Organic compounds, light-emitting devices, light-emitting apparatus, electronic devices, display devices, lighting apparatus

Abstract

Provided is a novel organic compound. Also provided is an organic compound that emits light having good chromaticity. Also provided is an organic compound that emits blue light having good chromaticity. Also provided is a light-emitting element having good luminous efficiency. Also provided is an organic compound having high carrier transport properties. This organic compound has one of a substituted or unsubstituted dibenzofurobisbenzofuran skeleton, a substituted or unsubstituted dibenzothienobisbenzothiophene skeleton, a substituted or unsubstituted benzobisbenzothienobenzofuran skeleton or a substituted or unsubstituted dibenzothienobisbenzofuran skeleton, and has one or two amino groups. In addition, this organic compound is such that the amino group has a substituted or unsubstituted heteroaryl group and any one of a substituted or unsubstituted aromatic hydrocarbon group having 6-25 carbon atoms or a substituted or unsubstituted heteroaryl group having 5-25 carbon atoms.

Description

Technical Field

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

[0002] Note that one aspect of the present invention is not limited to the above technical field. The technical field of one aspect of the invention disclosed in this specification and the like relates to an article, a method, or a manufacturing method. Or, one aspect of the present invention relates to a process, a machine, a manufacture, or a composition of matter. Therefore, more specifically, as the technical field of one aspect of the present invention disclosed in this specification, semiconductor devices, display devices, light-emitting devices, power storage devices, storage devices, their driving methods, or their manufacturing methods can be cited as an example.

Background Art

[0003] Display devices and light-emitting devices using organic EL elements have been partially put into practical use, and their applications are spreading. These days, as liquid crystal displays have made great progress, organic EL displays, which are said to be the next-generation displays, are naturally required to have high quality.

[0004] As materials for organic EL displays, various substances have been developed, but there are not so many substances having characteristics that can withstand practical use. Also, considering the diversity of combinations and compatibility, it is certain that the more options there are, the more convenient it is.

[0005] An organic EL element has a function-separated configuration in which a plurality of functions are assigned to different substances. Among them, there are great demands for the light-emitting material, particularly the luminous efficiency that affects power consumption, and the emission color for improving display quality.

[0006] For example, an organic compound having at least one amino group to which any one of a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group is bonded to any one of a substituted or unsubstituted naphthobisbenzofuran, a substituted or unsubstituted naphthobisbenzothiophene skeleton, and a substituted or unsubstituted naphthobenzofuranobenzothiophene skeleton is known (Patent Document 1).

Prior Art Documents

Patent Documents

[0007]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0008] One aspect of the present invention is to provide a novel organic compound excellent in convenience, usefulness, or reliability as one of the problems. Or, to provide a novel light-emitting device excellent in convenience, usefulness, or reliability as one of the problems. Or, to provide a novel photoelectric conversion device excellent in convenience, usefulness, or reliability as one of the problems. Or, to provide a novel electronic device excellent in convenience, usefulness, or reliability as one of the problems. Or, to provide a novel display device excellent in convenience, usefulness, or reliability as one of the problems. Or, to provide a novel lighting device excellent in convenience, usefulness, or reliability as one of the problems. Or, to provide a novel organic compound, a novel light-emitting device, a novel light-emitting device, a novel electronic device, a novel display device, a novel lighting device, or a novel semiconductor device as one of the problems.

[0009] Note that the description of these problems does not preclude the existence of other problems. Note that one aspect of the present invention does not necessarily need to solve all of these problems. Other problems will become apparent from the description in the specification, drawings, claims, etc., and it is possible to extract these other problems from the description in the specification, drawings, claims, etc.

Means for Solving the Problems

[0010] (1) One aspect of the present invention is an organic compound represented by the following general formula (G0).

[0011]

Chemical Formula

[0012] In the above general formula (G0), B represents any one of a substituted or unsubstituted dibenzofluorobisbenzofuran skeleton, a substituted or unsubstituted dibenzothienobisbenzothiophene skeleton, a substituted or unsubstituted benzobisbenzothienobenzofuran skeleton, or a substituted or unsubstituted dibenzothienobisbenzofuran skeleton.

[0013] Also, q represents an integer of 1 or 2, and when q is 2, a set of HAs may be the same as or different from each other.

[0014] HA is an amino group represented by the above general formula (R0) or an aryl group having an amino group. In the above general formula (R0), α 1 and α 2 each independently represent a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 carbon atoms.

[0015] Also, A represents a substituted or unsubstituted heteroaryl group, Ar 1 represents either a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 25 carbon atoms, and m and n each independently represent an integer of 0 or 1.

[0016] (2) Further, one aspect of the present invention is an organic compound represented by the following general formula (G1).

[0017] [Chemical formula]

[0018] In the above general formula (G1), X 1 to X 3 represents oxygen or sulfur, and X 1 to X 3 may be the same as or different from each other.

[0019] Also, one or two of R 11 to R 22 are an amino group represented by the above general formula (R0) or an aryl group having an amino group, and R 11 to R 22 except for the one or two are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an alicyclic hydrocarbon group having 3 to 6 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 13 carbon atoms. Incidentally, when two of R 11 to R 22 are an amino group represented by the above general formula (R0) or an aryl group having an amino group, the pair of amino groups or aryl groups having an amino group represented by the above general formula (R0) may be the same as or different from each other.

[0020] In the above general formula (R0), α 1 and α 2 each independently represent a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 carbon atoms.

[0021] Also, A represents a substituted or unsubstituted heteroaryl group, and Ar 1represents either a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 25 carbon atoms. Note that m and n each independently represent an integer of 0 or 1.

[0022] (3) Also, in one aspect of the present invention, in the general formula (G1), R 12 and R 16 are an amino group represented by the general formula (R0) or an aryl group having an amino group, and are organic compounds. Note that a pair of the amino group represented by the general formula (R0) or the aryl group having an amino group may be the same as or different from each other.

[0023] (4) Also, in one aspect of the present invention, in the general formula (R0), A is an organic compound having a five-membered ring, and the five-membered ring contains a heteroatom.

[0024] (5) Also, in one aspect of the present invention, in the general formula (R0), A represents a heteroaryl group having a carbazole skeleton, a dibenzofuran skeleton, or a dibenzothiophene skeleton, and is an organic compound.

[0025] Also, Ar 1 represents a substituent having a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a carbazole skeleton, a dibenzofuran skeleton, or a dibenzothiophene skeleton.

[0026] (6) Also, in one aspect of the present invention, the amino group represented by the general formula (R0) or the aryl group having an amino group is an organic compound represented by the following general formula (R1).

[0027]

Chemical formula

[0028] Note that in the general formula (R1), R 31 to R 42each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, an alicyclic hydrocarbon group having 3 to 6 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 13 carbon atoms.

[0029] (7) Further, one aspect of the present invention is an organic compound in which the amino group represented by the general formula (R0) or the aryl group having an amino group is the following general formula (R2).

[0030] [Chemical formula]

[0031] In the above general formula (R2), R 51 to R 67 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, an alicyclic hydrocarbon group having 3 to 6 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 13 carbon atoms.

[0032] Thereby, a novel light-emitting material having a high photoluminescence quantum yield can be provided. Or, a novel light-emitting material having a high molar extinction coefficient can be provided. Or, a novel light-emitting material that exhibits sharp blue in the emission spectrum can be provided.

[0033] (8) Further, one aspect of the present invention is a light-emitting device having a first electrode, a second electrode, and a unit. The second electrode includes a region overlapping with the first electrode. The unit includes a region sandwiched between the first electrode and the second electrode, and the unit contains the above compound.

[0034] Thereby, a blue light-emitting element with high color purity can be provided. Or, a light-emitting element with high external quantum efficiency can be provided. Or, a light-emitting element with good emission lifetime can be provided. Or, a light-emitting element with low efficiency dopant concentration dependence can be provided. As a result, a novel light-emitting device with good characteristics and high industrial productivity can be provided.

[0035] (9) Further, one aspect of the present invention is a light-emitting device including the above-described light-emitting device and a transistor or a substrate.

[0036] (10) Further, one aspect of the present invention is a display device including the above-described light-emitting device and a transistor or a substrate.

[0037] (11) Further, one aspect of the present invention is a lighting device including the above-described light-emitting device and a housing.

[0038] (12) Further, one aspect of the present invention is an electronic device including the above-described display device and a sensor, an operation button, a speaker, or a microphone.

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

[0040] Note that the light-emitting device in this specification includes an image display device using a light-emitting element. Further, a module in which a connector, for example, an anisotropic conductive film or a TCP (Tape Carrier Package), is attached to the light-emitting element, a module in which a printed wiring board is provided at the tip of the TCP, or a module in which an IC (integrated circuit) is directly mounted on the light-emitting element by a COG (Chip On Glass) method may also be included in the light-emitting device. Furthermore, lighting fixtures and the like may have a light-emitting device.

Advantages of the Invention

[0041] According to one aspect of the present invention, it is possible to provide a novel organic compound excellent in convenience, usefulness, or reliability. Or, it is possible to provide a novel light-emitting device excellent in convenience, usefulness, or reliability. Or, one of the problems is to provide a novel photoelectric conversion device excellent in convenience, usefulness, or reliability. Or, it is possible to provide a novel light-emitting device excellent in convenience, usefulness, or reliability. Or, it is possible to provide a novel electronic device excellent in convenience, usefulness, or reliability. Or, it is possible to provide a novel display device excellent in convenience, usefulness, or reliability. Or, it is possible to provide a novel lighting device excellent in convenience, usefulness, or reliability. Or, it is possible to provide a novel organic compound, a novel light-emitting device, a novel light-emitting device, a novel electronic device, a novel display device, a novel lighting device, or a novel semiconductor device.

[0042] Note that the description of these effects does not prevent the existence of other effects. Note that one aspect of the present invention does not necessarily have to have all of these effects. Note that other effects will be apparent from the description in the specification, drawings, claims, etc., and it is possible to extract these other effects from the description in the specification, drawings, claims, etc.

Brief Description of Drawings

[0043] FIGS. 1A and 1B are diagrams for explaining the configuration of a light-emitting device according to an embodiment. FIGS. 2A and 2B are diagrams for explaining the configuration of a light-emitting device according to an embodiment. FIG. 3A is a diagram for explaining the configuration of a light-emitting panel according to an embodiment, and FIG. 3B is a diagram for explaining the configuration of a photoelectric conversion device according to an embodiment. FIGS. 4A and 4B are conceptual diagrams of an active matrix light-emitting device. FIGS. 5A and 5B are conceptual diagrams of an active matrix light-emitting device. FIG. 6 is a conceptual diagram of an active matrix light-emitting device. FIGS. 7A and 7B are conceptual diagrams of a passive matrix light-emitting device. Figures 8A and 8B are diagrams showing a lighting device. Figures 9A, 9B1, 9B2, and 9C are diagrams showing an electronic device. Figures 10A to 10C are diagrams showing an electronic device. Figure 11 is a diagram showing a lighting device. Figure 12 is a diagram showing a lighting device. Figure 13 is a diagram showing an in-vehicle display device and a lighting device. Figures 14A to 14C are diagrams showing an electronic device. Figure 15 is a diagram showing an absorption spectrum and an emission spectrum in a toluene solution of PCA2Dfbf-02. Figure 16 is a diagram showing an absorption spectrum and an emission spectrum in a thin film state of PCA2Dfbf-02. Figures 17A and 17B are diagrams showing the 1 1H NMR spectrum of PCA2Dfbf-02. Figure 18 is a diagram showing an absorption spectrum and an emission spectrum in a toluene solution of FrA2Dfbf-02. Figure 19 is a diagram showing an absorption spectrum and an emission spectrum in a thin film state of FrA2Dfbf-02. Figures 20A and 20B are diagrams showing the 1 1H NMR spectrum of FrA2Dfbf-02. Figure 21 is a diagram showing an absorption spectrum and an emission spectrum in a toluene solution of tBuFrA2Dfbf-02. Figure 22 is a diagram showing an absorption spectrum and an emission spectrum in a thin film state of tBuFrA2Dfbf-02. Figures 23A and 23B are diagrams showing the 1 1H NMR spectrum of tBuFrA2Dfbf-02. Figure 24 is a diagram for explaining the configuration of a light-emitting device according to an example. Figure 25 is a diagram for explaining the current density-luminance characteristics of a light-emitting device according to an example. Figure 26 is a diagram for explaining the luminance-current efficiency characteristics of a light-emitting device according to an example. FIG. 27 is a diagram for explaining the voltage-luminance characteristics of the light-emitting device according to the embodiment. FIG. 28 is a diagram for explaining the voltage-current characteristics of the light-emitting device according to the embodiment. FIG. 29 is a diagram for explaining the luminance-external quantum efficiency characteristics of the light-emitting device according to the embodiment. FIG. 30 is a diagram for explaining the emission spectrum of the light-emitting device according to the embodiment. FIG. 31 is a diagram for explaining the characteristics of the light-emitting device according to the embodiment. FIG. 32 is a diagram for explaining the current density-luminance characteristics of the light-emitting device according to the embodiment. FIG. 33 is a diagram for explaining the luminance-current efficiency characteristics of the light-emitting device according to the embodiment. FIG. 34 is a diagram for explaining the voltage-luminance characteristics of the light-emitting device according to the embodiment. FIG. 35 is a diagram for explaining the voltage-current characteristics of the light-emitting device according to the embodiment. FIG. 36 is a diagram for explaining the luminance-external quantum efficiency characteristics of the light-emitting device according to the embodiment. FIG. 37 is a diagram for explaining the emission spectrum of the light-emitting device according to the embodiment. FIG. 38 is a diagram for explaining the time change of the normalized luminance of the light-emitting device according to the embodiment. FIG. 39 is a diagram for explaining the current density-luminance characteristics of the light-emitting device according to the embodiment. FIG. 40 is a diagram for explaining the luminance-current efficiency characteristics of the light-emitting device according to the embodiment. FIG. 41 is a diagram for explaining the voltage-luminance characteristics of the light-emitting device according to the embodiment. FIG. 42 is a diagram for explaining the voltage-current characteristics of the light-emitting device according to the embodiment. FIG. 43 is a diagram for explaining the luminance-external quantum efficiency characteristics of the light-emitting device according to the embodiment. FIG. 44 is a diagram for explaining the emission spectrum of the light-emitting device according to the embodiment. FIG. 45 is a diagram for explaining the current density-luminance characteristics of the light-emitting device according to the embodiment. FIG. 46 is a diagram for explaining the luminance-current efficiency characteristics of the light-emitting device according to the embodiment. FIG. 47 is a diagram for explaining the voltage-luminance characteristics of the light-emitting device according to the embodiment. FIG. 48 is a diagram for explaining the voltage-current characteristics of the light-emitting device according to the embodiment. FIG. 49 is a diagram for explaining the luminance-external quantum efficiency characteristics of the light-emitting device according to the embodiment. FIG. 50 is a diagram for explaining the emission spectrum of the light-emitting device according to the embodiment. FIG. 51 is a diagram showing the absorption spectrum and emission spectrum of mmtBuPCA2Dfbf-02 in a toluene solution. FIG. 52 is a diagram showing the absorption spectrum and emission spectrum of mmtBuPCA2Dfbf-02 in a thin film state. FIGS. 53A and 53B are diagrams showing the 1 1H NMR spectrum of mmtBuPCA2Dfbf-02. FIG. 54 is a diagram for explaining the current density-luminance characteristics of the light-emitting device according to the embodiment. FIG. 55 is a diagram for explaining the luminance-current efficiency characteristics of the light-emitting device according to the embodiment. FIG. 56 is a diagram for explaining the voltage-luminance characteristics of the light-emitting device according to the embodiment. FIG. 57 is a diagram for explaining the voltage-current characteristics of the light-emitting device according to the embodiment. FIG. 58 is a diagram for explaining the luminance-external quantum efficiency characteristics of the light-emitting device according to the embodiment. FIG. 59 is a diagram for explaining the emission spectrum of the light-emitting device according to the embodiment. FIG. 60 is a diagram for explaining the time change of the normalized luminance of the light-emitting device according to the embodiment.

MODE FOR CARRYING OUT THE INVENTION

[0044] The organic compound of one aspect of the present invention has either a substituted or unsubstituted dibenzofluorobisbenzofuran skeleton, a substituted or unsubstituted dibenzothienobisbenzothiophene skeleton, a substituted or unsubstituted benzobisbenzothienobenzofuran skeleton, or a substituted or unsubstituted dibenzothienobisbenzofuran skeleton, and has one or two amino groups or an aryl group having an amino group. Further, the amino group includes either a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 25 carbon atoms.

[0045] Thereby, a novel light-emitting material with a high luminescence quantum yield can be provided. Alternatively, a novel light-emitting material with a high molar extinction coefficient can be provided. Alternatively, a novel light-emitting material that exhibits sharp blue in the emission spectrum can be provided. As a result, a novel organic compound excellent in convenience, usefulness, or reliability can be provided.

[0046] The embodiments will be described in detail with reference to the drawings. However, the present invention is not limited to the following description, and it is easily understood by those skilled in the art that the form and details thereof can be variously changed without departing from the spirit and scope of the present invention. Therefore, the present invention is not to be construed as being limited to the description of the embodiments shown below. In the configuration of the invention described below, the same reference numerals are commonly used among different drawings for the same part or parts having the same function, and the repeated description thereof is omitted.

[0047] (Embodiment 1) In the present embodiment, the organic compound of one aspect of the present invention will be described.

[0048] <Example 1 of Organic Compound> The organic compound described in the present embodiment is an organic compound represented by the following general formula (G0).

[0049]

Chemical formula

[0050] "Example of B" In the above general formula (G0), B represents any one of a substituted or unsubstituted dibenzofurobisbenzofuran skeleton, a substituted or unsubstituted dibenzothienobisbenzothiophene skeleton, a substituted or unsubstituted benzobisbenzothienobenzofuran skeleton, or a substituted or unsubstituted dibenzothienobisbenzofuran skeleton.

[0051] The substituted or unsubstituted dibenzofurobisbenzofuran skeleton can be represented, for example, by the following general formula (B11) or the following general formula (B12).

[0052] [Chemical formula]

[0053] Also, the substituted or unsubstituted dibenzothienobisbenzothiophene skeleton can be represented, for example, by the following general formula (B21) or the following general formula (B22). In particular, the dibenzothienobisbenzothiophene skeleton that can be represented by the following general formula (B21) is relatively easy to synthesize and is preferred.

[0054] [Chemical formula]

[0055] Also, the substituted or unsubstituted benzobisbenzothienobenzofuran skeleton can be represented, for example, by the following general formula (B31) or the following general formula (B32).

[0056] [Chemical formula]

[0057] Also, the substituted or unsubstituted dibenzothienobisbenzofuran skeleton can be represented, for example, by the following general formula (B41) or the following general formula (B42).

[0058] [Chemical formula]

[0059] "Examples of q" Also, q represents an integer of 1 or 2. When q is 2, a set of HAs may be the same as or different from each other. In the case where they are the same as each other, they can be easily synthesized. Or, the cost related to synthesis can be reduced.

[0060] "Examples of HA" HA is an amino group represented by the following general formula (R0) or an aryl group having an amino group.

[0061] [Chemical formula]

[0062] "α" 1 and α 2 "Examples of" In the above general formula (R0), α 1 and α 2 each independently represent a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 carbon atoms. Note that m and n each independently represent an integer of 0 or 1. The above general formula (R0) is a secondary amino group when n is 0 and an aryl group having an amino group when n is 1. Also, the organic compound represented by the above general formula (G0) is a tertiary amine.

[0063] Also, for example, in the above general formula (R0), a structure in which m or n is 0 can be used. Thereby, the molecular weight can be reduced and the sublimation temperature can be lowered. Or, in the sublimation purification step or the vapor deposition step, decomposition by heat can be suppressed.

[0064] [Examples of divalent aromatic hydrocarbon group] For example, a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a fluorenylene group, a dimethylfluorenyl group, etc. can be used for α 1 and α 2 It can be used for. In particular, a configuration containing a phenylene group can reduce the molecular weight and lower the sublimation temperature. Or, in the sublimation purification step or the vapor deposition step, thermal decomposition can be suppressed.

[0065] Specifically, groups represented by the following structural formulas (Ar-1) to (Ar-27) can be used. Note that these may further have substituents such as a hydrocarbon group having 1 to 10 carbon atoms, an alicyclic hydrocarbon group having 3 to 10 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms.

[0066] For example, a phenylene group and a group in which several phenylene groups are connected can be used (see (Ar-1) to (Ar-11)). Thereby, it is difficult to extend the conjugation, and the singlet excitation level can be kept high. In particular, a configuration containing a metaphenylene group is preferable because its effect is remarkable. Also, a configuration that is a paraphenylene group can improve the reliability as a light-emitting material.

[0067] [Chemical formula]

[0068] Also, a group in which the substituent is connected by a carbon having a sigma bond such as the 9-position of fluorene can be used (see (Ar-24) to (Ar-27)). Thereby, it is difficult to extend the conjugation, and the singlet excitation level can be kept high. Or, the emission wavelength can be made shorter.

[0069] [Chemical formula]

[0070] [Examples of hydrocarbon groups] For example, examples of hydrocarbon groups having 1 to 10 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tertiary butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, and the like.

[0071] In addition, examples of alicyclic hydrocarbon groups having 3 to 10 carbon atoms include a cyclopropyl group, a cyclohexyl group, and the like.

[0072] In addition, examples of aromatic hydrocarbon groups having 6 to 14 carbon atoms include a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, an anthryl group, a fluorenyl group, and the like. In particular, considering the reduction of synthesis cost, sublimation temperature, and short-wavelength shift of the emission wavelength, a phenyl group is preferable.

[0073] 《Examples of A》 In addition, A represents a substituted or unsubstituted heteroaryl group. For example, a pyridyl group, a furanyl group, a pyrrole skeleton, a furanyl skeleton, a thienyl skeleton, a pyrazole skeleton, an imidazole skeleton, a group having an oxazole skeleton, etc. can be used for A.

[0074] [Examples of Heteroaryl Groups] For example, a carbazolyl group, etc. can be used for A. Specifically, groups represented by the following structural formulas (Ar-50) to (Ar-69) or (Ar-76) to (Ar-97) can be used. Note that these may further have substituents such as a hydrocarbon group having 1 to 10 carbon atoms, an alicyclic hydrocarbon group having 3 to 10 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms.

