxides, organic materials, or inorganic insulating materials can be used for film 529_1. Specifically, a light-shielding metal film can be used. This protects the light-emitting device from light irradiated during the manufacturing process.

[0324] 《Example of membrane 529_2 configuration》 The membrane 529_2 has openings, one of which overlaps with electrode 551X(i,j) and the other opening overlaps with electrode 551Y(i,j). The membrane 529_2 also overlaps with the gap 551XY(i,j).

[0325] The film 529_2 includes regions that are in contact with layer 104X(i,j) and unit 103X(i,j).

[0326] Furthermore, the film 529_2 includes regions that are in contact with layer 104Y(i,j) and unit 103Y(i,j).

[0327] Furthermore, film 529_2 includes a region in contact with the insulating film 521. For example, film 529_2 can be formed using atomic layer deposition (ALD) method. This allows for the formation of a film with good coverage. Specifically, metal oxide films and the like can be used for film 529_2. For example, aluminum oxide can be used.

[0328] 《Example of membrane 529_3 configuration》 The film 529_3 has openings, one of which overlaps with electrode 551X(i,j) and the other overlaps with electrode 551Y(i,j). Furthermore, the film 529_3 fills the 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, acrylic resin can be used.

[0329] This allows for electrical insulation between layers 104X(i,j) and 104Y(i,j), for example. It also suppresses the current flowing through region 104XY(i,j). Furthermore, it suppresses the phenomenon where an adjacent light-emitting device 550Y(i,j) unintentionally emits light in conjunction with the operation of light-emitting device 550X(i,j). It also reduces the size of the step between the upper surface of unit 103X(i,j) and the upper surface of unit 103Y(i,j). Additionally, it suppresses the phenomenon of discontinuity or thin film formation between electrodes 552X(i,j) and 552Y(i,j) due to the step. Moreover, a single conductive film can be used for electrodes 552X(i,j) and 552Y(i,j).

[0330] For example, using photolithography, some or all of the components that can be used in the light-emitting device 550X(i,j) or light-emitting device 550Y(i,j) can be removed from the portion that overlaps with the gap 551XY(i,j). In this specification, devices fabricated using a metal mask or FMM (Fine Metal Mask, high-resolution metal mask) may be referred to as MM (metal mask) structured devices. Also, in this specification, devices fabricated without using a metal mask or FMM may be referred to as MML (metal maskless) structured devices.

[0331] Specifically, in the first step, a membrane that will later become unit 103Y(i,j) is formed on the gap 551XY(i,j).

[0332] In the second step, a first film, which will later become film 529_1, is formed on the film that will later become unit 103Y(i,j).

[0333] In the third step, an opening overlapping the gap 551XY(i,j) is formed in the first membrane using photolithography.

[0334] 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 with the gap 551XY(i,j). For example, the unit 103Y(i,j) is removed using a dry etching method. Specifically, organic compounds can be removed using an oxygen-containing gas. This forms a groove in the region overlapping with the gap 551XY(i,j).

[0335] In the fifth step, for example, a second membrane, which will later become membrane 529_2, is formed on the first membrane using the ALD method.

[0336] In the sixth step, for example, a photosensitive polymer is used to form a film 529_3. This fills the groove formed in the region overlapping with the gap 551XY(i,j).

[0337] In the seventh step, using photolithography, openings overlapping with the electrode 551Y(i,j) are formed in the first and second films, thereby forming films 529_1 and 529_2.

[0338] In the eighth step, a layer 105Y(i,j) is formed on the unit 103Y(i,j), and an electrode 552Y(i,j) is formed on the layer 105Y(i,j).

[0339] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0340] (Embodiment 8) In this embodiment, the configuration of a display device 700 according to one aspect of the present invention will be described with reference to Figures 4(A) and 4(B).

[0341] Figure 4(A) is a cross-sectional view illustrating the configuration of a display device 700 according to one embodiment of the present invention, and Figure 4(B) is a cross-sectional view illustrating the configuration of a display device 700 according to a different embodiment of the present invention from Figure 4(A).

[0342] <Example of display device 700 configuration 1> 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 Figure 4(A)). The photoelectric conversion device 550S(i,j) is adjacent to the light-emitting device 550X(i,j).

[0343] 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 photoelectric conversion device 550S(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).

[0344] 《Example configuration of the 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). Electrode 552X(i,j) overlaps with electrode 551X(i,j), and unit 103X(i,j) is sandwiched between electrodes 552X(i,j) and 551X(i,j). The light-emitting device 550X(i,j) also has layers 104X(i,j) and 105X(i,j), with layer 104X(i,j) sandwiched between unit 103X(i,j) and electrode 551X(i,j), and layer 105X(i,j) sandwiched between electrode 552X(i,j) and unit 103X(i,j).

[0345] For example, the light-emitting device 550X described in Embodiments 2 to 6 can be used for the light-emitting device 550X(i,j). Specifically, a configuration that can be used for electrode 551X can be used for electrode 551X(i,j), and a configuration that can be used for electrode 552X can be used for electrode 552X(i,j). Also, a configuration that can be used for unit 103X can be used for unit 103X(i,j). Furthermore, a configuration that can be used for layer 104 can be used for layer 104X(i,j), and a configuration that can be used for layer 105 can be used for layer 105X(i,j).

[0346] 《Example configuration 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). Electrode 552S(i,j) overlaps with electrode 551S(i,j), and unit 103S(i,j) is sandwiched between electrodes 552S(i,j) and 551S(i,j). The photoelectric conversion device 550S(i,j) also has layers 104S(i,j) and 105S(i,j), with layer 104S(i,j) sandwiched between unit 103S(i,j) and electrode 551S(i,j), and layer 105S(i,j) sandwiched between electrode 552S(i,j) and unit 103S(i,j).

[0347] Electrode 551S(i,j) is adjacent to electrode 551X(i,j), and electrode 551S(i,j) has a gap 551XS(i,j) between it and electrode 551X(i,j).

[0348] Furthermore, some of the components that can be used in the configuration of the light-emitting device 550X(i,j) described in Embodiments 2 to 6 can be used in the configuration of the photoelectric conversion device 550S(i,j). For example, some of the conductive film that can be used for electrode 552X(i,j) can be used for electrode 552S(i,j), and components that can be used for electrode 551X can be used for electrode 551S(i,j). Also, components that can be used for layer 104 can be used for layer 104S(i,j), and components that can be used for layer 105 can be used for layer 105S(i,j). This allows for the commonality of some components. In addition, the manufacturing process can be simplified.

[0349] Note that the photoelectric conversion device 550S(i,j) differs from the light-emitting device 550X(i,j) in that it has a unit 103S(i,j) that converts light into electric current, instead of a unit 103X(i,j) that emits light. Here, the differences will be explained in detail, and the parts that have the same configuration will be explained by referring to the explanation above.

[0350] 《Example configuration of Unit 103S(i,j)》 Unit 103S(i,j) has a single-layer structure or a multi-layer structure. For example, in addition to the photoelectric conversion layer, layers selected from functional layers such as hole transport layers, electron transport layers, and carrier block layers can be used in Unit 103S(i,j).

[0351] Unit 103S(i,j) comprises layers 114S(i,j), 112S(i,j), and 113S(i,j) (see Figure 4(A)). Layer 114S(i,j) is sandwiched between layers 112S(i,j) and 113S(i,j). 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).

[0352] Furthermore, unit 103S(i,j) has the function of absorbing light hv and supplying electrons to one electrode and holes to the other electrode. For example, unit 103S(i,j) supplies holes to electrode 551S(i,j) and electrons to electrode 552S(i,j).

[0353] Furthermore, some of the components that can be used in the configuration of unit 103X described in Embodiment 2 can be used in the configuration of unit 103S(i,j). For example, components that can be used in layer 112 can be used in layer 112S(i,j), and components that can be used in layer 113 can be used in layer 113S(i,j). This allows for the commonality of some components. In addition, the manufacturing process can be simplified.

[0354] 《Example of layer 114S(i,j) configuration 1》 Layer 114S(i,j) can be called the photoelectric conversion layer. Layer 114S(i,j) absorbs light hv and supplies electrons to the layer adjacent to it and holes to the layer adjacent to it. For example, layer 114S(i,j) supplies holes to layer 112S(i,j) and electrons to layer 113S(i,j). For example, materials that can be used in organic solar cells can be used in layer 114S(i,j). Specifically, electron-accepting materials and electron-donating materials can be used in layer 114S(i,j).

[0355] [Examples of electron-accepting materials] For example, fullerene derivatives, non-fullerene electron acceptors, etc., can be used as electron-accepting materials.

[0356] Examples of electron-accepting materials include C 60 Fullerene, C 70 Fullerene, [6,6]-phenyl-C 71 -Methyl butyrate (abbreviation: PC71BM), [6,6]-phenyl-C 61 -Methyl butyrate (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.

[0357] Furthermore, non-fullerene electron acceptors can include, for example, perylene derivatives, compounds having a dicyanomethyleneindanone group, etc. N,N'-dimethyl-3,4,9,10-perylenetetracarboxylic acid diimide (abbreviated as Me-PTCDI), etc.

[0358] [Examples of electron-donating materials] For example, phthalocyanine compounds, tetracene derivatives, quinacridone derivatives, rubrene derivatives, etc., can be used as electron-donating materials.

[0359] Examples of electron-donating materials include copper(II) phthalocyanine (abbreviated as CuPc), tin(II) phthalocyanine (abbreviated as SnPc), zinc phthalocyanine (abbreviated as ZnPc), tetraphenyldibenzoperifuranthene (abbreviated as DBP), rubrene, and others.

[0360] 《Example of layer 114S(i,j) configuration 2》 For example, a single-layer structure or a multi-layer structure can be used for layer 114S(i,j). Specifically, a bulk heterojunction type structure can be used for layer 114S(i,j). Alternatively, a heterojunction type structure can be used for layer 114S(i,j).

[0361] [Example of mixed material composition] For example, a mixed material containing electron-accepting and electron-donating materials can be used in layer 114S(i,j) (see Figure 4(A)). A configuration in which a mixed material containing electron-accepting and electron-donating materials is used in layer 114S(i,j) can be called a bulk heterojunction type.

[0362] Specifically, C 70 A mixed material containing fullerene and DBP can be used in layer 114S(i,j).

[0363] [Example of heterozygous type] Layers 114N(i,j) and 114P(i,j) can be used as layer 114S(i,j) (see Figure 4(B)). 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).

[0364] n-type semiconductors can be used in layer 114N(i,j). For example, Me-PTCDI can be used in layer 114N(i,j).

[0365] Furthermore, a p-type semiconductor can be used in layer 114P(i,j). For example, rubrene can be used in layer 114P(i,j).

[0366] Furthermore, a photoelectric conversion device 550S(i,j) having a configuration in which layer 114P(i,j) is in contact with layer 114N(i,j) can be called a PN junction type photodiode.

[0367] (Embodiment 9) In this embodiment, the configuration of an apparatus according to one aspect of the present invention will be described with reference to Figures 5 to 7.

[0368] Figure 5 is a diagram illustrating the configuration of an apparatus according to one embodiment of the present invention. Figure 5(A) is a top view of an apparatus according to one embodiment of the present invention, and Figure 5(B) is a top view illustrating a part of Figure 5(A). Figure 5(C) is a cross-sectional view of the cutting lines X1-X2, X3-X4 and a pair of pixels 703(i,j) shown in Figure 5(A).

[0369] Figure 6 is a circuit diagram illustrating the configuration of an apparatus according to one embodiment of the present invention.

[0370] Figure 7 is a diagram illustrating the configuration of an apparatus according to one embodiment of the present invention. Figure 7(A) is a cross-sectional view of the apparatus according to one embodiment of the present invention, and Figure 7(B) is a different cross-sectional view from Figure 7(A).

