Organic compound, material for intermediate layer, and light emitting device

Abstract

Provided is a novel organic compound with which it is possible to provide a light emitting device having good reliability. Provided is an organic compound represented by structural formula (G1). In the organic compound expressed by general formula (G1), at least one from among R20 to R27 is a group represented by general formula (g1). In the group represented by general formula (g1), R1 to R16 each independently represent hydrogen (including deuterium) or a C1-C10 alkyl group, and s, t, u, and v each independently represent a value of 0-3. Ar1 represents a substituted or unsubstituted arylene group. m represents a value of 0-2. When m is 2, the two substituted or unsubstituted arylene groups may be the same or different from each other.

Description

Organic compounds, intermediate layer materials, and light-emitting devices

[0001] One aspect of the present invention relates to organic compounds, organic semiconductor elements, light-emitting devices, photodiode sensors, display modules, lighting modules, display devices, electronic devices, lighting devices, and electronic devices. However, one aspect of the present invention is not limited to the above-mentioned technical fields. One aspect of the present invention disclosed herein relates to a product, a method, or a method of manufacture. Alternatively, one aspect of the present invention relates to a process, a machine, a manufacture, or a composition of matter. More specifically, one example of a technical field of one aspect of the present invention disclosed herein is a semiconductor device, a display device, a liquid crystal display device, a lighting device, a power storage device, a memory device, an imaging device, a method for driving them, or a method for manufacturing them.

[0002] The practical application of light-emitting devices (also called organic EL elements) that utilize electroluminescence (EL) using organic compounds is progressing. The basic structure of these light-emitting devices is an organic compound layer containing a light-emitting material sandwiched between a pair of electrodes. By applying a voltage to this light-emitting device, carriers are injected, and by utilizing the recombination energy of these carriers, light emission can be obtained from the light-emitting material.

[0003] Because the light-emitting device is self-illuminating, a display device using this device as a pixel has higher visibility than a liquid crystal display and does not require a backlight. Another major advantage of display devices using such light-emitting devices is that they can be manufactured to be thin and lightweight. Furthermore, they are characterized by their extremely fast response speed.

[0004] Furthermore, since these light-emitting devices can form a continuous, planar light-emitting layer, they can produce light in a planar manner. This is a feature that is difficult to obtain with point light sources such as incandescent bulbs and LEDs, or line light sources such as fluorescent lamps, and therefore has high value as a surface light source that can be applied to lighting and other applications.

[0005] As described above, display devices and lighting devices using light-emitting devices are suitable for a variety of electronic devices, but research and development are underway to find light-emitting devices with even better characteristics.

[0006] Patent Document 1 discloses a light-emitting device with a 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.

[0007] Japanese Patent Publication No. 2018-201012 Japanese Patent Publication No. 2024-079655

[0008] Vacuum deposition using a metal mask (mask deposition) is widely used as one method for fabricating organic compound films into predetermined shapes. However, with the increasing demand for higher density and resolution, mask deposition is approaching its limits in terms of resolution due to various reasons, such as alignment accuracy issues and spacing problems between the substrate and the mask. On the other hand, lithography can be used to process the shape of organic semiconductor films, allowing for the formation of more intricate patterns. Furthermore, this method is also easily applicable to large-area fabrication, and research on processing organic semiconductor films using lithography is progressing. However, when processing organic semiconductor films using lithography, degradation of properties and shape defects sometimes occur.

[0009] One aspect of the present invention aims to provide a novel organic compound. Alternatively, one aspect of the present invention aims to provide a novel organic compound having electron transport properties. Alternatively, one aspect of the present invention aims to provide a novel organic compound that can be used as an intermediate layer in a tandem light-emitting device. Alternatively, one aspect of the present invention aims to provide an organic compound that enables the fabrication of light-emitting devices with good properties, even when processed using lithography.

[0010] Alternatively, one aspect of the present invention aims to provide a light-emitting device with good characteristics. Alternatively, one aspect of the present invention aims to provide a light-emitting device with good reliability. Alternatively, one aspect of the present invention aims to provide a light-emitting device with a low drive voltage. Alternatively, one aspect of the present invention aims to provide a light-emitting device that is reliable and has a low drive voltage.