[0075] Further, for example, a structure having a carbazolyl group and with the 3-position of the carbazolyl group bonded to the nitrogen (amine) of the general formula (R0) can be used for A (see (Ar-51) and (Ar-55)). Or, a structure having a dibenzofuranyl group and with the 2-position of the dibenzofuranyl group bonded to the nitrogen (amine) of the general formula (R0) can be used for A (see (Ar-57)). Or, a structure having a dibenzothiophenyl group and with the 2-position of the dibenzothiophenyl group bonded to the nitrogen (amine) of the general formula (R0) can be used for A (see (Ar-62)). Thereby, the conjugation can be easily extended. Or, the hole transport property can be improved. Or, the emission wavelength can be shifted to a longer wavelength. Or, the reliability can be improved. Among these, the effect is particularly high with the carbazolyl group.

[0076] Further, for example, a structure having a carbazolyl group and with the 2-position of the carbazolyl group bonded to the nitrogen (amine) of the general formula (R0) can be used for A (see (Ar-52)). A structure having a dibenzofuranyl group and with the 3-position of the dibenzofuranyl group bonded to the nitrogen (amine) of the general formula (R0) can be used for A (see (Ar-59)). A structure having a dibenzothiophenyl group and with the 3-position of the dibenzothiophenyl group bonded to the nitrogen (amine) of the general formula (R0) can be used for A (see (Ar-63)). Thereby, the carrier transport property can be improved. Or, an effect of reducing the driving voltage can be expected.

[0077] For example, a dibenzofuranyl group, a dibenzothiophenyl group, or the like can be used for A. Specifically, groups represented by the following structural formulas (Ar-57) to (Ar-67) can be used. Note that these may further have substituents such as a hydrocarbon group having 1 to 10 carbon atoms, an alicyclic hydrocarbon group having 3 to 10 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms.

[0078] Further, for example, a structure having a dibenzofuranyl group or a dibenzothiophenyl group, wherein the 4-position of the dibenzofuranyl group or the dibenzothiophenyl group is bonded to nitrogen (amine) of the general formula (R0) can be used for A. Specifically, groups represented by the following structural formulas (Ar-58), (Ar-62), (Ar-64) to (Ar-67) can be used. Thereby, it is possible to make it difficult to extend conjugation. Or, the emission wavelength can be made shorter. Or, the reliability can be improved.

[0079] Further, for example, a structure having a carbazolyl group, wherein an aryl group is bonded to the 9-position of the carbazolyl group can be used for A. Specifically, groups represented by the following structural formulas (Ar-50) to (Ar-55) can be used. Thereby, the reliability can be improved.

[0080] [Chemical formula]

[0081] [Chemical formula]

[0082] 《Ar 1 Examples》 Ar 1 represents either a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 25 carbon atoms, and m and n each independently represent an integer of 0 or 1.

[0083] [Examples of aromatic hydrocarbon groups] For example, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, dimethylfluorenyl group, spirofluorenyl group, diphenylfluorenyl group, phenanthryl group, anthryl group, dihydroanthryl group, triphenylenyl group, pyrenyl group, etc. are used for Ar 1It can be used for. Specifically, groups represented by the following structural formulas (Ar-100) to (Ar-120), (Ar-130) to (Ar-140) can be used. Note that these may further have substituents such as a hydrocarbon group having 1 to 10 carbon atoms, an alicyclic hydrocarbon group having 3 to 10 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms.

[0084] Also, for example, a structure having a phenyl group can be used for Ar 1 ((see (Ar-100) to (Ar-108)). Thereby, reliability can be improved. Or, it can be difficult to extend conjugation. Or, the emission wavelength can be made shorter. Or, it is preferable because it can be synthesized at low cost. Or, the molecular weight can be reduced and the sublimation temperature can be lowered. Or, thermal decomposition can be suppressed in the sublimation purification process or the vapor deposition process.

[0085] Also, like (Ar-100) to (Ar-120), those composed of hydrocarbons with a condensed ring number of six-membered rings of 2 or less like benzene ring, naphthalene ring, fluorene ring, or with a condensed ring number of six-membered rings of 3 or more like phenanthrene ring and other six-membered rings condensed only at the a-position, c-position, and e-position with respect to the six-membered ring are difficult to have extended conjugation and can emit light at a shorter wavelength.

[0086] Also, for example, a structure having an alkyl group or a cycloalkyl group can be used ((see (Ar-101) to (Ar-104)). Thereby, the molecule can be made bulky. Or, the sublimation temperature can be lowered. Or, thermal decomposition can be suppressed in the sublimation purification process or the vapor deposition process.

[0087]

Chemical formula

[0088]

Chemical formula

[0089] [Examples of heteroaryl groups] For example, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, etc. can be used for Ar 1 Specifically, groups represented by the above structural formulas (Ar-50) to (Ar-67) or the following structural formulas (Ar-68), (Ar-69) or (Ar-76) to (Ar-97) can be used. These may further have substituents such as a hydrocarbon group having 1 to 10 carbon atoms, an alicyclic hydrocarbon group having 3 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms, etc.

[0090] [Chemical formula]

[0091] [Chemical formula]

[0092] [Example 2 of organic compound] Further, the organic compound described in this embodiment is an organic compound represented by the following general formula (G1).

[0093] [Chemical formula]

[0094] In the above general formula (G1), X 1 to X 3 represent oxygen or sulfur, and X 1 to X 3 may be the same as or different from each other.

[0095] Also, one or two of R 11 to R 22 are an amino group represented by the above general formula (R0) or an aryl group having an amino group, and R 11 to R 22is independently any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, an alicyclic hydrocarbon group having 3 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 13 carbon atoms. Here, R 11 to R 22 When two of them are an amino group represented by the above general formula (R0) or an aryl group having an amino group, a set of the amino group represented by the above general formula (R0) or an aryl group having an amino group may be the same or different from each other. Also, R 11 to R 22 When two of them are an amino group represented by the above general formula (R0) or an aryl group having an amino group, the luminous efficiency can be improved.

[0096] In the above general formula (R0), α 1 and α 2 each independently represent a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 carbon atoms.

[0097] Also, A represents a substituted or unsubstituted heteroaryl group, and Ar 1 represents either a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 25 carbon atoms. Here, m and n each independently represent an integer of 0 or 1.

[0098] <Example 3 of organic compound> Also, the organic compound described in this embodiment is an organic compound in which, in the above general formula (G1), R 12 and R 16 are an amino group represented by the above general formula (R0) or an aryl group having an amino group. A set of the amino group represented by the above general formula (R0) or an aryl group having an amino group may be the same or different from each other. For example, the organic compound described in this embodiment can be represented by the following general formula (G2). Thereby, an improvement in luminous efficiency can be expected.

[0099]

Chemical formula

[0100] <Example 4 of organic compound> In addition, the organic compound described in this embodiment is an organic compound in which, in the above general formula (R0), A has a five-membered ring, and the five-membered ring contains a hetero atom.

[0101] For example, a group having a pyrrole skeleton, a furanyl skeleton, a thienyl skeleton, a pyrazole skeleton, an imidazole skeleton, or an oxazole skeleton can be used for A. Specifically, a carbazolyl group, a furanyl group, a thienyl group, an indazolyl group, a benzisoxazolyl group, a benzofuranyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzothiophenyl group, a benzimidazolyl group, a benzonaphthothiophenyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, etc. can be used for A. Specifically, the groups represented by the above structural formulas (Ar-50) to (Ar-69), (Ar-76) to (Ar-97) can be used. In addition, these may further have substituents such as a hydrocarbon group having 1 to 10 carbon atoms, an alicyclic hydrocarbon group having 3 to 10 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms.

[0102] In addition, for example, a structure in which benzene or naphthalene is condensed at two or more positions with respect to the five-membered ring can be used (see (Ar-50) to (Ar-67), (Ar-80) to (Ar-97)). Thereby, a photochemical reaction can be suppressed. Or, the reliability of the material can be improved.

[0103] In addition, for example, a structure in which benzene is condensed at two or more positions with respect to the five-membered ring can be used (see (Ar-50) to (Ar-67)). Thereby, the emission wavelength can be made shorter. Or, the temperature required for the vapor deposition process can be lowered.

[0104] <Example 5 of organic compound> In addition, the organic compound described in this embodiment is an organic compound in which, in the above general formula (R0), A represents a heteroaryl group having a carbazole skeleton, a dibenzofuran skeleton, or a dibenzothiophene skeleton. Specifically, the groups represented by the above structural formulas (Ar-50) to (Ar-67) or (Ar-80) to (Ar-97) can be used. Note that these may further have substituents such as a hydrocarbon group having 1 to 10 carbon atoms, an alicyclic hydrocarbon group having 3 to 10 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms.

[0105] Also, Ar 1 represents a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a substituent having a carbazole skeleton, a dibenzofuran skeleton, or a dibenzothiophene skeleton. Further, for example, a terphenyl group, a dimethylfluorenyl group, a spirofluorenyl group, a diphenylfluorenyl group, an anthryl group, a dihydroanthryl group, a triphenylenyl group, a pyrenyl group, etc. can be used for Ar 1 Specifically, the groups represented by the above structural formulas (Ar-100) to (Ar-120), (Ar-130) to (Ar-140) can be used. Note that these may further have substituents such as a hydrocarbon group having 1 to 10 carbon atoms, an alicyclic hydrocarbon group having 3 to 10 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms. Further, for example, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, etc. can be used for Ar 1 Specifically, the groups represented by the above structural formulas (Ar-50) to (Ar-67) can be used. Note that these may further have substituents such as a hydrocarbon group having 1 to 10 carbon atoms, an alicyclic hydrocarbon group having 3 to 10 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms.

[0106] <Example 6 of organic compound> In addition, the organic compound described in this embodiment is an organic compound in which the amino group or the aryl group having an amino group represented by the above general formula (R0) is the following general formula (R1).

[0107]

Chem.

[0108] In the above general formula (R1), R 31 to R 42 each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, an alicyclic hydrocarbon group having 3 to 6 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 13 carbon atoms.

[0109] <Example 7 of organic compound> In addition, the organic compound described in this embodiment is an organic compound in which the amino group or the aryl group having an amino group represented by the above general formula (R0) is the following general formula (R2).

[0110]

Chem.

[0111] In the above general formula (R2), R 51 to R 67 each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, an alicyclic hydrocarbon group having 3 to 6 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 13 carbon atoms.

[0112] From the viewpoint of heat resistance, it is preferably 850 or more in molecular weight, and from the viewpoint of sublimability, it is preferably 1700 or less, more preferably 1500 or less in molecular weight.

[0113] Thereby, a novel luminescent material having a high luminescence quantum yield can be provided. Or, a novel luminescent material having a high molar extinction coefficient can be provided. Or, a novel luminescent material that exhibits sharp blue in the emission spectrum can be provided.

[0114] Specific examples of the organic compound having the above configuration are shown below.

[0115]

Chem.

[0116]

Chem.

[0117]

Chem.

[0118]

Chem.

[0119]

Chem.

[0120]

Chem.

[0121]

Chem.

[0122]

Chem.

[0123]

Chem.

[0124]

Chem.

[0125]

Chem.

[0126]

Chem.

[0127]

Chem.

[0128]

Chem.

[0129]

Chem.

[0130]

Chem.

[0131]

Chem.

[0132] <Method for Synthesizing Organic Compounds> The method for synthesizing an organic compound according to one embodiment of the present invention will be described. Specifically, the method for synthesizing the organic compound represented by the above general formula (G0) will be described.

[0133] The organic compound represented by the general formula (G0) can be obtained by the following synthesis scheme (SC1). Specifically, it can be obtained by subjecting compound (a1) and q equivalents of compound (a2) with respect to compound (a1) to a cross-coupling reaction.

[0134] Note that compound (a1) has a substituent X 1 and a halogen such as chlorine, bromine, iodine, or a triflate group, etc. as substituent X 1It can be used for. Further, the compound (a2) has a substituent Y 1 and can use hydrogen, an organic tin group, boric acid, dialkoxyboric acid, etc. as the substituent Y 1 for use.

[0135] [Chemical formula]

[0136] This reaction can proceed under various conditions. For example, a synthesis method using a metal catalyst in the presence of a base can be applied. Specifically, Ullmann coupling, Hartwig-Buchwald reaction, Suzuki-Miyaura reaction, etc. can be used.

[0137] In the above general formula (G0), when q is 2 and a pair of HAs are different from each other, the compound (a1) and one selected from two types of compounds (a2) may be subjected to a cross-coupling reaction, and then the other selected from two types of compounds (a2) may be further subjected to a cross-coupling reaction.

[0138] Also, in the above general formula (G0), when q is 1, it can also be obtained by the following synthesis scheme (SC2). Specifically, it can be obtained by subjecting the compound (a3) and the compound (a4) to a cross-coupling reaction.

[0139] [Chemical formula]

[0140] Note that this embodiment can be appropriately combined with other embodiments shown in this specification.

[0141] (Embodiment 2) In this embodiment, the configuration of the light-emitting device 150 according to one aspect of the present invention will be described with reference to FIGS. 1A and 1B.

[0142] FIG. 1A is a diagram for explaining the configuration of a light-emitting device, and FIG. 1B is a diagram for explaining a part of the configuration of the light-emitting device.

[0143] <Example Configuration 1 of Light-Emitting Device 150> The light-emitting device 150 described in this embodiment has an electrode 101, an electrode 102, and a unit 103 (see FIG. 1A). Note that the electrode 102 has a region overlapping with the electrode 101. For example, the electrode 101 can be used as an anode and the electrode 102 can be used as a cathode.

[0144] 《Example Configuration 1 of Unit 103》 The unit 103 has a region sandwiched between the electrode 101 and the electrode 102, and the unit 103 includes a light-emitting material and a host material. For example, the compound described in Embodiment 1 can be used as the light-emitting material.

[0145] The organic compound according to one aspect of the present invention has a high molar extinction coefficient, so the efficiency of energy transfer from the host is good. Therefore, a light-emitting element with high luminous efficiency and good lifespan can be obtained. Specifically, the molar extinction coefficient for light corresponding to the transition energy from the S0 level to the S1 level, specifically light in the vicinity of a wavelength of 400 to 500 nm, is 10 5 (M -1 cm -1 ) or more, which is preferable. Also, since the half-value width of the emission spectrum is narrow and sharp, the color purity is high and the efficiency is high, which is preferable. Further, by combining with a microcavity (micro-optical resonator) structure, the emission spectrum can be made even sharper. Also, the glass transition point is 100 °C or more, and it has excellent heat resistance, which is preferable.

[0146] 《Host Material》 A material having carrier transport properties can be used as the host material. For example, a material having hole transport properties, a material having electron transport properties, a TADF material, a material having an anthracene skeleton, and a mixed material, etc. can be used as the host material.

[0147] [Material Having Hole Transport Properties] As a material having hole transporting properties, it preferably has a hole mobility of 1×10 -6 cm 2 / Vs or more. For example, a compound having an aromatic amine skeleton, a compound having a carbazole skeleton, a compound having a thiophene skeleton, a compound having a furan skeleton, etc. can be used.

[0148] Also, as a material having hole transporting properties, an amine compound or an organic compound having a π-electron excess type heteroaromatic ring skeleton is preferable. For example, a compound having an aromatic amine skeleton, a compound having a carbazole skeleton, a compound having a thiophene skeleton, a compound having a furan skeleton, etc. can be used. Further, for example, the organic compound of one aspect of the present invention can be used.

[0149] Examples of the compound having an aromatic amine skeleton include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluorene-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluorene-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]spiro-9,9'-bifluorene-2-amine (abbreviation: PCBASF), etc. can be used.

[0150] Examples of the compound having a carbazole skeleton include 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviation: CzTP), 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), etc. can be used.

[0151] Examples of compounds having a thiophene skeleton include 4,4’,4’’-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), etc., which can be used.

[0152] 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), etc., which can be used.

[0153] Among those described above, compounds having an aromatic amine skeleton or a carbazole skeleton are preferable because they have good reliability, high hole transportability, and contribute to reducing the driving voltage.

[0154] [Material having electron transportability] Organic compounds having an anthracene skeleton can be used as materials having electron transportability. In particular, organic compounds containing both an anthracene skeleton and a heterocyclic skeleton can be preferably used.

[0155] For example, organic compounds containing both an anthracene skeleton and a nitrogen-containing five-membered ring skeleton or organic compounds containing both an anthracene skeleton and a nitrogen-containing six-membered ring skeleton can be used. Alternatively, organic compounds containing both a nitrogen-containing five-membered ring skeleton having two heteroatoms in the ring and an anthracene skeleton or organic compounds having a nitrogen-containing six-membered ring skeleton having two heteroatoms in the ring can be used. Specifically, a pyrazole ring, an imidazole ring, an oxazole ring, a thiazole ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, etc. can be preferably used for the heterocyclic skeleton.

[0156] In addition, as the material having electron transporting properties, metal complexes and organic compounds having a π-electron deficient heteroaromatic ring skeleton are preferable. As the organic compound having a π-electron deficient heteroaromatic ring skeleton, for example, a heterocyclic compound having a polyazole skeleton, a heterocyclic compound having a diazine skeleton, and a heterocyclic compound having a pyridine skeleton are preferable. In particular, a heterocyclic compound having a diazine skeleton or a heterocyclic compound having a pyridine skeleton is preferable because of its good reliability. Further, a heterocyclic compound having a diazine (pyrimidine or pyrazine) skeleton has high electron transporting properties and can reduce the driving voltage.

[0157] Examples of the metal complex include bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq 2 ), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), etc. can be used.

[0158] Examples of the heterocyclic compound having a polyazole skeleton include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviation: CO11), 2,2’,2’’-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), etc. can be used.

[0159] Examples of the heterocyclic compound having a diazine skeleton include 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzof[h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzof[h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazol-9-yl)biphenyl-3-yl]dibenzof[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), and the like can be used.

[0160] Examples of the heterocyclic compound having a pyridine skeleton include 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), and the like can be used.

[0161] [TADF material] The TADF materials exemplified above can be used as host materials. When a TADF material is used as a host material, the triplet excitation energy generated in the TADF material is converted into singlet excitation energy by reverse intersystem crossing, and further energy transfer to the luminescent substance can enhance the luminous efficiency of the light-emitting device. At this time, the TADF material functions as an energy donor, and the luminescent substance functions as an energy acceptor.

[0162] This is very effective when the above luminescent substance is a fluorescent luminescent substance. Also, at this time, in order to obtain high luminous efficiency, it is preferable that the S1 level of the TADF material is higher than the S1 level of the fluorescent luminescent substance. Also, it is preferable that the T1 level of the TADF material is higher than the S1 level of the fluorescent luminescent substance. Therefore, it is preferable that the T1 level of the TADF material is higher than the T1 level of the fluorescent luminescent substance.

[0163] Also, it is preferable to use a TADF material that exhibits luminescence overlapping with the wavelength of the absorption band on the lowest energy side of the fluorescent luminescent substance. By doing so, the transfer of excitation energy from the TADF material to the fluorescent luminescent substance becomes smooth, and luminescence can be obtained efficiently, which is preferable.

[0164] Also, in order 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. Also, it is preferable that the triplet excitation energy generated in the TADF material does not move to the triplet excitation energy of the fluorescent luminescent substance. For that purpose, it is preferable that the fluorescent luminescent substance has a protecting group around the lumophore (the skeleton responsible for luminescence) that the fluorescent luminescent substance has. As the protecting group, a substituent having no π bond is preferable, a saturated hydrocarbon is preferable, and specifically, an alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, and a trialkylsilyl group having 3 to 10 carbon atoms can be mentioned, and it is more preferable that there are a plurality of protecting groups. A substituent having no π bond has poor function of transporting carriers, so it can keep the distance between the TADF material and the lumophore of the fluorescent luminescent substance far without hardly affecting carrier transport and carrier recombination.

[0165] Here, the lumophore refers to an atomic group (skeleton) that causes luminescence in the fluorescent luminescent substance. The lumophore preferably has a skeleton having a π bond, preferably contains an aromatic ring, and preferably has a condensed aromatic ring or a condensed heteroaromatic ring.

[0166] Examples of the condensed aromatic ring or condensed heteroaromatic ring include a phenanthrene skeleton, a stilbene skeleton, an acridone skeleton, a phenoxazine skeleton, a phenothiazine skeleton, etc. Particularly, fluorescent substances having a naphthalene skeleton, an anthracene skeleton, a fluorene skeleton, a chrysene skeleton, a triphenylene skeleton, a tetracene skeleton, a pyrene skeleton, a perylene skeleton, a coumarin skeleton, a quinacridone skeleton, a naphthobisbenzofuran skeleton are preferable because they have a high fluorescence quantum yield.

[0167] [Material having an anthracene skeleton] When using a fluorescent substance as the luminescent substance, as the host material, a material having an anthracene skeleton is preferable. When using a substance having an anthracene skeleton as the host material of the fluorescent substance, it is possible to realize a light-emitting layer with both good luminous efficiency and durability.

[0168] As the substance having an anthracene skeleton used as the host material, a substance having a diphenylanthracene skeleton, particularly a substance having a 9,10-diphenylanthracene skeleton is preferable because it is chemically stable. Further, when the host material has a carbazole skeleton, it is preferable because the hole injection and transport properties are enhanced. However, when it contains a benzocarbazole skeleton in which a benzene ring is further condensed with carbazole, the HOMO is about 0.1 eV shallower than that of carbazole, and holes can easily enter, so it is more preferable.

[0169] Particularly, when the host material contains a dibenzocarbazole skeleton, the HOMO is about 0.1 eV shallower than that of carbazole, holes can easily enter, and it also has excellent hole transport properties and high heat resistance, so it is suitable. Therefore, a substance having both a 9,10-diphenylanthracene skeleton and a carbazole skeleton (or a benzocarbazole skeleton or a dibenzocarbazole skeleton) is more preferable as the host material. From the above viewpoint of hole injection and transport properties, a benzofluorene skeleton or a dibenzofluorene skeleton may be used instead of the carbazole skeleton.

