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

Abstract

To provide a novel light-emitting device that is highly convenient, useful, or reliable.SOLUTION: In an organic compound, a substituted or unsubstituted naphtho[2,3-c]carbazolyl group or a substituted or unsubstituted benzo[c]naphtho[2,3-g]carbazolyl group is bonded to a substituted or unsubstituted 9H-carbazolyl group or a substituted or unsubstituted anthryl group through a substituted or unsubstituted arylene group. The arylene group has 6 to 13, inclusive, carbon atoms.SELECTED DRAWING: None

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 apparatus, or a semiconductor device.

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

[0003] Display devices and light-emitting devices using organic EL elements have already been put into practical use in some areas, and their applications are expanding. Naturally, high quality is required for organic EL displays, which are said to be the next generation of displays.

[0004] While various materials have been developed for organic EL displays, not many possess properties sufficient for practical use. Furthermore, considering the diversity of combinations and compatibility, having more options is undoubtedly advantageous.

[0005] For example, it is known that when a dibenzo[c,g]carbazole compound, in which an aryl group having 14 to 30 carbon atoms and containing at least anthracene is bonded to the nitrogen of a dibenzo[c,g]carbazole derivative, is used in an organic EL device, a light-emitting element with very good characteristics can be easily obtained (Patent Document 1). [Prior art documents] [Patent Documents]

[0006] [Patent Document 1] Japanese Patent Publication No. 2013-48221 [Overview of the Initiative] [Problems that the invention aims to solve]

[0007] One aspect of the present invention aims to provide a novel organic compound that is excellent in convenience, usefulness, or reliability. Alternatively, it aims to provide a novel light-emitting device that is excellent in convenience, usefulness, or reliability. Alternatively, it aims to provide a novel photoelectric conversion device that is excellent in convenience, usefulness, or reliability. Alternatively, it aims to provide a novel light-emitting device that is excellent in convenience, usefulness, or reliability. Alternatively, it aims to provide a novel electronic device that is excellent in convenience, usefulness, or reliability. Alternatively, it aims to provide a novel display device that is excellent in convenience, usefulness, or reliability. Alternatively, it aims to provide a novel lighting device that is excellent in convenience, usefulness, or reliability. Alternatively, it aims to provide a novel organic compound, a novel light-emitting device, a novel light-emitting device, a novel electronic device, a novel display device, a novel lighting device, or a novel semiconductor device.

[0008] Furthermore, the description of these problems does not preclude the existence of other problems. Moreover, one aspect of the present invention does not need to solve all of these problems. Other problems will naturally become apparent from the description in the specification, drawings, and claims, and it is possible to extract other problems from the description in the specification, drawings, and claims. [Means for solving the problem]

[0009] (1) One aspect of the present invention is an organic compound represented by the following general formula (G1).

[0010] [ka]

[0011] However, in the above general formula (G1), E represents a substituted or unsubstituted naphtho[2,3-c]carbazolyl group or a substituted or unsubstituted benzo[c]naphtho[2,3-g]carbazolyl group, Ar represents a substituted or unsubstituted arylene group, the arylene group having 6 to 13 carbon atoms, and A represents a substituted or unsubstituted 9H-carbazolyl group or a substituted or unsubstituted anthryl group.

[0012] (2) Another aspect of the present invention is an organic compound represented by the following general formula (G2).

[0013] [ka]

[0014] However, in the above general formula (G2), substituent R 1 to substituent R 13 One of these is represented by the general formula (G3) above.

[0015] In the above general formula (G3), Ar represents a substituted or unsubstituted arylene group, and the arylene group has 6 to 13 carbon atoms. A represents a substituted or unsubstituted 9H-carbazolyl group or a substituted or unsubstituted anthyl group. Substituent R 1 to substituent R 13 The other elements are, independently, hydrogen, alkyl groups, cyclic alkyl groups, or substituted or unsubstituted aryl groups.

[0016] Alkyl groups have 1 to 6 carbon atoms, cyclic alkyl groups have 3 to 7 carbon atoms, and substituted or unsubstituted aryl groups have 6 to 13 carbon atoms.

[0017] (3) In another aspect of the present invention, in the above general formula (G2), the substituent R 1 , substituent R 3 , substituent R 4 or substituent R 10 One of these is an organic compound represented by the general formula (G3).

[0018] (4) In one aspect, the present invention provides an organic compound represented by the following general formula (G4).

[0019]

Chemical Formula

[0020] Provided that in the above general formula (G4), any one of substituent R 21 to substituent R 35 is represented by the above general formula (G3).

[0021] In the above general formula (G3), Ar represents a substituted or unsubstituted arylene group, and the arylene group has 6 to 13 carbon atoms. A represents a substituted or unsubstituted 9H-carbazolyl group or a substituted or unsubstituted anthryl group.

[0022] Other than substituent R 21 to substituent R 35 , each of the remaining groups is independently hydrogen, an alkyl group, a cyclic alkyl group, or a substituted or unsubstituted aryl group.

[0023] The alkyl group has 1 to 6 carbon atoms, the cyclic alkyl group has 3 to 7 carbon atoms, and the substituted or unsubstituted aryl group has 6 to 13 carbon atoms.

[0024] (5) In one aspect, the present invention provides the organic compound, wherein in the above general formula (G4), any one of substituent R 21 , substituent R 23 , substituent R 24 or substituent R 32 is represented by general formula (G3).

[0025] (6) In one aspect, the present invention provides the above organic compound, wherein in the above general formula (G3), Ar is a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenyldiyl group.

[0026] (7) Another aspect of the present invention is the above-mentioned organic compound, wherein in the above general formula (G3), A is a substituted or unsubstituted carbazo-9-yl group or a substituted or unsubstituted 9-anthryl group.

[0027] (8) Another aspect of the present invention is a light-emitting device having a first electrode, a second electrode, a first layer, and a second layer.

[0028] The second electrode has a region that overlaps with the first electrode, and the first layer has a region sandwiched between the first electrode and the second electrode.

[0029] The first layer comprises a luminescent material and a charge transport material CTM. The second layer comprises a region sandwiched between the first layer and the second electrode, and the second layer comprises the charge transport material CTM.

[0030] The charge transport material CTM is the organic compound described above.

[0031] (9) Another aspect of the present invention is a light-emitting device having the above-mentioned light-emitting device and a transistor or substrate.

[0032] (10) Another aspect of the present invention is a display device having the above-mentioned light-emitting device and a transistor or substrate.

[0033] (11) Another aspect of the present invention is a lighting device having a light-emitting device and a housing.

[0034] (12) Another aspect of the present invention is an electronic device having a display device, a sensor, an operation button, a speaker or a microphone.

[0035] In the drawings attached to this specification, the components are classified by function and shown as independent blocks in block diagrams. However, in reality, it is difficult to completely separate the components by function, and one component may be involved in multiple functions.

[0036] In this specification, the term "light-emitting device" includes image display devices using light-emitting elements. Furthermore, modules in which a connector, such as an anisotropic conductive film or TCP (Tape Carrier Package), is attached to a light-emitting element, modules in which a printed circuit board is provided at the end of the TCP, or modules in which an IC (integrated circuit) is directly mounted to a light-emitting element using the COG (Chip On Glass) method may also be included as light-emitting devices. Additionally, lighting fixtures and the like may have light-emitting devices. [Effects of the Invention]

[0037] According to one aspect of the present invention, it is possible to provide a novel organic compound that is excellent in convenience, usefulness, or reliability. Alternatively, it is possible to provide a novel light-emitting device that is excellent in convenience, usefulness, or reliability. Alternatively, one of the objectives is to provide a novel photoelectric conversion device that is excellent in convenience, usefulness, or reliability. Alternatively, it is possible to provide a novel light-emitting device that is excellent in convenience, usefulness, or reliability. Alternatively, it is possible to provide a novel electronic device that is excellent in convenience, usefulness, or reliability. Alternatively, it is possible to provide a novel display device that is excellent in convenience, usefulness, or reliability. Alternatively, it is possible to provide a novel lighting device that is excellent in convenience, usefulness, or reliability. Alternatively, 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.

[0038] Furthermore, the description of these effects does not preclude the existence of other effects. Moreover, one aspect of the present invention does not necessarily have to possess all of these effects. Other effects will naturally become apparent from the description in the specification, drawings, and claims, and it is possible to extract other effects from the description in the specification, drawings, and claims. [Brief explanation of the drawing]

[0039] [Figure 1] Figures 1(A) and 1(B) illustrate the configuration of a light-emitting device according to an embodiment. [Figure 2] Figures 2(A) and 2(B) illustrate the configuration of a light-emitting device according to an embodiment. [Figure 3] Figure 3 is a diagram illustrating the configuration of a functional panel according to an embodiment. [Figure 4] Figures 4(A) to 4(C) illustrate the configuration of a functional panel according to an embodiment. [Figure 5] Figures 5(A) and (B) are conceptual diagrams of an active matrix type light-emitting device. [Figure 6] Figures 6(A) and (B) are conceptual diagrams of an active matrix type light-emitting device. [Figure 7] Figure 7 is a conceptual diagram of an active matrix type light-emitting device. [Figure 8] Figures 8(A) and (B) are conceptual diagrams of a passive matrix type light-emitting device. [Figure 9] Figures 9(A) and (B) are diagrams representing lighting devices. [Figure 10] Figures 10(A) through (D) are diagrams representing electronic devices. [Figure 11] Figures 11(A) through (C) are diagrams representing electronic devices. [Figure 12] Figure 12 is a diagram representing a lighting device. [Figure 13] Figure 13 is a diagram representing a lighting device. [Figure 14] Figure 14 is a diagram representing an in-vehicle display device and lighting system. [Figure 15] Figures 15(A) through (C) are diagrams representing electronic devices. [Figure 16] Figure 16 shows the absorption and emission spectra of cNCzPA in a toluene solution. [Figure 17] Figure 17 shows the absorption and emission spectra of cNCzPA in a thin film state. [Figure 18] Figures 18(A) and (B) show the 1H NMR spectra of cNCzPA. [Figure 19]Figure 19 shows the absorption and emission spectra of cgBNCzPA in a toluene solution. [Figure 20] Figure 20 shows the absorption and emission spectra of cgBNCzPA in a thin film state. [Figure 21] Figures 21(A) and (B) show the 1H NMR spectra of cgBNCzPA. [Figure 22] Figure 22 shows the absorption and emission spectra of 9CzPPcNC in a toluene solution. [Figure 23] Figure 23 shows the absorption and emission spectra of 9CzPPcNC in a thin film state. [Figure 24] Figures 24(A) and (B) show the 1H NMR spectra of 9CzPPcNC. [Figure 25] Figure 25 shows the refractive index-wavelength characteristics and attenuation coefficient-wavelength characteristics of the organic compounds according to the examples. [Figure 26] Figure 26 is a diagram illustrating the configuration of a light-emitting device according to an embodiment. [Figure 27] Figure 27 illustrates the current density-luminance characteristics of the light-emitting device according to the embodiment. [Figure 28] Figure 28 illustrates the brightness-current efficiency characteristics of the light-emitting device according to the embodiment. [Figure 29] Figure 29 illustrates the voltage-luminance characteristics of the light-emitting device according to the embodiment. [Figure 30] Figure 30 illustrates the voltage-current characteristics of a light-emitting device according to an embodiment. [Figure 31] Figure 31 illustrates the luminance-external quantum efficiency characteristics of a light-emitting device according to an embodiment. [Figure 32] Figure 32 illustrates the emission spectrum of a light-emitting device according to an embodiment. [Figure 33] Figure 33 illustrates the current density-luminance characteristics of a light-emitting device according to an embodiment. [Figure 34]Figure 34 illustrates the brightness-current efficiency characteristics of the light-emitting device according to the embodiment. [Figure 35] Figure 35 illustrates the voltage-luminance characteristics of a light-emitting device according to an embodiment. [Figure 36] Figure 36 illustrates the voltage-current characteristics of a light-emitting device according to an embodiment. [Figure 37] Figure 37 illustrates the luminance-external quantum efficiency characteristics of the light-emitting device according to the embodiment. [Figure 38] Figure 38 illustrates the emission spectrum of a light-emitting device according to an embodiment. [Modes for carrying out the invention]

[0040] An organic compound according to one aspect of the present invention is bonded to a substituted or unsubstituted naphtho[2,3-c]carbazolyl group or a substituted or unsubstituted benzo[c]naphtho[2,3-g]carbazolyl group via a substituted or unsubstituted 9H-carbazolyl group or a substituted or unsubstituted anthyl group, with the arylene group having 6 to 13 carbon atoms.

[0041] This makes it possible to provide organic compounds with excellent carrier transport properties, or organic compounds that can be suitably used in light-emitting devices, or light-emitting devices with good properties. As a result, it is possible to provide novel organic compounds that are excellent in convenience, usefulness, or reliability.

[0042] Embodiments will be described in detail with reference to the drawings. However, it will be readily apparent to those skilled in the art that the present invention is not limited to the following description, and that its form and details can be modified in various ways without departing from the spirit and scope of the present invention. Accordingly, the present invention is not to be interpreted as being limited to the contents of the embodiments shown below. In the configuration of the invention described below, the same reference numerals are used in common across different drawings for the same parts or parts having similar functions, and repeated descriptions are omitted.

[0043] (Embodiment 1) This embodiment describes an organic compound according to one aspect of the present invention.

[0044] <Example 1 of an organic compound> The organic compound described in this embodiment is an organic compound represented by the following general formula (G1).

[0045] [ka]

[0046] [Example of E] In the above general formula (G1), E represents a substituted or unsubstituted naphtho[2,3-c]carbazolyl group or a substituted or unsubstituted benzo[c]naphtho[2,3-g]carbazolyl group. Substituents can include aryl groups having 6 to 13 carbon atoms, alkyl groups having 1 to 6 carbon atoms, or cycloalkyl groups having 6 to 10 carbon atoms. For example, phenyl, biphenyl, naphthyl, or fluorenyl groups can be used as substituents. The aryl group may also have 2 or fewer alkyl groups having 1 to 6 carbon atoms or cycloalkyl groups having 6 to 10 carbon atoms. Furthermore, for example, methyl, isopropyl, or tert-butyl groups can be used as substituents. Additionally, cyclohexyl or adamantyl groups can be used as substituents.

[0047] [Example of Ar] In the above general formula (G1), Ar represents a substituted or unsubstituted arylene group, and the arylene group has 6 to 13 carbon atoms. The substituents on the arylene group may be bonded to each other to form a ring. The substituents can be aryl groups with 6 to 13 carbon atoms, alkyl groups with 1 to 6 carbon atoms, or cycloalkyl groups with 6 to 10 carbon atoms. For example, phenyl, biphenyl, naphthyl, or fluorenyl groups can be used as substituents. The aryl group may have 2 or fewer alkyl groups with 1 to 6 carbon atoms or cycloalkyl groups with 6 to 10 carbon atoms. For example, methyl, isopropyl, and tert-butyl groups can be used as substituents. Cyclohexyl and adamantyl groups can also be used as substituents.

[0048] For example, phenylene groups, biphenyldiyl groups, naphthalene-diyl groups, fluorene-diyl groups, etc., can be used, and these groups may have substituents. In addition, arylene groups represented by the following structural formulas (Ar-1) to (Ar-17) can be used for Ar.

[0049] [ka]

[0050] [Example] In the above general formula (G1), A represents a substituted or unsubstituted 9H-carbazolyl group or a substituted or unsubstituted anthyl group. Substituents can include aryl groups having 6 to 13 carbon atoms, alkyl groups having 1 to 6 carbon atoms, or cycloalkyl groups having 6 to 10 carbon atoms. For example, phenyl, biphenyl, naphthyl, or fluorenyl groups can be used as substituents. The aryl group may also have 2 or fewer alkyl groups having 1 to 6 carbon atoms or cycloalkyl groups having 6 to 10 carbon atoms. Furthermore, for example, methyl, isopropyl, or tert-butyl groups can be used as substituents. Additionally, cyclohexyl or adamantyl groups can be used as substituents.

[0051] Specific examples of substituted or unsubstituted anthryl groups are shown below.

[0052] [ka]

[0053] Furthermore, specific examples of substituted or unsubstituted 9H-carbazolyl groups are shown below.

[0054] [ka]

[0055] <Example of an organic compound 2> The organic compound described in this embodiment is an organic compound represented by the following general formula (G2).

[0056] [ka]

[0057] 《Substituent R 1 to substituent R 13 One example of the following: In the above general formula (G2), substituent R 1to substituent R 13 One of these is represented by the following general formula (G3).

[0058] [ka]

[0059] [Example of Ar] In the above general formula (G3), Ar represents a substituted or unsubstituted arylene group, and the arylene group has 6 to 13 carbon atoms. Furthermore, if the arylene group has substituents, the substituents may be bonded to each other to form a ring. Substituents can include aryl groups with 6 to 13 carbon atoms, alkyl groups with 1 to 6 carbon atoms, or cycloalkyl groups with 6 to 10 carbon atoms. For example, phenyl, biphenyl, naphthyl, or fluorenyl groups can be used as substituents. The aryl group may also have 2 or fewer alkyl groups or cycloalkyl groups with 6 to 10 carbon atoms. For example, methyl, isopropyl, and tert-butyl groups can be used as substituents. Cyclohexyl and adamantyl groups can also be used as substituents.

[0060] For example, the arylene group represented by the above structural formulas (Ar-1) to (Ar-17) can be used for Ar.

[0061] [Example] In the above general formula (G3), A represents a substituted or unsubstituted 9H-carbazolyl group or a substituted or unsubstituted anthyl group. Substituents can include aryl groups having 6 to 13 carbon atoms, alkyl groups having 1 to 6 carbon atoms, or cycloalkyl groups having 6 to 10 carbon atoms. For example, phenyl, biphenyl, naphthyl, or fluorenyl groups can be used as substituents. The aryl group may also have 2 or fewer alkyl groups having 1 to 6 carbon atoms or cycloalkyl groups having 6 to 10 carbon atoms. Furthermore, for example, methyl, isopropyl, or tert-butyl groups can be used as substituents. Additionally, cyclohexyl or adamantyl groups can be used as substituents.

[0062] 《Substituent R 1 to substituent R 13 Other examples》 Furthermore, in the above general formula (G2), substituent R 1 to substituent R 13 The other elements are, independently, hydrogen, alkyl groups, cyclic alkyl groups, or substituted or unsubstituted aryl groups.

[0063] If the substituent is an alkyl group, it has 1 to 6 carbon atoms; if the substituent is a cyclic alkyl group, it has 3 to 7 carbon atoms.

[0064] [ka]

[0065] Furthermore, if the substituent is an aryl group, the number of carbon atoms is between 6 and 13.

[0066] [ka]

[0067] <Specific examples of organic compounds> Specific examples of organic compounds having the above configuration are shown below.

[0068] [ka]

[0069] [ka]

[0070] [ka]

[0071] [ka]

[0072] [ka]

[0073] [ka]

[0074] <Example 3 of organic compounds> The organic compound described in this embodiment is an organic compound represented by the following general formula (G4).

[0075] [ka]

[0076] 《Substituent R 21 to substituent R 35 One example of the following: In the above general formula (G4), substituent R 21 to substituent R 35 One of these is represented by the following general formula (G3).

[0077] [ka]

[0078] [Example of Ar] In the above general formula (G3), Ar represents a substituted or unsubstituted arylene group, and the arylene group has 6 to 13 carbon atoms. Furthermore, if the arylene group has substituents, the substituents may be bonded to each other to form a ring. Substituents can include aryl groups with 6 to 13 carbon atoms, alkyl groups with 1 to 6 carbon atoms, or cycloalkyl groups with 6 to 10 carbon atoms. For example, phenyl, biphenyl, naphthyl, or fluorenyl groups can be used as substituents. The aryl group may also have 2 or fewer alkyl groups or cycloalkyl groups with 6 to 10 carbon atoms. For example, methyl, isopropyl, and tert-butyl groups can be used as substituents. Cyclohexyl and adamantyl groups can also be used as substituents.

[0079] For example, the arylene group represented by the above structural formulas (Ar-1) to (Ar-17) can be used for Ar.

[0080] [Example] In the above general formula (G3), A represents a substituted or unsubstituted 9H-carbazolyl group or a substituted or unsubstituted anthyl group. Substituents can include aryl groups having 6 to 13 carbon atoms, alkyl groups having 1 to 6 carbon atoms, or cycloalkyl groups having 6 to 10 carbon atoms. For example, phenyl, biphenyl, naphthyl, or fluorenyl groups can be used as substituents. The aryl group may also have 2 or fewer alkyl groups having 1 to 6 carbon atoms or cycloalkyl groups having 6 to 10 carbon atoms. Furthermore, for example, methyl, isopropyl, or tert-butyl groups can be used as substituents. Additionally, cyclohexyl or adamantyl groups can be used as substituents.

[0081] For example, a substituted or unsubstituted anthryl group represented by the above structural formulas (A-1) to (A-9) or a substituted or unsubstituted 9H-carbazolyl group represented by the above structural formulas (A-10) to (A-16) can be used for A.

[0082] 《Substituent R 21 to substituent R 35 Other examples》 Note that substituent R 21 to substituent R 35 Other substituents are, independently, hydrogen, alkyl groups, cyclic alkyl groups, or substituted or unsubstituted aryl groups. If the substituent is an alkyl group, it has 1 to 6 carbon atoms; if the substituent is a cyclic alkyl group, it has 3 to 7 carbon atoms; and if the substituent is an aryl group, it has 6 to 13 carbon atoms.

[0083] If the substituent is an alkyl group, it has 1 to 6 carbon atoms; if the substituent is a cyclic alkyl group, it has 3 to 7 carbon atoms. For example, substituents represented by the above structural formulas (R-1) to (R-17) can be used.