[0011] Alternatively, one aspect of the present invention aims to provide a light-emitting device capable of providing a display device with good characteristics. Alternatively, one aspect of the present invention aims to provide a light-emitting device capable of manufacturing a reliable display device. Alternatively, one aspect of the present invention aims to provide a display device with a low drive voltage. Alternatively, one aspect of the present invention aims to provide a light-emitting device capable of providing a display device with a low drive voltage and good reliability.

[0012] Alternatively, the objective is to provide any of the following: low-power organic semiconductor devices, light-emitting devices, light-receiving devices, display devices, electronic devices, and lighting devices. Alternatively, the objective is to provide any of the following: highly reliable electronic devices and lighting devices.

[0013] The present invention only needs to solve one of the above-mentioned problems.

[0014] One aspect of the present invention is an organic compound represented by the following general formula (G1).

[0015]

[0016] However, in the organic compound represented by the above general formula (G1), R ２０ ~R ２７At least one of R is a group represented by the above general formula (g1), and the others each independently represent hydrogen (including deuterium), 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 substituted or unsubstituted cyclic secondary amino group having 2 to 10 ring-forming carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms. In the group represented by the above general formula (g1), R １ to R １６ each independently represent hydrogen (including deuterium) or an alkyl group having 1 to 10 carbon atoms, s, t, u and v each independently represent any one of 0 to 3. Further, Ar １ represents a substituted or unsubstituted arylene group, m represents any one of 0 to 2, and when m is 2, the two substituted or unsubstituted arylene groups may be the same as or different from each other.

[0017] Alternatively, according to another aspect of the present invention, in the above structure, R ２０ to R ２７ is an organic compound wherein two of them are groups represented by the above general formula (g1).

[0018] Alternatively, another aspect of the present invention is an organic compound represented by general formula (G2).

[0019]

[0020] Provided that in the organic compound represented by the above general formula (G2), R ２０ , R ２２ , R ２５ and R ２７At least one of the groups is represented by the general formula (g1) above, and the others each independently represent hydrogen (including deuterium), a C1 to C10 alkyl group, a C3 to C10 cycloalkyl group, a C1 to C10 alkoxy group, a substituted or unsubstituted cyclic secondary amino group with 2 to 10 carbon atoms forming a ring, a substituted or unsubstituted C2 to C12 secondary amino group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group. Furthermore, in the group represented by the general formula (g1) above, R １ ~R １６ Each of the following independently represents hydrogen (including deuterium) or an alkyl group having 1 to 10 carbon atoms, and each of the following independently represents one of the values ​​from 0 to 3. Also, Ar １ represents a substituted or unsubstituted arylene group, and m represents any of 0 to 2. When m is 2, the two substituted or unsubstituted arylene groups may be the same or different from each other.

[0021] Alternatively, another aspect of the present invention is an organic compound represented by general formula (G3).

[0022]

[0023] However, in the organic compound represented by the above general formula (G3), R ２０ , R ２２ , R ２５ and R ２７ At least one of the groups is represented by the general formula (g1) above, and the others each independently represent hydrogen (including deuterium), a C1 to C10 alkyl group, a C3 to C10 cycloalkyl group, a C1 to C10 alkoxy group, a substituted or unsubstituted cyclic secondary amino group with 2 to C10 carbon atoms forming a ring, a substituted or unsubstituted C2 to C12 secondary amino group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group. Furthermore, in the group represented by the general formula (g1) above, R １ ~R １６Each of the following independently represents hydrogen (including deuterium) or an alkyl group having 1 to 10 carbon atoms, and each of the following independently represents one of the values ​​from 0 to 3. Also, Ar １ represents a substituted or unsubstituted arylene group, and m represents any of 0 to 2. When m is 2, the two substituted or unsubstituted arylene groups may be the same or different from each other.

[0024] Alternatively, another aspect of the present invention is an organic compound in which, in the above configuration, the group represented by general formula (g1) is the group represented by the following general formula (g2).