[0170] Examples of substances having an anthracene skeleton include, for example, 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA), 3-[4-(1-naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenz[c,g]carbazole (abbreviation: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-{4-(9-phenyl-9H-fluoren-9-yl)biphenyl-4'-yl}anthracene (abbreviation: FLPPA), 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth), etc. can be used.

[0171] In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA exhibit very good properties.

[0172] [Constitution Example 1 of Mixed Material] In addition, a material obtained by mixing a plurality of substances can be used as the host material. For example, a material obtained by mixing a material having electron transporting properties and a material having hole transporting properties can be suitably used as the host material. By mixing a material having electron transporting properties and a material having hole transporting properties, the carrier transporting properties of layer 111 can be easily adjusted. Also, the control of the recombination region can be easily performed. The weight ratio of the material having hole transporting properties to the material having electron transporting properties contained in the mixed material may be such that the material having hole transporting properties: the material having electron transporting properties = 1:19 or more and 19:1 or less.

[0173] [Constitution Example 2 of Mixed Material] In addition, a material mixed with a phosphorescent substance can be used as the host material. The phosphorescent substance can be used as an energy donor that supplies excitation energy to the fluorescent substance when the fluorescent substance is used as the luminescent substance.

[0174] In addition, a mixed material containing a material that forms an exciplex can be used as the host material. For example, a material whose emission spectrum of the formed exciplex overlaps with the wavelength of the absorption band on the lowest energy side of the luminescent substance can be used as the host material. Thereby, energy transfer becomes smooth, and the luminous efficiency can be improved. Or the driving voltage can be suppressed.

[0175] Note that at least one of the materials that form the exciplex may be a phosphorescent substance. By doing so, the triplet excitation energy can be efficiently converted into singlet excitation energy by reverse intersystem crossing.

[0176] As a combination of materials that efficiently form an exciplex, it is preferable that the HOMO level of the hole-transporting material is equal to or higher than the HOMO level of the electron-transporting material. Also, it is preferable that the LUMO level of the hole-transporting material is equal to or higher than the LUMO level of the electron-transporting material. Note that the LUMO level and HOMO level of the material can be derived from the electrochemical characteristics (reduction potential and oxidation potential) of the material measured by cyclic voltammetry (CV) measurement.

[0177] Note that the formation of an exciplex can be confirmed, for example, by comparing the emission spectra of a material having hole-transporting properties, the emission spectra of a material having electron-transporting properties, and the emission spectra of a mixed film obtained by mixing these materials, and observing that the emission spectrum of the mixed film is shifted to a longer wavelength (or has a new peak on the longer wavelength side) than the emission spectra of the respective materials. Alternatively, the transient photoluminescence (PL) of a material having hole-transporting properties, the transient PL of a material having electron-transporting properties, and the transient PL of a mixed film obtained by mixing these materials are compared, and the formation of the exciplex can be confirmed by observing differences in transient responses such as that the transient PL lifetime of the mixed film has a longer-lived component or the ratio of the delayed component becomes larger than the transient PL lifetimes of the respective materials. Further, the above transient PL may be read as transient electroluminescence (EL). That is, the transient EL of a material having hole-transporting properties, the transient EL of a material having electron-transporting properties, and the transient EL of a mixed film thereof are compared, and the formation of the exciplex can also be confirmed by observing differences in transient responses.

[0178] 《Configuration Example 2 of Unit 103》 Unit 103 includes layer 111, layer 112, and layer 113. For example, a layer selected from functional layers such as a hole-transporting layer, an electron-transporting layer, a carrier-blocking layer, and an exciton-blocking layer can be used for Unit 103.

[0179] 《Configuration Example of Layer 111》 Layer 111 includes a region sandwiched between layer 112 and layer 113, and layer 111 contains a light-emitting material EM and a host material. For example, the compound described in Embodiment 1 can be used as the light-emitting material EM.

[0180] Note that layer 111 can be referred to as a light-emitting layer. Preferably, layer 111 is disposed in a region where holes and electrons recombine. Thereby, the energy generated by the recombination of carriers can be efficiently emitted as light EL1 (see Fig. 1A). Also, preferably, layer 111 is disposed away from the metal used for the electrodes and the like. Thereby, the quenching phenomenon caused by the metal used for the electrodes and the like can be suppressed.

[0181] 《Configuration Example 1 of Layer 112》 Layer 112 includes a region sandwiched between electrode 101 and layer 111. For example, a material having hole-transporting properties can be used for layer 112. Also, layer 112 can be referred to as a hole-transporting layer. Preferably, a substance having a band gap larger than the band gap of the light-emitting material included in layer 111 is used for layer 112. Thereby, the energy transfer from the excitons generated in layer 111 to layer 112 can be suppressed.

[0182] [Material having hole-transporting properties] For example, a material having hole-transporting properties that can be used for layer 111 can be used for layer 112.

[0183] 《Configuration Example 1 of Layer 113》 Layer 113 includes a region sandwiched between layer 111 and electrode 102. For example, a material having electron-transporting properties can be used for layer 113. Also, layer 113 can be referred to as an electron-transporting layer. Preferably, a substance having a band gap larger than the band gap of the light-emitting material included in layer 111 is used for layer 113. Thereby, the energy transfer from the excitons generated in layer 111 to layer 113 can be suppressed.

[0184] [Material having electron-transporting properties] As the material having electron-transporting properties, the electron mobility at the square root of the electric field strength [V / cm] of 600 is 1×10 -7 cm 2 / Vs or more, 5×10 -5 cm 2It is preferably below / Vs. By suppressing the electron transport property in the electron transport layer, the amount of electrons injected into the light-emitting layer can be controlled. Or, it is possible to prevent the light-emitting layer from being in a state of excessive electrons.

[0185] For example, a material having an electron transport property that can be used for layer 111 can be used for layer 113. Specifically, a material having an electron transport property that can be used for a host material can be used for layer 113.

[0186] <Configuration Example 2 of Light-Emitting Device 150> In addition, the light-emitting device 150 described in this embodiment has layer 105 and layer 104 (see FIG. 1A).

[0187] <<Configuration Example of Layer 105>> Layer 105 includes a region sandwiched between electrode 102 and unit 103.

[0188] For example, a material having an electron injection property can be used for layer 105. Specifically, a donor substance can be used for layer 105. Or, a composite material in which a donor substance is contained in a material having an electron transport property can be used for layer 105. Thereby, for example, it is possible to facilitate the injection of electrons from electrode 102. Or, the driving voltage of the light-emitting device can be reduced. Or, various conductive materials can be used for electrode 102 regardless of the work function. Specifically, Al, Ag, ITO, indium tin oxide containing silicon or silicon oxide, etc. can be used for electrode 102.

[0189] [Material 1 Having Electron Injection Property] For example, an alkali metal, an alkaline earth metal, a rare earth metal, or a compound thereof can be used for the donor substance. Or, an organic compound such as tetrathianaphthacene (abbreviation: TTN), nickelocene, or decamethylnickelocene can also be used for the donor substance.

[0190] Specifically, an alkali metal compound (including oxides, halides, carbonates), an alkaline earth metal compound (including oxides, halides, carbonates), or a rare earth metal compound (including oxides, halides, carbonates), etc. can be used for a material having electron injection properties.

[0191] Specifically, lithium oxide, lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), lithium carbonate, cesium carbonate, 8-hydroxyquinolinato-lithium (abbreviation: Liq), etc. can be used for a material having electron injection properties.

[0192] [Material 2 with electron injection properties] For example, a composite material containing an alkali metal or an alkaline earth metal or their compounds and a substance having electron transporting properties can be used for a material having electron injection properties.

[0193] For example, a material having electron transporting properties that can be used for unit 103 can be used for a material having electron injection properties.

[0194] Also, a material containing a fluoride of an alkali metal in a microcrystalline state and a substance having electron transporting properties or a material containing a fluoride of an alkaline earth metal in a microcrystalline state and a substance having electron transporting properties can be used for a material having electron injection properties.

[0195] In particular, a material containing 50 wt% or more of a fluoride of an alkali metal or a fluoride of an alkaline earth metal can be preferably used. Or, an organic compound having a bipyridine skeleton can be preferably used. Thereby, the refractive index of layer 104 can be decreased. Or, the external quantum efficiency of the light-emitting device can be improved.

[0196] [Material 3 with electron injection properties] In addition, the electride can be used for a material having electron injection properties. For example, a substance obtained by adding electrons to a mixed oxide of calcium and aluminum at a high concentration can be used for a material having electron injection properties.

[0197] <<Configuration Example of Electrode 102>> For example, a conductive material can be used for the electrode 102. Specifically, a metal, an alloy, an electrically conductive compound, and a mixture thereof can be used for the electrode 102. For example, a material having a smaller work function than the electrode 101 can be used for the electrode 102. Specifically, a material having a work function of 3.8 eV or less can be preferably used.

[0198] For example, an element belonging to Group 1 of the periodic table, an element belonging to Group 2 of the periodic table, a rare earth metal, and an alloy containing these can be used for the electrode 102.

[0199] Specifically, lithium (Li), cesium (Cs), etc., magnesium (Mg), calcium (Ca), strontium (Sr), etc., europium (Eu), ytterbium (Yb), etc., and alloys containing these (MgAg, AlLi) can be used for the electrode 102.

[0200] <<Configuration Example 1 of Layer 104>> The layer 104 includes a region sandwiched between the electrode 101 and the unit 103. Note that the layer 104 can be referred to as a hole injection layer. For example, a material having hole injection properties can be used for the layer 104.

[0201] Specifically, an acceptor material AM and a composite material can be used for the layer 104. Note that an organic compound and an inorganic compound can be used for the acceptor material AM. By applying an electric field, the acceptor material AM can extract electrons from an adjacent hole transport layer (or hole transport material).

[0202] [Example 1 of Material Having Hole Injection Properties] The material AM having acceptor properties can be used as a material having hole injection properties. Thereby, for example, holes can be easily injected from the electrode 101. Or, the driving voltage of the light-emitting device can be reduced.

[0203] [Material AM having acceptor properties] For example, a compound having an electron-withdrawing group (such as a halogen group or a cyano group) can be used as a material having acceptor properties. Note that an organic compound having acceptor properties is easy to vaporize and easy to form a film. Thereby, the productivity of the light-emitting device can be increased.

[0204] Specifically, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F 4 -TCNQ), chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN), 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ), 2-(7-dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyrene-2-ylidene) malononitrile, etc. can be used as a material having acceptor properties.

[0205] In particular, a compound in which an electron-withdrawing group is bonded to a condensed aromatic ring having a plurality of heteroatoms like HAT-CN is thermally stable and preferable.

[0206] Also, a [3]radialene derivative having an electron-withdrawing group (especially a halogen group such as a fluoro group or a cyano group) is preferable because it has very high electron accepting properties.

[0207] Specifically, α,α’,α’’-1,2,3-cyclopropanetriylidene tris[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α’,α’’-1,2,3-cyclopropanetriylidene tris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], α,α’,α’’-1,2,3-cyclopropanetriylidene tris[2,3,4,5,6-pentafluorobenzeneacetonitrile], etc. can be used.

[0208] In addition, molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide, etc. can be used for the acceptor material AM.

[0209] In addition, phthalocyanine (abbreviation: H 2 Pc), phthalocyanine-based complex compounds such as copper phthalocyanine (CuPc), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: DNTPD), etc. compounds having an aromatic amine skeleton can be used.

[0210] In addition, polymers such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) can be used.

[0211] [Example 2 of the hole injection material] The composite material can be used for the hole injection material. For example, a composite material containing an acceptor material AM in a hole transporting material can be used. Thereby, the material for forming the electrode can be selected in a wide range regardless of the work function. Or, not only materials with a large work function but also materials with a small work function can be used for the electrode 101.

[0212] Various organic compounds can be used as materials having hole transporting properties in the composite material. For example, compounds having an aromatic amine skeleton, carbazole derivatives, aromatic hydrocarbons, polymer compounds (oligomers, dendrimers, polymers, etc.) can be used as materials having hole transporting properties in the composite material. Note that a substance having a hole mobility of 1×10 -6 cm 2 / Vs or more can be preferably used.

[0213] Also, for example, a substance having a relatively deep HOMO level of -5.7 eV or more and -5.4 eV or less can be preferably used as a material having hole transporting properties in the composite material. Thereby, the injection of holes into the hole transport layer can be facilitated. Or, the reliability of the light emitting device can be improved.

[0214] Examples of the compound having an aromatic amine skeleton include N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), etc. can be used.

[0215] Examples of the carbazole derivative include 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (abbreviation: CzPA), 1,4-bis[4-(N-carbazolyl)phenyl]-2,3,5,6-tetraphenylbenzene, and the like can be used.

[0216] Examples of aromatic hydrocarbons include 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 2-tert-butyl-9,10-di(1-naphthyl)anthracene, 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 2-tert-butyl-9,10-bis(4-phenylphenyl)anthracene (abbreviation: t-BuDBA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 9,10-diphenylanthracene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation: t-BuAnth), 9,10-bis(4-methyl-1-naphthyl)anthracene (abbreviation: DMNA), 2-tert-butyl-9,10-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, etc. can be used.

[0217] Examples of aromatic hydrocarbons having a vinyl group include 4,4’-bis(2,2-diphenylvinyl)biphenyl (abbreviation: DPVBi), 9,10-bis[4-(2,2-diphenylvinyl)phenyl]anthracene (abbreviation: DPVPA), etc. can be used.

[0218] For example, pentacene, coronene, etc. can also be used.

[0219] Examples of the high molecular compound include poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N’-[4-(4-diphenylamino)phenyl]phenyl-N’-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N’-bis(4-butylphenyl)-N,N’-bis(phenyl)benzidine] (abbreviation: Poly-TPD), etc., which can be used.

[0220] In addition, for example, a substance having any one of a carbazole skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton, and an anthracene skeleton can be suitably used as a material having hole transporting properties of the composite material. Further, a substance including an aromatic amine having a substituent containing a dibenzofuran ring or a dibenzothiophene ring, an aromatic monoamine having a naphthalene ring, or an aromatic monoamine in which a 9-fluorenyl group is bonded to the nitrogen of the amine via an arylene group can be used. Note that when a substance having an N,N-bis(4-biphenyl)amino group is used, the reliability of the light-emitting device can be improved.

[0221] Examples of materials having hole-transporting properties among these composite materials include N-(4-biphenyl)-6,N-diphenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BnfABP), N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf), 4,4'-bis(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)-4''-phenyltriphenylamine (abbreviation: BnfBB1BP), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-6-amine (abbreviation: BBABnf(6)), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf(8)), N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviation: BBABnf(II)(4)), N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP), N-[4-(dibenzothiophene-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-03), 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'-binaphthalen-1-yl)triphenylamine (abbreviation: BBAβNαNB-02), 4-(4-biphenylyl)-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: TPBiAβNB), 4-(3-biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: mTPBiAβNBi), 4-(4-biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: TPBiAβNBi), 4-phenyl-4'-(1-naphthyl)triphenylamine (abbreviation: αNBA1BP), 4,4'-bis(1-naphthyl)triphenylamine (abbreviation: αNBB1BP), 4,4'-diphenyl-4''-[4'-(carbazol-9-yl)biphenyl-4-yl]triphenylamine (abbreviation: YGTBi1BP), 4'-[4-(3-phenyl-9H-carbazol-9-yl)phenyl]tris(1,1'-biphenyl-4-yl)amine (abbreviation: YGTBi1BP-02), 4-diphenyl-4'-(2-naphthyl)-4''-{9-(4-biphenylyl)carbazole)}triphenylamine (abbreviation: YGTBiβNB), N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-N-[4-(1-naphthyl)phenyl]-9,9'-spirobi(9H-fluorene)-2-amine (abbreviation: PCBNBSF), N,N-bis(4-biphenylyl)-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: BBASF), N,N-bis(1,1'-biphenyl-4-yl)-9,9'-spirobi[9H-fluorene]-4-amine (abbreviation: BBASF(4)), N-(1,1'-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobi(9H-fluorene)-4-amine (abbreviation: oFBiSF), N-(4-biphenyl)-N-(dibenzofuran-4-yl)-9,9-Dimethyl-9H-fluorene-2-amine (abbreviation: FrBiF), N-[4-(1-naphthyl)phenyl]-N-[3-(6-phenyldibenzofuran-4-yl)phenyl]-1-naphthylamine (abbreviation: mPDBfBNBN), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-phenyl-4'-[4-(9-phenylfluoren-9-yl)phenyl]triphenylamine (abbreviation: BPAFLBi), 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]spiro-9,9'-bifluorene-2-amine (abbreviation: PCBASF), N-(1,1'-biphenyl-4-yl)-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluorene-2-amine (abbreviation: PCBBiF), N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluorene-4-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluorene-3-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluorene-2-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluorene-1-amine, etc. can be used.,

[0222] [Example 3 of the material having hole injection property] A composite material containing a material having hole transporting properties, a material AM having acceptor properties, and a fluoride of an alkali metal or an alkaline earth metal can be used for a material having hole injecting properties. In particular, a composite material in which the fluorine atoms are 20% or more in atomic ratio can be preferably used. Thereby, the refractive index of layer 104 can be reduced. Or, a layer having a low refractive index can be formed inside the light emitting device. Or, the external quantum efficiency of the light emitting device can be improved.

[0223] <Configuration Example 3 of Light Emitting Device 150> In addition, in the light emitting device 150 described in this embodiment, layer 113 contains material OMC. For example, an organometallic complex of an alkali metal or an organometallic complex of an alkaline earth metal can be used as material OMC.

[0224] 《Configuration Example 2 of Layer 113》 For example, a material containing an alkali metal, an alkali metal compound or an alkali metal complex and a substance having electron transporting properties can be used for layer 113.

[0225] In addition, material OMC preferably contains, for example, an 8-hydroxyquinolinate structure. Specifically, 8-hydroxyquinolinate-lithium (abbreviation: Liq), 8-hydroxyquinolinate-sodium (abbreviation: Naq), etc. can be used.

[0226] In particular, a complex of a monovalent metal ion, especially a complex of lithium, is preferable, and Liq is more preferable. When including an 8-hydroxyquinolinate structure, its methyl-substituted product (for example, 2-methyl-substituted product or 5-methyl-substituted product) etc. can also be used. Also, in the electron transport layer, it is preferable that there is a concentration difference (including the case of 0) in the thickness direction for an alkali metal or a simple substance, compound or complex of an alkali metal.

[0227] 《Configuration Example 2 of Layer 104》 Further, layer 104 includes a material AM having acceptor properties and a material HT1. The material HT1 has a first HOMO level HOMO1, and the first HOMO level HOMO1 is -5.7 eV or more and -5.4 eV or less (see FIG. 1B).

[0228] For example, an organic compound having an electron-withdrawing group (such as a halogen group or a cyano group) can be used as the material AM having acceptor properties. Note that the organic compound having acceptor properties is easy to vaporize and easy to form a film. Thereby, the productivity of the light-emitting device can be improved.

[0229] Also, a material having hole-transporting properties can be used as the material HT1. For example, the material used for layer 112 can be used as the material HT1.

[0230] <<Configuration Example 2 of Layer 112>> Layer 112 includes a region 112A and a region 112B, and the region 112B includes a region sandwiched between the layer 111 and the region 112A (see FIG. 1A).

[0231] The region 112B includes a material HT2. The material HT2 has a second HOMO level HOMO2, and the second HOMO level HOMO2 is in the range of -0.2 eV or more and 0 eV or less with respect to the first HOMO level HOMO1 (see FIG. 1B).

[0232] Note that this embodiment can be appropriately combined with other embodiments shown in this specification.

[0233] (Embodiment 3) In this embodiment, the configuration of the light-emitting device 150 according to one aspect of the present invention will be described with reference to FIG. 2A.

[0234] FIG. 2A is a cross-sectional view for explaining the configuration of the light-emitting device according to one aspect of the present invention, and has a configuration different from that of the light-emitting device described with reference to FIG. 1A.

[0235] <<Configuration Example of Light-Emitting Device 150>> The light-emitting device 150 described in this embodiment includes an electrode 101, an electrode 102, a unit 103, an intermediate layer 106, and a unit 103(12) (see Fig. 2A). Further, a layer 105(12) is provided.

[0236] The unit 103 includes a region sandwiched between the electrode 101 and the electrode 102, and the unit 103(12) includes a region sandwiched between the electrode 101 and the unit 103. Further, the intermediate layer 106 includes a region sandwiched between the unit 103(12) and the unit 103.

[0237] The light-emitting device 150 has a plurality of stacked units. The number of units is not limited to 2, and 3 or more units can be stacked. Note that a light-emitting device having a configuration of a plurality of stacked units may be referred to as a stacked light-emitting device or a tandem light-emitting device. Thereby, high-brightness light emission can be achieved while keeping the current density low. Or, the reliability can be improved. Or, the driving voltage can be reduced as compared with the same brightness. Or, the power consumption can be suppressed.

[0238] Further, the layer 105(12) includes a region sandwiched between the unit 103(12) and the intermediate layer 106. For example, the same configuration as the layer 105 described in Embodiment 2 can be used for the layer 105(12).

[0239] <<Configuration Example of Unit 103(12)>> The unit 103(12) has a function of emitting light EL12. Further, a configuration that can be used for the unit 103 can be used for the unit 103(12). For example, the same configuration as the unit 103 can be used for the unit 103(12).

[0240] Alternatively, a configuration different from that of unit 103 can be used for unit 103(12). For example, a configuration with a light emission color different from that of unit 103 can be used for unit 103(12). Specifically, unit 103 that emits red light and green light, and unit 103(12) that emits blue light can be used. Thereby, a light emitting device that emits light of a desired color can be provided. Alternatively, for example, a light emitting device that emits white light can be provided.

[0241] 《Configuration Example of Intermediate Layer 106》 Intermediate layer 106 includes layer 106A and layer 106B. Intermediate layer 106 has a function of supplying electrons to one of unit 103 and unit 103(12) and supplying holes to the other.

[0242] Layer 106B contains a material AM having acceptor properties and a material having hole transporting properties.

[0243] Note that layer 106B can be referred to as a charge generation layer. The charge generation layer has a function of supplying electrons to the anode side and supplying holes to the cathode side by applying a voltage. Specifically, it can supply electrons to unit 103(12) disposed on the anode side.

[0244] Layer 106A includes a region sandwiched between layer 106B and unit 103(12). Note that layer 106A can be referred to as, for example, an electron relay layer.