[0084] Furthermore, if the substituent is an aryl group, it has 6 to 13 carbon atoms. For example, substituents represented by the above structural formulas (R-18) to (R-32) can be used.

[0085] <Specific examples of organic compounds> Specific examples of organic compounds having the above configuration are shown below.

[0086] [ka]

[0087] [ka]

[0088] [ka]

[0089] [ka]

[0090] <Method 1 for synthesizing organic compounds> The organic compound represented by general formula (G2) can be synthesized by the following synthesis schemes (A-1) to (A-3).

[0091] [Step 1] As shown in the synthesis scheme (A-1) below, compound 3 is obtained by cross-coupling compound 1 and compound 2. Specifically, compound 3 can be obtained by coupling via the Suzuki-Miyaura reaction.

[0092] [ka]

[0093] An anthracene derivative organoboron compound or an anthracene derivative boronic acid can be used in compound 1. 50 and substituent R 51 They may be joined to each other to form a ring.

[0094] A halogenated nitrobenzene derivative or a triflate-substituted nitrobenzene derivative can be used in compound 2. 11 This represents a halogen or triflate group.

[0095] Substituent R 2 to substituent R 13 This is a hydrogen atom, an alkyl group, a cyclic alkyl group, or a substituted or unsubstituted aryl group. If it is an alkyl group, it has 1 to 6 carbon atoms; if it is a cyclic alkyl group, it has 3 to 7 carbon atoms; and if it is an aryl group, it has 6 to 13 carbon atoms.

[0096] Furthermore, substituent R 2 to substituent R 13 It may have substituents represented by the general formula (G3). Ar represents a substituted or unsubstituted arylene group, which has 6 to 13 carbon atoms. A represents a substituted or unsubstituted 9H-carbazolyl group or a substituted or unsubstituted anthryl group.

[0097] [ka]

[0098] In synthesis scheme (A-1), for example, palladium(II) acetate, tetrakis(triphenylphosphine)palladium(O), or bis(triphenylphosphine)palladium(II) dichloride can be used as the palladium catalyst.

[0099] Furthermore, for example, tri(ortho-tolyl)phosphine, triphenylphosphine, or tricyclohexylphosphine can be used as ligands for palladium catalysts.

[0100] Furthermore, organic bases such as sodium tert-butoxide or inorganic bases such as potassium carbonate or sodium carbonate can be used as the base.

[0101] Furthermore, mixed solvents such as toluene and water, xylene and water, benzene and water, and ethers such as ethylene glycol dimethyl ether and water can be used as reaction solvents.

[0102] Furthermore, mixed solvents of toluene, water, and alcohols such as ethanol, mixed solvents of xylene, water, and alcohols such as benzene, water, and alcohols such as benzene, can be used as reaction solvents. In particular, mixed solvents of toluene and water, mixed solvents of toluene, water, and ethanol, and mixed solvents of ethers such as ethylene glycol dimethyl ether and water are preferred.

[0103] Alternatively, compound 3 may be obtained by coupling an anthracene derivative halide or triflate-substituted product with an organoboron compound or boronic acid of a nitrobenzene derivative using the Suzuki-Miyaura reaction.

[0104] Alternatively, a cross-coupling reaction using organoaluminum, organozirconium, organozinc, or organotin compounds may be used instead of organoboron compounds or boronic acids.

[0105] [Step 2] As shown in the synthesis scheme (A-2) below, compound 3 is cyclized to obtain compound 4. Specifically, compound 3 is cyclized by the Cadogan reaction to obtain the naphtho[2,3-c]carbazole derivative (compound 4).

[0106] [ka]

[0107] In the synthesis scheme (A-2), for example, tri(ortho-tolyl)phosphine, triphenylphosphine, tricyclohexylphosphine, or tri(ethoxy)phosphine can be used.

[0108] Furthermore, solvents such as toluene, xylene, or orthodichlorobenzene can be used.

[0109] Alternatively, the naphtho[2,3-c]carbazole ring may be synthesized using the Graebe-UllMann method or the Fischer-Borsche method.

[0110] [Step 3] As shown in the synthesis scheme (A-3) below, compound 4 and compound 5 are cross-coupled to obtain the target product. Specifically, the target compound (G2) can be obtained by coupling them via the Ullmann reaction.

[0111] [ka]

[0112] A halogenated aromatic compound or a triflate-substituted aromatic compound can be used in compound 5. 12 This represents a halogen or triflate group.

[0113] In synthesis scheme (A-3), a copper compound or copper can be used in the Ullmann reaction. For example, copper(I) iodide or copper(II) acetate can be used as the copper compound.

[0114] Furthermore, inorganic bases such as potassium carbonate can be used as the base.

[0115] Furthermore, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU), toluene, xylene, benzene, etc., can be used as reaction solvents. In the Ullmann reaction, if the reaction temperature is 100°C or higher, the target product can be obtained in a short time and in high yield, so it is preferable to use xylene or DMPU, which have high boiling points. In particular, it is even more preferable if the reaction temperature is 150°C or higher, and DMPU is even more preferable.

[0116] Alternatively, the Hartwick-Buchwald reaction or other reactions can be used instead of the Ullmann reaction.

[0117] <Method for synthesizing organic compounds 2> The organic compound represented by general formula (G4) can be synthesized by the following synthesis schemes (B-1) to (B-3).

[0118] [Step 1] As shown in the synthesis scheme (B-1) below, compound 6 and compound 7 are cross-coupled to obtain compound 8. Specifically, compound 8 can be obtained by coupling via the Suzuki-Miyaura reaction.

[0119] [ka]

[0120] An anthracene derivative organoboron compound or an anthracene derivative boronic acid can be used in compound 6. 52 and substituent R 53 They may be joined to each other to form a ring.

[0121] A halogenated nitronaphthalene derivative or a triflate-substituted nitronaphthalene derivative can be used in compound 7. 21 This represents a halogen or triflate group.

[0122] Substituent R 22 to substituent R 35 This is a hydrogen atom, an alkyl group, a cyclic alkyl group, or a substituted or unsubstituted aryl group. If it is an alkyl group, it has 1 to 6 carbon atoms; if it is a cyclic alkyl group, it has 3 to 7 carbon atoms; and if it is an aryl group, it has 6 to 13 carbon atoms.

[0123] Furthermore, substituent R 22 to substituent R 35 It may have substituents represented by the general formula (G3). Ar represents a substituted or unsubstituted arylene group, which has 6 to 13 carbon atoms. A represents a substituted or unsubstituted 9H-carbazolyl group or a substituted or unsubstituted anthryl group.

[0124] [ka]

[0125] Furthermore, the method described in step 1 of organic compound synthesis method 1 can be applied to synthesis scheme (B-1).

[0126] Alternatively, compound 8 may be obtained by coupling a halogenated or triflate-substituted anthracene derivative with an organoboron compound or boronic acid of a nitronaphthalene derivative using the Suzuki-Miyaura reaction.

[0127] [Step 2] As shown in the synthesis scheme (B-2) below, compound 8 is cyclized to obtain compound 9. Specifically, compound 8 is cyclized by the Cadogan reaction to obtain the benzo[c]naphtho[2,3-g]carbazole derivative (compound 9).

[0128] [ka]

[0129] Furthermore, the method described in step 2 of organic compound synthesis method 1 can be applied to synthesis scheme (B-2).

[0130] [Step 3] As shown in the synthesis scheme (B-3) below, compound 9 and compound 10 are cross-coupled to obtain the target product. Specifically, the target compound (G4) can be obtained by coupling via the Ullmann reaction.

[0131] [ka]

[0132] A halogenated aromatic compound or a triflate-substituted aromatic compound can be used in compound 10. 22 This represents a halogen or triflate group.

[0133] Furthermore, the method described in step 3 of organic compound synthesis method 1 can be applied to synthesis scheme (B-3).

[0134] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0135] (Embodiment 2) In this embodiment, the configuration of a light-emitting device 150 according to one aspect of the present invention will be described with reference to Figure 1.

[0136] <Example configuration of light-emitting device 150> The light-emitting device 150 described in this embodiment includes an electrode 101, an electrode 102, and a unit 103. Electrode 102 has a region that overlaps with electrode 101, and unit 103 has a region sandwiched between electrode 101 and electrode 102.

[0137] <Example configuration of Unit 103> Unit 103 has a single-layer structure or a laminated structure. For example, unit 103 comprises layers 111, 112, and 113 (see Figure 1(A)).

[0138] Layer 111 includes a region sandwiched between layers 112 and 113, layer 112 includes a region sandwiched between electrode 101 and layer 111, and layer 113 includes a region sandwiched between electrode 102 and layer 111.

[0139] For example, a layer selected from functional layers such as an emissive layer, a hole transport layer, an electron transport layer, and a carrier block layer can be used in unit 103. Furthermore, a layer selected from functional layers such as a hole injection layer, an electron injection layer, an exciton block layer, and a charge generation layer can also be used in unit 103.

[0140] 《Example of Layer 111 Configuration 1》 For example, luminescent materials and host materials can be used in layer 111. Layer 111 can also be referred to as a light-emitting layer. It is preferable to position layer 111 in a region where holes and electrons recombine. This allows the energy generated by carrier recombination to be efficiently emitted as light. It is also preferable to position layer 111 away from metals used in electrodes, etc. This suppresses quenching caused by metals used in electrodes, etc.

[0141] A material possessing carrier transport properties, such as a charge transport material CTM, can be used as the host material. Specifically, the organic compound described in Embodiment 1 can be used as the charge transport material CTM. It is preferable to use a material as the host material that has a larger band gap than the luminescent material contained in layer 111, in other words, a material whose excitation energy from S0 to S1 is greater than that of the luminescent material contained in layer 111. This makes it possible to suppress energy transfer from excitons generated in layer 111 to the host material.

[0142] 《Example of Layer 111 Configuration 2》 For example, fluorescent materials can be used as luminescent materials. This allows the energy generated by carrier recombination to be released from the luminescent material as photo-EL1 (see Figure 1(A)).

[0143] [Fluorescent material] A fluorescent material can be used in layer 111. For example, the organic compound described in Embodiment 1 can also be used as a fluorescent material. In addition, the fluorescent materials exemplified below can be used in layer 111. However, this is not limited to these examples.

[0144] Specifically, 5,6-bis[4-(10-phenyl-9-antryl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl-9-antryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), N,N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl)phenyl]pyren-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-carbazole-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazole-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazole-9-yl)-4'-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-diphenyl-N-[4 -(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra(tert-butyl)perylene (abbreviation: TBP), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBAPA), N,N''-(2-tert-butylanthracene-9,10-diyldi-4,1-phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine] (abbreviation: DPABPA), N ,9-diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: 2PCAPPA), N-[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-carbazole-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-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: 2DPAB) PhA), 9,10-bis(1,1'-biphenyl-2-yl)-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracene-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracene-9-amine (abbreviation: DPhAPhA), coumarin 545T, N,N'-diphenylquinacridone (abbreviation: DPQd), rubren, 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]quinoridine-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluorantene-3,10-di Amine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinoridine-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]quinoridine-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]quinoridine-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-carbazole-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nbf(IV)-02), 3,10-bis[N-(dibenzofuran-3-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10FrA2Nbf(IV)-02), etc. can be used.

[0145] In particular, condensed aromatic diamine compounds, such as pyrenediamine compounds like 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6BnfAPrn-03, are preferred because they exhibit high hole-trapping properties and excellent luminescence efficiency or reliability.

[0146] 《Example of Layer 113 Configuration 1》 For example, electron-transporting materials, materials with an anthracene skeleton, and mixed materials can be used for layer 113. Layer 113 can also be called an electron transport layer. It is preferable to use a material for layer 113 that has a larger band gap than the luminescent material contained in layer 111. This makes it possible to suppress energy transfer from excitons generated in layer 111 to layer 113.

[0147] [Materials with electron transport properties] For example, the organic compounds, metal complexes, or organic compounds having a π-electron-deficient heteroaromatic ring skeleton described in Embodiment 1 can be used as electron-transporting materials. The organic compounds described in Embodiment 1 have excellent electron transport properties, which allows for a lower driving voltage for light-emitting devices, and are therefore preferable.

[0148] Under the condition that the square root of the electric field strength [V / cm] is 600, the electron mobility is 1 × 10⁻⁶. -7 cm 2 / Vs or more, 5×10 -5 cm 2 Materials with a Vs of 0.5 / Vs or less can be suitably used as electron-transporting materials. This makes it possible to suppress electron transport in the electron transport layer, control the amount of electrons injected into the light-emitting layer, or prevent the light-emitting layer from becoming electron-excessive.

[0149] Examples of metal complexes that can be used include bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviated as BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviated as BAlq), bis(8-quinolinolato)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviated as ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviated as ZnBTZ), and the like.

[0150] Organic compounds having a π-electron-deficient heteroaromatic ring skeleton include, for example, heterocyclic compounds having a polyazole skeleton, heterocyclic compounds having a diazine skeleton, heterocyclic compounds having a pyridine skeleton, and heterocyclic compounds having a triazine skeleton. In particular, heterocyclic compounds having a diazine skeleton or a pyridine skeleton are preferred due to their good reliability. Furthermore, heterocyclic compounds having a diazine (pyrimidine or pyrazine) skeleton have high electron transport properties, which can reduce the driving voltage.

[0151] Examples of heterocyclic compounds having a polyazole skeleton include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviated as TAZ), and 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as O XD-7), 9-[4-(5-phenyl-1,3,4-oxadiazole-2-yl)phenyl]-9H-carbazole (abbreviated as CO11), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviated as TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviated as mDBTBIm-II), etc. can be used.

[0152] Examples of heterocyclic compounds having a diazine skeleton include 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), and 2-[3'-(9H-carbazole-9-yl)biphenyl-3-yl]dibenzo[f,h Quinoxaline (abbreviation: 2mCzBPDBq), 4,6-bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,8-bis[3-(dibenzothiophen-4-yl)phenyl]benzo[h]quinazoline (abbreviation: 4,8mDBtP2Bqn), etc. can be used.

[0153] Examples of heterocyclic compounds having a pyridine skeleton include 3,5-bis[3-(9H-carbazole-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), and others.

[0154] Examples of heterocyclic compounds having a triazine skeleton include 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)-1,1'-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn) and 2-[(1,1'-biphenyl)-4-yl]-4-phenyl-6-[9,9'-spirobi(9H-fluoren)-2-yl]-1,3,5-triazine (abbreviation: BP- SFTzn), 2-{3-[3-(benzo"b"naphtho[1,2-d]furan-8-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mBnfBPTzn), 2-{3-[3-(benzo"b"naphtho[1,2-d]furan-6-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mBnfBPTzn-02), etc. can be used.

[0155] [Materials containing an anthracene skeleton] Organic compounds having an anthracene skeleton can be used in layer 113. In particular, organic compounds containing both an anthracene skeleton and a heterocyclic skeleton can be preferably used.

[0156] For example, an organic compound containing both an anthracene skeleton and a nitrogen-containing five-membered ring skeleton can be used. Alternatively, an organic compound containing both a nitrogen-containing five-membered ring skeleton with two heteroatoms in the ring and an anthracene skeleton can be used. Specifically, pyrazole rings, imidazole rings, oxazole rings, thiazole rings, etc., can be suitably used as the heterocyclic skeleton.

[0157] For example, an organic compound containing both an anthracene skeleton and a nitrogen-containing six-membered ring skeleton can be used. Alternatively, an organic compound containing both a nitrogen-containing six-membered ring skeleton with two heteroatoms in the ring and an anthracene skeleton can be used. Specifically, pyrazine rings, pyrimidine rings, pyridazine rings, etc., can be suitably used as the heterocyclic skeleton.

[0158] [Example of mixed material composition] Furthermore, a material composed of a mixture of multiple substances can be used in layer 113. Specifically, a mixed material containing an alkali metal, alkali metal compound, or alkali metal complex and an electron-transporting substance can be used in layer 113. It is more preferable that the HOMO level of the electron-transporting material is -6.0 eV or higher.

[0159] Furthermore, the mixed material can be suitably used in layer 113 in combination with a configuration in which the composite material is used in layer 104. For example, a composite material of a substance having acceptor properties and a material having hole transport properties can be used in layer 104. Specifically, a composite material of a substance having acceptor properties and a substance having a relatively deep HOMO level HOMO1 between -5.7 eV and -5.4 eV can be used in layer 104 (see Figure 1(B)). In particular, the mixed material can be suitably used in layer 113 in combination with a configuration in which the composite material is used in layer 104. This can improve the reliability of the light-emitting device.

[0160] Furthermore, it is preferable to combine the configuration in which the mixed material is used in layer 113 and the composite material is used in layer 104 with a configuration in which a hole-transporting material is used in layer 112. For example, a material having a HOMO level HOMO2 in the range of -0.2 eV to 0 eV relative to the relatively deep HOMO level HOMO1 can be used in layer 112 (see Figure 1(B)). This can improve the reliability of the light-emitting device.

[0161] A configuration in which alkali metals, alkali metal compounds, or alkali metal complexes are present in the thickness direction of layer 113 with a concentration difference (including cases where the concentration is zero) is preferred.

[0162] For example, metal complexes containing an 8-hydroxyquinolinate structure can be used. Alternatively, methyl-substituted metal complexes containing an 8-hydroxyquinolinate structure (e.g., 2-methyl-substituted or 5-methyl-substituted) can also be used.

[0163] As metal complexes containing the 8-hydroxyquinolinate structure, 8-hydroxyquinolinate-lithium (abbreviated as Liq), 8-hydroxyquinolinate-sodium (abbreviated as Naq), etc., can be used. In particular, monovalent metal ion complexes are preferred, among lithium complexes, and Liq is more preferred.

[0164] Example of Layer 112 configuration For example, a hole-transporting material can be used for layer 112. Layer 112 can also be referred to as a hole-transporting layer. It is preferable to use a material for layer 112 that has a larger band gap than the luminescent material contained in layer 111. This suppresses energy transfer from excitons generated in layer 111 to layer 112.

[0165] [Materials with hole transport properties] The hole mobility is 1 × 10⁻⁶. -6 cm 2 Materials with a Vs of 1 / Vs or higher can be suitably used as hole-transporting materials. Furthermore, the organic compounds described in Embodiment 1 can also be used as hole-transporting materials.

[0166] For example, amine compounds or organic compounds having a π-electron-rich heteroaromatic ring skeleton can be used in hole-transporting materials. Specifically, compounds having an aromatic amine skeleton, a carbazole skeleton, a thiophene skeleton, a furan skeleton, etc., can be used. Compounds having an aromatic amine skeleton or a carbazole skeleton are particularly preferred because they offer good reliability, high hole transportability, and contribute to reducing the driving voltage.

[0167] Examples of compounds having an aromatic amine skeleton include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated as BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated as mBPAFLP), and 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCBA1BP). ,4'-diphenyl-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]spiro-9,9'-bifluoren-2-amine (abbreviation: PCBASF), etc. can be used.

[0168] Examples of compounds having a carbazole skeleton include 1,3-bis(N-carbazolyl)benzene (abbreviated as mCP), 4,4'-di(N-carbazolyl)biphenyl (abbreviated as CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviated as CzTP), 3,3'-bis(9-phenyl-9H-carbazole) (abbreviated as PCCP), and the like.

[0169] Examples of compounds having a thiophene skeleton include 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviated as DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviated as DBTFLP-III), 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviated as DBTFLP-IV), and others.

[0170] Examples of compounds having a furan skeleton include 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II), 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II), and others.

[0171] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0172] (Embodiment 3) In this embodiment, the configuration of a light-emitting device 150 according to one aspect of the present invention will be described with reference to Figure 1.

[0173] <Example configuration of light-emitting device 150> The light-emitting device 150 described in this embodiment includes an electrode 101, an electrode 102, a unit 103, and a layer 104. Electrode 102 has a region that overlaps with electrode 101, and unit 103 has a region sandwiched between electrode 101 and electrode 102. Layer 104 also has a region sandwiched between electrode 101 and unit 103. For example, the configuration described in Embodiment 2 can be used for unit 103.

[0174] <Example configuration of electrode 101> For example, a conductive material can be used for the electrode 101. Specifically, metals, alloys, conductive compounds, mixtures of these, and the like can be used for the electrode 101. For example, a material having a work function of 4.0 eV or more can be preferably used.

[0175] For example, indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, indium oxide containing tungsten oxide and zinc oxide (IWZO), and the like can be used.

[0176] Further, for example, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), a nitride of a metal material (e.g., titanium nitride), and the like can be used. Alternatively, graphene can be used.

[0177] Configuration Example of Layer 104 For example, a material having a hole-injecting property can be used for the layer 104. Further, the layer 104 can be referred to as a hole-injecting layer.

[0178] Specifically, a substance having an acceptor property can be used for the layer 104. Alternatively, a composite material of a substance having an acceptor property and a material having a hole-transporting property can be used for the layer 104. This makes it easy to inject holes from, for example, the electrode 101. Alternatively, the driving voltage of the light-emitting device can be reduced.

[0179] [Substance having acceptor property] Organic compounds and inorganic compounds can be used as the substance having an acceptor property. The substance having an acceptor property can extract electrons from an adjacent hole-transporting layer or a material having a hole-transporting property upon application of an electric field.

[0180] For example, a compound having an electron-withdrawing group (a halogen group or a cyano group) can be used as an acceptor substance. Organic compounds having acceptor properties are easily vapor-deposited and easily formed into a film. Thereby, the productivity of light-emitting devices can be improved.

[0181] Specifically, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ), chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN), 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ), 2-(7-dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyren-2-ylidene)malononitrile, and the like can be used.

[0182] In particular, a compound in which an electron-withdrawing group is bonded to a fused aromatic ring having a plurality of heteroatoms, such as HAT-CN, is thermally stable and preferable.