[0025]

[0026] In the group represented by the above general formula (g2), R １ ~R １６ Each of the following independently represents hydrogen (including deuterium) or an alkyl group having 1 to 10 carbon atoms, and u and v each independently represent one of 0 to 3. Also, Ar １ represents a substituted or unsubstituted arylene group, and m represents any of 0 to 2. When m is 2, the two substituted or unsubstituted arylene groups may be the same or different from each other.

[0027] Alternatively, another aspect of the present invention is an organic compound in which u and v each independently represent 0 or 1 in the above configuration.

[0028] Alternatively, another aspect of the present invention is an organic compound in which, in the above configuration, the group represented by general formula (g1) is the group represented by the following general formula (g3).

[0029]

[0030] In the group represented by the above general formula (g3), R １ ~R １６ Each of these independently represents hydrogen (including deuterium) or an alkyl group having 1 to 10 carbon atoms, Ar １ represents a substituted or unsubstituted arylene group, and m represents any of 0 to 2. When m is 2, the two substituted or unsubstituted arylene groups may be the same or different from each other.

[0031] Alternatively, another aspect of the present invention is an organic compound in which, in the above configuration, the group represented by general formula (g1) is the group represented by the following general formula (g4).

[0032]

[0033] In the group represented by the above general formula (g3), R １ ~R １６ Each of these independently represents hydrogen (including deuterium) or an alkyl group having 1 to 10 carbon atoms, Ar １ represents a substituted or unsubstituted arylene group, and m represents any of 0 to 2. When m is 2, the two substituted or unsubstituted arylene groups may be the same or different from each other.

[0034] The organic compounds of the present invention are limited to those represented by the following structural formulas (10) and (11).

[0035]

[0036] Alternatively, another aspect of the present invention is a material for an intermediate layer of a tandem light-emitting device, comprising the above-mentioned organic compound.

[0037] Alternatively, another aspect of the present invention is a tandem-type light-emitting device that uses the above-mentioned organic compound as an intermediate layer.

[0038] Alternatively, another aspect of the present invention is a tandem-type light-emitting device using the above-mentioned organic compound and a metal or metal compound as an intermediate layer.

[0039] Alternatively, another aspect of the present invention is a tandem light-emitting device using the above-mentioned organic compound and an organic compound having a phenanthroline skeleton as an intermediate layer.

[0040] Alternatively, another aspect of the present invention is a tandem light-emitting device having an intermediate layer comprising the above-mentioned organic compound, an organic compound having a phenanthroline skeleton, and a metal or metal compound.

[0041] Alternatively, another aspect of the present invention is a material for an electron injection layer of a light-emitting device, comprising the above-mentioned organic compound.

[0042] Alternatively, another aspect of the present invention is a light-emitting device in which the above-mentioned organic compound is used for an electron injection layer.

[0043] Alternatively, another aspect of the present invention is a light-emitting device that uses the above-mentioned organic compound and a metal or metal compound as an electron injection layer.

[0044] Alternatively, another aspect of the present invention is a light-emitting device that uses the above-mentioned organic compound and an organic compound having at least one of a pyridine skeleton and a diazine skeleton, preferably a phenanthroline skeleton, for an electron injection layer.

[0045] Alternatively, another aspect of the present invention is a light-emitting device having an electron injection layer comprising the above-mentioned organic compound, an organic compound having at least one of a pyridine skeleton and a diazine skeleton, preferably a phenanthroline skeleton, and a metal or a metal compound.

[0046] Alternatively, another aspect of the present invention is a display device comprising the light-emitting device described in any of the above.

[0047] Alternatively, another aspect of the present invention is an electronic device having the above-mentioned light-emitting device and a sensor, an operating button, a speaker, or a microphone.

[0048] Alternatively, another aspect of the present invention is a lighting device having the above-mentioned light-emitting device and a housing.

[0049] In one aspect of the present invention, a novel organic compound can be provided. Alternatively, in one aspect of the present invention, a novel organic compound having electron transport properties can be provided. Alternatively, in one aspect of the present invention, a novel organic compound that can be used as an intermediate layer in a tandem light-emitting device can be provided. Alternatively, in one aspect of the present invention, an organic compound can be provided that enables the fabrication of a light-emitting device with good properties, even if the device is processed using lithography.