[0245] For example, a substance having electron transporting properties can be used for the electron relay layer. By providing the electron relay layer (layer 106A), the layer in contact with the anode side of the electron relay layer can be separated from the layer in contact with the cathode side of the electron relay layer. Alternatively, the interaction between the layer in contact with the anode side of the electron relay layer and the layer in contact with the cathode side of the electron relay layer can be reduced. Alternatively, electrons can be smoothly supplied to the layer in contact with the anode side of the electron relay layer.

[0246] For example, a substance having electron transporting properties can be suitably used for the electron relay layer. Specifically, a substance having a LUMO level between the LUMO level of the acceptor material AM used for layer 106B and the LUMO level of the hole transporting material used for layer 106B can be suitably used for the electron relay layer.

[0247] For example, a substance having electron transporting properties and having a LUMO level in the range of -5.0 eV or more, preferably -5.0 eV or more and -3.0 eV or less can be used for the electron relay layer.

[0248] Specifically, a phthalocyanine-based material can be used for the electron relay layer. Alternatively, a metal complex having a metal-oxygen bond and an aromatic ligand can be used for the electron relay layer.

[0249] Note that layer 106B can be referred to as a charge generation layer. The charge generation layer has a function of supplying electrons to the anode side and holes to the cathode side by applying a voltage. Specifically, electrons can be supplied to unit 103(12) disposed on the anode side.

[0250] Note that the present embodiment can be appropriately combined with other embodiments shown in this specification.

[0251] (Embodiment 4) In the present embodiment, the configuration of the light-emitting device 150 according to one aspect of the present invention will be described with reference to FIG. 2B.

[0252] FIG. 2B is a cross-sectional view for explaining the configuration of the light-emitting device according to one aspect of the present invention, and has a configuration different from that of the light-emitting device described with reference to FIG. 1A.

[0253] <Configuration example of the light-emitting device 150> In addition, the light-emitting device 150 described in the present embodiment has an electrode 101, an electrode 102, a unit 103, a layer 104, and an intermediate layer 106 (see FIG. 2B).

[0254] Note that the light-emitting device 150 is different from the configuration illustrated in FIG. 1 in that an intermediate layer 106 is provided between the layer 105 and the electrode 102. Here, the different parts will be described in detail, and for the parts where the same configuration can be used, the above description will be incorporated by reference.

[0255] <<Configuration Example of Intermediate Layer 106>> The intermediate layer 106 includes a region sandwiched between the unit 103 and the electrode 102, and the intermediate layer 106 includes a layer 106A and a layer 106B.

[0256] <<Configuration Example of Layer 106A>> The layer 106A includes a region sandwiched between the layer 106B and the layer 105. For example, the electron relay layer described in Embodiment 3 can be used as the layer 106A.

[0257] <<Configuration Example of Layer 106B>> The layer 106B can be, for example, a charge generation layer. The charge generation layer has a function of supplying electrons to the anode side and holes to the cathode side by applying a voltage. Specifically, it can supply electrons to the unit 103 disposed on the anode side.

[0258] Also, for example, a composite material exemplified as a material having hole injection properties can be used for the charge generation layer. Further, for example, a laminated film in which a film containing the composite material and a film containing a material having hole transporting properties are laminated can be used for the charge generation layer.

[0259] <<Fabrication Method of Light-Emitting Device 150>> For example, each layer of the electrode 101, the electrode 102, the unit 103, and the intermediate layer 106 can be formed by using a dry method, a wet method, a vapor deposition method, a droplet discharge method, a coating method, a printing method, or the like. Also, each layer of the unit 103(12) described in Embodiment 3 can be formed by using the same method. Further, different methods can be used for forming each configuration.

[0260] Specifically, the light-emitting device 150 can be manufactured using a coating device such as a vacuum evaporation device, an inkjet device, a spin coater, a gravure printing device, an offset printing device, a screen printing device, or the like.

[0261] For example, an electrode can be formed by a wet method using a paste of a metal material or a sol-gel method. Specifically, an indium oxide-zinc oxide film can be formed by a sputtering method using a target in which 1 wt% or more and 20 wt% or less of zinc oxide is added to indium oxide. Further, an indium tungsten oxide (IWZO) film containing tungsten oxide and zinc oxide can be formed by a sputtering method using a target containing 0.5 wt% or more and 5 wt% or less of tungsten oxide and 0.1 wt% or more and 1 wt% or less of zinc oxide with respect to indium oxide.

[0262] Note that this embodiment can be appropriately combined with other embodiments described in this specification.

[0263] (Embodiment 5) In this embodiment, the configuration of the light-emitting panel 700 according to one aspect of the present invention will be described with reference to FIG. 3A.

[0264] <Configuration Example of Light-Emitting Panel 700> The light-emitting panel 700 described in this embodiment includes a light-emitting device 150 and a light-emitting device 150(2) (see FIG. 3A).

[0265] For example, the light-emitting device described in any one of Embodiments 2 to 4 can be used as the light-emitting device 150.

[0266] <Configuration Example of Light-Emitting Device 150(2)> The light-emitting device 150(2) described in this embodiment includes an electrode 101(2), an electrode 102, and a unit 103(2) (see FIG. 3A). For example, a part of the configuration of the light-emitting device 150 can be used as a part of the configuration of the light-emitting device 150(2). Thereby, a part of the configuration can be made common. Or the manufacturing process can be simplified.

[0267] 《Configuration Example of Unit 103(2)》 The unit 103(2) includes a region sandwiched between the electrode 101(2) and the electrode 102.

[0268] The unit 103(2) has a single-layer structure or a stacked structure. For example, a layer selected from functional layers such as a hole transport layer, an electron transport layer, a carrier blocking layer, and an exciton blocking layer can be used for the unit 103(2).

[0269] The unit 103(2) includes a region where electrons injected from one electrode recombine with holes injected from the other electrode. For example, it includes a region where holes injected from the electrode 101(2) recombine with electrons injected from the electrode 102.

[0270] Also, the unit 103(2) includes a layer 111(2). For example, a light-emitting material that emits light of a color different from that of the layer 111 included in the unit 103 can be used for the layer 111(2).

[0271] 《Configuration Example 1 of Layer 111(2)》 The layer 111(2) includes a region sandwiching a layer 104 between it and the electrode 101, and the layer 111(2) contains a light-emitting material EM.

[0272] Note that layer 111(2) contains a host material. Also, layer 111(2) can be referred to as a light-emitting layer. Preferably, layer 111(2) is arranged in a region where holes and electrons recombine. Thereby, the energy generated by the recombination of carriers can be efficiently converted into light and emitted. Also, preferably, layer 111(2) is arranged away from the metal used for electrodes and the like. Thereby, the quenching phenomenon caused by the metal used for electrodes and the like can be suppressed.

[0273] For example, a fluorescent substance, a phosphorescent substance, or a substance showing thermally activated delayed fluorescence (TADF) can be used as the light-emitting material. Thereby, the energy generated by the recombination of carriers can be emitted as light EL2 from the light-emitting material (see Fig. 3A).

[0274] [Fluorescent substance] A fluorescent substance can be used for layer 111(2). For example, the fluorescent substances exemplified below can be used for layer 111(2). Note that the present invention is not limited thereto, and various known fluorescent substances can be used for layer 111(2).

[0275] Specifically, 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl-9-anthryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), N,N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazol-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-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), N,N''-(2-tert-butylanthracene-9,10-diyl-di-4,1-phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine] (abbreviation: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: 2PCAPPA), N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA), N,N,N',N',N'',N'',N''',N''' -octaphenyldibenzo[g,p]chrysene-2,7,10,15-tetraamine (abbreviation: DBC1), coumarin 30, N-(9,10-diphenyl-2-anthryl)-N,9-Diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), 9,10-bis(1,1'-biphenyl-2-yl)-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), Coumarin 545T, N,N'-diphenylquinacridone, (abbreviation: DPQd), Rubrene, 5,12-bis(1,1'-biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BPT), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl-4H-pyran-4-ylidene)propanedinitrile (abbreviation: DCM1), 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTB), 2-(2,6-bis{2-[4-(dimethylamino)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]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: BisDCJTM), N,N’-(pyrene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03), 3,10-bis[N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b’]bisbenzofuran (abbreviation: 3,10PCA2Nbf(IV)-02), 3,10-bis[N-(dibenzofuran-3-yl)-N-phenylamino]naphtho[2,3-b;6,7-b’]bisbenzofuran (abbreviation: 3,10FrA2Nbf(IV)-02), etc. can be used.,

[0276] In particular, condensed aromatic diamine compounds typified by pyrene diamine compounds such as 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6BnfAPrn-03 are preferable because they have high hole trapping properties and are excellent in luminous efficiency and reliability.

[0277] [Phosphorescent material 1] Also, a phosphorescent material can be used for layer 111(2). For example, the phosphorescent materials exemplified below can be used for layer 111(2). Note that the present invention is not limited thereto, and various known phosphorescent materials can be used for layer 111(2).

[0278] Specifically, an organometallic iridium complex having a 4H-triazole skeleton or the like can be used for layer 111(2). Specifically, tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium(III) (abbreviation: [Ir(mpptz-dmp) 3) Tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Mptz) 3 ) Tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPrptz-3b) 3 ) etc. can be used.

[0279] Also, for example, an organometallic iridium complex having a 1H-triazole skeleton etc. can be used. Specifically, tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(Mptz1-mp) 3 ) Tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Prptz1-Me) 3 ) etc. can be used.

[0280] Also, for example, an organometallic iridium complex having an imidazole skeleton etc. can be used. Specifically, fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpmi) 3 ) Tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmpimpt-Me) 3 ) etc. can be used.

[0281] Also, for example, an organometallic iridium complex having a phenylpyridine derivative having an electron-withdrawing group as a ligand etc. can be used. Specifically, bis[2-(4’,6’-difluorophenyl)pyridinato-N,C 2’ iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4’,6’-difluorophenyl)pyridinato-N,C 2’Iridium(III) picolinate (abbreviation: FIrpic), bis{2-[3’,5’-bis(trifluoromethyl)phenyl]pyridinato-N,C 2’} iridium(III) picolinate (abbreviation: [Ir(CF 3 ppy) 2 (pic)]), bis[2-(4’,6’-difluorophenyl)pyridinato-N,C 2’ iridium(III) acetylacetonate (abbreviation: FIracac), etc. can be used.

[0282] These are compounds that exhibit blue phosphorescent emission and are compounds having a peak in the emission wavelength from 440 nm to 520 nm.

[0283] [Phosphorescent substance 2] Also, for example, an organometallic iridium complex having a pyrimidine skeleton or the like can be used for layer 111(2). Specifically, 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.

[0284] Also, for example, an organometallic iridium complex having a pyrazine skeleton can be used. Specifically, (acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-Me) 2 (acac)], (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-iPr) 2 (acac)], etc. can be used.

[0285] Also, for example, an organometallic iridium complex having a pyridine skeleton can be used. Specifically, tris(2-phenylpyridinato-N,C 2’ )iridium(III) (abbreviation: [Ir(ppy) 3 ), bis(2-phenylpyridinato-N,C 2’ )iridium(III) acetylacetonate (abbreviation: [Ir(ppy) 2 (acac)]), bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: [Ir(bzq) 2 (acac)]), tris(benzo[h]quinolinato)iridium(III) (abbreviation: [Ir(bzq) 3 ), tris(2-phenylquinolinato-N,C 2’ )iridium(III) (abbreviation: [Ir(pq) 3 ), bis(2-phenylquinolinato-N,C 2’ )iridium(III) acetylacetonate (abbreviation: [Ir(pq) 2(acac)]), [2-d3-methyl-(2-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridyl-κN2)phenyl-κ]iridium(III) (abbreviation: [Ir(5mppy-d3)2(mbfpypy-d3)]), [2-d3-methyl-(2-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(ppy)2(mbfpypy-d3)]), etc. can be used.

[0286] In addition, for example, rare earth metal complexes and the like can be used. Specifically, tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [Tb(acac) 3 (Phen)]), etc. can be mentioned.

[0287] These are mainly compounds that exhibit green phosphorescent emission and have a peak in the emission wavelength range from 500 nm to 600 nm. In addition, organometallic iridium complexes having a pyrimidine skeleton are particularly preferred because they are also outstanding in terms of reliability and luminescence efficiency.

[0288] [Phosphorescent substance 3] In addition, for example, organometallic iridium complexes having a pyrimidine skeleton and the like can be used in layer 111(2). Specifically, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir(5mdppm) 2 (dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm) 2 (dpm)]), bis[4,6-di(naphthalen-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(d1npm) 2 (dpm)]), etc. can be used.

[0289] In addition, for example, an organometallic iridium complex having a pyrazine skeleton or the like can be used. Specifically, (acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III) (abbreviation: [Ir(tppr) 2 (acac)]), bis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(tppr) 2 (dpm)]), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq) 2 (acac)]), etc. can be used.

[0290] In addition, for example, an organometallic iridium complex having a pyridine skeleton or the like can be used. Specifically, 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.

[0291] In addition, for example, a platinum complex or the like can be used. Specifically, 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP), etc. can be used.

[0292] In addition, for example, a rare earth metal complex or the like can be used. Specifically, tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: [Eu(DBM) 3 (Phen)]), tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: [Eu(TTA) 3 (Phen)]), etc. can be used.

[0293] These are compounds that exhibit red phosphorescent emission and have an emission peak in the range of 600 nm to 700 nm. In addition, an organometallic iridium complex having a pyrazine skeleton can obtain red emission with a chromaticity that can be favorably used in a display device.

[0294] [Substance exhibiting thermally activated delayed fluorescence (TADF)] A substance exhibiting thermally activated delayed fluorescence (TADF) (also referred to as a TADF material) can be used for layer 111(2). For example, the TADF materials exemplified below can be used for layer 111(2). Note that the present invention is not limited thereto, and various known TADF materials can be used for layer 111(2).

[0295] 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.

[0296] Specifically, protoporphyrin-tin fluoride complex (SnF 2 (Proto IX)), mesoporphyrin-tin fluoride complex (SnF 2 (Meso IX)), hematoporphyrin-tin fluoride complex (SnF 2 (Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complex (SnF 2 (Copro III-4Me)), octaethylporphyrin-tin fluoride complex (SnF 2 (OEP)), etioporphyrin-tin fluoride complex (SnF 2 (Etio I)), octaethylporphyrin-platinum chloride complex (PtCl 2 OEP), etc. can be used.

[0297]

Chemical formula

[0298] In addition, for example, a heterocyclic compound having one or both of a π-electron rich heterocyclic aromatic ring and a π-electron deficient heterocyclic aromatic ring can be used as the TADF material.

[0299] Specifically, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ) whose structural formula is shown below, 9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzTzn), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 2-[4-(10H-phenoxazin-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4-(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-dimethyl-9H-acridin-10-yl)-9H-xanthen-9-one (abbreviation: ACRXTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10'H-spiro[acridine-9,9'-anthracene]-10'-one (abbreviation: ACRSA), etc. can be used.

[0300]

Chemical formula

[0301] Since the complex ring compound has a π - electron - excessive heteroaromatic ring and a π - electron - deficient heteroaromatic ring, it has both high electron - transporting property and hole - transporting property, which is preferable. Among them, among the skeletons having a π - electron - deficient heteroaromatic ring, a pyridine skeleton, a diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton), and a triazine skeleton are preferable because they are stable and have good reliability. In particular, a benzofuropyrimidine skeleton, a benzothienopyrimidine skeleton, a benzofuropyrazine skeleton, and a benzothienopyrazine skeleton are preferable because they have high acceptor property and good reliability.

[0302] Also, among the skeletons having a π - electron - excessive heteroaromatic ring, an acridine skeleton, a phenoxazine skeleton, a phenothiazine skeleton, a furan skeleton, a thiophene skeleton, and a pyrrole skeleton are stable and have good reliability. Therefore, it is preferable to have at least one of these skeletons. As the furan skeleton, a dibenzofuran skeleton is preferable, and as the thiophene skeleton, a dibenzothiophene skeleton is preferable. As the pyrrole skeleton, an indole skeleton, a carbazole skeleton, an indolocarbazole skeleton, a bicarba - zole skeleton, and a 3-(9 - phenyl - 9H - carbazol - 3 - yl)-9H - carbazole skeleton are particularly preferable.

[0303] In addition, a substance in which a π - electron - excessive heteroaromatic ring and a π - electron - deficient heteroaromatic ring are directly bonded is particularly preferable because both the electron - donating property of the π - electron - excessive heteroaromatic ring and the electron - accepting property of the π - electron - deficient heteroaromatic ring are enhanced, and the energy difference between the S1 level and the T1 level becomes small, so that thermally activated delayed fluorescence can be efficiently obtained. Instead of the π - electron - deficient heteroaromatic ring, an aromatic ring bonded with an electron - withdrawing group such as a cyano group may be used. Also, as the π - electron - excessive skeleton, an aromatic amine skeleton, a phenazine skeleton, etc. can be used.

[0304] In addition, as the π-electron deficient skeleton, a xanthene skeleton, a thioxanthene dioxide skeleton, an oxadiazole skeleton, a triazole skeleton, an imidazole skeleton, an anthraquinone skeleton, a boron-containing skeleton such as phenylborane or borantrene, an aromatic ring or a heteroaromatic ring having a nitrile group or a cyano group such as benzonitrile or cyanobenzene, a carbonyl skeleton such as benzophenone, a phosphine oxide skeleton, a sulfone skeleton, etc. can be used.

[0305] Thus, a π-electron deficient skeleton and a π-electron rich skeleton can be used instead of at least one of the π-electron deficient heteroaromatic ring and the π-electron rich heteroaromatic ring.

[0306] Note that a TADF material is a material having a function in which the difference between the S1 level and the T1 level is small and energy can be converted from the triplet excitation energy to the singlet excitation energy by reverse intersystem crossing. Therefore, up-conversion (reverse intersystem crossing) of the triplet excitation energy to the singlet excitation energy is possible with a small amount of thermal energy, and the singlet excited state can be efficiently generated. In addition, the triplet excitation energy can be converted into light emission.

[0307] In addition, an exciplex (also called an exciplex, an exiplex or an exciplex) that forms an excited state with two kinds of substances has a function as a TADF material in which the difference between the S1 level and the T1 level is extremely small and the triplet excitation energy can be converted into the singlet excitation energy.

[0308] Note that as an index of the T1 level, a phosphorescence spectrum observed at a low temperature (for example, from 77K to 10K) may be used. As a TADF material, when a tangent is drawn at the trailing edge on the short wavelength side of its fluorescence spectrum and the energy of the wavelength of the extrapolated line is taken as the S1 level, and a tangent is drawn at the trailing edge on the short wavelength side of the phosphorescence spectrum and the energy of the wavelength of the extrapolated line is taken as the T1 level, it is preferable that the difference between S1 and T1 is 0.3 eV or less, and more preferably 0.2 eV or less.

[0309] When using a TADF material as a luminescent substance, it is preferable that the S1 level of the host material is higher than the S1 level of the TADF material. Further, it is preferable that the T1 level of the host material is higher than the T1 level of the TADF material.

[0310] Note that this embodiment can be appropriately combined with other embodiments described in this specification.

[0311] (Embodiment 6) In this embodiment, the configuration of the photoelectric conversion device according to one aspect of the present invention will be described with reference to FIG. 3B.

[0312] <Configuration example of photoelectric conversion device> The photoelectric conversion device 150PD described in this embodiment includes an electrode 101, an electrode 102, and a unit 103PD (see FIG. 3B). Note that the electrode 102 includes a region overlapping with the electrode 101.

[0313] <<Configuration example 1 of unit 103PD>> The unit 103PD includes a region sandwiched between the electrode 101 and the electrode 102, and the unit 103PD includes a donor material, an acceptor material, and a carrier transporting material. The unit 103PD has a function of converting irradiated light into electric power.

[0314] For example, the compound described in Embodiment 1 can be used as the carrier transporting material. Specifically, it can be used for a material having hole transporting properties.

[0315] Note that this embodiment can be appropriately combined with other embodiments described in this specification.

[0316] (Embodiment 7) In this embodiment, a light emitting device using the light emitting device described in any one of Embodiments 2 to 5 will be described.

[0317] In this embodiment, a light-emitting device manufactured using the light-emitting device described in any one of Embodiments 2 to 5 will be described with reference to FIG. 4. Note that FIG. 4A is a top view showing the light-emitting device, and FIG. 4B is a cross-sectional view obtained by cutting FIG. 4A along A-B and C-D. This light-emitting device includes a drive circuit section (source line drive circuit 601) indicated by a dotted line, a pixel section 602, and a drive circuit section (gate line drive circuit 603) as means for controlling the light emission of the light-emitting device. Further, 604 is a sealing substrate, and 605 is a sealing material. The inside surrounded by the sealing material 605 is a space 607.

[0318] Note that the routing wiring 608 is wiring for transmitting signals input to the source line drive circuit 601 and the gate line drive circuit 603, and receives a video signal, a clock signal, a start signal, a reset signal, etc. from an FPC (Flexible Printed Circuit) 609 which is an external input terminal. Although only the FPC is illustrated here, a printed wiring board (PWB) may be attached to this FPC. The light-emitting device in this specification includes not only the light-emitting device main body but also a state in which an FPC or a PWB is attached thereto.

[0319] Next, the cross-sectional structure will be described with reference to FIG. 4B. Although a drive circuit section and a pixel section are formed on the element substrate 610, here, the source line drive circuit 601 which is a drive circuit section and one pixel in the pixel section 602 are shown.

[0320] The element substrate 610 may be made of a substrate such as glass, quartz, organic resin, metal, alloy, semiconductor, or a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (polyvinyl fluoride), polyester, or acrylic resin.

[0321] The structure of the transistor used for the pixel and the driving circuit is not particularly limited. For example, it may be an inverted staggered transistor or a staggered transistor. Also, it may be a top gate transistor or a bottom gate transistor. The semiconductor material used for the transistor is not particularly limited, and 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 based metal oxide, may be used.

[0322] The crystallinity of the semiconductor material used for the transistor is also not particularly limited, and any of an amorphous semiconductor, a semiconductor having crystallinity (microcrystalline semiconductor, polycrystalline semiconductor, single crystal semiconductor, or a semiconductor having a crystal region in part) may be used. Using a semiconductor having crystallinity is preferable because deterioration of transistor characteristics can be suppressed.

