organic compounds

Abstract

This invention provides novel phenanthroline derivatives. [Solution] An organic compound represented by the following general formula (G1) is provided. Note that in general formula (G1), A 1 and A 2 Each of these is an independent group represented by the following general formula (g1). Also, in the following general formula (g1), R 11 ~R 18 Each of the following independently represents hydrogen (including deuterium) or a substituent, and p and q independently represent 0 to 3. 1 represents a divalent base, and n represents an integer from 0 to 3. Note that when n is 2 or greater, there are multiple Ar 1 These may be the same group or different groups. JPEG2026077608000035.jpg39167

Description

Technical Field

[0001] One aspect of the present invention relates to organic compounds, organic electronic devices, light-emitting devices, organic EL devices, electronic devices, and methods for synthesizing organic compounds.

[0002] Note that one aspect of the present invention is not limited to the above technical field. Examples of the technical field of one aspect of the present invention include compounds, light-emitting devices, organic EL devices, semiconductor devices, display devices, light-emitting devices, power storage devices, memory devices, electronic devices, lighting devices, input devices (e.g., touch sensors), input / output devices (e.g., touch panels), their driving methods, or their manufacturing methods.

Background Art

[0003] In recent years, display devices are expected to be applied to various uses. For example, as applications of large display devices, there are home television sets (also referred to as TVs or television receivers), digital signage, and public information displays (PIDs), etc. In addition, as portable information terminals, the development of smartphones and tablet terminals equipped with touch panels is underway.

[0004] At the same time, higher definition of display devices is also required. As devices that require high-definition display devices, for example, devices for virtual reality (VR), augmented reality (AR), substitutional reality (SR), and mixed reality (MR) are being actively developed.

[0005] As a display device, light-emitting devices (also called light-emitting elements) using organic compounds have been developed. Light-emitting devices that utilize the electroluminescence (EL) phenomenon (also called organic EL devices or light-emitting devices) have features such as being easy to make thin and light, being able to respond quickly to input signals, and being able to be driven using a DC constant voltage power supply, and are being applied to display devices.

[0006] Patent Document 1 discloses a light-emitting device with low driving voltage and good reliability, which uses a mixed film of a transition metal and an organic compound having lone pairs of electrons as the electron injection layer. [Prior art documents] [Patent Documents]

[0007] [Patent Document 1] Japanese Patent Publication No. 2018-201012 [Non-patent literature]

[0008] [Non-Patent Document 1] Fukuzaki S, et al. “High-luminance and Highly Reliable Tandem OLED Display Including New Intermediate Connector Designed for Photolithography Applications.”, Journal of the Society for Information Display. 2024. https: / / doi.org / 10.1002 / jsid.1294 [Overview of the project] [Problems that the invention aims to solve]

[0009] One aspect of the present invention aims to provide a novel phenanthroline derivative. Alternatively, another aspect of the present invention aims to provide a novel phenanthroline derivative with high heat resistance. Yet another aspect of the present invention aims to provide a novel phenanthroline derivative suitable for use in the intermediate layer of a tandem light-emitting device.

[0010] Furthermore, one aspect of the present invention aims to provide a novel light-emitting device, a novel display device, a novel display module, and a novel electronic device.

[0011] Furthermore, the description of these problems does not preclude the existence of other problems. One aspect of the present invention does not necessarily have to solve all of these problems. It is possible to extract other problems from the description in the specification, drawings, and claims. [Means for solving the problem]

[0012] One aspect of the present invention provides a phenanthroline dimer having an electron-donating group. This organic compound is highly heat-resistant and stable, and can be used as an intermediate layer in a tandem light-emitting device. Because a light-emitting device using this organic compound as an intermediate layer has good heat resistance, it is possible to suppress degradation due to storage and operation at high temperatures. One aspect of the present invention having these characteristics is an organic compound represented by the following general formula (G1).

[0013] [ka]

[0014] However, in the above general formula (G1), A 1 and A 2 Each of these is an independent group represented by the following general formula (g1).

[0015] [ka]

[0016] In the general formula (g1) above, R 11 to R 18 each independently represents either hydrogen (including deuterium) or an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a secondary amino group having 2 to 10 carbon atoms which may be substituted or unsubstituted, a monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms which may be substituted or unsubstituted, a heteroaryl group having 1 to 30 carbon atoms which may be substituted or unsubstituted, a cyano group, a halogen, a hydroxy group, an amide group, or a carbonyl group, and p and q each independently represent 0 to 3. Note that any two of R 11 to R 18 may be bonded to each other to form a ring. In addition, the aliphatic cyclic amino group represented by the general formula (g1) may have a condensed aromatic ring having 6 to 10 carbon atoms. Ar 1 represents a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 25 carbon atoms which may be substituted or unsubstituted, or a divalent heterocyclic group having 1 to 25 carbon atoms which may be substituted or unsubstituted, and n represents an integer of 0 to 3. Note that when n is 2 or more, the plurality of Ar 1 may be the same group or different groups.

[0017] Or, another aspect of the present invention is an organic compound represented by the following general formula (G2).

[0018] [Chemical formula]

[0019] However, in the general formula (G2) above, A 1 and A 2 are each independently a group represented by the following general formula (g1).

[0020] [Chemical formula]

[0021] In the above general formula (g1), R 11 ~R 18 Each of the following independently represents hydrogen (including deuterium), a C1-C10 alkyl group, a C3-C10 cycloalkyl group, a C1-C10 alkoxy group, a substituted or unsubstituted C2-C10 secondary amino group, a substituted or unsubstituted C6-C30 monovalent aromatic hydrocarbon group, a substituted or unsubstituted C1-C30 heteroaryl group, a cyano group, a halogen, a hydroxyl group, an amide group, or a carbonyl group, and p and q each independently represent 0 to 3. 11 ~R 18 Any two of them may be bonded to each other to form a ring. Furthermore, the aliphatic cyclic amino group represented by the general formula (g1) may have an aromatic ring with 6 to 10 carbon atoms fused to it. 1 Ar represents a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 1 to 25 carbon atoms, where n is an integer from 0 to 3. Note that when n is 2 or greater, there are multiple Ar groups. 1 These may be the same group or different groups.

[0022] Alternatively, another aspect of the present invention is an organic compound in which n is 0 in the above configuration.

[0023] Alternatively, in another aspect of the present invention, in the above configuration, R 11 , R 12 , R 17 and R 18 It is an organic compound in which hydrogen is present.

[0024] Alternatively, another aspect of the present invention is an organic compound in which p and q are 1 in the above configuration.

[0025] Alternatively, another aspect of the present invention is an organic compound represented by the following structural formula (100).

[0026] [ka]

[0027] Alternatively, another aspect of the present invention is an organic semiconductor device comprising the organic compound described in any of the above.

[0028] Alternatively, another aspect of the present invention is a light-emitting device comprising the organic compound described in any of the above.

[0029] Alternatively, another aspect of the present invention is a light-receiving device comprising the organic compound described in any of the above.

[0030] Alternatively, another aspect of the present invention is an organic electronic device using any of the above-described organic compounds as a cap layer.

[0031] Alternatively, another aspect of the present invention is an electronic device comprising the above-mentioned organic electronic device. [Effects of the Invention]

[0032] In one aspect of the present invention, a novel phenanthroline derivative can be provided. Alternatively, in another aspect of the present invention, a novel phenanthroline derivative with high heat resistance can be provided. In yet another aspect of the present invention, a novel phenanthroline derivative suitable for use in the intermediate layer of a tandem light-emitting device can be provided.

[0033] Furthermore, in one aspect of the present invention, a novel light-emitting device, a novel display device, a novel display module, and a novel electronic device can be provided.

[0034] Furthermore, the description of these effects does not preclude the existence of other effects. One aspect of the present invention does not necessarily have to possess all of these effects. Other effects can be extracted from the description, drawings, and claims. [Brief explanation of the drawing]

[0035] [Figure 1] Figures 1(A) to 1(C) are schematic diagrams of a light-emitting device according to one embodiment of the present invention. [Figure 2] Figures 2(A) and 2(B) are diagrams representing a display device according to one embodiment of the present invention. [Figure 3] Figures 3(A) and 3(B) are diagrams illustrating a display device according to one embodiment of the present invention. [Figure 4] Figures 4(A) to 4(E) are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 5] Figures 5(A) and 5(B) are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 6] Figures 6(A) to 6(D) are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 7] Figures 7(A) to 7(C) are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 8] Figures 8(A) to 8(C) are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 9] Figures 9(A) to 9(C) are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 10] Figures 10(A) and 10(B) are perspective views showing examples of the display module configuration. [Figure 11] Figures 11(A) and 11(B) are cross-sectional views showing examples of the configuration of a display device. [Figure 12] Figure 12 is a perspective view showing an example of a display device configuration. [Figure 13] Figure 13 is a cross-sectional view showing an example of the configuration of a display device. [Figure 14] Figure 14 is a cross-sectional view showing an example of the configuration of a display device. [Figure 15] Figure 15(A) is a cross-sectional view showing an example of the configuration of a display device. Figures 15(B) and 15(C) show the top surface layout of the pixels. [Figure 16] Figure 16 is a cross-sectional view showing an example of the configuration of a display device. [Figure 17]Figure 17(A) is a cross-sectional view showing an example of the configuration of a display device. Figure 17(B) is a diagram showing the top surface layout of pixels. Figure 17(C) is a diagram showing the top surface layout of pixels and microlenses. [Figure 18] Figures 18(A) to 18(D) illustrate an example of a wearable device. [Figure 19] Figures 19(A) through 19(F) show examples of electronic devices. [Figure 20] Figures 20(A) through 20(G) show examples of electronic devices. [Figure 21] Figures 21(A) through 21(C) show the 1H NMR spectra of mPrdPhen2P. [Figure 22] Figure 22 shows the luminance-current density characteristics of light-emitting device 1-1, light-emitting device 1-2, and comparative light-emitting device 1-1 and comparative light-emitting device 1-2. [Figure 23] Figure 23 shows the current efficiency-luminance characteristics of light-emitting device 1-1, light-emitting device 1-2, and comparative light-emitting device 1-1 and comparative light-emitting device 1-2. [Figure 24] Figure 24 shows the luminance-voltage characteristics of light-emitting device 1-1, light-emitting device 1-2, and reference light-emitting device 1-1 and reference light-emitting device 1-2. [Figure 25] Figure 25 shows the current density-voltage characteristics of light-emitting device 1-1, light-emitting device 1-2, and comparative light-emitting device 1-1 and comparative light-emitting device 1-2. [Figure 26] Figure 26 shows the electroluminescence spectra of light-emitting device 1-1, light-emitting device 1-2, and reference light-emitting device 1-1 and reference light-emitting device 1-2. [Figure 27] Figure 27 shows the luminance-current density characteristics of light-emitting device 2 and comparison light-emitting device 2. [Figure 28] Figure 28 shows the current efficiency-luminance characteristics of light-emitting device 2 and comparison light-emitting device 2. [Figure 29] Figure 29 shows the luminance-voltage characteristics of light-emitting device 2 and comparison light-emitting device 2. [Figure 30] Figure 30 shows the current density-voltage characteristics of light-emitting device 2 and comparison light-emitting device 2. [Figure 31] Figure 31 shows the field emission spectra of light-emitting device 2 and comparison light-emitting device 2. [Modes for carrying out the invention]

[0036] 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 shall not be construed as being limited to the descriptions of the embodiments shown below.

[0037] Furthermore, ordinal numbers such as "first," "second," etc., in this specification are added to avoid confusion of constituent elements and do not indicate any order or rank, such as process order or layering order. Even if an ordinal number is not used for a term in this specification, an ordinal number may be used in the claims to avoid confusion of constituent elements. Even if an ordinal number is used for a term in this specification, a different ordinal number may be used in the claims. Even if an ordinal number is used for a term in this specification, the ordinal number may be omitted in the claims.

[0038] (Embodiment 1) In recent years, display devices using light-emitting devices (synonymous with organic EL devices in this specification) have been put into practical use, and the realization of useful technologies and research and development are progressing.

[0039] For example, a tandem-type light-emitting device, which has multiple light-emitting units between a pair of electrodes with an intermediate layer that generates charge in between, can achieve higher current efficiency compared to a light-emitting device that has only one light-emitting unit between electrodes (also called a single-structure light-emitting device).

[0040] The intermediate layer of a tandem light-emitting device includes a charge generation layer (CGL). The CGL is a layer in which electrons and holes are generated by charge separation when a voltage is applied.

[0041] For CGL, it is preferable to use a laminated structure comprising a layer (n-type layer: first layer) containing an electron-transporting material and a material that acts as an electron donor to the electron-transporting material, and a layer (p-type layer: second layer) containing a hole-transporting material and a material that acts as an electron acceptor to the hole-transporting material. This is preferable because it facilitates the injection of electrons or holes into each light-emitting unit and reduces the driving voltage.

[0042] On the other hand, photolithography allows for the formation of denser patterns compared to mask deposition, and it is also a processing method that can easily be scaled up to large areas. Therefore, research is progressing on using photolithography to process organic compound films as an alternative to mask deposition when fabricating light-emitting devices.

[0043] However, when attempting to fabricate a tandem light-emitting device using photolithography, the n-type layer typically uses a material that has electron-donating properties to the electron transport material, such as alkali metals or alkaline earth metals, or compounds thereof (hereinafter also referred to as "alkali metal compounds, etc."). Because these alkali metal compounds, etc., are highly reactive with water or oxygen, they degrade rapidly and their electron-donating properties decrease not only when directly exposed to the atmosphere, but also when exposed to the atmosphere through multiple organic compound layers. Therefore, tandem light-emitting devices fabricated using photolithography, which requires exposing the surface of the EL layer to the atmosphere during the fabrication process, have a high driving voltage and have difficulty obtaining good characteristics.

[0044] In contrast, by using a layer containing a metal or metal compound and an organic compound having a phenanthroline ring in the n-type layer of the intermediate layer, a tandem-type light-emitting device with good characteristics can be obtained even after undergoing a photolithography process involving exposure of the EL layer to air (see, for example, Non-Patent Document 1).

[0045] In photolithography processing, a heating step is often required to remove moisture. Furthermore, automotive displays, for example, may be exposed to high temperatures for extended periods. Therefore, higher heat resistance is preferable for light-emitting devices.

[0046] Therefore, in one aspect of the present invention, an organic compound is provided that can be used as the n-type layer of a tandem light-emitting device, maintains good properties as a tandem light-emitting device even after processing by photolithography, and further provides a light-emitting device with higher heat resistance, having two phenanthroline skeletons and a group containing an aliphatic cyclic amine.

[0047] In other words, one aspect of the present invention provides an organic compound represented by the following general formula (G1).

[0048] [ka]

[0049] In the above general formula (G1), A 1 and A 2 Each of these is an independent group represented by the following general formula (g1).

[0050] [ka]

[0051] In the aliphatic cyclic amino group represented by the above general formula (g1), R 11 ~R 18Each of these independently represents hydrogen (including deuterium), or one of the following: a C1-C10 alkyl group, a C3-C10 cycloalkyl group, a C1-C10 alkoxy group, a substituted or unsubstituted C2-C10 secondary amino group, a substituted or unsubstituted C6-C30 monovalent aromatic hydrocarbon group, a substituted or unsubstituted C1-C30 heteroaryl group, a cyano group, a halogen, a hydroxyl group, an amide group, or a carbonyl group. 11 ~R 18 Any two of them may be joined together to form a ring.

[0052] Furthermore, in the aliphatic cyclic amino group represented by the general formula (g1) above, p and q each independently represent 0 to 3.

[0053] Furthermore, the aliphatic cyclic amino group represented by the above general formula (g1) may be fused with an aromatic ring having 6 to 10 carbon atoms.

[0054] Furthermore, in the aliphatic cyclic amino group represented by the above general formula (g1), Ar 1 Ar represents a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 1 to 25 carbon atoms, where n is an integer from 0 to 3. Note that when n is 2 or greater, there are multiple Ar groups. 1 These may be the same group or different groups.

[0055] Furthermore, the organic compound represented by the above general formula (G1) is preferred because, due to the two phenanthroline skeletons being bonded at the meta position in the central benzene ring, it can maintain a film with low crystallinity, thereby suppressing crystallization at high temperatures. In addition, the meta-substituted compound can achieve a lower sublimation temperature than the para-substituted compound, thus providing a compound with good sublimation properties and heat resistance. That is, in one aspect of the present invention, the organic compound represented by the following general formula (G2) is preferred.

[0056] [ka]

[0057] However, in the above general formula (G2), A 1 and A 2 Each of these is an aliphatic cyclic amino group represented by the above general formula (g1).

[0058] In the above general formulas (G1), (G2), and (g1), examples of alkyl groups having 1 to 10 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, isobutyl group, tert-butyl group, pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, neopentyl group, hexyl group, isohexyl group, heptyl group, octyl group, 3-methylpentyl group, 2-methylpentyl group, 2-ethylbutyl group, 1,2-dimethylbutyl group, 2,3-dimethylbutyl group, 2-ethylhexyl group, 1-ethylpropyl group, nonyl group, 3,7-dimethyl-1-octyl group, 3,7-dimethyl-2-octyl group, and decyl group. Among these, tert-butyl group or cyclohexyl group are preferred because they can reduce the refractive index.

[0059] In the above general formulas (G1), (G2), and (g1), examples of cycloalkyl groups having 3 to 10 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, and cyclodecyl groups, adamantyl, bicyclo[2.2.1]heptyl, tricyclo[5.2.1.0(2,6)]decyl, noradamantyl, 1-methylcyclohexyl, adamantyl, bicyclo[2,2,2]octyl, and norbornyl groups.

[0060] In the above general formulas (G1), (G2), and (g1), examples of alkoxy groups having 1 to 10 carbon atoms include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, n-pentyloxy, isopentyloxy, sec-pentyloxy, tert-pentyloxy, neopentyloxy, n-hexyloxy, isohexyloxy, sec-hexyloxy, tert-hexyloxy, neohexyloxy, and cyclohexyloxy groups.

[0061] In the above general formulas (G1), (G2), and (g1), the secondary amino group having 2 to 10 carbon atoms is preferably a cyclic secondary amine, for example, pyrrolidine-1-yl group, isoindole-2-yl group, dihydroisoindole-2-yl group, tetrahydroisoindole-2-yl group, hexahydroisoindole-2-yl group, hexahydroisoindorin-2-yl group, piperidine-1-yl group, aziridine-1-yl group, azetidine-1-yl group, octahydrocyclopenta[c]pyrrole-2-yl group, octahydro-4,7-methano-1H-isoindole-2-yl group, 2 Examples include azabicyclo[3.1.0]hexane-2-yl group, 3-azabicyclo[3.1.0]hexane-2-yl group, 3-azabicyclo[3.2.0]heptane-2-yl group, 5-azabispiro[3.4]octane-5-yl group, 8-azabicyclo[3.2.1]octane-8-yl group, 7-azabicyclo[2.2.1]heptane-7-yl group, 5-azabispiro[2.4]heptane-5-yl group, 5-azabicyclo[2.1.1]hexane-5-yl group, dimethylamino group, diethylamino group, diisopropylamino group, diphenylamino group, dicyclohexylamino group, etc. When a cyclic secondary amino group having 2 to 10 carbon atoms has substituents, examples of substituents include alkyl groups having 1 to 4 carbon atoms, cycloalkyl groups having 3 to 6 carbon atoms, or aryl groups having 6 to 13 carbon atoms.

[0062] Examples of monovalent aromatic hydrocarbon groups having 6 to 30 carbon atoms include phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, mesityl group, biphenyl-2-yl group (o-biphenyl group), biphenyl-3-yl group (m-biphenyl group), biphenyl-4-yl group (p-biphenyl group), 1-naphthyl group, 2-naphthyl group, phenylnaphthyl group, naphthylphenyl group, terphenyl group, fluorenyl group, 9,9-dimethylfluorenyl group, quaterphenyl group, spirobifluorenyl group, phenanthryl group, anthryl group, binaphthylphenyl group, fluoranthenyl group, and triphenylenyl group. When an aryl group having 6 to 30 carbon atoms has substituents, these substituents can include alkyl groups having 1 to 4 carbon atoms, cycloalkyl groups having 3 to 6 carbon atoms, aryl groups having 6 to 13 carbon atoms, halogens, or cyano groups.

[0063] Specific examples of heteroaryl groups having 1 to 30 carbon atoms include, for example, 1,3,5-triazine-2-yl group, 1,2,4-triazine-3-yl group, pyrimidine-4-yl group, pyrazine-2-yl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dinaphthofuranyl group, dinaphthothiophenyl group, indrocarbazolyl group, benzoflocarbazolyl group, benzothienocarbazolyl group, indenocarbazolyl group, dibenzocarbazolyl group, indolyl group, pyrrolyl group, 1,2,3-triazolyl group, and 1,2,4-triazoleyl group. Furthermore, if a heteroaryl group having 1 to 30 carbon atoms has substituents, these substituents may include alkyl groups having 1 to 4 carbon atoms, cycloalkyl groups having 3 to 6 carbon atoms, aromatic hydrocarbon groups having 6 to 13 carbon atoms, halogens, or cyano groups.

[0064] Examples of alkylene groups having 1 to 3 carbon atoms include methylene groups, ethylene groups, and propylene groups. Furthermore, as cycloalkylene groups having 3 to 10 carbon atoms, divalent groups obtained by removing one hydrogen atom from the aforementioned cycloalkyl groups with 3 to 10 carbon atoms can be used.

[0065] Examples of divalent heterocyclic groups having 1 to 25 carbon atoms include pyrimidine-diyl group, pyrazine-diyl group, pyridazine-diyl group, triazine-diyl group, bipyridine-diyl group, phenanthroline-diyl group, quinoxaline-diyl group, dibenzoquinoxaline-diyl group, quinazoline-diyl group, benzoquinazoline-diyl group, dibenzoquinazoline-diyl group, imidazo-diyl group, triazole-diyl group, oxadiazole-diyl group, benzimidazole-diyl group, phlodiazine-diyl group, benzoflopyrimidine-diyl group, thiophene-diyl group, and furan-diyl group. Examples of such groups include yl groups, benzothiophene-diyl groups, benzofuran-diyl groups, dibenzothiophene-diyl groups, dibenzofuran-diyl groups, benzonaphthothiophene-diyl groups, benzonaphthofuran-diyl groups, dinaphthothiophene-diyl groups, dinaphthofuran-diyl groups, piperazine-diyl groups, hexahydropyrimidine-diyl groups, hexahydrotriazine-diyl groups, decahydroquinoxaline-diyl groups, decahydronaphthyridine-diyl groups, imidazolidine-diyl groups, octahydropyrrolopyridine-diyl groups, and octahydropyrrolopyrrole-diyl groups. When a divalent heterocyclic group having 1 to 25 carbon atoms has substituents, such substituents may include alkyl groups having 1 to 4 carbon atoms, cycloalkyl groups having 3 to 6 carbon atoms, or aryl groups having 6 to 13 carbon atoms.

[0066] Examples of divalent aromatic hydrocarbon groups having 6 to 25 carbon atoms include phenylene, biphenyl-diyl, naphthalene-diyl, fluorene-diyl, acenaphthene-diyl, anthracene-diyl, phenanthrene-diyl, terphenyl-diyl, triphenylene-diyl, tetracene-diyl, benzoanthracene-diyl, pyrene-diyl, and spirobi[9H-fluorene]-diyl. When an arylene group having 6 to 30 carbon atoms has substituents, these substituents can be alkyl groups having 1 to 4 carbon atoms, cycloalkyl groups having 3 to 6 carbon atoms, or aryl groups having 6 to 13 carbon atoms.

[0067] As the aliphatic cyclic amino group represented by the above general formula (g1), groups represented by the following structural formulas (Am-1) to (Am-49) are preferred.

[0068] [ka]

[0069] [ka]

[0070] Examples of organic compounds represented by the above general formulas (G1) and (G2) include organic compounds represented by the following structural formulas (100) to (117).

[0071] [ka]

[0072] [ka]

[0073] [ka]

[0074] An organic compound according to one embodiment of the present invention having the above configuration can be an organic compound with good electron transport properties. Furthermore, because the organic compound according to one embodiment of the present invention can interact with metals, it can be suitably used as a material for the n-type intermediate layer in a tandem-type light-emitting device. Furthermore, because the organic compound according to one embodiment of the present invention has good heat resistance, it can provide a light-emitting device that is resistant to processing requiring high temperatures, storage at high temperatures, or operation, and is highly reliable. Moreover, because the organic compound according to one embodiment of the present invention has strong interaction with metals, it is less affected by exposure to air during the light-emitting device manufacturing process, and by using it in a tandem-type light-emitting device processed by photolithography, it is possible to provide a display device with good properties and high resolution.

[0075] Next, as an example of an organic compound according to one aspect of the present invention, a method for synthesizing the organic compound represented by the above general formula (G1) will be described using the following general formula (G1-1). Note that various reactions can be applied to synthesize general formula (G1), and the method is not limited to the one described below.