[0050] Alternatively, one aspect of the present invention can provide a light-emitting device with good characteristics. Alternatively, one aspect of the present invention can provide a light-emitting device with good reliability. Alternatively, one aspect of the present invention can provide a light-emitting device with a low drive voltage. Alternatively, one aspect of the present invention can provide a light-emitting device that is reliable and has a low drive voltage.

[0051] Alternatively, in one aspect of the present invention, a light-emitting device capable of providing a display device with good characteristics can be provided. Alternatively, in one aspect of the present invention, a light-emitting device capable of manufacturing a reliable display device can be provided. Alternatively, in one aspect of the present invention, a display device with a low drive voltage can be provided. Alternatively, in one aspect of the present invention, a display device with a low drive voltage and good reliability can be provided.

[0052] Furthermore, the description of these effects does not preclude the existence of other effects. Moreover, one aspect of the present invention does not necessarily have to possess all of these effects. Other effects will naturally become apparent from the description in the specification, drawings, and claims, and it is possible to extract other effects from the description in the specification, drawings, and claims.

[0053] Figures 1A, 1B, and 1C are schematic diagrams of a light-emitting device according to one embodiment of the present invention. Figures 2A and 2B are diagrams representing a display device according to one embodiment of the present invention. Figures 3A and 3B are diagrams representing a display device according to one embodiment of the present invention. Figures 4A, 4B, 4C, 4D, and 4E are cross-sectional views showing an example of a method for manufacturing a display device. Figures 5A and 5B are cross-sectional views showing an example of a method for manufacturing a display device. Figures 6A, 6B, 6C, and 6D are cross-sectional views showing an example of a method for manufacturing a display device. Figures 7A, 7B, and 7C are cross-sectional views showing an example of a method for manufacturing a display device. Figures 8A, 8B, and 8C are cross-sectional views showing an example of a method for manufacturing a display device. Figures 9A, 9B, and 9C are cross-sectional views showing an example of a method for manufacturing a display device. Figures 10A and 10B are perspective views showing an example of the configuration of a display module. Figures 11A and 11B are cross-sectional views showing an example of the configuration of a display device. Figure 12 is a perspective view showing an example of the configuration of a display device. Figure 13 is a cross-sectional view showing an example of the configuration of a display device. Figure 14 is a cross-sectional view showing an example of the configuration of a display device. Figures 15A, 15B, and 15C are cross-sectional views showing an example of the configuration of a display device. Figure 16 is a cross-sectional view showing an example of the configuration of a display device. Figures 17A, 17B, and 17C are cross-sectional views showing an example of the configuration of a display device. Figures 18A, 18B, 18C, and 18D are diagrams illustrating an example of a wearable device. Figures 19A, 19B, 19C, 19D, 19E, and 19F are diagrams showing an example of an electronic device. Figures 20A, 20B, 20C, 20D, 20E, 20F, and 20G are diagrams showing an example of an electronic device. Figures 21A, 21B, and 21C are diagrams showing the 1H NMR spectrum of Acu2Phen. Figure 22 is a diagram showing the luminance-current density characteristics of the light-emitting device 1. Figure 23 shows the current efficiency-luminance characteristics of light-emitting device 1. Figure 24 shows the luminance-voltage characteristics of light-emitting device 1. Figure 25 shows the current density-voltage characteristics of light-emitting device 1. Figure 26 shows the field emission spectrum of light-emitting device 1. Figure 27 shows the normalized luminance time variation characteristics of light-emitting device 1. Figure 28 shows the luminance-current density characteristics of light-emitting device 2. Figure 29 shows the current efficiency-luminance characteristics of light-emitting device 2.Figure 30 shows the luminance-voltage characteristics of the light-emitting device 2. Figure 31 shows the current density-voltage characteristics of the light-emitting device 2. Figure 32 shows the electroluminescence spectrum of the light-emitting device 2. Figure 33 shows the normalized luminance time variation characteristics of the light-emitting device 2.