[0323] Here, in addition to the transistors provided in the above pixel and driving circuit, for semiconductor devices such as transistors used for a touch sensor described later, it is preferable to apply an oxide semiconductor. In particular, it is preferable to apply an oxide semiconductor having a wider bandgap than silicon. By using an oxide semiconductor having a wider bandgap than silicon, the current in the off state of the transistor can be reduced.

[0324] The above oxide semiconductor preferably contains at least indium (In) or zinc (Zn). Also, it is more preferable that it is an oxide semiconductor containing an oxide represented by In-M-Zn based oxide (M is a metal such as Al, Ti, Ga, Ge, Y, Zr, Sn, La, Ce, or Hf).

[0325] In particular, as the semiconductor layer, it is preferable to use an oxide semiconductor film having a plurality of crystal parts, where the c-axis of the crystal part is oriented perpendicular to the surface to be formed of the semiconductor layer or the upper surface of the semiconductor layer, and there is no grain boundary between adjacent crystal parts.

[0326] By using such a material as the semiconductor layer, fluctuations in electrical characteristics can be suppressed, and a highly reliable transistor can be realized.

[0327] In addition, due to its low off-current, the transistor having the above-described semiconductor layer can hold the charge accumulated in the capacitor through the transistor for a long period of time. By applying such a transistor to a pixel, it is also possible to stop the drive circuit while maintaining the gradation of the image displayed in each display area. As a result, an electronic device with extremely low power consumption can be realized.

[0328] For the purpose of stabilizing the characteristics of the transistor, etc., it is preferable to provide an underlying film. As the underlying film, an inorganic insulating film such as a silicon oxide film, a silicon nitride film, a silicon oxynitride film, or a silicon nitride oxide film can be used, and it can be formed as a single layer or by lamination. The underlying film can be formed using a sputtering method, a CVD (Chemical Vapor Deposition) method (such as a plasma CVD method, a thermal CVD method, an MOCVD (Metal Organic CVD) method, etc.), an ALD (Atomic Layer Deposition) method, a coating method, a printing method, etc. Note that the underlying film may not be provided if not necessary.

[0329] Note that FET623 indicates one of the transistors formed in the source line drive circuit 601. Also, the drive circuit may be formed of various CMOS circuits, PMOS circuits, or NMOS circuits. In the present embodiment, a driver integrated type in which the drive circuit is formed on the substrate is shown, but this is not necessarily required, and the drive circuit can also be formed outside the substrate instead of on the substrate.

[0330] In addition, the pixel portion 602 is formed of a plurality of pixels including a switching FET611, a current control FET612, and a first electrode 613 electrically connected to the drain thereof, but is not limited thereto, and a pixel portion combining three or more FETs and a capacitor element may be used.

[0331] Note that an insulator 614 is formed to cover the end portion of the first electrode 613. Here, it can be formed by using a positive photosensitive acrylic resin film.

[0332] Also, in order to make the coating property of the EL layer or the like formed later good, a curved surface having a curvature is formed at the upper end portion or the lower end portion of the insulator 614. For example, when a positive photosensitive acrylic resin is used as the material of the insulator 614, it is preferable to provide a curved surface having a radius of curvature (0.2 μm or more and 3 μm or less) only at the upper end portion of the insulator 614. Further, as the insulator 614, either a negative photosensitive resin or a positive photosensitive resin can be used.

[0333] An EL layer 616 and a second electrode 617 are respectively formed on the first electrode 613. Here, as the material used for the first electrode 613 that functions as an anode, it is desirable to use a material having a large work function. For example, in addition to single-layer films such as an ITO film, an indium tin oxide film containing silicon, an indium oxide film containing 2 wt% or more and 20 wt% or less of zinc oxide, a titanium nitride film, a chromium film, a tungsten film, a Zn film, and a Pt film, a laminate of a titanium nitride film and a film mainly composed of aluminum, a three-layer structure of a titanium nitride film, a film mainly composed of aluminum, and a titanium nitride film can be used. Note that when a laminated structure is used, the resistance as a wiring is low, good ohmic contact can be achieved, and it can further function as an anode.

[0334] Also, the EL layer 616 is formed by various methods such as a vapor deposition method using a vapor deposition mask, an inkjet method, and a spin coating method. The EL layer 616 includes a configuration as described in any one of Embodiments 2 to 5. Further, as other materials constituting the EL layer 616, a low molecular compound or a high molecular compound (including an oligomer and a dendrimer) may be used.

[0335] Furthermore, as the material used for the second electrode 617 formed on the EL layer 616 and functioning as a cathode, it is preferable to use a material with a small work function (Al, Mg, Li, Ca, or their alloys or compounds (MgAg, MgIn, AlLi, etc.)). When the light generated in the EL layer 616 is transmitted through the second electrode 617, it is good to use a laminate of a thin metal film with a reduced film thickness and a transparent conductive film (ITO, indium oxide containing 2 wt% or more and 20 wt% or less of zinc oxide, indium tin oxide containing silicon, zinc oxide (ZnO), etc.) as the second electrode 617.

[0336] Note that a light-emitting device 618 is formed by the first electrode 613, the EL layer 616, and the second electrode 617. The light-emitting device is the light-emitting device described in any one of Embodiments 2 to 5. Note that although a plurality of light-emitting devices are formed in the pixel portion, in the light-emitting device of this embodiment, both the light-emitting device described in any one of Embodiments 2 to 5 and a light-emitting device having other configurations may be mixed.

[0337] Furthermore, by bonding the sealing substrate 604 to the element substrate 610 with the sealing material 605, a structure is formed in which the light-emitting device 618 is provided in a space 607 surrounded by the element substrate 610, the sealing substrate 604, and the sealing material 605. Note that the space 607 is filled with a filling material, and in addition to the case where an inert gas (nitrogen, argon, etc.) is filled, it may also be filled with a sealing material. It is a preferable configuration to form a recess in the sealing substrate and provide a drying material therein to suppress deterioration due to the influence of moisture.

[0338] Note that it is preferable to use an epoxy-based resin or glass frit for the sealing material 605. Also, these materials are desirably materials that do not transmit moisture and oxygen as much as possible. In addition to a glass substrate or a quartz substrate, a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (polyvinyl fluoride), polyester, acrylic resin, or the like can be used as the material for the sealing substrate 604.

[0339] Although not shown in Fig. 4, a protective film may be provided on the second electrode. The protective film may be formed of an organic resin film or an inorganic insulating film. Further, the protective film may be formed so as to cover the exposed portion of the sealing material 605. Further, the protective film can be provided so as to cover the exposed side surfaces of the surfaces and side surfaces of the pair of substrates, the sealing layer, the insulating layer, etc.

[0340] For the protective film, a material that is less permeable to impurities such as water can be used. Therefore, it is possible to effectively suppress the diffusion of impurities such as water from the outside to the inside.

[0341] As the material constituting the protective film, oxides, nitrides, fluorides, sulfides, ternary compounds, metals, polymers, etc. can be used. 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, etc., materials containing aluminum nitride, hafnium nitride, silicon nitride, tantalum nitride, titanium nitride, niobium nitride, molybdenum nitride, zirconium nitride or gallium nitride, etc., materials containing 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, etc. can be used.

[0342] The protective film is preferably formed using a film-forming method with good step coverage. One such method is the atomic layer deposition (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, a protective film that is dense, has reduced defects such as cracks and pinholes, or has a uniform thickness can be formed. Also, the damage to the processing member when forming the protective film can be reduced.

[0343] For example, by forming the protective film using the ALD method, a protective film that is uniform and has few defects can be formed on a surface with a complex uneven shape, or on the upper, side, and back surfaces of a touch panel.

[0344] As described above, a light-emitting device manufactured using the light-emitting device according to any one of Embodiments 2 to 5 can be obtained.

[0345] Since the light-emitting device in the present embodiment uses the light-emitting device according to any one of Embodiments 2 to 5, a light-emitting device with good characteristics can be obtained. Specifically, since the light-emitting device according to any one of Embodiments 2 to 5 has good luminous efficiency, it is possible to make a light-emitting device with low power consumption.

[0346] FIG. 5 shows an example of a light-emitting device in which a light-emitting device that exhibits white light emission is formed and colorized by providing a coloring layer (color filter) or the like. FIG. 5A shows a substrate 1001, an underlying insulating film 1002, a gate insulating film 1003, gate electrodes 1006, 1007, 1008, a first interlayer insulating film 1020, a second interlayer insulating film 1021, a peripheral portion 1042, a pixel portion 1040, a driving circuit portion 1041, first electrodes 1024W, 1024R, 1024G, 1024B of the light-emitting device, a partition wall 1025, an EL layer 1028, a second electrode 1029 of the light-emitting device, a sealing substrate 1031, a sealing material 1032, etc.

[0347] In addition, in FIG. 5A, the colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B) are provided on the transparent substrate 1033. A black matrix 1035 may be further provided. The transparent substrate 1033 provided with the colored layers and the black matrix is aligned and fixed to the substrate 1001. Note that the colored layers and the black matrix 1035 are covered with an overcoat layer 1036. In FIG. 5A, there are a light-emitting layer that does not transmit light through the colored layer to the outside and a light-emitting layer that transmits light through each colored layer to the outside. Since the light that does not transmit through the colored layer is white, and the light that transmits through the colored layer is red, green, or blue, an image can be expressed with four-color pixels.

[0348] FIG. 5B shows an example in which the colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B) are formed between the gate insulating film 1003 and the first interlayer insulating film 1020. In this way, the colored layers may be provided between the substrate 1001 and the sealing substrate 1031.

[0349] In addition, in the light-emitting device described above, a light-emitting device having a structure in which light is extracted from the side of the substrate 1001 on which the FET is formed (bottom emission type) is used. However, a light-emitting device having a structure in which light is extracted from the side of the sealing substrate 1031 (top emission type) may be used. A cross-sectional view of the top emission type light-emitting device is shown in FIG. 6. In this case, a substrate that does not transmit light can be used as the substrate 1001. Until a connection electrode connecting the FET and the anode of the light-emitting device is formed, it is formed in the same manner as the bottom emission type light-emitting device. Thereafter, a third interlayer insulating film 1037 is formed to cover the electrode 1022. This insulating film may serve as a planarization film. The third interlayer insulating film 1037 can be formed using other known materials in addition to the same material as the second interlayer insulating film.

[0350] The first electrodes 1024W, 1024R, 1024G, and 1024B of the light-emitting device are anodes here, but they may also be cathodes. Further, in the case of a top-emission type light-emitting device as shown in FIG. 6, it is preferable that the first electrode is a reflective electrode. The configuration of the EL layer 1028 is the same as the configuration described as the unit 103 in any one of Embodiments 2 to 5, and the element structure is such that white light emission can be obtained.

[0351] In the top-emission structure as shown in FIG. 6, sealing can be performed with a sealing substrate 1031 provided with a coloring layer (red coloring layer 1034R, green coloring layer 1034G, blue coloring layer 1034B). A black matrix 1035 may be provided on the sealing substrate 1031 so as to be located between pixels. The coloring layer (red coloring layer 1034R, green coloring layer 1034G, blue coloring layer 1034B) and the black matrix may be covered with an overcoat layer 1036. Note that the sealing substrate 1031 uses a substrate having translucency. Here, an example of full-color display using four colors of red, green, blue, and white is shown, but it is not particularly limited, and full-color display may be performed using four colors of red, yellow, green, and blue or three colors of red, green, and blue.

[0352] In a top-emission type light-emitting device, application of a microcavity structure can be suitably performed. A light-emitting device having a microcavity structure is obtained by using a first electrode as a reflective electrode and a second electrode as a semi-transmissive / semi-reflective electrode. At least an EL layer is provided between the reflective electrode and the semi-transmissive / semi-reflective electrode, and at least a light-emitting layer serving as a light-emitting region is provided.

[0353] Note that the reflective electrode has a visible light reflectance of 40% to 100%, preferably 70% to 100%, and its resistivity is 1×10 -2 Ω·cm or less. Also, the semi-transmissive / semi-reflective electrode has a visible light reflectance of 20% to 80%, preferably 40% to 70%, and its resistivity is 1×10 -2 Ω·cm or less.

[0354] The light emitted from the light-emitting layer contained in the EL layer is reflected by the reflective electrode and the semi-transmissive / semi-reflective electrode and resonates.

[0355] By changing the thicknesses of the transparent conductive film, the above-described composite material, the carrier transport material, etc., the optical distance between the reflective electrode and the semi-transmissive / semi-reflective electrode can be changed. Thereby, between the reflective electrode and the semi-transmissive / semi-reflective electrode, light of a resonant wavelength can be enhanced and light of a non-resonant wavelength can be attenuated.

[0356] Note that since the light (first reflected light) reflected by the reflective electrode and returning causes significant interference with the light (first incident light) directly incident from the light-emitting layer to the semi-transmissive / semi-reflective electrode, it is preferable to adjust the optical distance between the reflective electrode and the light-emitting layer to (2n - 1)λ / 4 (where n is a natural number of 1 or more and λ is the wavelength of the light to be amplified). By adjusting the optical distance, the phases of the first reflected light and the first incident light can be matched and the light emission from the light-emitting layer can be further amplified.

[0357] In the above configuration, the EL layer may have a structure having a plurality of light-emitting layers or a structure having a single light-emitting layer. For example, in combination with the configuration of the tandem type light-emitting device described above, a plurality of EL layers are provided with a charge generation layer sandwiched between them in one light-emitting device, and a configuration in which a single or a plurality of light-emitting layers are formed in each EL layer may be applied.

[0358] By having a microcavity structure, it becomes possible to enhance the light emission intensity in the front direction of a specific wavelength, so that power consumption can be reduced. In the case of a light-emitting device that displays an image with four sub-pixels of red, yellow, green, and blue, in addition to the luminance improvement effect by yellow light emission, a microcavity structure adapted to the wavelength of each color can be applied to all the sub-pixels, so that a light-emitting device with good characteristics can be obtained.

[0359] Since the light-emitting device according to this embodiment uses the light-emitting device described in any one of Embodiments 2 to 5, a light-emitting device having good characteristics can be obtained. Specifically, since the light-emitting device described in any one of Embodiments 2 to 5 has good luminous efficiency, it is possible to obtain a light-emitting device with low power consumption.

[0360] So far, the active matrix type light-emitting device has been described. Hereinafter, the passive matrix type light-emitting device will be described. FIG. 7 shows a passive matrix type light-emitting device manufactured by applying the present invention. Note that FIG. 7A is a perspective view showing the light-emitting device, and FIG. 7B is a cross-sectional view obtained by cutting FIG. 7A along the X-Y plane. In FIG. 7, an EL layer 955 is provided between an electrode 952 and an electrode 956 on a substrate 951. The end of the electrode 952 is covered with an insulating layer 953. Then, a partition layer 954 is provided on the insulating layer 953. The side walls of the partition layer 954 have an inclination such that the distance between one side wall and the other side wall becomes narrower as it approaches the substrate surface. That is, the cross-section of the partition layer 954 in the short side direction is trapezoidal, and the bottom side (the side facing the same direction as the surface direction of the insulating layer 953 and in contact with the insulating layer 953) is shorter than the upper side (the 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 defects in the light-emitting device caused by static electricity or the like. Also, in the passive matrix type light-emitting device, the light-emitting device described in any one of Embodiments 2 to 5 is used, and a light-emitting device with good reliability or a light-emitting device with low power consumption can be obtained.

[0361] As described above, the light-emitting device can be suitably used as a display device for displaying an image because it is possible to control each of a large number of minute light-emitting devices arranged in a matrix.

[0362] Also, this embodiment can be freely combined with other embodiments.

[0363] (Embodiment 8) In this embodiment, an example of using the light-emitting device described in any one of Embodiments 2 to 5 as a lighting device will be described with reference to FIG. 8. FIG. 8B is a top view of the lighting device, and FIG. 8A is a cross-sectional view taken along the line e-f in FIG. 8B.

[0364] In the lighting device according to this embodiment, a first electrode 401 is formed on a translucent substrate 400 that is a support. The first electrode 401 corresponds to the electrode 101 in any one of Embodiments 2 to 5. When extracting light emission from the first electrode 401 side, the first electrode 401 is formed of a translucent material.

[0365] A pad 412 for supplying a voltage to the second electrode 404 is formed on the substrate 400.

[0366] An EL layer 403 is formed on the first electrode 401. The EL layer 403 includes the configuration of the unit 103 in any one of Embodiments 2 to 5. For these configurations, please refer to the relevant description.

[0367] The second electrode 404 is formed to cover the EL layer 403. The second electrode 404 corresponds to the electrode 102 in any one of Embodiments 2 to 5. When extracting light emission from the first electrode 401 side, the second electrode 404 is formed of a material with high reflectivity. The second electrode 404 is connected to the pad 412 to supply a voltage.

[0368] As described above, the lighting device in this embodiment has a light-emitting device having a first electrode 401, an EL layer 403, and a second electrode 404. Since the light-emitting device has high luminous efficiency, the lighting device in this embodiment can be a lighting device with low power consumption.

[0369] A substrate 400 on which a light-emitting device having the above configuration is formed and a sealing substrate 407 are fixed and sealed using sealing materials 405 and 406, thereby completing the lighting device. Either of the sealing materials 405 and 406 may be used. Also, a desiccant can be mixed into the inner sealing material 406 (not shown in FIG. 8B), whereby moisture can be adsorbed, leading to an improvement in reliability.

[0370] Further, by extending a part of the pad 412 and the first electrode 401 outside the sealing materials 405 and 406, an external input terminal can be formed. Also, an IC chip 420 or the like on which a converter or the like is mounted may be provided thereon.

[0371] As described above, the lighting device according to the present embodiment uses the light-emitting device described in any one of Embodiments 2 to 5 for the EL element, and can be a lighting device with low power consumption.

[0372] (Embodiment 9) In the present embodiment, an example of an electronic device including, in a part thereof, the light-emitting device described in any one of Embodiments 2 to 5 will be described. The light-emitting device described in any one of Embodiments 2 to 5 is a light-emitting device with good luminous efficiency and low power consumption. As a result, the electronic device described in the present embodiment can be an electronic device having a light-emitting portion with low power consumption.

[0373] Examples of electronic devices to which the above light-emitting device is applied include, for example, a television device (also referred to as a TV or a television receiver), a monitor for a computer, a digital camera, a digital video camera, a digital photo frame, a mobile phone (also referred to as a cellular phone or a mobile phone device), a portable game machine, a portable information terminal, an audio playback device, and a large game machine such as a pachinko machine. Specific examples of these electronic devices are shown below.

[0374] FIG. 9A shows an example of a television apparatus. In the television apparatus, a display unit 7103 is incorporated in a housing 7101. Here, a configuration is shown in which the housing 7101 is supported by a stand 7105. The display unit 7103 can display an image, and the display unit 7103 is configured by arranging the light-emitting devices described in any one of Embodiments 2 to 5 in a matrix.

[0375] The operation of the television apparatus can be performed by an operation switch provided in the housing 7101 or a separate remote control operation unit 7110. Channel and volume operations can be performed by operation keys 7109 provided in the remote control operation unit 7110, and the image displayed on the display unit 7103 can be operated. Further, the remote control operation unit 7110 may be configured to include a display unit 7107 that displays information output from the remote control operation unit 7110.

[0376] Note that the television apparatus is configured to include a receiver, a modem, and the like. The receiver can receive general television broadcasts, and further, by connecting to a communication network by wire or wirelessly via the modem, one-way (from a sender to a receiver) or two-way (between a sender and a receiver, or between receivers) information communication can also be performed.

[0377] FIG. 9B1 is a computer, including a main body 7201, a housing 7202, a display unit 7203, a keyboard 7204, an external connection port 7205, a pointing device 7206, etc. Note that this computer is manufactured by arranging the light-emitting devices described in any one of Embodiments 2 to 5 in a matrix and using them for the display unit 7203. The computer in FIG. 9B1 may be in the form shown in FIG. 9B2. In the computer of FIG. 9B2, a second display unit 7210 is provided instead of the keyboard 7204 and the pointing device 7206. The second display unit 7210 is a touch panel type, 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, the second display unit 7210 can display not only input displays but also other images. Also, the display unit 7203 may be a touch panel. By connecting the two screens with a hinge, it is possible to prevent problems such as damage to the screens during storage or transportation.

[0378] FIG. 9C shows an example of a mobile terminal. The mobile phone includes, in addition to a display unit 7402 incorporated in a housing 7401, operation buttons 7403, an external connection port 7404, a speaker 7405, a microphone 7406, etc. Note that the mobile phone has a display unit 7402 manufactured by arranging the light-emitting devices described in any one of Embodiments 2 to 5 in a matrix.

[0379] The mobile terminal shown in FIG. 9C can also be configured such that information can be input by touching the display unit 7402 with a finger or the like. In this case, operations such as making a call or creating an email can be performed by touching the display unit 7402 with a finger or the like.

[0380] The screen of the display unit 7402 mainly has three modes. The first is a display mode mainly for displaying images, the second is an input mode mainly for inputting information such as characters, and the third is a display + input mode in which the two modes of the display mode and the input mode are mixed.

[0381] For example, when making a phone call or creating an email, the display unit 7402 may be set to a character input mode mainly for character input, and an input operation for the characters displayed on the screen may be performed. In this case, it is preferable to display a keyboard or number buttons on most of the screen of the display unit 7402.

[0382] In addition, by providing a detection device having sensors such as a gyro and an acceleration sensor inside the mobile terminal, the orientation (portrait or landscape) of the mobile terminal can be determined, and the screen display of the display unit 7402 can be automatically switched.

[0383] Also, the switching of the screen mode is performed by touching the display unit 7402 or operating the operation button 7403 of the housing 7401. It can also be switched according to 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 is switched to the display mode, and if it is text data, it is switched to the input mode.

[0384] In addition, in the input mode, the signal detected by the optical sensor of the display unit 7402 is detected, and when there is no input by touch operation of the display unit 7402 for a certain period, the screen mode may be controlled to be switched from the input mode to the display mode.