[0076] [ka]

[0077] In the above general formula (G1-1), R 11 ~R 18 Each of the following independently represents hydrogen (including deuterium), a C1-C10 alkyl group, a C3-C10 cycloalkyl group, a C1-C10 alkoxy group, a substituted or unsubstituted C2-C10 secondary amino group, a substituted or unsubstituted C6-C30 monovalent aromatic hydrocarbon group, a substituted or unsubstituted C1-C30 heteroaryl group, a cyano group, a halogen, a hydroxyl group, an amide group, or a carbonyl group, and p and q each independently represent 0 to 3. 11 ~R 18Any two of the different carbon atoms bonded to each other may bond to form a ring. Furthermore, the aliphatic cyclic amino group represented by the general formula (g1) may have an aromatic ring with 6 to 10 carbon atoms fused to it. 1 Ar represents a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 1 to 25 carbon atoms, where n is an integer from 0 to 3. Note that when n is 2 or greater, there are multiple Ar groups. 1 These may be the same group or different groups.

[0078] The organic compound represented by the above general formula (G1-1) can be synthesized by a simple synthesis scheme such as the one shown in the following synthesis scheme (A-1).

[0079] [ka]

[0080] In the above aliphatic cyclic amine derivative (a2), Q represents hydrogen when n is 0, and a boronyl group (-B(OH)2) when n is 1 or greater. 11 ~R 18 p and q are the same as in general formula (g1). Note that when using a boronyl group, boronic acid esters or cyclic triol borate salts may also be used.

[0081] In the synthesis scheme (A-1), if n is 0 in the aliphatic cyclic amine derivative (a2), an organic compound represented by general formula (G1-1) can be obtained by nucleophilic substitution reaction between compound (a1) and the aliphatic cyclic amine derivative (a2).

[0082] Examples of bases that can be used in the nucleophilic substitution reaction represented by the above synthesis scheme (A-1) include organic bases such as 1,8-diazabicyclo[5.4.0]-7-undecene (abbreviation: DBU®), triethylamine, sodium tert-butoxide, and potassium tert-butoxide, as well as inorganic bases such as potassium carbonate, cesium carbonate, sodium carbonate, sodium bicarbonate, potassium acetate, sodium acetate, tripotassium phosphate, and trisodium phosphate.

[0083] Solvents that can be used in the nucleophilic substitution reaction represented by the above synthesis scheme (A-1) include N-methyl-2-pyrrolidone, N,N-dimethylformamide, toluene, tetrahydrofuran, dioxane, and ethanol. However, the solvents that can be used are not limited to these. Furthermore, when using an organic base, it may be used as both a base and a solvent.

[0084] Furthermore, the reactions carried out in the above synthesis scheme (A-1) are not limited to nucleophilic substitution reactions; Buchwald-Hartwig reactions, coupling reactions using copper or copper compounds, etc., can also be used.

[0085] In the synthesis scheme (A-1), if n is 1 or greater in the aliphatic cyclic amine derivative (a2), the compound (a1) and the aliphatic cyclic amine derivative (a2) can be coupled by the Suzuki-Miyaura reaction to obtain the organic compound represented by general formula (G1-1).

[0086] When the above synthesis scheme (A-1) is carried out using the Suzuki-Miyaura reaction, suitable palladium catalysts include palladium(II) acetate, tetrakis(triphenylphosphine)palladium(O), bis(triphenylphosphine)palladium(II) dichloride, and tris(dibenzylideneacetone)dipalladium(O).

[0087] Ligands for the above palladium catalyst include 2-dicyclohexylphosphin-2',6'-dimethoxybiphenyl, di(1-adamantyl)-N-butylphosphine, (±)-2,2'-bis(diphenylphosphin)-1,1'-binaphthyl, tri(ortho-tolyl)phosphine, triphenylphosphine, 4,5-bis(diphenylphosphin)-9,9-dimethylxanthene (abbreviated as Xantphos), and tricyclohexylphosphine.

[0088] When the above synthesis scheme (A-1) is carried out using the Suzuki-Miyaura reaction, suitable bases include organic bases such as sodium tert-butoxide and potassium tert-butoxide, and inorganic bases such as potassium carbonate and sodium carbonate.

[0089] When the above synthesis scheme (A-1) is carried out using the Suzuki-Miyaura reaction, suitable solvents include toluene, xylene, mesitylene, benzene, tetrahydrofuran, and dioxane. However, the solvents that can be used are not limited to these.

[0090] Furthermore, the reaction carried out in the above synthesis scheme (A-1) is not limited to the Suzuki-Miyaura reaction; the Migita-Kosugi-Still coupling reaction using organotin compounds, coupling reactions using Grignard reagents, etc., can also be used.

[0091] While organic compounds according to one aspect of the present invention can be synthesized as described above, the present invention is not limited thereto, and may be synthesized by other synthesis methods.

[0092] This embodiment can be used in any combination with other embodiments and examples.

[0093] (Embodiment 2) This embodiment describes in detail a light-emitting device according to one aspect of the present invention. Figure 1(A) shows a diagram representing a light-emitting device according to one aspect of the present invention. The light-emitting device according to one aspect of the present invention has an organic compound layer 103 between a first electrode 101 formed on an insulating layer 1000 and a second electrode 102 facing the first electrode. The organic compound layer 103 has at least a light-emitting layer 113 and may further include other functional layers. In Figures 1(A) and (B), an example is shown in which a hole injection layer 111, a hole transport layer 112, an electron transport layer 114 and an electron injection layer 115 (charge generation layer 116) are included, but an exciton blocking layer, an intermediate layer, etc. may also be included. Note that the layer in contact with the light-emitting layer 113 among the hole transport layers 112 may be specifically called the electron blocking layer, and the layer in contact with the light-emitting layer among the electron transport layers 114 may be specifically called the hole blocking layer. In this embodiment, we will explain using the example where the first electrode 101 functions as the anode and the second electrode 102 functions as the cathode, but this can also be reversed.

[0094] In one embodiment of the present invention, the organic compound layer 103 contains the organic compound represented by general formula (G1) or general formula (G2) in Embodiment 1. Since the organic compound represented by general formula (G1) or general formula (G2) has electron transport properties, it is preferable that it is included in the electron transport layer 114, electron injection layer 115 and charge generation layer 116, hole blocking layer, light-emitting layer 113, intermediate layer, etc., in the light-emitting device shown in Figures 1(A) and (B).

[0095] In particular, the organic compounds represented by general formula (G1) or general formula (G2) form coordinate bonds with metals or metal compounds and improve the electron donor properties of the metals. Therefore, in the light-emitting devices shown in Figures 1(A) and (B), it is preferable to use them together with metals or metal compounds in the electron injection layer 115, the charge generation layer 116, and the intermediate layer.

[0096] The electron injection layer 115, charge generation layer 116, and intermediate layer containing the organic compound represented by general formula (G1) or general formula (G2) disclosed in Embodiment 1 can improve the electron donor properties of the metal or metal compound by coordinating the organic compound with the metal or metal compound. As a result, even when the organic compound layer 103 is exposed to an atmospheric environment, the function of the electron injection layer 115, charge generation layer 116, and intermediate layer is suppressed, thereby suppressing an increase in the driving voltage and providing a light-emitting device with good characteristics.

[0097] In other words, the light-emitting device having an electron injection layer 115, a charge generation layer 116, and an intermediate layer containing an organic compound represented by general formula (G1) or general formula (G2) as disclosed in Embodiment 1 and a metal or metal compound, does not experience a significant increase in driving voltage and can be made into a light-emitting device with good characteristics.

[0098] Furthermore, since the organic compounds represented by general formula (G1) or general formula (G2) disclosed in Embodiment 1 are organic compounds with good heat resistance, it is possible to provide a light-emitting device that is resistant to processing requiring high temperatures, storage at high temperatures, or operation, and is highly reliable.

[0099] Furthermore, because the organic compound according to one embodiment of the present invention has strong interactions with metals, it is less susceptible to the effects of atmospheric exposure during the manufacturing process of light-emitting devices. Therefore, by using it in tandem-type light-emitting devices that have undergone processing by photolithography, it is possible to provide a display device with good characteristics and high resolution.

[0100] In this embodiment, the first electrode 101 is an electrode including an anode, and the second electrode 102 is an electrode including a cathode. An example is shown in which the first electrode 101 is formed on the insulating layer 1000 side. However, a so-called reverse stacking configuration is also possible, in which the second electrode 102 is formed on the insulating layer 1000 side. In this case, the light-emitting device has a stacked structure in the following order from the insulating layer 1000 side: second electrode 102, electron injection layer 115, (electron transport layer 114,) light-emitting layer 113, (hole transport layer 112, hole injection layer 111,) first electrode 101. In the case of a light-emitting device with such a reverse stacking structure, the relatively stable hole injection layer 111 becomes the surface, making it possible to make a more reliable light-emitting device.

[0101] Furthermore, the first electrode 101 and the second electrode 102 may be formed as a single-layer structure or a multilayer structure. If they have a multilayer structure, the layer in contact with the organic compound layer 103 functions as the anode or cathode. When the electrodes have a multilayer structure, there are no constraints on the work function of the layers other than the layer in contact with the organic compound layer 103, and materials can be selected according to the required properties such as resistance, ease of processing, reflectivity, light transmittance, and stability.

[0102] The anode is preferably formed using a metal, alloy, conductive compound, or mixture thereof with a high work function (specifically, 4.0 eV or higher). Specifically, examples include indium tin oxide (ITO), indium tin silicon oxide (ITSO) containing silicon or silicon oxide, indium zinc oxide, and indium oxide (IWZO) containing tungsten oxide and zinc oxide. These conductive metal oxide films are usually deposited by sputtering, but they may also be fabricated using methods such as the sol-gel method. An example of a fabrication method is to form indium zinc oxide by sputtering using a target to which 1 to 20 wt% zinc oxide is added to indium oxide. Furthermore, indium oxide (IWZO) containing tungsten oxide and zinc oxide can also be formed by sputtering using a target containing 0.5-5 wt% tungsten oxide and 0.1-1 wt% zinc oxide relative to indium oxide. Other materials that can be used as anodes include, for example, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), aluminum (Al), or nitrides of metallic materials (e.g., titanium nitride). Alternatively, a layer of these materials can be used as the anode. For example, a film in which Al, Ti, and ITSO are layered on Ti is preferable because it has good reflectivity, is highly efficient, and enables high resolution of several thousand ppi. Alternatively, graphene can also be used as a material for the anode. Furthermore, by using a composite material capable of forming the hole injection layer 111 (described later) as the layer in contact with the anode (typically the hole injection layer), it becomes possible to select the electrode material regardless of the work function.

[0103] The hole injection layer 111 is provided in contact with the anode and has the function of facilitating the injection of holes into the organic compound layer 103. The hole injection layer 111 can be formed from phthalocyanine-based compounds or complex compounds such as phthalocyanine (abbreviated as H2Pc) and copper phthalocyanine (abbreviated as CuPc), aromatic amine compounds such as 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated as DPAB) and 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviated as DNTPD), or polymers such as poly(3,4-ethylenedioxythiophene) / polystyrene sulfonic acid (abbreviated as PEDOT / PSS).

[0104] Furthermore, the hole injection layer 111 may be formed from a substance having electron-accepting properties. Examples of substances having electron-accepting properties include organic compounds having electron-withdrawing groups (halogen groups, cyano groups, etc.), such as 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviated as F4-TCNQ), chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexazatriphenylene (abbreviated as HAT-CN), 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviated as F6-TCNNQ), and 2-(7-dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyrene-2-ylidene)malononitrile. In particular, compounds in which an electron-withdrawing group is bonded to a condensed aromatic ring having multiple heteroatoms, such as HAT-CN, are thermally stable and preferred. Furthermore, radialene derivatives having an electron-withdrawing group (especially halogen groups such as fluoro groups, cyano groups, etc.) are preferred because they have very high electron-accepting properties. Specific examples include α,α',α''-1,2,3-cyclopropanetriylidenates[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α',α''-1,2,3-cyclopropanetriylidenates[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], and α,α',α''-1,2,3-cyclopropanetriylidenates[2,3,4,5,6-pentafluorobenzeneacetonitrile]. In addition to the organic compounds mentioned above, other acceptor materials that can be used include transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide.In addition, the hole injection layer 111 can also be formed by phthalocyanine-based compounds or complex compounds such as phthalocyanine (abbreviated as H2Pc) and copper phthalocyanine (abbreviated as CuPc), aromatic amine compounds such as 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated as DPAB) and 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviated as DNTPD), or polymers such as poly(3,4-ethylenedioxythiophene) / polystyrene sulfonic acid (abbreviated as PEDOT / PSS). Accepting substances can extract electrons from adjacent hole transport layers (or hole transport materials) by applying an electric field.

[0105] Furthermore, it is preferable that the hole injection layer 111 be formed from a composite material containing the acceptor material and the hole transporting material.

[0106] Various organic compounds can be used as hole-transporting substances in composite materials, including aromatic amine compounds, heteroaromatic compounds, aromatic hydrocarbons, and polymer compounds (oligomers, dendrimers, polymers, etc.). -6 cm 2 It is preferable that the substance has a hole mobility of / Vs or greater. The hole-transporting substance used in the composite material is preferably a compound having a condensed aromatic hydrocarbon ring or a π-electron-rich heteroaromatic ring. As the condensed aromatic hydrocarbon ring, anthracene rings, naphthalene rings, etc. are preferred. As the π-electron-rich heteroaromatic ring, a condensed aromatic ring containing at least one of a pyrrole skeleton, a furan skeleton, or a thiophene skeleton is preferred, and specifically, a carbazole ring, a dibenzothiophene ring, or a ring in which an aromatic ring or heteroaromatic ring is further condensed thereon is preferred.

[0107] Such hole-transporting materials more preferably have at least one of the following skeletons: a carbazole skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton, and an anthracene skeleton. In particular, they may be 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. Furthermore, it is preferable that these hole-transporting materials have an N,N-bis(4-biphenyl)amino group, as this allows for the creation of light-emitting devices with a good lifetime.

[0108] Examples of substances possessing hole transport properties as described above 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-biphen Luamine (abbreviation: ThBA1BP), 4-(2-naphthyl)-4',4''-diphenyltriphenylamine (abbreviation: BBAβNB), 4-[4-(2-naphthyl)phenyl]-4',4''-diphenyltriphenylamine (abbreviation: BBAβNBi), 4,4'-diphenyl-4''-([2,1'-binaphthyl]-6-yl)triphenylamine (abbreviation: BBAαNβNB), 4,4'-diphenyl-4''-([2,1'-binaphthyl]-7-yl)triphenylamine (abbreviation: BBAαNβNB-03), 4,4'-diphenyl -4''-(7-phenyl)naphthyl-2-yltriphenylamine (abbreviation: BBAPβNB-03), 4,4'-diphenyl-4''-([2,2'-binaphthyl]-6-yl)triphenylamine (abbreviation: BBA(βN2)B), 4,4'-diphenyl-4''-([2,2'-binaphthyl]-7-yl)triphenylamine (abbreviation: BBA(βN2)B-03), 4,4'-diphenyl-4''-([1,2'-binaphthyl]-4-yl)triphenylamine (abbreviation: BBAβNαNB), 4,4'-diphenyl-4''-([1,2'-binaphthyl]-5-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''-phenyl Triphenylamine (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 (Biphenyl-4-yl)amine (abbreviation: YGTBi1BP-02), 4-[4'-(carbazole-9-yl)biphenyl-4-yl]-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: YGTBiβNB), N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-N-[4-(1-naphthyl)phenyl]-9,9'-spirobio[9H-fluorene]-2-amine (abbreviation: PCBNBSF), N,N-bis( Biphenyl-4-yl)-9,9'-spirobio[9H-fluorene]-2-amine (abbreviation: BBASF), N,N-bis(biphenyl-4-yl)-9,9'-spirobio[9H-fluorene]-4-amine (abbreviation: BBASF(4)), N-(biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobio[9H-fluorene]-4-amine (abbreviation: oFBiSF), N-(biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzofuran-4-amine (abbreviation: FrBiF), N-[4-(1-naphthyl)phenyl]-N-[3-(6-phenyldibenzofuran-4-yl)phenyl]-1-naphthylamine (abbreviation: mPDBfBNBN), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-phenyl-4'-[4-(9-phenylfluoren-9- [Iyl)phenyl]triphenylamine (abbreviation: BPAFLBi), 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazole-3-yl) Triphenylamine (abbreviation: PCBNBB), N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9'-spirobio[9H-fluorene]-2-amine (abbreviation: PCBASF), N-(biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H-fluorene-2-amine (abbreviation: PCBBiF), N,N-bis(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobio[9H-fluorene-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, 9-[3-(triphenylsilyl)phenyl]-3,9'-bi-9H-carbazole (abbreviation: PSiCzCz), 9'-[3-(triphenylsilyl)phenyl]-9'H-9,3':6',Examples include 9''-Telcarbazole (abbreviated as PSiCzGI).

[0109] Furthermore, other aromatic amine compounds that possess hole-transporting properties can also be used, such as 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), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviated as DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviated as DPA3B).

[0110] By forming the hole injection layer 111, the hole injection performance is improved, and a light-emitting device with a low driving voltage can be obtained.

[0111] Furthermore, among substances with acceptor properties, organic compounds with acceptor properties are easy to use because they are readily deposited and easy to form films.

[0112] The hole transport layer 112 is formed by including a material that has hole-transporting properties. The material that has hole-transporting properties is 1 × 10⁻¹⁶ -6 cm 2 It is preferable that the hole mobility is greater than or equal to / Vs.

[0113] The hole transport layer 112 may be a single-layer or multi-layer structure, but the layer in contact with the light-emitting layer 113 shall have the configuration described in Embodiment 1. Note that repeated descriptions of this configuration will be omitted.

[0114] When the hole transport layer 112 has a laminated structure, the layers other than the layer in contact with the light-emitting layer 113 do not necessarily have the configuration shown in Embodiment 1. In a hole transport layer having a laminated structure, the layers other than the layer in contact with the light-emitting layer 113 are formed by including a material having hole-transporting properties. The material having hole-transporting properties may be 1 × 10-6 cm 2 It is preferable that the hole mobility is greater than or equal to / Vs.

[0115] The above-mentioned hole-transporting substances include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminobiphenyl (abbreviated as TPD), N,N'-bis(9,9'-spirobi[9H-fluoren]-2-yl)-N,N'-diphenyl-4,4'-diaminobiphenyl (abbreviated as BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated as BPAFLP), and 4-phenyl-3 '-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 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 Compounds having an aromatic amine skeleton such as 9,9-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobio[9H-fluoren]-2-amine (abbreviation: PCBASF), 1,3-bis(N-carbazolyl)benzene (abbreviation: 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), 9,9'-bis(biphenyl-4-yl)-3,3'-bi-9H-carbazole (abbreviated as BisBPCz), 9,9'-bis(biphenyl-3-yl)-3,3'-bi-9H-carbazole (abbreviated as BismBPCz), 9-(biphenyl-3-yl)-9'-(biphenyl-4-yl)-9H,9'H-3,3'-bicarbazole (abbreviation: mBPCCBP), 9-(2-naphthyl)-9'-phenyl-3,3'-bi-9H-carbazole (abbreviation: βNCCP), 9-(3-biphenyl)-9'-(2-naphthyl)-3,3'-bi-9H-carbazole (abbreviation: βNCCmBP), 9-(4-biphenyl)-9'-(2-naphthyl)-3,3'-bi-9H-carbazole (abbreviation: βNCCBP), 9,9'-di-2-naphthyl-3,3'-9H,9'H-bicarbazole (abbreviation: BisβNCz), 9-(2-naphthyl)-9'-[1,1' :4',1”-terphenyl]-3-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':3',1”-terphenyl]-3-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':3',1”-terphenyl]-5'-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':4',1”-terphenyl]-4-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':3' ,1”-terphenyl]-4-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-(triphenylene-2-yl)-3,3'-9H,9'H-bicarbazole, 9-phenyl-9'-(triphenylene-2-yl)-3,3'-9H,9'H-bicarbazole (abbreviation: PCCzTp), 9,9'-bis(triphenylene-2-yl)-3,3'-9H,9'H-bicarbazole, 9-(4-biphenyl)-9'-(triphenylene-2-yl)-3,3'-9H,9'H-bicarbazole, 9-(tri Compounds having a carbazole skeleton such as phenylene-2-yl)-9'-[1,1':3',1”-terphenyl]-4-yl-3,3'-9H,9'H-bicarbazole, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio-9H-fluoren-1-amine, 9-[3-(triphenylsilyl)phenyl]-3,9'-bi-9H-carbazole (abbreviation: PSiCzCz), 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,Examples include compounds having a thiophene skeleton such as 8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviated as DBTFLP-III) and 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviated as DBTFLP-IV), and compounds having a furan skeleton such as 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviated as DBF3P-II) and 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviated as mmDBFFLBi-II). Among the above, compounds having an aromatic amine skeleton and compounds having a carbazole skeleton are preferred because they have good reliability, high hole transportability, and contribute to reducing the driving voltage. Furthermore, the organic compounds listed as hole-transporting substances used in the composite material of the hole injection layer 111 can also be suitably used as materials constituting the hole transport layer 112. It is even more preferable to use organic compounds having an amine skeleton and a fluorene skeleton. Moreover, organic compounds having an amine skeleton and a fluorene skeleton are preferable because they have good reliability and high hole transport properties, thereby reducing the power consumption of the light-emitting device.

[0116] The light-emitting layer 113 is a layer containing a light-emitting central material. It is also preferable that it contains a host material.

[0117] The luminescent central material can be a fluorescent material, a phosphorescent material, a thermally activated delayed fluorescence (TADF) material, or any other luminescent material.

[0118] Examples of materials that can be used as fluorescent materials in the light-emitting layer include the following. Other fluorescent materials can also be used.

[0119] 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-butylperylene (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(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(biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA) 9,10-bis(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(biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BPT), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl-4H-pyra n-4-ylidene)propanedinitrile (abbreviation: DCM1), 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinoridine-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluorantene-3,10-diamine (abbreviation) Name: 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'-diphenyl-N,N'-(1,6-pyrene-diyl)bis[(6-phenylbenzo[b]naph Examples include [1,2-d]furan)-8-amine] (abbreviated as 1,6BnfAPrn-03), N,N'-diphenyl-N,N'-bis(9-phenyl-9H-carbazole-2-yl)naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviated as 3,10PCA2Nbf(IV)-02), and 3,10-bis[N-(dibenzofuran-3-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviated as 3,10FrA2Nbf(IV)-02). In particular, condensed aromatic diamine compounds, such as pyrenediamine compounds like 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6BnfAPrn-03, are preferred because they have high hole-trapping properties and excellent luminescence efficiency or reliability.

[0120] Also, 5,9-diphenyl-5H,9H-[1,4]benzazabolino[2,3,4-kl]phenazavolin (abbreviation: DABNA-1), 9-(biphenyl-3-yl)-N,N,5,11-tetraphenyl-5H,9H-[1,4]benzazabolino[2,3,4-kl]phenazavolin-3-amine (abbreviation: DABNA-2), 2,12-di(tert-butyl)-5,9-di(4-tert-butylphenyl)-N,N-diphenyl-5H,9H-[1,4]benzazabolino[2,3,4-kl]phenazavolin- 7-amine (abbreviation: DPhA-tBu4DABNA), 2,12-di(tert-butyl)-N,N,5,9-tetra(4-tert-butylphenyl)-5H,9H-[1,4]benzazabolino[2,3,4-kl]phenazavolin-7-amine (abbreviation: tBuDPhA-tBu4DABNA), 2,12-di(tert-butyl)-5,9-di(4-tert-butylphenyl)-7-methyl-5H,9H-[1,4]benzazabolino[2,3,4-kl]phenazavolin (abbreviation: Me-tBu4DABNA), N 7 ,N 7 ,N 13 ,N 13 Condensed heteroaromatic compounds containing nitrogen and boron, such as ,5,9,11,15-octaphenyl-5H,9H,11H,15H-[1,4]benzazabolino[2,3,4-kl][1,4]benzazabolino[4',3',2':4,5][1,4]benzazabolino[3,2-b]phenazabolin-7,13-diamine (abbreviation: ν-DABNA) and 2-(4-tert-butylphenyl)benz[5,6]indro[3,2,1-jk]benzo[b]carbazole (abbreviation: tBuPBibc), particularly compounds having a diaza-boranaphtho-anthracene skeleton, can be suitably used because they produce blue emission with a narrow emission spectrum and good color purity.

[0121] In addition to these, there is 9,10,11-tris[3,6-bis(1,1-dimethylethyl)-9H-carbazolyl-9-yl]-2,5,15,18-tetrakis(1,1-dimethylethyl)indoro[3,2,1-de]indoro[3',2',1':8,1][1,4]benzazavolino[2,3,4-kl]phenazavolin (abbreviation: BBCz-G), 9,11-bis[ Compounds having an indole skeleton, such as 3,6-bis(1,1-dimethylethyl)-9H-carbazolyl-9-yl]-2,5,15,18-tetrakis(1,1-dimethylethyl)indoro[3,2,1-de]indoro[3',2',1':8,1][1,4]benzazavolino[2,3,4-kl]phenazavolin (abbreviation: BBCz-Y), can be suitably used.

[0122] In the light-emitting layer, suitable phosphorescent materials that can be used as the light-emitting central material include metal complexes, particularly iridium complexes or platinum complexes, and examples include the following.