[0054] The embodiments of the present invention will be described in detail below 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 interpreted as being limited to the contents of the embodiments shown below.

[0055] In this specification, the ordinal numbers "first," "second," etc., are used for convenience only and do not limit the number of components or the order of components. The order of components includes, for example, the order of processes or the order of stacking. That is, the ordinal numbers used in the embodiments of this specification may not match the ordinal numbers used in the claims. Also, the ordinal numbers used in the examples of this specification may not match the ordinal numbers used in the claims. Also, the ordinal numbers used in the embodiments of this specification may not match the ordinal numbers used in the examples of this specification.

[0056] Furthermore, in this specification, a photoluminescence (PL) spectrum refers to a spectrum obtained by fixing the excitation wavelength of the excitation light in fluorescence photometry and spectrally analyzing the emission from a sample irradiated with excitation light at each wavelength, and measuring the emission intensity distribution at each wavelength. It may also be called an emission spectrum. Note that an emission spectrum may contain both a fluorescent component and a phosphorescent component. In this specification, an emission spectrum consisting of a fluorescent component may be specifically called a fluorescence spectrum, and an emission spectrum consisting of a phosphorescent component may be specifically called a phosphorescent spectrum.

[0057] In this specification, devices fabricated using a metal mask or FMM (Fine Metal Mask, a high-resolution metal mask) may be referred to as MM (metal mask) structured devices. In addition, in this specification, devices fabricated without using a metal mask or FMM may be referred to as MML (metal maskless) structured devices.

[0058] (Embodiment 1) In recent years, display devices using organic EL devices have been put into practical use, and the realization of useful technologies and research and development are progressing.

[0059] For example, a tandem-type organic EL 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 conventional organic EL device that has only one light-emitting unit between electrodes.

[0060] The intermediate layer of a tandem-type organic EL device includes a Carrier Generation Layer (CGL). The CGL is a layer in which electrons and holes are generated by charge separation when a voltage is applied.

[0061] 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 a 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.

[0062] 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 underway on using photolithography to process organic compound films as an alternative to mask deposition when fabricating organic EL devices.

[0063] However, when attempting to fabricate a tandem-type light-emitting device using photolithography, it is difficult to obtain good characteristics. This is because, as mentioned above, the n-type layer of a tandem-type light-emitting device uses a material that has donor properties to electron transport materials. Typical materials used for this purpose include 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 donor properties decrease not only when directly exposed to the atmosphere, but also when exposed to the atmosphere through multiple organic compound layers. Therefore, tandem-type organic EL devices fabricated using photolithography, which requires exposing the surface of the EL layer to the atmosphere during the fabrication process, experience an increase in driving voltage, making it difficult to obtain good characteristics.

[0064] In contrast, by using a layer in the intermediate layer's n-type layer that includes a metal or metal compound and an organic compound having a phenanthroline ring with an electron-donating group, such as 4,7-di-1-pyrrolidinyl-1,10-phenanthroline (abbreviated as Pyrrd-Phen) or 4,7-di(2,3,3a,4,5,6,7,7a-octahydro-1H-isoindole-2-yl)-1,10-phenanthroline (abbreviated as Hid2Phen), a tandem-type organic EL device with good characteristics can be obtained even after undergoing a photolithography process involving exposure of the EL layer to the atmosphere (see, for example, Patent Document 2).

[0065] 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 organic EL devices.

[0066] 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-type light-emitting device, and that can provide a light-emitting device that maintains good properties as a tandem-type light-emitting device even after processing by photolithography, and that also has higher heat resistance. The organic compound has a phenanthroline skeleton, preferably a 1,10-phenanthroline skeleton, and a group containing a polycyclic alkylamine skeleton having a crosslinking structure. In this specification, a polycyclic alkylamine skeleton having a crosslinking structure refers to a skeleton having a structure in which a cycloalkyl group is fused to a monocyclic alkylamine such as pyrrolidine, and another bridge (containing at least one carbon) is connected to the cycloalkyl group.