[0183] In addition, [3]radialene derivatives having an electron-withdrawing group (particularly a halogen group such as a fluoro group or a cyano group) are preferable because they have extremely high electron acceptability.

[0184] Specifically, α,α',α''-1,2,3-cyclopropanetriylidenetris[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α',α''-1,2,3-cyclopropanetriylidenetris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], α,α',α''-1,2,3-cyclopropanetriylidenetris[2,3,4,5,6-pentafluorobenzeneacetonitrile], and the like can be used.

[0185] Further, molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide, and the like can be used as an acceptor substance.

[0186] Furthermore, phthalocyanine-based complex compounds such as phthalocyanine (abbreviated as H2Pc) and copper phthalocyanine (CuPc), and compounds having an aromatic amine skeleton such as 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated as DPAB) and N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviated as DNTPD) can be used.

[0187] Furthermore, polymers such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) can be used.

[0188] [Example of composite material composition 1] Furthermore, materials composed of multiple types of substances can be used as materials with hole injection properties. For example, a material with acceptor properties and a material with hole transport properties can be used as a composite material. This allows not only materials with large work functions but also materials with small work functions to be used for the electrode 101. Alternatively, the material to be used for the electrode 101 can be selected from a wide range of materials, regardless of the work function.

[0189] For example, compounds having an aromatic amine skeleton, carbazole derivatives, aromatic hydrocarbons, aromatic hydrocarbons having a vinyl group, and polymer compounds (oligomers, dendrimers, polymers, etc.) can be used as hole transport materials in composite materials. Furthermore, if the hole mobility is 1 × 10⁻⁶ -6 cm 2 Materials with a Vs of 1 / V or higher can be suitably used as materials with hole transport properties in composite materials.

[0190] Furthermore, materials with relatively deep HOMO levels can be suitably used as hole-transporting materials in composite materials. Specifically, it is preferable that the HOMO level is between -5.7 eV and -5.4 eV, as this facilitates the injection of holes into unit 103, or into layer 112, or improves the reliability of the light-emitting device.

[0191] Examples of compounds having an aromatic amine skeleton include N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviated as DTDPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated as DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviated as DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviated as DPA3B).

[0192] Examples of carbazole derivatives include 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarb You can use zole (abbreviated as PCzPCN1), 4,4'-di(N-carbazolyl)biphenyl (abbreviated as CBP), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene (abbreviated as TCPB), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as CzPA), 1,4-bis[4-(N-carbazolyl)phenyl]-2,3,5,6-tetraphenylbenzene, etc.

[0193] Examples of aromatic hydrocarbons include 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 2-tert-butyl-9,10-di(1-naphthyl)anthracene, 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 2-tert-butyl-9,10-bis(4-phenylphenyl)anthracene (abbreviation: t-BuDBA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 9,10-diphenylanthracene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation: t-BuAnth), 9,10-bis(4-methyl-1-naphthyl)anthracene (abbreviation: DMNA), and 2-tert-butyl-9,10 -Bis[2-(1-naphthyl)phenyl]anthracene, 9,10-bis[2-(1-naphthyl)phenyl]anthracene, 2,3,6,7-tetramethyl-9,10-di(1-naphthyl)anthracene, 2,3,6,7-tetramethyl-9,10-di(2-naphthyl)anthracene, 9,9'-bianthryl, 10,10'-diphenyl-9,9'-bianthryl, 10,10'-bis(2-phenylphenyl)-9,9'-bianthryl, 10,10'-bis[(2,3,4,5,6-pentaphenyl)phenyl]-9,9'-bianthryl, anthracene, tetracene, rubrene, perylene, 2,5,8,11-tetra(tert-butyl)perylene, pentacene, coronene, etc. can be used.

[0194] Examples of aromatic hydrocarbons having a vinyl group include 4,4'-bis(2,2-diphenylvinyl)biphenyl (abbreviated as DPVBi), 9,10-bis[4-(2,2-diphenylvinyl)phenyl]anthracene (abbreviated as DPVPA), and the like.

[0195] Examples of polymer compounds that can be used include poly(N-vinylcarbazole) (abbreviated as PVK), poly(4-vinyltriphenylamine) (abbreviated as PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated as PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated as Poly-TPD), and the like.

[0196] Furthermore, for example, substances comprising any of the carbazole skeleton, dibenzofuran skeleton, dibenzothiophene skeleton, and anthracene skeleton can be suitably used as hole-transporting materials in composite materials. In addition, substances comprising aromatic amines having substituents including a dibenzofuran ring or a dibenzothiophene ring, aromatic monoamines having a naphthalene ring, or aromatic monoamines in which a 9-fluorenyl group is bonded to the nitrogen of the amine via an arylene group can be used as hole-transporting materials in composite materials. Moreover, using a substance having an N,N-bis(4-biphenyl)amino group can improve the reliability of light-emitting devices.

[0197] Examples of these materials include N-(4-biphenyl)-6,N-diphenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BnfABP), N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf), 4,4'-bis(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)-4''-phenyltriphenylamine (abbreviation: BnfBB1BP), and N,N-bis(4-biphenyl)benzo[b]naphtho[1,2 -d]furan-6-amine (abbreviation: BBABnf(6)), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf(8)), N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviation: BBABnf(II)(4)), N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP), N-[4-(dibenzothiophen-4-yl)phenyl]-N-phenyl -4-biphenylamine (abbreviation: ThBA1BP), 4-(2-naphthyl)-4',4''-diphenyltriphenylamine (abbreviation: BBAβNB), 4-[4-(2-naphthyl)phenyl]-4',4''-diphenyltriphenylamine (abbreviation: BBAβNBi), 4,4'-diphenyl-4''-(6;1'-binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβNB), 4,4'-diphenyl-4''-(7;1'-binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβNB-0 3) 4,4'-diphenyl-4''-(7-phenyl)naphthyl-2-yltriphenylamine (abbreviation: BBAPβNB-03), 4,4'-diphenyl-4''-(6;2'-binaphthyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B), 4,4'-diphenyl-4''-(7;2'-binaphthyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B-03), 4,4'-diphenyl-4''-(4;2'-binaphthyl-1-yl)triphenylamine (abbreviation: BBAβNαNB), 4,4'-Diphenyl-4''-(5;2'-binaphthyl-1-yl)triphenylamine (abbreviation: BBAβNαNB-02), 4-(4-biphenylyl)-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: TPBiAβNB), 4-(3-biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: mTPBiAβNBi), 4-(4-biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4' '-phenyltriphenylamine (abbreviation: TPBiAβNBi), 4-phenyl-4'-(1-naphthyl)triphenylamine (abbreviation: αNBA1BP), 4,4'-bis(1-naphthyl)triphenylamine (abbreviation: αNBB1BP), 4,4'-diphenyl-4''-[4'-(carbazole-9-yl)biphenyl-4-yl]triphenylamine (abbreviation: YGTBi1BP), 4'-[4-(3-phenyl-9H-carbazole-9-yl)phenyl]tris(1, 1'-biphenyl-4-yl)amine (abbreviation: YGTBi1BP-02), 4-[4'-(carbazole-9-yl)biphenyl-4-yl]-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: YGTBiβNB), N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-N-[4-(1-naphthyl)phenyl]-9,9'-spirobio[9H-fluorene]-2-amine (abbreviation: PCBNBSF), N,N-bis([1,1'-bi Phenyl]-4-yl)-9,9'-spirobio[9H-fluorene]-2-amine (abbreviation: BBASF), N,N-bis([1,1'-biphenyl]-4-yl)-9,9'-spirobio[9H-fluorene]-4-amine (abbreviation: BBASF(4)), N-(1,1'-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobio(9H-fluorene)-4-amine (abbreviation: oFBiSF), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzofuran-4-amine (abbreviation: FrBiF), N-[4-(1-naphthyl)phenyl]-N-[3-(6-phenyldibenzofuran-4-yl)phenyl]-1-naphthylamine (abbreviation: mPDBfBNBN), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-phenyl-4' -[4-(9-phenylfluoren-9-yl)phenyl]triphenylamine (abbreviation: BPAFLBi), 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'- Di(1-naphthyl)-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBNBB), N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]spiro-9,9'-bifluoren-2-amine (abbreviation: PCBASF), N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF), N,N-bis(9 ,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio-9H-fluoren-4-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio-9H-fluoren-3-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio-9H-fluoren-2-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio-9H-fluoren-1-amine, etc. can be used.

[0198] [Example of composite material composition 2] For example, a composite material containing an acceptor substance, a hole-transporting material, and an alkali metal fluoride or an alkaline earth metal fluoride can be used as a hole-injecting material. In particular, a composite material having a fluorine atom content of 20% or more in terms of atomic ratio can be preferably used. This enables the refractive index of the layer 104 to be lowered. Alternatively, a layer with a low refractive index can be formed inside the light-emitting device. Alternatively, the external quantum efficiency of the light-emitting device can be improved.

[0199] Note that this embodiment can be appropriately combined with other embodiments shown in this specification.

[0200] (Embodiment 4) In this embodiment, a structure of a light-emitting device 150 according to one aspect of the present invention is described with reference to FIG. 1.

[0201] <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, and a layer 105. The electrode 102 has a region overlapping with the electrode 101, the unit 103 has a region sandwiched between the electrode 101 and the electrode 102, and the layer 105 has a region sandwiched between the unit 103 and the electrode 102. Note that for example, the structure described in Embodiment 2 can be used for the unit 103.

[0202] <Configuration Example of Electrode 102> For example, a conductive material can be used for the electrode 102. Specifically, a metal, an alloy, a conductive compound, a mixture thereof, or the like can be used for the electrode 102. For example, a material having a lower work function than that of the electrode 101 is preferably used for the electrode 102. Specifically, a material with a work function of 3.8 eV or less is preferable.

[0203] 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, or an alloy containing any of these elements can be used for the electrode 102.

[0204] Specifically, lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), strontium (Sr), europium (Eu), ytterbium (Yb), and alloys containing these elements (MgAg, AlLi) can be used for electrode 102.

[0205] Example of Layer 105 configuration For example, an electron-injection material can be used for layer 105. Layer 105 can also be referred to as an electron-injection layer.

[0206] Specifically, a donor material can be used in layer 105. Alternatively, a composite material of a donor material and an electron-transporting material can be used in layer 105. Alternatively, an electride can be used in layer 105. This makes it easier to inject electrons, for example, from electrode 102. Alternatively, not only materials with a small work function but also materials with a large work function can be used in electrode 102. Alternatively, a material for electrode 102 can be selected from a wide range of materials, regardless of the work function. Specifically, Al, Ag, ITO, silicon, or indium oxide-tin oxide containing silicon oxide can be used in electrode 102. Alternatively, the driving voltage of the light-emitting device can be reduced.

[0207] [Substances with donor properties] For example, alkali metals, alkaline earth metals, rare earth metals, or compounds thereof (oxides, halides, carbonates, etc.) can be used as donor substances. Alternatively, organic compounds such as tetratianaphthalene (abbreviated as TTN), nickerosene, and decamethylnickerosene can also be used as donor substances.

[0208] Examples of alkali metal compounds (including oxides, halides, and carbonates) that can be used include lithium oxide, lithium fluoride (LiF), cesium fluoride (CsF), lithium carbonate, cesium carbonate, 8-hydroxyquinolinatolithium (abbreviated as Liq), etc.

[0209] As alkaline earth metal compounds (including oxides, halides, and carbonates), calcium fluoride (CaF2), etc., can be used.

[0210] [Example of composite material composition 1] Furthermore, materials composed of multiple types of substances can be used as materials with electron injection properties. For example, a substance with donor properties and a material with electron transport properties can be used as a composite material.

[0211] [Materials with electron transport properties] For example, an electron-transporting material that can be used in unit 103 can be used in a composite material.

[0212] [Example of composite material composition 2] Furthermore, a composite material can be made from a microcrystalline alkali metal fluoride and an electron-transporting material. Alternatively, a composite material can be made from a microcrystalline alkaline earth metal fluoride and an electron-transporting material. In particular, a composite material containing 50 wt% or more of alkali metal fluoride or alkaline earth metal fluoride can be suitably used. Alternatively, a composite material containing an organic compound having a bipyridine skeleton can be suitably used. This can lower the refractive index of layer 104, or improve the external quantum efficiency of the light-emitting device.

[0213] [Electride] For example, a material obtained by adding a high concentration of electrons to a mixed oxide of calcium and aluminum can be used as an electron-injection material.

[0214] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0215] (Embodiment 5) In this embodiment, the configuration of a light-emitting device 150 according to one aspect of the present invention will be described with reference to Figure 2(A).

[0216] Figure 2(A) is a cross-sectional view illustrating the configuration of a light-emitting device according to one embodiment of the present invention.

[0217] <Example configuration of light-emitting device 150> Furthermore, the light-emitting device 150 described in this embodiment includes an electrode 101, an electrode 102, a unit 103, and an intermediate layer 106 (see Figure 2(A)). Electrode 102 has a region that overlaps with electrode 101, and unit 103 has a region sandwiched between electrode 101 and electrode 102. The intermediate layer 106 has a region sandwiched between unit 103 and electrode 102.

[0218] 《Example of the configuration of the intermediate layer 106》 The intermediate layer 106 comprises layer 106A and layer 106B. Layer 106B includes a region sandwiched between layer 106A and electrode 102.

[0219] 《Example of Layer 106A Configuration》 For example, an electron-transporting material can be used for layer 106A. Layer 106A can also be referred to as an electron relay layer. Using layer 106A allows the layer in contact with the anode side of layer 106A to be separated from the layer in contact with the cathode side of layer 106A. This reduces the interaction between the layer in contact with the anode side of layer 106A and the layer in contact with the cathode side of layer 106A. Electrons can be smoothly supplied to the layer in contact with the anode side of layer 106A.

[0220] A material having a LUMO level between the LUMO level of an acceptor material contained in the layer in contact with the anode side of layer 106A and the LUMO level of a material contained in the layer in contact with the cathode side of layer 106A can be suitably used in layer 106A.

[0221] For example, a material having a LUMO level in the range of -5.0 eV or higher, preferably -5.0 eV to -3.0 eV, can be used for layer 106A.

[0222] Specifically, phthalocyanine-based materials can be used in layer 106A. Alternatively, metal complexes having metal-oxygen bonds and aromatic ligands can be used in layer 106A.

[0223] 《Example of Layer 106B Configuration》 For example, a material that supplies electrons to the anode side and holes to the cathode side when a voltage is applied can be used for layer 106B. Specifically, electrons can be supplied to unit 103 located on the anode side. Layer 106B can also be called a charge generation layer.

[0224] Specifically, a hole-injection material that can be used in layer 104 can be used in layer 106B. For example, a composite material can be used in layer 106B. Alternatively, for example, a laminated film obtained by laminating a film containing the composite material with a film containing a hole-transporting material can be used in layer 106B.

[0225] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0226] (Embodiment 6) In this embodiment, the configuration of a light-emitting device 150 according to one aspect of the present invention will be described with reference to Figure 2(B).

[0227] Figure 2(B) is a cross-sectional view illustrating the configuration of a light-emitting device according to one embodiment of the present invention, which has a configuration different from that shown in Figure 2(A).

[0228] <Example configuration 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 Figure 2(B)). Electrode 102 has a region that overlaps with electrode 101, unit 103 has a region sandwiched between electrode 101 and electrode 102, and intermediate layer 106 has a region sandwiched between unit 103 and electrode 102. Unit 103(12) also has a region sandwiched between intermediate layer 106 and electrode 102, and unit 103(12) has the function of emitting light EL1(2).

[0229] The configuration comprising the intermediate layer 106 and multiple units is sometimes referred to as a stacked light-emitting device or a tandem light-emitting device. This allows for high-brightness light emission while maintaining a low current density. Alternatively, reliability can be improved. Alternatively, the drive voltage can be reduced when comparing devices with the same brightness. Alternatively, power consumption can be suppressed.

[0230] 《Example configuration of Unit 103(12)》 The configuration that can be used in unit 103 can also be used in unit 103(12). In other words, the light-emitting device 150 has multiple stacked units. Note that the number of stacked units is not limited to two, and three or more units can be stacked.

[0231] The same configuration as unit 103 can be used for unit 103(12). Alternatively, a different configuration from unit 103 can be used for unit 103(12).

[0232] For example, a configuration in unit 103(12) with a different emission color from that of unit 103 can be used. Specifically, a unit 103 that emits red and green light and a unit 103(12) that emits blue light can be used. This makes it possible to provide a light-emitting device that emits light of a desired color. For example, a light-emitting device that emits white light can be provided.

[0233] 《Example of the configuration of the intermediate layer 106》 The intermediate layer 106 has the function of supplying electrons to one of the units 103 or 103(12) and holes to the other. For example, the intermediate layer 106 described in Embodiment 5 can be used.

[0234] <Method for fabricating the light-emitting device 150> For example, the electrodes 101, 102, unit 103, intermediate layer 106, and unit 103(12) can be formed using dry, wet, vapor deposition, droplet ejection, coating, or printing methods. Furthermore, different methods can be used to form each component.

[0235] Specifically, the light-emitting device 150 can be manufactured using a vacuum deposition system, an inkjet system, a coating system such as a spin coater, a gravure printing system, an offset printing system, a screen printing system, and the like.

[0236] For example, electrodes can be formed using a wet method or a sol-gel method with a paste of a metallic material. Specifically, an indium oxide-zinc oxide film can be formed by sputtering using a target containing 1 to 20 wt% zinc oxide relative to indium oxide. Alternatively, an indium oxide (IWZO) film containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5 to 5 wt% tungsten oxide and 0.1 to 1 wt% zinc oxide relative to indium oxide.

[0237] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0238] (Embodiment 7) In this embodiment, the configuration of a functional panel 700 according to one aspect of the present invention will be described with reference to Figure 3.

[0239] <Example configuration of the 700 function panel> The functional panel 700 described in this embodiment includes a light-emitting device 150 and a light-emitting device 150(2) (Figure 3).

[0240] For example, the light-emitting devices described in Embodiments 2 to 6 can be used in the light-emitting device 150.

[0241] <Example configuration 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 Figure 3). Electrode 102 has a region that overlaps with electrode 101(2), and unit 103(2) has a region sandwiched between electrode 101(2) and electrode 102.

[0242] Electrode 101(2) may be at the same potential as electrode 101 or at a different potential. By supplying a different potential, the light-emitting device 150(2) can be driven under different conditions than the light-emitting device 150. Furthermore, the same materials that can be used for electrode 101 can be used for electrode 101(2).

[0243] Furthermore, the light-emitting device 150(2) has a layer 104 and a layer 105. Layer 104 has a region sandwiched between the electrode 101(2) and the unit 103(2), and layer 105 has a region sandwiched between the unit 103(2) and the electrode 102. Note that 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). This allows for the commonality of some components, or simplifies the manufacturing process.

[0244] <Example configuration of Unit 103(2)> Unit 103(2) has a single-layer structure or a laminated structure. For example, unit 103(2) comprises layer 111(2), layer 112 and layer 113 (see Figure 3).

[0245] Layer 111(2) includes a region sandwiched between layers 112 and 113, layer 112 includes a region sandwiched between electrode 101(2) and layer 111, and layer 113 includes a region sandwiched between electrode 102 and layer 111.

[0246] For example, a layer selected from functional layers such as an emissive layer, a hole transport layer, an electron transport layer, and a carrier block layer can be used in unit 103(2). In addition, a layer selected from functional layers such as a hole injection layer, an electron injection layer, an exciton block layer, and a charge generation layer can be used in unit 103(2).

[0247] 《Example of Layer 111(2) Configuration 1》 For example, a luminescent material or a luminescent material and a host material can be used for layer 111(2). Layer 111(2) can also be called a light-emitting layer. It is preferable to position layer 111(2) in a region where holes and electrons recombine. This allows the energy generated by carrier recombination to be efficiently emitted as light. It is also preferable to position layer 111(2) away from metals used for electrodes, etc. This suppresses the quenching phenomenon caused by metals used for electrodes, etc.

[0248] For example, a different luminescent material can be used in layer 111(2) than the luminescent material used in layer 111. Specifically, luminescent materials with different emission colors can be used in layer 111(2). This allows for the arrangement of light-emitting devices with different hues. Alternatively, additive color mixing can be performed using multiple light-emitting devices with different hues. Or, colors with hues that cannot be displayed by individual light-emitting devices can be represented.

[0249] For example, a light-emitting device that emits blue light, a light-emitting device that emits green light, and a light-emitting device that emits red light can be placed on the functional panel 700. Alternatively, a light-emitting device that emits white light, a light-emitting device that emits yellow light, and a light-emitting device that emits infrared light can be placed on the functional panel 700.

[0250] 《Example of Layer 111(2) Configuration 2》 For example, fluorescent materials, phosphorescent materials, or materials exhibiting thermally activated delayed fluorescence (TADF) (also known as TADF materials) can be used as luminescent materials. This allows the energy generated by carrier recombination to be released from the luminescent material as photo-EL2 (see Figure 3).

[0251] [Fluorescent material] For example, a fluorescent material that can be used in layer 111 can be used in layer 111(2). However, this is not limited to this.

[0252] [Phosphorescent material] A phosphorescent material can be used in layer 111(2). For example, the phosphorescent materials exemplified below can be used in layer 111(2). However, this is not limited to these examples.

[0253] For example, organometallic iridium complexes having a 4H-triazole skeleton, organometallic iridium complexes having a 1H-triazole skeleton, organometallic iridium complexes having an imidazole skeleton, organometallic iridium complexes with a phenylpyridine derivative having an electron-withdrawing group as a ligand, organometallic iridium complexes having a pyrimidine skeleton, organometallic iridium complexes having a pyrazine skeleton, organometallic iridium complexes having a pyridine skeleton, rare earth metal complexes, platinum complexes, etc., can be used in layer 111(2).