[0123] Organometallic iridium complexes having a 4H-triazole skeleton, such as Tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium(III) (abbreviation: [Ir(mpptz-dmp)3]) and Tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Mptz)3]). , organometallic iridium complexes having a 1H-triazole skeleton such as 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]), fac-tris[1-(2,6-di Isopropylphenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpim)3]), Tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridine]iridium(III) (abbreviation: [Ir(dmpimpt-Me)3]), Tris(2-{1-[2,6-bis(1-methylethyl)phenyl]-1H-imidazole-2-yl-κN3}-4-cyanoph Organometallic iridium complexes having an imidazole skeleton, such as phenyl-κC)iridium(III) (abbreviation: CNImIr), organometallic complexes having a benzimidazolidene skeleton, such as tris[(6-tert-butyl-3-phenyl-2H-imidazo[4,5-b]pyrazine-1-yl-κC2)phenyl-κC]iridium(III) (abbreviation: [Ir(cb)3]), and bis[2-(4',6'-difluorophenyl)pyridinato-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’ Examples include organometallic iridium complexes with phenylpyridine derivatives having electron-withdrawing groups, such as iridium(III) acetylacetonate (FIracac), and platinum complexes such as (2-{3-[3-(3,5-di-tert-butylphenyl)benzimidazole-1-yl-2-ylidene-κC2]phenoxy-κC2}-9-(4-tert-butyl-2-pyridinyl-κN)carbazole-2,1-diyl-κC1)platinum(II) (PtON-TBBI). These compounds exhibit blue phosphorescence and have emission peaks in the wavelength range from 450 nm to 520 nm. Compounds in which some of the hydrogen atoms in these compounds are replaced with deuterium can also be used.

[0124] Also, 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- Organometallic iridium complexes having a pyrimidine skeleton, such as (2-methylphenyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm)2(acac)]), (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)2(acac)]), organometallic iridium complexes having a pyrazine skeleton, such as (acetylacetonato)bis(3,5-dimethyl-2-phenylpyradinato)iridium(III) (abbreviation: [Ir(mppr-Me)2(acac)]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyradinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]), and tris(2-phenylpyrimidinato-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)benzofloflo[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridinyl-κN2)phenyl-κC]iridium(III) (abbreviation: Ir(5mppy-d3)2(mbfpypy-d3)), {2-( Methyl-d3)-8-[4-(1-methylethyl-1-d)-2-pyridinyl-κN]benzofl[2,3-b]pyridin-7-yl-κC}bis{5-(methyl-d3)-2-[5-(methyl-d3)-2-pyridinyl-κN]phenyl-κC}iridium(III) (abbreviation: Ir(5mtpy-d6)2(mbfpypy-iPr-d4)), [2-(methyl-d3) -8-(2-pyridinyl-κN)benzofloxacin[2,3-b]pyridinyl-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(ppy)2(mbfpypy-d3)), [2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) )(abbreviation: Ir(ppy)2(mdppy)), [2-(4-d3-methyl-5-phenyl-2-pyridinyl-κN2)phenyl-κC]bis[2-(5-d3-methyl-2-pyridinyl-κN2)phenyl-κC]iridium(III)(abbreviation: [Ir(5mppy-d3)2(mdppy-d3)]), [2-methyl-8-(2-pyridinyl-κN)benzofloxacin[2,In addition to organometallic iridium complexes with a pyridine skeleton such as [3-b]pyridine-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(ppy)2(mbfpypy)]), [2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium (abbreviation: [Ir(ppy)2(mdppy)]), and tris{2-[5-(methyl-d3)-4-phenyl-2-pyridinyl-κN]phenyl-κC}iridium(III) (abbreviation: Ir(5m4dppy-d3)3), there are also organometallic iridium complexes with a pyridine skeleton such as (2-{1-(5-tert-butylbiphenyl-2-yl)-4-[3-tert-butyl-5-(4-phenyl-2-pyridinyl-κN Examples include organometallic platinum complexes such as [phenyl-κC6]-2-benzimidazolyl-κN3}-4,6-di-tert-butylphenolate-κO)platinum(II) (abbreviation: Pt(tBudppymmtBubiz-tBubp)) and [2-(4-(3,5-di-tert-butylphenyl)-6-{3-[4-(5'-tert-butyl[1,1':3',1''-terphenyl]-2'-yl)-2-pyridinyl-κN]phenyl-κC2}-2-pyridinyl-κN)phenolate-κO]platinum(II) (abbreviation: Pt(4tButpppypyp-mmtBup)), and rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [Tb(acac)3(Phen)]). These compounds primarily exhibit phosphorescence with a green hue, and have emission peaks in the wavelength range of 500 nm to 600 nm. Organometallic iridium complexes with a pyrimidine skeleton are particularly preferred due to their outstanding reliability and luminescence efficiency. Compounds in which some of the hydrogen atoms are replaced with deuterium can also be used.

[0125] Furthermore, organometallic iridium complexes having a pyrimidine skeleton, such as (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)]), and bis[4,6-di(naphthalene-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(d1npm)2(dpm)]), Organometallic iridium complexes with a pyrazine skeleton, such as (acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(tppr)2(dpm)]), and (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq)2(acac)]), and 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)]), (3,7-diethyl-4,6-nonanedionato-κO4,κO6)bis[2,4-dimethyl-6-[7-(1-methylethyl)-1-isoquinolinyl-κN]phenyl-κC]iridium(III), (3,7-diethyl-4,6-nonanedionato-κO4,κO6)bis[2,4-dimethyl-6-[5-(1-methylethyl)-2-quinolinyl-κN]phenyl-κC]iridium(III) are organometallic iridium compounds with a pyridine skeleton. In addition to dinium complexes, other examples include platinum complexes such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviated as PtOEP), and rare earth metal complexes such as tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviated as [Eu(DBM)3(Phen)]) and tris[1-(2-tenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviated as [Eu(TTA)3(Phen)]). These compounds exhibit phosphorescence with a red hue and have emission peaks in the wavelength range of 600 nm to 700 nm. Furthermore, organometallic iridium complexes with a pyrazine skeleton yield red emission with good chromaticity. Compounds in which some of the hydrogen atoms in these compounds are replaced with deuterium can also be used.

[0126] In addition to the phosphorescent compounds described above, other known phosphorescent compounds may be selected and used.

[0127] As TADF materials, fullerenes and their derivatives, acridines and their derivatives, eosin derivatives, etc., can be used. Also, metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd) can be used. Examples of metal-containing porphyrins include protoporphyrin-tin fluoride complexes (SnF2(Proto IX)), mesoporphyrin-tin fluoride complexes (SnF2(Meso IX)), hematoporphyrin-tin fluoride complexes (SnF2(Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complexes (SnF2(Copro III-4Me)), octaethylporphyrin-tin fluoride complexes (SnF2(OEP)), etioporphyrin-tin fluoride complexes (SnF2(Etio I)), and octaethylporphyrin-platinum chloride complexes (PtCl2OEP), as shown in the following structural formulas.

[0128] [ka]

[0129] Furthermore, the following structural formulas represent 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 (abbreviation: PCCzPTzn) Heterocyclic compounds having one or both of a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring can also be used, such as PXZ-TRZ, 3-[4-(5-phenyl-5,10-dihydrophenazine-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), and 10-phenyl-10H,10'H-spiro[acridine-9,9'-anthracene]-10'-one (abbreviated as ACRSA). 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. 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. Furthermore, among the skeletons having a π-electron-excess heteroaromatic ring, the acridine skeleton, phenoxazine skeleton, phenothiazine skeleton, furan skeleton, thiophene skeleton, and pyrrole skeleton are preferred because they are stable and reliable, and therefore it is preferable to have at least one of these skeletons.Furthermore, a dibenzofuran skeleton is preferred as the furan skeleton, and a dibenzothiophene skeleton is preferred as the thiophene skeleton. In addition, as the pyrrole skeleton, indole skeleton, carbazole skeleton, indrocarbazole skeleton, bicarbazole skeleton, and 3-(9-phenyl-9H-carbazole-3-yl)-9H-carbazole skeleton are particularly preferred. Substances in which a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring are directly bonded are particularly preferred because both the electron-donating and electron-accepting properties of the π-electron-rich heteroaromatic ring are strengthened, and the energy difference between the S1 and T1 levels is reduced, thus efficiently obtaining thermally activated delayed fluorescence. In addition, an aromatic ring to which an electron-withdrawing group such as a cyano group is bonded may be used instead of the π-electron-deficient heteroaromatic ring. Furthermore, aromatic amine skeletons, phenazine skeletons, etc., can be used as the π-electron-rich skeleton. 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 and volanthrene, aromatic rings having a nitrile group or a cyano group such as benzonitrile or cyanobenzene, heteroaromatic rings, carbonyl skeletons such as benzophenone, phosphine oxide skeletons, sulfone skeletons, etc., can be used. In this way, π-electron-deficient skeletons and π-electron-excess skeletons can be used instead of at least one of π-electron-deficient heteroaromatic rings and π-electron-excess heteroaromatic rings.

[0130] [ka]

[0131] Furthermore, as the TADF material, a TADF material in which the singlet excited state and the triplet excited state are in thermal equilibrium may be used. Since such a TADF material has a shorter luminescence lifetime (excitation lifetime), it is possible to suppress the decrease in efficiency in the high-brightness region of the light-emitting device. Specifically, materials with the molecular structure shown below are examples.

[0132] [ka]

[0133] TADF materials are materials that have a small energy difference between the S1 and T1 levels and possess the ability to convert energy from triplet excitation energy to singlet excitation energy through reverse intersystem crossing. Therefore, triplet excitation energy can be upconverted to singlet excitation energy with only a small amount of thermal energy (reverse intersystem crossing), and singlet excited states can be efficiently generated. Furthermore, triplet excitation energy can be converted into luminescence.

[0134] Furthermore, an excited complex (also called an exciplex) that forms an excited state with two types of substances has an extremely small energy difference between the S1 and T1 levels and functions as a TADF material that can convert triplet excitation energy into singlet excitation energy.

[0135] Furthermore, the phosphorescence spectrum observed at low temperatures (e.g., 77K to 10K) can be used as an indicator of the T1 level. For TADF materials, when a tangent is drawn at the short-wavelength tail of the fluorescence spectrum and the energy at the wavelength of the extrapolation is taken as the S1 level, and when a tangent is drawn at the short-wavelength tail of the phosphorescence spectrum and the energy at the wavelength of the extrapolation is taken as the T1 level, it is preferable that the energy difference between S1 and T1 is 0.3 eV or less, and more preferably 0.2 eV or less.

[0136] 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.

[0137] Various carrier transport materials can be used as the host material for the light-emitting layer, such as materials with electron transport properties and / or hole transport properties, and the TADF material mentioned above.

[0138] Preferred materials with hole transport properties include organic compounds having an amine skeleton or a π-electron-rich heteroaromatic ring skeleton. Preferred π-electron-rich heteroaromatic rings are condensed aromatic rings containing at least one of the following: acridine skeleton, phenoxazine skeleton, phenothiazine skeleton, furan skeleton, thiophene skeleton, and pyrrole skeleton. Specifically, carbazole rings, dibenzothiophene rings, or rings obtained by further condensing an aromatic ring or heteroaromatic ring with these are preferred.

[0139] Organic compounds having such hole-transporting properties more preferably have at least one of the following skeletons: a carbazole skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton, and an anthracene skeleton. In particular, they may be 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. Furthermore, it is preferable that these hole-transporting organic compounds are substances having an N,N-bis(4-biphenyl)amino group, as this allows for the creation of light-emitting devices with a good lifetime.

[0140] Preferred organic compounds include, for example, the following: 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminobiphenyl (abbreviated as TPD), N,N'-bis(9,9'-spirobi[9H-fluoren]-2-yl)-N,N'-diphenyl-4,4'-diaminobiphenyl (abbreviated as BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated as BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9- 4,4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: mBPAFLP), 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 Compounds having an aromatic amine skeleton such as 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]-9,9'-spirobio[9H-fluoren]-2-amine (abbreviation: PCBASF), 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)biphenyl ( Abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviation: CzTP), 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 3,9-bis(9-phenyl-9H-carbazole-3-yl)-9H-carbazole (abbreviation: PCCzPC), 9-(biphenyl-4-yl)-9'-phenyl-3,3'-bi-9H-carbazole (abbreviation: PCCzBP), 9,9'-bis(biphenyl-4-yl)-3,3'-bi-9H-carbazole (abbreviation: BisBPCz), 9,9'-Bis(biphenyl-3-yl)-3,3'-bi-9H-carbazole (abbreviation: BismBPCz), 9-(biphenyl-3-yl)-9'-(biphenyl-4-yl)-9H,9'H-3,3'-bicarbazole (abbreviation: mBPCCBP), 9-(2-naphthyl)-9'-phenyl-3,3'-bi-9H-carbazole (abbreviation: βNCCP), 9-(3-biphenyl)-9'-(2-naphthyl)-3,3'-bi-9H-carbazole (abbreviation: βNCCmBP), 9-(4-biphenyl)-9'-(2-naphthyl)-3, 3'-bi-9H-carbazole (abbreviation: βNCCBP), 9,9'-di-2-naphthyl-3,3'-9H,9'H-bicarbazole (abbreviation: BisβNCz), 9-(2-naphthyl)-9'-[1,1':4',1”-terphenyl]-3-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':3',1”-terphenyl]-3-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':3',1”-terphenyl]-5'-yl-3,3'-9H ,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':4',1”-terphenyl]-4-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-[1,1':3',1”-terphenyl]-4-yl-3,3'-9H,9'H-bicarbazole, 9-(2-naphthyl)-9'-(triphenylene-2-yl)-3,3'-9H,9'H-bicarbazole, 9-phenyl-9'-(triphenylene-2-yl)-3,3'-9H,9'H-bicarbazole (abbreviation: PCCzTp), 9,9'-bis(triphenylene-2-yl)-3,3'-9H,9'H-bicarbazole, 9-(4-biphenyl)-9'-(triphenylene-2-yl)-3,3'-9H,9'H-bicarbazole, 9-(triphenylene-2-yl)-9'-[1,1':3',1”-terphenyl]-4-yl-3,3'-9H,9'H-bicarbazole, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio-9H-fluoren-1-amine, 9-[3-(triphenylsilyl)phenyl]-3,Compounds containing a carbazole skeleton, such as 9'-bi-9H-carbazole (abbreviation: PSiCzCz), 9'-[3-(triphenylsilyl)phenyl]-9'H-9,3':6',9''-telcarbazole (abbreviation: PSiCzGI), 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), and 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-I). Examples include compounds having a thiophene skeleton such as 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviated as DBTFLP-IV), and compounds having a furan skeleton such as 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviated as DBF3P-II) and 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviated as mmDBFFLBi-II). Among the above, compounds having an aromatic amine skeleton or a carbazole skeleton are preferred because they have good reliability, high hole transportability, and contribute to reducing the driving voltage. In addition, organic compounds listed as examples of hole transportable materials in the hole transport layer can also be used.

[0141] For materials exhibiting electron transport properties, the electron mobility at which the square root of the electric field strength [V / cm] is 600 is 1 × 10⁻⁶. -7 cm 2 / Vs or more, preferably 1 × 10 -6 cm 2 A material having an electron mobility of / Vs or higher is preferred. However, any material with higher electron transport capabilities than holes can be used.

[0142] Preferred electron-transporting materials include metal complexes such as 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-benzoxazollyl)phenolato]zinc(II) (abbreviated as ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviated as ZnBTZ), as well as organic compounds having a π-electron-deficient heteroaromatic ring. Examples of organic compounds having a π-electron-deficient heteroaromatic ring skeleton include organic compounds containing a heteroaromatic ring having an azole skeleton, organic compounds containing a heteroaromatic ring having a pyridine skeleton, organic compounds containing a heteroaromatic ring having a diazine skeleton, and organic compounds containing a heteroaromatic ring having a triazine skeleton.

[0143] Among these, organic compounds containing heteroaromatic rings having a diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton), organic compounds containing heteroaromatic rings having a pyridine skeleton, and organic compounds containing heteroaromatic rings having a triazine skeleton are preferred due to their good reliability. In particular, organic compounds containing heteroaromatic rings having a diazine (pyrimidine or pyrazine) skeleton and organic compounds containing heteroaromatic rings having a triazine skeleton have high electron transport properties and contribute to reducing the driving voltage. Furthermore, benzoflopyrimidine skeletons, benzothienopyrimidine skeletons, benzoflopyrazine skeletons, and benzothienopyrazine skeletons are preferred because they have high acceptability and good reliability.

[0144] As organic compounds having a π-electron-deficient heteroaromatic ring skeleton, the following organic compounds are preferred, for example: 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), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazole-2-yl)phenyl]-9H-carbazole (abbreviated as CO11). Organic compounds having an azole skeleton, such as 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), 4,4'-bis(5-methylbenzoxazole-2-yl)stilbene (abbreviation: BzOs), 3,5-bis[3-(9H-carbazole-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3 ,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), vasophenanthroline (abbreviation: Bphen), vasocuproin (abbreviation: BCP), 2,9-di(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen), 2,2'-(1,3-phenylene)bis(9-phenyl-1,10-phenanthroline) (abbreviation: mPPhen2P), 2-[3-(2-triphenylenyl)phenyl]-1,10-phenanthroline (abbreviation: mTpPPhen), 2- Organic compounds containing heteroaromatic rings with a pyridine skeleton, such as phenyl-9-(2-triphenylenyl)-1,10-phenanthroline (abbreviation: Ph-TpPhen), 2-[4-(9-phenanthryl)-1-naphthyl]-1,10-phenanthroline (abbreviation: PnNPhen), and 2-[4-(2-triphenylenyl)phenyl]-1,10-phenanthroline (abbreviation: pTpPPhen), 2-{3-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-9-yl]phenyl}dibenzo[f,[h]Quinoxaline (abbreviation: 2mPCCzPDBq), 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]Quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]Quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]Quinoxaline (abbreviation: 2mCzBPDBq), 2-[4'-(9-phenyl-9H-carbazol-3-yl)-3,1' -Biphenyl-1-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mpPCBPDBq), 2-[4-(3,6-diphenyl-9H-carbazole-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPDBq-II), and 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II), 9-[3'-(dibenzothiophen- [4-yl)biphenyl-3-yl]naphtho[1',2':4,5]flo[2,3-b]pyrazine (abbreviation: 9mDBtBPNfpr), 9-[3'-(dibenzothiophen-4-yl)biphenyl-4-yl]naphtho[1',2':4,5]flo[2,3-b]pyrazine (abbreviation: 9pmDBtBPNfpr), 4,6-bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(dibenzothiophen-4-yl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6-bi Su[3-(9H-carbazole-9-yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), 9,9'-[pyrimidine-4,6-diylbis(biphenyl-3,3'-diyl)]bis(9H-carbazole) (abbreviation: 4,6mCzBP2Pm), 8-(biphenyl-4-yl)-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzoflo[3,2-d]pyrimidine (abbreviation: 8BP-4mDBtPBfpm), 3,8-bis[3-(dibenzothiophen-4-yl)phenyl]benzoflo[2,3-b]pyrazine (abbreviation: 3,8mDBtP2Bfpr), 4,8-bis[3-(dibenzothiophen-4-yl)phenyl]-[1]benzoflo[3,2-d]pyrimidine (abbreviation: 4,8mDBtP2Bfpm), 8-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]flo[3,2-d]pyrimidine (abbreviation: 8mDBtBPNfpm), 8-([2,2'-binaphthalene]-6-yl)-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzoflo[3,2-d]pyrimidine (abbreviation: 8(βN2)-4mDBtPBf pm), 2,2'-(pyridine-2,6-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviation: 2,6(P-Bqn)2Py), 2,2'-(pyridine-2,6-diyl)bis{4-[4-(2-naphthyl)phenyl]-6-phenylpyrimidine} (abbreviation: 2,6(NP-PPm)2Py), 6-(biphenyl-3-yl)-4-[3,5-bis(9H-carbazole-9-yl)phenyl]-2-phenylpyrimidine (abbreviation: 6mBP-4Cz2PPm), 2,6-bis(4-naphthalene-1-ylphenyl)-4-[4-(3-pyridyl)phenyl [phenyl]pyrimidine (abbreviation: 2,4NP-6PyPPm), 4-[3,5-bis(9H-carbazole-9-yl)phenyl]-2-phenyl-6-(biphenyl-4-yl)pyrimidine (abbreviation: 6BP-4Cz2PPm), 7-[4-(9-phenyl-9H-carbazole-2-yl)quinazoline-2-yl]-7H-dibenzo[c,g]carbazole (abbreviation: PC-cgDBCzQz), 8-(p-terphenyl-3-yl)-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofloflo[3,2-d]pyrimidine (abbreviation: 8mpTP Organic compounds having a diazine skeleton such as -4mDBtPBfpm), 11-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]phenanthro[9',10':4,5]fl[2,3-b]pyrazine (abbreviation: 11mDBtBPPnfpr), 2-(biphenyl-4-yl)-4-phenyl-6-(9,9'-spirobio[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), 2-{4-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 9-[3-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl]-9'-phenyl-2 ,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn-02), 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn), 5-[3-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl]-7,7-dimethyl-5H,7H-indeno[2,1-b]carbazole (abbreviation: mINc(II)PTzn), 2-{3-[3-(dibenzothiophen-4-yl)phenyl]phenyl}-4,6-diphenyl -1,3,5-triazine (abbreviation: mDBtBPTzn), 2,4,6-tris[3'-(pyridin-3-yl)biphenyl-3-yl]-1,3,5-triazine (abbreviation: TmPPPyTz), 2-[3-(2,6-dimethyl-3-pyridinyl)-5-(9-phenanthryl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mPn-mDMePyPTzn), 11-[4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine-2-yl]-11,12-dihydro-12-phenylindro[2,3 -a]carbazole (abbreviation: BP-Icz(II)Tzn), 2-[3'-(triphenylene-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mTpBPTzn), 3-[9-(4,6-diphenyl-1,3,5-triazine-2-yl)-2-dibenzofuranyl]-9-phenyl-9H-carbazole (abbreviation: PCDBfTzn), 2-(biphenyl-3-yl)-4-phenyl-6-[8-([1,1':4',1''-terphenyl]-4-yl)-1-dibenzofuranyl]-1,3,5-triazine (abbreviation: mBP-TPDBfTzn), 2-[4-(2-naphthyl)phenyl]-4-phenyl-6-spiro[9H-fluoren-9,9'-[9H]xanthene]-4-yl-1,3,5-triazine (abbreviation: βNP-SFx(4)Tzn), 9,9'-{6-[3-(triphenylsilyl)phenyl]-1,3,5-triazine-2,4-diyl}bis(9H-carbazole) Abbreviation: SiTrzCz2), 2-phenyl-4,6-bis[3-(triphenylsilyl)phenyl]-1,3,5-triazine (abbreviation: mSiTrz), 11-[4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine-2-yl]-11,12-dihydro-12-(biphenyl-3-yl)indro[2,3-a]carbazole (abbreviation: BP-mBPIcz(II)Tzn), 3 -{3-[9-(4,6-diphenyl-1,3,5-triazine-2-yl)-2-dibenzofuranyl]phenyl}-9-phenyl-9H-carbazole (abbreviation: mPCPDBfTzn), 9,9'-[6-(biphenyl-4-yl)-2-phenyl-1,3,5-triazine-4,3''-diyl]bis(9H-carbazole) (abbreviation: Cz-pmCzBPTzn), 3-phenyl-9-[4-phenyl Examples of organic compounds containing heteroaromatic rings having a triazine skeleton include phenyl-6-(9-phenyl-3-dibenzofuranyl)-1,3,5-triazine-2-yl]-9H-carbazole (abbreviated as PDBf-PCzTzn) and 9-[4-(4,6-diphenyl-1,3,5-triazine-2-yl)-2-dibenzothienyl]-2-phenyl-9H-carbazole (abbreviated as PCzDBtTzn). Furthermore, organic compounds containing heteroaromatic rings having a diazine skeleton, or heteroaromatic rings having a pyridine skeleton, or heteroaromatic rings having a triazine skeleton are preferred due to their good reliability. In particular, organic compounds containing heteroaromatic rings having a diazine (pyrimidine or pyrazine) skeleton, or heteroaromatic rings having a triazine skeleton, exhibit high electron transport properties and contribute to reducing the driving voltage.

[0145] Furthermore, the organic compounds represented by general formula (G1) or general formula (G2) disclosed in Embodiment 1 can also be suitably used as host materials having electron transport properties.

[0146] The TADF materials listed above can be used as host materials. When a TADF material is used as a host material, the triplet excitation energy generated by the TADF material is converted into singlet excitation energy through reverse intersystem crossing, and this energy is then transferred to the light-emitting material, thereby increasing the luminescence efficiency of the light-emitting device. In this case, the TADF material functions as an energy donor, and the light-emitting material functions as an energy acceptor.

[0147] 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.

[0148] 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.

[0149] 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 material. To achieve this, it is preferable that the fluorescent material 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 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 material with little effect on carrier transport or carrier recombination. Here, the luminescent phosphoform refers to the atomic group (skeleton) that causes luminescence in the fluorescent material. The luminescent phosphophore preferably has a skeleton containing π bonds, preferably contains an aromatic ring, and preferably has a condensed aromatic ring or a condensed heteroaromatic ring. Examples of such luminescent phosphophores include phenanthrene skeletons, stilbene skeletons, acridone skeletons, phenoxazine skeletons, phenothiazine skeletons, naphthalene skeletons, anthracene skeletons, fluorene skeletons, chrysene skeletons, triphenylene skeletons, tetracene skeletons, pyrene skeletons, perylene skeletons, coumarin skeletons, quinacridone skeletons, and naphthobisbenzofuran skeletons. Fluorescent materials having naphthalene, anthracene, fluorene, chrysene, triphenylene, tetracene, pyrene, perylene, coumarin, quinacridone, and naphthobisbenzofuran skeletons are particularly preferred due to their high fluorescence quantum yield.