[0067] The pyrrolidine skeleton that constitutes the electron-donating group of Pyrrd-Phen and the 2,3,3a,4,5,6,7,7a-octahydro-1H-isoindole skeleton that constitutes the electron-donating group of Hid2Phen have all single bonds between carbon atoms, making them rotatable and low in rigidity. The phenanthroline skeleton is highly rigid, so it is highly probable that these groups are influencing the relatively low heat resistance of Pyrrd-Phen and Hid2Phen.

[0068] Therefore, the present inventors have found that by using a polycyclic alkylamine skeleton having a cross-linking structure such as the 4-azatricyclo[5.2.2.0,2,6]undecane skeleton as the skeleton constituting the electron-donating group, heat resistance can be improved by inhibiting the rotation of carbon-carbon bonds and suppressing molecular vibrations of the six-membered ring portion due to temperature changes.

[0069] Thus, an organic compound according to one aspect of the present invention, by having a group containing a polycyclic alkylamine skeleton with a crosslinking structure, can increase the electron density of the nitrogen atom in the phenanthroline skeleton and improve the heat resistance of the organic compound. When the electron density of the nitrogen atom increases, its function as an electron donor in the metal or metal compound to which it coordinates improves. For this reason, an organic compound according to one aspect of the present invention can be suitably used in the n-type layer of the intermediate layer of a tandem type light-emitting device. As a result, a light-emitting device using this organic compound in the n-type layer of a tandem type light-emitting device can be made into a light-emitting device with a low driving voltage and good reliability. Thus, an organic compound having a phenanthroline ring and a group containing a polycyclic alkylamine skeleton with a crosslinking structure is suitable as a material for constituting the n-type layer in the intermediate layer of a tandem type light-emitting device.

[0070] Furthermore, in a tandem light-emitting device using an organic compound having a phenanthroline ring and a group containing a polycyclic alkylamine skeleton with a cross-linking structure as the n-type layer in the intermediate layer, as described above, the electron donor properties of the metal or metal compound contained in the n-type layer are improved. Therefore, even after going through a photolithography process that includes an air exposure process, the electron donor properties do not deteriorate significantly, making it possible to obtain an organic EL device with good characteristics.

[0071] Furthermore, while cyclic alkylamino groups such as pyrrolidine are known to be hydrophilic, the organic compound according to one aspect of the present invention has a group containing a polycyclic alkylamine skeleton with a crosslinking structure. This increases the proportion of hydrophobic carbon atoms, thereby reducing the volume ratio of the hydrophilic cyclic alkylamino group to the overall molecular structure, and thus lowering its solubility in water. For this reason, when the organic compound represented by the general formula (G1) of this application has an amino group, it is preferable that it is a cyclic secondary amino group. For these reasons, even when used in a light-emitting device manufactured in a process that includes treatment with water or a water-based chemical solution (i.e., a light-emitting device processed using lithography), it is possible to manufacture a light-emitting device with good properties and suppressed light-emitting defects.

[0072] Furthermore, the organic compound according to one embodiment of the present invention has improved heat resistance due to having a group containing a polycyclic alkylamine skeleton with a crosslinked structure. Therefore, it is possible to provide an organic EL device with good properties in which degradation is suppressed even when subjected to high-temperature heating processes or high-temperature environments. For this reason, the organic compound according to one embodiment of the present invention can be more suitably used in light-emitting devices that undergo photolithography processes requiring high-temperature processing.

[0073] In other words, an organic compound according to one aspect of the present invention is an organic compound represented by the following general formula (G1).

[0074]

[0075] However, in the organic compound represented by the above general formula (G1), R ２０ ~R ２７ At least one of the groups is represented by the following general formula (g1), and the others each independently represent hydrogen (including deuterium), a C1 to C10 alkyl group, a C3 to C10 cycloalkyl group, a C1 to C10 alkoxy group, a substituted or unsubstituted cyclic secondary amino group with 2 to 10 carbon atoms forming the ring, a substituted or unsubstituted C2 to C12 secondary amino group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.