[0371] <Example of display device 700 configuration 1> A display device 700 according to one aspect of the present invention has a region 231 (see Figure 5(A)). Region 231 comprises a pair of pixels 703(i,j).

[0372] 《Example of a set of 703 pixels (i,j)》 A pair of pixels 703(i,j) comprises pixels 702X(i,j) (see Figures 5(B) and 5(C)).

[0373] Pixel 702X(i,j) comprises 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).

[0374] For example, the light-emitting device described in Embodiments 2 to 6 can be used as the light-emitting device 550X(i,j). The display device 700 has a function for displaying images.

[0375] <Example configuration of display device 700 2> Furthermore, a display device 700 according to one aspect of the present invention has a functional layer 540 and a functional layer 520 (see Figure 5(C)). The functional layer 540 overlaps with the functional layer 520.

[0376] The functional layer 540 includes a light-emitting device 550X(i,j).

[0377] The functional layer 520 includes pixel circuits 530X(i,j) and wiring (see Figure 5(C)). The pixel circuits 530X(i,j) are electrically connected to the wiring. For example, a conductive film provided in the aperture 591X or aperture 591Y of the functional layer 520 can be used for the wiring. The wiring electrically connects terminal 519B and the pixel circuits 530X(i,j). The conductive material CP electrically connects terminal 519B and the flexible printed circuit board FPC1.

[0378] <Example configuration of display device 700 3> Furthermore, a display device 700 according to one embodiment of the present invention has a drive circuit GD and a drive circuit SD (see Figure 5(A)).

[0379] Example configuration of the drive circuit GD The drive circuit GD supplies a first selection signal and a second selection signal.

[0380] 《Example configuration of the SD drive circuit》 The drive circuit SD supplies a first control signal and a second control signal.

[0381] 《Wiring Configuration Example 1》 The wiring includes conductive films G1(i), G2(i), S1(j), S2(j), ANO, VCOM2, and V0 (see Figure 6).

[0382] Conductive film G1(i) is supplied with a first selection signal, and conductive film G2(i) is supplied with a second selection signal.

[0383] Conductive film S1(j) is supplied with a first control signal, and conductive film S2(j) is supplied with a second control signal.

[0384] 《Example Configuration 1 of Pixel Circuit 530X(i,j)》 The pixel circuit 530X(i,j) is electrically connected to conductive film G1(i) and conductive film S1(j). Conductive film G1(i) supplies a first selection signal, and conductive film S1(j) supplies a first control signal.

[0385] The pixel circuit 530X(i,j) drives the light-emitting device 550X(i,j) based on a first selection signal and a first control signal. The light-emitting device 550X(i,j) also emits light.

[0386] 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.

[0387] 《Example Configuration 2 of Pixel Circuit 530X(i,j)》 The pixel circuit 530X(i,j) includes switch SW21, switch SW22, transistor M21, capacitor C21, and node N21.

[0388] Transistor M21 comprises a gate electrode electrically connected to node N21, a first electrode electrically connected to light-emitting device 550X(i,j), and a second electrode electrically connected to conductive film ANO.

[0389] The switch SW21 comprises a first terminal electrically connected to node N21, a second terminal electrically connected to conductive film S1(j), and a gate electrode that has the function of controlling a conduction state or a non-conduction state based on the potential of conductive film G1(i).

[0390] The switch SW22 comprises a first terminal electrically connected to the conductive film S2(j), and a gate electrode that has the function of controlling a conduction state or a non-conduction state based on the potential of the conductive film G2(i).

[0391] Capacitor C21 comprises a conductive film electrically connected to node N21 and a conductive film electrically connected to the second electrode of switch SW22.

[0392] This allows the image signal to be stored in node N21. Alternatively, the potential of node N21 can be changed using switch SW22. Or, the intensity of the light emitted by the light-emitting device 550X(i,j) can be controlled using the potential of node N21. As a result, a novel device with superior convenience, usefulness, and reliability can be provided.

[0393] 《Example 3 of the Pixel Circuit 530X(i,j) Configuration》 The pixel circuit 530X(i,j) includes a switch SW23, a node N22, and a capacitor C22.

[0394] The switch SW23 comprises a first terminal electrically connected to the conductive film V0, a ​​second terminal electrically connected to node N22, and a gate electrode that has the function of controlling a conduction state or a non-conduction state based on the potential of the conductive film G2(i).

[0395] Capacitor C22 comprises a conductive film electrically connected to node N21 and a conductive film electrically connected to node N22.

[0396] The first electrode of transistor M21 is electrically connected to node N22.

[0397] 《Example Configuration 1 of Pixel 702X(i,j)》 Pixel 702X(i,j) comprises a light-emitting device 550X(i,j) and a pixel circuit 530X(i,j) (see Figure 7(A)). Functional layer 540 includes a light-emitting device 550X(i,j) and a color layer CFX, and functional layer 520 includes a pixel circuit 530X(i,j).

[0398] The light-emitting device 550X(i,j) is a top-emission type light-emitting device, and the light-emitting device 550X(i,j) emits optical ELX to the side where the functional layer 520 is not located.

[0399] The colored 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 to extract blue, green, or red light. Alternatively, a color conversion layer can be used instead of the colored layer CFX. This allows for the conversion of short-wavelength light to long-wavelength light.

[0400] 《Example configuration of pixel 702X(i,j) 2》 The pixel 702X(i,j), as explained using Figure 7(B), is equipped with a bottom-emission type light-emitting device. The light-emitting device 550X(i,j) emits optical ELX towards the side where the functional layer 520 is located.

[0401] The functional layer 520 includes region 520T, which transmits optical ELX. Additionally, the functional layer 520 includes a colored layer CFX, which overlaps with region 520T.

[0402] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0403] (Embodiment 10) This embodiment describes a light-emitting device using a light-emitting device described in any one of Embodiments 2 to 6.

[0404] 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 Figure 8. Figure 8(A) is a top view showing the light-emitting device, and Figure 8(B) is a cross-sectional view obtained by cutting Figure 8(A) along A and C and D. This light-emitting device has a pixel section 602 and a drive circuit section to control the light emission of the light-emitting device, and the drive circuit section includes a source line drive circuit 601 and a gate line drive circuit 603. The light-emitting device also includes a sealing substrate 604 and a sealing material 605, and the sealing material 605 surrounds a space 607.

[0405] The routing wiring 608 is for transmitting signals input to the source line drive circuit 601 and the gate line drive circuit 603, and receives video signals, clock signals, start signals, reset signals, etc. from the FPC (flexible printed circuit) which serves as the external input terminal 609. Although only the FPC is shown in the diagram, a printed circuit 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 the state in which the FPC or PWB is attached to it.

[0406] Next, the cross-sectional structure will be explained using Figure 8(B). A drive circuit section and a pixel section are formed on the element substrate 610, and here, the source line drive circuit 601, which is the drive circuit section, and one pixel in the pixel section 602 are shown.

[0407] The element substrate 610 may be manufactured using a substrate made of glass, quartz, organic resin, metal, alloy, semiconductor, or other materials, as well as a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (Polyvinyl Fluoride), polyester, or acrylic resin.

[0408] The structure of the transistor used in the pixel or driving circuit is not particularly limited. For example, it may be an inverse staggered transistor or a staggered transistor. It may also be a top-gate or bottom-gate transistor. The semiconductor material used for the transistor is not particularly limited; for example, silicon, germanium, silicon carbide, gallium nitride, etc., can be used. Alternatively, an oxide semiconductor containing at least one of indium, gallium, and zinc, such as an In-Ga-Zn metal oxide, may be used.

[0409] The crystallinity of the semiconductor material used in the transistor is not particularly limited; amorphous semiconductors, crystalline semiconductors (microcrystalline semiconductors, polycrystalline semiconductors, single-crystal semiconductors, or semiconductors having a crystalline region in part) may be used. Using a crystalline semiconductor is preferable because it can suppress the degradation of transistor characteristics.

[0410] Here, it is preferable to use oxide semiconductors for semiconductor devices such as transistors used in the pixels or driving circuits described above, as well as transistors used in touch sensors and the like, which will be described later. In particular, it is preferable to use oxide semiconductors with a wider bandgap than silicon. By using oxide semiconductors with a wider bandgap than silicon, the current in the off state of the transistor can be reduced.

[0411] The above oxide semiconductor preferably contains at least indium (In) or zinc (Zn). More preferably, it is an oxide semiconductor containing an oxide represented as an In-M-Zn oxide (where M is a metal such as Al, Ti, Ga, Ge, Y, Zr, Sn, La, Ce, or Hf).

[0412] In particular, it is preferable to use an oxide semiconductor film as the semiconductor layer, which has multiple crystalline portions, the c-axis of which is oriented perpendicular to the surface on which the semiconductor layer is formed or to the upper surface of the semiconductor layer, and which does not have grain boundaries between adjacent crystalline portions.

[0413] By using such materials as semiconductor layers, fluctuations in electrical properties can be suppressed, enabling the realization of highly reliable transistors.

[0414] Furthermore, due to its low off-current, the transistor having the aforementioned semiconductor layer can retain the charge stored in the capacitor via the transistor for a long period of time. By applying such transistors to pixels, it becomes possible to maintain the gradation of the image displayed in each display area while simultaneously stopping the drive circuit. As a result, electronic devices with extremely reduced power consumption can be realized.

[0415] It is preferable to provide an undercoat to stabilize the characteristics of the transistor. As the undercoat, an inorganic insulating film such as a silicon oxide film, silicon nitride film, silicon oxynitride film, or silicon nitride film can be used and fabricated as a single layer or in a multilayer configuration. The undercoat can be formed using sputtering, CVD (Chemical Vapor Deposition) (plasma CVD, thermal CVD, MOCVD (Metal Organic CVD), etc.), ALD, coating, printing, etc. However, the undercoat may be omitted if it is not necessary.

[0416] Note that FET623 is one of the transistors formed in the source line drive circuit 601. The drive circuit can be formed using various CMOS, PMOS, or NMOS circuits. In this embodiment, a driver-integrated type with the drive circuit formed on the substrate is shown, but this is not necessarily required, and the drive circuit can be formed externally instead of on the substrate.

[0417] Furthermore, although the pixel section 602 is formed by a plurality of pixels including a switching FET 611 and a current control FET 612 and a first electrode 613 electrically connected to its drain, it is not limited to this, and the pixel section may be a combination of three or more FETs and a capacitive element.

[0418] Furthermore, an insulator 614 is formed to cover the end of the first electrode 613. This can be formed by using a positive-type photosensitive acrylic resin film.

[0419] Furthermore, in order to ensure good coverage of the EL layer and the like that will be formed later, a curved surface with curvature is formed at the upper or lower end of the insulator 614. For example, when a positive-type photosensitive acrylic resin is used as the material for the insulator 614, it is preferable to have a curved surface with a radius of curvature (0.2 μm or more and 3 μm or less) only at the upper end of the insulator 614. In addition, either a negative-type photosensitive resin or a positive-type photosensitive resin can be used as the insulator 614.

[0420] An EL layer 616 and a second electrode 617 are formed on the first electrode 613, respectively. Here, it is desirable to use a material with a large work function for the first electrode 613 which functions as an anode. For example, in addition to single-layer films such as ITO film, silicon-containing indium tin oxide film, indium oxide film containing 2 wt% to 20 wt% zinc oxide, titanium nitride film, chromium film, tungsten film, Zn film, and Pt film, a laminate of titanium nitride film and a film mainly composed of aluminum, or a three-layer structure of titanium nitride film, a film mainly composed of aluminum, and titanium nitride film can be used. Furthermore, a laminated structure has low resistance as wiring, good ohmic contact can be obtained, and it can function as an anode.