[0254] [Phosphorescent material (blue)] Examples of organometallic iridium complexes having a 4H-triazole skeleton include Tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazole-3-yl-κN 2[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.

[0255] Examples of organometallic iridium complexes having a 1H-triazole skeleton include tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(Mptz1-mp)3]), tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Prptz1-Me)3]), etc.

[0256] Examples of organometallic iridium complexes having an imidazole skeleton include 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]phenanthridine]iridium(III) (abbreviation: [Ir(dmpimpt-Me)3]), etc.

[0257] Examples of organometallic iridium complexes using phenylpyridine derivatives having electron-withdrawing groups as ligands include bis[2-(4',6'-difluorophenyl)pyridinate-N,C 2’ Iridium(III) tetrakis(1-pyrazolyl) borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridinate-N,C 2’ Iridium(III) picolinate (abbreviation: Firpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinate-N,C 2’Iridium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyridinate-N,C 2’ Iridium(III) acetylacetonate (abbreviated as FIracac), etc., can be used.

[0258] These compounds exhibit blue phosphorescence and have emission wavelength peaks between 440 nm and 520 nm.

[0259] [Phosphorescent material (green)] Examples of organometallic iridium complexes having a pyrimidine skeleton include tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)3]), tris(4-t-butyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonato)bis(6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [ Ir(tBuppm)2(acac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]), (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm)2(acac)]), (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)2(acac)]), etc. can be used.

[0260] Examples of organometallic iridium complexes having a pyrazine skeleton include (acetylacetonato)bis(3,5-dimethyl-2-phenylpyradinato)iridium(III) (abbreviation: [Ir(mppr-Me)2(acac)]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyradinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]), etc.

[0261] Examples of organometallic iridium complexes having a pyridine skeleton include tris(2-phenylpyridinato-N,C) 2’ Iridium(III) (abbreviation: [Ir(ppy)3]), bis(2-phenylpyridinate-N,C) 2’ Iridium(III) acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), bis(benzo[h]quinolinate)iridium(III) acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), tris(benzo[h]quinolinate)iridium(III) (abbreviation: [Ir(bzq)3]), tris(2-phenylquinolinate-N,C) 2’ Iridium(III) (abbreviation: [Ir(pq)3]), bis(2-phenylquinolinato-N,C) 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(pq)2(acac)]), [2-d3-methyl-8-(2-pyridinyl-κN)benzoflof[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridinyl-κN 2 [Ir(5mppy-d3)2(mbfpypy-d3)], [2-d3-methyl-(2-pyridinyl-κN)benzofl[2,3-b]pyridine-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(ppy)2(mbfpypy-d3)]), etc. can be used.

[0262] Examples of rare earth metal complexes include tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [Tb(acac)3(Phen)]).

[0263] These compounds primarily exhibit green phosphorescence and have emission wavelength peaks between 500 nm and 600 nm. Furthermore, organometallic iridium complexes with a pyrimidine skeleton are remarkably superior in terms of reliability or luminescence efficiency.

[0264] [Phosphorescent material (red)] Examples of organometallic iridium complexes having a pyrimidine skeleton include (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinato](dipvaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)]), bis[4,6-di(naphthalene-1-yl)pyrimidinato](dipvaloylmethanato)iridium(III) (abbreviation: [Ir(d1npm)2(dpm)]), etc.

[0265] Examples of organometallic iridium complexes having a pyrazine skeleton include (acetylacetonato)bis(2,3,5-triphenylpyradinato)iridium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2,3,5-triphenylpyradinato)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(tppr)2(dpm)]), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq)2(acac)]), etc.

[0266] Examples of organometallic iridium complexes having a pyridine skeleton include tris(1-phenylisoquinolinato-N,C) 2’ Iridium(III) (abbreviation: [Ir(piq)3]), bis(1-phenylisoquinolinato-N,C) 2’ Iridium(III) acetylacetonate (abbreviation: [Ir(piq)2(acac)]), etc., can be used.

[0267] Examples of rare earth metal complexes that can be used include tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: [Eu(DBM)3(Phen)]), tris[1-(2-tenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: [Eu(TTA)3(Phen)]), etc.

[0268] Examples of platinum complexes that can be used include 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviated as PtOEP).

[0269] These compounds exhibit red phosphorescence and have an emission peak between 600 nm and 700 nm. Furthermore, organometallic iridium complexes with a pyrazine skeleton produce red emission with a chromaticity suitable for use in display devices.

[0270] [Substances exhibiting thermally activated delayed fluorescence (TADF)] TADF material can be used in layer 111(2). For example, the TADF material exemplified below can be used as a luminescent material. However, it is not limited to this.

[0271] TADF materials have a small difference between the S1 and T1 energy levels, allowing for reverse intersystem crossing (upconversion) from a triplet excited state to a singlet excited state with minimal thermal energy. This enables efficient generation of singlet excited states from triplet excited states. Furthermore, the triplet excitation energy can be converted into luminescence.

[0272] Furthermore, an excited complex (also called an exciplex) that forms an excited state with two types of substances has an extremely small difference between the S1 and T1 levels and functions as a TADF material that can convert triplet excitation energy into singlet excitation energy.

[0273] Furthermore, the phosphorescence spectrum observed at low temperatures (e.g., 10K to 77K) can be used as an indicator of the T1 level. For TADF materials, when a tangent is drawn at the short-wavelength tail of the fluorescence spectrum and the energy at the wavelength of the extrapolation is taken as the S1 level, and when a tangent is drawn at the short-wavelength tail of the phosphorescence spectrum and the energy at the wavelength of the extrapolation is taken as the T1 level, it is preferable that the difference between S1 and T1 is 0.3 eV or less, and more preferably 0.2 eV or less.

[0274] Furthermore, when using TADF material as a light-emitting material, it is preferable that the S1 level of the host material is higher than the S1 level of the TADF material. Also, it is preferable that the T1 level of the host material is higher than the T1 level of the TADF material.

[0275] 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.

[0276] Specifically, the following can be used: protoporphyrin-tin fluoride complex (SnF2(Proto IX)), mesoporphyrin-tin fluoride complex (SnF2(Meso IX)), hematoporphyrin-tin fluoride complex (SnF2(Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complex (SnF2(Copro III-4Me)), octaethylporphyrin-tin fluoride complex (SnF2(OEP)), etioporphyrin-tin fluoride complex (SnF2(Etio I)), octaethylporphyrin-platinum chloride complex (PtCl2OEP), etc., whose structural formulas are shown below.

[0277] [ka]

[0278] Furthermore, for example, heterocyclic compounds having one or both of a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring can be used as TADF materials.

[0279] Specifically, the structural formulas are as follows: 2-(biphenyl-4-yl)-4,6-bis(12-phenylindoro[2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ), 9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazol (abbreviation: PCCzTzn), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 2-[4-(10H-phenoxazine-10-yl)phenyl]-4 ,6-diphenyl-1,3,5-triazine (abbreviated as PXZ-TRZ), 3-[4-(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (abbreviated as PPZ-3TPT), 3-(9,9-dimethyl-9H-acridine-10-yl)-9H-xanthene-9-one (abbreviated as ACRXTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviated as DMAC-DPS), 10-phenyl-10H,10'H-spiro[acridine-9,9'-anthracene]-10'-one (abbreviated as ACRSA), etc. can be used.

[0280] [ka]

[0281] The heterocyclic compound is preferred because it has both a π-electron-excess heteroaromatic ring and a π-electron-deficient heteroaromatic ring, resulting in high electron transport and hole transport properties. In particular, among the skeletons having a π-electron-deficient heteroaromatic ring, the pyridine skeleton, diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton), and triazine skeleton are preferred because they are stable and reliable. In particular, the benzoflopyrimidine skeleton, benzothienopyrimidine skeleton, benzoflopyrazine skeleton, and benzothienopyrazine skeleton are preferred because they have high acceptability and are reliable.

[0282] Furthermore, among skeletons having a π-electron-excess heteroaromatic ring, the acridine skeleton, phenoxazine skeleton, phenothiazine skeleton, furan skeleton, thiophene skeleton, and pyrrole skeleton are stable and reliable, and therefore it is preferable to have at least one of these skeletons. Dibenzofuran is preferred as the furan skeleton, and dibenzothiophene is preferred as the thiophene skeleton. Indole, carbazole, indrocarbazole, bicarbazole, and 3-(9-phenyl-9H-carbazole-3-yl)-9H-carbazole are particularly preferred as the pyrrole skeleton.

[0283] Furthermore, a substance in which a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring are directly bonded is particularly preferable because both the electron-donating and electron-accepting properties of the π-electron-rich heteroaromatic ring are strengthened, resulting in a smaller energy difference between the S1 and T1 levels, thus efficiently obtaining thermally activated delayed fluorescence. Alternatively, an aromatic ring bonded to an electron-withdrawing group such as a cyano group may be used instead of the π-electron-deficient heteroaromatic ring. Additionally, aromatic amine skeletons, phenazine skeletons, and the like can be used as the π-electron-rich skeleton.

[0284] Furthermore, as π-electron-deficient skeletons, xanthene skeletons, thioxanthene dioxide skeletons, oxadiazole skeletons, triazole skeletons, imidazole skeletons, anthraquinone skeletons, boron-containing skeletons such as phenylborane or volanthrene, aromatic rings or heteroaromatic rings having a nitrile group or cyano group such as benzonitrile or cyanobenzene, carbonyl skeletons such as benzophenone, phosphine oxide skeletons, sulfone skeletons, and the like can be used.

[0285] Thus, a π-electron-deficient skeleton and a π-electron-excess skeleton can be used instead of at least one of a π-electron-deficient heteroaromatic ring and a π-electron-excess heteroaromatic ring.

[0286] 《Example of Layer 111(2) Configuration 3》 Materials with carrier transport properties can be used as the host material. For example, materials with hole transport properties, materials with electron transport properties, TADF materials, materials with anthracene skeletons, and mixed materials can be used as the host material. It is preferable to use a material with a larger band gap than the luminescent material contained in layer 111(2) as the host material. This makes it possible to suppress energy transfer from excitons generated in layer 111(2) to the host material.

[0287] [Materials with hole transport properties] The hole mobility is 1 × 10⁻⁶. -6 cm 2 Materials with a Vs of / Vs or higher can be suitably used as materials with hole transport properties.

[0288] For example, a hole-transporting material that can be used in layer 112 can be used in layer 111. Specifically, a hole-transporting material that can be used in a hole-transporting layer can be used in layer 111.

[0289] [Materials with electron transport properties] For example, an electron-transporting material that can be used in layer 113 can be used in layer 111. Specifically, an electron-transporting material that can be used in an electron transport layer can be used in layer 111.

[0290] [Materials containing an anthracene skeleton] Organic compounds having an anthracene skeleton can be used as host materials. In particular, organic compounds having an anthracene skeleton are suitable when fluorescent materials are used as luminescent materials. This makes it possible to realize light-emitting devices with good luminescence efficiency and durability.

[0291] Among organic compounds having an anthracene skeleton, organic compounds having a diphenylanthracene skeleton, particularly a 9,10-diphenylanthracene skeleton, are preferred because they are chemically stable. Furthermore, when the host material has a carbazole skeleton, it is preferred because the hole injection and transport properties are enhanced. In particular, when the host material contains a dibenzocarbazole skeleton, the HOMO level becomes about 0.1 eV shallower than that of carbazole, making it easier for holes to enter, and it is also preferred because it has excellent hole transport properties and high heat resistance. From the viewpoint of hole injection and transport properties, a benzofluorene skeleton or a dibenzofluorene skeleton may be used instead of a carbazole skeleton.

[0292] Therefore, substances having both a 9,10-diphenylanthracene skeleton and a carbazole skeleton, substances having both a 9,10-diphenylanthracene skeleton and a benzocarbazole skeleton, and substances having both a 9,10-diphenylanthracene skeleton and a dibenzocarbazole skeleton are preferred as host materials.

[0293] For example, 6-[3-(9,10-diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-{4-(9-phenyl-9H-fluoren-9-yl)biphenyl-4'-yl}anthracene (abbreviation: FLPPA), 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth), 9-phenyl-3-[4-(10-phenyl [Lu-9-anthryl)phenyl]-9H-carbazole (abbreviated as PCzPA), 9-[4-(10-phenyl-9-antracenyl)phenyl]-9H-carbazole (abbreviated as CzPA), 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated as cgDBCzPA), 3-[4-(1-naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviated as PCPN), etc. can be used.

[0294] In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA exhibit very good characteristics.

[0295] [Substances exhibiting thermally activated delayed fluorescence (TADF)] TADF materials can be used as host materials. When TADF materials are used as host materials, the triplet excitation energy generated by the TADF material can be converted into singlet excitation energy through reverse intersystem crossing. Furthermore, the excitation energy can be transferred to the light-emitting material. In other words, the TADF material functions as an energy donor, and the light-emitting material functions as an energy acceptor. This can increase the luminescence efficiency of the light-emitting device.

[0296] This is particularly effective when the light-emitting material is a fluorescent material. Furthermore, in order to obtain high luminescence efficiency, it is preferable that the S1 level of the TADF material is higher than that of the fluorescent material. Also, it is preferable that the T1 level of the TADF material is higher than that of the fluorescent material. Therefore, it is preferable that the T1 level of the TADF material is higher than that of the fluorescent material.

[0297] Furthermore, it is preferable to use a TADF material that exhibits emission that overlaps with the wavelength of the lowest-energy absorption band of the fluorescent material. This is preferable because it allows for smooth transfer of excitation energy from the TADF material to the fluorescent material, resulting in efficient emission.

[0298] Furthermore, for singlet excitation energy to be efficiently generated from triplet excitation energy by reverse intersystem crossing, it is preferable that carrier recombination occurs in the TADF material. It is also preferable that the triplet excitation energy generated in the TADF material does not transfer to the triplet excitation energy of the fluorescent substance. To achieve this, it is preferable that the fluorescent substance has protecting groups around the luminescent phosphoform (the skeleton that causes luminescence). Preferred protecting groups are substituents without π bonds, and saturated hydrocarbons are preferred. Specifically, examples include alkyl groups having 3 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 carbon atoms, and trialkylsilyl groups having 3 to 10 carbon atoms. It is even more preferable to have multiple protecting groups. Substituents without π bonds have poor carrier transport function, and therefore can increase the distance between the TADF material and the luminescent phosphoform of the fluorescent substance with little effect on carrier transport or carrier recombination.

[0299] Here, the term "luminescent phosphat" refers to the group of atoms (skeleton) that causes light emission in a fluorescent material. The luminescent phosphat preferably has a skeleton with π bonds, preferably contains an aromatic ring, and preferably has a fused aromatic ring or a fused heteroaromatic ring.

[0300] Examples of condensed aromatic rings or condensed heteroaromatic rings include phenanthrene skeletons, stilbene skeletons, acridone skeletons, phenoxazine skeletons, and phenothiazine skeletons. In particular, fluorescent materials having naphthalene skeletons, anthracene skeletons, fluorene skeletons, chrysene skeletons, triphenylene skeletons, tetracene skeletons, pyrene skeletons, perylene skeletons, coumarin skeletons, quinacridone skeletons, and naphthobisbenzofuran skeletons are preferred because they have high fluorescence quantum yields.

[0301] For example, TADF material, which can be used as a luminescent material, can be used as a host material.

[0302] [Example of mixed material composition 1] Furthermore, a material composed of a mixture of multiple substances can be used as the host material. For example, a material with electron-transporting properties and a material with hole-transporting properties can be used in the mixture. The weight ratio of the material with hole-transporting properties to the material with electron-transporting properties in the mixture should be such that the ratio of material with hole-transporting properties to the material with electron-transporting properties is 1:19 to 19:1. This allows for easy adjustment of the carrier transport properties of layer 111(2). In addition, the recombination region can be easily controlled.

[0303] [Example of mixed material composition 2] A material mixed with a phosphorescent substance can be used as a host material. The phosphorescent substance can also be used as an energy donor to supply excitation energy to a fluorescent substance when a fluorescent substance is used as the light-emitting material.

[0304] A mixed material containing a material that forms an excited complex can be used as the host material. For example, a material in which the emission spectrum of the formed excited complex overlaps with the wavelength of the lowest-energy absorption band of the luminescent substance can be used as the host material. This allows for smoother energy transfer and improved luminescence efficiency, or it can suppress the driving voltage.

[0305] A phosphorescent material can be used as at least one of the materials forming the excitation complex. This allows for the utilization of reverse intersystem crossing. Alternatively, the triplet excitation energy can be efficiently converted to the singlet excitation energy.

[0306] For a combination of materials to form an excited complex, it is preferable that the HOMO level of the hole-transporting material is higher than or equal to the HOMO level of the electron-transporting material. Alternatively, it is preferable that the LUMO level of the hole-transporting material is higher than or equal to the LUMO level of the electron-transporting material. This allows for efficient formation of the excited complex. The LUMO and HOMO levels of the materials can be derived from their electrochemical properties (reduction potential and oxidation potential). Specifically, the reduction potential and oxidation potential can be measured using cyclic voltammetry (CV) measurement.

[0307] The formation of excited complexes can be confirmed, for example, by comparing the emission spectra of a hole-transporting material, an electron-transporting material, and a mixed film made by mixing these materials, and observing that the emission spectrum of the mixed film shifts to a longer wavelength than the emission spectra of each individual material (or has a new peak on the longer wavelength side). Alternatively, it can be confirmed by comparing the transient photoluminescence (PL) of a hole-transporting material, the transient PL of an electron-transporting material, and the transient PL of a mixed film made by mixing these materials, and observing differences in the transient response, such as the transient PL lifetime of the mixed film having a longer lifetime component or a larger proportion of the delayed component than the transient PL lifetime of each individual material. Furthermore, the transient PL mentioned above can be replaced with transient electroluminescence (EL). That is, the formation of excited complexes can also be confirmed by comparing the transient EL of a hole-transporting material, the transient EL of an electron-transporting material, and the transient EL of a mixed film made by mixing these materials, and observing the differences in the transient response.

[0308] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0309] (Embodiment 8) In this embodiment, the configuration of a functional panel 700 according to one aspect of the present invention will be described with reference to Figure 4.

[0310] <Example configuration of function panel 700 1> The functional panel 700 described in this embodiment includes a light-emitting device 150 and an optical functional device 170 (see Figure 4(A)).

[0311] For example, the light-emitting devices described in Embodiments 2 to 6 can be used in the light-emitting device 150.

[0312] <Example configuration of optical functional device 170> The optical functional device 170 described in this embodiment includes an electrode 101S, an electrode 102, and a unit 103S. Electrode 102 has a region that overlaps with electrode 101S, and unit 103S has a region sandwiched between electrode 101S and electrode 102.

[0313] Furthermore, the optical functional device 170 has a layer 104 and a layer 105. Layer 104 has a region sandwiched between the electrode 101S and the unit 103S, and layer 105 has a region sandwiched between the unit 103S and the electrode 102. Note that a part of the configuration of the light-emitting device 150 can be used as a part of the configuration of the optical functional device 170. This allows for the commonality of some components, or simplifies the manufacturing process.

[0314] <Example configuration of Unit 103S 1> Unit 103S has a single-layer structure or a laminated structure. For example, unit 103S has layers 114, 112, and 113 (see Figure 4(A)).

[0315] Layer 114 includes a region sandwiched between layers 112 and 113, layer 112 includes a region sandwiched between electrode 101S and layer 114, and layer 113 includes a region sandwiched between electrode 102 and layer 114.

[0316] For example, a layer selected from functional layers such as a photoelectric conversion layer, a hole transport layer, an electron transport layer, and a carrier block layer can be used in unit 103S. Furthermore, a layer selected from functional layers such as an exciton block layer and a charge generation layer can also be used in unit 103S.

[0317] Unit 103S absorbs light hv and supplies electrons to one electrode and holes to the other electrode. For example, unit 103S supplies holes to electrode 101S and electrons to electrode 102.

[0318] Example of Layer 112 configuration For example, a material having hole-transporting properties can be used for layer 112. Layer 112 can also be referred to as a hole-transporting layer. For example, the configuration described in Embodiment 2 can be used for layer 112.

[0319] Example of Layer 113 configuration For example, materials with electron transport properties, materials with an anthracene skeleton, and mixed materials can be used in layer 113. For example, the configuration described in Embodiment 2 can be used in layer 113.

[0320] 《Example of Layer 114 Configuration 1》 For example, electron-accepting materials and electron-donating materials can be used in layer 114. Specifically, materials that can be used in organic solar cells can be used in layer 114. Layer 114 can also be called a photoelectric conversion layer. Layer 114 absorbs light hv and supplies electrons to one electrode and holes to the other electrode. For example, layer 114 supplies holes to electrode 101S and electrons to electrode 102.

[0321] [Examples of electron-accepting materials] For example, fullerene derivatives, non-fullerene electron acceptors, etc., can be used as electron-accepting materials.

[0322] As for electron-accepting materials, C 60 Fullerene, C 70 Fullerene, [6,6]-phenyl-C 71 -Methyl butyrate (abbreviation: PC71BM), [6,6]-phenyl-C 61-Methyl butyrate (abbreviation: PC61BM), 1',1'',4',4''-tetrahydro-di[1,4]methanonaphthaleno[1,2:2',3',56,60:2'',3''][5,6]fullerene-C 60 (Abbreviation: ICBA) etc. can be used.

[0323] Furthermore, perylene derivatives, compounds having a dicyanomethyleneindanone group, etc., can be used as non-fullerene electron acceptors. N,N'-dimethyl-3,4,9,10-perylenedicarboxymide (abbreviated as Me-PTCDI), etc., can be used. In addition, the organic compounds described in Embodiment 1 can also be used in the active layer. For example, ultraviolet light can be converted into photoelectric energy.