[0385] The display unit 7402 can also function as an image sensor. For example, by touching the display unit 7402 with a palm or finger and imaging palm prints, fingerprints, etc., personal authentication can be performed. Also, if a backlight that emits near-infrared light or a sensing light source that emits near-infrared light is used for the display unit, finger veins, palm veins, etc. can also be imaged.

[0386] FIG. 10A is a schematic diagram showing an example of a cleaning robot.

[0387] The cleaning robot 5100 has a display 5101 arranged on the upper surface, a plurality of cameras 5102, a brush 5103, and operation buttons 5104 arranged on the side surface. Although not shown, the lower surface of the cleaning robot 5100 is provided with tires, a suction port, and the like. The cleaning robot 5100 is also provided with various sensors such as an infrared sensor, an ultrasonic sensor, an acceleration sensor, a piezo sensor, a light sensor, and a gyro sensor. In addition, the cleaning robot 5100 is provided with wireless communication means.

[0388] The cleaning robot 5100 can move automatically, detect dust 5120, and suck the dust from the suction port provided on the lower surface.

[0389] In addition, the cleaning robot 5100 can analyze the image captured by the camera 5102 and determine the presence or absence of obstacles such as walls, furniture, or steps. Also, when an object that is likely to get caught in the brush 5103, such as wiring, is detected by image analysis, the rotation of the brush 5103 can be stopped.

[0390] The display 5101 can display the remaining battery level, the amount of sucked dust, etc. The path traveled by the cleaning robot 5100 may be displayed on the display 5101. Also, the display 5101 may be a touch panel, and the operation buttons 5104 may be provided on the display 5101.

[0391] The cleaning robot 5100 can communicate with a portable electronic device 5140 such as a smartphone. The image captured by the camera 5102 can be displayed on the portable electronic device 5140. Therefore, the owner of the cleaning robot 5100 can know the state of the room even when away from home. Also, the display on the display 5101 can be confirmed on a portable electronic device such as a smartphone.

[0392] The light-emitting device according to one aspect of the present invention can be used for the display 5101.

[0393] The robot 2100 shown in FIG. 10B includes an arithmetic unit 2110, an illuminance sensor 2101, a microphone 2102, an upper camera 2103, a speaker 2104, a display 2105, a lower camera 2106, an obstacle sensor 2107, and a moving mechanism 2108.

[0394] The microphone 2102 has a function of detecting the user's voice, ambient sound, etc. Also, the speaker 2104 has a function of emitting sound. The robot 2100 can communicate with the user using the microphone 2102 and the speaker 2104.

[0395] The display 2105 has a function of displaying various 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. Also, the display 2105 may be a removable information terminal, and by installing it at a fixed position of the robot 2100, charging and data transfer are made possible.

[0396] The upper camera 2103 and the lower camera 2106 have a function of imaging the surroundings of the robot 2100. Also, the obstacle sensor 2107 can detect the presence or absence of obstacles in the traveling direction when the robot 2100 moves forward using the moving mechanism 2108. The robot 2100 can recognize the surrounding environment and move safely using the upper camera 2103, the lower camera 2106, and the obstacle sensor 2107. The light-emitting device according to one aspect of the present invention can be used for the display 2105.

[0397] FIG. 10C is a diagram showing an example of a goggle-type display. The goggle-type display includes, for example, a housing 5000, a display unit 5001, a speaker 5003, an LED lamp 5004, a connection terminal 5006, a sensor 5007 (including a function of measuring force, displacement, position, speed, acceleration, angular velocity, rotational speed, distance, light, liquid, magnetism, temperature, chemical substance, voice, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays), a microphone 5008, a display unit 5002, a support unit 5012, earphones 5013, and the like.

[0398] The light-emitting device according to one aspect of the present invention can be used for the display unit 5001 and the display unit 5002.

[0399] FIG. 11 is an example in which the light-emitting device described in any one of Embodiments 2 to 5 is used in an electric stand which is a lighting device. The electric stand shown in FIG. 11 has a housing 2001 and a light source 2002, and as the light source 2002, the lighting device described in Embodiment 3 may be used.

[0400] FIG. 12 is an example in which the light-emitting device described in any one of Embodiments 2 to 5 is used as an indoor lighting device 3001. Since the light-emitting device described in any one of Embodiments 2 to 5 is a light-emitting device with high luminous efficiency, it can be made into a lighting device with low power consumption. In addition, since the light-emitting device described in any one of Embodiments 2 to 5 can be made into a large area, it can be used as a large-area lighting device. Further, since the light-emitting device described in any one of Embodiments 2 to 5 is thin, it can be used as a thin lighting device.

[0401] The light-emitting device according to any one of Embodiments 2 to 5 can also be mounted on the windshield or dashboard of an automobile. FIG. 13 shows an aspect in which the light-emitting device according to any one of Embodiments 2 to 5 is used for the windshield or dashboard of an automobile. The display areas 5200 to 5203 are display areas provided using the light-emitting device according to any one of Embodiments 2 to 5.

[0402] The display area 5200 and the display area 5201 are display devices equipped with the light-emitting device according to any one of Embodiments 2 to 5 provided on the windshield of an automobile. The light-emitting device according to any one of Embodiments 2 to 5 can be made into a so-called see-through display device where the opposite side can be seen through by fabricating the first electrode and the second electrode with light-transmissive electrodes. In the case of a see-through display, even if it is installed on the windshield of an automobile, it can be installed without obstructing the view. When providing transistors or the like for driving, it is preferable to use light-transmissive transistors such as organic transistors made of organic semiconductor materials or transistors using oxide semiconductors.

[0403] The display area 5202 is a display device equipped with the light-emitting device according to any one of Embodiments 2 to 5 provided on the pillar portion. By projecting the video from the imaging means provided on the vehicle body onto the display area 5202, the view blocked by the pillar can be complemented. Similarly, the display area 5203 provided on the dashboard portion can complement the view blocked by the vehicle body by projecting the video from the imaging means provided outside the automobile, filling in the blind spots and enhancing safety. By projecting the video so as to complement the invisible parts, safety confirmation can be performed more naturally without a sense of discomfort.

[0404] The display area 5203 can also provide various information by displaying navigation information, speedometer, engine speed, odometer, fuel gauge, gear state, air conditioning settings, etc. The display can be appropriately changed in terms of its display items and layout according to the user's preference. Note that these information can also be provided in the display areas 5200 to 5202. In addition, the display areas 5200 to 5203 can also be used as lighting devices.

[0405] Also, FIGS. 14A to 14C show a foldable portable information terminal 9310. FIG. 14A shows the portable information terminal 9310 in the unfolded state. FIG. 14B shows the portable information terminal 9310 in a state during the change from one of the unfolded state or the folded state to the other. FIG. 14C shows the portable information terminal 9310 in the folded state. The portable information terminal 9310 has excellent portability in the folded state and excellent display listability due to a seamless and wide display area in the unfolded state.

[0406] The display panel 9311 is supported by three housings 9315 connected by a hinge 9313. Note that the display panel 9311 may be a touch panel (input / output device) equipped with a touch sensor (input device). Also, the display panel 9311 can be reversibly deformed from the unfolded state to the folded state of the portable information terminal 9310 by bending between the two housings 9315 via the hinge 9313. The light-emitting device according to one aspect of the present invention can be used for the display panel 9311.

[0407] Note that the configuration shown in this embodiment can be used by appropriately combining the configurations shown in Embodiments 2 to 5.

[0408] As described above, the application range of the light-emitting device including the light-emitting device described in any one of Embodiments 2 to 5 is extremely wide, 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 5, an electronic device with low power consumption can be obtained.

[0409] Note that this embodiment can be appropriately combined with other embodiments described in this specification.

Example

[0410] (Synthesis Example 1) In this example, the physical properties and synthesis method of the organic compound according to one aspect of the present invention will be described with reference to FIGS. 15 to 17. Specifically, the properties and synthesis method of N,N'-bis(9-phenyl-9H-carbazol-2-yl)-N,N'-diphenyldibenzothieno[2,3-f;5,4-f']bisbenzothiophene-3,10-diamine (abbreviation: PCA2Dfbf-02), which is represented by the structural formula (112) in Embodiment 1, will be described. The structural formula of PCA2Dfbf-02 is shown below.

[0411]

Chemical formula

[0412] FIG. 15 is a diagram for explaining the absorption spectrum and emission spectrum of a toluene solution containing PCA2Dfbf-02.

[0413] FIG. 16 is a diagram for explaining the absorption spectrum and emission spectrum of solid thin-film PCA2Dfbf-02.

[0414] FIGS. 17A and 17B are diagrams for explaining the 1 1H NMR spectrum of PCA2Dfbf-02.

[0415] <Measurement apparatus and method for preparing measurement sample> The absorption spectrum of the toluene solution was measured using an ultraviolet-visible spectrophotometer (model V550 manufactured by JASCO Corporation), and the absorption spectrum derived from toluene was subtracted.

[0416] The absorption spectrum of the solid thin-film sample was measured using a spectrophotometer (spectrophotometer U4100 manufactured by Hitachi High-Technologies Corporation).

[0417] The emission spectrum was measured using a fluorescence photometer (FS920 manufactured by Hamamatsu Photonics K.K.), and the quantum yield was measured using an absolute PL quantum yield measurement device (Quantaurus-QY manufactured by Hamamatsu Photonics K.K.).

[0418] The thin-film solid sample was formed on a quartz substrate using a vacuum evaporation method.

[0419] <Physical properties> The absorption spectrum of the toluene solution containing PCA2Dfbf-02 had peaks at 430 nm, 409 nm, 347 nm, and 281 nm (see Fig. 15). The emission spectrum had peaks at 446 nm and 477 nm, and the intensity at 477 nm was 1 / 2 or less of the intensity at 446 nm. The full width at half maximum was 25 nm. Note that light with a wavelength of 408 nm was used as the excitation light. The quantum yield in the toluene solution was 94%.

[0420] The molar absorption coefficient of the solution of PCA2Dfbf-02 was 1.3×10 5 (M -1 cm -1 ) at 430 nm. Therefore, it was found that the organic compound of one embodiment of the present invention exhibits a very high molar absorption coefficient.

[0421] The absorption spectrum of PCA2Dfbf-02 in the solid thin film had peaks at 436 nm, 416 nm, 352 nm, and 266 nm (see Fig. 16). The emission spectrum had peaks at 469 nm and 493 nm. Note that light with a wavelength of 380 nm was used as the excitation light.

[0422] As a result, it was found that PCA2Dfbf-02 emits blue light. It was also found that it can be used as a host material for luminescent materials and fluorescent luminescent materials in the visible region. It was also found that the quantum yield is very high, the full width at half maximum of the emission spectrum is 30 nm or less, and it is suitable as a luminescent material.

[0423] <Synthesis method> The synthesis method of PCA2Dfbf-02 will be described. The synthesis scheme (SC3) is shown below.

[0424] [Chemical formula]

[0425] 1.0 g (2.5 mmol) of 3,10-dichlorodibenzo[b,b']fluor[2,3-f;5,4-f']bisbenzofuran, 2.1 g (6.2 mmol) of N,9-diphenyl-9H-carbazole-2-amine, 89 mg (0.25 mmol) of di(1-adamantyl)-n-butylphosphine, and 1.4 g (15 mmol) of sodium tert-butoxide were placed in a 200 mL three-necked flask. 25 mL of xylene was added to this mixture. The mixture was degassed by stirring under reduced pressure. 28 mg (49 μmol) of bis(dibenzylideneacetone)palladium(0) was added to this mixture, and it was stirred at 150 °C for 14 hours under a nitrogen stream.

[0426] After stirring, toluene was added to this mixture, and it was suction filtered through Florisil, Celite, and alumina, and the filtrate was concentrated to obtain a solid.

[0427] The obtained solid was purified by silica gel column chromatography (developing solvent: toluene:hexane = 2:3) to obtain a solid. Further, the obtained solid was reprecipitated with toluene / ethanol to obtain 2.0 g of a yellow solid with a yield of 81%.

[0428] Also, 1.1 g of the yellow solid was purified by sublimation using the train sublimation method. It was carried out by heating at 400 °C under the conditions of a pressure of 1.8×10 -2 Pa and an argon flow rate of 0 mL / min. After sublimation purification, 0.73 g of a yellow solid was obtained with a recovery rate of 68%.

[0429] 1 H NMR Of the dichloromethane solution of the obtained yellow solid 1 ​The 1H NMR spectra are shown in FIGS. 17A and 17B. Numerical data are shown below. From this, it was found that PCA2Dfbf-02 was obtained in this synthesis example. 1 1H NMR(CD 2 Cl 2 , 300 MHz): δ = 7.03 - 7.13 (m, 6H), 7.16 - 7.32 (m, 14H), 7.35 - 7.42 (m, 6H), 7.49 - 7.55 (m, 8H), 7.83 (d, J1 = 8.4 Hz, 2H), 7.97 (d, J1 = 0.6 Hz, 2H), 8.01 (d, J1 = 0.6 Hz, 2H), 8.06 - 8.11 (m, 4H).

[0430] (Synthesis Example 2) In this example, the physical properties and synthesis method of the organic compound of one aspect of the present invention will be described with reference to FIGS. 18 to 20. Specifically, the characteristics and synthesis method of N,N'-bis(dibenzofuran-3-yl)-N,N'-diphenyldibenz[b,b']furo[2,3-f;5,4-f']bisbenzofuran-3,10-diamine (abbreviation: FrA2Dfbf-02), which is represented by the structural formula (107) in Embodiment 1, will be described. The structural formula of FrA2Dfbf-02 is shown below.

[0431] [Chemical formula]

[0432] FIG. 18 is a diagram for explaining the absorption spectrum and emission spectrum of a toluene solution containing FrA2Dfbf-02.

[0433] FIG. 19 is a diagram for explaining the absorption spectrum and emission spectrum of solid thin-film FrA2Dfbf-02.

[0434] FIGS. 20A and 20B are diagrams for explaining the 1 1H NMR spectrum of FrA2Dfbf-02.

[0435] [Measuring Device and Method for Preparing Measurement Sample] The absorption spectrum of the toluene solution was measured using an ultraviolet-visible spectrophotometer (V550 type, manufactured by JASCO Corporation), and the absorption spectrum derived from toluene was subtracted.

[0436] The absorption spectrum of the solid thin-film sample was measured using a spectrophotometer (U4100, manufactured by Hitachi High-Technologies Corporation).

[0437] The emission spectrum was measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics K.K.), and the quantum yield was measured using an absolute PL quantum yield measurement device (Quantaurus-QY, manufactured by Hamamatsu Photonics K.K.).

[0438] The thin-film solid sample was formed on a quartz substrate using a vacuum evaporation method.

[0439] <Physical properties> The absorption spectrum of the toluene solution containing FrA2Dfbf-02 had peaks at 426 nm, 405 nm, 350 nm, 327 nm, and 280 nm (see Figure 18). Also, the emission spectrum had peaks at 440 nm and 468 nm, and the intensity at 468 nm was 1 / 2 or less of the intensity at 440 nm. Also, the full width at half maximum was 22 nm. Note that light with a wavelength of 400 nm was used as the excitation light. Also, the quantum yield in the toluene solution was 93%.

[0440] The absorption spectrum of FrA2Dfbf-02 in the solid thin film had peaks at 431 nm, 410 nm, 356 nm, 332 nm, and 296 nm (see Figure 19). Also, the emission spectrum had peaks at 460 nm and 501 nm. Note that light with a wavelength of 400 nm was used as the excitation light.

[0441] As a result, it was found that FrA2Dfbf-02 emits blue light. Also, it was found that it can be used as a host material for luminescent materials and fluorescent luminescent materials in the visible region. Also, the quantum yield is very high, the full width at half maximum of the emission spectrum is 30 nm or less, and it was found that it is suitable as a luminescent material.

[0442] <Synthesis method> The synthesis method of FrA2Dfbf-02 will be described. The synthesis scheme (SC4) is shown below.

[0443]

Chemical formula

[0444] 0.97 g (2.3 mmol) of 3,10-dichlorodibenzo[b,b’]fluoro[2,3-f;5,4-f’]bisbenzofuran, 1.5 g (5.8 mmol) of N-phenyldibenzofuran-3-amine, 83 mg (0.23 mmol) of di(1-adamantyl)-n-butylphosphine, and 1.3 g (14 mmol) of sodium tert-butoxide were placed in a 200 mL three-necked flask. 25 mL of xylene was added to this mixture. The mixture was degassed by stirring under reduced pressure. 27 mg (46 μmol) of bis(dibenzylideneacetone)palladium(0) was added to this mixture, and it was stirred at 150 °C for 20.5 hours under a nitrogen stream.

[0445] After stirring, toluene was added to this mixture, and it was suction filtered through Florisil, Celite, and alumina, and the filtrate was concentrated to obtain a solid.

[0446] The obtained solid was purified by silica gel column chromatography (developing solvent: toluene:hexane = 2:3) to obtain a solid. Further, the obtained solid was recrystallized from toluene to obtain 1.2 g of a yellow solid with a yield of 59%.

[0447] Also, 1.2 g of the yellow solid was sublimation-purified by the train sublimation method. It was carried out by heating at 385 °C under the conditions of a pressure of 2.6×10 -2 Pa and an argon flow rate of 0 mL / min. After sublimation purification, 0.95 g of a yellow solid was obtained with a recovery rate of 83%.

[0448] 1 1H NMR] ​The dichloromethane solution of the obtained yellow solid 1 The 1H NMR spectrum is shown in FIGS. 20A and 20B. The numerical data is shown below. From this, it was found that FrA2Dfbf-02 was obtained in this synthesis example. 1 1H NMR(CD 2 Cl 2 , 300 MHz): δ = 7.11 - 7.19 (m, 6H), 7.21 - 7.25 (m, 4H), 7.31 - 7.44 (m, 12H), 7.51 - 7.54 (m, 2H), 7.84 - 7.93 (m, 6H), 8.01 (d, J1 = 0.6 Hz, 2H), 8.04 (d, J1 = 0.6 Hz, 2H).

[0449] (Synthesis Example 3) In this example, the physical properties and synthesis method of the organic compound of one aspect of the present invention will be described with reference to FIGS. 21 to 23. Specifically, the characteristics and synthesis method of N,N'-bis(dibenzofuran-3-yl)-N,N'-di(4-tert-butylphenyl)dibenz[b,b']furo[2,3-f;5,4-f']bisbenzofuran-3,10-diamine (abbreviation: tBuFrA2Dfbf-02), which is represented by the structural formula (114) in Embodiment 1, will be described. The structural formula of tBuFrA2Dfbf-02 is shown below.

[0450] [Chemical formula]

[0451] FIG. 21 is a diagram for explaining the absorption spectrum and emission spectrum of a toluene solution containing tBuFrA2Dfbf-02.

[0452] FIG. 22 is a diagram for explaining the absorption spectrum and emission spectrum of solid thin-film tBuFrA2Dfbf-02.

[0453] FIGS. 23A and 23B are diagrams for explaining the 1 1H NMR spectrum of tBuFrA2Dfbf-02.

[0454] <Measuring Device and Method for Preparing Measurement Sample> The absorption spectrum of the toluene solution was measured using an ultraviolet-visible spectrophotometer (V550 type manufactured by JASCO Corporation), and the absorption spectrum derived from toluene was subtracted.

[0455] The absorption spectrum of the solid thin film sample was measured using a spectrophotometer (U4100 spectrophotometer manufactured by Hitachi High-Technologies Corporation).

[0456] The emission spectrum was measured using a fluorescence photometer (FP-8600 manufactured by JASCO Corporation), and the quantum yield was measured using an absolute PL quantum yield measuring device (Quantaurus-QY manufactured by Hamamatsu Photonics K.K.).

[0457] The thin film solid sample was formed on a quartz substrate using a vacuum evaporation method.

[0458] <Physical Properties> The absorption spectrum of the toluene solution containing tBuFrA2Dfbf-02 had peaks at 430 nm, 408 nm, 351 nm, and 329 nm (see Figure 21). Also, the emission spectrum had peaks at 444 nm and 472 nm, and the intensity at 472 nm was 1 / 2 or less of the intensity at 444 nm. The full width at half maximum was 23 nm. Note that light with a wavelength of 406 nm was used as the excitation light. Also, the quantum yield in the toluene solution was 92%.

[0459] The molar absorption coefficient of the solution of tBuFrA2Dfbf-02 was 1.4×10 5 (M -1 cm -1 ) at 426 nm. Therefore, it was found that the organic compound of one aspect of the present invention exhibits a very high molar absorption coefficient.

[0460] The absorption spectrum of the solid thin film of tBuFrA2Dfbf-02 had peaks at 434 nm, 412 nm, 356 nm, and 333 nm (see Fig. 22). Also, the emission spectrum had peaks at 461 nm, 489 nm, and 530 nm. Note that light with a wavelength of 400 nm was used as the excitation light.

[0461] As a result, it was found that tBuFrA2Dfbf-02 emits blue light. Also, it was found that it can be used as a host material for luminescent materials and fluorescent luminescent materials in the visible region. Also, the quantum yield was very high, the full width at half maximum of the emission spectrum was 30 nm or less, and it was found to be suitable as a luminescent material.

[0462] <Synthesis method> The synthesis method of tBuFrA2Dfbf-02 will be described. The synthesis scheme (SC5) is shown below.

[0463]

Chemical formula

[0464] 0.86 g (2.1 mmol) of 3,10-dichlorodibenzo[b,b']furo[2,3-f;5,4-f']bisbenzofuran, 1.6 g (5.1 mmol) of N-(4-tert-butylphenyl)dibenzofuran-3-amine, 74 mg (0.21 mmol) of di(1-adamantyl)-n-butylphosphine, and 1.2 g (12 mmol) of sodium tert-butoxide were placed in a 200 mL three-necked flask. 20 mL of xylene was added to this mixture. The mixture was degassed by stirring while reducing the pressure. 24 mg (41 μmol) of bis(dibenzylideneacetone)palladium(0) was added to this mixture, and the mixture was stirred at 150 °C for 29 hours under a nitrogen stream.

[0465] After stirring, water and ethanol were added to this mixture. After irradiating with ultrasonic waves, suction filtration was performed, and the filtrate was concentrated to recover the solid. The obtained solid was purified by silica gel column chromatography (developing solvent: toluene:hexane = 3:7) to obtain a solid. Further, the obtained solid was recrystallized twice with toluene to obtain 1.5 g of a yellow solid with a yield of 74%.