[0076] R ２０ ~R ２７ In this case, the group represented by the following general formula (g1) is preferably 2 to 4 in number because it can increase the electron density of the nitrogen atom in the 1,10-phenanthroline skeleton, and preferably 2 in number because it has good sublimation properties. ２０ ~R ２７ In the case where there are two groups represented by the following general formula (g1), the substitution position on the phenanthroline skeleton is R ２０ and R ２７ , R ２１ and R ２６ , R ２２ and R ２５ , R ２３ and R ２４As shown above, it is preferable that the bonds are attached in positions that are symmetrical with respect to the phenanthroline skeleton, because this simplifies synthesis.

[0077] Also, R ２０ ~R ２７ In this case, it is preferable that all groups except the group represented by the following general formula (g1) are hydrogen, as this makes it easier to obtain the raw materials and reagents.

[0078] Note R ２０ ~R ２７ In this case, if there is one group represented by the following general formula (g1), then of the remaining groups, 6 are hydrogen atoms, and 1 is one of the following: 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 cyclic secondary amino group having 2 to 10 carbon atoms (substituted or unsubstituted), a secondary amino group having 2 to 12 carbon atoms (substituted or unsubstituted), an aryl group having 6 to 30 carbon atoms (substituted or unsubstituted), or a heteroaryl group having 1 to 30 carbon atoms (substituted or unsubstituted). The following are preferred because they are easy to synthesize: a cyclic secondary amino group having 2 to 10 carbon atoms forming a substituted or unsubstituted ring, a substituted or unsubstituted secondary amino group having 2 to 12 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms is chemically stable and reliable when used in light-emitting devices, and a cyclic secondary amino group having 2 to 10 carbon atoms forming a substituted or unsubstituted ring is particularly preferred because it can increase the electron density of the nitrogen atom in the phenanthroline skeleton. In particular, alkyl groups, cycloalkyl groups, and aryl groups are preferred because they are hydrophobic and thus reduce water solubility, and heteroaryl groups are preferred because they improve transportability. In this case, it is preferable that the substitution positions of groups other than hydrogen on the phenanthroline skeleton are bonded at positions symmetric to the phenanthroline skeleton with respect to the phenanthroline skeleton, for ease of synthesis.

[0079]

[0080] In the group represented by the above general formula (g1), R １ ~R １６Each of these independently represents hydrogen (including deuterium) or an alkyl group having 1 to 10 carbon atoms. It is preferable to include 1 to 4 alkyl groups having 1 to 4 carbon atoms because this improves heat resistance and reduces water solubility, and it is preferable that all of them be hydrogen because synthesis is simple.

[0081] Furthermore, s, t, u, and v each independently represent one of 0 to 3. It is preferable that s and t each be independently 1 or 2 because they are chemically stable, and even more preferable that they be 1 because they have the highest electron-donating ability. Similarly, it is preferable that u and v each be independently 1 to 3 because they improve heat resistance and reduce water solubility, and even more preferable that they be 1 because they improve properties without hindering electron transport.

[0082] In other words, the group represented by the above general formula (g1) is preferably a group represented by the following general formulas (g2) to (g4).

[0083]

[0084]

[0085]

[0086] Also, Ar １ represents a substituted or unsubstituted arylene group having 6 to 12 carbon atoms. An unsubstituted phenylene group is preferred because it has good sublimation properties. Using a p-phenylene group results in a structure where the p-phenylene group is not twisted relative to the phenanthroline ring and lies on the same plane. Therefore, the effect of the polycyclic alkylamino group having a crosslinking structure in increasing the electron density of the phenanthroline ring is less likely to decrease, which is even more preferable.

[0087] Furthermore, m represents one of 0 to 2, and when m is 2, the two substituted or unsubstituted arylene groups are either the same or different from each other. It is preferable that m is 0, as this maximizes the electron-donating ability to the nitrogen atom in the 1,10-phenanthroline skeleton.

[0088] The organic compound represented by the above general formula (G1) can be an organic compound with good electron transport properties.

[0089] Furthermore, the organic compound represented by the above general formula (G1) has a group containing a polycyclic alkylamine skeleton having a crosslinking structure represented by the above general formula (g1), thereby increasing the electron density of the nitrogen atom in the phenanthroline skeleton and improving the heat resistance of the organic compound.