[0150] When using a fluorescent material as the light-emitting material, a material having an acene skeleton, particularly an anthracene skeleton, is preferred as the host material. Using a material having an anthracene skeleton as the host material for a fluorescent material makes it possible to realize a light-emitting layer with good luminescence efficiency and durability. Among the materials having an anthracene skeleton to be used as the host material, a material having a diphenylanthracene skeleton, particularly a 9,10-diphenylanthracene skeleton, is preferred because it is chemically stable. Furthermore, while a carbazole skeleton is preferred as the host material because it improves hole injection and transport, a benzocarbazole skeleton, in which a benzene ring is further condensed onto the carbazole, is even more preferred because the HOMO level is about 0.1 eV higher than when only a carbazole skeleton is present, making it easier for holes to enter. In particular, a dibenzocarbazole skeleton is preferred as the HOMO level is about 0.1 eV higher than when only a carbazole skeleton is present, making it easier for holes to enter, and it also exhibits excellent hole transport properties and high heat resistance. Therefore, a more preferred host material is a substance having both a 9,10-diphenylanthracene skeleton and a carbazole skeleton (or a benzocarbazole skeleton or dibenzocarbazole skeleton). Furthermore, from the viewpoint of hole injection and transport, a benzofluorene skeleton or a dibenzofluorene skeleton may be used instead of the carbazole skeleton. Additionally, it is preferable to include a dibenzofuran skeleton because reliability can be ensured without lowering the T1 level.

[0151] Examples of such substances include 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviated as PCzPA), 3-[4-(1-naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviated as PCPN), 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviated as CzPA), 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated as cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl]benzo[b]naphtho[1,2-d]furan (abbreviated as 2mBnfPPA), and 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-(1-naphthyl)-10-(2-naphthyl)anthracene (abbreviation: α,βADN), 2-(10-phenylanthracene-9-yl)dibenzofuran, 2-(10-phenyl-9-anthryl)ben Examples include zo[b]naphtho[2,3-d]furan (abbreviated as Bnf(II)PhA), 9-(2-naphthyl)-10-[3-(2-naphthyl)phenyl]anthracene (abbreviated as βN-mβNPAnth), and 1-{4-[10-(biphenyl-4-yl)-9-anthryl]phenyl}-2-ethyl-1H-benzimidazole (abbreviated as EtBImPBPhA). In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA exhibit very good properties and are therefore preferred choices.

[0152] The host material may be a mixture of multiple substances, and when using a mixed host material, it is preferable to mix an electron-transporting material with a hole-transporting material. By mixing an electron-transporting material with a hole-transporting material, the transport properties of the light-emitting layer 113 can be easily adjusted, and the recombination region can also be easily controlled. The weight ratio of the hole-transporting material to the electron-transporting material is preferably 1:19 to 19:1.

[0153] Furthermore, phosphorescent materials can be used as part of the above-mentioned mixed materials. When a fluorescent material is used as the light-emitting material, the phosphorescent material can be used as an energy donor to supply excitation energy to the fluorescent material.

[0154] Furthermore, these mixed materials may form an excited complex. It is preferable to select a combination that forms an excited complex that exhibits emission overlapping with the wavelength of the lowest-energy absorption band of the luminescent material, as this facilitates smooth energy transfer and efficiently obtains light emission. This configuration is also preferable because it reduces the driving voltage.

[0155] Furthermore, if at least one of the materials forming the excitation complex is a phosphorescent material, the triplet excitation energy can be efficiently converted to singlet excitation energy by reverse intersystem crossing.

[0156] For efficient excitation complex formation, it is preferable that the HOMO level of the hole-transporting material is above the HOMO level of the electron-transporting material. Furthermore, it is preferable that the LUMO level of the hole-transporting material is above the LUMO level of the electron-transporting material. The LUMO and HOMO levels of the materials can be derived from the electrochemical properties (reduction potential and oxidation potential) of the materials measured by cyclic voltammetry (CV).

[0157] 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.

[0158] The electron transport layer 114 is a layer containing an electron-transporting material. The electron-transporting material has an electron mobility of 1 × 10⁻¹⁰ at an electric field strength [V / cm] square root of 600. -7 cm 2 / Vs or more, preferably 1 × 10 -6 cm 2 A substance having an electron mobility of / Vs or higher is preferred. However, any substance that has higher electron transport capacity than holes can be used. As the above organic compound, an organic compound having a π-electron-deficient heteroaromatic ring is preferred. As an organic compound having a π-electron-deficient heteroaromatic ring, it is preferable that it be any or more of the following: an organic compound containing a heteroaromatic ring having an azole skeleton, an organic compound containing a heteroaromatic ring having a pyridine skeleton, an organic compound containing a heteroaromatic ring having a diazine skeleton, and an organic compound containing a heteroaromatic ring having a triazine skeleton.

[0159] As for materials having electron-transporting properties that can be used in the electron transport layer 114, the organic compounds listed as preferred organic compounds having electron-transporting properties for use as a host material in the light-emitting layer 113 can be used in the same way.

[0160] Among the organic compounds listed as preferred electron-transporting organic compounds for use as host materials, organic compounds containing a heteroaromatic ring having a diazine skeleton, or a heteroaromatic ring having a pyridine skeleton, or a heteroaromatic ring having a triazine skeleton are preferred due to their good reliability. In particular, organic compounds containing a heteroaromatic ring having a diazine (pyrimidine or pyrazine) skeleton, or a heteroaromatic ring having a triazine skeleton, exhibit high electron transport properties and contribute to reducing the driving voltage. Organic compounds having a phenanthroline skeleton, such as mTpPPhen, PnNPhen, and mPPhen2P, are especially preferred, and organic compounds having a phenanthroline dimer structure, such as mPPhen2P, are more preferred due to their superior stability.

[0161] Furthermore, the organic compound represented by general formula (G1) or general formula (G2) disclosed in Embodiment 1 can also be suitably used in the electron transport layer 114. By using the organic compound represented by general formula (G1) or general formula (G2) disclosed in Embodiment 1 in the electron transport layer 114, the electron injection performance from the electron injection layer 115 is improved. In addition, the organic compound represented by general formula (G1) or general formula (G2) disclosed in Embodiment 1 has high electron transport properties and contributes to reducing the drive voltage.

[0162] The electron transport layer 114 may have a multilayer structure. Furthermore, the layer in contact with the light-emitting layer 113 in the multilayer electron transport layer 114 may function as a hole-blocking layer. When the electron transport layer in contact with the light-emitting layer functions as a hole-blocking layer, it is preferable to use a material whose HOMO level is 0.5 eV or more lower than the HOMO level of the material contained in the light-emitting layer 113.

[0163] The electron injection layer 115 may be provided by a layer containing alkali metals or alkaline earth metals, compounds or complexes of alkali metals or alkaline earth metals, or 1,1'-pyridine-2,6-diyl-bis(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine) (abbreviation: hpp2Py). The electron injection layer 115 may also be a layer containing these materials within a layer made of an electron-transporting substance.

[0164] Preferably, the electron injection layer 115 contains an organic compound represented by general formula (G1) or general formula (G2) disclosed in Embodiment 1. By including the organic compound represented by general formula (G1) or general formula (G2) disclosed in Embodiment 1, electron injection performance is improved, making it possible to create a light-emitting device with a low driving voltage. Furthermore, the electron injection layer 115 containing the organic compound represented by general formula (G1) or general formula (G2) disclosed in Embodiment 1 can improve the electron donor properties of the metal or metal compound by coordinating with the metal or metal compound. This suppresses the deterioration of the function of the electron injection layer 115 even when exposed to an atmospheric environment, thereby suppressing the rise in driving voltage and making it possible to provide a light-emitting device with good characteristics. In addition, since the electron injection layer using the organic compound represented by general formula (G1) or general formula (G2) has good heat resistance, it is possible to obtain a light-emitting device with good reliability, especially heat resistance.

[0165] In other words, a light-emitting device having an electron injection layer 115 containing an organic compound represented by general formula (G1) or general formula (G2) as disclosed in Embodiment 1 and a metal or metal compound can be manufactured without a significant increase in driving voltage and will be a light-emitting device with good characteristics, even when processed by a photolithography method that includes an air exposure process.

[0166] Alternatively, a charge generation layer 116 can be provided instead of the electron injection layer 115 (Figure 1(B)). The charge generation layer 116 is a layer that can inject holes into the layer in contact with the cathode side and electrons into the layer in contact with the anode side by applying a potential. The charge generation layer 116 includes at least a p-type layer 117. The p-type layer 117 is preferably formed using a composite material listed above as a material that can constitute the hole injection layer 111. The p-type layer 117 may also be formed by laminating a film containing the acceptor material and a film containing the hole transport material as materials constituting the composite material. By applying a potential to the p-type layer 117, electrons are injected into the electron transport layer 114 and holes into the cathode, and the light-emitting device operates. Furthermore, since the organic compound in one embodiment of the present invention is an organic compound with a low refractive index, by using it in the p-type layer 117, a light-emitting device with good external quantum efficiency can be obtained.

[0167] Furthermore, it is preferable that the charge generation layer 116 includes, in addition to the p-type layer 117, one or both of the electron relay layer 118 and the electron injection buffer layer 119.

[0168] The electron relay layer 118 contains at least an electron-transporting material and has the function of preventing interaction between the electron injection buffer layer 119 and the p-type layer 117, thereby smoothly transferring electrons. Preferably, the LUMO level of the electron-transporting material contained in the electron relay layer 118 is located between the LUMO level of the acceptor material in the p-type layer 117 and the LUMO level of the material contained in the layer in contact with the charge generation layer 116 in the electron transport layer 114. The specific energy level of the LUMO level of the electron-transporting material used in the electron relay layer 118 is preferably -5.0 eV or higher, preferably -5.0 eV or higher and -3.0 eV or lower, more preferably -4.30 eV or higher and -3.00 eV or lower, and more preferably -4.30 eV or higher and -3.30 eV or lower, as this suppresses an increase in the driving voltage. Preferably, the electron-transporting material used in the electron relay layer 118 is a phthalocyanine-based material or a metal complex having a metal-oxygen bond and an aromatic ligand.

[0169] Specifically, the electron-transporting material used in the electron relay layer 118 can be diquinoxalino[2,3-a:2',3'-c]phenazine (abbreviated as HATNA), 2,3,8,9,14,15-hexafluorodiquinoxalino[2,3-a:2',3'-c]phenazine (abbreviated as HATNA-F6), perylenetetracarboxylic acid derivatives such as 3,4,9,10-perylenetetracarboxylic acid diimide (abbreviated as PTCDI), and 3,4,9,10-perylenetetracarboxyl-bis-benzimidazole (abbreviated as PTCBI), as well as (C60-Ih)[5,6]fullerene (abbreviated as C60) and (C70-D5h)[5,6]fullerene (abbreviated as C70). Furthermore, compounds having a heterophan skeleton, which is a cyclophane skeleton containing a heterocycle, can be used. Examples of such compounds include phthalocyanine compounds such as phthalocyanine (abbreviated as H2Pc). In addition, metal phthalocyanines containing copper, zinc, cobalt, iron, chromium, nickel, etc., such as copper phthalocyanine (abbreviated as CuPc), zinc phthalocyanine (abbreviated as ZnPc), cobalt phthalocyanine (abbreviated as CoPc), iron phthalocyanine (abbreviated as FePc), tin phthalocyanine (abbreviated as SnPc), tin oxide phthalocyanine (abbreviated as SnOPc), titanium oxide phthalocyanine (abbreviated as TiOPc), and vanadium oxide phthalocyanine (abbreviated as VOPc), and their derivatives can be used. Furthermore, phthalocyanine-based metal complexes, such as copper phthalocyanine or zinc phthalocyanine, or 2,3,8,9,14,15-hexafluorodiquinoxalino[2,3-a:2',3'-c]phenazine are particularly preferred.

[0170] The electron injection buffer layer 119 can use materials with high electron injection potential, such as alkali metals, alkaline earth metals, rare earth metals, and compounds thereof (alkali metal compounds (including oxides such as lithium oxide, halides, and carbonates such as lithium carbonate and cesium carbonate), alkaline earth metal compounds (including oxides, halides, and carbonates), or rare earth metal compounds (including oxides, halides, and carbonates)).

[0171] Furthermore, if the electron injection buffer layer 119 is formed by including an electron-transporting substance and an electron-donating substance, the electron-donating substance can be alkali metals, alkaline earth metals, rare earth metals, and compounds thereof (alkali metal compounds (including oxides such as lithium oxide, halides, and carbonates such as lithium carbonate and cesium carbonate), alkaline earth metal compounds (including oxides, halides, and carbonates), or rare earth metal compounds (including oxides, halides, and carbonates)), as well as organic compounds such as tetratianaphthalene (abbreviated as TTN), nickerosene, and decamethylnickerosene. The electron-transporting substance can be formed using the same materials as those used to constitute the electron transport layer 114 described earlier.

[0172] Furthermore, it is preferable that the electron injection buffer layer 119 contains an organic compound represented by general formula (G1) or general formula (G2) disclosed in Embodiment 1. By including an organic compound represented by general formula (G1) or general formula (G2) disclosed in Embodiment 1, electron injection performance is improved, and a light-emitting device with a low driving voltage can be made possible.

[0173] Furthermore, the electron injection buffer layer 119 containing the organic compound represented by general formula (G1) or general formula (G2) disclosed in Embodiment 1 can improve the electron donor properties of the metal or metal compound by coordinating with the metal or metal compound. This suppresses the impairment of the function of the electron injection buffer layer 119 even when the charge generation layer 116 is exposed to an atmospheric environment, thereby suppressing the rise in driving voltage and providing a light-emitting device with good characteristics.

[0174] In other words, a light-emitting device having a charge generation layer 116 having an electron injection buffer layer 119 containing an organic compound represented by general formula (G1) or general formula (G2) as disclosed in Embodiment 1 and a metal or metal compound can be made into a light-emitting device with good characteristics without a large increase in driving voltage even when processed by a photolithography method that includes an air exposure process.

[0175] Furthermore, since the electron injection buffer layer 119 using the organic compound represented by general formula (G1) or general formula (G2) has good heat resistance, it is possible to obtain a light-emitting device with good reliability, especially heat resistance. Since light-emitting devices processed using photolithography often undergo a heating process to remove moisture, a light-emitting device using the electron injection buffer layer 119 using the organic compound represented by general formula (G1) or general formula (G2) can be made into a light-emitting device that is more suitable for processing by photolithography.

[0176] The second electrode 102 is an electrode that includes a cathode. The second electrode 102 may have a layered structure, in which case the layer in contact with the organic compound layer 103 functions as the cathode. As the material forming the cathode, metals, alloys, electrically conductive compounds, and mixtures thereof with a small work function (specifically 3.8 eV or less) can be used. Specific examples of such cathode materials include alkali metals such as lithium (Li) or cesium (Cs), elements belonging to group 1 or 2 of the periodic table such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys (MgAg, AlLi) and compounds (lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), etc.) containing these, rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these. However, by providing an electron injection layer 115 or a thin film of a material with a low work function between the second electrode 102 and the electron transport layer, various conductive materials such as Al, Ag, ITO, silicon, or indium oxide-tin oxide containing silicon oxide can be used as the cathode, regardless of the magnitude of the work function.

[0177] Furthermore, if the second electrode 102 is formed of a material that is transparent to visible light, it can be made into a light-emitting device that emits light from the second electrode 102 side. Also, if a material with a high refractive index (for example, a material with a normal refractive index (n) at a wavelength of 450 nm) is placed on the second electrode 102, o ) is 1.90 or higher, and the ordinary refractive index (n) at a wavelength of 520 nmo ) is 1.80 or higher, or the ordinary refractive index (n) at a wavelength of 630 nm. o By forming a cap layer with a material having a ratio of 1.75 or higher, the light extraction efficiency can be improved. It is preferable to use an organic compound for the cap layer because it is easy to form.

[0178] These conductive materials can be formed using dry methods such as vacuum deposition or sputtering, inkjet printing, or spin coating. Alternatively, they may be formed using a wet method with a sol-gel process, or using a metal paste.

[0179] Furthermore, various methods can be used to form the organic compound layer 103, regardless of whether they are dry or wet methods. For example, vacuum deposition, gravure printing, offset printing, screen printing, inkjet printing, or spin coating may be used.

[0180] Furthermore, each electrode or layer described above may be formed using different film deposition methods.

[0181] Next, an embodiment of a light-emitting device (also called a stacked element or tandem element) with a configuration in which multiple light-emitting units are stacked will be described with reference to Figure 1(C). This light-emitting device has multiple light-emitting units between the anode and the cathode. Each light-emitting unit has a configuration almost identical to the organic compound layer 103 shown in Figure 1(A). In other words, the light-emitting device shown in Figure 1(C) is a light-emitting device having multiple light-emitting units, while the light-emitting device shown in Figure 1(A) or Figure 1(B) is a light-emitting device having one light-emitting unit.

[0182] In Figure 1(C), a first light-emitting unit 511 and a second light-emitting unit 512 are stacked between the first electrode 501 and the second electrode 502, and an intermediate layer 513 is provided between the first and second light-emitting units 512. The first electrode 501 and the second electrode 502 correspond to the first electrode 101 and the second electrode 102 in Figure 1(A), respectively, and the same explanation as described in the explanation of Figure 1(A) can be applied. Furthermore, the first light-emitting unit 511 and the second light-emitting unit 512 may be made of the same material or different materials.

[0183] The intermediate layer 513 has the function of injecting electrons into one light-emitting unit and holes into the other light-emitting unit when a voltage is applied to the first electrode 501 and the second electrode 502. That is, in Figure 1(C), when a voltage is applied such that the potential of the anode is higher than the potential of the cathode, the intermediate layer 513 should inject electrons into the first light-emitting unit 511 and holes into the second light-emitting unit 512.

[0184] The intermediate layer 513 is preferably formed with the same configuration as the charge generation layer 116 described in Figure 1(B). Because the composite material of organic compounds and metal oxides has excellent carrier implantation and carrier transport properties, it can achieve low-voltage and low-current operation.

[0185] In particular, the electron injection buffer layer 119 in the intermediate layer 513 preferably contains an organic compound represented by general formula (G1) or general formula (G2) disclosed in Embodiment 1. By including an organic compound represented by general formula (G1) or general formula (G2) disclosed in Embodiment 1, electron injection performance is improved, and a light-emitting device with a low driving voltage can be made possible.

[0186] Furthermore, the electron injection buffer layer 119 containing the organic compound represented by general formula (G1) or general formula (G2) disclosed in Embodiment 1 can improve the electron donor properties of the metal or metal compound by coordinating with the metal or metal compound. As a result, even if the organic compound layer 103 is exposed to an atmospheric environment, the function of the electron injection buffer layer 119 in the intermediate layer 513 can be suppressed, thereby suppressing an increase in the driving voltage and providing a light-emitting device with good characteristics.

[0187] In other words, a tandem-type light-emitting device having an intermediate layer 513 with an electron injection buffer layer 119 containing an organic compound represented by general formula (G1) or general formula (G2) as disclosed in Embodiment 1 and a metal or metal compound can be manufactured without a large increase in driving voltage and can be made into a light-emitting device with good characteristics, even when processed by a photolithography method that includes an air exposure process.

[0188] Furthermore, since the electron injection buffer layer 119 using the organic compound represented by general formula (G1) or general formula (G2) has good heat resistance, it is possible to obtain a light-emitting device with good reliability, especially heat resistance. Since light-emitting devices processed using photolithography often undergo a heating process to remove moisture, a light-emitting device using the electron injection buffer layer 119 using the organic compound represented by general formula (G1) or general formula (G2) can be made into a light-emitting device that is more suitable for processing by photolithography.

[0189] Furthermore, if the anode side of the light-emitting unit is in contact with the intermediate layer 513, the intermediate layer 513 can also serve as the hole injection layer of the light-emitting unit, so the light-emitting unit does not need to have a hole injection layer.

[0190] Furthermore, when an electron injection buffer layer 119 is provided in the intermediate layer 513, the electron injection buffer layer 119 plays the role of an electron injection layer in the anode-side light-emitting unit, so it is not necessarily required to form an electron injection layer in the anode-side light-emitting unit.

[0191] Figure 1(C) illustrates a light-emitting device having two light-emitting units, but the same principles can be applied to light-emitting devices with three or more stacked light-emitting units. As in the light-emitting device according to this embodiment, by arranging multiple light-emitting units separated between a pair of electrodes by an intermediate layer 513, high-brightness light emission can be achieved while maintaining a low current density, and a longer-life element can be realized. Furthermore, a light-emitting device that can be driven at a low voltage and consumes little power can be realized.

[0192] Furthermore, by making the emission colors of each light-emitting unit different, the light-emitting device as a whole can emit light of a desired hue. For example, in a light-emitting device having two light-emitting units, it is possible to obtain a light-emitting device that emits white light as a whole by obtaining red and green hues from the first light-emitting unit and blue hues from the second light-emitting unit. In addition, by having the light-emitting central material of each light-emitting unit exhibit the same hue of emission color, it is possible to provide a light-emitting device with extremely high current efficiency.

[0193] Furthermore, each layer, such as the organic compound layer 103, the first light-emitting unit 511, the second light-emitting unit 512, and the charge generation layer, as well as the electrodes, can be formed using methods such as vapor deposition (including vacuum deposition), droplet ejection (also known as inkjet printing), coating, and gravure printing. They may also contain low-molecular-weight materials, medium-molecular-weight materials (including oligomers and dendrimers), or polymer materials.

[0194] (Embodiment 3) In this embodiment, a display device manufactured using the light-emitting device described in Embodiment 2 will be explained with reference to Figure 2. Figure 2(A) is a top view showing the display device, and Figure 2(B) is a cross-sectional view obtained by cutting Figure 2(A) along A and C. This display 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.

[0195] 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 term "display device" includes not only the display device itself, but also the state in which the FPC or PWB is attached to it.

[0196] Next, the cross-sectional structure will be explained using Figure 2(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.

[0197] 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.

[0198] The structure of the transistors used in the pixels and driving circuits is not particularly limited. For example, they may be inverse staggered transistors or staggered transistors. They may also be top-gate or bottom-gate transistors. The semiconductor material used for the transistors 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.

[0199] 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.

[0200] Here, it is preferable to use oxide semiconductors for semiconductor devices such as transistors used in the pixels and 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.

[0201] 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).

[0202] 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.

[0203] By using such materials as semiconductor layers, fluctuations in electrical properties can be suppressed, enabling the realization of highly reliable transistors.

[0204] 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 each 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.

[0205] 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.

[0206] Note that FET623 is one of the transistors formed in the drive circuit section 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.

[0207] 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.

[0208] 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.

[0209] Furthermore, in order to ensure good coverage of the organic compound layer 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 to 3 μm) 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.

[0210] An organic compound 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 films, silicon-containing indium tin oxide films, indium oxide films containing 2-20 wt% zinc oxide, titanium nitride films, chromium films, tungsten films, Zn films, and Pt films, a laminate of a titanium nitride film and a film mainly composed of aluminum, or a three-layer structure of a titanium nitride film, a film mainly composed of aluminum, and a titanium nitride film 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.

[0211] Furthermore, the organic compound layer 616 is formed by various methods such as vapor deposition using a vapor deposition mask, inkjet printing, and spin coating. The organic compound layer 616 includes the configuration described in Embodiment 2. Other materials constituting the organic compound layer 616 may be low molecular weight compounds or high molecular weight compounds (including oligomers and dendrimers).

[0212] Furthermore, it is preferable to use a material with a low work function (such as Al, Mg, Li, Ca, or alloys and compounds thereof (MgAg, MgIn, AlLi, etc.)) for the second electrode 617, which is formed on the organic compound layer 616 and functions as a cathode. If the light generated in the organic compound 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 2-20 wt% zinc oxide, indium tin oxide containing silicon, zinc oxide (ZnO), etc.) as the second electrode 617.

[0213] A light-emitting device is formed by the first electrode 613, the organic compound layer 616, and the second electrode 617. This light-emitting device is the light-emitting device described in Embodiment 2. Although the pixel portion is made up of multiple light-emitting devices, in the display device of this embodiment, both the light-emitting device described in Embodiment 2 and light-emitting devices having other configurations may be mixed together.

[0214] 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 (nitrogen, argon, etc.) or a sealing material. A recess is formed in the sealing substrate, and a desiccant is placed therein to suppress deterioration due to moisture, which is a preferred configuration.

[0215] Furthermore, epoxy resin and glass frit are preferably used 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 and 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.

[0216] Although not shown in FIG. 2, a cap layer and / or a protective film may be provided on the second electrode. By forming the cap layer, the light extraction efficiency can be improved. The cap layer is preferably formed using a material having a normal light refractive index (no) of 1.90 or more at a wavelength of 450 nm, a normal light refractive index (no) of 1.80 or more at a wavelength of 520 nm, or a normal light refractive index (no) of 1.75 or more at a wavelength of 630 nm. Further, the cap layer is preferably formed by depositing an organic compound by vapor deposition because it can be easily formed.

[0217] The protective film may be formed of an organic resin film or an inorganic insulating film. In particular, it is preferable to use a material that can be formed by the atomic layer deposition (ALD) method for the protective film. By using the ALD method, a protective film that is dense, has reduced defects such as cracks and pinholes, or has a uniform thickness can be formed. Further, the damage to the processing member when forming the protective film can be reduced.