[0466] Also, 1.1 g of the yellow solid was purified by sublimation using the train sublimation method. It was carried out by heating at 385 °C under the conditions of a pressure of 2.5×10 -2 Pa and an argon flow rate of 0 mL / min. After sublimation purification, 0.91 g of the yellow solid was obtained with a recovery rate of 85%.

[0467] 1 1H NMR The 1 1H NMR spectrum of the dichloromethane solution of the obtained yellow solid is shown in FIGS. 23A and 23B. Also, the numerical data is shown below. From this, it was found that tBuFrA2Dfbf-02 was obtained in this synthesis example. 1 1H NMR(CD 2 Cl 2 , 300 MHz): δ = 1.35 (s, 18H), 7.14 - 7.19 (m, 8H), 7.29 - 7.44 (m, 12H), 7.45 - 7.53 (m, 2H), 7.83 - 7.92 (m, 6H), 8.00 (d, J1 = 0.9 Hz, 2H), 8.04 (d, J1 = 0.6 Hz, 2H).

Example

[0468] In this example, the structures, manufacturing methods, and characteristics of light-emitting devices 1 to 3 according to one aspect of the present invention will be described with reference to FIGS. 24, 25 to 31, and FIGS. 45 to 50.

[0469] FIG. 24 is a cross-sectional view for explaining the configuration of the manufactured light-emitting device.

[0470] FIG. 25 is a diagram for explaining the current density-luminance characteristics of light-emitting devices 1 to 3.​

[0471] Figure 26 is a diagram for explaining the luminance-current efficiency characteristics of light-emitting devices 1 to 3.

[0472] Figure 27 is a diagram for explaining the voltage-luminance characteristics of light-emitting devices 1 to 3.

[0473] Figure 28 is a diagram for explaining the voltage-current characteristics of light-emitting devices 1 to 3.

[0474] Figure 29 is a diagram for explaining the luminance-external quantum efficiency characteristics of light-emitting devices 1 to 3. Note that assuming the light distribution characteristics of the light-emitting device are of the Lambertian type, the external quantum efficiency was calculated from the luminance observed from the front and the emission spectrum.

[0475] Figure 30 is a diagram for explaining the emission spectrum when light-emitting devices 1 to 3 emit light at a luminance of 1000 cd / m 2 ².

[0476] Figure 31 is a diagram for explaining the difference in external quantum efficiency when light-emitting devices 1 to 3 emit light at a luminance of 1000 cd / m 2 ². Specifically, taking the external quantum efficiency of the light-emitting device with 1.5 wt% addition of the light-emitting material EM as 1, this is a diagram for comparing the external quantum efficiency of the light-emitting device with 3 wt% addition of the light-emitting material EM and the external quantum efficiency of the light-emitting device with 5 wt% addition of the light-emitting material EM.

[0477] Figure 45 is a diagram for explaining the current density-luminance characteristics of comparative light-emitting devices 1 to 3.

[0478] Figure 46 is a diagram for explaining the luminance-current efficiency characteristics of comparative light-emitting devices 1 to 3.

[0479] Figure 47 is a diagram for explaining the voltage-luminance characteristics of comparative light-emitting devices 1 to 3.

[0480] FIG. 48 is a diagram for explaining the voltage-current characteristics of Comparative Light-Emitting Devices 1 to 3.

[0481] FIG. 49 is a diagram for explaining the luminance-external quantum efficiency characteristics of Comparative Light-Emitting Devices 1 to 3. Note that assuming that the light distribution characteristics of the light-emitting device are of the Lambertian type, the external quantum efficiency was calculated from the luminance and emission spectrum observed from the front.

[0482] FIG. 50 is a diagram for explaining the emission spectrum when Comparative Light-Emitting Devices 1 to 3 are caused to emit light at a luminance of 1000 cd / m 2 ^2.

[0483] <Light-Emitting Devices 1 to 3> The fabricated Light-Emitting Devices 1 to 3 described in this embodiment have the same configuration as Light-Emitting Device 150 (see FIG. 24). Light-Emitting Device 150 has an electrode 101, an electrode 102, a unit 103, and a layer 104, and the electrode 102 has a region overlapping the electrode 101. Further, Light-Emitting Device 150 includes a layer 105.

[0484] The unit 103 has a region sandwiched between the electrode 101 and the electrode 102, and the unit 103 includes a layer 111, a layer 112, and a layer 113.

[0485] The layer 112 has a region sandwiched between the electrode 101 and the layer 111, and the layer 113 has a region sandwiched between the layer 111 and the electrode 102.

[0486] The layer 111 contains a light-emitting material EM. Note that in Light-Emitting Devices 1 to 3, tBuFrA2Dfbf-02 was used as the light-emitting material EM.

[0487] Layer 104 includes a material AM having acceptor properties and a material HT1. The material HT1 has a first HOMO level HOMO1, and the first HOMO level HOMO1 is -5.7 eV or more and -5.4 eV or less. In light-emitting devices 1 to 3, oFBiSF was used for the material HT1. Also, according to cyclic voltammetry (CV) measurement, the HOMO level of oFBiSF was -5.5 eV.

[0488] Layer 113 includes a material OMC, and the material OMC is an organometallic complex of an alkali metal or an organometallic complex of an alkaline earth metal. In light-emitting devices 1 to 3, Liq was used for the material OMC.

[0489] Layer 112 includes a region 112A and a region 112B. The region 112B includes a region sandwiched between the layer 111 and the region 112A, and the region 112B includes a material HT2. The material HT2 has a second HOMO level HOMO2, and the second HOMO level HOMO2 is in the range of -0.2 eV or more and 0 eV or less with respect to the first HOMO level HOMO1. In light-emitting devices 1 to 3, BBABnf was used for the material HT2. Also, according to cyclic voltammetry (CV) measurement, the HOMO level of BBABnf was -5.56 eV.

[0490] 《Configurations of Light-Emitting Devices 1 to 3》 The configurations of light-emitting devices 1 to 3 are shown in Table 1. Also, the structural formulas of the materials used in the light-emitting devices and comparative light-emitting devices described in this example are shown below.

[0491]

Table 1

[0492]

Chemical formula

[0493] 《Fabrication Methods of Light-Emitting Devices 1 to 3》 The light-emitting devices 1 to 3 described in this example were fabricated using a method having the following steps.

[0494] [First step] In the first step, the electrode 101 was formed. Specifically, it was formed by a sputtering method using indium tin oxide (ITSO) containing silicon or silicon oxide as a target.

[0495] Note that the electrode 101 contains ITSO, has a thickness of 70 nm, and has an area of 4 mm 2 (2 mm × 2 mm).

[0496] Next, the substrate on which the electrode 101 was formed was washed with water, baked at 200 °C for 1 hour, and then subjected to UV ozone treatment for 370 seconds. Then, the substrate was introduced into a vacuum evaporation apparatus whose internal pressure was reduced to about 10 -4 Pa, and vacuum baking was performed at 170 °C for 30 minutes in the heating chamber of the vacuum evaporation apparatus. Then, the substrate was allowed to cool for about 30 minutes.

[0497] [Second step] In the second step, the layer 104 was formed on the electrode 101. Specifically, the materials were co-evaporated using a resistance heating method.

[0498] Note that the layer 104 contains oFBiSF and an electron acceptor material (abbreviation: OCHD-001) at a ratio of oFBiSF:OCHD-001 = 1:0.1 (weight ratio) and has a thickness of 10 nm. Note that OCHD-001 has an acceptor property.

[0499] [Third step] In the third step, the region 112A was formed on the layer 104. Specifically, the materials were evaporated using a resistance heating method.

[0500] Note that the region 112A contains oFBiSF and has a thickness of 20 nm.

[0501] [Fourth step] In the fourth step, region 112B was formed on region 112A. Specifically, the material was vapor-deposited using a resistive heating method.

[0502] Note that region 112B contains BBABnf and has a thickness of 10 nm.

[0503] [Fifth step] In the fifth step, layer 111 was formed on region 112B. Specifically, the materials were co-vapor-deposited using a resistive heating method.

[0504] Note that layer 111 contains cgDBCzPA and tBuFrA2Dfbf-02 and has a thickness of 25 nm.

[0505] Specifically, in light-emitting device 1, layer 111 contains tBuFrA2Dfbf-02 at a ratio of cgDBCzPA:tBuFrA2Dfbf-02 = 1:0.015 (weight ratio); in light-emitting device 2, layer 111 contains tBuFrA2Dfbf-02 at a ratio of cgDBCzPA:tBuFrA2Dfbf-02 = 1:0.03 (weight ratio); and in light-emitting device 3, layer 111 contains tBuFrA2Dfbf-02 at a ratio of cgDBCzPA:tBuFrA2Dfbf-02 = 1:0.05 (weight ratio).

[0506] [Sixth step] In the sixth step, region 113A was formed on layer 111. Specifically, the material was vapor-deposited using a resistive heating method.

[0507] Note that region 113A contains 4-[3,5-bis(9H-carbazol-9-yl)phenyl]-2-phenyl-6-(1,1'-biphenyl-4-yl)pyrimidine (abbreviation: 6BP-4Cz2PPm) and has a thickness of 10 nm.

[0508] [Seventh step] In the seventh step, region 113B was formed on region 113A. Specifically, the materials were co-vapor-deposited using a resistive heating method.

[0509] Note that the region 113B contains 2-[3-(2,6-dimethyl-3-pyridinyl)-5-(9-phenanthrenyl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mPn-mDMePyPTzn) and Liq at a ratio of mPn-mDMePyPTzn:Liq = 1:1 (by weight) and has a thickness of 15 nm.

[0510] [Eighth step] In the eighth step, the layer 105 was formed on the region 113B. Specifically, the material was vapor-deposited using a resistance heating method.

[0511] Note that the layer 105 contains Liq and has a thickness of 1 nm.

[0512] [Ninth step] In the ninth step, the electrode 102 was formed on the layer 105. Specifically, the material was vapor-deposited using a resistance heating method.

[0513] Note that the electrode 102 contains Al and has a thickness of 200 nm.

[0514] 《Operating characteristics of light-emitting devices 1 to 3》 When power was supplied, the light-emitting devices 1 to 3 emitted light EL1 (see Fig. 24). The operating characteristics of the light-emitting devices 1 to 3 were measured (see Figs. 25 to 30). The measurements were performed at room temperature.

[0515] When the light-emitting devices 1 to 3 were made to emit light at a luminance of about 1000 cd / m 2 Table 2 shows the main initial characteristics (Note that the initial characteristics of other light-emitting devices are also described in Table 2, and their configurations will be described later).

[0516] [Table 2]

[0517] The light-emitting devices 1 to 3 were found to exhibit good characteristics. For example, in any of the light-emitting devices, good chromaticity and a high external quantum efficiency of 8.4% or more were confirmed. Also, it was found that the change in the external quantum efficiency with respect to the addition amount of the light-emitting material EM was small compared to Comparative Light-Emitting Devices 1 to 3. For example, when the external quantum efficiency of Comparative Light-Emitting Device 1 near a luminance of 1000 cd / m 2 was taken as 1, the external quantum efficiency of Comparative Light-Emitting Device 3 decreased to 0.74. On the other hand, in Light-Emitting Devices 1 to 3, when the external quantum efficiency of Light-Emitting Device 1 was taken as 1, the decrease in the external quantum efficiency of Light-Emitting Device 3 could be suppressed to 0.84 (see Fig. 31). As a result, characteristics that are less affected by fluctuations in production equipment could be imparted to the light-emitting device. Or, characteristics that are less affected by slight differences in the addition concentration of the light-emitting material EM could be imparted to the light-emitting device. As a result, a novel light-emitting device excellent in convenience, usefulness, or reliability could be provided.

[0518] (Reference Example 1) Table 3 shows the configurations of Comparative Light-Emitting Devices 1 to 3.

[0519] In the fabricated Comparative Light-Emitting Devices 1 to 3 described in this example, layer 111 contains tBuBPA2Dfbf instead of tBuFrA2Dfbf-02.

[0520] [Table 3]

[0521] 《Fabrication Method of Comparative Light-Emitting Devices 1 to 3》 Comparative Light-Emitting Devices 1 to 3 were fabricated using a method having the following steps.

[0522] Note that the manufacturing methods of Comparative Light-Emitting Devices 1 to 3 differ from those of Light-Emitting Devices 1 to 3 in that, in the step of forming Layer 111, tBuBPA2Dfbf is co-evaporated instead of tBuFrA2Dfbf. Here, the different parts will be described in detail, and for the parts using the same method, the above description will be incorporated by reference.

[0523] [Step 5] In Step 5, Layer 111 was formed on Region 112B. Specifically, the materials were co-evaporated using the resistance heating method.

[0524] Note that Layer 111 contains cgDBCzPA and tBuBPA2Dfbf and has a thickness of 25 nm. Specifically, in Comparative Light-Emitting Device 1, Layer 111 contains tBuBPA2Dfbf at a weight ratio of cgDBCzPA:tBuBPA2Dfbf = 1:0.015, in Comparative Light-Emitting Device 2, Layer 111 contains tBuBPA2Dfbf at a weight ratio of cgDBCzPA:tBuBPA2Dfbf = 1:0.03, and in Comparative Light-Emitting Device 3, Layer 111 contains tBuBPA2Dfbf at a weight ratio of cgDBCzPA:tBuBPA2Dfbf = 1:0.05.

[0525] 《Operating Characteristics of Comparative Light-Emitting Devices 1 to 3》 The operating characteristics of Comparative Light-Emitting Devices 1 to 3 were measured. The measurements were carried out at room temperature.

[0526] The main initial characteristics of Comparative Light-Emitting Devices 1 to 3 are shown in Table 2.

[0527] <Calculation Method for HOMO Level and LUMO Level of Materials> Regarding the HOMO level and LUMO level of the materials, they were calculated based on cyclic voltammetry (CV) measurements. The calculation method is shown below.

[0528] As the measuring device, an electrochemical analyzer (manufactured by BAS Inc., model number: ALS model 600A or 600C) was used. The solution for CV measurement used dehydrated dimethylformamide (DMF) (manufactured by Aldrich Co., Ltd., 99.8%, catalog number: 22705-6) as the solvent, and tetra-n-butylammonium perchlorate (n-Bu 4 NClO 4 )(manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) was dissolved to a concentration of 100 mmol / L, and the measurement target was further dissolved to a concentration of 2 mmol / L for preparation.

[0529] Also, as the working electrode, a platinum electrode (manufactured by BAS Inc., PTE platinum electrode) was used, as the auxiliary electrode, a platinum electrode (manufactured by BAS Inc., Pt counter electrode for VC-3 (5 cm)) was used, and as the reference electrode, an Ag / Ag + electrode (manufactured by BAS Inc., RE7 non-aqueous solvent reference electrode) was used respectively. The measurement was carried out at room temperature (20 to 25 °C).

[0530] Also, the scan rate during CV measurement was unified to 0.1 V / sec, and the oxidation potential Ea [V] and reduction potential Ec [V] with respect to the reference electrode were measured. Ea was taken as the intermediate potential of the oxidation-reduction wave, and Ec was taken as the intermediate potential of the reduction-oxidation wave. Here, since it is known that the potential energy of the reference electrode used in this example with respect to the vacuum level is -4.94 [eV], the HOMO level [eV] = -4.94 - Ea and the LUMO level [eV] = -4.94 - Ec, and the HOMO level and LUMO level can be obtained respectively from these formulas.

Example

[0531] In this example, the structure, manufacturing method, and characteristics of the light-emitting device 4 according to one aspect of the present invention will be described with reference to FIGS. 24, 32 to 38.

[0532] FIG. 32 is a diagram for explaining the current density-luminance characteristics of the light-emitting device 4.

[0533] FIG. 33 is a diagram for explaining the luminance-current efficiency characteristics of the light-emitting device 4.

[0534] FIG. 34 is a diagram for explaining the voltage-luminance characteristics of the light-emitting device 4.

[0535] FIG. 35 is a diagram for explaining the voltage-current characteristics of the light-emitting device 4.

[0536] FIG. 36 is a diagram for explaining the luminance-external quantum efficiency characteristics of the light-emitting device 4. Note that assuming the light distribution characteristics of the light-emitting device are of the Lambertian type, the external quantum efficiency was calculated from the luminance and emission spectrum observed from the front.

[0537] FIG. 37 is a diagram for explaining the emission spectrum when the light-emitting device 4 emits light at a luminance of 1000 cd / m 2 ^2.

[0538] FIG. 38 is a diagram for explaining the time change of the normalized luminance when the light-emitting device 4 emits light at a constant current density of 50 mA / cm 2 ^2. Note that the time change of the normalized luminance when the comparative light-emitting device emits light at a constant current density of 50 mA / cm 2 ^2 is also shown.

[0539] <Light-emitting device 4> The fabricated light-emitting device 4 described in this example has the same configuration as the light-emitting device 150 (see FIG. 24).

[0540] The light-emitting device 150 has an electrode 101, an electrode 102, a unit 103, and a layer 104, and the electrode 102 has a region overlapping with the electrode 101. The light-emitting device 150 also has a layer 105.

[0541] The unit 103 has a region sandwiched between the electrode 101 and the electrode 102, and the unit 103 has a layer 111, a layer 112, and a layer 113.

[0542] Layer 112 includes a region sandwiched between electrode 101 and layer 111, and layer 113 includes a region sandwiched between layer 111 and electrode 102.

[0543] Layer 111 contains a light-emitting material EM. In the light-emitting device 4, PCA2Dfbf-02 was used as the light-emitting material EM.

[0544] 《Configuration of Light-Emitting Device 4》 The configuration of the light-emitting device 4 is shown in Table 4. The structural formulas of the materials used in the light-emitting device 4 and the comparative light-emitting device 4 described in this example are shown below.

[0545]

Table 4

[0546]

Chemical Formula

[0547] 《Fabrication Method of Light-Emitting Device 4》 The light-emitting device 4 described in this example was fabricated using a method having the following steps.

[0548] [First Step] In the first step, electrode 101 was formed. Specifically, it was formed by sputtering using indium tin oxide (ITSO) containing silicon or silicon oxide as the target.

[0549] Note that electrode 101 contains ITSO, has a thickness of 70 nm, and an area of 4 mm 2 (2 mm × 2 mm).

[0550] Next, the substrate on which electrode 101 was formed was washed with water, baked at 200 °C for 1 hour, and then subjected to UV ozone treatment for 370 seconds. Then, 10 -4The substrate was introduced into a vacuum evaporation apparatus whose interior was depressurized to the Pa level, and vacuum baking was performed at 170 °C for 30 minutes in the heating chamber of the vacuum evaporation apparatus. Thereafter, the substrate was allowed to cool for about 30 minutes.

[0551] [Second step] In the second step, layer 104 was formed on electrode 101. Specifically, the materials were co-evaporated using the resistance heating method.

[0552] Note that layer 104 contains BBABnf and OCHD-001 at a ratio of BBABnf:OCHD-001 = 1:0.1 (weight ratio) and has a thickness of 10 nm.

[0553] [Third step] In the third step, region 112A was formed on layer 104. Specifically, the material was evaporated using the resistance heating method.

[0554] Note that region 112A contains BBABnf and has a thickness of 20 nm.

[0555] [Fourth step] In the fourth step, region 112B was formed on region 112A. Specifically, the material was evaporated using the resistance heating method.

[0556] Note that region 112B contains 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbazole) (abbreviation: PCzN2) and has a thickness of 10 nm.

[0557] [Fifth step] In the fifth step, layer 111 was formed on region 112B. Specifically, the materials were co-evaporated using the resistance heating method.

[0558] Note that layer 111 contains αN-βNPAnth and PCA2Dfbf-02 at a ratio of αN-βNPAnth:PCA2Dfbf-02 = 1:0.015 (weight ratio) and has a thickness of 25 nm.

[0559] [Step 6] In Step 6, region 113A was formed on layer 111. Specifically, a material was vapor-deposited using a resistive heating method.

[0560] Note that region 113A contains 2mDBTBPDBq-II and has a thickness of 15 nm.

[0561] [Step 7] In Step 7, region 113B was formed on region 113A. Specifically, a material was vapor-deposited using a resistive heating method.

[0562] Note that region 113B contains NBPhen and has a thickness of 10 nm.

[0563] [Step 8] In Step 8, layer 105 was formed on region 113B. Specifically, a material was vapor-deposited using a resistive heating method.

[0564] Note that layer 105 contains LiF and has a thickness of 1 nm.

[0565] [Step 9] In Step 9, electrode 102 was formed on layer 105. Specifically, a material was vapor-deposited using a resistive heating method.

[0566] Note that electrode 102 contains Al and has a thickness of 150 nm.

[0567] 《Operating Characteristics of Light-Emitting Device 4》 When power was supplied, light-emitting device 4 emitted light EL1 (see Fig. 24). The operating characteristics of light-emitting device 4 were measured (see Figs. 32 to 38). The measurement was performed at room temperature.

[0568] The main initial characteristics of light-emitting device 4 when it was made to emit light at a luminance of about 1000 cd / m 2 are shown in Table 2.

[0569] The light-emitting device 4 was found to exhibit good characteristics. For example, good chromaticity and a high external quantum efficiency of 11.5% were confirmed. Also, an external quantum efficiency higher than 10.9% was confirmed as compared with the comparative light-emitting device 4. Further, it was confirmed that the light-emitting device 4 had a narrow half-value width emission spectrum as compared with the comparative light-emitting device 4 (see FIG. 37). As a result, a novel light-emitting device excellent in convenience, utility, or reliability could be provided.

[0570] (Reference Example 2) The configuration of the comparative light-emitting device 4 is shown in Table 5.

[0571] The fabricated comparative light-emitting device 4 described in this example includes 3,10PCA2Nbf(IV)-02 instead of PCA2Dfbf-02 in layer 111.

[0572] [Table 5]

[0573] 《Method for fabricating the comparative light-emitting device 4》 The comparative light-emitting device 4 was fabricated using a method having the following steps.

[0574] Note that the method for fabricating the comparative light-emitting device 4 is different from the method for fabricating the light-emitting device 4 in the step of forming layer 111. Specifically, the co-evaporation of 3,10PCA2Nbf(IV)-02 instead of PCA2Dfbf-02 so as to be 0.015 (weight ratio) with respect to αN-βNPAnth is different from the method for fabricating the light-emitting device 4. Here, the different parts will be described in detail, and for the parts using the same method, the above description will be incorporated by reference.