[0421] Furthermore, the EL layer 616 is formed by various methods such as vapor deposition using a vapor deposition mask, inkjet printing, and spin coating. The EL layer 616 includes the configuration described in any one of Embodiments 2 to 6. In addition, other materials constituting the EL layer 616 may be low molecular weight compounds or high molecular weight compounds (including oligomers and dendrimers).

[0422] Furthermore, it is preferable to use a material with a small work function (such as Al, Mg, Li, Ca, or alloys or compounds thereof (MgAg, MgIn, AlLi, etc.)) for the second electrode 617, which is formed on the EL layer 616 and functions as a cathode. When light generated in the EL layer 616 is transmitted through the second electrode 617, it is preferable to use a laminate of a thin metal film and a transparent conductive film (such as 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.

[0423] The first electrode 613, the EL layer 616, and the second electrode 617 form a light-emitting device. This light-emitting device is the light-emitting device described in any one of Embodiments 2 to 6. The pixel portion has multiple light-emitting devices formed on it, and in the light-emitting device of this embodiment, both the light-emitting device described in any one of Embodiments 2 to 6 and light-emitting devices having other configurations may be mixed together.

[0424] Furthermore, by bonding the sealing substrate 604 to the element substrate 610 with the sealing material 605, the light-emitting device 618 is provided in the 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 material, which may be an inert gas (such as nitrogen or argon) or a sealing material. A recess is formed in the sealing substrate, and a desiccant is placed therein to suppress deterioration due to the effects of moisture, which is a preferred configuration.

[0425] Furthermore, it is preferable to use epoxy resin or glass frit for the sealing material 605. It is also desirable that these materials are as impermeable to moisture and oxygen as possible. In addition to glass substrates or quartz substrates, plastic substrates made of FRP, PVF, polyester, or acrylic resin can be used as the material for the sealing substrate 604.

[0426] Although not shown in Figures 8(A) and 8(B), a protective film may be provided on the second electrode 617. The protective film may be formed of an organic resin film or an inorganic insulating film. Alternatively, the protective film may be formed to cover the exposed portion of the sealing material 605. Furthermore, the protective film can be provided to cover the surface and sides of the pair of substrates, the sealing layer, the insulating layer, and other exposed sides.

[0427] The protective film can be made of a material that is impermeable to impurities such as water. Therefore, it is possible to effectively suppress the diffusion of impurities such as water from the outside to the inside.

[0428] Materials that constitute the protective film can include oxides, nitrides, fluorides, sulfides, ternary compounds, metals, or polymers. For example, materials 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, or indium oxide can be used. Other materials containing aluminum nitride, hafnium nitride, silicon nitride, tantalum nitride, titanium nitride, niobium nitride, molybdenum nitride, zirconium nitride, or gallium nitride can be used. Nitrides containing titanium and aluminum, oxides containing titanium and aluminum, oxides containing aluminum and zinc, sulfides containing manganese and zinc, sulfides containing cerium and strontium, oxides containing erbium and aluminum, oxides containing yttrium and zirconium can be used.

[0429] It is preferable to form the protective film using a film deposition method that provides good step coverage. One such method is the ALD method. 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 a protective film with a uniform thickness. Furthermore, it is possible to reduce the damage inflicted on the processed member when forming the protective film.

[0430] For example, by using the ALD method to form a protective film, it is possible to create a uniform, low-defect protective film on surfaces with complex uneven shapes, or on the top, sides, and back surfaces of a touch panel.

[0431] As described above, a light-emitting device can be obtained using the light-emitting device described in any one of Embodiments 2 to 6.

[0432] Since the light-emitting device in this embodiment uses the light-emitting device described in any one of Embodiments 2 to 6, a light-emitting device with good characteristics can be obtained. Specifically, since the light-emitting device described in any one of Embodiments 2 to 6 has good luminous efficiency, it is possible to make a light-emitting device with low power consumption.

[0433] Figure 9 shows an example of a light-emitting device that is made full-color by forming a light-emitting device that emits white light and providing a colored layer (color filter), etc. Figure 9(A) shows 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 drive circuit portion 1041, electrodes 1024W, 1024R, 1024G, and 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 sealing material 1032, etc.

[0434] In Figure 9(A), the colored layers (red colored layer 1034R, green colored layer 1034G, and blue colored layer 1034B) are provided on a transparent substrate 1033. A black matrix 1035 may also be provided. The transparent substrate 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. In Figure 9(A), there is an emissive layer that emits light to the outside without transmitting through the colored layers, and an emissive layer that emits light to the outside by transmitting through each colored layer. Light that does not transmit through the colored layers is white, and light that transmits through the colored layers is red, green, and blue, so an image can be represented with four colored pixels.

[0435] Figure 9(B) shows an example in which colored layers (red colored layer 1034R, green colored layer 1034G, and blue colored layer 1034B) are formed between the gate insulating film 1003 and the first interlayer insulating film 1020. Thus, the colored layers may also be provided between the substrate 1001 and the encapsulating substrate 1031.

[0436] Furthermore, although the light-emitting device described above is a bottom-emission type device that extracts light from the substrate 1001 on which the FET is formed, it may also be a top-emission type device that extracts light from the sealing substrate 1031. A cross-sectional view of the top-emission type light-emitting device is shown in Figure 10. In this case, the substrate 1001 can be a substrate that does not transmit light. The process is the same as for the bottom-emission type light-emitting device until the connecting electrode that connects the FET and the anode of the light-emitting device is fabricated. After that, a third interlayer insulating film 1037 is formed covering the electrode 1022. This insulating film may also play a role in planarization. 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.

[0437] Electrodes 1024W, 1024R, 1024G, and 1024B of the light-emitting device are designated as anodes here, but they may also be cathodes. Furthermore, in the case of a top-emission type light-emitting device as shown in Figure 10, it is preferable that electrodes 1024W, 1024R, 1024G, and 1024B be reflective electrodes. The configuration of the EL layer 1028 is as described as unit 103X in any one of Embodiments 2 to 6, and the element structure is such that white light emission can be obtained.

[0438] In a top-emission structure as shown in Figure 10, sealing can be performed with a sealing substrate 1031 having colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B). A black matrix 1035 may also be provided on the sealing substrate 1031 so as to be located between pixels. The colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B) or the black matrix 1035 may be covered with an overcoat layer. The sealing substrate 1031 should be a translucent substrate. In addition, although an example of full-color display using four colors, red, green, blue, and white, is shown here, it is not particularly limited, and full-color display may also be performed using four colors, red, yellow, green, and blue, or three colors, red, green, and blue.

[0439] In top-emission type light-emitting devices, a microcavity structure can be suitably applied. A light-emitting device having a microcavity structure is obtained by using a reflective electrode as the first electrode and a semi-transparent / semi-reflective electrode as the second electrode. There is at least an EL layer between the reflective electrode and the semi-transparent / semi-reflective electrode, and there is at least a light-emitting layer that forms a light-emitting region.

[0440] The reflective electrode has a visible light reflectance of 40% to 100%, preferably 70% to 100%, and its resistivity is 1 × 10⁻⁶. -2 The film is assumed to have a density of Ω·cm or less. Furthermore, the semi-transparent / semi-reflective electrode has a visible light reflectance of 20% to 80%, preferably 40% to 70%, and its resistivity is 1 × 10⁻⁶. -2 Assume the membrane is less than Ω·cm in diameter.

[0441] The light emitted from the light-emitting layer contained in the EL layer is reflected by the reflective electrode and the semi-transparent / semi-reflective electrode, causing resonance.

[0442] This light-emitting device allows you to change the optical distance between the reflective electrode and the semi-transparent / semi-reflective electrode by changing the thickness of the transparent conductive film or the aforementioned composite material, carrier transport material, etc. This makes it possible to strengthen light of resonant wavelengths and attenuate light of non-resonant wavelengths between the reflective electrode and the semi-transparent / semi-reflective electrode.

[0443] Furthermore, since the light reflected back by the reflective electrode (first reflected light) interferes significantly with the light that directly enters the semi-transparent / semi-reflective electrode from the light-emitting layer (first incident light), 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 greater than or equal to 1, and λ is the wavelength of the light emission to be amplified). By adjusting this optical distance, the phases of the first reflected light and the first incident light can be aligned, and the light emission from the light-emitting layer can be further amplified.

[0444] In the above configuration, the EL layer may have a structure with multiple light-emitting layers or a structure with a single light-emitting layer. For example, it may be applied to a configuration in which multiple EL layers are provided in a single light-emitting device with a charge generation layer in between, and one or more light-emitting layers are formed in each EL layer, in combination with the tandem light-emitting device configuration described above.

[0445] By incorporating a microcavity structure, it becomes possible to enhance the emission intensity in the front direction at specific wavelengths, thereby reducing power consumption. Furthermore, in the case of a light-emitting device that displays images using four sub-pixels of red, yellow, green, and blue, in addition to the brightness enhancement effect of yellow emission, a microcavity structure tailored to the wavelength of each color can be applied to all sub-pixels, resulting in a light-emitting device with excellent characteristics.

[0446] Since the light-emitting device in this embodiment uses the light-emitting device described in any one of Embodiments 2 to 6, a light-emitting device with good characteristics can be obtained. Specifically, since the light-emitting device described in any one of Embodiments 2 to 6 has good luminous efficiency, it is possible to make a light-emitting device with low power consumption.

[0447] Up to this point, we have described an active matrix type light-emitting device, but from here on we will describe a passive matrix type light-emitting device. Figure 11 shows a passive matrix type light-emitting device manufactured by applying the present invention. Figure 11(A) is a perspective view showing the light-emitting device, and Figure 11(B) is a cross-sectional view of Figure 11(A) cut along the X and Y lines. In Figure 11, an EL layer 955 is provided on the substrate 951 between electrodes 952 and 956. The ends of electrodes 952 are covered with an insulating layer 953. A partition layer 954 is provided on the insulating layer 953. The side walls of the partition layer 954 have a slope such that the distance between one side wall and the other side wall narrows as they get closer to the substrate surface. In other words, the cross-section of the partition layer 954 in the short-side direction is trapezoidal, with the bottom side (facing the same direction as the surface direction of the insulating layer 953 and in contact with the insulating layer 953) being shorter than the top side (facing the same direction as the surface direction of the insulating layer 953 and not in contact with the insulating layer 953). By providing the partition layer 954 in this way, it is possible to prevent malfunctions of the light-emitting device caused by static electricity, etc. Furthermore, even in a passive matrix type light-emitting device, the light-emitting device described in any one of Embodiments 2 to 6 can be used, resulting in a light-emitting device with good reliability or low power consumption.

[0448] As described above, the light-emitting device is suitable for use as a display device for representing images because it is possible to control each of the numerous minute light-emitting devices arranged in a matrix.

[0449] Furthermore, this embodiment can be freely combined with other embodiments.

[0450] (Embodiment 11) In this embodiment, an example of using the light-emitting device described in any one of Embodiments 2 to 6 as an illumination device will be described with reference to Figure 12. Figure 12(B) is a top view of the illumination device, and Figure 12(A) is a cross-sectional view of ef in Figure 12(B).

[0451] In this embodiment, the lighting device has a first electrode 401 formed on a translucent 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 from a translucent material.

[0452] A pad 412 for supplying voltage to the second electrode 404 is formed on the substrate 400.

[0453] An EL layer 403 is formed on the first electrode 401. The EL layer 403 corresponds to a configuration combining layer 104, unit 103X, and layer 105 in any one of Embodiments 2 to 6, or a configuration combining layer 104, unit 103X, layer 106, unit 103X2, and layer 105. Please refer to the respective descriptions for details on these configurations.

[0454] A second electrode 404 is formed by covering the EL layer 403. The second electrode 404 corresponds to electrode 552X in any one of Embodiments 2 to 6. When light emission is extracted from the first electrode 401 side, the second electrode 404 is formed of a material with high reflectivity. Voltage is supplied to the second electrode 404 by connecting it to the pad 412.