[0218] Further, a protective film may be formed so as to cover the exposed portion of the sealing material 605. Further, the protective film can be provided to cover the exposed side surfaces of the surfaces and side surfaces of the pair of substrates, the sealing layer, the insulating layer, etc.

[0219] A material that is difficult for impurities such as water to permeate can be used for the protective film. Therefore, it is possible to effectively suppress the diffusion of impurities such as water from the outside to the inside.

[0220] The protective film can be made from materials such as 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 are available. Materials containing aluminum nitride, hafnium nitride, silicon nitride, tantalum nitride, titanium nitride, niobium nitride, molybdenum nitride, zirconium nitride, or gallium nitride are also available. 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 are also available. Aluminum oxide is particularly preferred as a protective film.

[0221] It is preferable to form the protective film using a film deposition method that provides good step coverage. One such method is the ALD method. For example, by forming the protective film using the ALD method, a uniform protective film with few defects can be formed even on surfaces with complex uneven shapes, such as the top, sides, and back surfaces of a touch panel.

[0222] As described above, a display device manufactured using the light-emitting device described in Embodiment 2 can be obtained.

[0223] Since the display device in this embodiment uses the light-emitting device described in Embodiment 2, a display device with good characteristics can be obtained. Specifically, because the light-emitting device described in Embodiment 2 has a low driving voltage, it is possible to make a display device with low power consumption. In addition, since the light-emitting device described in Embodiment 2 has good reliability, a highly reliable display device can be made. Furthermore, the light-emitting device described in Embodiment 2 can be made into a light-emitting device with good display quality.

[0224] Furthermore, this embodiment can be freely combined with other embodiments.

[0225] (Embodiment 4) As illustrated in Figures 3(A) and 3(B), multiple light-emitting devices 130 are formed on the insulating layer 175 to constitute a display device. In this embodiment, another aspect of the display device of the present invention will be described in detail.

[0226] The display device 100 has a pixel section 177 in which a plurality of pixels 178 are arranged in a matrix. The pixels 178 include sub-pixels 110R, sub-pixels 110G, and sub-pixels 110B.

[0227] In this specification, for example, when describing matters common to sub-pixels 110R, 110G, and 110B, they may be referred to simply as sub-pixel 110. Similarly, when describing matters common to other components distinguished by letters, the letters may be omitted and the corresponding symbols used.

[0228] Sub-pixel 110R emits red light, sub-pixel 110G emits green light, and sub-pixel 110B emits blue light. This allows an image to be displayed on the pixel section 177. In this embodiment, three sub-pixels of red (R), green (G), and blue (B) are used as an example, but other combinations of sub-pixels of other colors may be used. Furthermore, the number of sub-pixels is not limited to three, but may be four or more. Examples of four sub-pixels include four sub-pixels of R, G, B, and white (W), four sub-pixels of R, G, B, and Y, and four sub-pixels of R, G, B, and infrared (IR).

[0229] In this specification and other documents, the row direction is sometimes referred to as the X direction, and the column direction as the Y direction. The X and Y directions intersect, for example, perpendicularly.

[0230] Figure 3(A) shows an example where subpixels of different colors are arranged in the X direction, and subpixels of the same color are arranged in the Y direction. Alternatively, subpixels of different colors may be arranged in the Y direction, and subpixels of the same color may be arranged in the X direction.

[0231] A connecting portion 140 and a region 141 may be provided on the outside of the pixel portion 177. If region 141 is provided, it is located between the pixel portion 177 and the connecting portion 140. If region 141 is provided, an organic compound layer is provided in region 141. In addition, a conductive layer 151C is provided in the connecting portion 140.

[0232] Figure 3(A) shows an example where region 141 and connection portion 140 are located to the right of the pixel portion 177, but the positions of region 141 and connection portion 140 are not particularly limited. Also, region 141 and connection portion 140 may be singular or plural.

[0233] Figure 3(B) is an example of a cross-sectional view between the dashed-dotted line A1-A2 in Figure 3(A). As shown in Figure 3(B), the display device 100 has an insulating layer 171, a conductive layer 172 on the insulating layer 171, an insulating layer 173 on the insulating layer 171 and on the conductive layer 172, an insulating layer 174 on the insulating layer 173, and an insulating layer 175 on the insulating layer 174. The insulating layer 171 is provided on a substrate (not shown). The insulating layer 175, insulating layer 174, and insulating layer 173 are provided with openings that reach the conductive layer 172, and plugs 176 are provided to fill these openings.

[0234] In the pixel section 177, a light-emitting device 130 is provided on an insulating layer 175 and a plug 176. A protective layer 131 is provided so as to cover the light-emitting device 130. A substrate 120 is bonded to the protective layer 131 by a resin layer 122. Preferably, an inorganic insulating layer 125 and an insulating layer 127 on the inorganic insulating layer 125 are provided between adjacent light-emitting devices 130.

[0235] In Figure 3(B), multiple cross-sections of the inorganic insulating layer 125 and the insulating layer 127 are shown, but when the display device 100 is viewed from above, it is preferable that the inorganic insulating layer 125 and the insulating layer 127 are connected as a single unit.

[0236] Figure 3(B) shows light-emitting devices 130R, 130G, and 130B as light-emitting devices 130. Light-emitting devices 130R, 130G, and 130B are assumed to emit different colors from each other. For example, light-emitting device 130R can emit red light, light-emitting device 130G can emit green light, and light-emitting device 130B can emit blue light. In addition, light-emitting devices 130R, 130G, or 130B may emit other visible light or infrared light.

[0237] One embodiment of the present invention can be a top-emission type, for example, which emits light in the opposite direction to the substrate on which the light-emitting device is formed. Alternatively, one embodiment of the present invention may be a bottom-emission type.

[0238] The light-emitting device 130R includes a first electrode 101R (pixel electrode) consisting of a conductive layer 151R and a conductive layer 152R, an organic compound layer 103R on the first electrode 101R, a common layer 104 on the organic compound layer 103R, and a second electrode (common electrode) 102 on the common layer 104. The common layer 104 may or may not be provided, but its provision is preferable because it reduces damage to the organic compound layer 103R during processing.

[0239] The light-emitting device 130G includes a first electrode 101G (pixel electrode) composed of a conductive layer 151G and a conductive layer 152G, an organic compound layer 103G on the first electrode 101G, a common layer 104 on the organic compound layer 103G, and a second electrode (common electrode) 102 on the common layer 104. The common layer 104 may or may not be provided, but it is preferably provided because it can reduce damage to the organic compound layer 103G during processing.

[0240] The light-emitting device 130B has a configuration as shown in Embodiment 2. It includes a first electrode 101B (pixel electrode) composed of a conductive layer 151B and a conductive layer 152B, an organic compound layer 103B on the first electrode 101B, a common layer 104 on the organic compound layer 103B, and a second electrode (common electrode) 102 on the common layer 104. The common layer 104 may or may not be provided, but it is preferably provided because it can reduce damage to the organic compound layer 103B during processing. When the common layer 104 is provided, the laminated structure of the organic compound layer 103B and the common layer 104 corresponds to the organic compound layer 103 in Embodiment 2. When the common layer 104 is not provided, the first layer 135 corresponds to the organic compound layer 103.

[0241] The common layer 104 is preferably an electron injection layer or an electron transport layer, and more preferably an electron injection layer. When it is an electron transport layer, the electron transport layer preferably has a laminated structure, and among the laminated layers, the layer on the second electrode side is the common layer 104 and the layer on the light-emitting layer side is the organic compound layer 103.

[0242] Also, since the light-emitting devices 130R and 130G are also light-emitting devices manufactured through a photolithography process, a light-emitting device with a low driving voltage can be obtained in which the increase in the driving voltage due to the photolithography process is suppressed.

[0243] Of the pixel electrodes and common electrodes of the light-emitting device 130, one functions as the anode and the other as the cathode. In the following explanation, unless otherwise specified, the pixel electrodes function as the anode and the common electrodes function as the cathode.

[0244] The organic compound layers 103R, 103G, and 103B are independently arranged in island-like formations for each light-emitting device or for each light-emitting color. By providing the organic compound layer 103 in island-like formations for each light-emitting device 130, leakage current between adjacent light-emitting devices 130 can be suppressed even in high-definition display devices. This prevents crosstalk and enables the realization of a display device with extremely high contrast. In particular, it enables the realization of a display device with high current efficiency at low brightness.

[0245] The island-like organic compound layers 103 are formed by depositing an organic compound film and then processing the organic compound film using photolithography.

[0246] Preferably, the organic compound layer 103 is provided so as to cover the top and side surfaces of the first electrode (pixel electrode) of the light-emitting device 130. This makes it easier to increase the aperture ratio of the display device 100 compared to a configuration where the edges of the organic compound layer 103 are located inward from the edges of the pixel electrode. Furthermore, by covering the side surfaces of the pixel electrode of the light-emitting device 130 with the organic compound layer 103, contact between the pixel electrode and the second electrode 102 can be suppressed, thereby suppressing short circuits in the light-emitting device 130.

[0247] Furthermore, in a display device according to one aspect of the present invention, it is preferable that the first electrode (pixel electrode) of the light-emitting device be in a stacked configuration. For example, in the example shown in Figure 3(B), the first electrode of the light-emitting device 130 is in a stacked configuration of a conductive layer 151 and a conductive layer 152.

[0248] For example, a metallic material can be used as the conductive layer 151. Specifically, metals such as aluminum (Al), titanium (Ti), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), gallium (Ga), zinc (Zn), indium (In), tin (Sn), molybdenum (Mo), tantalum (Ta), tungsten (W), palladium (Pd), gold (Au), platinum (Pt), silver (Ag), yttrium (Y), neodymium (Nd), and alloys containing these in appropriate combinations can also be used.

[0249] As the conductive layer 152, an oxide having one or more selected from indium, tin, zinc, gallium, titanium, aluminum, and silicon can be used. For example, it is preferable to use a conductive oxide containing one or more of the following: indium oxide, indium tin oxide, indium zinc oxide, zinc oxide, zinc oxide containing gallium, titanium oxide, indium zinc oxide containing gallium, indium zinc oxide containing aluminum, indium tin oxide containing silicon, and indium zinc oxide containing silicon. In particular, indium tin oxide containing silicon has a large work function, for example, a work function of 4.0 eV or more, so it can be suitably used as the conductive layer 152.

[0250] The conductive layer 151 may be a laminated structure of multiple layers having different materials, and the conductive layer 152 may be a laminated structure of multiple layers having different materials. In this case, the conductive layer 151 may have a layer made of a material that can be used for the conductive layer 152, such as a conductive oxide, and the conductive layer 152 may have a layer made of a material that can be used for the conductive layer 151, such as a metallic material. For example, if the conductive layer 151 has a laminated structure of two or more layers, the layer in contact with the conductive layer 152 may be a layer made of a material that can be used for the conductive layer 152.

[0251] Furthermore, it is preferable that the side surface of the conductive layer 151 has a tapered shape. Specifically, it is preferable that the side surface of the conductive layer 151 has a tapered shape with a taper angle of less than 90°. In this case, the conductive layer 152 provided along the side surface of the conductive layer 151 also has a tapered shape. By making the side surface of the conductive layer 152 tapered, the coverage of the organic compound layer 103 provided along the side surface of the conductive layer 152 can be improved.

[0252] Next, an example of a method for manufacturing a display device 100 having the configuration shown in Figure 3(A) will be explained using Figures 4 to 9.

[0253] [Example of manufacturing method 1] Thin films (insulating films, semiconductor films, conductive films, etc.) that constitute a display device can be formed using sputtering, chemical vapor deposition (CVD), vacuum deposition, pulsed laser deposition (PLD), or ALD.

[0254] Furthermore, thin films (insulating films, semiconductor films, conductive films, etc.) that constitute the display device can be formed by wet film deposition methods such as spin coating, dip coating, spray coating, inkjet printing, dispensing, screen printing, offset printing, doctor knife method, slit coating, roll coating, curtain coating, or knife coating.

[0255] Furthermore, when processing the thin films that make up the display device, the processing can be done using methods such as photolithography.

[0256] In photolithography, the light used for exposure can be, for example, i-line (wavelength 365 nm), g-line (wavelength 436 nm), h-line (wavelength 405 nm), or a mixture thereof. Other light sources such as ultraviolet light, KrF laser light, or ArF laser light can also be used. Exposure may also be performed using immersion lithography. Furthermore, extreme ultraviolet (EUV) light or X-rays may be used as the light source for exposure. An electron beam can also be used instead of the light source for exposure.

[0257] For etching thin films, dry etching, wet etching, or sandblasting methods can be used.

[0258] First, as shown in Figure 4(A), an insulating layer 171 is formed on a substrate (not shown). Next, a conductive layer 172 and a conductive layer 179 are formed on the insulating layer 171, and an insulating layer 173 is formed on the insulating layer 171 so as to cover the conductive layers 172 and 179. Next, an insulating layer 174 is formed on the insulating layer 173, and an insulating layer 175 is formed on the insulating layer 174.

[0259] As the substrate, a substrate with at least sufficient heat resistance to withstand subsequent heat treatment can be used. For example, glass substrates, quartz substrates, sapphire substrates, ceramic substrates, or organic resin substrates, single-crystal semiconductor substrates made of silicon or silicon carbide, polycrystalline semiconductor substrates, compound semiconductor substrates such as silicon germanium, and SOI substrates can be used.

[0260] Next, as shown in Figure 4(A), openings reaching the conductive layer 172 are formed in the insulating layer 175, insulating layer 174, and insulating layer 173. Subsequently, a plug 176 is formed to fill these openings.

[0261] Next, as shown in Figure 4(A), conductive films 151f, 152R, 152G, 152B, and 152C are formed on the plug 176 and the insulating layer 175, respectively. For example, a metallic material can be used as the conductive film 151f. For example, an oxide having one or more selected from indium, tin, zinc, gallium, titanium, aluminum, and silicon can be used as the conductive film 152f.

[0262] Next, as shown in Figure 4(A), a resist mask 191 is formed on the conductive film 152f. The resist mask 191 can be formed by applying a photosensitive material (photoresist), followed by exposure and development.

[0263] Next, as shown in Figure 4(B), conductive films 151f and 152f in areas that do not overlap with the resist mask 191 are removed. This forms conductive layers 151 and 152.

[0264] Next, as shown in Figure 4(C), the resist mask 191 is removed. The resist mask 191 can be removed, for example, by ashing using oxygen plasma.

[0265] Next, as shown in Figure 4(D), insulating film 156f, which will later become insulating layer 156R, insulating layer 156G, insulating layer 156B, and insulating layer 156C, is formed on conductive layer 152R, conductive layer 152G, conductive layer 152B, conductive layer 152C, and insulating layer 175.

[0266] The insulating film 156f can be an inorganic insulating film such as an oxide insulating film, a nitride insulating film, an oxidative nitride insulating film, or a nitride oxide insulating film, for example, silicon oxidative nitride.

[0267] Next, as shown in Figure 4(E), insulating layer 156R, insulating layer 156G, insulating layer 156B, and insulating layer 156C are formed by processing the insulating film 156f.

[0268] Next, as shown in Figure 5(A), the organic compound film 103Rf is formed on the conductive layer 152R, the conductive layer 152G, the conductive layer 152B, and the insulating layer 175. Note that, as shown in Figure 5(A), the organic compound film 103Rf is not formed on the conductive layer 152C.

[0269] Next, as shown in Figure 5(A), a sacrificial film 158Rf and a mask film 159Rf are formed.

[0270] By providing a sacrificial film 158Rf on the organic compound film 103Rf, the damage sustained by the organic compound film 103Rf during the manufacturing process of the display device can be reduced, thereby improving the reliability of the light-emitting device.

[0271] For the sacrificial film 158Rf, a film with high resistance to the processing conditions of the organic compound film 103Rf is used, specifically a film with a high etching selectivity ratio with the organic compound film 103Rf. For the mask film 159Rf, a film with a high etching selectivity ratio with the sacrificial film 158Rf is used.

[0272] Furthermore, the sacrificial film 158Rf and the mask film 159Rf are formed at a temperature lower than the heat resistance temperature of the organic compound film 103Rf. The substrate temperature when forming the sacrificial film 158Rf and the mask film 159Rf is typically 100°C to 200°C, preferably 100°C to 150°C, and more preferably 100°C to 120°C. Since the light-emitting device according to one aspect of the present invention contains an organic compound represented by general formula (G1) or general formula (G2), it is possible to provide a display device with good display quality even after undergoing a heating process at a higher temperature.

[0273] It is preferable to use films that can be removed by wet etching or dry etching for the sacrificial film 158Rf and the mask film 159Rf.

[0274] Furthermore, it is preferable that the sacrificial film 158Rf, which is formed in contact with the organic compound film 103Rf, is formed using a method that causes less damage to the organic compound film 103Rf than the mask film 159Rf. For example, ALD (Atomic Layer Deposition) or vacuum deposition is preferred over sputtering.

[0275] The sacrificial film 158Rf and the mask film 159Rf can be one or more of the following, for example, metal films, alloy films, metal oxide films, semiconductor films, organic insulating films, and inorganic insulating films.

[0276] The sacrificial film 158Rf and the mask film 159Rf can be made of metallic materials such as gold, silver, platinum, magnesium, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, palladium, titanium, aluminum, yttrium, zirconium, and tantalum, or alloy materials containing such metallic materials. In particular, it is preferable to use low-melting-point materials such as aluminum or silver. It is preferable to use a metallic material capable of shielding ultraviolet rays for one or both of the sacrificial film 158Rf and the mask film 159Rf, as this can suppress the irradiation of the organic compound film 103Rf with ultraviolet rays during pattern exposure and suppress the degradation of the organic compound film 103Rf.

[0277] Furthermore, the sacrificial film 158Rf and the mask film 159Rf can be made from metal oxides such as In-Ga-Zn oxide, indium oxide, In-Zn oxide, In-Sn oxide, indium titanium oxide (In-Ti oxide), indium tin zinc oxide (In-Sn-Zn oxide), indium titanium zinc oxide (In-Ti-Zn oxide), indium gallium tin zinc oxide (In-Ga-Sn-Zn oxide), and silicon-containing indium tin oxide, respectively.

[0278] Furthermore, in the above metal oxide, element M (where M is one or more selected from aluminum, silicon, boron, yttrium, copper, vanadium, beryllium, titanium, iron, nickel, germanium, zirconium, molybdenum, lanthanum, cerium, neodymium, hafnium, tantalum, tungsten, or magnesium) may be used instead of gallium.

[0279] For the sacrificial film 158Rf and mask film 159Rf, it is preferable to use semiconductor materials such as silicon or germanium, for example, because they have high compatibility with semiconductor manufacturing processes. Alternatively, compounds containing the above semiconductor materials can be used.

[0280] Furthermore, various inorganic insulating films can be used as the sacrificial film 158Rf and the mask film 159Rf, respectively. In particular, oxide insulating films are preferred because they have higher adhesion to the organic compound film 103Rf compared to nitride insulating films.

[0281] Next, as shown in Figure 5(A), a resist mask 190R is formed. The resist mask 190R can be formed by applying a photosensitive material (photoresist), followed by exposure and development.

[0282] The resist mask 190R is provided in a position that overlaps with the conductive layer 152R. Preferably, the resist mask 190R is also provided in a position that overlaps with the conductive layer 152C. This helps to suppress damage to the conductive layer 152C during the manufacturing process of the display device.

[0283] Next, as shown in Figure 5(B), a portion of the mask film 159Rf is removed using the resist mask 190R to form a mask layer 159R. The mask layer 159R remains on the conductive layer 152R and the conductive layer 152C. After that, the resist mask 190R is removed. Subsequently, the mask layer 159R is used as a mask (also called a hard mask) to remove a portion of the sacrificial film 158Rf to form a sacrificial layer 158R.

[0284] By using the wet etching method, the damage to the organic compound film 103Rf during processing of the sacrificial film 158Rf and the mask film 159Rf can be reduced compared to using the dry etching method. When using the wet etching method, it is preferable to use an acidic aqueous solution such as a developer, an alkaline aqueous solution such as an aqueous solution of tetramethylammonium hydroxide (TMAH), dilute hydrofluoric acid, oxalic acid, phosphoric acid, acetic acid, nitric acid, or a chemical solution using a mixture thereof.

[0285] Furthermore, when using a dry etching method for processing the sacrificial film 158Rf, the degradation of the organic compound film 103Rf can be suppressed by not using an oxygen-containing gas as the etching gas.

[0286] Resist mask 190R can be removed in the same manner as resist mask 191.

[0287] Next, as shown in Figure 5(B), the organic compound film 103Rf is processed to form the organic compound layer 103R. For example, the mask layer 159R and the sacrificial layer 158R are used as a hard mask to remove a portion of the organic compound film 103Rf and form the organic compound layer 103R.

[0288] As a result, as shown in Figure 5(B), the laminated structure of the organic compound layer 103R, the sacrificial layer 158R, and the mask layer 159R remains on the conductive layer 152R. The conductive layers 152G and 152B are exposed.

[0289] The organic compound film 103Rf is preferably processed by anisotropic etching. In particular, anisotropic dry etching is preferred. Alternatively, wet etching may be used.

[0290] When using the dry etching method, the degradation of the organic compound film 103Rf can be suppressed by not using an oxygen-containing gas as the etching gas.

[0291] Furthermore, an etching gas containing oxygen may be used. Including oxygen in the etching gas can increase the etching rate. Therefore, etching can be performed under low power conditions while maintaining a sufficiently fast etching rate. This suppresses damage to the organic compound film 103Rf. In addition, it suppresses problems such as the adhesion of reaction products generated during etching.

[0292] When using the dry etching method, it is preferable to use a gas containing one or more of the Group 18 elements, such as H2, CF4, C4F8, SF6, CHF3, Cl2, H2O, BCl3, or He, Ar, as the etching gas. Alternatively, it is preferable to use a gas containing one or more of these elements and oxygen as the etching gas. Alternatively, oxygen gas may be used as the etching gas.

[0293] Next, as shown in Figure 6(A), an organic compound film 103Gf, which will later become the organic compound layer 103G, is formed.

[0294] The organic compound film 103Gf can be formed by the same method as that used to form the organic compound film 103Rf. Furthermore, the organic compound film 103Gf can have the same structure as the organic compound film 103Rf.

[0295] Next, as shown in Figure 6(A), a sacrificial film 158Gf and a mask film 159Gf are formed in sequence. After that, a resist mask 190G is formed. The materials and formation methods for the sacrificial film 158Gf and mask film 159Gf are the same as those applicable to the sacrificial film 158Rf and mask film 159Rf. The materials and formation methods for the resist mask 190G are the same as those applicable to the resist mask 190R.

[0296] The resist mask 190G is placed in a position that overlaps with the conductive layer 152G.

[0297] Next, as shown in Figure 6(B), a portion of the mask film 159Gf is removed using the resist mask 190G to form a mask layer 159G. The mask layer 159G remains on the conductive layer 152G. After that, the resist mask 190G is removed. Next, the mask layer 159G is used as a mask to remove a portion of the sacrificial film 158Gf to form a sacrificial layer 158G. Subsequently, the organic compound film 103Gf is processed to form an organic compound layer 103G.

[0298] Next, as shown in Figure 6(C), an organic compound film 103Bf is formed.

[0299] The organic compound film 103Bf can be formed by the same method as that used to form the organic compound film 103Rf. Furthermore, the organic compound film 103Bf can have the same structure as the organic compound film 103Rf.

[0300] Next, as shown in Figure 6(C), the sacrificial film 158Bf and the mask film 159Bf are formed in sequence. After that, the resist mask 190B is formed. The materials and formation methods for the sacrificial film 158Bf and the mask film 159Bf are the same as those applicable to the sacrificial film 158Rf and the mask film 159Rf. The materials and formation methods for the resist mask 190B are the same as those applicable to the resist mask 190R.

[0301] The resist mask 190B is placed in a position that overlaps with the conductive layer 152B.

[0302] Next, as shown in Figure 6(D), a portion of the mask film 159Bf is removed using the resist mask 190B to form the mask layer 159B. The mask layer 159B remains on the conductive layer 152B. After that, the resist mask 190B is removed. Next, the mask layer 159B is used as a mask to remove a portion of the sacrificial film 158Bf to form the sacrificial layer 158B. Next, the organic compound film 103Bf is processed to form the organic compound layer 103B. For example, the mask layer 159B and the sacrificial layer 158B are used as a hard mask to remove a portion of the organic compound film 103Bf to form the organic compound layer 103B.

[0303] As a result, as shown in Figure 6(D), the laminated structure of the organic compound layer 103B, the sacrificial layer 158B, and the mask layer 159B remains on the conductive layer 152B. In addition, the mask layers 159R and 159G are exposed.

[0304] Furthermore, it is preferable that the sides of the organic compound layer 103R, organic compound layer 103G, and organic compound layer 103B are perpendicular or approximately perpendicular to the surface to be formed. For example, it is preferable that the angle between the surface to be formed and these sides be 60 degrees or more and 90 degrees or less.

[0305] As described above, the distance between two adjacent organic compound layers 103R, 103G, and 103B formed using photolithography can be narrowed to 8 μm or less, 5 μm or less, 3 μm or less, 2 μm or less, or 1 μm or less. Here, this distance can be defined, for example, by the distance between two adjacent opposing ends of organic compound layers 103R, 103G, and 103B. By narrowing the distance between the island-like organic compound layers in this way, a display device with high resolution and a large aperture ratio can be provided. Furthermore, the distance between the first electrodes between adjacent light-emitting devices can also be narrowed, for example, to 10 μm or less, 8 μm or less, 5 μm or less, 3 μm or less, or 2 μm or less. It is preferable that the distance between the first electrodes between adjacent light-emitting devices is 2 μm or more and 5 μm or less.