[0324] [Examples of electron-donating materials] For example, phthalocyanine compounds, tetracene derivatives, quinacridone derivatives, rubrene derivatives, etc., can be used as electron-donating materials.

[0325] Electron-donating materials that can be used include copper(II) phthalocyanine (abbreviated as CuPc), tin(II) phthalocyanine (abbreviated as SnPc), zinc phthalocyanine (abbreviated as ZnPc), tetraphenyldibenzoperifuranthene (abbreviated as DBP), rubrene, and others.

[0326] 《Example of Layer 114 Configuration 2》 For example, a single-layer structure or a multi-layer structure can be used for layer 114. Specifically, a bulk heterojunction type structure can be used for layer 114. Alternatively, a heterojunction type structure can be used for layer 114.

[0327] [Example of mixed material composition] For example, a mixed material containing electron-accepting materials and electron-donating materials can be used for layer 114. A configuration in which a mixed material containing electron-accepting materials and electron-donating materials is used for layer 114 can be called a bulk heterojunction type.

[0328] Specifically, C70 A mixed material containing fullerene and DBP can be used in layer 114.

[0329] [Example of heterozygous type] Layers 114N and 114P can be used for layer 114. Layer 114N has a region sandwiched between one electrode and layer 114P, and layer 114P has a region sandwiched between layer 114N and the other electrode. For example, layer 114N has a region sandwiched between electrode 102 and layer 114P, and layer 114P has a region sandwiched between layer 114N and electrode 101S (see Figure 4(B)).

[0330] n-type semiconductors can be used in layer 114N. For example, Me-PTCDI can be used in layer 114N.

[0331] Furthermore, a p-type semiconductor can be used in layer 114P. For example, rubrene can be used in layer 114P.

[0332] Furthermore, an optical functional device 170 having a configuration in which layer 114P is in contact with layer 114N can be called a PN junction type photodiode.

[0333] <Example configuration of Unit 103S 2> Unit 103S includes a layer 111(2), which has a region sandwiched between layers 114 and 113 (see Figure 4(C)).

[0334] Configuration example 2 of unit 103S differs from configuration example 1 of unit 103S in that it includes layer 111(2). Here, the differences will be explained in detail, and the parts that have the same configuration will be explained by referring to the explanation above.

[0335] 《Example of the structure of layer 111(2)》 For example, a luminescent material or a luminescent material and a host material can be used for layer 111(2). Layer 111(2) can also be called a light-emitting layer. It is preferable to position layer 111(2) in a region where holes and electrons recombine. This allows the energy generated by carrier recombination to be efficiently emitted as light. It is also preferable to position layer 111(2) away from metals used for electrodes, etc. This suppresses the quenching phenomenon caused by metals used for electrodes, etc.

[0336] Specifically, the configuration described in Embodiment 2 can be used for layer 111(2). In particular, a configuration that emits light of a wavelength that is less likely to be absorbed by layer 114 can be suitably used for layer 111(2). This makes it possible to extract the light EL2 emitted by layer 111(2) with high efficiency.

[0337] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0338] (Embodiment 9) This embodiment describes a light-emitting device using a light-emitting device described in any one of Embodiments 2 to 6.

[0339] In this embodiment, a light-emitting device manufactured using the light-emitting device described in any one of Embodiments 2 to 6 will be described with reference to Figure 5. Figure 5(A) is a top view showing the light-emitting device, and Figure 5(B) is a cross-sectional view obtained by cutting Figure 5(A) along A and C. This light-emitting device includes a drive circuit section (source line drive circuit 601), a pixel section 602, and a drive circuit section (gate line drive circuit 603), all indicated by dotted lines, to control the light emission of the light-emitting device. Furthermore, 604 is a sealing substrate, and 605 is a sealing material, with the area enclosed by the sealing material 605 being a space 607.

[0340] The routing wiring 608 is for transmitting signals input to the source line drive circuit 601 and the gate line drive circuit 603, and receives video signals, clock signals, start signals, reset signals, etc. from the FPC (flexible printed circuit) 609, which serves as an external input terminal. Although only the FPC is shown in this illustration, a printed circuit board (PWB) may be attached to this FPC. In this specification, the light-emitting device includes not only the light-emitting device itself, but also the state in which the FPC or PWB is attached to it.

[0341] Next, the cross-sectional structure will be explained using Figure 5(B). A drive circuit section and a pixel section are formed on the element substrate 610, and here, the source line drive circuit 601, which is the drive circuit section, and one pixel in the pixel section 602 are shown.

[0342] The element substrate 610 may be manufactured using a substrate made of glass, quartz, organic resin, metal, alloy, semiconductor, or other materials, as well as a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (Polyvinyl Fluoride), polyester, or acrylic resin.

[0343] The structure of the transistor used in the pixel or driving circuit is not particularly limited. For example, it may be an inverse staggered transistor or a staggered transistor. It may also be a top-gate or bottom-gate transistor. The semiconductor material used for the transistor is not particularly limited; for example, silicon, germanium, silicon carbide, gallium nitride, etc., can be used. Alternatively, an oxide semiconductor containing at least one of indium, gallium, and zinc, such as an In-Ga-Zn metal oxide, may be used.

[0344] The crystallinity of the semiconductor material used in the transistor is not particularly limited; amorphous semiconductors, crystalline semiconductors (microcrystalline semiconductors, polycrystalline semiconductors, single-crystal semiconductors, or semiconductors having a crystalline region in part) may be used. Using a crystalline semiconductor is preferable because it can suppress the degradation of transistor characteristics.

[0345] Here, it is preferable to use oxide semiconductors for semiconductor devices such as transistors used in the pixels or driving circuits described above, as well as transistors used in touch sensors and the like, which will be described later. In particular, it is preferable to use oxide semiconductors with a wider bandgap than silicon. By using oxide semiconductors with a wider bandgap than silicon, the current in the off state of the transistor can be reduced.

[0346] The above oxide semiconductor preferably contains at least indium (In) or zinc (Zn). More preferably, it is an oxide semiconductor containing an oxide represented as an In-M-Zn oxide (where M is a metal such as Al, Ti, Ga, Ge, Y, Zr, Sn, La, Ce, or Hf).

[0347] In particular, it is preferable to use an oxide semiconductor film as the semiconductor layer, which has multiple crystalline portions, the c-axis of which is oriented perpendicular to the surface on which the semiconductor layer is formed or to the upper surface of the semiconductor layer, and which does not have grain boundaries between adjacent crystalline portions.

[0348] By using such materials as semiconductor layers, fluctuations in electrical properties can be suppressed, enabling the realization of highly reliable transistors.

[0349] Furthermore, due to its low off-current, the transistor having the aforementioned semiconductor layer can retain the charge stored in the capacitor via the transistor for a long period of time. By applying such transistors to pixels, it becomes possible to maintain the gradation of the image displayed in each display area while simultaneously stopping the drive circuit. As a result, electronic devices with extremely reduced power consumption can be realized.

[0350] It is preferable to provide an undercoat to stabilize the characteristics of the transistor. As the undercoat, an inorganic insulating film such as a silicon oxide film, silicon nitride film, silicon oxynitride film, or silicon nitride film can be used and fabricated as a single layer or in layers. The undercoat can be formed using sputtering, CVD (Chemical Vapor Deposition) (plasma CVD, thermal CVD, MOCVD (Metal Organic CVD), etc.), ALD (Atomic Layer Deposition), coating, printing, etc. Note that the undercoat may be omitted if not necessary.

[0351] Note that FET623 is one of the transistors formed in the source line drive circuit 601. The drive circuit can be formed using various CMOS, PMOS, or NMOS circuits. In this embodiment, a driver-integrated type with the drive circuit formed on the substrate is shown, but this is not necessarily required, and the drive circuit can be formed externally instead of on the substrate.

[0352] Furthermore, although the pixel section 602 is formed by a plurality of pixels including a switching FET 611 and a current control FET 612 and a first electrode 613 electrically connected to its drain, it is not limited to this, and the pixel section may be a combination of three or more FETs and a capacitive element.

[0353] Furthermore, an insulator 614 is formed to cover the end of the first electrode 613. This can be formed by using a positive-type photosensitive acrylic resin film.

[0354] Furthermore, in order to ensure good coverage of the EL layer and the like that will be formed later, a curved surface with curvature is formed at the upper or lower end of the insulator 614. For example, when a positive-type photosensitive acrylic resin is used as the material for the insulator 614, it is preferable to have a curved surface with a radius of curvature (0.2 μm or more and 3 μm or less) only at the upper end of the insulator 614. In addition, either a negative-type photosensitive resin or a positive-type photosensitive resin can be used as the insulator 614.

[0355] An EL layer 616 and a second electrode 617 are formed on the first electrode 613, respectively. Here, it is desirable to use a material with a large work function for the first electrode 613 which functions as an anode. For example, in addition to single-layer films such as ITO film, silicon-containing indium tin oxide film, indium oxide film containing 2 wt% to 20 wt% zinc oxide, titanium nitride film, chromium film, tungsten film, Zn film, and Pt film, a laminate of titanium nitride film and a film mainly composed of aluminum, or a three-layer structure of titanium nitride film, a film mainly composed of aluminum, and titanium nitride film can be used. Furthermore, a laminated structure has low resistance as wiring, good ohmic contact can be obtained, and it can function as an anode.

[0356] Furthermore, the EL layer 616 is formed by various methods such as vapor deposition using a vapor deposition mask, inkjet printing, and spin coating. The EL layer 616 includes the configuration described in any one of Embodiments 2 to 6. In addition, other materials constituting the EL layer 616 may be low molecular weight compounds or high molecular weight compounds (including oligomers and dendrimers).

[0357] Furthermore, it is preferable to use a material with a small work function (such as Al, Mg, Li, Ca, or alloys or compounds thereof (MgAg, MgIn, AlLi, etc.)) for the second electrode 617, which is formed on the EL layer 616 and functions as a cathode. When light generated in the EL layer 616 is transmitted through the second electrode 617, it is preferable to use a laminate of a thin metal film and a transparent conductive film (such as ITO, indium oxide containing 2 wt% to 20 wt% zinc oxide, indium tin oxide containing silicon, zinc oxide (ZnO), etc.) as the second electrode 617.

[0358] The first electrode 613, the EL layer 616, and the second electrode 617 form a light-emitting device. This light-emitting device is the light-emitting device described in any one of Embodiments 2 to 6. The pixel portion has multiple light-emitting devices formed on it, and in the light-emitting device of this embodiment, both the light-emitting device described in any one of Embodiments 2 to 6 and light-emitting devices having other configurations may be mixed together.

[0359] Furthermore, by bonding the sealing substrate 604 to the element substrate 610 with the sealing material 605, the light-emitting device 618 is provided in the space 607 surrounded by the element substrate 610, the sealing substrate 604, and the sealing material 605. The space 607 is filled with a filler material, which may be an inert gas (such as nitrogen or argon) or a sealing material. A recess is formed in the sealing substrate, and a desiccant is placed therein to suppress deterioration due to the effects of moisture, which is a preferred configuration.

[0360] Furthermore, it is preferable to use epoxy resin or glass frit for the sealing material 605. It is also desirable that these materials are as impermeable to moisture and oxygen as possible. In addition to glass substrates or quartz substrates, plastic substrates made of FRP (Fiber Reinforced Plastics), PVF (Polyvinyl Fluoride), polyester, or acrylic resin can be used as the material for the sealing substrate 604.

[0361] Although not shown in Figures 5(A) and 5(B), 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. Alternatively, the protective film may be formed to cover the exposed portion of the sealing material 605. Furthermore, the protective film can be provided to cover the surface and sides of the pair of substrates, the sealing layer, the insulating layer, and other exposed sides.

[0362] The protective film can be made of a material that is impermeable to impurities such as water. Therefore, it is possible to effectively suppress the diffusion of impurities such as water from the outside to the inside.

[0363] Materials that constitute the protective film can include oxides, nitrides, fluorides, sulfides, ternary compounds, metals, or polymers. For example, materials containing aluminum oxide, hafnium oxide, hafnium silicate, lanthanum oxide, silicon oxide, strontium titanate, tantalum oxide, titanium oxide, zinc oxide, niobium oxide, zirconium oxide, tin oxide, yttrium oxide, cerium oxide, scandium oxide, erbium oxide, vanadium oxide, or indium oxide can be used. Other materials containing aluminum nitride, hafnium nitride, silicon nitride, tantalum nitride, titanium nitride, niobium nitride, molybdenum nitride, zirconium nitride, or gallium nitride can be used. Nitrides containing titanium and aluminum, oxides containing titanium and aluminum, oxides containing aluminum and zinc, sulfides containing manganese and zinc, sulfides containing cerium and strontium, oxides containing erbium and aluminum, oxides containing yttrium and zirconium can be used.

[0364] It is preferable to form the protective film using a film deposition method that provides good step coverage. One such method is atomic layer deposition (ALD). It is preferable to use a material that can be formed using the ALD method for the protective film. By using the ALD method, it is possible to form a dense protective film with reduced defects such as cracks or pinholes, or a protective film with a uniform thickness. Furthermore, it is possible to reduce the damage inflicted on the processed workpiece when forming the protective film.

[0365] For example, by using the ALD method to form a protective film, it is possible to create a uniform, low-defect protective film on surfaces with complex uneven shapes, or on the top, sides, and back surfaces of a touch panel.

[0366] As described above, a light-emitting device can be obtained using the light-emitting device described in any one of Embodiments 2 to 6.

[0367] Since the light-emitting device in this embodiment uses the light-emitting device described in any one of Embodiments 2 to 6, a light-emitting device with good characteristics can be obtained. Specifically, since the light-emitting device described in any one of Embodiments 2 to 6 has good luminous efficiency, it is possible to make a light-emitting device with low power consumption.

[0368] Figure 6 shows an example of a light-emitting device that is made full-color by forming a light-emitting device that emits white light and providing a colored layer (color filter), etc. Figure 6(A) shows a substrate 1001, a base 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 drive 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.

[0369] Furthermore, in Figure 6(A), the colored layers (red colored layer 1034R, green colored layer 1034G, and blue colored layer 1034B) are provided on a transparent substrate 1033. A black matrix 1035 may also be provided. The transparent substrate 1033 on which the colored layers and black matrix are provided is aligned and fixed to the substrate 1001. The colored layers and black matrix 1035 are covered with an overcoat layer 1036. In Figure 6(A), there is an emissive layer that emits light to the outside without transmitting through the colored layers, and an emissive layer that emits light to the outside by transmitting through each colored layer. Light that does not transmit through the colored layers is white, and light that transmits through the colored layers is red, green, and blue, so an image can be represented with four colored pixels.

[0370] Figure 6(B) shows an example in which colored layers (red colored layer 1034R, green colored layer 1034G, and blue colored layer 1034B) are formed between the gate insulating film 1003 and the first interlayer insulating film 1020. Thus, the colored layers may also be provided between the substrate 1001 and the encapsulating substrate 1031.

[0371] Furthermore, although the light-emitting device described above is a bottom-emission type device that extracts light from the substrate 1001 on which the FET is formed, it may also be a top-emission type device that extracts light from the sealing substrate 1031. A cross-sectional view of the top-emission type light-emitting device is shown in Figure 7. In this case, the substrate 1001 can be a substrate that does not transmit light. The process is the same as for the bottom-emission type light-emitting device until the connecting electrode that connects the FET and the anode of the light-emitting device is fabricated. After that, a third interlayer insulating film 1037 is formed covering the electrode 1022. This insulating film may also play a planarization role. The third interlayer insulating film 1037 can be formed using the same material as the second interlayer insulating film, as well as other known materials.

[0372] The first electrodes 1024W, 1024R, 1024G, and 1024B of the light-emitting device are designated as anodes here, but they may also be cathodes. Furthermore, in the case of a top-emission type light-emitting device as shown in Figure 7, it is preferable that the first electrodes be reflective electrodes. The configuration of the EL layer 1028 is as described as unit 103 in any one of Embodiments 2 to 6, and the element structure is such that white light emission can be obtained.

[0373] In the top emission structure shown in Figure 7, sealing can be performed with a sealing substrate 1031 having colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B). A black matrix 1035 may be provided on the sealing substrate 1031 so as to be located between pixels. The colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B) or the black matrix may be covered with an overcoat layer 1036. The sealing substrate 1031 should be a translucent substrate. In addition, although an example of full-color display using four colors, red, green, blue, and white, is shown here, it is not particularly limited, and full-color display may be performed using four colors, red, yellow, green, and blue, or three colors, red, green, and blue.

[0374] In top-emission type light-emitting devices, a microcavity structure can be suitably applied. A light-emitting device having a microcavity structure is obtained by using a reflective electrode as the first electrode and a semi-transparent / semi-reflective electrode as the second electrode. There is at least an EL layer between the reflective electrode and the semi-transparent / semi-reflective electrode, and there is at least a light-emitting layer that forms a light-emitting region.

[0375] The reflective electrode has a visible light reflectance of 40% to 100%, preferably 70% to 100%, and its resistivity is 1 × 10⁻⁶. -2 The film thickness is assumed to be Ωcm or less. Furthermore, the semi-transparent / semi-reflective electrode has a visible light reflectance of 20% to 80%, preferably 40% to 70%, and its resistivity is 1 × 10⁻⁶. -2 Assume the membrane is less than Ωcm in diameter.

[0376] The light emitted from the light-emitting layer contained in the EL layer is reflected by the reflective electrode and the semi-transparent / semi-reflective electrode, causing resonance.

[0377] This light-emitting device allows you to change the optical distance between the reflective electrode and the semi-transparent / semi-reflective electrode by changing the thickness of the transparent conductive film or the aforementioned composite material, carrier transport material, etc. This makes it possible to strengthen light of resonant wavelengths and attenuate light of non-resonant wavelengths between the reflective electrode and the semi-transparent / semi-reflective electrode.

[0378] Furthermore, since the light reflected back by the reflective electrode (first reflected light) interferes significantly with the light that directly enters the semi-transparent / semi-reflective electrode from the light-emitting layer (first incident light), it is preferable to adjust the optical distance between the reflective electrode and the light-emitting layer to (2n-1)λ / 4 (where n is a natural number greater than or equal to 1, and λ is the wavelength of the light emission to be amplified). By adjusting this optical distance, the phases of the first reflected light and the first incident light can be aligned, and the light emission from the light-emitting layer can be further amplified.

[0379] In the above configuration, the EL layer may have a structure with multiple light-emitting layers or a structure with a single light-emitting layer. For example, it may be applied to a configuration in which multiple EL layers are provided in a single light-emitting device with a charge generation layer in between, and one or more light-emitting layers are formed in each EL layer, in combination with the tandem light-emitting device configuration described above.

[0380] By incorporating a microcavity structure, it becomes possible to enhance the emission intensity in the front direction at specific wavelengths, thereby reducing power consumption. Furthermore, in the case of a light-emitting device that displays images using four sub-pixels of red, yellow, green, and blue, in addition to the brightness enhancement effect of yellow emission, a microcavity structure tailored to the wavelength of each color can be applied to all sub-pixels, resulting in a light-emitting device with excellent characteristics.

[0381] Since the light-emitting device in this embodiment uses the light-emitting device described in any one of Embodiments 2 to 6, a light-emitting device with good characteristics can be obtained. Specifically, since the light-emitting device described in any one of Embodiments 2 to 6 has good luminous efficiency, it is possible to make a light-emitting device with low power consumption.

[0382] Up to this point, we have described an active matrix type light-emitting device, but from here on we will describe a passive matrix type light-emitting device. Figure 8 shows a passive matrix type light-emitting device manufactured by applying the present invention. Figure 8(A) is a perspective view showing the light-emitting device, and Figure 8(B) is a cross-sectional view obtained by cutting Figure 8(A) along the X and Y lines. In Figure 8, an EL layer 955 is provided on the substrate 951 between electrodes 952 and 956. The ends of electrodes 952 are covered with an insulating layer 953. A partition layer 954 is provided on the insulating layer 953. The side walls of the partition layer 954 have a slope such that the distance between one side wall and the other side wall narrows as it approaches the substrate surface. In other words, the cross-section of the partition layer 954 in the short-side direction is trapezoidal, with the bottom side (facing the same direction as the surface direction of the insulating layer 953 and in contact with the insulating layer 953) being shorter than the top side (facing the same direction as the surface direction of the insulating layer 953 and not in contact with the insulating layer 953). By providing the partition layer 954 in this way, it is possible to prevent malfunctions of the light-emitting device caused by static electricity, etc. Furthermore, even in a passive matrix type light-emitting device, the light-emitting device described in any one of Embodiments 2 to 6 can be used, resulting in a light-emitting device with good reliability or low power consumption.

[0383] As described above, the light-emitting device is suitable for use as a display device for representing images because it is possible to control each of the numerous minute light-emitting devices arranged in a matrix.

[0384] Furthermore, this embodiment can be freely combined with other embodiments.

[0385] (Embodiment 10) In this embodiment, an example of using the light-emitting device described in any one of Embodiments 2 to 6 as an illumination device will be described with reference to Figure 9. Figure 9(B) is a top view of the illumination device, and Figure 9(A) is a cross-sectional view of ef in Figure 9(B).

[0386] In this embodiment, the lighting device has a first electrode 401 formed on a translucent substrate 400 which serves as a support. The first electrode 401 corresponds to the electrode 101 in any one of Embodiments 2 to 6. When light is extracted from the first electrode 401 side, the first electrode 401 is formed from a translucent material.

[0387] A pad 412 for supplying voltage to the second electrode 404 is formed on the substrate 400.

[0388] An EL layer 403 is formed on the first electrode 401. The EL layer 403 corresponds to the configuration of unit 103 in any one of Embodiments 2 to 6. For details of these configurations, please refer to the respective descriptions.