[0575] [Fifth step] In the fifth step, layer 111 was formed on region 112B. Specifically, the materials were co-evaporated using a resistance heating method.

[0576] Layer 111 contains αN-βNPAnth and 3,10PCA2Nbf(IV)-02 at a weight ratio of αN-βNPAnth:3,10PCA2Nbf(IV)-02 = 1:0.015 and has a thickness of 25 nm.

[0577] 《Operating Characteristics of Comparative Light-Emitting Device 4》 The operating characteristics of comparative light-emitting device 4 were measured. The measurement was performed at room temperature.

[0578] The main initial characteristics of comparative light-emitting device 4 are shown in Table 2.

Example

[0579] In this example, the structure, manufacturing method, and characteristics of light-emitting device 5 according to one aspect of the present invention will be described with reference to FIGS. 24, 39 to 44.

[0580] FIG. 39 is a diagram for explaining the current density-luminance characteristics of light-emitting device 5.

[0581] FIG. 40 is a diagram for explaining the luminance-current efficiency characteristics of light-emitting device 5.

[0582] FIG. 41 is a diagram for explaining the voltage-luminance characteristics of light-emitting device 5.

[0583] FIG. 42 is a diagram for explaining the voltage-current characteristics of light-emitting device 5.

[0584] FIG. 43 is a diagram for explaining the luminance-external quantum efficiency characteristics of light-emitting device 5. The external quantum efficiency was calculated from the luminance and emission spectrum observed from the front, assuming that the light distribution characteristics of the light-emitting device are of the Lambertian type.

[0585] FIG. 44 is a diagram for explaining the emission spectrum when light-emitting device 5 emits light at a luminance of 1000 cd / m 2 ^2.

[0586] <Light-Emitting Device 5> The fabricated light-emitting device 5 described in this embodiment has the same configuration as the light-emitting device 150 (see Fig. 24). Note that the light-emitting device 5 is different from the light-emitting device 4 in that FrA2Dfbf-02 is used as the light-emitting material EM instead of PCA2Dfbf-02. Here, the different parts will be described in detail, and for the same configurations, the above description will be incorporated by reference.

[0587] Layer 111 contains the light-emitting material EM. Note that in the light-emitting device 5, FrA2Dfbf-02 is used as the light-emitting material EM.

[0588] 《Configuration of Light-Emitting Device 5》 The configuration of the light-emitting device 5 is shown in Table 6.

[0589]

Table 6

[0590] 《Fabrication Method of Light-Emitting Device 5》 The light-emitting device 5 described in this embodiment was fabricated using a method having the following steps.

[0591] Note that the fabrication method of the light-emitting device 5 is different from that of the light-emitting device 4 in that the step of forming layer 111 is different. Specifically, it is different from the fabrication method of the light-emitting device 4 in that FrA2Dfbf-02 is co-evaporated instead of PCA2Dfbf-02 so as to be 0.015 (weight ratio) with respect to αN-βNPAnth. Here, the different parts will be described in detail, and for the parts using the same method, the above description will be incorporated by reference.

[0592] [Fifth Step] In the fifth step, layer 111 was formed on region 112B. Specifically, the materials were co-evaporated using the resistance heating method.

[0593] Layer 111 contains αN-βNPAnth and FrA2Dfbf-02 at a weight ratio of αN-βNPAnth:FrA2Dfbf-02 = 1:0.015 and has a thickness of 25 nm.

[0594] 《Operating Characteristics of Light-Emitting Device 5》 When power was supplied, the light-emitting device 5 emitted light EL1 (see Fig. 24). The operating characteristics of the light-emitting device 5 were measured (see Figs. 39 to 44). The measurements were made at room temperature.

[0595] Table 2 shows the main initial characteristics of the light-emitting device 5 when it was made to emit light at a luminance of about 1000 cd / m 2 .

[0596] The light-emitting device 5 was found to exhibit good characteristics. As a result, a novel light-emitting device excellent in convenience, utility, or reliability could be provided.

Example

[0597] (Synthesis Example 4) In this example, the physical properties and synthesis method of the organic compound according to one aspect of the present invention will be described with reference to Figs. 51 to 53. Specifically, the characteristics and synthesis method of N,N'-bis[9-(3,5-di-tert-butylphenyl)-9H-carbazol-2-yl]-N,N'-diphenyldibenzothieno[2,3-f;5,4-f']bisbenzofuran-3,10-diamine (abbreviation: mmtBuPCA2Dfbf-02), which is represented by the structural formula (111) in Embodiment 1, will be described. The structural formula of mmtBuPCA2Dfbf-02 is shown below.

[0598]

Chemical Formula

[0599] Fig. 51 is a diagram for explaining the absorption spectrum and emission spectrum of a toluene solution containing mmtBuPCA2Dfbf-02.

[0600] Figure 52 is a diagram for explaining the absorption spectrum and emission spectrum of solid thin-film mmtBuPCA2Dfbf-02.

[0601] Figures 53A and 53B are diagrams for explaining the 1 1H NMR spectrum of mmtBuPCA2Dfbf-02.

[0602] <Measuring apparatus and method for preparing measurement sample> The absorption spectrum of the toluene solution was measured using an ultraviolet-visible spectrophotometer (V550 type, manufactured by JASCO Corporation) and the absorption spectrum derived from toluene was subtracted.

[0603] The absorption spectrum of the solid thin-film sample was measured using a spectrophotometer (U4100, manufactured by Hitachi High-Technologies Corporation).

[0604] The emission spectrum was measured using a fluorometer (FP-8600, manufactured by JASCO Corporation), and the quantum yield was measured using an absolute PL quantum yield measuring apparatus (Quantaurus-QY, manufactured by Hamamatsu Photonics K.K.).

[0605] The solid thin-film sample was formed on a quartz substrate using a vacuum evaporation method.

[0606] <Physical properties> The absorption spectrum of the toluene solution containing mmtBuPCA2Dfbf-02 had peaks at 432 nm, 410 nm, 349 nm, 327 nm, and 280 nm (see Figure 51). Also, the emission spectrum had peaks at 448 nm and 475 nm. Note that light with a wavelength of 410 nm was used as the excitation light. Also, the quantum yield in the toluene solution was 92%.

[0607] The absorption spectrum of the solid thin film of mmtBuPCA2Dfbf-02 had peaks at 433 nm, 415 nm, 350 nm, 330 nm, and 295 nm (see Figure 52). Also, the emission spectrum had peaks at 463 nm, 490 nm, and 540 nm. Note that light with a wavelength of 400 nm was used as the excitation light.

[0608] As a result, it was found that mmtBuPCA2Dfbf-02 emits blue light. Also, it was found that it can be used as a host material for luminescent materials and fluorescent luminescent materials in the visible region. Further, it was found that the quantum yield is very high and it is suitable as a luminescent material.

[0609] <Synthesis method> The synthesis method of mmtBuPCA2Dfbf-02 will be described. The synthesis scheme (SC5) is shown below.

[0610]

Chemical formula

[0611] 0.84 g (2.0 mmol) of 3,10-dichlorodibenzo[b,b’]fluor[2,3-f;5,4-f’]bisbenzofuran, 2.3 g (5.1 mmol) of N-phenyl-9-(3,5-di-tert-butylphenyl)-9H-carbazole-2-amine, 72 mg (0.20 mmol) of di(1-adamantyl)-n-butylphosphine, and 1.2 g (12 mmol) of sodium tert-butoxide were placed in a 200 mL three-necked flask. 20 mL of xylene was added to this mixture. The mixture was degassed by stirring while reducing the pressure. 23 mg (40 μmol) of bis(dibenzylideneacetone)palladium(0) was added to this mixture, and it was stirred at 150 °C for 21 hours under a nitrogen stream.

[0612] After stirring, toluene was added to this mixture, and it was suction filtered through celite, alumina, and florisil, and the filtrate was concentrated to obtain a solid.

[0613] The obtained solid was purified by silica gel column chromatography (developing solvent: toluene:hexane = 1:3, then toluene:hexane = 3:7) to obtain a solid. Further, the obtained solid was reprecipitated with toluene / ethanol to obtain 1.9 g of a yellow solid in a yield of 77%.

[0614] Also, 1.2 g of the yellow solid was purified by sublimation using the train sublimation method. It was carried out by heating at 385 °C under the conditions of a pressure of 2.9×10 -2 Pa and an argon flow rate of 0 mL / min. After sublimation purification, 1.0 g of a yellow solid was obtained with a recovery rate of 86%.

[0615] 1 1H NMR The 1H NMR spectrum of the dichloromethane solution of the obtained yellow solid is shown in FIGS. 53A and 53B. Also, the numerical data are shown below. From this, it was found that mmtBuPCA2Dfbf-02 was obtained in this synthesis example. 1 1H NMR(CD 1 1H NMR(CD 2 2 2 l2, 500 MHz): δ = 1.20(s, 36H), 7.07(t, J1 = 7.5 Hz, 2H), 7.12 - 7.43(m, 28H), 7.85(d, J1 = 8.5 Hz, 2H), 7.99(s, 2H), 8.04(s, 2H), 8.06(d, J1 = 8.0 Hz, 2H), 8.09(d, J1 = 7.5 Hz, 2H).

Example

[0616] In this example, the light-emitting device 6 according to one aspect of the present invention will be described with reference to FIGS. 54 to 60.

[0617] FIG. 54 is a diagram for explaining the current density-luminance characteristics of the light-emitting device 6.

[0618] FIG. 55 is a diagram for explaining the luminance-current efficiency characteristics of the light-emitting device 6.

[0619] ​FIG. 56 is a diagram for explaining the voltage-luminance characteristics of the light-emitting device 6.

[0620] FIG. 57 is a diagram for explaining the voltage-current characteristics of the light-emitting device 6.

[0621] FIG. 58 is a diagram for explaining the luminance-external quantum efficiency characteristics of the light-emitting device 6. Note that assuming the light distribution characteristics of the light-emitting device are of the Lambertian type, the external quantum efficiency was calculated from the luminance observed from the front and the emission spectrum.

[0622] FIG. 59 is a diagram for explaining the emission spectrum when the light-emitting device 6 emits light at a luminance of 1000 cd / m 2 of.

[0623] FIG. 60 is a diagram for explaining the time change of the normalized luminance when the light-emitting device 6 emits light at a constant current density of 50 mA / cm 2 .

[0624] <Light-emitting device 6> The fabricated light-emitting device 6 described in this example has the same configuration as the light-emitting device 150 (see FIG. 24). The light-emitting device 150 has an electrode 101, an electrode 102, a unit 103, and a layer 104, and the electrode 102 has a region overlapping the electrode 101. Further, the light-emitting device 150 includes a layer 105.

[0625] The unit 103 has a region sandwiched between the electrode 101 and the electrode 102, and the unit 103 includes a layer 111, a layer 112, and a layer 113.

[0626] The layer 112 has a region sandwiched between the electrode 101 and the layer 111, and the layer 113 has a region sandwiched between the layer 111 and the electrode 102.

[0627] The layer 111 contains a light-emitting material EM. In the light-emitting device 6, mmtBuPCA2Dfbf-02 was used as the light-emitting material EM.

[0628] Layer 104 includes a material AM having acceptor properties and a material HT1. The material HT1 has a first HOMO level HOMO1, and the first HOMO level HOMO1 is not less than -5.7 eV and not more than -5.4 eV. In the light-emitting device 6, BBABnf was used for the material HT1. Also, according to cyclic voltammetry (CV) measurement, the HOMO level of BBABnf was -5.56 eV.

[0629] Layer 113 includes a material OMC, and the material OMC is an organometallic complex of an alkali metal or an organometallic complex of an alkaline earth metal. In the light-emitting device 6, Liq was used for the material OMC.

[0630] Layer 112 includes a region 112A and a region 112B. The region 112B includes a region sandwiched between the layer 111 and the region 112A, and the region 112B includes a material HT2. The material HT2 has a second HOMO level HOMO2, and the second HOMO level HOMO2 is in the range of not less than -0.2 eV and not more than 0 eV with respect to the first HOMO level HOMO1. In the light-emitting device 6, PCzN2 was used for the material HT2. Also, according to cyclic voltammetry (CV) measurement, the HOMO level of PCzN2 was -5.71 eV.

[0631] 《Configuration of Light-Emitting Device 6》 The configuration of the light-emitting device 6 is shown in Table 7. Also, the structural formulas of the materials used in the light-emitting device described in this example are shown below.

[0632]

Table 7

[0633]

Chemical Formula

[0634] 《Fabrication Method of Light-Emitting Device 6》 The light-emitting device 6 described in this example was fabricated using a method having the following steps.

[0635] [First step] In the first step, electrode 101 was formed. Specifically, it was formed by a sputtering method using indium tin oxide (abbreviation: ITSO) containing silicon or silicon oxide as a target.

[0636] Note that electrode 101 contains ITSO, has a thickness of 70 nm, and an area of 4 mm 2 (2 mm × 2 mm).

[0637] Next, the substrate on which electrode 101 was formed was washed with water, baked at 200 °C for 1 hour, and then subjected to UV ozone treatment for 370 seconds. After that, the substrate was introduced into a vacuum evaporation apparatus whose internal pressure was reduced to about 10 -4 Pa, and vacuum baking was performed at 170 °C for 30 minutes in the heating chamber of the vacuum evaporation apparatus. Then, the substrate was allowed to cool for about 30 minutes.

[0638] [Second step] In the second step, layer 104 was formed on electrode 101. Specifically, the materials were co-evaporated using a resistance heating method.

[0639] Note that layer 104 contains BBABnf and an electron acceptor material (abbreviation: OCHD-001) at a weight ratio of BBABnf:OCHD-001 = 1:0.1, and has a thickness of 10 nm. Note that OCHD-001 has acceptor properties.

[0640] [Third step] In the third step, region 112A was formed on layer 104. Specifically, the materials were evaporated using a resistance heating method.

[0641] Note that region 112A contains BBABnf and has a thickness of 20 nm.

[0642] [Fourth step] In the fourth step, region 112B was formed on region 112A. Specifically, the materials were evaporated using a resistance heating method.

[0643] Note that region 112B contains 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbazole) (abbreviation: PCzN2) and has a thickness of 10 nm.

[0644] [Fifth step] In the fifth step, layer 111 was formed on region 112B. Specifically, the materials were co-evaporated using the resistive heating method.

[0645] Note that layer 111 contains αN-βNPAnth and mmtBuPCA2Dfbf-02 at αN-βNPAnth:mmtBuPCA2Dfbf-02 = 1:0.015 (weight ratio) and has a thickness of 25 nm.

[0646] [Sixth step] In the sixth step, region 113A was formed on layer 111. Specifically, the materials were evaporated using the resistive heating method.

[0647] Note that region 113A contains 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)-1,1'-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn) and has a thickness of 10 nm.

[0648] [Seventh step] In the seventh step, region 113B was formed on region 113A. Specifically, the materials were co-evaporated using the resistive heating method.

[0649] Note that region 113B contains 2-[3-(2,6-dimethylpyridin-3-yl)-5-(9-phenanthryl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mPn-mDMePyPTzn) and Liq at mPn-mDMePyPTzn:Liq = 1:1 (weight ratio) and has a thickness of 15 nm.

[0650] [Eighth step] In the eighth step, layer 105 was formed on region 113B. Specifically, the material was vapor-deposited using a resistance heating method.

[0651] Note that layer 105 contains Liq and has a thickness of 1 nm.

[0652] [Ninth step] In the ninth step, electrode 102 was formed on layer 105. Specifically, the material was vapor-deposited using a resistance heating method.

[0653] Note that electrode 102 contains Al and has a thickness of 150 nm.

[0654] [Operating characteristics of light-emitting device 6] When power was supplied, light-emitting device 6 emitted light EL1 (see Fig. 24). The operating characteristics of light-emitting device 6 were measured at room temperature (see Figs. 54 to 60). Note that a spectro-radiometer (manufactured by Topcon Corporation, SR-UL1R) was used for measuring luminance, CIE chromaticity, and emission spectrum.

[0655] Table 2 shows the main initial characteristics when the fabricated light-emitting device was made to emit light at a luminance of about 1000 cd / m 2 2.

[0656] It was found that light-emitting device 6 exhibited good characteristics. For example, light-emitting device 6 showed a high efficiency with an external quantum efficiency exceeding 14% in the blue chromaticity. Also, in the constant current drive test at 50 mA / cm 2 2, the 10% degradation time was approximately 130 hours, indicating a long lifespan. As a result, a novel light-emitting device excellent in convenience, usefulness, or reliability could be provided. [Explanation of reference numerals]

[0657] 101: Electrode, 102: Electrode, 103: Unit, 103PD: Unit, 104: Layer, 105: Layer, 106: Intermediate layer, 106A: Layer, 106B: Layer, 111: Layer, 112: Layer, 112A: Region, 112B: Region, 113: Layer, 113A: Region, 113B: Region, 150: Light-emitting device, 150PD: Photoelectric conversion device, 400: Substrate, 401: Electrode, 403: EL layer, 404: Electrode, 405: Sealing material, 406: Sealing material, 407: Sealing substrate, 412: Pad, 420: IC chip, 601: Source line drive circuit, 602: Pixel portion, 603: Gate line drive circuit, 604: Sealing substrate, 605: Sealing material, 607: Space, 608: Wiring, 610: Element substrate, 611: Switching FET, 612: Current control FET, 613: Electrode, 614: Insulator, 616: EL layer, 617: Electrode, 618: Light-emitting device, 623: FET, 700: Light-emitting panel, 951: Substrate, 952: Electrode, 953: Insulating layer, 954: Partition layer, 955: EL layer, 956: Electrode, 1001: Substrate, 1002: Underlying insulating film, 1003: Gate insulating film, 1006: Gate electrode, 1007: Gate electrode, 1008: Gate electrode, 1020: Interlayer insulating film, 1021: Interlayer insulating film, 1022: Electrode, 1024B: Electrode, 1024G: Electrode, 1024R: Electrode, 1024W: Electrode, 1025: Partition, 1028: EL layer, 1029: Electrode, 1031: Sealing substrate, 1032: Sealing material, 1033: Substrate material, 1034B: Coloring layer, 1034G: Coloring layer, 1034R: Coloring layer, 1035: Black matrix, 1036: Overcoat layer, 1037: Interlayer insulating film, 1040: Pixel portion, 1041: Drive circuit portion, 1042: Peripheral portion, 2001: Housing, 2002: Light source, 2100: Robot, 2101: Illuminance sensor, 2102: Microphone, 2103: Upper camera, 2104: Speaker, 2105: Display, 2106: Lower camera, 2107: Obstacle sensor, 2108: Moving mechanism, 2110: Arithmetic unit, 3001: Lighting device, 5000: Housing, 5001: Display portion, 5002: Display portion, 5003: Speaker, 5004: LED lamp, 5005: Operation key, 5006: Connection terminal, 5007: Sensor, 5008: Microphone, 5012: Support portion, 5013: Earphone, 5100: Cleaning robot, 5101: Display, 5102: Camera, 5103: Brush,5104: Operation Button, 5120: Garbage, 5140: Portable Electronic Device, 5200: Display Area, 5201: Display Area, 5202: Display Area, 5203: Display Area, 7101: Housing, 7103: Display Unit, 7105: Stand, 7107: Display Unit, 7109: Operation Key, 7110: Remote Control Operation Unit, 7201: Main Body, 7202: Housing, 7203: Display Unit, 7204: Keyboard, 7205: External Connection Port, 7206: Pointing Device, 7210: Display Unit, 7401: Housing, 7402: Display Unit, 7403: Operation Button, 7404: External Connection Port, 7405: Speaker, 7406: Microphone, 9310: Portable Information Terminal, 9311: Display Panel, 9313: Hinge, 9315: Housing

Claims

1. An organic compound represented by general formula (G1): 【Chemistry 1】 (In the above general formula (G1), X １ ~X ３ each independently represents oxygen or sulfur; R １１ ~R ２２ Among these, 1 or 2 represents an amino group or an aryl group having an amino group represented by the above general formula (R0), R excluding 1 or 2 above １１ ~R ２２ each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alicyclic hydrocarbon group having 3 to 6 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 13 carbon atoms, R １１ ~R ２２ When 2 is an amino group or an aryl group having an amino group represented by the general formula (R0), R １１ ~R ２２ Two of the may be the same or different, In the above general formula (R0), α １ and α ２ each independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 carbon atoms, A represents a substituted or unsubstituted heteroaryl group; Ar １ represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 25 carbon atoms, m and n each independently represent an integer of 0 or 1.

2. In claim 1, R １２ and R １６ each independently represents an amino group or an aryl group having an amino group represented by general formula (R0).

3. In claim 1 or claim 2, A comprises a five-membered ring; The five-membered ring comprises a heteroatom.

4. In any one of claims 1 to 3, A represents a heteroaryl group having a carbazole skeleton, a dibenzofuran skeleton, or a dibenzothiophene skeleton; Ar １ represents a substituent having a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a carbazole skeleton, a dibenzofuran skeleton, or a dibenzothiophene skeleton.

5. In any one of claims 1 to 4, The amino group or aryl group having an amino group represented by the general formula (R0) is represented by the following general formula (R1): 【Chemistry 2】 (In the above general formula (R1), R ３１ ~R ４２ each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, an alicyclic hydrocarbon group having 3 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 13 carbon atoms.

6. In any one of claims 1 to 5, The amino group or aryl group having an amino group represented by the general formula (R0) is represented by the following general formula (R2): 【Chemistry 3】 (In the above general formula (R2), R ５１ ~R ６７ each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, an alicyclic hydrocarbon group having 3 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 13 carbon atoms.

7. A first electrode; A second electrode; and A unit, the second electrode has an area overlapping with the first electrode; the unit includes a region sandwiched between the first electrode and the second electrode; A light-emitting device, wherein the unit comprises an organic compound according to claim 1 .

8. A light emitting device according to claim 7; A light emitting device having a transistor or a substrate.

9. A light emitting device according to claim 7; A display device having a transistor or a substrate.

10. A light emitting device according to claim 8; A lighting device having a housing.

11. A display device according to claim 9 ; An electronic device having a sensor, an operation button, a speaker, or a microphone.

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