[0306] Next, as shown in Figure 7(A), it is preferable to remove the mask layer 159R, mask layer 159G, and mask layer 159B.

[0307] The same method as the mask film processing method can be used for the mask layer removal process. In particular, by using a wet etching method, the damage to the organic compound layer 103 during mask layer removal can be reduced compared to when using a dry etching method.

[0308] Alternatively, the mask layer may be removed by dissolving it in a polar solvent such as water or alcohol. Examples of alcohols include ethyl alcohol, methyl alcohol, isopropyl alcohol (IPA), or glycerin.

[0309] After removing the mask layer, a drying treatment may be performed to remove water adsorbed on the surface. For example, a heat treatment can be performed in an inert gas atmosphere or a reduced pressure atmosphere. The heat treatment can be performed at a substrate temperature of 50°C to 200°C, preferably 60°C to 150°C, and more preferably 70°C to 120°C. A reduced pressure atmosphere is preferable because it allows drying at a lower temperature.

[0310] Next, as shown in Figure 7(B), an inorganic insulating film 125f is formed.

[0311] Next, as shown in Figure 7(C), an insulating film 127f, which will later become the insulating layer 127, is formed on the inorganic insulating film 125f.

[0312] The substrate temperature when forming the inorganic insulating film 125f and insulating film 127f is preferably 60°C or higher, 80°C or higher, 100°C or higher, or 120°C or higher, and 200°C or lower, 180°C or lower, 160°C or lower, 150°C or lower, or 140°C or lower, respectively.

[0313] As the inorganic insulating film 125f, it is preferable to form an insulating film with a thickness of 3 nm or more, 5 nm or more, or 10 nm or more, and 200 nm or less, 150 nm or less, 100 nm or less, or 50 nm or less, within the above substrate temperature range.

[0314] The inorganic insulating film 125f is preferably formed using, for example, the ALD method. The ALD method is preferable because it can reduce film formation damage and allow for the formation of a highly covering film. For example, it is preferable to form an aluminum oxide film as the inorganic insulating film 125f using the ALD method.

[0315] The insulating film 127f is preferably formed using the wet film formation method described above. The insulating film 127f is preferably formed using a photosensitive material, for example, by spin coating, and more specifically, it is preferably formed using a photosensitive resin composition containing an acrylic resin.

[0316] Next, exposure is performed to expose a portion of the insulating film 127f to visible light or ultraviolet light. The insulating layer 127 is formed in the region sandwiched between any two of the conductive layers 152R, 152G, and 152B, and around the conductive layer 152C.

[0317] The width of the insulating layer 127 to be formed later can be controlled by the exposure area of ​​the insulating film 127f. In this embodiment, the insulating layer 127 is processed so that it has a portion that overlaps with the upper surface of the conductive layer 151.

[0318] The light used for exposure preferably includes the i-line (wavelength 365 nm). Furthermore, the light used for exposure may also include at least one of the g-line (wavelength 436 nm) and the h-line (wavelength 405 nm).

[0319] Next, as shown in Figure 8(A), development is performed to remove the exposed area of ​​the insulating film 127f and form the insulating layer 127a.

[0320] Next, as shown in Figure 8(B), etching is performed using the insulating layer 127a as a mask to remove a portion of the inorganic insulating film 125f and thin the film thickness of parts of the sacrificial layer 158R, sacrificial layer 158G, and sacrificial layer 158B. As a result, the inorganic insulating layer 125 is formed beneath the insulating layer 127a. In addition, the surfaces of the thinned portions of the sacrificial layer 158R, sacrificial layer 158G, and sacrificial layer 158B are exposed. In the following, the etching process using the insulating layer 127a as a mask may be referred to as the first etching process.

[0321] The first etching process can be carried out by dry etching or wet etching. It is preferable that the inorganic insulating film 125f is deposited using the same material as the sacrificial layer 158R, sacrificial layer 158G, and sacrificial layer 158B, as this allows the first etching process to be performed in a single step.

[0322] When performing dry etching, it is preferable to use a chlorine-based gas. As chlorine-based gases, Cl2, BCl3, SiCl4, and CCl4 can be used individually or in mixtures of two or more gases. In addition, oxygen gas, hydrogen gas, helium gas, and argon gas can be added to the above chlorine-based gases individually or in mixtures of two or more gases as appropriate. By using dry etching, regions with thin film thickness in sacrificial layers 158R, 158G, and 158B can be formed with good in-plane uniformity.

[0323] As the dry etching apparatus, a dry etching apparatus having a high-density plasma source can be used. A dry etching apparatus having a high-density plasma source can be, for example, an inductively coupled plasma (ICP) etching apparatus. Alternatively, a capacitively coupled plasma (CCP) etching apparatus having parallel plate electrodes can be used.

[0324] Furthermore, it is preferable to perform the first etching process by wet etching. By using the wet etching method, damage to the organic compound layer 103R, organic compound layer 103G, and organic compound layer 103B can be reduced compared to when the dry etching method is used. For example, wet etching can be performed using an alkaline solution. For example, TMAH, an alkaline solution, can be used for wet etching of an aluminum oxide film. Alternatively, an acid solution containing fluoride can be used. In this case, wet etching can be performed using a paddle method. It is preferable that the inorganic insulating film 125f is deposited using the same material as the sacrificial layer 158R, sacrificial layer 158G, and sacrificial layer 158B, as the above etching process can be performed in a single step.

[0325] In the first etching process, the sacrificial layers 158R, 158G, and 158B are not completely removed, and the etching process is stopped when the film thickness is reduced. By leaving the corresponding sacrificial layers 158R, 158G, and 158B on the organic compound layers 103R, 103G, and 103B in this manner, it is possible to prevent damage to the organic compound layers 103R, 103G, and 103B in subsequent processing steps.

[0326] Next, it is preferable to expose the entire substrate to visible light or ultraviolet light and irradiate the insulating layer 127a. The energy density of this exposure is 0 mJ / cm². 2 Even larger, 800 mJ / cm 2 The following is preferable: 0 mJ / cm 2 Larger, 500 mJ / cm 2 The following is more preferable: Performing such exposure after development may improve the transparency of the insulating layer 127a. In addition, it may be possible to lower the substrate temperature required for the heat treatment in a later process to deform the insulating layer 127a into a tapered shape.

[0327] Here, the presence of oxygen barrier insulating layers (e.g., an aluminum oxide film) as sacrificial layers 158R, 158G, and 158B reduces the diffusion of oxygen into organic compound layers 103R, 103G, and 103B.

[0328] Next, a heat treatment (also called post-bake) is performed. By performing the heat treatment, the insulating layer 127a can be deformed into an insulating layer 127 having a tapered shape on its side surface (Figure 8(C)). This heat treatment is performed at a temperature lower than the heat resistance temperature of the organic compound layer. The heat treatment can be performed at a substrate temperature of 50°C to 200°C, preferably 60°C to 150°C, and more preferably 70°C to 130°C. The heating atmosphere may be an atmospheric atmosphere or an inert gas atmosphere. The heating atmosphere may also be an atmospheric pressure atmosphere or a reduced pressure atmosphere. This improves the adhesion between the insulating layer 127 and the inorganic insulating layer 125, and also improves the corrosion resistance of the insulating layer 127.

[0329] In the first etching process, by not completely removing sacrificial layers 158R, 158G, and 158B, and leaving them in a thinned state, it is possible to prevent damage and degradation of organic compound layers 103R, 103G, and 103B during the heat treatment. Therefore, the reliability of the light-emitting device can be improved.

[0330] Next, as shown in Figure 9(A), etching is performed using the insulating layer 127 as a mask to remove a portion of the sacrificial layer 158R, sacrificial layer 158G, and sacrificial layer 158B. This creates openings in each of the sacrificial layer 158R, sacrificial layer 158G, and sacrificial layer 158B, exposing the upper surfaces of the organic compound layer 103R, organic compound layer 103G, organic compound layer 103B, and conductive layer 152C. In the following, this etching process may be referred to as the second etching process.

[0331] The edges of the inorganic insulating layer 125 are covered with the insulating layer 127. Figure 9(A) also shows an example where the insulating layer 127 covers a portion of the edge of the sacrificial layer 158G (specifically, the tapered portion formed by the first etching process), while the tapered portion formed by the second etching process is exposed.

[0332] The second etching process is performed by wet etching. By using the wet etching method, damage to the organic compound layer 103R, organic compound layer 103G, and organic compound layer 103B can be reduced compared to using the dry etching method. Wet etching can be performed using, for example, an alkaline solution or an acidic solution. It is preferable that the solution be an aqueous solution so that the organic compound layer 103 does not dissolve.

[0333] Next, as shown in Figure 9(B), a common electrode (second electrode 102) is formed on the organic compound layer 103R, the organic compound layer 103G, the organic compound layer 103B, the conductive layer 152C, and the insulating layer 127. The common electrode (second electrode 102) can be formed by sputtering or vacuum deposition.

[0334] Next, as shown in Figure 9(C), a protective layer 131 is formed on the common electrode (second electrode 102). The protective layer 131 can be formed by methods such as vacuum deposition, sputtering, CVD, or ALD. The protective layer 131 can also serve as a cap layer. By providing a cap layer, the light extraction efficiency can be improved in the case of a top-emission type light-emitting device. For example, the ordinary refractive index (n) at a wavelength of 450 nm o ) is 1.90 or higher, and the ordinary refractive index (n) at a wavelength of 520 nm o ) is 1.80 or higher, or the ordinary refractive index (n) at a wavelength of 630 nm. o By using a material with a ratio of 1.75 or higher, the total internal reflection of light from the organic compound layer 103 in the cap layer can be suppressed, thereby improving the light extraction efficiency. In addition, the cap layer can also serve as a protective layer.

[0335] Furthermore, to prevent the light-emitting device from being exposed to the atmosphere before being incorporated into a display device or light-emitting device, a sealing film may be provided on the protective layer 131. The sealing film can be made of a material that is impermeable to impurities such as water. Specifically, an aluminum oxide film may be provided by the ALD method. In addition, to prevent the light-emitting device from being exposed to the atmosphere after the protective layer 131 is formed and before the sealing film is provided, the device may be brought into the ALD apparatus in a glove box with a nitrogen atmosphere after the protective layer 131 is formed. At this time, the oxygen concentration in the glove box is preferably 100 ppm or less, more preferably 10 ppm or less, and even more preferably 1 ppm or less.

[0336] Next, the display device can be manufactured by bonding the substrate 120 onto the protective layer 131 using the resin layer 122. As described above, in one embodiment of the present invention, an insulating layer 156 is provided so as to have an area that overlaps with the side surface of the conductive layer 151, and a conductive layer 152 is formed so as to cover the conductive layer 151 and the insulating layer 156. This increases the yield of the display device and suppresses the occurrence of defects. In addition, a display device having a microlens array can also be manufactured by providing a microlens array on the protective layer 131 or the sealing film before bonding the substrate 120, and then bonding the substrate 120.

[0337] As described above, in the method for manufacturing a display device according to one aspect of the present invention, the island-shaped organic compound layer 103R, the island-shaped organic compound layer 103G, and the organic compound layer 103B are formed not using a fine metal mask, but by processing after the film is deposited on one surface, so that the island-shaped layers can be formed with a uniform thickness. This makes it possible to realize a high-resolution display device or a display device with a high aperture ratio. Furthermore, even if the resolution or aperture ratio is high and the distance between subpixels is extremely short, it is possible to suppress contact between the organic compound layer 103R, the organic compound layer 103G, and the organic compound layer 103B in adjacent subpixels. Therefore, it is possible to suppress the generation of leakage current between subpixels. This makes it possible to prevent crosstalk and realize a display device with extremely high contrast. Moreover, even a display device having a tandem type light-emitting device manufactured using photolithography can be provided with good characteristics.

[0338] (Embodiment 5) This embodiment describes a display device according to one aspect of the present invention.

[0339] The display device of this embodiment can be a high-definition display device. Therefore, the display device of this embodiment can be used, for example, as a display unit for information terminals (wearable devices) such as wristwatches and bracelets, and as a display unit for wearable devices that can be worn on the head, such as VR devices such as head-mounted displays (HMDs) and AR devices such as glasses.

[0340] Furthermore, the display device of this embodiment can be a high-resolution display device or a large-screen display device. Therefore, the display device of this embodiment can be used in electronic devices with relatively large screens, such as television equipment, desktop or notebook personal computers, computer monitors, digital signage, and large game machines such as pachinko machines, as well as in the display units of digital cameras, digital video cameras, digital photo frames, mobile phones, portable game consoles, personal information terminals, and audio playback devices.

[0341] [Display Module] Figure 10(A) shows a perspective view of the display module 280. The display module 280 includes a display device 100A and an FPC 290. Note that the display device included in the display module 280 is not limited to display device 100A, but may be any of the display devices 100B to 100E described later.

[0342] The display module 280 has substrates 291 and 292. The display module 280 has a display unit 281. The display unit 281 is an area in the display module 280 that displays an image, and is an area in which light from each pixel provided in the pixel unit 284, which will be described later, can be seen.

[0343] Figure 10(B) shows a schematic perspective view illustrating the configuration of the substrate 291. On the substrate 291, a circuit section 282, a pixel circuit section 283 on the circuit section 282, and a pixel section 284 on the pixel circuit section 283 are stacked. In addition, a terminal section 285 for connecting to the FPC 290 is provided in the portion of the substrate 291 that does not overlap with the pixel section 284. The terminal section 285 and the circuit section 282 are electrically connected by a wiring section 286, which is composed of multiple wires.

[0344] The pixel section 284 has a plurality of pixels 284a arranged periodically. A magnified view of one pixel 284a is shown on the right side of Figure 10(B). Various configurations described in the previous embodiment can be applied to the pixels 284a.

[0345] The pixel circuit section 283 has a plurality of pixel circuits 283a arranged periodically.

[0346] One pixel circuit 283a is a circuit that controls the driving of multiple elements that a single pixel 284a has.

[0347] The circuit section 282 has circuits for driving each pixel circuit 283a of the pixel circuit section 283. For example, it is preferable to have one or both of a gate line drive circuit and a source line drive circuit. In addition, it may have at least one of the following: an arithmetic circuit, a memory circuit, and a power supply circuit.

[0348] The FPC290 functions as wiring for supplying video signals or power potential, etc., to the circuit section 282 from an external source. An IC may also be mounted on the FPC290.

[0349] Since the display module 280 can be configured such that one or both of the pixel circuit section 283 and the circuit section 282 are stacked on the lower side of the pixel section 284, the aperture ratio (effective display area ratio) of the display section 281 can be made extremely high.

[0350] Because such a display module 280 is extremely high-resolution, it can be suitably used in VR devices such as HMDs or AR devices such as glasses. For example, even in a configuration where the display part of the display module 280 is viewed through lenses, the display module 280 has an extremely high-resolution display part 281, so even when the display part is magnified with lenses, pixels are not visible, and a highly immersive display can be achieved. Furthermore, the display module 280 is not limited to this and can be suitably used in electronic devices having relatively small display parts.

[0351] [Display device 100A] The display device 100A shown in Figure 11(A) includes a substrate 301, light-emitting devices 130R, 130G, 130B, a capacitor 240, and a transistor 310.

[0352] Substrate 301 corresponds to substrate 291 in Figures 10(A) and 10(B). Transistor 310 is a transistor having a channel formation region in substrate 301. For substrate 301, a semiconductor substrate such as a single-crystal silicon substrate can be used. Transistor 310 has a part of substrate 301, a conductive layer 311, a low-resistance region 312, an insulating layer 313, and an insulating layer 314. The conductive layer 311 functions as a gate electrode. The insulating layer 313 is located between substrate 301 and the conductive layer 311 and functions as a gate insulating layer. The low-resistance region 312 is a region of substrate 301 doped with impurities and functions as a source or drain. The insulating layer 314 is provided covering the side surface of the conductive layer 311.

[0353] Furthermore, an element isolation layer 315 is provided between two adjacent transistors 310 so as to be embedded in the substrate 301.

[0354] Furthermore, an insulating layer 261 is provided covering the transistor 310, and a capacitance 240 is provided on the insulating layer 261.

[0355] The capacitor 240 has a conductive layer 241, a conductive layer 245, and an insulating layer 243 located between them. The conductive layer 241 acts as one electrode of the capacitor 240, the conductive layer 245 acts as the other electrode of the capacitor 240, and the insulating layer 243 acts as the dielectric of the capacitor 240.

[0356] The conductive layer 241 is provided on the insulating layer 261 and embedded in the insulating layer 254. The conductive layer 241 is electrically connected to either the source or drain of the transistor 310 by a plug 271 embedded in the insulating layer 261. The insulating layer 243 is provided covering the conductive layer 241. The conductive layer 245 is provided in the region that overlaps with the conductive layer 241 via the insulating layer 243.

[0357] An insulating layer 255 is provided covering the capacitance 240, an insulating layer 174 is provided on the insulating layer 255, and an insulating layer 175 is provided on the insulating layer 174. Light-emitting devices 130R, 130G, and 130B are provided on the insulating layer 175. An insulator is provided in the region between adjacent light-emitting devices.

[0358] An insulating layer 156R is provided so as to have a region that overlaps with the side surface of the conductive layer 151R, an insulating layer 156G is provided so as to have a region that overlaps with the side surface of the conductive layer 151G, and an insulating layer 156B is provided so as to have a region that overlaps with the side surface of the conductive layer 151B. Furthermore, a conductive layer 152R is provided so as to cover the conductive layer 151R and the insulating layer 156R, a conductive layer 152G is provided so as to cover the conductive layer 151G and the insulating layer 156G, and a conductive layer 152B is provided so as to cover the conductive layer 151B and the insulating layer 156B. A sacrificial layer 158R is located on the organic compound layer 103R, a sacrificial layer 158G is located on the organic compound layer 103G, and a sacrificial layer 158B is located on the organic compound layer 103B.

[0359] The conductive layers 151R, 151G, and 151B are electrically connected to either the source or drain of the transistor 310 by the insulating layers 243, 255, 174, and plugs 256 embedded in the insulating layer 175, the conductive layer 241 embedded in the insulating layer 254, and plugs 271 embedded in the insulating layer 261. Various conductive materials can be used for the plugs.

[0360] Furthermore, a protective layer 131 is provided on the light-emitting devices 130R, 130G, and 130B. A substrate 120 is bonded to the protective layer 131 by a resin layer 122. Details of the components from the light-emitting device 130 to the substrate 120 can be found in Embodiment 4. The substrate 120 corresponds to the substrate 292 in Figure 10(A).

[0361] Figure 11(B) shows a modified example of the display device 100A shown in Figure 11(A). The display device shown in Figure 11(B) has a colored layer 132R, a colored layer 132G, and a colored layer 132B, and the light-emitting device 130 has a region that overlaps with one of the colored layers 132R, 132G, and 132B. In the display device shown in Figure 11(B), the light-emitting device 130 can emit, for example, white light. Also, for example, the colored layer 132R can transmit red light, the colored layer 132G can transmit green light, and the colored layer 132B can transmit blue light.

[0362] [Display device 100B] Figure 12 shows a perspective view of the display device 100B, and Figure 13 shows a cross-sectional view of the display device 100C.

[0363] The display device 100B has a configuration in which substrate 352 and substrate 351 are bonded together. In Figure 12, substrate 352 is shown with a dashed line.

[0364] The display device 100B includes a pixel section 177, a connection section 140, a circuit 356, and wiring 355, etc. Figure 12 shows an example in which IC 354 and FPC 353 are mounted on the display device 100B. Therefore, the configuration shown in Figure 12 can also be called a display module having the display device 100B, an IC (integrated circuit), and an FPC. Here, a display module is a display device on which a connector such as an FPC is attached, or on which an IC is mounted.

[0365] The connection portion 140 is provided on the outside of the pixel portion 177. The connection portion 140 may be single or multiple. The connection portion 140 is electrically connected to the common electrode of the light-emitting device and the conductive layer, and can supply potential to the common electrode.

[0366] For example, a scan line drive circuit can be used as circuit 356.

[0367] The wiring 355 has the function of supplying signals and power to the pixel unit 177 and the circuit 356. These signals and power are input to the wiring 355 from an external source via the FPC 353 or from the IC 354.

[0368] Figure 12 shows an example in which IC 354 is provided on substrate 351 using COG (Chip On Glass) or COF (Chip On Film) methods. IC 354 can be an IC having, for example, a scan line drive circuit or a signal line drive circuit. Note that the display device 100B and the display module may be configured without an IC. Alternatively, the IC may be mounted on an FPC, for example, using the COF method.

[0369] Figure 13 shows an example of a cross-section of the display device 100C, obtained by cutting a portion of the area including the FPC 353, a portion of the circuit 356, a portion of the pixel portion 177, a portion of the connection portion 140, and a portion of the area including the end portion of the display device 100B in Figure 12.

[0370] [Display device 100C] The display device 100C shown in Figure 13 has a transistor 201, a transistor 205, a light-emitting device 130R that emits red light, a light-emitting device 130G that emits green light, and a light-emitting device 130B that emits blue light, etc., between substrates 351 and 352.

[0371] Details of the light-emitting devices 130R, 130G, and 130B can be found in Embodiment 4.

[0372] Light-emitting device 130R has a conductive layer 224R, a conductive layer 151R on the conductive layer 224R, and a conductive layer 152R on the conductive layer 151R. Light-emitting device 130G has a conductive layer 224G, a conductive layer 151G on the conductive layer 224G, and a conductive layer 152G on the conductive layer 151G. Light-emitting device 130B has a conductive layer 224B, a conductive layer 151B on the conductive layer 224B, and a conductive layer 152B on the conductive layer 151B.

[0373] The conductive layer 224R is connected to the conductive layer 222b of the transistor 205 through an opening provided in the insulating layer 214. The edge of the conductive layer 151R is located outside the edge of the conductive layer 224R. The insulating layer 156R is provided so as to have a region in contact with the side surface of the conductive layer 151R, and the conductive layer 152R is provided so as to cover the conductive layer 151R and the insulating layer 156R.

[0374] The conductive layers 224G, 151G, 152G, and insulating layer 156G in the light-emitting device 130G, and the conductive layers 224B, 151B, 152B, and insulating layer 156B in the light-emitting device 130B are the same as the conductive layers 224R, 151R, 152R, and insulating layer 156R in the light-emitting device 130R, so a detailed explanation is omitted.

[0375] The conductive layer 224R, conductive layer 224G, and conductive layer 224B have recesses formed to cover the openings provided in the insulating layer 214. Layer 128 is embedded in these recesses.

[0376] Layer 128 has the function of filling and flattening the recesses of conductive layers 224R, 224G, and 224B. Conductive layers 151R, 151G, and 151B are provided on conductive layers 224R, 224G, and 224B and on layer 128, and are electrically connected to conductive layers 224R, 224G, and 224B. Therefore, regions overlapping with the recesses of conductive layers 224R, 224G, and 224B can also be used as light-emitting regions, thereby increasing the aperture ratio of the pixels.

[0377] Layer 128 may be an insulating layer or a conductive layer. Various inorganic insulating materials, organic insulating materials, and conductive materials can be used for layer 128 as appropriate. In particular, it is preferable that layer 128 be formed using an insulating material, and especially preferable that it be formed using an organic insulating material. For example, an organic insulating material that can be used for the insulating layer 127 described above can be applied to layer 128.

[0378] A protective layer 131 is provided on the light-emitting devices 130R, 130G, and 130B. The protective layer 131 and the substrate 352 are bonded via an adhesive layer 142. A light-shielding layer 157 is provided on the substrate 352. A solid encapsulation structure or a hollow encapsulation structure can be applied to encapsulate the light-emitting devices 130. In Figure 13, the space between the substrate 352 and the substrate 351 is filled with the adhesive layer 142, indicating a solid encapsulation structure. Alternatively, the space may be filled with an inert gas (such as nitrogen or argon), indicating a hollow encapsulation structure. In this case, the adhesive layer 142 may be provided in a frame shape so as not to overlap with the light-emitting devices. Furthermore, the space may be filled with a resin different from the adhesive layer 142 provided in a frame shape.

[0379] Figure 13 shows an example in which the connection portion 140 has a conductive layer 224C obtained by processing the same conductive film as conductive layers 224R, 224G, and 224B; a conductive layer 151C obtained by processing the same conductive film as conductive layers 151R, 151G, and 151B; and a conductive layer 152C obtained by processing the same conductive film as conductive layers 152R, 152G, and 152B. Figure 13 also shows an example in which an insulating layer 156C is provided so as to have a region that overlaps with the side surface of conductive layer 151C.

[0380] The display device 100C is a top-emission type. The light emitted by the light-emitting device is emitted towards the substrate 352. It is preferable to use a material with high transmittance to visible light for the substrate 352. The pixel electrodes contain a material that reflects visible light, and the opposing common electrode (second electrode 102) contains a material that transmits visible light.

[0381] On the substrate 351, insulating layers 211, 213, 215, and 214 are provided in this order. A portion of insulating layer 211 functions as a gate insulating layer for each transistor. A portion of insulating layer 213 functions as a gate insulating layer for each transistor. Insulating layer 215 is provided covering the transistors. Insulating layer 214 is provided covering the transistors and functions as a planarization layer. The number of gate insulating layers and insulating layers covering the transistors are not limited and may be a single layer or two or more layers, respectively.