[0389] A second electrode 404 is formed by covering the EL layer 403. The second electrode 404 corresponds to electrode 102 in any one of Embodiments 2 to 6. When light emission is extracted from the first electrode 401 side, the second electrode 404 is formed of a material with high reflectivity. Voltage is supplied to the second electrode 404 by connecting it to the pad 412.

[0390] As described above, the lighting device shown in this embodiment has a light-emitting device having a first electrode 401, an EL layer 403, and a second electrode 404. Since this light-emitting device is a light-emitting device with high luminous efficiency, the lighting device in this embodiment can be a lighting device with low power consumption.

[0391] The lighting device is completed by fixing and sealing the substrate 400, on which the light-emitting device having the above configuration is formed, and the sealing substrate 407 using sealing materials 405 and 406. Either sealing material 405 or 406 may be used. In addition, a desiccant can be mixed into the inner sealing material 406 (not shown in Figure 9(B)), which allows for the adsorption of moisture and leads to improved reliability.

[0392] Furthermore, by extending the pad 412 and a portion of the first electrode 401 outside the sealing materials 405 and 406, it can be used as an external input terminal. Alternatively, an IC chip 420 with a converter or the like may be placed on top of it.

[0393] As described above, the lighting device described in this embodiment uses the light-emitting device described in any one of Embodiments 2 to 6 as the EL element, and can be a lighting device with low power consumption.

[0394] (Embodiment 11) This embodiment describes an example of an electronic device that includes a light-emitting device as described in any one of Embodiments 2 to 6. The light-emitting device described in any one of Embodiments 2 to 6 has good luminous efficiency and low power consumption. As a result, the electronic device described in this embodiment can be an electronic device having a light-emitting section with low power consumption.

[0395] Examples of electronic devices to which the above-mentioned light-emitting devices are applied include television equipment (also called televisions or television receivers), monitors for computers, digital cameras, digital video cameras, digital photo frames, mobile phones (also called mobile phones or mobile phone devices), portable game consoles, personal digital assistants, sound playback devices, and large game machines such as pachinko machines. Specific examples of these electronic devices are shown below.

[0396] Figure 10(A) shows an example of a television system. The television system has a display unit 7103 incorporated into a housing 7101. This figure also shows a configuration in which the housing 7101 is supported by a stand 7105. The display unit 7103 is capable of displaying images, and the display unit 7103 is configured by arranging the light-emitting devices described in any one of Embodiments 2 to 6 in a matrix.

[0397] The television system can be operated using the operation switches on the housing 7101 or a separate remote control unit 7110. The operation keys 7109 on the remote control unit 7110 allow for channel or volume control, and the image displayed on the display unit 7103 can be controlled. Alternatively, the remote control unit 7110 may be configured to include a display unit 7107 that displays information output from the remote control unit 7110.

[0398] The television system shall consist of a receiver or modem. The receiver will be able to receive general television broadcasts, and by connecting to a wired or wireless communication network via the modem, it will also be possible to perform one-way (from sender to receiver) or two-way (between sender and receiver, or between receivers, etc.) information communication.

[0399] Figure 10(B) shows a computer, which includes a main unit 7201, a housing 7202, a display unit 7203, a keyboard 7204, an external connection port 7205, a pointing device 7206, etc. This computer is manufactured by arranging the light-emitting devices described in any one of Embodiments 2 to 6 in a matrix and using them for the display unit 7203. The computer in Figure 10(B) may also take the form shown in Figure 10(C). The computer in Figure 10(C) is provided with a second display unit 7210 instead of the keyboard 7204 and pointing device 7206. The second display unit 7210 is a touch panel, and input can be performed by operating the input display shown on the second display unit 7210 with a finger or a dedicated pen. In addition to the input display, the second display unit 7210 can also display other images. The display unit 7203 may also be a touch panel. The two screens are connected by a hinge, which prevents problems such as scratching or damaging the screens when storing or transporting the device.

[0400] Figure 10(D) shows an example of a mobile terminal. The mobile phone includes a display unit 7402 incorporated into the housing 7401, as well as operation buttons 7403, an external connection port 7404, a speaker 7405, a microphone 7406, and the like. The mobile phone has a display unit 7402 made by arranging the light-emitting devices described in any one of Embodiments 2 to 6 in a matrix.

[0401] The mobile terminal shown in Figure 10(D) can also be configured to allow information input by touching the display unit 7402 with a finger or other object. In this case, operations such as making a phone call or composing an email can be performed by touching the display unit 7402 with a finger or other object.

[0402] The display unit 7402 has three main modes. The first is a display mode that primarily displays images, the second is an input mode that primarily inputs information such as text, and the third is a display + input mode that combines the display mode and the input mode.

[0403] For example, when making a phone call or composing an email, the display unit 7402 should be set to a text input mode, which primarily focuses on text input, and the user should perform the text input operation displayed on the screen. In this case, it is preferable to display a keyboard or number buttons on most of the screen of the display unit 7402.

[0404] Furthermore, by providing a detection device with a tilt sensor such as a gyroscope or accelerometer inside the mobile terminal, the orientation of the mobile terminal (portrait or landscape) can be determined, and the screen display of the display unit 7402 can be automatically switched accordingly.

[0405] Furthermore, the screen mode can be switched by touching the display unit 7402 or by operating the operation button 7403 on the housing 7401. It is also possible to switch modes depending on the type of image displayed on the display unit 7402. For example, if the image signal displayed on the display unit is video data, it can be switched to display mode; if it is text data, it can be switched to input mode.

[0406] Furthermore, in input mode, the system may detect a signal detected by the optical sensor of the display unit 7402 and, if there is no input via touch operation on the display unit 7402 for a certain period of time, control may be made to switch the screen mode from input mode to display mode.

[0407] The display unit 7402 can also function as an image sensor. For example, by touching the display unit 7402 with the palm or finger, palm prints, fingerprints, etc., can be captured to perform user authentication. Furthermore, by using a backlight that emits near-infrared light or a sensing light source that emits near-infrared light in the display unit, finger veins, palm veins, etc., can also be captured.

[0408] Figure 11(A) is a schematic diagram showing an example of a cleaning robot.

[0409] The cleaning robot 5100 has a display 5101 on its top surface, multiple cameras 5102 on its sides, a brush 5103, and control buttons 5104. Although not shown in the illustration, the cleaning robot 5100 also has wheels, a suction port, etc. on its underside. The cleaning robot 5100 is also equipped with various sensors, including an infrared sensor, an ultrasonic sensor, an accelerometer, a piezoelectric sensor, a light sensor, and a gyroscope. Furthermore, the cleaning robot 5100 is equipped with a means of wireless communication.

[0410] The cleaning robot 5100 is self-propelled, can detect dirt 5120, and can suck up the dirt through a suction port located on its underside.

[0411] Furthermore, the cleaning robot 5100 can analyze images captured by the camera 5102 to determine the presence or absence of obstacles such as walls, furniture, or steps. If the image analysis detects objects that could become entangled in the brush 5103, such as wiring, it can stop the brush 5103 from rotating.

[0412] The display 5101 can display information such as the remaining battery level or the amount of dirt collected. The path taken by the cleaning robot 5100 may also be displayed on the display 5101. Alternatively, the display 5101 may be a touch panel, and operation buttons 5104 may be provided on the display 5101.

[0413] The cleaning robot 5100 can communicate with a portable electronic device 5140, such as a smartphone. Images captured by the camera 5102 can be displayed on the portable electronic device 5140. Therefore, the owner of the cleaning robot 5100 can check the status of the room even when they are away from home. In addition, the display 5101 can be viewed on the portable electronic device 5140, such as a smartphone.

[0414] A light-emitting device according to one aspect of the present invention can be used in a display 5101.

[0415] The robot 2100 shown in Figure 11(B) includes a computing 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 movement mechanism 2108.

[0416] The microphone 2102 has the function of detecting the user's voice and ambient sounds. The speaker 2104 has the function of emitting sound. The robot 2100 can communicate with the user using the microphone 2102 and speaker 2104.

[0417] The display 2105 has the function of displaying various types of information. The robot 2100 can display the information desired by the user on the display 2105. The display 2105 may be equipped with a touch panel. The display 2105 may also be a detachable information terminal, and by installing it in a fixed position on the robot 2100, charging and data transfer can be made possible.

[0418] The upper camera 2103 and the lower camera 2106 have the function of imaging the area around the robot 2100. In addition, the obstacle sensor 2107 can detect the presence or absence of obstacles in the direction of travel when the robot 2100 moves forward using the movement mechanism 2108. The robot 2100 can recognize its surrounding environment and move safely using the upper camera 2103, the lower camera 2106 and the obstacle sensor 2107. The light-emitting device according to one aspect of the present invention can be used in the display 2105.

[0419] Figure 11(C) shows an example of a goggle-type display. The goggle-type display includes, for example, a housing 5000, a display unit 5001, a speaker 5003, an LED lamp 5004, operation keys (including a power switch or operation switch), connection terminals 5006, a sensor 5007 (including functions for measuring force, displacement, position, velocity, acceleration, angular velocity, rotational speed, distance, light, liquid, magnetism, temperature, chemical substances, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared radiation), a microphone 5008, a display unit 5002, a support unit 5012, an earphone 5013, etc.

[0420] A light-emitting device according to one aspect of the present invention can be used in the display unit 5001 and the display unit 5002.

[0421] Figure 12 shows an example in which the light-emitting device described in any one of Embodiments 2 to 6 is used in a desk lamp, which is a lighting device. The desk lamp shown in Figure 12 has a housing 2001 and a light source 2002, and the lighting device described in Embodiment 10 may be used as the light source 2002.

[0422] Figure 13 shows an example of using the light-emitting device described in any one of Embodiments 2 to 6 as an indoor lighting device 3001. Since the light-emitting device described in any one of Embodiments 2 to 6 is a light-emitting device with high luminous efficiency, it can be used as a lighting device with low power consumption. Furthermore, since the light-emitting device described in any one of Embodiments 2 to 6 can be made to cover a large area, it can be used as a large-area lighting device. In addition, since the light-emitting device described in any one of Embodiments 2 to 6 is thin, it can be used as a thin lighting device.

[0423] The light-emitting device described in any one of Embodiments 2 to 6 can also be mounted on the windshield or dashboard of an automobile. Figure 14 shows one embodiment in which the light-emitting device described in any one of Embodiments 2 to 6 is used on the windshield or dashboard of an automobile. Display areas 5200 to 5203 are display areas provided using the light-emitting device described in any one of Embodiments 2 to 6.

[0424] Display area 5200 and display area 5201 are display devices equipped with a light-emitting device according to any one of Embodiments 2 to 6, which is installed on the windshield of an automobile. The light-emitting device according to any one of Embodiments 2 to 6 can be made into a so-called see-through display device, where the opposite side is visible, by making the first electrode and the second electrode from translucent electrodes. If the display is in a see-through state, it can be installed on the windshield of an automobile without obstructing the view. When providing transistors for driving, it is preferable to use translucent transistors such as organic transistors made of organic semiconductor materials or transistors using oxide semiconductors.

[0425] The display area 5202 is a display device equipped with a light-emitting device described in any one of Embodiments 2 to 6, which is provided on the pillar. By displaying images from an imaging means provided on the vehicle body on the display area 5202, the field of view obstructed by the pillar can be supplemented. Similarly, the display area 5203 provided on the dashboard can compensate for blind spots and enhance safety by displaying images from an imaging means provided on the outside of the vehicle, which is obstructed by the vehicle body. By displaying images in a way that supplements the parts that are not visible, safety checks can be performed more naturally and without discomfort.

[0426] Display area 5203 can provide various information by displaying navigation information, speed or RPM, mileage, fuel level, gear status, air conditioning settings, etc. The display items and layout can be changed as needed to suit the user's preferences. This information can also be provided in display areas 5200 to 5202. Furthermore, display areas 5200 to 5203 can also be used as lighting devices.

[0427] Figures 15(A) to 15(C) also show the foldable portable information terminal 9310. Figure 15(A) shows the portable information terminal 9310 in its unfolded state. Figure 15(B) shows the portable information terminal 9310 in an intermediate state, transitioning from either the unfolded or folded state to the other. Figure 15(C) shows the portable information terminal 9310 in its folded state. The portable information terminal 9310 offers excellent portability in its folded state and excellent readability of the display due to its seamless, wide display area in its unfolded state.

[0428] The display panel 9311 is supported by three housings 9315 connected by a hinge 9313. The display panel 9311 may also be a touch panel (input / output device) equipped with a touch sensor (input device). Furthermore, the display panel 9311 can be reversibly transformed from an unfolded state to a folded state by bending the two housings 9315 via the hinge 9313. A light-emitting device according to one aspect of the present invention can be used in the display panel 9311.

[0429] Furthermore, the configuration shown in this embodiment can be used by appropriately combining the configurations shown in Embodiments 2 to 6.

[0430] As described above, the application range of the light-emitting device equipped with the light-emitting device described in any one of Embodiments 2 to 6 is extremely broad, and this light-emitting device can be applied to electronic devices in all fields. By using the light-emitting device described in any one of Embodiments 2 to 6, it is possible to obtain electronic devices with low power consumption.

[0431] This embodiment can be appropriately combined with other embodiments shown in this specification. [Examples]

[0432] (Synthesis Example 1) In this example, the physical properties and synthesis method of an organic compound according to one embodiment of the present invention will be explained with reference to Figures 16 to 18. Specifically, the physical properties and synthesis method of 5-[4-(10-phenyl-9-antryl)phenyl]-5H-naphtho[2,3-c]carbazole (abbreviated as cNCzPA), shown by structural formula (100) in Embodiment 1, will be explained. The structural formula of cNCzPA is shown below.

[0433] [ka]

[0434] Figure 16 illustrates the absorption and emission spectra of a toluene solution containing cNCzPA.

[0435] Figure 17 illustrates the absorption and emission spectra of a solid thin film of cNCzPA.

[0436] Figures 18(A) and 18(B) are cNCzPA 1 This is a diagram illustrating the 1H NMR spectrum.

[0437] <Method for preparing measuring device and sample> The absorption spectrum of the toluene solution was measured using a UV-Vis spectrophotometer (JASCO Corporation, Model V550), and the absorption spectrum originating from toluene was subtracted.

[0438] The absorption spectra of the solid thin-film samples were measured using a UV-Vis spectrophotometer (JASCO Corporation, Model V550), and the absorption spectra originating from the quartz substrate were subtracted. The thin-film solid samples were formed on a quartz substrate using vacuum deposition.

[0439] The emission spectrum was measured using a fluorometer (FS920, Hamamatsu Photonics Ltd.).

[0440] The following describes a method for calculating the HOMO and LUMO levels of organic compounds based on cyclic voltammetry (CV) measurements.

[0441] An electrochemical analyzer (manufactured by BAS Corporation, model number: ALS Model 600A or 600C) was used as the measuring device.

[0442] For the CV measurement, the solution was prepared by dissolving anhydrous dimethylformamide (DMF) (Aldrich Co., Ltd., 99.8%, catalog number: 22705-6) as the solvent, dissolving tetra-n-butylammonium perchlorate (n-Bu4NClO4) (Tokyo Chemical Industries, Ltd., catalog number: T0836) as the supporting electrolyte to a concentration of 100 mmol / L, and then dissolving the target substance to a concentration of 2 mmol / L.

[0443] Furthermore, a platinum electrode (PTE platinum electrode manufactured by BAS Corporation) was used as the working electrode, a platinum electrode (Pt counter electrode for VC-3 (5cm) manufactured by BAS Corporation) was used as the auxiliary electrode, and Ag / Ag was used as the reference electrode. + Each electrode (RE7 non-aqueous solvent reference electrode, manufactured by BAS Corporation) was used.

[0444] The measurements were performed at room temperature (20 to 25°C). The scan speed during CV measurements was standardized to 0.1 V / sec, and the oxidation potential Ea [V] and reduction potential Ec [V] relative to the reference electrode were measured. Ea was defined as the midpoint potential of the oxidation-reduction wave, and Ec as the midpoint potential of the reduction-oxidation wave.

[0445] Here, since the potential energy of the reference electrode used in this embodiment with respect to the vacuum level is known to be -4.94 [eV], the HOMO level [eV] = -4.94 - Ea and the LUMO level [eV] = -4.94 - Ec can be used to determine the HOMO level and the LUMO level, respectively.

[0446] Furthermore, CV measurements were repeated 100 times, and the oxidation-reduction wave at the 100th cycle was compared with the oxidation-reduction wave at the 1st cycle to investigate the electrical stability of the compound.

[0447] <Physical properties> The absorption spectrum of a toluene solution containing cNCzPA showed absorption peaks around wavelengths of 425 nm, 397 nm, 374 nm, 356 nm, 323 nm, and 310 nm (see Figure 16). The emission spectrum also showed peaks at wavelengths of 432 nm and 458 nm. Light with a wavelength of 397 nm was used as excitation light.

[0448] The absorption spectrum of the solid thin film cNCzPA had peaks around wavelengths of 432 nm, 404 nm, 381 nm, 362 nm, 343 nm, 326 nm, and 314 nm (see Figure 17). The emission spectrum had peaks around wavelengths of 453 nm, 480 nm, and 504 nm. Light with a wavelength of 400 nm was used as excitation light. Note that in the region of wavelengths longer than approximately 450 nm, the intensity of the absorption spectrum of the solid thin film sample includes intensity due to reflection from the substrate. Similarly, in the region of shorter wavelengths, intensity due to reflection from the substrate is also included.

[0449] From the measurement of the oxidation potential Ea [V], it was found that the HOMO level of cNCzPA is -5.56 eV. On the other hand, from the measurement of the reduction potential Ec [V], it was found that the LUMO level of cNCzPA is -2.72 eV.

[0450] Furthermore, when comparing the waveforms after the first cycle and 100th cycle in repeated oxidation-reduction wave measurements, the peak intensity was maintained at 95% for Ea measurements and 89% for Ec measurements.

[0451] This revealed that cNCzPA has high light transmittance in the visible light range. Furthermore, the emission spectrum of the solid thin film showed that it is suitable as a host material for materials that emit fluorescence at wavelengths longer than blue light. In addition, the cNCzPA thin film was found to have good film quality, being less prone to aggregation and showing little change in morphology even in the atmosphere. Moreover, it was confirmed that cNCzPA has very good resistance to oxidation and reduction.

[0452] <Synthesis method> The synthesis method for cNCzPA is described below. The synthesis scheme (SC1) is shown below.

[0453] [ka]

[0454] 0.79 g (3.0 mmol) of 5H-naphtho[2,3-c]carbazole, 1.2 g (3.0 mmol) of 9-(4-bromophenyl)-10-phenylanthracene, 0.20 g (1.1 mmol) of copper(I) iodide, 0.34 g (1.3 mmol) of 18-crown-6-ether, 0.75 g (5.4 mmol) of potassium carbonate, and 2 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone were added to a 50 mL three-necked flask. This mixture was stirred at 180 °C for 24 hours under a nitrogen stream.

[0455] After stirring, the mixture was cooled to 100°C and toluene was added. The organic layer was washed with water, saturated sodium bicarbonate aqueous solution, and saturated brine, and the organic layer was dried over magnesium sulfate. The mixture was filtered naturally, and the filtrate was concentrated to obtain an oily substance.

[0456] The resulting oily substance was purified by silica gel column chromatography (toluene:hexane = 1:4) and then recrystallized with toluene to obtain the target product as a pale yellow powder in a yield of 1.2 g and 68%.

[0457] 1.2 g of the obtained 5-[4-(10-phenyl-9-anthryl)phenyl]-5H-naphtho[2,3-c]carbazole powder was purified by sublimation using the train sublimation method. Sublimation purification was performed by heating 5-[4-(10-phenyl-9-anthryl)phenyl]-5H-naphtho[2,3-c]carbazole at 310°C for 17 hours under conditions of a pressure of 3.5 Pa and an argon flow rate of 5.0 mL / min. After sublimation purification, 1.1 g of pale yellow 5-[4-(10-phenyl-9-anthryl)phenyl]-5H-naphtho[2,3-c]carbazole powder was obtained in a yield of 91%.

[0458] [ 1 [H NMR] The deuterated chloroform solution of the obtained compound 1 The 1H NMR spectra are shown in Figures 18(A) and 18(B). Numerical data are also shown below. This shows that 5-[4-(10-phenyl-9-antryl)phenyl]-5H-naphtho[2,3-c]carbazole was obtained in this synthesis example. 1 H NMR(CDCl3,300MHz):δ=7.38-7.67(m,13H),7.75-7.90(m,10H),8.08-8.12 (m,2H),8.25(d,J=7.8Hz,1H),8.63(s,1H),8.87-8.90(m,1H),9.37(s,1H).

[0459] (Synthesis Example 2) In this example, the physical properties and synthesis method of an organic compound according to one embodiment of the present invention will be explained with reference to Figures 19 to 21. Specifically, the physical properties and synthesis method of 3-[4-(10-phenyl-9-anthryl)phenyl]-3H-benzo[c]naphtho[2,3-g]carbazole (abbreviated as cgBNCzPA), shown by structural formula (119) in Embodiment 1, will be explained. The structural formula of cgBNCzPA is shown below.

[0460] [ka]

[0461] Figure 19 illustrates the absorption and emission spectra of a toluene solution containing cgBNCzPA.

[0462] Figure 20 illustrates the absorption and emission spectra of cgBNCzPA in solid thin film form.

[0463] Figures 21(A) and 21(B) show the cgBNCzPA 1 This is a diagram illustrating the 1H NMR spectrum.

[0464] <Method for preparing measuring device and sample> The absorption spectrum of the toluene solution was measured using a UV-Vis spectrophotometer (JASCO Corporation, Model V550), and the absorption spectrum originating from toluene was subtracted.