[0455] As described above, the lighting device shown in this embodiment has a light-emitting device having a first electrode 401, an EL layer 403, and a second electrode 404. Since this light-emitting device is a light-emitting device with high luminous efficiency, the lighting device in this embodiment can be a lighting device with low power consumption.

[0456] The lighting device is completed by fixing and sealing the substrate 400 on which the light-emitting device having the above configuration is formed, and the sealing substrate 407 using sealing materials 405 and 406. Either sealing material 405 or 406 may be used. In addition, a desiccant can be mixed into the inner sealing material 406 (not shown in Figure 12(B)), which allows for the adsorption of moisture and leads to improved reliability.

[0457] Furthermore, by extending the pad 412 and a portion of the first electrode 401 outside the sealing material 405 and sealing material 406, it can be used as an external input terminal. Alternatively, an IC chip 420 with a converter or the like may be provided on top of it.

[0458] 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 the EL element, and can be a lighting device with low power consumption.

[0459] (Embodiment 12) This embodiment describes an example of an electronic device that includes a light-emitting device as described in any one of Embodiments 2 to 6. The light-emitting device described in any one of Embodiments 2 to 6 has good luminous efficiency and low power consumption. As a result, the electronic device described in this embodiment can be an electronic device having a light-emitting section with low power consumption.

[0460] Examples of electronic devices to which the above-mentioned light-emitting devices are applied include television equipment (also called televisions or television receivers), monitors for computers, digital cameras, digital video cameras, digital photo frames, mobile phones (also called mobile phones or mobile phone devices), portable game consoles, personal digital assistants, sound playback devices, and large game machines such as pachinko machines. Specific examples of these electronic devices are shown below.

[0461] Figure 13(A) shows an example of a television system. The television system has a display unit 7103 incorporated into a housing 7101. This figure also shows a configuration in which the housing 7101 is supported by a stand 7105. The display unit 7103 is capable of displaying images, and the display unit 7103 is configured by arranging the light-emitting devices described in any one of Embodiments 2 to 6 in a matrix.

[0462] The television system can be operated using the operation switches on the housing 7101 or a separate remote control unit 7110. The remote control unit 7110 has operation keys 7109 that allow for channel or volume control, and the image displayed on the display unit 7103 can be controlled. Alternatively, a display unit 7107 may be provided on the remote control unit 7110 to display output information.

[0463] The television system shall consist of a receiver or modem. The receiver will be able to receive general television broadcasts, and by connecting to a wired or wireless communication network via the modem, it will also be possible to perform one-way (from sender to receiver) or two-way (between sender and receiver, or between receivers, etc.) information communication.

[0464] Figure 13(B) shows a computer, which includes a main unit 7201, a housing 7202, a display unit 7203, a keyboard 7204, an external connection port 7205, a pointing device 7206, etc. This computer is manufactured by arranging the light-emitting devices described in any one of Embodiments 2 to 6 in a matrix and using them for the display unit 7203. The computer in Figure 13(B) may also take the form shown in Figure 13(C). The computer in Figure 13(C) is provided with a second display unit 7210 instead of the keyboard 7204 and pointing device 7206. The second display unit 7210 is a touch panel, and input can be performed by operating the input display shown on the second display unit 7210 with a finger or a dedicated pen. In addition to the input display, the second display unit 7210 can also display other images. The display unit 7203 may also be a touch panel. The two screens are connected by a hinge, which prevents problems such as scratching or damaging the screens when storing or transporting the device.

[0465] Figure 13(D) shows an example of a mobile terminal. The mobile terminal includes a display unit 7402 incorporated into a housing 7401, as well as operation buttons 7403, an external connection port 7404, a speaker 7405, a microphone 7406, and the like. The mobile terminal has a display unit 7402 made by arranging the light-emitting devices described in any one of Embodiments 2 to 6 in a matrix.

[0466] The mobile terminal shown in Figure 13(D) can also be configured to allow information input by touching the display unit 7402 with a finger or other object. In this case, operations such as making a phone call or composing an email can be performed by touching the display unit 7402 with a finger or other object.

[0467] The display unit 7402 has three main modes. The first is a display mode that primarily displays images, the second is an input mode that primarily inputs information such as text, and the third is a display + input mode that combines the display mode and the input mode.

[0468] For example, when making a phone call or composing an email, the display unit 7402 should be set to a text input mode, which primarily focuses on text input, and the user should input the characters displayed on the screen. In this case, it is preferable to display a keyboard or number buttons on most of the screen of the display unit 7402.

[0469] Furthermore, by providing a detection device with tilt-detecting sensors such as a gyroscope and an accelerometer inside the mobile terminal, the orientation of the mobile terminal (portrait or landscape) can be determined, and the screen display of the display unit 7402 can be automatically switched accordingly.

[0470] Furthermore, the screen mode can be switched by touching the display unit 7402 or by operating the operation button 7403 on the housing 7401. It is also possible to switch modes depending on the type of image displayed on the display unit 7402. For example, if the image signal displayed on the display unit is video data, it can be switched to display mode; if it is text data, it can be switched to input mode.

[0471] Furthermore, in input mode, the system may detect a signal detected by the optical sensor of the display unit 7402 and, if there is no input via touch operation on the display unit 7402 for a certain period of time, control may be made to switch the screen mode from input mode to display mode.

[0472] The display unit 7402 can also function as an image sensor. For example, by touching the display unit 7402 with the palm or finger, palm prints, fingerprints, etc., can be captured to perform user authentication. Furthermore, by using a backlight that emits near-infrared light or a sensing light source that emits near-infrared light in the display unit, finger veins, palm veins, etc., can also be captured.

[0473] Figure 14(A) is a schematic diagram showing an example of a cleaning robot.

[0474] The cleaning robot 5100 has a display 5101 on its top surface, multiple cameras 5102 on its sides, a brush 5103, and control buttons 5104. Although not shown in the illustration, the cleaning robot 5100 also has wheels, a suction port, etc. on its underside. The cleaning robot 5100 is also equipped with various sensors, including an infrared sensor, an ultrasonic sensor, an accelerometer, a piezoelectric sensor, a light sensor, and a gyroscope. Furthermore, the cleaning robot 5100 is equipped with a means of wireless communication.

[0475] The cleaning robot 5100 is self-propelled, can detect dirt 5120, and can suck up the dirt through a suction port located on its underside.

[0476] Furthermore, the cleaning robot 5100 can analyze images captured by the camera 5102 to determine the presence or absence of obstacles such as walls, furniture, or steps. If the image analysis detects objects that could become entangled in the brush 5103, such as wiring, it can stop the brush 5103 from rotating.

[0477] The display 5101 can display information such as the remaining battery level or the amount of dirt collected. The path taken by the cleaning robot 5100 may also be displayed on the display 5101. Alternatively, the display 5101 may be a touch panel, and operation buttons 5104 may be provided on the display 5101.

[0478] 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. Therefore, the owner of the cleaning robot 5100 can check the status of the room even when they are away from home. In addition, the display 5101 can be viewed on the portable electronic device 5140, such as a smartphone.

[0479] A light-emitting device according to one aspect of the present invention can be used in a display 5101.

[0480] The robot 2100 shown in Figure 14(B) includes a computing unit 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.

[0481] The microphone 2102 has the function of detecting the user's voice and ambient sounds. The speaker 2104 has the function of emitting sound. The robot 2100 can communicate with the user using the microphone 2102 and speaker 2104.

[0482] The display 2105 has the function of displaying various types of information. The robot 2100 can display the 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, and by installing it in a fixed position on the robot 2100, charging and data transfer can be made possible.

[0483] The upper camera 2103 and the lower camera 2106 have the function of imaging the area around the robot 2100. In addition, the obstacle sensor 2107 can detect the presence or absence of obstacles in the direction of travel when the robot 2100 moves forward using the movement mechanism 2108. The robot 2100 can recognize its surrounding environment and move safely using the upper camera 2103, the lower camera 2106 and the obstacle sensor 2107. The light-emitting device according to one aspect of the present invention can be used in the display 2105.

[0484] Figure 14(C) shows 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 operation switch), connection terminals 5006, a sensor 5007 (including functions for measuring force, displacement, position, velocity, acceleration, angular velocity, rotational speed, distance, light, liquid, magnetism, temperature, chemical substances, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared radiation), a microphone 5008, a display unit 5002, a support unit 5012, an earphone 5013, etc.

[0485] A light-emitting device according to one aspect of the present invention can be used in the display unit 5001 and the display unit 5002.

[0486] Figure 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 Figure 15 has a housing 2001 and a light source 2002, and the lighting device described in Embodiment 11 may be used as the light source 2002.

[0487] Figure 16 shows an example of using the light-emitting device described in any one of Embodiments 2 to 6 as an indoor lighting device 3001. Since the light-emitting device described in any one of Embodiments 2 to 6 is a light-emitting device with high luminous efficiency, it can be used as a lighting device with low power consumption. Furthermore, since the light-emitting device described in any one of Embodiments 2 to 6 can be made to cover a large area, it can be used as a large-area lighting device. In addition, 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.

[0488] The light-emitting device described in any one of Embodiments 2 to 6 can also be mounted on the windshield or dashboard of an automobile. Figure 17 shows one embodiment in which the light-emitting device described in any one of Embodiments 2 to 6 is used on the windshield or dashboard of an automobile. Display areas 5200 to 5203 are display areas provided using the light-emitting device described in any one of Embodiments 2 to 6.

[0489] Display area 5200 and display area 5201 are display devices equipped with a light-emitting device according to any one of Embodiments 2 to 6, which is installed on the windshield of an automobile. The light-emitting device according to any one of Embodiments 2 to 6 can be made into a so-called see-through display device, where the opposite side is visible, by making the first electrode and the second electrode from translucent electrodes. If the display is in a see-through state, it can be installed on the windshield of an automobile without obstructing the view. When providing transistors for driving, it is preferable to use translucent transistors such as organic transistors made of organic semiconductor materials or transistors using oxide semiconductors.

[0490] The display area 5202 is a display device equipped with a light-emitting device described in any one of Embodiments 2 to 6, which is provided on the pillar. By displaying images from an imaging means provided on the vehicle body on the display area 5202, the field of view obstructed by the pillar can be supplemented. Similarly, the display area 5203 provided on the dashboard can compensate for blind spots and enhance safety by displaying images from an imaging means provided on the outside of the vehicle, which is obstructed by the vehicle body. By displaying images in a way that supplements the parts that are not visible, safety checks can be performed more naturally and without discomfort.

[0491] Display area 5203 can provide various information by displaying navigation information, speed or RPM, mileage, fuel level, gear status, air conditioning settings, etc. The display items and layout can be changed as needed to suit the user's preferences. This information can also be provided in display areas 5200 to 5202. Furthermore, display areas 5200 to 5203 can also be used as lighting devices.

[0492] Figures 18(A) to 18(C) also show the foldable portable information terminal 9310. Figure 18(A) shows the portable information terminal 9310 in its unfolded state. Figure 18(B) shows the portable information terminal 9310 in an intermediate state, transitioning from either the unfolded or folded state to the other. Figure 18(C) shows the portable information terminal 9310 in its folded state. The portable information terminal 9310 offers excellent portability in its folded state and excellent readability of the display due to its seamless, wide display area in its unfolded state.

[0493] The display panel 9311 is supported by three housings 9315 connected by a hinge 9313. The display panel 9311 may also 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 hinge 9313. A light-emitting device according to one aspect of the present invention can be used in the display panel 9311.

[0494] Furthermore, the configuration shown in this embodiment can be used by appropriately combining the configurations shown in Embodiments 2 to 6.