[0382] It is preferable to use an inorganic insulating film as the insulating layer 211, insulating layer 213, and insulating layer 215.

[0383] An organic insulating layer is preferred for the insulating layer 214, which functions as a planarizing layer.

[0384] Transistors 201 and 205 have a conductive layer 221 that functions as a gate, an insulating layer 211 that functions as a gate insulating layer, conductive layers 222a and 222b that function as source and drain, a semiconductor layer 231, an insulating layer 213 that functions as a gate insulating layer, and a conductive layer 223 that functions as a gate.

[0385] A connection portion 204 is provided in the region of substrate 351 where substrate 352 does not overlap. At the connection portion 204, the source electrode or drain electrode of transistor 201 is electrically connected to FPC 353 via conductive layer 166 and connection layer 242. The conductive layer 166 is shown as an example of a laminated structure consisting of a conductive film obtained by processing the same conductive film as conductive layers 224R, 224G, and 224B, a conductive film obtained by processing the same conductive film as conductive layers 151R, 151G, and 151B, and a conductive film obtained by processing the same conductive film as conductive layers 152R, 152G, and 152B. On the upper surface of the connection portion 204, the conductive layer 166 is exposed. This allows the connection portion 204 and FPC 353 to be electrically connected via the connection layer 242.

[0386] It is preferable to provide a light-shielding layer 157 on the surface of the substrate 352 that faces the substrate 351. The light-shielding layer 157 can be provided between adjacent light-emitting devices, at connection points 140, and in circuits 356, etc. In addition, various optical components can be arranged on the outside of the substrate 352.

[0387] Materials that can be used for substrate 120 can be applied to substrate 351 and substrate 352, respectively.

[0388] As the adhesive layer 142, a material that can be used for the resin layer 122 can be applied.

[0389] As the connecting layer 242, an anisotropic conductive film (ACF) or an anisotropic conductive paste (ACP) can be used.

[0390] [Display device 100D] The display device 100D shown in Figure 14 differs from the display device 100C shown in Figure 13 mainly in that it is a bottom-emission type display device.

[0391] The light emitted by the light-emitting device is projected onto the substrate 351. It is preferable to use a material with high transparency to visible light for the substrate 351. On the other hand, the light transmittance of the material used for the substrate 352 is not a requirement.

[0392] It is preferable to form a light-shielding layer 317 between the substrate 351 and the transistor 201, and between the substrate 351 and the transistor 205. Figure 14 shows an example in which a light-shielding layer 317 is provided on the substrate 351, an insulating layer 153 is provided on the light-shielding layer 317, and transistors 201, 205, etc. are provided on the insulating layer 153.

[0393] The light-emitting device 130R includes a conductive layer 112R, a conductive layer 126R on the conductive layer 112R, and a conductive layer 129R on the conductive layer 126R.

[0394] The light-emitting device 130B includes a conductive layer 112B, a conductive layer 126B on the conductive layer 112B, and a conductive layer 129B on the conductive layer 126B.

[0395] The conductive layers 112R, 112B, 126R, 126B, 129R, and 129B are made of materials with high transmittance to visible light. It is preferable to use a material that reflects visible light for the second electrode 102.

[0396] Although the light-emitting device 130G is not shown in Figure 14, it is also provided.

[0397] Furthermore, while Figure 14 and others show an example where the upper surface of layer 128 has a flat portion, the shape of layer 128 is not particularly limited.

[0398] [Display device 100D2] The display device 100D2 shown in Figure 15(A) is an example of a bottom-emission type display device, different from the display device 100D shown in Figure 14. The display device 100D2 differs from the display device 100D in that it has an organic resin layer 180. Note that in the figure, the reference numerals for components that are the same as in Figure 14 may be omitted, and details should be referred to in Figure 14.

[0399] Furthermore, Figure 15(B) shows the top view layout of pixels 178 (pixels 178a and 178b) having sub-pixels 110 (sub-pixels 110R, 110G, 110B, and 110W), and Figure 15(C) shows the top view of the organic resin layer 180 in the region where sub-pixels 110R and 110G of pixel 178 are formed. The width 110Rw of the light-emitting region of sub-pixel 110R is between the light-shielding layers 317.

[0400] As shown in Figure 15(A), the organic resin layer 180 is provided on the insulating layer 214. As shown in the region enclosed by the dashed line in Figure 15(A) and in Figure 15(C), the organic resin layer 180 has curved recesses 181 (recesses 181a, recesses 181b) in at least the region where subpixels are formed. The recesses 181 may also be provided outside the light-emitting region, such as recess 181c. By providing recess 181c, the light emitted in the region overlapping with the light-shielding layer 317 or the light that has traveled to the region overlapping with the light-shielding layer 317 can be refracted and extracted from the light-emitting region, thereby improving the luminous efficiency.

[0401] Multiple recesses 181 may be formed in a matrix. Recesses 181a and 181b may be in contact with each other, or they may have a plane between them.

[0402] Furthermore, in Figure 15, the top surface shape of the recess is shown as a hexagon (Figure 15(C)) and the cross-sectional shape as a semicircle (Figure 15(A)), but other shapes may be used as needed. For example, the top surface shape of the recess may be a triangle, a quadrilateral (including rectangles and squares), a pentagon or other polygon, a polygon with rounded corners, an ellipse, or a circle.

[0403] As the organic resin layer 180, an insulating layer having an organic material can be used. For example, as the organic resin layer 180, acrylic resin, polyimide resin, epoxy resin, imide resin, polyamide resin, polyimidoamide resin, silicone resin, siloxane resin, benzocyclobutene resin, phenol resin, and precursors of these resins can be used. Alternatively, as the organic resin layer 180, organic materials such as polyvinyl alcohol (PVA), polyvinyl butyral, polyvinylpyrrolidone, polyethylene glycol, polyglycerin, pullulan, water-soluble cellulose, or alcohol-soluble polyamide resin may be used.

[0404] Furthermore, a photosensitive resin can be used as the organic resin layer 180. A photoresist may be used as the photosensitive resin. The photosensitive resin can be a positive-type material or a negative-type material.

[0405] The organic resin layer 180 may contain a material that absorbs visible light. For example, the organic resin layer 180 itself may be composed of a material that absorbs visible light, or the organic resin layer 180 may contain a pigment that absorbs visible light. As the organic resin layer 180, for example, a resin that can be used as a color filter that transmits red, blue, or green light and absorbs other light, or a resin that contains carbon black as a pigment and functions as a black matrix can be used.

[0406] Furthermore, the organic resin layer 180 has a first electrode 101 (first electrode 101R and first electrode 101W), and the first electrode 101 has an organic compound layer 103. The ends of the first electrode 101 and the organic compound layer 103 may be covered with an insulating layer 127.

[0407] Furthermore, the first electrode 101, formed on the organic resin layer 180, similarly has recesses along with the recesses of the organic resin layer 180. Additionally, the organic compound layer 103, formed on the first electrode 101, similarly has recesses along with the recesses of the first electrode 101. Furthermore, the common layer 104, formed on the organic compound layer 103, similarly has recesses along with the recesses of the organic compound layer 103. Furthermore, the second electrode 102, formed on the common layer 104, similarly has recesses along with the recesses of the common layer 104. In other words, the recesses of the organic resin layer 180, the first electrode 101, the organic compound layer 103, the common layer 104, and the second electrode 102 have a structure in which they overlap each other.

[0408] Furthermore, a common layer 104 is provided on the organic compound layer 103 and the insulating layer 127, and a second electrode 102 is provided on the common layer 104. A protective layer 131 is provided on the second electrode 102, and the structure is bonded to the substrate 352 via an adhesive layer 142.

[0409] Note that Figure 15 only shows light-emitting devices 130W and 130R, and does not show light-emitting devices 130G and 130B, but light-emitting devices 130G and 130B are also provided.

[0410] [Display device 100E] The display device 100E shown in Figure 16 is a modified version of the display device 100C shown in Figure 13, and differs from the display device 100C mainly in that it has a colored layer 132R, a colored layer 132G, and a colored layer 132B.

[0411] In the display device 100E, the light-emitting device 130 has a region that overlaps with one of the colored layers 132R, 132G, and 132B. The colored layers 132R, 132G, and 132B can be provided on the substrate 351 side of the substrate 352. The edges of the colored layer 132R, the edges of the colored layer 132G, and the edges of the colored layer 132B can overlap with the light-shielding layer 157.

[0412] In the display device 100E, the light-emitting device 130 can emit, for example, white light. Furthermore, for example, the colored layer 132R can transmit red light, the colored layer 132G can transmit green light, and the colored layer 132B can transmit blue light. The display device 100E may also be configured with the colored layers 132R, 132G, and 132B placed between the protective layer 131 and the adhesive layer 142.

[0413] [Display device 100E2] The display device 100E2 shown in Figure 17(A) is a modified version of the display device 100E shown in Figure 16, and has a microlens 182 on the colored layer 132R, colored layer 132G, and colored layer 132B. Note that in the figure, the reference numerals for components that are the same as in Figure 16 may be omitted, and details should be referred to in Figure 16.

[0414] Furthermore, Figure 17(B) shows the top view layout of pixel 178 (pixels 178a and 178b) having sub-pixels 110 (sub-pixels 110R, 110G, and 110B), and Figure 17(C) shows the top view of the microlens 182 in the region where sub-pixels 110R and 110G of pixel 178 are formed. The region in contact between the common electrode (second electrode 102) and the organic compound layer 103 is the width 110Gw of the light-emitting region of sub-pixel 110G.

[0415] The display device 100E2 shown in Figure 17(A) has a flattening film 143 on a protective layer 131, and a colored layer 132R, a colored layer 132G, and a colored layer 132B on the flattening film 143. A flattening film 144 is provided so as to cover the colored layers 132R, 132G, and 132B. A microlens 182 is provided on the flattening film 144.

[0416] Furthermore, as shown in Figure 17(C), the microlenses 182 may be provided for each sub-pixel in the region where the sub-pixels are formed.

[0417] In Figure 17(C), the top surface shape of the microlens 182 is shown as a hexagon, but other shapes may be used as needed. For example, the top surface shape of the recess may be a triangle, a quadrilateral (including rectangles and squares), a pentagon or other polygon, a polygon with rounded corners, an ellipse, or a circle.

[0418] The microlens 182 can be formed using the same material as the organic resin layer 180.

[0419] This embodiment can be appropriately combined with other embodiments or examples. Furthermore, if multiple configuration examples are shown within a single embodiment in this specification, these configuration examples can be appropriately combined.

[0420] (Embodiment 6) This embodiment describes an electronic device according to one aspect of the present invention.

[0421] The electronic device of this embodiment has a display device according to one aspect of the present invention in its display unit. The display device according to one aspect of the present invention has low power consumption and high reliability. Therefore, it can be used in the display unit of various electronic devices.

[0422] Examples of electronic devices include television sets, desktop or notebook personal computers, computer monitors, digital signage, large game machines such as pachinko machines, and other electronic devices with relatively large screens, as well as digital cameras, digital video cameras, digital photo frames, mobile phones, portable game consoles, personal digital assistants, and audio playback devices.

[0423] An example of a wearable device that can be worn on the head is illustrated using Figures 18(A) to 18(D).

[0424] The electronic device 700A shown in Figure 18(A) and the electronic device 700B shown in Figure 18(B) each include a pair of display panels 751, a pair of housings 721, a communication unit (not shown), a pair of mounting units 723, a control unit (not shown), an imaging unit (not shown), a pair of optical members 753, a frame 757, and a pair of nose pads 758.

[0425] A display device according to one embodiment of the present invention can be applied to the display panel 751. Therefore, a highly reliable electronic device can be made.

[0426] Electronic devices 700A and 700B can project an image displayed on the display panel 751 onto the display area 756 of the optical element 753. Because the optical element 753 is translucent, the user can see the image displayed on the display area superimposed on the transmitted image visible through the optical element 753.

[0427] Electronic devices 700A and 700B may be equipped with cameras capable of capturing images of the area in front of them as imaging units. Furthermore, electronic devices 700A and 700B may each be equipped with acceleration sensors such as gyro sensors to detect the orientation of the user's head and display an image corresponding to that orientation in the display area 756.

[0428] The communications unit has a wireless communication device, which can supply, for example, a video signal. Alternatively, instead of the wireless communication device, or in addition to the wireless communication device, it may be equipped with a connector to which a cable for supplying video signals and power potential can be connected.

[0429] Furthermore, electronic devices 700A and 700B are equipped with batteries that can be charged wirelessly, wired, or both.

[0430] The housing 721 may be provided with a touch sensor module.

[0431] Various types of touch sensors can be used in the touch sensor module. For example, various methods such as capacitive, resistive, infrared, electromagnetic induction, surface acoustic wave, or optical sensors can be employed. In particular, it is preferable to apply capacitive or optical sensors to the touch sensor module.

[0432] The electronic device 800A shown in Figure 18(C) and the electronic device 800B shown in Figure 18(D) each include a pair of display units 820, a housing 821, a communication unit 822, a pair of mounting units 823, a control unit 824, a pair of imaging units 825, and a pair of lenses 832.

[0433] A display device according to one embodiment of the present invention can be applied to the display unit 820. Therefore, a highly reliable electronic device can be made.

[0434] The display unit 820 is located inside the housing 821, in a position where it can be seen through the lens 832. Furthermore, by displaying different images on a pair of display units 820, a three-dimensional display using parallax can also be performed.

[0435] Preferably, electronic devices 800A and 800B have a mechanism that allows the left and right positions of the lens 832 and the display unit 820 to be in an optimal position according to the user's eye position.

[0436] The attachment part 823 allows the user to attach the electronic device 800A or the electronic device 800B to their head.

[0437] The imaging unit 825 has the function of acquiring external information. The data acquired by the imaging unit 825 can be output to the display unit 820. An image sensor can be used in the imaging unit 825. In addition, multiple cameras may be provided to accommodate multiple angles of view, such as telephoto and wide-angle.

[0438] The electronic device 800A may have a vibration mechanism that functions as a bone conduction earphone.

[0439] Electronic devices 800A and 800B may each have input terminals. Cables can be connected to the input terminals to supply video signals from video output devices, etc., and power for charging batteries provided within the electronic devices.

[0440] An electronic device according to one aspect of the present invention may have a function for wireless communication with an earphone 750.

[0441] Furthermore, the electronic device may have an earphone section. The electronic device 700B shown in Figure 18(B) has an earphone section 727. Some of the wiring connecting the earphone section 727 and the control unit may be located inside the housing 721 or the mounting section 723.

[0442] Similarly, the electronic device 800B shown in Figure 18(D) has an earphone unit 827. For example, the earphone unit 827 and the control unit 824 can be connected to each other by a wire.

[0443] Thus, as one embodiment of the present invention, both eyeglass-type (electronic devices 700A and 700B, etc.) and goggle-type (electronic devices 800A and 800B, etc.) are preferred as electronic devices.

[0444] The electronic device 6500 shown in Figure 19(A) is a portable information terminal that can be used as a smartphone.

[0445] The electronic device 6500 includes a housing 6501, a display unit 6502, a power button 6503, a button 6504, a speaker 6505, a microphone 6506, a camera 6507, and a light source 6508, etc. The display unit 6502 has a touch panel function.

[0446] A display device according to one embodiment of the present invention can be applied to the display unit 6502. Therefore, a highly reliable electronic device can be made.

[0447] Figure 19(B) is a schematic cross-sectional view of the housing 6501 including the end on the microphone 6506 side.

[0448] A light-transmitting protective member 6510 is provided on the display side of the housing 6501, and the display panel 6511, optical member 6512, touch sensor panel 6513, printed circuit board 6517, and battery 6518 are arranged in the space enclosed by the housing 6501 and the protective member 6510.

[0449] The protective member 6510 is fixed to the display panel 6511, the optical member 6512, and the touch sensor panel 6513 by an adhesive layer (not shown).

[0450] In the area outside the display unit 6502, a portion of the display panel 6511 is folded back, and the FPC 6515 is connected to this folded portion. IC 6516 is mounted on the FPC 6515. The FPC 6515 is connected to terminals provided on the printed circuit board 6517.

[0451] A display device according to one embodiment of the present invention can be applied to the display panel 6511. This makes it possible to realize an extremely lightweight electronic device. Furthermore, because the display panel 6511 is extremely thin, it is possible to incorporate a large-capacity battery 6518 while keeping the thickness of the electronic device low. In addition, by folding back a part of the display panel 6511 and placing the connection part with the FPC 6515 on the back of the pixel section, an electronic device with a narrow bezel can be realized.

[0452] Figure 19(C) shows an example of a television system. The television system 7100 has a display unit 7000 incorporated into a housing 7171. Here, the housing 7171 is shown supported by a stand 7173.

[0453] A display device according to one embodiment of the present invention can be applied to the display unit 7000. Therefore, a highly reliable electronic device can be made.

[0454] The television device 7100 shown in Figure 19(C) can be operated using the operation switches on the housing 7171 and a separate remote control unit 7151.

[0455] Figure 19(D) shows an example of a notebook personal computer. The notebook personal computer 7200 has a casing 7211, a keyboard 7212, a pointing device 7213, and an external connection port 7214, etc. A display unit 7000 is incorporated into the casing 7211.

[0456] A display device according to one embodiment of the present invention can be applied to the display unit 7000. Therefore, a highly reliable electronic device can be made.

[0457] Figures 19(E) and 19(F) show examples of digital signage that can be used in shop windows and display cases.

[0458] The digital signage 7300 shown in Figure 19(E) comprises a housing 7301, a display unit 7000, and a speaker 7303, etc. Furthermore, it may include LED lamps, operation keys (including a power switch or operation switch), connection terminals, various sensors, a microphone, etc.

[0459] Figure 19(F) shows a digital signage 7400 mounted on a cylindrical column 7401. The digital signage 7400 has a display unit 7000 that is provided along the curved surface of the column 7401.

[0460] In Figures 19(E) and 19(F), a display device according to one embodiment of the present invention can be applied to the display unit 7000. Therefore, a highly reliable electronic device can be made.

[0461] The larger the display area 7000, the more information can be provided at once. Furthermore, a larger display area 7000 is more eye-catching, which can, for example, enhance the effectiveness of advertising.

[0462] In particular, when using a display device according to one embodiment of the present invention for advertising using the digital signage 7400 shown in Figures 19(E) and 19(F), the degree of freedom of expression can be increased by using a light-transmitting panel. For example, a light-transmitting display device can be manufactured by using wiring and support members made of a conductive film that transmits visible light and adjusting the distance between the pixel electrodes. Furthermore, by making the column 7401 from tempered glass or the like, it can also be used as a showcase.

[0463] Furthermore, in addition to the wiring and support members using the conductive film that transmits visible light as described above, a tandem-type light-emitting device according to one aspect of the present invention can increase the brightness per pixel. In other words, good display is possible even with a small aperture ratio of the display device, thus increasing the light transmittance in the display section of the display device. Therefore, it is suitable as a light-transmitting display device according to one aspect of the present invention.

[0464] Furthermore, as shown in Figures 19(E) and 19(F), it is preferable that the digital signage 7300 or digital signage 7400 can be linked wirelessly with an information terminal 7311 or information terminal 7411 such as a smartphone owned by the user.

[0465] The electronic equipment shown in Figures 20(A) to 20(G) includes a housing 9000, a display unit 9001, a speaker 9003, operation keys 9005 (including a power switch or operation switch), connection terminals 9006, sensors 9007 (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 9008, etc.

[0466] The electronic devices shown in Figures 20(A) to 20(G) have various functions. For example, they may have functions to display various information (still images, videos, text images, etc.) on a display unit, touch panel functions, functions to display a calendar, date or time, functions to control processing by various software (programs), wireless communication functions, functions to read and process programs or data recorded on a recording medium, etc.

[0467] The details of the electronic equipment shown in Figures 20(A) to 20(G) will be explained below.

[0468] Figure 20(A) is a perspective view showing a personal digital information terminal (PDI) 9171. The PDI 9171 can be used, for example, as a smartphone. The PDI 9171 may also be equipped with a speaker 9003, a connection terminal 9006, or a sensor 9007. Furthermore, the PDI 9171 can display text and image information on multiple surfaces. Figure 20(A) shows an example where three icons 9050 are displayed. Information 9051, indicated by a dashed rectangle, can also be displayed on other surfaces of the display unit 9001. Examples of information 9051 include notifications of incoming emails, SNS messages, phone calls, etc., the subject of emails or SNS messages, the sender's name, date and time, time, battery level, signal strength, etc. Alternatively, icons 9050, etc., may be displayed in the position where the information 9051 is displayed.

[0469] Figure 20(B) is a perspective view showing the personal digital assistant (PDA) 9172. The PDA 9172 has the function of displaying information on three or more sides of the display unit 9001. Here, an example is shown in which information 9052, information 9053, and information 9054 are displayed on different sides. For example, a user can check information 9053, which is displayed in a position that can be observed from above the PDA 9172, while the PDA 9172 is stored in the breast pocket of their clothing.

[0470] Figure 20(C) is a perspective view showing the tablet terminal 9173. The tablet terminal 9173 can run various applications, such as mobile phone calls, email, document viewing and creation, music playback, internet communication, and computer games. The tablet terminal 9173 has a display unit 9001, a camera 9002, a microphone 9008, and a speaker 9003 on the front of the housing 9000. Operation keys 9005 are located on the left side of the housing 9000 as buttons for operation, and connection terminals 9006 are located on the bottom.

[0471] Figure 20(D) is a perspective view showing a wristwatch-type personal information terminal 9200. The personal information terminal 9200 can be used, for example, as a smartwatch (registered trademark). The personal information terminal 9200 may have an operation key 9005 as an operation button on the left side of the housing 9000 and a sensor 9007 on the bottom. As an example, a curved bangle-type housing 9000 is shown, but the housing 9000 may be structured to allow attachment of a belt or the like. The display unit 9001 has a curved display surface and can display along the curved surface. The power storage device 9004 may also have a curved shape that follows the housing 9000. The power storage device 9004 is also flexible and can be bent according to the change in shape when attached or detached. It may also have a charging control IC connected to the power storage device 9004. The personal information terminal 9200 can also make hands-free calls by communicating with, for example, a wireless communication headset. Furthermore, the portable information terminal 9200 can wirelessly transmit data to and from other information terminals, and can also be charged wirelessly. Alternatively, data transmission and charging may be performed via wired connections using a connection terminal 9006 provided on the housing 9000.

[0472] Figures 20(E) to 20(G) are perspective views showing a foldable portable information terminal 9201. Figure 20(E) shows the portable information terminal 9201 in an unfolded state, Figure 20(G) shows it in a folded state, and Figure 20(F) shows a state in between, transitioning from one of Figures 20(E) or 20(G) to the other. The portable information terminal 9201 offers excellent portability in its folded state and excellent readability of the display due to its seamless, wide display area in its unfolded state. The display unit 9001 of the portable information terminal 9201 is supported by three housings 9000 connected by hinges 9055. For example, the display unit 9001 can be bent with a radius of curvature of 0.1 mm to 150 mm.

[0473] This embodiment can be appropriately combined with other embodiments or examples. Furthermore, if multiple configuration examples are shown within a single embodiment in this specification, these configuration examples can be appropriately combined. [Examples]

[0474] (Synthesis Example 1) In this example, we will describe the synthesis method of 2,2'-(1,3-phenylene)bis[9-(1-pyrrolidinyl)-1,10-phenanthroline] (abbreviated as mPrdPhen2P), which is shown by structural formula (100) in Embodiment 1. The structure of mPrdPhen2P is shown below.

[0475] [ka]

[0476] <Step 1: Synthesis of 2,2'-(1,3-phenylene)bis(9-chloro-1,10-phenanthroline)> 7.42 g (29.8 mmol) of 2,9-dichloro-1,10-phenanthroline, 1.65 g (9.95 mmol) of 1,3-phenylenediboronic acid, 8.23 ​​g (59.6 mmol) of potassium carbonate, 49 mL of toluene, 17 mL of ethanol, and 30 mL of water were added to a three-necked flask and degassed by stirring under reduced pressure. 0.335 g (0.290 mmol) of tetrakis(triphenylphosphine)palladium(0) was added to this mixture and stirred at 100°C for 6 hours under a nitrogen stream. After stirring, the mixture was allowed to cool to room temperature. The precipitated solid of this mixture was collected by suction filtration. This solid was purified by silica gel column chromatography (eluent: dichloromethane followed by dichloromethane:chloroform = 10:1). The resulting fraction was concentrated to obtain a solid. Ethyl acetate and hexane were added to this solid, and ultrasonic waves were irradiated. The solid was then collected by suction filtration, yielding the target white solid in a yield of 2.76 g and a yield of 55.2%. The synthesis scheme for 2,2'-(1,3-phenylene)bis(9-chloro-1,10-phenanthroline) is shown in the following formula (a-1).

[0477] [ka]

[0478] <Step 2: Synthesis of mPrdPhen2P> 2.76 g (5.48 mmol) of 2,2'-(1,3-phenylene)bis(9-chloro-1,10-phenanthroline), 0.819 g (11.5 mmol) of 1H-pyrrolidine, and 2.50 g (16.4 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene (abbreviated as DBU®) were added to a three-necked flask and stirred at 100°C for 6 hours under a nitrogen stream. After stirring, the mixture was allowed to cool to room temperature. The precipitated solid of this mixture was collected by suction filtration. Water was added to this solid and ultrasonic treatment was performed, and the solid was collected by suction filtration. Ethanol was added to this solid and ultrasonic treatment was performed, and the solid was collected by suction filtration, yielding the target yellow solid in a yield of 2.96 g and 94%. The synthesis scheme of mPrdPhen2P is shown in the following formula (a-2).