[0465] The absorption spectrum of the solid thin-film sample was measured using a spectrophotometer (Hitachi High-Technologies Corporation, Spectrophotometer U4100), and the absorption spectrum and reflectance originating from the quartz substrate were subtracted. The thin-film solid sample was formed on a quartz substrate using vacuum deposition.

[0466] The emission spectrum was measured using a fluorometer (FS920, Hamamatsu Photonics Ltd.).

[0467] The HOMO and LUMO levels of organic compounds were calculated based on cyclic voltammetry (CV) measurements.

[0468] <Physical properties> The absorption spectrum of a toluene solution containing cgBNCzPA showed absorption peaks around wavelengths of 421 nm, 397 nm, 376 nm, and 350 nm (see Figure 19). The emission spectrum also showed peaks at wavelengths of 430 nm, 456 nm, and 484 nm. Light at a wavelength of 397 nm was used as excitation light.

[0469] The absorption spectrum of the solid thin film cgBNCzPA showed peaks around wavelengths of 430 nm, 403 nm, 380 nm, 353 nm, 336 nm, and 302 nm (see Figure 20). The emission spectrum also showed peaks around wavelengths of 487 nm and 680 nm. Light with a wavelength of 400 nm was used as excitation light.

[0470] From the measurement of the oxidation potential Ea [V], it was found that the HOMO level of cgBNCzPA is -5.56 eV. On the other hand, from the measurement of the reduction potential Ec [V], it was found that the LUMO level of cgBNCzPA is -2.73 eV.

[0471] Furthermore, when comparing the waveform after the first cycle with the waveform after 100 cycles in repeated oxidation-reduction wave measurements, the peak intensity was maintained at 92% in the Ea measurement.

[0472] This revealed that cgBNCzPA has high light transmittance in the visible light range. Furthermore, the emission spectrum of the solid thin film showed that it is suitable as a host material for materials that emit fluorescence at wavelengths longer than blue light. In addition, the cgBNCzPA thin film was found to have good film quality, being less prone to aggregation and showing little change in morphology even under atmospheric conditions. Moreover, it was confirmed that cgBNCzPA has very good resistance to oxidation.

[0473] <Synthesis method> The synthesis method for cgBNCzPA is described below. Synthesis schemes (SC2) to (SC4) are shown below.

[0474] Step 1: Synthesis of 1-(2-nitro-1-naphthyl)anthracene 2.5 g (7.7 mmol) of 2-nitro-1-triflatonaphthalene, 2.5 g (8.3 mmol) of 2-(1-anthryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 1.6 g (15 mmol) of sodium carbonate, and 70 mL of toluene were added to a 200 mL three-necked flask. The mixture was degassed by stirring under reduced pressure, and the flask was purged with nitrogen. 0.56 g (0.48 mmol) of tetrakis(triphenylphosphine)palladium(0) was added to the mixture, and the mixture was stirred at 130°C for 17 hours under a nitrogen stream.

[0475] After stirring, water was added to the resulting mixture, and the aqueous layer was extracted with toluene. The resulting extract and the organic layer were combined, washed with saturated brine, and the organic layer was dried over magnesium sulfate.

[0476] The resulting mixture was filtered by gravity, and the filtrate was concentrated to obtain an oily substance. The toluene solution of the obtained oily substance was filtered by suction through Celite and alumina, and the filtrate was concentrated to obtain an oily substance. This oily substance was purified by silica gel column chromatography (toluene:hexane = 1:1) to obtain 1.7 g of the target product as a pale yellow solid in a yield of 61%.

[0477] [ka]

[0478] Step 2: Synthesis of 3H-benzo[c]naphtho[2,3-g]carbazole In a 100 mL three-necked flask, 1.8 g (5.1 mmol) of 1-(2-nitro-1-naphthyl)anthracene synthesized in step 1 above, 5.5 g (21 mmol) of triphenylphosphine, and 40 mL of 1,2-dichlorobenzene were added. This solution was stirred at 180 °C for 20 hours under a nitrogen stream.

[0479] After stirring, water was added to the resulting solution, and the aqueous layer was extracted with toluene. The resulting extract and the organic layer were combined, washed with saturated brine, and the organic layer was dried over magnesium sulfate.

[0480] The resulting mixture was filtered by gravity, and the filtrate was concentrated to obtain an oily substance. The obtained oily substance was purified by silica gel column chromatography (hexane:toluene = 1:2) to obtain another oily substance. Hexane was added to the obtained oily substance, and ultrasonic waves were applied. The precipitated solid was collected by suction filtration, yielding the target yellow powder in a yield of 1.3 g and 78%.

[0481] [ka]

[0482] Step 3: Synthesis of 3-[4-(10-phenyl-9-anthryl)phenyl]-3H-benzo[c]naphtho[2,3-g]carbazole 1.0 g (2.5 mmol) of 9-(4-bromophenyl)-10-phenylanthracene, 0.79 g (2.5 mmol) of 3H-benzo[c]naphtho[2,3-g]carbazole synthesized in step 2 above, 0.52 g (3.8 mmol) of potassium carbonate, 0.26 g (1.0 mmol) of 18-crown-6-ether, 4 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU), and 0.13 g (0.67 mmol) of copper(I) iodide were added to a 50 mL three-necked flask. This mixture was stirred at 180 °C under a nitrogen stream for 28 hours.

[0483] After stirring, the mixture was cooled to 80°C, water was added, and the aqueous layer was extracted with toluene. The resulting extract was washed with saturated brine, and the organic layer was dried over magnesium sulfate.

[0484] The resulting mixture was filtered naturally, and the filtrate was concentrated to obtain an oily substance. This oily substance was purified by silica gel column chromatography (toluene:hexane = 1:3), and then recrystallized with toluene / hexane to obtain the target yellow powder in a yield of 0.79 g and 49%.

[0485] [ka]

[0486] 0.75 g of the obtained 3-[4-(10-phenyl-9-anthryl)phenyl]-3H-benzo[c]naphtho[2,3-g]carbazole powder was purified by sublimation using the train sublimation method. Sublimation purification was performed by heating 3-[4-(10-phenyl-9-anthryl)phenyl]-3H-benzo[c]naphtho[2,3-g]carbazole at 350°C for 17 hours under conditions of a pressure of 3.5 Pa and an argon flow rate of 15 mL / min. After sublimation purification, 0.62 g of pale yellow powder of 3-[4-(10-phenyl-9-anthryl)phenyl]-3H-benzo[c]naphtho[2,3-g]carbazole was obtained in a yield of 83%.

[0487] [ 1 [H NMR] The deuterated chloroform solution of the obtained compound 1 The 1H NMR spectra are shown in Figures 21(A) and 21(B). Numerical data is also shown below. This confirms that cgBNCzPA was obtained in this synthesis example. 1 H NMR(CDCl3,300MHz):δ=7.39-7.65(m,12H),7.76-7.90(m,11H),7.96(d,J=9.0Hz,1H),8 .06-8.15(m,3H),8.21(d,J=7.8Hz,1H),8.65(s,1H),9.51(d,J=8.4Hz,1H),9.86(s,1H).

[0488] (Synthesis Example 3) In this example, the physical properties and synthesis method of an organic compound according to one embodiment of the present invention will be explained with reference to Figures 22 to 24. Specifically, the physical properties and synthesis method of 9-[4-(carbazole-9-yl)phenyl]-5-phenylnaphtho[2,3-c]carbazole (abbreviated as 9CzPPcNC), shown by structural formula (135) in Embodiment 1, will be explained. The structural formula of 9CzPPcNC is shown below.

[0489] [ka]

[0490] Figure 22 illustrates the absorption and emission spectra of a toluene solution containing 9CzPPcNC.

[0491] Figure 23 illustrates the absorption and emission spectra of 9CzPPcNC in solid thin film form.

[0492] Figures 24(A) and 24(B) show the 9CzPPcNC 1 This is a diagram illustrating the 1H NMR spectrum.

[0493] <Method for preparing measuring device and sample> The absorption spectrum of the toluene solution was measured using a UV-Vis spectrophotometer (JASCO Corporation, Model V550), and the absorption spectrum originating from toluene was subtracted.

[0494] The absorption spectra of the solid thin-film samples were measured using a UV-Vis spectrophotometer (JASCO Corporation, Model V550), and the absorption spectra originating from the quartz substrate were subtracted. The thin-film solid samples were formed on a quartz substrate using vacuum deposition.

[0495] The emission spectrum was measured using a fluorometer (FS920, Hamamatsu Photonics Ltd.).

[0496] The HOMO and LUMO levels of organic compounds were calculated based on cyclic voltammetry (CV) measurements.

[0497] <Physical properties> The absorption spectrum of a toluene solution containing 9CzPPcNC showed absorption peaks around wavelengths of 430 nm, 407 nm, 378 nm, 359 nm, 327 nm, and 313 nm (see Figure 22). The emission spectrum also showed peaks at wavelengths of 440 nm, 467 nm, and 498 nm. Light with a wavelength of 408 nm was used as excitation light.

[0498] The absorption spectrum of the solid thin film 9CzPPcNC had peaks around wavelengths of 438 nm, 414 nm, 384 nm, 364 nm, 347 nm, 330 nm, and 317 nm (see Figure 23). The emission spectrum had a peak around wavelength 545 nm. Light with a wavelength of 414 nm was used as the excitation light. Note that in the region of wavelengths longer than approximately 450 nm, the intensity of the absorption spectrum of the solid thin film sample includes intensity due to reflection from the substrate. Similarly, in the region of shorter wavelengths, intensity due to reflection from the substrate is also included.

[0499] From the measurement of the oxidation potential Ea [V], it was found that the HOMO level of 9CzPPcNC is -5.58 eV. On the other hand, from the measurement of the reduction potential Ec [V], it was found that the LUMO level of 9CzPPcNC is -2.69 eV.

[0500] Furthermore, the emission spectrum of the solid thin film revealed that it is suitable as a host material for materials that emit green fluorescence and longer wavelength fluorescence. The 9CzPPcNC thin film was found to have good film quality, being less prone to aggregation and showing little change in morphology even under atmospheric conditions.

[0501] <Synthesis method> The synthesis method for 9CzPPcNC is described below. Synthesis schemes (SC5) to (SC9) are shown below.

[0502] Step 1: Synthesis of 2-(5-[4-(carbazole-9-yl)phenyl]-1-anthryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2.5 g (8.7 mmol) of 4-(carbazole-9-yl)phenylboronic acid, 3.1 g (9.3 mmol) of 1,5-dibromoanthracene, 0.27 g (0.89 mmol) of tris(2-methylphenyl)phosphine, 2.5 g (18 mmol) of potassium carbonate, 85 mL of toluene, 9 mL of ethanol, and 9 mL of water were added to a 200 mL three-necked flask. The mixture was degassed by stirring under reduced pressure, and the flask was purged with nitrogen. 44 mg (0.20 mmol) of palladium(II) acetate was added to the mixture, and it was stirred at 80°C for 7 hours under a nitrogen stream.

[0503] After stirring, water and toluene were added to the resulting mixture, and the precipitated solid was removed by suction filtration. The aqueous layer of this mixture was extracted with toluene, and the extract solution and the organic layer were combined, washed with saturated brine, and the organic layer was dried over magnesium sulfate.

[0504] The resulting mixture was subjected to natural filtration, and the filtrate was concentrated to obtain a solid. A toluene solution of the obtained solid was filtered by suction through Celite and alumina, and the filtrate was concentrated to obtain a solid. Methanol was added to this solid, and sonication was irradiated. The precipitated solid was collected to obtain the crude product of the intermediate 9-[4-(5-bromo-1-anthryl)phenyl]carbazole. The above synthesis scheme is shown below.

[0505] [ka]

[0506] Next, 3.2 g (6.5 mmol) of crude 9-[4-(5-bromo-1-anthryl)phenyl]carbazole, 3.2 g (13 mmol) of bis(pinacolate)diborone, 3.0 g (31 mmol) of potassium acetate, and 40 mL of 1,4-dioxane were added to a 200 mL three-necked flask. This mixture was degassed by stirring under reduced pressure, and the flask was purged with nitrogen. To this mixture, 0.17 g (0.21 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride-dichloromethane complex was added, and the mixture was stirred at 80°C for 3 hours under a nitrogen stream.

[0507] After stirring, water was added to the mixture, and the aqueous layer was extracted with toluene. The resulting extract was combined with the organic layer, washed with saturated brine, and the organic layer was dried over magnesium sulfate.

[0508] This mixture was filtered naturally, and the filtrate was concentrated to obtain a solid. The obtained solid was purified by silica gel column chromatography (toluene:hexane = 1:1) to obtain 1.8 g of the target product, a pale yellow oily substance, in a yield of 38%. The synthesis scheme described above is shown below.

[0509] [ka]

[0510] Step 2: Synthesis of 9-{4-[5-(2-nitrophenyl)-1-antryl]phenyl}carbazole In a 200 mL three-necked flask, 1.8 g (3.3 mmol) of 2-(5-[4-(carbazole-9-yl)phenyl]-1-anthryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane synthesized in step 1 above, 0.86 g (4.3 mmol) of 1-bromo-2-nitrobenzene, 0.12 g (0.87 mmol) of tris(2-methylphenyl)phosphine, 0.96 g (6.9 mmol) of potassium carbonate, 35 mL of toluene, 3.5 mL of ethanol, and 3.5 mL of water were added. This mixture was degassed by stirring under reduced pressure, and the flask was purged with nitrogen. 28 mg (93 μmol) of palladium(II) acetate was added to this mixture, and the mixture was stirred at 80°C for 7 hours under a nitrogen stream.

[0511] After stirring, water was added to the resulting mixture, and the aqueous layer was extracted with toluene. The resulting extract and the organic layer were combined, washed with saturated brine, and the organic layer was dried over magnesium sulfate.

[0512] The resulting mixture was subjected to natural filtration, and the filtrate was concentrated to obtain an oily substance. A toluene solution of the obtained oily substance was filtered by suction through Celite and alumina, and the filtrate was concentrated to obtain an oily substance. Hexane / ethanol was added to this oily substance, and ultrasonic waves were applied. The precipitated solid was collected, yielding 1.4 g of the target solid in a yield of 76%. The synthesis scheme for Step 2 is shown below.

[0513] [ka]

[0514] Step 3: Synthesis of 9-[4-(carbazole-9-yl)phenyl]naphtho[2,3-c]carbazole In a 200 mL three-necked flask, 1.4 g (2.5 mmol) of 9-{4-[5-(2-nitrophenyl)-1-anthryl]phenyl}carbazole synthesized in step 2 above, 1.4 g (5.3 mmol) of triphenylphosphine, and 30 mL of 1,2-dichlorobenzene were added. This solution was stirred at 180 °C for 27 hours under a nitrogen stream.

[0515] After stirring, the solvent was removed under reduced pressure. The resulting solid was purified by silica gel column chromatography (hexane:toluene = 1:1) to obtain the target yellow powder in a yield of 0.47 g and 37%. The synthesis scheme for Step 3 is shown below.

[0516] [ka]

[0517] Step 4: Synthesis of 9-[4-(carbazole-9-yl)phenyl]-5-phenylnaphtho[2,3-c]carbazole In a 50 mL three-necked flask, 0.94 g (1.8 mmol) of 9-[4-(carbazole-9-yl)phenyl]naphtho[2,3-c]carbazole synthesized in step 3 above, 0.67 g (3.3 mmol) of iodobenzene, 85 mg (0.45 mmol) of copper(I) iodide, 0.34 g (0.75 mmol) of 18-crown-6-ether, 1.1 g (8.2 mmol) of potassium carbonate, and 7 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone were added. This mixture was stirred at 180 °C for 22 hours under a nitrogen stream.

[0518] After stirring, the mixture was allowed to cool to room temperature and water was added. The aqueous layer of this mixture was extracted with toluene, the extract was washed with saturated brine, and dried over magnesium sulfate. The mixture was then filtered naturally, and the filtrate was concentrated to obtain an oily substance.

[0519] The obtained oily product was purified by silica gel column chromatography (toluene:hexane = 1:2), and further recrystallized from toluene / ethyl acetate, to give 0.84 g of the target product as a pale yellow powder in a yield of 78%. The synthesis scheme of step 4 is shown below.

[0520] Chemical formula

[0521] 0.76 g of the obtained 9-[4-(carbazol-9-yl)phenyl]-5-phenylnaphtho[2,3-c]carbazole powder was purified by sublimation via the train sublimation method. Sublimation purification was carried out by heating 9-[4-(carbazol-9-yl)phenyl]-5-phenylnaphtho[2,3-c]carbazole at 290°C for 21 hours under the conditions of a pressure of 4.4 Pa and an argon flow rate of 5.0 mL / min. After sublimation purification, 0.71 g of pale yellow powder of 9-[4-(carbazol-9-yl)phenyl]-5-phenylnaphtho[2,3-c]carbazole was obtained in a yield of 93%.

[0522] 1 H NMR] The ¹H NMR spectrum of the obtained compound in a deuterated chloroform solution is shown in 1 Fig. 24(A) and Fig. 24(B). The numerical data are shown below. This confirmed that 9CzPPcNC was obtained in this synthesis example. 1 ¹H NMR (CDCl₃, 300 MHz): δ = 7.31-7.37 (m, 2H), 7.45-7.71 (m, 15H), 7.78 (d, J = 8.7 Hz, 2H), 7.89 (d, J = 8.7 Hz, 2H), 7.95 (d, J = 9.3 Hz, 1H), 8.20 (d, J = 7.8 Hz, 2H), 8.29 (d, J = 8.4 Hz, 1H), 8.74 (s, 1H), 8.85 (d, J = 8.7 Hz, 1H), 9.42 (s, 1H). EXAMPLES

[0523] ​In this example, a thin film formed using a synthesized organic compound according to one embodiment of the present invention will be described with reference to Figure 25.

[0524] Figure 25 illustrates the wavelength-refractive index and wavelength-attenuation coefficient characteristics of an organic compound formed in a thin film. In this specification, when both ordinary and extraordinary refractive indices are present in the measured material, the ordinary refractive index is used as the index. The vertical axis of Figure 25 represents the refractive index n and the attenuation coefficient k.

[0525] An organic material according to one aspect of the present invention has high light transmittance to 450 nm light. It also has a high refractive index to 450 nm light. As a result, for example, if a thin film of the organic material according to one aspect of the present invention is formed between an electrode on the light extraction side of a light-emitting device and the light-emitting layer, the light from the light-emitting device can be efficiently extracted. Alternatively, a thin film of the organic material according to one aspect of the present invention can be suitably used as a cap layer for a light-emitting device. Or, for example, when an inorganic film is formed as a sealing film (cap layer) on an electrode on the light extraction side of a light-emitting device, forming the organic material according to one aspect of the present invention between the electrode and the inorganic film is preferable because it provides high light extraction efficiency. In this case, since the refractive index of the organic material according to one aspect of the present invention around 450 nm is around 2 (1.9 to 2.1), the inorganic film can be one with a higher refractive index (1.9 to 2.5). For example, silicon oxynitride can be used as the inorganic film. The thickness of the inorganic film is preferably 1 μm or less. Alternatively, the inorganic film and the organic material according to one aspect of the present invention may be repeatedly laminated to form a sealing film (cap layer). Alternatively, a thin film of an organic material according to one embodiment of the present invention has high light transmittance and a high refractive index throughout the visible range, and can be suitably used as a cap layer for a light-emitting device. [Examples]

[0526] In this embodiment, a light-emitting device 1 according to one aspect of the present invention, which was fabricated, will be described with reference to Figures 26 to 32.

[0527] Figure 26 is a diagram illustrating the configuration of a light-emitting device.

[0528] Figure 27 illustrates the current density-luminance characteristics of a light-emitting device.

[0529] Figure 28 illustrates the brightness-current efficiency characteristics of a light-emitting device.

[0530] Figure 29 illustrates the voltage-luminance characteristics of a light-emitting device.

[0531] Figure 30 illustrates the voltage-current characteristics of the light-emitting device.

[0532] Figure 31 illustrates the luminance-external quantum efficiency characteristics of the light-emitting device. The external quantum efficiency was calculated from the luminance and emission spectrum observed from the front of the device, assuming a Lambertsian light distribution pattern.

[0533] Figure 32 shows a light-emitting device with a emission rate of 1000 cd / m². 2 This diagram illustrates the emission spectrum when the light source is emitted at a specific brightness level.

[0534] <Light-emitting device 1> The light-emitting device fabricated in this embodiment has the same configuration as the light-emitting device 150 (see Figure 26).

[0535] The light-emitting device 150 includes an electrode 101, an electrode 102, a layer 111, and a unit 103. Electrode 102 has a region that overlaps with electrode 101.

[0536] Unit 103 includes a region sandwiched between electrodes 101 and 102. The light-emitting device also includes layers 104 and 105. Layer 104 includes a region sandwiched between electrodes 101 and unit 103, and layer 105 includes a region sandwiched between unit 103 and electrode 102.

[0537] Unit 103 comprises layers 111, 112, and 113. Layer 112 includes a region sandwiched between electrode 101 and layer 111.

[0538] Layer 111 comprises a region sandwiched between layers 112 and 113. Layer 111 comprises a region sandwiched between electrodes 101 and 102, and layer 111 contains a luminescent material and a charge transport material CTM.

[0539] Layer 113 comprises a region sandwiched between layer 111 and electrode 102. Layer 113 comprises layer 113A and layer 113B. Layer 113A comprises a region sandwiched between layer 111 and layer 113B, and layer 113A contains a charge transport material CTM.

[0540] The charge transport material CTM is an organic compound according to one embodiment of the present invention. For example, the organic compound described in Embodiment 1 can be used as the charge transport material CTM.