[0495] As described above, the application range of the light-emitting device equipped with the light-emitting device described in any one of Embodiments 2 to 6 is extremely broad, and this light-emitting device can be applied to electronic devices in all fields. By using the light-emitting device described in any one of Embodiments 2 to 6, it is possible to obtain electronic devices with low power consumption.

[0496] This embodiment can be appropriately combined with other embodiments shown in this specification. [Examples]

[0497] In this example, the physical properties and synthesis method of an organic compound according to one aspect of the present invention will be described with reference to Figures 19 to 24.

[0498] Figure 19 shows Ir(ppy)2(5m4dppy-d3) 1 This figure illustrates the results of measuring the 1H NMR spectrum.

[0499] Figure 20 illustrates the results of measuring the absorption and emission spectra of a dichloromethane solution containing Ir(ppy)2(5m4dppy-d3).

[0500] Figure 21 shows Ir(5m4dppy-d3)2(ppy) 1 This figure illustrates the results of measuring the 1H NMR spectrum.

[0501] Figure 22 illustrates the results of measuring the absorption and emission spectra of a dichloromethane solution containing Ir(5m4dppy-d3)2(ppy).

[0502] Figure 23 shows Ir(5iBu4mppy-d5)2(4mmtBup5mppy-d3) 1 This figure illustrates the results of measuring the 1H NMR spectrum.

[0503] Figure 24 illustrates the results of measuring the absorption and emission spectra of a dichloromethane solution containing Ir(5iBu4mppy-d5)2(4mmtBup5mppy-d3).

[0504] (Synthesis Example 1) This synthesis example describes the synthesis of {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)), which is shown by structural formula (101) in Embodiment 1.

[0505] [ka]

[0506] Step 1: Synthesis of 5-methyl-2,4-diphenylpyridine 5.00 g of 2,4-dichloro-5-methylpyridine, 8.31 g of phenylboronic acid, 180 mL of toluene, 18 mL of water, and 43.30 g of tripotassium phosphate were placed in a three-necked flask fitted with a reflux condenser, and the inside was purged with nitrogen. After degassing by stirring under reduced pressure in the flask, 0.28 g of tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd2(dba)3) and 0.51 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (abbreviation: S-Phos) were added. The mixture was reacted at 110°C for 6.5 hours with stirring. The synthesis scheme (1a) of Step 1 is shown below.

[0507] After a predetermined time had elapsed, the target product was extracted using toluene. The residue obtained by distilling off the toluene from the extract was purified using silica gel column chromatography with a mixed solvent of hexane and ethyl acetate (hexane:ethyl acetate = 10:1) as the mobile phase to obtain 7.75 g (100% yield) of a yellow, oily pyridine derivative.

[0508] [ka]

[0509] Step 2: Synthesis of 5-(methyl-d3)-2,4-diphenylpyridine (abbreviation: H5m4dppy-d3) 2.79 g of 5-methyl-2,4-diphenylpyridine obtained in Step 1 above, 0.66 g of sodium tert-butoxide (abbreviated as tBuONa), and 16 mL of deuterated dimethyl sulfoxide (abbreviated as DMSO-d6) were placed in a round-bottom flask fitted with a reflux tubing, and the inside was purged with argon. This reaction vessel was heated by irradiating it with 2.45 GHz microwaves at an output of 100 W for 2 hours. The synthesis scheme (1b) for Step 2 is shown below.

[0510] After a predetermined time had elapsed, the target product was extracted using ethyl acetate. The residue obtained by distilling off the ethyl acetate from the extract was purified using flash column chromatography with a mixed solvent of hexane and ethyl acetate (hexane:ethyl acetate = 10:1) as the mobile phase to obtain 2.23 g (79% yield) of a yellowish-white solid pyridine derivative.

[0511] [ka]

[0512] Step 3: Synthesis of {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)) 10.0 g of di-μ-chlorotetrakis[2-(2-pyridinyl-κN)phenyl-κC]diiridium(III) (abbreviated as [Ir(ppy)2Cl]2) and 465 mL of dichloromethane (CH2Cl2) were placed in a light-shielded three-necked flask, and the inside was purged with nitrogen. A mixed solution of 7.21 g of silver trifluoromethanesulfonate and 280 mL of methanol was added dropwise, and the mixture was stirred at room temperature for 24 hours. After the specified time, the reaction mixture was filtered using Celite as a filter aid. The obtained filtrate was concentrated to obtain 14.0 g of a yellowish-brown solid.

[0513] 5.00 g of the yellowish-brown solid obtained above, 1.68 g of 5-(methyl-d3)-2,4-diphenylpyridine (abbreviation: H5m4dppy-d3), 70 mL of 2-ethoxyethanol, and 70 mL of N,N-dimethylformamide (abbreviation: DMF) were placed in a three-necked flask equipped with a reflux tube, and the inside was purged with nitrogen. While stirring, the reaction was carried out at 160 °C for 7 hours. The synthesis scheme (1c) of Step 3 is shown below.

[0514]

Chemical formula

[0515] After a predetermined time had elapsed, the residue obtained by distilling off the solvent was purified using silica gel column chromatography with toluene as the mobile phase and high-performance liquid chromatography with chloroform as the mobile phase. Further, from the obtained solid and a mixed solution of toluene and hexane, 1.61 g (yield 15%) of a yellow solid was obtained using the recrystallization method. The 1.61 g of the yellow solid was sublimation-purified by the train sublimation method to obtain 1.4 g (yield 88%) of the target product in the form of a yellow solid. The sublimation purification conditions were a pressure of 2.6 Pa, an argon gas flow rate of 10 mL / min, and a heating temperature of 305 °C.

[0516] As a result of measurement using nuclear magnetic resonance spectroscopy ( 1 1H-NMR), it was confirmed that the yellow solid obtained in Step 3 above was Ir(ppy)2(5m4dppy-d3). 1 The 1H-NMR chart is shown in Figure 19, and the analysis results are shown below.

[0517] 1 1H-NMR.δ(CD2Cl2): 6.73 - 6.99 (m, 11H), 7.40 - 7.44 (m, 4H), 7.48 (t, 2H), 7.61 - 7.71 (m, 7H), 7.79 (s, 1H), 7.94 (dd, 2H).

[0518] Figure 20 shows the measurement results of the ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum of a dichloromethane solution containing Ir(ppy)2(5m4dppy-d3). The horizontal axis represents wavelength, and the vertical axis represents absorption intensity or emission intensity. Ir(ppy)2(5m4dppy-d3) has an emission peak at 537 nm, and green emission was observed from the dichloromethane solution.

[0519] Absorption spectra were measured using a UV-Vis spectrophotometer (V550 model, JASCO Corporation) with a dichloromethane solution (0.0107 mmol / L) placed in a quartz cell at room temperature. The absorption spectrum shown in Figure 20 is the result of subtracting the absorption spectrum measured with only dichloromethane in a quartz cell from the absorption spectrum measured with the dichloromethane solution (0.0107 mmol / L) in a quartz cell.

[0520] Furthermore, to measure the emission spectrum, a spectrofluorometer (FP-8600DS model, manufactured by JASCO Corporation) was used. A glove box (LABstar M13 (1250 / 780), manufactured by Bright Co., Ltd.) was used to place a dichloromethane deoxygenated solution (0.0107 mmol / L) in a quartz cell under a nitrogen atmosphere, seal it tightly, and perform the measurement at room temperature.

[0521] Furthermore, for measuring the emission quantum yield, an absolute PL quantum yield analyzer (Hamamatsu Photonics Ltd. C11347-01) was used. In a glove box (Bright Co., Ltd. LABstarM13 (1250 / 780)), a dichloromethane deoxygenated solution (0.0107 mmol / L) was placed in a quartz cell under a nitrogen atmosphere, sealed tightly, and measured at room temperature. Ir(ppy)2 (5m4dppy-d3) excited with light at a wavelength of 410 nm was 85%. It emitted light with a quantum emission yield of 73%. This is extremely high compared to the quantum emission yield of [2-d3-methyl-(2-pyridinyl-κN)benzofl[2,3-b]pyridine-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(ppy)2(mbfpypy-d3)). High luminescence efficiency can be expected by using Ir(ppy)2(5m4dppy-d3) in light-emitting devices.

[0522] For the measurement of the emission quantum yield of Ir(ppy)2(mbfpypy-d3), an absolute PL quantum yield analyzer (Hamamatsu Photonics Ltd., C11347-01) was used. In a glove box (Bright Co., Ltd., LABstar M13 (1250 / 780)), a dichloromethane deoxygenated solution (0.0103 mmol / L) was placed in a quartz cell under a nitrogen atmosphere, sealed tightly, and the measurement was performed at room temperature. Ir(ppy)2(mbfpypy-d3) excited with light of a wavelength of 460 nm emitted light with an emission quantum yield of 73%.

[0523] (Synthesis Example 2) This synthesis example describes the synthesis of 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)), which is shown by structural formula (102) in Embodiment 1.

[0524] [ka]

[0525] Note that the synthesis method described in Synthesis Example 2 differs from the synthesis method described in Synthesis Example 1 in Step 3. Here, we will explain the different steps in detail, and refer to the above explanation for similar steps.

[0526] Step 3: Synthesis of 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)) 10.0 g of di-μ-chlorotetrakis[2-(2-pyridinyl-κN)phenyl-κC]diiridium(III) (abbreviated as [Ir(ppy)2Cl]2) and 465 mL of dichloromethane were placed in a light-shielded three-necked flask, and the inside was purged with nitrogen. A mixed solution of 7.21 g of silver trifluoromethanesulfonate (abbreviated as AgOTf) and 280 mL of methanol was added dropwise, and the mixture was stirred at room temperature for 24 hours. After the specified time, the reaction mixture was filtered using Celite as a filter aid. The obtained filtrate was concentrated to obtain 14.0 g of a yellowish-brown solid.

[0527] 5.00 g of the yellowish-brown solid obtained above, 1.68 g of 5-(methyl-d3)-2,4-diphenylpyridine (abbreviated as H5m4dppy-d3), 70 mL of 2-ethoxyethanol, and 70 mL of N,N-dimethylformamide (abbreviated as DMF) were placed in a three-necked flask fitted with a reflux condenser, and the inside was purged with nitrogen. The mixture was reacted at 160°C for 7 hours with stirring. The synthesis scheme (2c) for step 3 is shown below.

[0528] [ka]

[0529] After a predetermined time, the solvent was removed by distillation, and the resulting residue was purified using silica gel column chromatography with toluene as the mobile phase and high-performance liquid chromatography with chloroform as the mobile phase. Furthermore, 0.79 g of a yellow solid (yield 7%) was obtained from the resulting solid and a mixed solution of toluene and hexane by recrystallization. This 0.79 g of yellow solid was sublimated by the train sublimation method to obtain 0.61 g of the target product in yellow solid form (yield 77%). The sublimation purification conditions were a pressure of 2.6 Pa, an argon gas flow rate of 10 mL / min, and a heating temperature of 288 °C.

[0530] Nuclear magnetic resonance spectroscopy ( 1 Measurements using 1H-NMR confirmed that the yellow solid obtained in step 3 was Ir(5m4dppy-d3)2(ppy). 1 The H-NMR chart is shown in Figure 21, and the analysis results are shown below.

[0531] 1 H-NMR.δ(CD2Cl2):6.72-6.93(m,9H),7.00(t,1H),7.41-7.50(m,11H),7.53(s,1H),7.63-7.74(m,5H),7.80(d,2H),7.95(d,1H).

[0532] Figure 22 shows the measurement results of the ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum of a dichloromethane solution containing Ir(5m4dppy-d3)2(ppy). The horizontal axis represents wavelength, and the vertical axis represents absorption intensity or emission intensity. Ir(5m4dppy-d3)2(ppy) has an emission peak at 543 nm, and green emission was observed from the dichloromethane solution.