[0479] [ka]

[0480] The resulting yellow solid was purified by sublimation using the train sublimation method. Sublimation purification was performed at a pressure of 4.2 × 10⁻⁶. -2 The experiment was conducted by heating at Pa and a heating temperature of 280°C for 48 hours. As a result, the target substance was obtained as a yellow solid.

[0481] mPrdPhen2P after sublimation purification 1 The 1H NMR spectra are shown in Figures 21(A) to 21(C). Figure 21(B) is an enlarged view of the 6.5 ppm to 10 ppm range from Figure 21(A), and Figure 21(C) is an enlarged view of the 1 ppm to 4.5 ppm range from Figure 21(A). 1 The results of the 1H NMR measurement are shown below. From these results, it was confirmed that mPrdPhen2P was obtained.

[0482] 1 H NMR (CDCl3,300MHz):δ=9.65-9.64(1H,m),8.63(2H,dd,J=7.7Hz,1.8Hz),8.33(2H,d,J=8.4Hz),8.24(2H,d,J=8.4Hz),7.97(2H,d,J=8 .8Hz),7.74(1H,t,J=7.9Hz),7.63(2H,d,J=8.4Hz),7.49(2H,d,J=8.4Hz),6.88(2H,d,J=8.8Hz),3.91(8H,brs),2.19-2.14(8H,m).

[0483] Furthermore, the glass transition temperature (Tg) and crystallization temperature (Tc) of mPrdPhen2P were measured. Tg and Tc were measured using a differential scanning calorimetry system (DSC8500, PerkinElmer Japan Co., Ltd.) by placing the powder on an aluminum cell and heating it at a rate of 40°C / min. As a result, the Tg of mPrdPhen2P was 152°C, and Tc was not observed. Therefore, it was found that mPrdPhen2P is an organic compound with good heat resistance and low crystallinity, suitable for use in light-emitting devices. [Examples]

[0484] This example describes in detail a light-emitting device according to one aspect of the present invention and a comparative light-emitting device. The structural formulas of the main organic compounds used in this example are shown below.

[0485] [ka]

[0486] (Method for fabricating light-emitting device 1-1) First, silver was sequentially layered onto the substrate using a sputtering method to form a reflective electrode with a thickness of 100 nm, and indium tin oxide (ITSO) containing silicon dioxide to form a transparent electrode with a thickness of 85 nm, thereby forming a first electrode 101 measuring 2 mm x 2 mm. The transparent electrode functions as an anode and, together with the reflective electrode, is considered to be part of the first electrode 101.

[0487] Next, as a pretreatment for forming the light-emitting device on the substrate, the substrate surface was washed with water and then fired at 200°C for 1 hour.

[0488] After that, approximately 1 × 10 -4 The substrate was introduced into a vacuum deposition apparatus where the internal pressure was reduced to Pa. After vacuum firing at 170°C for 30 minutes in the heating chamber of the vacuum deposition apparatus, the substrate was allowed to cool for approximately 30 minutes.

[0489] Next, the substrate was fixed to a holder provided in the vacuum deposition apparatus so that the surface on which the first electrode 101 was formed was facing downwards. On the first electrode 101, a hole injection layer 111 was formed by co-depositing N-(biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviated as PCBBiF), represented by the above structural formula (i), and a fluorine-containing electron-accepting material (OCHD-003) with a molecular weight of 672, in a weight ratio of 1:0.03 (=PCBBiF:OCHD-003) and with a film thickness of 10 nm.

[0490] A PCBBiF film was deposited on the hole injection layer 111 to a thickness of 85 nm to form a first hole transport layer.

[0491] Next, on the first hole transport layer, 8-(p-terphenyl-3-yl)-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofl[3,2-d]pyrimidine (abbreviated as 8mpTP-4mDBtPBfpm), represented by the above structural formula (ii), 9-(2-naphthyl)-9'-phenyl-3,3'-bi-9H-carbazole (abbreviated as βNCCP), represented by the above structural formula (iii), and [2-d3-methyl-8-( A first light-emitting layer was formed by co-depositing 2-pyridinyl-κN)benzofl[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridinyl-κN2)phenyl-κC]iridium(III) (abbreviation: Ir(5mppy-d3)2(mbfpypy-d3)) in a weight ratio of 0.5:0.5:0.1 (=8mpTP-4mDBtPBfpm:βNCCP:Ir(5mppy-d3)2(mbfpypy-d3)) with a film thickness of 40 nm.

[0492] Subsequently, 2-{3-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-9-yl]phenyl}dibenzo[f,h]quinoxaline (abbreviation: 2mPCCzPDBq), represented by the above structural formula (v), was deposited to a thickness of 10 nm to form the first electron transport layer.

[0493] After the formation of the first electron transport layer, the first layer was formed by co-depositing 2,2'-(1,3-phenylene)bis[9-(1-pyrrolidinyl)-1,10-phenanthroline] (abbreviated as mPrdPhen2P), represented by the above structural formula (vii), and lithium oxide (Li2O) in a volume ratio of 1.0:0.02 (=mPrdPhen2P:Li2O) with a film thickness of 5 nm. The third layer was formed by depositing copper phthalocyanine (abbreviated as CuPc), represented by the above structural formula (viii), with a film thickness of 2 nm. Furthermore, the second layer was formed by co-depositing PCBBiF and OCHD-003 in a weight ratio of 1:0.15 (=PCBBiF:OCHD-003) with a film thickness of 10 nm, thereby forming an intermediate layer.

[0494] A second hole transport layer was formed by depositing PCBBiF onto the intermediate layer to a thickness of 50 nm.

[0495] A second light-emitting layer was formed on the second hole transport layer by co-depositing 8mpTP-4mDBtPBfpm, βNCCP, and Ir(5mppy-d3)2(mbfpypy-d3) in a weight ratio of 0.5:0.5:0.1 (=8mpTP-4mDBtPBfpm:βNCCP:Ir(5mppy-d3)2(mbfpypy-d3)) with a film thickness of 40 nm.

[0496] Subsequently, 2mPCCzPDBq was deposited to a thickness of 20 nm, and then 2,2'-(1,3-phenylene)bis(9-phenyl-1,10-phenanthroline) (abbreviated as mPPhen2P), represented by the above structural formula (ix), was deposited to a thickness of 20 nm to form a second electron transport layer.

[0497] Subsequently, lithium fluoride (LiF) and ytterbium (Yb) were co-deposited in a volume ratio of 1:0.5 (=LiF:Yb) with a film thickness of 1.5 nm. Then, silver (Ag) and magnesium (Mg) were co-deposited in a volume ratio of 1:0.1 (=Ag:Mg) with a film thickness of 15 nm to form the second electrode 102. Furthermore, 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), represented by the above structural formula (x), was deposited on the second electrode 102 as a cap layer with a film thickness of 70 nm to improve the light extraction efficiency.

[0498] Next, in a glove box under a nitrogen atmosphere, the light-emitting device was sealed with a glass substrate to prevent exposure to the atmosphere (applying a UV-curable sealant around the element, irradiating only the sealant with UV light without irradiating the light-emitting device, and heat-treating at 80°C for 1 hour under atmospheric pressure) to form light-emitting device 1-1.

[0499] (Method for fabricating light-emitting devices 1-2) Light-emitting device 1-2 is a light-emitting device obtained by heating the fabricated light-emitting device 1-1 at 130°C for 1 hour.

[0500] (Method for fabricating comparative light-emitting device 1-1) Comparative light-emitting device 1-1 was fabricated in the same manner as light-emitting device 1-1, except that the mPrdPhen2P used in the first layer of light-emitting device 1-1 was replaced with 4,7-di-1-pyrrolidinyl-1,10-phenanthroline (abbreviated as Pyrrd-Phen), represented by the above structural formula (xi), and the film thickness of the first hole transport layer was deposited to 90 nm and the film thickness of the second hole transport layer to 55 nm.

[0501] (Method for fabricating comparative light-emitting devices 1-2) Comparative light-emitting device 1-2 is a light-emitting device obtained by heating the fabricated comparative light-emitting device 1-1 at 130°C for 1 hour.

[0502] The device structures of light-emitting device 1 and comparative light-emitting device 1 are shown below.

[0503] [Table 1]

[0504] [Table 2]

[0505] Figure 22 shows the luminance-current density characteristics of light-emitting device 1-1, light-emitting device 1-2, comparative light-emitting device 1-1, and comparative light-emitting device 1-2; Figure 23 shows the current efficiency-luminance characteristics; Figure 24 shows the luminance-voltage characteristics; Figure 25 shows the current density-voltage characteristics; and Figure 26 shows the field emission spectra of light-emitting device 1-1, light-emitting device 1-2, comparative light-emitting device 1-1, and comparative light-emitting device 1-2. 2 Table 3 shows the main characteristics of the vicinity. Luminance, CIE chromaticity, and field emission spectra were measured using a spectroradiometer (Topcon SR-UL1R) at room temperature.

[0506] [Table 3]

[0507] Figures 22 to 26 and Table 3 show that light-emitting device 1-1, light-emitting device 1-2, and comparative light-emitting device 1-1 all exhibited high current efficiency and functioned as tandem light-emitting devices. However, comparative light-emitting device 1-2 showed a significant increase in driving voltage and a significant decrease in current efficiency.

[0508] From the above results, it was found that the light-emitting device in Embodiment 1, which uses mPrdPhen2P, an organic compound represented by general formula (G1), as the first layer in a tandem-type light-emitting device, does not experience a decrease in its properties even when exposed to high-temperature environments and maintains good properties. On the other hand, it was found that the light-emitting device using Pyrrd-Phen as the first layer suffers from a degradation of properties when exposed to high-temperature environments.

[0509] The Tg of mPrdPhen2P was 152°C, and the Tg of Pyrrd-Phen was 78°C. From these results, it was found that the organic compound represented by general formula (G1) in Embodiment 1 has good heat resistance and is suitable for use as the first layer in a tandem type light-emitting device. The Tg was measured using a differential scanning calorimetry system (DSC8500, manufactured by PerkinElmer Japan Co., Ltd.).

[0510] Thus, in Embodiment 1, the high heat resistance of mPrdPhen2P, an organic compound represented by general formula (G1), makes it possible to provide a light-emitting device with good heat resistance. [Examples]

[0511] This embodiment will describe in detail a light-emitting device according to one aspect of the present invention. The structural formulas of the main organic compounds used in this embodiment are shown below.

[0512] [ka]

[0513] (Method for fabricating light-emitting device 2) First, silver was sequentially layered onto the substrate using a sputtering method to form a reflective electrode with a thickness of 100 nm, and indium tin oxide (ITSO) containing silicon dioxide to form a transparent electrode with a thickness of 85 nm, thereby forming a first electrode 101 measuring 2 mm x 2 mm. The transparent electrode functions as an anode and, together with the reflective electrode, is considered to be part of the first electrode 101.

[0514] Next, as a pretreatment for forming the light-emitting device on the substrate, the substrate surface was washed with water and then fired at 200°C for 1 hour.

[0515] After that, approximately 1 × 10 -4 The substrate was introduced into a vacuum deposition apparatus where the internal pressure was reduced to Pa. After vacuum firing at 170°C for 30 minutes in the heating chamber of the vacuum deposition apparatus, the substrate was allowed to cool for approximately 30 minutes.

[0516] Next, the substrate was fixed to a holder provided in the vacuum deposition apparatus so that the surface on which the first electrode 101 was formed was facing downwards. On the first electrode 101, a hole injection layer 111 was formed by co-depositing N-(biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviated as PCBBiF), represented by the above structural formula (i), and a fluorine-containing electron-accepting material (OCHD-003) with a molecular weight of 672, in a weight ratio of 1:0.03 (=PCBBiF:OCHD-003) and with a film thickness of 10 nm.

[0517] A PCBBiF film was deposited on the hole injection layer 111 to a thickness of 85 nm to form a first hole transport layer.

[0518] Next, on the first hole transport layer, 8-(p-terphenyl-3-yl)-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofl[3,2-d]pyrimidine (abbreviated as 8mpTP-4mDBtPBfpm), represented by the above structural formula (ii), 9-(2-naphthyl)-9'-phenyl-3,3'-bi-9H-carbazole (abbreviated as βNCCP), represented by the above structural formula (iii), and [2-d3-methyl-8-( A first light-emitting layer was formed by co-depositing 2-pyridinyl-κN)benzofl[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridinyl-κN2)phenyl-κC]iridium(III) (abbreviation: Ir(5mppy-d3)2(mbfpypy-d3)) in a weight ratio of 0.5:0.5:0.1 (=8mpTP-4mDBtPBfpm:βNCCP:Ir(5mppy-d3)2(mbfpypy-d3)) with a film thickness of 40 nm.

[0519] Subsequently, 2-{3-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-9-yl]phenyl}dibenzo[f,h]quinoxaline (abbreviation: 2mPCCzPDBq), represented by the above structural formula (v), was deposited to a thickness of 10 nm to form the first electron transport layer.

[0520] After the formation of the first electron transport layer, the first layer was formed by co-depositing 2,2'-(1,3-phenylene)bis[9-(1-pyrrolidinyl)-1,10-phenanthroline] (abbreviated as mPrdPhen2P), represented by the above structural formula (vii), and indium (In) in a volume ratio of 1.0:0.02 (=mPrdPhen2P:In) with a film thickness of 5 nm. The third layer was formed by depositing copper phthalocyanine (abbreviated as CuPc), represented by the above structural formula (viii), with a film thickness of 2 nm. Furthermore, the second layer was formed by co-depositing PCBBiF and OCHD-003 in a weight ratio of 1:0.15 (=PCBBiF:OCHD-003) with a film thickness of 10 nm, thereby forming an intermediate layer.

[0521] A second hole transport layer was formed by depositing PCBBiF onto the intermediate layer to a thickness of 50 nm.

[0522] A second light-emitting layer was formed on the second hole transport layer by co-depositing 8mpTP-4mDBtPBfpm, βNCCP, and Ir(5mppy-d3)2(mbfpypy-d3) in a weight ratio of 0.5:0.5:0.1 (=8mpTP-4mDBtPBfpm:βNCCP:Ir(5mppy-d3)2(mbfpypy-d3)) with a film thickness of 40 nm.

[0523] Subsequently, 2mPCCzPDBq was deposited to a thickness of 20 nm, and then 2,2'-(1,3-phenylene)bis(9-phenyl-1,10-phenanthroline) (abbreviated as mPPhen2P), represented by the above structural formula (ix), was deposited to a thickness of 20 nm to form a second electron transport layer.

[0524] The sample, with the second electron transport layer formed, was exposed to air for 1 hour. Afterward, approximately 1 × 10⁻⁶ -4 In a heating chamber within a vacuum deposition apparatus where the internal pressure was reduced to Pa, heating (vacuum baking) was performed at 100°C for 1 hour.

[0525] Subsequently, lithium fluoride (LiF) and ytterbium (Yb) were co-deposited in a volume ratio of 1:0.5 (=LiF:Yb) with a film thickness of 1.5 nm. Then, silver (Ag) and magnesium (Mg) were co-deposited in a volume ratio of 1:0.1 (=Ag:Mg) with a film thickness of 15 nm to form the second electrode 102. Furthermore, 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), represented by the above structural formula (x), was deposited on the second electrode 102 as a cap layer with a film thickness of 70 nm to improve the light extraction efficiency.

[0526] Next, in a glove box under a nitrogen atmosphere, the light-emitting device was sealed with a glass substrate to prevent exposure to the atmosphere (applying a UV-curable sealant around the element, irradiating only the sealant with UV light without irradiating the light-emitting device, and heat-treating at 80°C for 1 hour under atmospheric pressure) to form light-emitting device 2.

[0527] (Method for fabricating comparative light-emitting device 2) Comparative light-emitting device 2 was fabricated in the same manner as light-emitting device 2, except that the mPrdPhen2P used in the first layer of light-emitting device 2 was replaced with mPPhen2P.

[0528] The device structures of light-emitting device 2 and comparative light-emitting device 2 are shown below.

[0529] [Table 4]

[0530] Figure 27 shows the luminance-current density characteristics of light-emitting device 2 and comparative light-emitting device 2, Figure 28 shows the current efficiency-luminance characteristics, Figure 29 shows the luminance-voltage characteristics, Figure 30 shows the current density-voltage characteristics, and Figure 31 shows the field emission spectra. In addition, the luminance of light-emitting device 2 and comparative light-emitting device 2 at 1000 cd / m² is shown. 2 Table 5 shows the main characteristics of the vicinity. Luminance, CIE chromaticity, and field emission spectra were measured using a spectroradiometer (Topcon SR-UL1R) at room temperature.

[0531] [Table 5]

[0532] From Figures 27 to 31 and Table 5, it was found that the light-emitting device 2 in Embodiment 1, which uses mPrdPhen2P, an organic compound represented by general formula (G1), as an intermediate layer, exhibits good characteristics even after exposure to air and heating. On the other hand, comparative light-emitting device 2, which uses mPPhen2P, having a similar structure to the organic compound represented by general formula (G1) in Embodiment 1, as an intermediate layer, was found to be a light-emitting device with lower current efficiency and a higher driving voltage compared to light-emitting device 2.

[0533] Thus, in comparative light-emitting device 2, exposure to air reduces the interaction between mPPhen2P and In, resulting in decreased electron injection in the intermediate layer. However, in light-emitting device 2, the aliphatic cyclic amino group of mPrdPhen2P increases the electron density of the nitrogen atom, resulting in a stronger interaction with In. Therefore, it is possible to create a light-emitting device that is less susceptible to the effects of air exposure. [Explanation of symbols]

[0534] 100A display device 100B display device 100C display device 100D display device 100E display device 100 display device 101 First electrode 101B First electrode 101G First electrode 101R First electrode 101W First electrode 102 Second electrode 103B Organic compound layer 103G organic compound layer 103R Organic compound layer 103 Organic compound layer 104 Common layer 110B subpixel 110G sub-pixels 110R sub-pixel 110W sub-pixel 110 subpixels 111 Hole injection layer 112B Conductive layer 112R conductive layer 112 Hole transport layer 113 Emitting layer 114 Electron transport layer 115 Electron injection layer 116 Charge generation layer 117 p-type layer 118 Electron relay layer 119 Electron injection buffer layer 120 circuit boards 122 Resin layer 125f inorganic insulating film 125 Inorganic insulating layer 126B Conductive layer 126R conductive layer 127a Insulating layer 127f insulating film 127 Insulating layer 128 layers 129B Conductive layer 129R conductive layer 130B Light-emitting device 130G Light-emitting Device 130R Light-emitting Device 130W Light-emitting Device 130 Light-emitting devices 131 Protective layer 132B Colored layer 132G colored layer 132R colored layer 140 Connection part 141 areas 142 Adhesive layer 151B Conductive layer 151C conductive layer 151f Conductive film 151G conductive layer 151R conductive layer 151 Conductive layer 152B Conductive layer 152C conductive layer 152f Conductive film 152G conductive layer 152R conductive layer 152 Conductive layer 153 Insulating layer 155 Common electrode 156B Insulating layer 156C insulating layer 156f insulating film 156G insulating layer 156R Insulating Layer 156 Insulating layer 157 Light blocking layer 158B Sacrifice Layer 158Bf sacrificial membrane 158G Sacrifice Layer 158Gf sacrificial membrane 158R Sacrifice Layer 158Rf sacrificial membrane 159B Mask layer 159Bf mask film 159G mask layer 159 Gf mask film 159R mask layer 159Rf mask membrane 166 Conductive layer 171 Insulating layer 172 Conductive layer 173 Insulating layer 174 Insulating layer 175 Insulating layer 176 plug 177 pixel section 178 pixels 178a pixels 178b pixels 179 Conductive layer 190B Resist Mask 190G Resist Mask 190R Resist Mask 191 Resist Mask 201 Transistors 204 Connection part 205 transistors 211 Insulating layer 213 Insulating layer 214 Insulating layer 215 Insulating layer 221 Conductive layer 222a conductive layer 222b Conductive layer 223 Conductive layer 224B Conductive layer 224C conductive layer 224G conductive layer 224R conductive layer 231 Semiconductor layer 240 capacity 241 Conductive layer 242 Connecting Layers 243 Insulating layer 245 Conductive layer 254 Insulating layer 255 Insulating layer 256 plug 261 Insulating layer 271 Plug 280 Display Modules 281 Display section 282 Circuit section 283a Pixel Circuit 283 Pixel Circuit Section 284a pixels 284 pixel section 285 Terminal section 286 Wiring section 290 FPC 291 circuit boards 292 circuit boards 301 circuit board 310 transistors 311 Conductive layer 312 Low resistance region 313 Insulating layer 314 Insulating layer 315 element isolation layer 317 Light blocking layer 351 circuit board 352 circuit boards 353 FPC 354 IC 355 Wiring 356 circuits 501 First electrode 502 Second electrode 503 Organic compound layer 511 First light-emitting unit 512 Second light-emitting unit 513 Middle Class 601 Source line drive circuit, drive circuit section 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 First electrode 614 Insulators 616 Organic compound layer 617 Second electrode 618 Light-emitting devices 623 FET 700A electronic equipment 700B Electronic equipment 721 cabinet 723 Mounting part 727 Earphone section 750 Earphones 751 Display Panel 753 Optical components 756 Display area 757 frames 758 Nose pads 800A electronic equipment 800B Electronic equipment 820 Display section 821 cabinet 822 Communications Department 823 Mounting part 824 Control Unit 825 Imaging Unit 827 Earphone section 832 Lens 1000 Insulating layer 6500 Electronic equipment 6501 enclosure 6502 Display section 6503 Power button 6504 button 6505 Speaker 6506 Mike 6507 Camera 6508 Light source 6510 Protective component 6511 Display Panel 6512 Optical components 6513 Touch Sensor Panel 6515 FPC 6516 IC 6517 Printed circuit board 6518 Battery 7000 Display 7100 Television equipment 7151 Remote control unit 7171 enclosure 7173 Stand 7200 Notebook Personal Computer 7211 enclosure 7212 Keyboard 7213 Pointing device 7214 External connection port 7300 Digital Signage 7301 enclosure 7303 Speaker 7311 Information terminal 7400 Digital Signage 7401 pillars 7411 Information terminal 9000 cabinets 9001 Display section 9002 Camera 9003 Speaker 9005 Operation Keys 9006 Connection terminal 9007 Sensor 9008 Microphone 9050 Icon 9051 Information 9052 Information 9053 Information 9054 Information 9055 Hinge 9171 Mobile Information Terminal 9172 Mobile Information Terminal 9173 Tablet device 9200 Mobile Information Terminal 9201 Mobile Information Terminal

Claims

1. An organic compound represented by the general formula (G1). 【Chemistry 1】 (In the above general formula (G1), A １ and A ２ Each of these is an aliphatic cyclic amino group, independently represented by the following general formula (g1). 【Chemistry 2】 (In the above general formula (g1), R １１ ~R １８ Each independently represents hydrogen (including deuterium), or one of the following: a C1-C10 alkyl group, a C3-C10 cycloalkyl group, a C1-C10 alkoxy group, a substituted or unsubstituted C2-C10 secondary amino group, a substituted or unsubstituted C6-C30 monovalent aromatic hydrocarbon group, a substituted or unsubstituted C1-C30 heteroaryl group, a cyano group, a halogen, a hydroxyl group, an amide group, or a carbonyl group, and p and q each independently represent 0 to 3. １１ ~R １８ Any two of these may be bonded to each other to form a ring. Furthermore, the aliphatic cyclic amino group represented by the general formula (g1) may have an aromatic ring with 6 to 10 carbon atoms fused to it. １ Ar represents a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 1 to 25 carbon atoms, where n is an integer from 0 to 3. Note that when n is 2 or greater, there are multiple Ar groups. １ These may be the same group or different groups.

2. An organic compound represented by the general formula (G2). 【Transformation 3】 (In the above general formula (G2), A １ and A ２ are each independently a group represented by the following general formula (g1).) 【Chemistry 4】 (In the above general formula (g1), R １１ ~R １８ Each independently represents hydrogen (including deuterium), or one of the following: a C1-C10 alkyl group, a C3-C10 cycloalkyl group, a C1-C10 alkoxy group, a substituted or unsubstituted C2-C10 secondary amino group, a substituted or unsubstituted C6-C30 monovalent aromatic hydrocarbon group, a substituted or unsubstituted C1-C30 heteroaryl group, a cyano group, a halogen, a hydroxyl group, an amide group, or a carbonyl group, and p and q each independently represent 0 to 3. １１ ~R １８ Any two of these may be bonded to each other to form a ring. Furthermore, the aliphatic cyclic amino group represented by the general formula (g1) may have an aromatic ring with 6 to 10 carbon atoms fused to it. １ Ar represents a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 25 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 1 to 25 carbon atoms, where n is an integer from 0 to 3. Note that when n is 2 or greater, there are multiple Ar groups. １ These may be the same group or different groups.

3. In claim 1, An organic compound in which n in the above general formula (g1) is 0.

4. In claim 1 or claim 2, The aforementioned R １１ , R １２ , R １７ and R １８ An organic compound in which hydrogen is present.

5. In claim 3, An organic compound in which p and q are 1.

6. An organic compound represented by structural formula (100). 【Transformation 5】

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