[0541] Configuration of Light-Emitting Device 1 Table 1 shows the configuration of light-emitting device 1. In light-emitting device 1, 5-[4-(10-phenyl-9-antryl)phenyl]-5H-naphtho[2,3-c]carbazole (abbreviated as cNCzPA) was used as the charge transport material CTM.

[0542] Furthermore, the structural formulas of the materials used in the light-emitting device described in this embodiment are shown below (the structural formulas of the materials used in other light-emitting devices are also described below, and their configurations will be explained later).

[0543] [Table 1]

[0544] [ka]

[0545] 《Method for fabricating light-emitting device 1》 The light-emitting device 1 described in this embodiment was fabricated using a method comprising the following steps.

[0546] [Step 1] In the first step, electrode 101 was formed. Specifically, it was formed by sputtering using indium tin oxide (ITSO), which contains silicon or silicon oxide, as the target.

[0547] The electrode 101 contains ITSO and has a thickness of 70 nm. Next, the substrate on which the electrode 101 is formed is washed with water, fired at 200°C for 1 hour, and then subjected to UV ozone treatment for 370 seconds. After that, 10 -4 The substrate was introduced into a vacuum deposition apparatus where the internal pressure was reduced to approximately Pa, and vacuum firing was performed at 170°C for 30 minutes in the heating chamber of the vacuum deposition apparatus. After that, the substrate was allowed to cool for about 30 minutes.

[0548] [Step 2] In the second step, a layer 104 was formed on the electrode 101. Specifically, the material was co-deposited using a resistance heating method.

[0549] Layer 104 contains 9-[4-(9-phenyl-9H-carbazole-3-yl)-phenyl]phenanthrene (abbreviated as PCPPn) and molybdenum oxide (abbreviated as MoOx) in a PCPPn:MoOx ratio of 4:2 (by weight), and has a thickness of 10 nm.

[0550] [Step 3] In the third step, layer 112 was formed on layer 104. Specifically, the material was deposited using a resistance heating method.

[0551] Layer 112 contains PCPPn and has a thickness of 30 nm.

[0552] [Step 4] In the fourth step, layer 111 was formed on layer 112. Specifically, the material was co-deposited using a resistance heating method.

[0553] Layer 111 contains cNCzPA and N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-anthracene-9,10-diamine (abbreviated as 9,10mMemFLPA2A) in a ratio of cNCzPA:9,10mMemFLPA2A = 1:0.1 (by weight) and has a thickness of 25 nm.

[0554] [Step 5] In the fifth step, layer 113A was formed on layer 111. Specifically, the material was deposited using a resistance heating method.

[0555] Layer 113A contains cNCzPA and has a thickness of 10 nm.

[0556] [Step 6] In the sixth step, layer 113B was formed on layer 113A. Specifically, the material was deposited using a resistance heating method.

[0557] Layer 113B contains bathophenanthroline (abbreviated as Bphen) and has a thickness of 15 nm.

[0558] [Step 7] In the seventh step, layer 105 was formed on layer 113B. Specifically, the material was deposited using a resistance heating method.

[0559] Layer 105 contains lithium fluoride (abbreviated as LiF) and has a thickness of 1 nm.

[0560] [Step 8] In the eighth step, an electrode 102 was formed on layer 105. Specifically, the material was deposited using a resistance heating method.

[0561] Electrode 102 contains Al and has a thickness of 200 nm.

[0562] Operating characteristics of the light-emitting device 1 When power was supplied, the light-emitting device 1 emitted light EL1 (see Figure 26). The operating characteristics of the light-emitting device 1 were measured (see Figures 27 to 32). The measurements were performed at room temperature.

[0563] Light-emitting device 1 has a brightness of 1000 cd / m². 2 Table 2 shows the main initial characteristics when the device is illuminated to a certain degree. (Note that the initial characteristics of other light-emitting devices are also described in Table 2, and their configurations will be described later.) Also, in the table of this embodiment, subscripts and superscripts are written in standard size for convenience. For example, subscripts used in abbreviations and superscripts used in units are written in standard size in the table. These descriptions in the table can be interpreted in reference to the description in the specification.

[0564] [Table 2]

[0565] Light-emitting device 1 has a light emission of 5000 cd / m² compared to comparative light-emitting device 1. 2 High efficiency was observed in the high-brightness region. For example, light-emitting elements for outdoor use or light-emitting elements for display devices used in augmented reality (AR) require high brightness and high efficiency per unit of light-emitting area. This light-emitting device 1 is suitable for such devices. Furthermore, it was found that light-emitting device 1 has a higher current value than comparative light-emitting device 1 in the region of 3V or less (see Figure 30). In addition, cNCzPA could be used as the host material for the light-emitting layer of the light-emitting device. Furthermore, cNCzPA could be suitably used as the host material with a green fluorescent light-emitting material as the guest material.

[0566] Furthermore, cNCzPA and cgBNCzPA contain anthryl groups as substituents, resulting in high carrier transport properties. This allowed for a lower driving voltage for the light-emitting device.

[0567] (Reference example 1) Table 1 shows the configuration of comparative light-emitting device 1. In comparative light-emitting device 1, 7-[4-(10-phenyl-9-antryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) was used as the charge transport material CTM.

[0568] The comparative light-emitting device 1 described in this embodiment differs from light-emitting device 1 in that the charge transport material CTM used in layers 111 and 113A is different. Specifically, it differs from light-emitting device 1 in that cgDBCzPA is used instead of cNCzPA.

[0569] 《Method for fabricating comparative light-emitting device 1》 A comparative light-emitting device 1 was fabricated using a method comprising the following steps.

[0570] Note that the fabrication method for comparative light-emitting device 1 differs from that of light-emitting device 1 in that cgDBCzPA is used instead of cNCzPA in the step of forming layer 111, and cgDBCzPA is used instead of cNCzPA in the step of forming layer 113A. Here, the differences will be explained in detail, and the above explanation will be used as a reference for parts where the same method is used.

[0571] [Step 4] In the fourth step, layer 111 was formed on layer 112. Specifically, the material was co-deposited using a resistance heating method.

[0572] Layer 111 contains cgDBCzPA and 9,10mMemFLPA2A in a weight ratio of cgDBCzPA:9,10mMemFLPA2A=1:0.1 and has a thickness of 25nm.

[0573] [Step 5] In the fifth step, layer 113A was formed on layer 111. Specifically, the material was deposited using a resistance heating method.

[0574] Layer 113A contains cgDBCzPA and has a thickness of 10 nm.

[0575] Table 2 shows the main initial characteristics of comparative light-emitting device 1. [Examples]

[0576] In this embodiment, one embodiment of the present invention, light-emitting devices 2 to 4, will be described with reference to Figures 26 and 33 to 38.

[0577] Figure 33 illustrates the current density-luminance characteristics of a light-emitting device.

[0578] Figure 34 illustrates the brightness-current efficiency characteristics of a light-emitting device.

[0579] Figure 35 illustrates the voltage-luminance characteristics of a light-emitting device.

[0580] Figure 36 illustrates the voltage-current characteristics of a light-emitting device.

[0581] Figure 37 illustrates the luminance-external quantum efficiency characteristics of the light-emitting device. The external quantum efficiency was calculated from the luminance and emission spectrum observed from the front of the device, assuming a Lambertsian light distribution pattern.

[0582] Figure 38 shows a light-emitting device with a emission rate of 1000 cd / m². 2 This diagram illustrates the emission spectrum when the light source is emitted at a specific brightness level.

[0583] <Light-emitting device 2> The light-emitting device fabricated in this embodiment has the same configuration as the light-emitting device 150 (see Figure 26).

[0584] Configuration of Light-Emitting Device 2 Table 3 shows the configuration of light-emitting device 2. In light-emitting device 2, cNCzPA was used as the charge transport material CTM.

[0585] Furthermore, the light-emitting device 2 fabricated in this embodiment differs from light-emitting device 1 in the configuration of layers 112 and 111. Specifically, a layer 112 with a thickness of 20 nm was used instead of a layer 112 with a thickness of 30 nm.

[0586] Furthermore, in layer 111, N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviated as 1,6mMemFLPAPrn) was used instead of 9,10mMemFLPA2A.

[0587] [Table 3]

[0588] 《Method for fabricating light-emitting device 2》 Light-emitting device 2 was fabricated using a method comprising the following steps.

[0589] The fabrication method for light-emitting device 2 differs from that of light-emitting device 1 in that, in the step of forming layer 112, a layer 112 with a thickness of 20 nm is formed instead of a layer 112 with a thickness of 30 nm, and in the step of forming layer 111, 1,6 nmem FLPAPrn is used instead of 9,10 nmem FLP2A. Here, the differences will be explained in detail, and the above explanation will be used as a reference for parts where the same method is used.

[0590] [Step 3] In the third step, layer 112 was formed on layer 104. Specifically, the material was deposited using a resistance heating method.

[0591] Layer 112 contains PCPPn and has a thickness of 20 nm.

[0592] [Step 4] In the fourth step, layer 111 was formed on layer 112. Specifically, the material was co-deposited using a resistance heating method.

[0593] Note that the layer 111 contains cNCzPA and 1,6mMemFLPAPrn at a weight ratio of cNCzPA:1,6mMemFLPAPrn = 1:0.15, and has a thickness of 25 nm.

[0594] Operating Characteristics of Light-Emitting Device 2 When power is supplied, Light-Emitting Device 2 emits light EL1 (see FIG. 26). The operating characteristics of Light-Emitting Device 2 were measured (see FIGS. 33 to 38). Note that the measurement was performed at room temperature.

[0595] When Light-Emitting Device 2 was caused to emit light at approximately a luminance of 1000 cd / m 2 , main initial characteristics are shown in Table 2.

[0596] In an element using cNCzPA as a host material for a light-emitting layer of a light-emitting device, approximately a luminance of 1000 cd / m 2 could be achieved at a low voltage of 3.0 V. The external quantum efficiency is 8.6%, which is extremely high, indicating that cNCzPA is an optimal host material for causing a blue fluorescent light-emitting substance to emit light as a guest material.

[0597] The organic compound according to one embodiment of the present invention can be used as a host material for a light-emitting layer of a light-emitting device. Furthermore, it can be used as a host material when a blue fluorescent light-emitting substance is used as a guest material. Additionally, it can cause a blue fluorescent light-emitting substance to emit light with high efficiency.

[0598] <Light-Emitting Device 3> The light-emitting device manufactured described in this example has the same structure as that of the light-emitting device 150 (see FIG. 26).

[0599] Structure of Light-Emitting Device 3 The structure of Light-Emitting Device 3 is shown in Table 3. Note that in Light-Emitting Device 3, 3-[4-(10-phenyl-9-anthryl)phenyl]-3H-benzo[c]naphtho[2,3-g]carbazole (abbreviation: cgBNCzPA) was used as the charge transport material CTM.

[0600] The light-emitting device 3 fabricated in this embodiment differs from light-emitting device 1 in the configuration of layers 111 and 113A. Specifically, in layer 111, cgBNCzPA is used instead of cNCzPA, and 1,6mMemFLPAPrn is used instead of 9,10mMemFLPA2A, and in layer 113A, cgBNCzPA is used instead of cNCzPA.

[0601] 《Method for fabricating light-emitting device 3》 Light-emitting device 3 was fabricated using a method comprising the following steps.

[0602] The method for fabricating light-emitting device 3 differs from the method for fabricating light-emitting device 1 in that, in the step of forming layer 111, cgBNCzPA is used instead of cNCzPA, and 1,6mMemFLPAPrn is used instead of 9,10mMemFLPA2A, and in the step of forming layer 113A, cgBNCzPA is used instead of cNCzPA. Here, the differences will be explained in detail, and the above explanation will be used as a reference for parts where the same method is used.

[0603] [Step 4] In the fourth step, layer 111 was formed on layer 112. Specifically, the material was co-deposited using a resistance heating method.

[0604] Layer 111 contains cgBNCzPA and 1,6mMemFLPAPrn in a weight ratio of cgBNCzPA:1,6mMemFLPAPrn = 1:0.15 and has a thickness of 25 nm.

[0605] [Step 5] In the fifth step, layer 113A was formed on layer 111. Specifically, the material was deposited using a resistance heating method.

[0606] Layer 113A contains cgBNCzPA and has a thickness of 10 nm.

[0607] Operating characteristics of the light-emitting device 3 When power was supplied, the light-emitting device 3 emitted light EL1 (see Figure 26). The operating characteristics of the light-emitting device 3 were measured (see Figures 33 to 38). The measurements were performed at room temperature.

[0608] Light-emitting device 3 with a brightness of 1000 cd / m² 2 Table 2 shows the main initial characteristics when the light is emitted to a certain degree.

[0609] In devices using cgBNCzPA as the host material for the light-emitting layer of a light-emitting device, the brightness is 1000 cd / m². 2 We were able to induce light emission at a low voltage of 3.1V. Furthermore, it is possible to provide a highly efficient fluorescent light-emitting element with an external quantum efficiency of 5.6%.

[0610] An organic compound according to one aspect of the present invention can be used as a host material for the light-emitting layer of a light-emitting device. Furthermore, a blue fluorescent material can be used as a guest material in the host material. Additionally, the blue fluorescent material can be made to emit light with high efficiency.

[0611] <Light-emitting device 4> The light-emitting device fabricated in this embodiment has the same configuration as the light-emitting device 150 (see Figure 26).

[0612] Configuration of Light-Emitting Device 4 Table 3 shows the configuration of the light-emitting device 4. In light-emitting device 4, 9-[4-(carbazole-9-yl)phenyl]-5-phenylnaphtho[2,3-c]carbazole (abbreviation: 9CzPPcNC) was used as the charge transport material CTM.

[0613] The light-emitting device 4 fabricated in this embodiment differs from light-emitting device 1 in the configuration of layers 111 and 113A. Specifically, in layer 111, 9CzPPcNC is used instead of cNCzPA, and 1,6mMemFLPAPrn is used instead of 9,10mMemFLPA2A, and in layer 113A, 9CzPPcNC is used instead of cNCzPA.

[0614] 《Method for fabricating light-emitting device 4》 A light-emitting device 4 was fabricated using a method comprising the following steps.

[0615] The method for fabricating the light-emitting device 4 differs from the method for fabricating the light-emitting device 1 in that, in the step of forming layer 111, 9CzPPcNC is used instead of cNCzPA, and 1,6mMemFLPAPrn is used instead of 9,10mMemFLPA2A, and in the step of forming layer 113A, 9CzPPcNC is used instead of cNCzPA. Here, the differences will be explained in detail, and the above explanation will be used as a reference for parts where the same method is used.

[0616] [Step 4] In the fourth step, layer 111 was formed on layer 112. Specifically, the material was co-deposited using a resistance heating method.

[0617] Layer 111 contains 9CzPPcNC and 1,6mMemFLPAPrn in a weight ratio of 9CzPPcNC:1,6mMemFLPAPrn = 1:0.15 and has a thickness of 25nm.

[0618] [Step 5] In the fifth step, layer 113A was formed on layer 111. Specifically, the material was deposited using a resistance heating method.

[0619] Layer 113A contains 9CzPPcNC and has a thickness of 10 nm.

[0620] Operating characteristics of the light-emitting device 4 When power was supplied, the light-emitting device 4 emitted light EL1 (see Figure 26). The operating characteristics of the light-emitting device 4 were measured (see Figures 33 to 38). The measurements were performed at room temperature.

[0621] Light-emitting device 4 with a brightness of 1000 cd / m² 2 Table 2 shows the main initial characteristics when the light is emitted to a certain degree.

[0622] In devices using 9CzPPcNC as the host material for the light-emitting layer of a light-emitting device, it is possible to provide a highly efficient fluorescent light-emitting element with an external quantum efficiency of 5.4%.

[0623] An organic compound according to one aspect of the present invention can be used as a host material for the light-emitting layer of a light-emitting device. Furthermore, a blue fluorescent material can be used as a guest material with the organic compound according to one aspect of the present invention as the host material. In addition, a blue fluorescent material can be made to emit light with high efficiency with the organic compound according to one aspect of the present invention as the host material. [Explanation of symbols]

[0624] 101 Electrode 101S electrode 102 electrode 103 units 103S Unit 104 layers 105 layers 106 Middle layer 106A layer 106B layer 111 layers 112 layers 113 layers 113A layer 113B layer 114 layers 114N layer 114P layer 150 Light-Emitting Devices 170 Optical Functional Devices 400 circuit boards 401 Electrode 403 EL layer 404 Electrode 405 sealant 406 Sealant 407 Sealing substrate 412 pads 420 IC chips 601 Source Line Drive Circuit 602 pixel section 603 Gate wire drive circuit 604 Sealing substrate 605 Sealant 607 Space 608 Wiring 610 element substrate 611 Switching FET 612 Current-Controlled FET 613 Electrode 614 Insulators 616 EL layer 617 Electrode 618 Light-emitting devices 623 FET 700 Function Panel 951 circuit board 952 Electrode 953 Insulating layer 954 Partition layer 955 EL layer 956 Electrode 1001 circuit board 1002 Underlying insulating film 1003 Gate Insulator 10:06 Guard Station 1007 🙏 1008 Gate 1020 Interlayer insulating film 1021 Interlayer insulating film 1022 Electrode 1024B Electrode 1024G electrode 1024R electrode 1024W electrode 1025 Bulkhead 1028 EL layer 1029 Electrode 1031 Sealing substrate 1032 Sealant 1033 Base material 1034B Colored layer 1034G colored layer 1034R colored layer 1035 Black Matrix 1036 Overcoat layer 1037 Interlayer insulating film 1040 pixel section 1041 Drive circuit section 1042 Peripheral area 2001 cabinet 2002 light source 2100 Robots 2101 Illuminance Sensor 2102 Microphone 2103 Top Camera 2104 Speaker 2105 Display 2106 Lower Camera 2107 Obstacle Sensor 2108 Moving mechanism 2110 Arithmetic equipment 3001 Lighting device 5000 cabinets 5001 Display section 5002 Display section 5003 Speaker 5004 LED Lamp 5006 Connection terminal 5007 Sensor 5008 Microphone 5012 Support part 5013 Earphones 5100 Cleaning Robot 5101 Display 5102 Camera 5103 Brush 5104 Operation Buttons 5120 Garbage 5140 Portable electronic devices 5200 display area 5201 Display area 5202 Display area 5203 Display area 7101 enclosure 7103 Display section 7105 Stand 7107 Display section 7109 Operation Keys 7110 Remote Control Unit 7201 Main Unit 7202 enclosure 7203 Display section 7204 Keyboard 7205 External connection port 7206 Pointing device 7210 Display section 7401 enclosure 7402 Display section 7403 Operation Buttons 7404 External connection port 7405 Speaker 7406 Microphone 9310 Mobile Information Terminal 9311 Display Panel 9313 Hinge 9315 enclosure

Claims

1. An organic compound represented by the general formula (G2). 【Chemistry 1】 (However, in the above general formula (G2), Substituent R １ to substituent R １３ One of these is represented by the above general formula (G3), In the above general formula (G3), Ar represents a substituted or unsubstituted arylene group. The aforementioned arylene group has 6 to 13 carbon atoms. A represents a substituted or unsubstituted 9H-carbazolyl group or a substituted or unsubstituted anthryl group. Substituent R １ to substituent R １３ The others are, independently, hydrogen, alkyl groups, cyclic alkyl groups, or substituted or unsubstituted aryl groups. The alkyl group has 1 to 6 carbon atoms. The cyclic alkyl group has 3 to 7 carbon atoms. The substituted or unsubstituted aryl group has 6 to 13 carbon atoms.

2. In claim 1, In the above general formula (G2), Substituent R １ , substituent R ３ , substituent R ４ or substituent R １０ One of these is an organic compound represented by the general formula (G3).

3. An organic compound represented by the general formula (G4). 【Chemistry 2】 (However, in the above general formula (G4), Substituent R ２１ to substituent R ３５ is any one represented by the above general formula (G3), In the above general formula (G3), Ar represents a substituted or unsubstituted arylene group. The aforementioned arylene group has 6 to 13 carbon atoms. A represents a substituted or unsubstituted 9H-carbazolyl group or a substituted or unsubstituted anthryl group. Substituent R ２１ to substituent R ３５ The others are, independently, hydrogen, alkyl groups, cyclic alkyl groups, or substituted or unsubstituted aryl groups. The alkyl group has 1 to 6 carbon atoms. The cyclic alkyl group has 3 to 7 carbon atoms. The substituted or unsubstituted aryl group has 6 to 13 carbon atoms.

4. In claim 3, In the above general formula (G4), Substituent R ２１ , substituent R ２３ , substituent R ２４ or substituent R ３２ Any of the above is an organic compound represented by the general formula (G3).

5. In any one of claims 1 to 4, In the above general formula (G3), Ar is an organic compound consisting of a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenyldiyl group.

6. In any one of claims 1 to 5, In the above general formula (G3), A is an organic compound having a substituted or unsubstituted carbazo-9-yl group or a substituted or unsubstituted 9-antryl group.

7. The first electrode and The second electrode and The first layer and, It has a second layer, The second electrode has a region that overlaps with the first electrode, The first layer comprises a region sandwiched between the first electrode and the second electrode, The first layer comprises a light-emitting material and a charge-transporting material. The second layer comprises a region sandwiched between the first layer and the second electrode, The second layer comprises the charge transport material, The light-emitting device wherein the charge transport material is an organic compound according to any one of claims 1 to 6.

8. A light-emitting device having the light-emitting device described in claim 7 and a transistor or substrate.

9. A display device having the light-emitting device described in claim 7 and a transistor or substrate.

10. A lighting device comprising a light-emitting device according to claim 8 and a housing.

11. An electronic device comprising the display device described in claim 9, a sensor, an operation button, a speaker, or a microphone.

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