[0533] Absorption spectra were measured using a UV-Vis spectrophotometer (JASCO Corporation, Model V550) with a dichloromethane solution (0.0103 mmol / L) placed in a quartz cell at room temperature. The absorption spectrum shown in Figure 22 is the result of subtracting the absorption spectrum measured with only dichloromethane in a quartz cell from the absorption spectrum measured with the dichloromethane solution (0.0103 mmol / L) in a quartz cell.

[0534] Furthermore, to measure the emission spectrum, a spectrofluorometer (FP-8600DS model, manufactured by JASCO Corporation) was used. A glove box (LABstar M13 (1250 / 780), manufactured by Bright Co., Ltd.) was used to place a dichloromethane deoxygenated solution (0.0103 mmol / L) in a quartz cell under a nitrogen atmosphere, seal it tightly, and perform the measurement at room temperature.

[0535] Furthermore, to measure the emission quantum yield, an absolute PL quantum yield analyzer (Hamamatsu Photonics Ltd., C11347-01) was used. In a glove box (Bright Co., Ltd., LABstar M13 (1250 / 780)), a dichloromethane deoxygenated solution (0.0103 mmol / L) was placed in a quartz cell under a nitrogen atmosphere, sealed tightly, and measured at room temperature. Ir(5m4dppy-d3)2(ppy), excited with light of wavelength 450 nm, emitted light with an emission quantum yield of 87%. This is extremely high compared to the emission quantum yield of Ir(ppy)2(mbfpypy-d3), which is 73%. High luminescence efficiency can be expected by using Ir(5m4dppy-d3)2(ppy) in light-emitting devices.

[0536] (Synthesis Example 3) This synthesis example describes the synthesis of {2-[4-(3,5-di-tert-butylphenyl)-5-(methyl-d3)-2-pyridinyl-κN]phenyl-κC}bis{2-[4-(methyl-d3)-5-(2-methylpropyl-1,1-d2)-2-pyridinyl-κN]phenyl-κC}iridium(III) (abbreviation: Ir(5iBu4mppy-d5)2(4mmtBup5mppy-d3)), which is shown by structural formula (107) in Embodiment 1.

[0537] [ka]

[0538] Step 1: Synthesis of 4-chloro-5-methyl-2-phenylpyridine 10.00 g of 2,4-dichloro-5-methylpyridine, 7.75 g of phenylboronic acid, 110 mL of toluene, 55 mL of ethanol, 18 mL of water, and 11.66 g of sodium carbonate were placed in a three-necked flask fitted with a reflux condenser, and the inside was purged with nitrogen. After degassing by stirring under reduced pressure in the flask, 1.43 g of tetrakis(triphenylphosphine)palladium(0) (abbreviation: Pd(PPh3)4) was added. The reaction was carried out at 90°C for 7 hours with stirring. The synthesis scheme (3a) for Step 1 is shown below.

[0539] After a predetermined time had elapsed, the target product was extracted using toluene. The residue obtained by distilling off the toluene from the extract was purified using silica gel column chromatography with a mixed solvent of hexane and ethyl acetate (hexane:ethyl acetate = 10:1) as the mobile phase to obtain 11.32 g (90% yield) of a white solid pyridine derivative.

[0540] [ka]

[0541] Step 2: Synthesis of 4-(3,5-di-tert-butylphenyl)-5-methyl-2-phenylpyridine 11.32 g of 4-chloro-5-methyl-2-phenylpyridine obtained in Step 1 above, 14.32 g of 3,5-di-tert-butylphenylboronic acid, 330 mL of toluene, 33 mL of water, and 35.33 g of tripotassium phosphate were placed in a three-necked flask fitted with a reflux condenser, and the inside was purged with nitrogen. After degassing by stirring under reduced pressure in the flask, 0.51 g of tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd2(dba)3) and 0.91 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (abbreviation: S-Phos) were added. The reaction was carried out at 110°C for 7 hours with stirring. The synthesis scheme (3b) for Step 2 is shown below.

[0542] After a predetermined time, the target product was extracted using toluene. Toluene was removed from the extract, and hexane was added to the residue. The mixture was washed with hexane while suction filtration. The resulting solid was dissolved in dichloromethane, and the reaction product was filtered using a filter aid consisting of layers of Celite, aluminum oxide, and Celite. The resulting filtrate was concentrated to obtain 11.47 g (58% yield) of a white solid pyridine derivative.

[0543] [ka]

[0544] Step 3: Synthesis of 4-(3,5-di-tert-butylphenyl)-5-(methyl-d3)-2-phenylpyridine (abbreviation: H4mmtBup5mppy-d3) 11.47 g of 4-(3,5-di-tert-butylphenyl)-5-methyl-2-phenylpyridine obtained in step 2 above, 1.85 g of sodium tert-butoxide, and 45 mL of dimethyl sulfoxide were placed in a round-bottom flask fitted with a reflux condenser, and the inside was purged with argon. This reaction vessel was heated by irradiating it with 2.45 GHz microwaves at an output of 100 W for 1.5 hours. The synthesis scheme (3c) for step 3 is shown below.

[0545] After a predetermined time had elapsed, the target product was extracted using ethyl acetate. The residue obtained by distilling off the ethyl acetate from the extract was dissolved in dichloromethane, and the reaction product was filtered using a filter aid consisting of layers of Celite, aluminum oxide, and Celite in that order. The resulting filtrate was concentrated to obtain 6.61 g (yield 57%) of a white solid pyridine derivative.

[0546] [ka]

[0547] Step 4: Synthesis of 4-methyl-5-(2-methylpropyl)-2-phenylpyridine 6.31 g of 5-bromo-4-methyl-2-phenylpyridine, 5.20 g of isobutylboronic acid, 255 mL of toluene, and 21.71 g of tripotassium phosphate were placed in a three-necked flask fitted with a reflux condenser, and the inside was purged with nitrogen. After degassing by stirring under reduced pressure in the flask, 0.24 g of tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd2(dba)3) and 0.42 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (abbreviation: S-Phos) were added. The reaction was carried out at 120°C for 6 hours with stirring. The synthesis scheme (3d) for step 4 is shown below.

[0548] After a predetermined time had elapsed, the solvent was concentrated. The resulting residue was purified using silica gel column chromatography with a mixed solvent of hexane and ethyl acetate (hexane:ethyl acetate = 20:1) as the mobile phase to obtain 3.89 g (yield 68%) of a pale yellow, oily pyridine derivative.

[0549] [ka]

[0550] Step 5: Synthesis of 4-(methyl-d3)-5-(2-methylpropyl-1,1-d2)-2-phenylpyridine (abbreviation: H5iBu4mppy-d5) 3.89 g of 4-methyl-5-(2-methylpropyl)-2-phenylpyridine obtained in step 4 above, 1.02 g of sodium tert-butoxide, and 25 mL of dimethyl sulfoxide were placed in a round-bottom flask fitted with a reflux condenser, and the inside was purged with argon. This reaction vessel was heated by irradiating it with a 2.45 GHz microwave at an output of 100 W for 2 hours. The synthesis scheme (3e) for step 5 is shown below.

[0551] After a predetermined time had elapsed, the target product was extracted using ethyl acetate. The residue obtained by distilling off the ethyl acetate from the extract was purified using silica gel column chromatography with a mixed solvent of hexane and ethyl acetate (hexane:ethyl acetate = 20:1) as the mobile phase to obtain 3.23 g (81% yield) of a pale yellow, oily pyridine derivative.

[0552] [ka]

[0553] Step 6: Synthesis of di-μ-chlorotetrakis{2-[4-(methyl-d3)-5-(2-methylpropyl-1,1-d2)-2-pyridinyl-κN]phenyl-κC}diiridium(III) (abbreviation: [Ir(5iBu4mppy-d5)2Cl]2) 15 mL of 2-ethoxyethanol, 5 mL of water, 3.23 g of H5iBu4mppy-d5 obtained in step 5 above, and 2.03 g of iridium chloride hydrate (IrCl3·H2O) were placed in a round-bottom flask fitted with a reflux tubing, and the inside was purged with argon. This reaction vessel was heated by irradiating it with a 2.45 GHz microwave at an output of 100 W for 1 hour. The synthesis scheme (3f) for step 6 is shown below.

[0554] After a predetermined time had elapsed, the mixture in the flask was washed with methanol while being filtered by suction to obtain 2.38 g (52% yield) of a yellow solid dinuclear complex (abbreviated as [Ir(5iBu4mppy-d5)2Cl]2).

[0555] [ka]

[0556] Step 7: Synthesis of {2-[4-(3,5-di-tert-butylphenyl)-5-(methyl-d3)-2-pyridinyl-κN]phenyl-κC}bis{2-[4-(methyl-d3)-5-(2-methylpropyl-1,1-d2)-2-pyridinyl-κN]phenyl-κC}iridium(III) (abbreviation: Ir(5iBu4mppy-d5)2(4mmtBup5mppy-d3)) 2.35 g of di-μ-chlorotetrakis{2-[4-(methyl-d3)-5-(2-methylpropyl-1,1-d2)-2-pyridinyl-κN]phenyl-κC}diiridium(III) (abbreviated as [Ir(5iBu4mppy-d5)2Cl]2) obtained in step 6 above, and 84 mL of dichloromethane were placed in a light-shielded three-necked flask, and the inside was purged with nitrogen. A mixed solution of 1.32 g of silver trifluoromethanesulfonate and 17 mL of methanol was added dropwise, and the mixture was stirred at room temperature for 18 hours. After the predetermined time, the reaction mixture was filtered using Celite as a filter aid, and the resulting filtrate was concentrated to obtain 2.99 g of a yellowish-brown solid.

[0557] 2.99 g of the yellowish-brown solid obtained above, 1.25 g of 4-(3,5-di-tert-butylphenyl)-5-(methyl-d3)-2-phenylpyridine (abbreviation: H4mmtBup5mppy-d3), 35 mL of 2-ethoxyethanol, and 35 mL of N,N-dimethylformamide (DMF) were placed in a three-necked flask fitted with a reflux condenser, and the inside was purged with nitrogen. The mixture was reacted at 145°C for 7 hours with stirring. The synthesis scheme (3 g) for Step 7 is shown below.

[0558] [ka]

[0559] After the elapse of the specified time, the residue obtained by distilling off the solvent was purified by silica gel column chromatography using a mixed solvent of hexane and ethyl acetate (hexane:ethyl acetate = 2:1) as the mobile phase and by high performance liquid chromatography using chloroform as the mobile phase. Further, from the obtained solid and the mixed solution of toluene and ethanol, 0.78 g (yield 22%) of a yellow solid was obtained by the recrystallization method. 0.76 g of the yellow solid was sublimation-purified by the train sublimation method to obtain 0.67 g (yield 88%) of the yellow solid target product. The sublimation purification conditions were a pressure of 2.7 Pa, an argon gas flow rate of 5 mL / min, and a heating temperature of 280 °C.

[0560] As a result of measurement using nuclear magnetic resonance spectroscopy ( 1 1H-NMR), it was confirmed that the yellow solid obtained in Step 7 above was Ir(5iBu4mppy-d5)2(4mmtBup5mppy-d3). 1 The 1H-NMR chart is shown in Figure 23, and the analysis results are shown below.

[0561] 1 1H-NMR. δ(CD2Cl2): 0.77 - 0.84 (m, 12H), 1.35 (s, 18H), 1.65 - 1.69 (m, 2H), 6.71 - 6.90 (m, 9H), 7.19 - 7.21 (m, 3H), 7.27 (s, 1H), 7.49 - 7.52 (m, 2H), 7.58 (dd, 1H), 7.63 (t, 2H), 7.67 (s, 1H), 7.71 (s, 1H), 7.79 (s, 1H).

[0562] The measurement results of the ultraviolet-visible absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and the emission spectrum of the dichloromethane solution containing Ir(5iBu4mppy-d5)2(4mmtBup5mppy-d3) are shown in Figure 24. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity or the emission intensity. Ir(5iBu4mppy-d5)2(4mmtBup5mppy-d3) has an emission peak at 544 nm, and green emission was observed from the dichloromethane solution.

[0563] Absorption spectra were measured using a UV-Vis spectrophotometer (JASCO Corporation, Model V550) with a dichloromethane solution (0.0104 mmol / L) placed in a quartz cell at room temperature. The absorption spectrum shown in Figure 24 is the result of subtracting the absorption spectrum measured with only dichloromethane in a quartz cell from the absorption spectrum measured with the dichloromethane solution (0.0104 mmol / L) in a quartz cell.

[0564] Furthermore, to measure the emission spectrum, a spectrofluorometer (FP-8600DS model, manufactured by JASCO Corporation) was used. Under a nitrogen atmosphere, a dichloromethane deoxygenated solution (0.0104 mmol / L) was placed in a quartz cell in a glove box (LABstar M13 (1250 / 780), manufactured by Bright Co., Ltd.), sealed tightly, and the measurement was performed at room temperature.

[0565] Furthermore, to measure the emission quantum yield, an absolute PL quantum yield analyzer (Hamamatsu Photonics Ltd., C11347-01) was used. In a glove box (Bright Co., Ltd., LABstar M13 (1250 / 780)), a dichloromethane deoxygenated solution (0.0104 mmol / L) was placed in a quartz cell under a nitrogen atmosphere, sealed tightly, and measured at room temperature. Ir(5iBu4mppy-d5)2(4mmtBup5mppy-d3) excited with light of a wavelength of 400 nm emitted light with an emission quantum yield of 84%. This is extremely high compared to the emission quantum yield of Ir(ppy)2(mbfpypy-d3) of 73%. High luminescence efficiency can be expected by using Ir(5iBu4mppy-d5)2(4mmtBup5mppy-d3) in a light-emitting device. [Examples]

[0566] In this embodiment, a light-emitting device 1, a light-emitting device 2, and a light-emitting device 3 according to one aspect of the present invention will be described with reference to Figures 25 to 32.

[0567] Figure 25 is a diagram illustrating the configuration of the light-emitting device 550X.

[0568] Figure 26 illustrates the current density-luminance characteristics of light-emitting device 1, light-emitting device 2, and light-emitting device 3.

[0569] Figure 27 illustrates the luminance-current efficiency characteristics of light-emitting device 1, light-emitting device 2, and light-emitting device 3.

[0570] Figure 28 illustrates the voltage-luminance characteristics of light-emitting device 1, light-emitting device 2, and light-emitting device 3.

[0571] Figure 29 illustrates the voltage-current characteristics of light-emitting device 1, light-emitting device 2, and light-emitting device 3.

[0572] Figure 30 illustrates the luminance-external quantum efficiency characteristics of light-emitting devices 1, 2, and 3. The external quantum efficiency was calculated from the luminance, assuming that the light distribution characteristics of the light-emitting devices are Lambertsian.

[0573] Figure 31 shows light-emitting devices 1, 2, and 3 at 1000 cd / m². 2 This diagram illustrates the emission spectrum when the light source is emitted at a specific brightness level.

[0574] Figure 32 shows a constant current density (50 mA / cm²). 2 This figure illustrates the change over time in the normalized brightness of light-emitting devices 1, 2, and 3 when they are illuminated using ).

[0575] <Light-emitting device 1> The light-emitting device 1 described in this embodiment has the same configuration as the light-emitting device 550X (see Figure 25).

[0576] The light-emitting device 1 has an electrode 551X, an electrode 552X, and a unit 103X. The unit 103X is sandwiched between the electrodes 551X and 552X, and the unit 103X contains an organic compound according to one aspect of the present invention, {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)).

[0577] Configuration of Light-Emitting Device 1 Table 1 shows the configuration of the light-emitting device 1. The structural formulas of the materials used in the light-emitting device described in this embodiment are shown below. In the table of this embodiment, subscripts and superscripts are written in standard size for convenience. For example, subscripts used in abbreviations and superscripts used in units are written in standard size in the table. These descriptions in the table can be interpreted with reference to the description in the specification.

[0578] [Table 1]

[0579] [ka]

[0580] 《Method for fabricating light-emitting device 1》 The light-emitting device 1 described in this embodiment was fabricated using a method comprising the following steps.

[0581] [Step 1] In the first step, electrode 551X was formed. Specifically, it was formed by sputtering using indium tin oxide (ITSO), which contains silicon or silicon oxide, as the target.

[0582] The electrode 551X contains ITSO and has a thickness of 70 nm and 4 mm 2 It has an area of ​​(2mm x 2mm).

[0583] Next, the substrate on which the electrode 551X was formed was washed with water, fired at 200°C for 1 hour, and then subjected to UV ozone treatment for 370 seconds. -4 The substrate was introduced into a vacuum deposition apparatus where the internal pressure was reduced to approximately Pa, and vacuum firing was performed at 170°C for 30 minutes in the heating chamber within the vacuum deposition apparatus. After that, the substrate was allowed to cool for about 30 minutes.

[0584] [Step 2] In the second step, layer 104 was formed on electrode 551X. Specifically, the material was co-deposited using resistance heating.

[0585] Layer 104 contains N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviated as PCBBiF) and an electron acceptor material (abbreviated as OCHD-003) in a weight ratio of PCBBiF:OCHD-003 = 1:0.03, and has a thickness of 10 nm. OCHD-003 contains fluorine and has a molecular weight of 672.

[0586] [Step 3] In the third step, layer 112_1 was formed on layer 104. Specifically, the material was deposited using the resistance heating method.

[0587] Layer 112_1 contains PCBBiF and has a thickness of 40 nm.

[0588] [Step 4] In the fourth step, layer 112_2 was formed on layer 112_1. Specifically, the material was deposited using the resistance heating method.

[0589] Layer 112_2 contains 4,4'-diphenyl-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCBBi1BP) and has a thickness of 10 nm.

[0590] [Step 5] In the fifth step, layer 111X was formed on layer 112_2. Specifically, the material was co-deposited using the resistance heating method.

[0591] Layer 111X contains 8-(1,1'-biphenyl-4-yl)-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofl[3,2-d]pyrimidine (abbreviated as 8BP-4mDBtPBfpm), 9,9'-diphenyl-9H,9'H-3,3'-bicarbazole (abbreviated as PCCP), and {2-[5-(methyl-d3)-4-phenyl-2-pyridinyl-κN]phenyl-κC}bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviated as Ir(ppy)2(5m4dppy-d3)) in a weight ratio of 8BP-4mDBtPBfpm:PCCP:Ir(ppy)2(5m4dppy-d3) = 0.5:0.5:0.1 and has a thickness of 40 nm.

[0592] [Step 6] In the sixth step, layer 113_1 was formed on layer 111X. Specifically, the material was deposited using the resistance heating method.

[0593] Layer 113_1 contains 8BP-4mDBtPBfpm and has a thickness of 10 nm.

[0594] [Step 7] In the seventh step, layer 113_2 was formed on layer 113_1. Specifically, the material was deposited using the resistance heating method.

[0595] Layer 113_2 contains 2,9-di(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviated as NBPhen) and has a thickness of 20 nm.

[0596] [Step 8] In the eighth step, layer 105 was formed on layer 113_2. Specifically, the material was deposited using the resistance heating method.

[0597] Layer 105 contains lithium fluoride (abbreviated as LiF) and has a thickness of 1 nm.

[0598] [Step 9] In the ninth step, electrode 552X was formed on layer 105. Specifically, the material was deposited using resistance heating.

[0599] The electrode 552X contains aluminum (abbreviated as Al) and has a thickness of 200 nm.

[0600] Operating characteristics of the light-emitting device 1 When power was supplied, the light-emitting device 1 emitted light EL1 (see Figure 25). The operating characteristics of the light-emitting device 1 were measured at room temperature (see Figures 26 to 31). A spectroradiometer (Topcon SR-UL1R) was used to measure luminance, CIE chromaticity, and emission spectrum.

[0601] The fabricated light-emitting device has a brightness of 1000 cd / m². 2 Table 2 shows the main initial characteristics when the light-emitting device is activated at a certain current density (50 mA / cm²). 2 Table 3 shows the LT90, which is the time elapsed until the brightness decreases to 90% of the initial brightness after the device is made to emit light. The characteristics of other light-emitting devices, whose configuration will be described later, are also shown in Tables 2 and 3.

[0602] [Table 2]

[0603] [Table 3]

[0604] Light-emitting device 1 was found to exhibit good characteristics. For example, light-emitting device 1 had superior reliability compared to comparison device 1. Furthermore, light-emitting device 1 achieved a brightness of 1000 cd / m². 2This was achieved at a lower voltage compared to comparative device 1. Furthermore, light-emitting device 1 exhibited higher external quantum efficiency compared to comparative device 1. Reducing the driving voltage and improving the external quantum efficiency have the effect of improving the energy efficiency of converting power into light. In addition, the light emitted by light-emitting device 1 includes light with shorter wavelengths compared to the light emitted by comparative device 1. For example, by using Ir(ppy)2(5m4dppy-d3) in layer 111X together with a fluorescent light-emitting material with a green emission color, it is expected that energy can be efficiently transferred to the fluorescent light-emitting material. Furthermore, it is expected that light emission can be obtained with high efficiency.

[0605] <Light-emitting device 2> The light-emitting device 2 fabricated in this embodiment has the same configuration as the light-emitting device 550X (see Figure 25). The configuration of light-emitting device 2 differs from that of light-emitting device 1 in layer 111X. Specifically, layer 111X differs from light-emitting device 1 in that it contains 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)) instead of Ir(ppy)2(5m4dppy-d3). The structural formula of Ir(5m4dppy-d3)2(ppy) is shown below.

[0606] [ka]

[0607] 《Method for fabricating light-emitting device 2》 The light-emitting device 2 described in this embodiment was fabricated using a method comprising the following steps.

[0608] [Step 5] In the fifth step, layer 111X was formed on layer 112_2. Specifically, the material was co-deposited using the resistance heating method.

[0609] Layer 111X contains 8BP-4mDBtPBfpm, PCCP, and Ir(5m4dppy-d3)2(ppy) in a weight ratio of 8BP-4mDBtPBfpm:PCCP:Ir(5m4dppy-d3)2(ppy) = 0.5:0.5:0.1, and has a thickness of 40 nm.

[0610] Operating characteristics of the light-emitting device 2 When power was supplied, the light-emitting device 2 emitted light EL1 (see Figure 25). The operating characteristics of the light-emitting device 2 were measured at room temperature (see Figures 26 to 31).

[0611] The fabricated light-emitting device has a brightness of 1000 cd / m². 2 Table 2 shows the main initial characteristics when the light-emitting device is activated at a certain current density (50 mA / cm²). 2 Table 3 shows the LT90, which is the elapsed time until the brightness decreases to 90% of the initial brightness when the device is lit.

[0612] Light-emitting device 2 was found to exhibit good characteristics. For example, light-emitting device 2 had superior reliability compared to comparison device 1. Furthermore, light-emitting device 2 also had superior reliability compared to light-emitting device 1. Note that Ir(5m4dppy-d3)2(ppy) has a larger number of ligands containing deuterated alkyl groups compared to Ir(ppy)2(5m4dppy-d3). In other words, it has fewer ligands that do not contain deuterated alkyl groups. Also, light-emitting device 2 had a brightness of 1000 cd / m². 2 This was achieved at a lower voltage compared to comparative device 1. Furthermore, light-emitting device 2 showed higher external quantum efficiency compared to comparative device 1. Reducing the driving voltage and improving the external quantum efficiency have the effect of improving the energy efficiency of converting power into light. In addition, the light emitted by light-emitting device 2 includes light with shorter wavelengths compared to the light emitted by comparative device 1. For example, by using Ir(5m4dppy-d3)2(ppy) in layer 111X together with a fluorescent light-emitting material that emits green light, it is expected that energy can be efficiently transferred to the fluorescent light-emitting material. Furthermore, it is expected that light emission can be obtained with high efficiency.

[0613] <Light-emitting device 3> The light-emitting device 3 fabricated in this embodiment has the same configuration as the light-emitting device 550X (see Figure 25). The configuration of light-emitting device 3 differs from that of light-emitting device 1 in layer 111X. Specifically, layer 111X differs from light-emitting device 1 in that it contains {2-[4-(3,5-di-tert-butylphenyl)-5-(methyl-d3)-2-pyridinyl-κN]phenyl-κC}bis{2-[4-(methyl-d3)-5-(2-methylpropyl-1,1-d2)-2-pyridinyl-κN]phenyl-κC}iridium(III) (abbreviation: Ir(5iBu4mppy-d5)2(4mmtBup5mppy-d3)) instead of Ir(ppy)2(5m4dppy-d3). The structural formula of Ir(5iBu4mppy-d5)2(4mmtBup5mppy-d3) is shown below.

[0614] [ka]

[0615] 《Method for fabricating light-emitting device 3》 The light-emitting device 3 described in this embodiment was fabricated using a method comprising the following steps.

[0616] [Step 5] In the fifth step, layer 111X was formed on layer 112_2. Specifically, the material was co-deposited using the resistance heating method.

[0617] Layer 111X contains 8BP-4mDBtPBfpm, PCCP, and Ir(5iBu4mppy-d5)2(4mmtBup5mppy-d3) in a weight ratio of 8BP-4mDBtPBfpm:PCCP:Ir(5iBu4mppy-d5)2(4mmtBup5mppy-d3) = 0.5:0.5:0.1, and has a thickness of 40 nm.

[0618] Operating characteristics of the light-emitting device 3 When power was supplied, the light-emitting device 3 emitted light EL1 (see Figure 25). The operating characteristics of the light-emitting device 3 were measured at room temperature (see Figures 26 to 31).

[0619] The fabricated light-emitting device has a brightness of 1000 cd / m². 2 Table 2 shows the main initial characteristics when the light-emitting device is activated at a certain current density (50 mA / cm²). 2 Table 3 shows the LT90, which is the elapsed time until the brightness decreases to 90% of the initial brightness when the device is lit.

[0620] The light-emitting device 3 was found to exhibit good characteristics. For example, the light-emitting device 3 had superior reliability compared to the comparative device 1. In addition, the light emitted by the light-emitting device 3 includes light with shorter wavelengths compared to the light emitted by the comparative device 1. For example, by using Ir(5iBu4mppy-d5)2(4mmtBup5mppy-d3) in layer 111X together with a fluorescent light-emitting material that emits green light, it is expected that energy can be efficiently transferred to the fluorescent light-emitting material. Furthermore, it is expected that light emission can be obtained with high efficiency.

[0621] (Reference example 1) The comparative device 1 fabricated in this example has the same configuration as the light-emitting device 550X (see Figure 25).

[0622] Configuration of Comparison Device 1 Comparative device 1 differs from light-emitting device 1 in that it uses [2-d3-methyl-(2-pyridinyl-κN)benzofl[2,3-b]pyridine-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(ppy)2(mbfpypy-d3)) instead of Ir(ppy)2(5m4dppy-d3). The structural formula of Ir(ppy)2(mbfpypy-d3) is shown below.

[0623] [ka]

[0624] 《Method for fabricating comparative device 1》 Comparative device 1, described in this reference example, was fabricated using a method comprising the steps outlined below. Note that the fabrication method for comparative device 1 differs from that of light-emitting device 1 in that, in the step of forming layer 111X, Ir(ppy)2(mbfpypy-d3) was used instead of Ir(ppy)2(5m4dppy-d3). Here, the differences will be explained in detail, and the parts using the same method will refer to the explanation above.

[0625] [Step 5] In the fifth step, layer 111X was formed on layer 112_2. Specifically, the material was co-deposited using the resistance heating method.

[0626] Layer 111X contains 8BP-4mDBtPBfpm, PCCP, and Ir(ppy)2(mbfpypy-d3) in a weight ratio of 8BP-4mDBtPBfpm:PCCP:Ir(ppy)2(mbfpypy-d3) = 0.5:0.5:0.1 and has a thickness of 40 nm. [Examples]

[0627] In this example, the results of calculating the molecular orbitals of the organic compound will be explained with reference to Figure 33.

[0628] Figure 33(A) illustrates the results of calculating the LUMO of an organic compound in its singlet ground state. Figure 33(B) illustrates the results of calculating the spin density of an organic compound in its triplet excited state.

[0629] The molecular orbitals were calculated for organic compounds having the structure shown below.

[0630] [ka]

[0631] In organic compounds, the meta position of the pyridine ring coordinating to iridium showed a high spin density in the triplet excited state (see Figure 33(B)). Furthermore, the organic compound having the above structure is an example of an organic compound represented by general formula (G0), and the LUMO distribution was concentrated at the meta position of the pyridine ring coordinating to iridium (see Figure 33(A)).

[0632] The Gaussian09 program was used for molecular orbital calculations. The B3PW91 functional was used, LANL2DZ was used as the basis set for Ir, and 6-311G(d,p) was used as the basis set for the other atoms. Furthermore, structural optimization was performed for the singlet ground state (S0) and the triplet excited state (T1). [Explanation of Symbols]

[0633] ANO conductive film C21 capacity C22 capacity 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 Hikari ELY Hikari 103S Unit 103X Unit 103Y Unit 104S layer 104X layer 104XY area 104Y layer 104 layers 105S layer 105X layer 105Y layer 105 layers 106_1 layer 106_2 layers 106_3 layers 106 layers 111X layer 111Y layer 112_1 layer 112_2 layer 112S layer 112X layer 112 layers 113_1 layer 113_2 layer 113S layer 113X layer 113 layers 114N layer 114P layer 114S layer 231 areas 400 circuit boards 401 First electrode 403 EL layer 404 Second electrode 405 sealant 406 Sealant 407 Sealing substrate 412 pads 420 IC chips 510 circuit board 519B terminal 520T area 520 Functional Layers 521 Insulating film 528 Insulating film 529_1 Membrane 529_2 Membrane 529_3 Membrane 530X pixel circuit 540 Functional Layers 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 Drive Circuit 602 pixel section 603 Gate wire drive circuit 604 Sealing substrate 605 Sealant 607 Space 608 Wiring 609 External input terminal 610 element substrate 611 Switching FET 612 Current-Controlled FET 613 First electrode 614 Insulators 616 EL layer 617 Second electrode 618 Light-emitting devices 623 FET 700 Display device 702X pixels 703 pixels 951 circuit board 952 Electrode 953 Insulating layer 954 Partition layer 955 EL layer 956 Electrode 1001 circuit board 1002 Underlying insulating film 1003 Gate Insulator 10:06 Guard Station 1007 🙏 1008 Gate 1020 First interlayer insulating film 1021 Second interlayer insulating film 1022 Electrode 1024B Electrode 1024G electrode 1024R electrode 1024W electrode 1025 Bulkhead 1028 EL layer 1029 Electrode 1031 Sealing substrate 1032 Sealant 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 section 1041 Drive circuit section 1042 Peripheral area 2001 cabinet 2002 light source 2100 Robots 2102 Microphone 2103 Top Camera 2104 Speaker 2105 Display 2106 Lower Camera 2107 Obstacle Sensor 2108 Moving mechanism 2110 Arithmetic equipment 3001 Lighting device 5000 cabinets 5001 Display section 5002 Display section 5003 Speaker 5004 LED Lamp 5006 Connection terminal 5007 Sensor 5008 Microphone 5012 Support part 5013 Earphones 5100 Cleaning Robot 5101 Display 5102 Camera 5103 Brush 5104 Operation Buttons 5120 Garbage 5140 Portable electronic devices 5200 display area 5201 Display area 5202 Display area 5203 Display area 7101 enclosure 7103 Display section 7105 Stand 7107 Display section 7109 Operation Keys 7110 Remote Control Unit 7201 Main Unit 7202 enclosure 7203 Display section 7204 Keyboard 7205 External connection port 7206 Pointing device 7210 Second display unit 7401 enclosure 7402 Display section 7403 Operation Buttons 7404 External connection port 7405 Speaker 7406 Microphone 9310 Mobile Information Terminal 9311 Display Panel 9313 Hinge 9315 enclosure

Claims

1. An organic compound represented by general formula (G0): 【Chemistry 1】 (However, in the general formula (G0), R １０１ ~R １１１ are each independently hydrogen or an alkyl group having 1 to 6 carbon atoms, n is 1 or 2, and L is a ligand represented by the following general formula (L0), in which R ２０１ ~R ２０８ are each independently hydrogen, deuterium, or an alkyl group having 1 to 6 carbon atoms, and some or all of the hydrogen atoms in the alkyl group may be deuterated. 【Chemistry 2】

2. An organic compound represented by general formula (G1-1): 【Transformation 3】 (In the general formula (G1-1), n ​​is 1 or 2, and L is a ligand represented by the following general formula (L0), and in the general formula (L0), R ２０１ ~R ２０８ are each independently hydrogen, deuterium, or an alkyl group having 1 to 6 carbon atoms, and some or all of the hydrogen atoms in the alkyl group may be deuterated. 【Chemistry 4】

3. An organic compound represented by general formula (G1-2): 【Transformation 5】 (In the general formula (G1-2), n is 1 or 2, and L is a ligand represented by the following general formula (L0), and in the general formula (L0), R ２０１ ~R ２０８ are each independently hydrogen, deuterium, or an alkyl group having 1 to 6 carbon atoms, and some or all of the hydrogen atoms in the alkyl group may be deuterated. 【Transformation 6】

4. In claim 3, The ligand is an organic compound having an alkyl group in which one or more hydrogen atoms are deuterated.

5. In any one of claims 1 to 3, The ligand is an organic compound represented by structural formula (L1-1). 【Transformation 7】

6. In any one of claims 1 to 3, The ligand is an organic compound represented by structural formula (L1-2). 【Transformation 8】

7. a first electrode; a second electrode; and a first unit; the first unit is located between the first electrode and the second electrode; A light-emitting device, wherein the first unit comprises the organic compound according to claim 1 .

8. a first light emitting device; and a second light-emitting device; the first light-emitting device has a first electrode, a second electrode, a first unit, and a first layer; the first unit is located between the first electrode and the second electrode; the first layer is located between the first unit and the first electrode; The first unit includes the organic compound according to any one of claims 1 to 4, the first layer includes a second organic compound including a halogen group or a cyano group or a transition metal oxide; the second light emitting device is adjacent to the first light emitting device; the second light-emitting device has a third electrode, a fourth electrode, a second unit, and a second layer; a gap between the third electrode and the first electrode; the second unit is located between the third electrode and the fourth electrode; the second layer is located between the second unit and the third electrode; the second unit includes a light-emitting material; the second layer contains the second organic compound or the transition metal oxide; a region between the second layer and the first layer that is thinner than the first layer; The display device, wherein the region overlaps the gap.

9. A display device comprising the light-emitting device according to claim 7 and a transistor or a substrate.

10. An electronic device comprising the display device according to claim 9, and a sensor, an operation button, a speaker, or a microphone.

11. A light-emitting apparatus comprising the light-emitting device according to claim 7 and a transistor or a substrate.

12. A lighting device comprising the light-emitting device according to claim 11 and a housing.

Images