[0090] When the electron density of a nitrogen atom increases, its function as an electron donor in the metal or metal compound to which it coordinates improves. Therefore, the organic compound according to one embodiment of the present invention can be suitably used in the n-type layer of the intermediate layer of a tandem light-emitting device. As a result, a light-emitting device using this organic compound in the n-type layer of a tandem light-emitting device can be made into a light-emitting device with a low driving voltage and good reliability. Thus, the organic compound represented by the above general formula (G1) is suitable as a material for constituting the n-type layer in the intermediate layer of a tandem light-emitting device.

[0091] Furthermore, in a tandem light-emitting device using the organic compound represented by the above general formula (G1) as the n-type layer in the intermediate layer, the electron donor properties of the metal or metal compound contained in the n-type layer are improved, as described above. Therefore, even after going through a photolithography process that includes an air exposure process, the electron donor properties do not deteriorate significantly, making it possible to obtain an organic EL device with good characteristics.

[0092] Furthermore, the organic compound represented by the above general formula (G1) has improved heat resistance because it contains a group comprising a polycyclic alkylamine skeleton having a crosslinked structure represented by the above general formula (g1). Therefore, it is possible to provide an organic EL device with good properties in which degradation is suppressed even when heated at high temperatures or exposed to high-temperature environments. For this reason, the organic compound represented by the above general formula (G1) can be more suitably used in light-emitting devices that have undergone a photolithography process that requires high-temperature processing.

[0093] Furthermore, in the organic compound represented by the general formula (G1) above, the group represented by (g1) is R ２０ , R ２２ , R ２５ and R ２７It is preferable that the raw materials are bound to at least one of the following, as this makes it easier to obtain the reagents.

[0094] In other words, the organic compound according to one aspect of the present invention is preferably an organic compound represented by the following general formula (G2).

[0095]

[0096] However, in the organic compound represented by the above general formula (G2), R ２０ , R ２２ , R ２５ and R ２７ At least one of the groups is represented by the general formula (g1) above, and the others each independently represent hydrogen (including deuterium), a C1 to C10 alkyl group, a C3 to C10 cycloalkyl group, a C1 to C10 alkoxy group, a substituted or unsubstituted cyclic secondary amino group with 2 to 10 carbon atoms forming the ring, a substituted or unsubstituted C2 to C12 secondary amino group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.

[0097] R ２０ , R ２２ , R ２５ and R ２７ In particular, the group represented by the above general formula (g1) is preferably two or more because it can increase the electron density of the nitrogen atom in the 1,10-phenanthroline skeleton, and is preferably two because it has good sublimation properties. ２０ , R ２２ , R ２５ and R ２７ In the case where there are two groups represented by the above general formula (g1), the substitution position on the phenanthroline skeleton is R ２０ and R ２７ , R ２２ and R ２５ As shown above, it is preferable that the bonds are attached in positions that are symmetrical with respect to the phenanthroline skeleton, because this simplifies synthesis.

[0098] Also, R ２０ ~R ２７In this case, it is preferable that all groups other than the group represented by the general formula (g1) above are hydrogen, because the raw materials for the reagents are readily available.

[0099] Note R ２０ , R ２２ , R ２５ and R ２７ In this case, if there is one group represented by the above general formula (g1), then of the remaining groups, two are hydrogen atoms, and one is one of the following: 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 cyclic secondary amino group having 2 to 10 carbon atoms (substituted or unsubstituted), a secondary amino group having 2 to 12 carbon atoms (substituted or unsubstituted), an aryl group having 6 to 30 carbon atoms (substituted or unsubstituted), or a heteroaryl group having 1 to 30 carbon atoms (substituted or unsubstituted). The following are preferred because they are easy to synthesize: a cyclic secondary amino group having 2 to 10 carbon atoms forming a substituted or unsubstituted ring, a substituted or unsubstituted secondary amino group having 2 to 12 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, which are chemically stable and reliable when used in light-emitting devices, and especially preferred because they are cyclic secondary amino groups having 2 to 10 carbon atoms forming a substituted or unsubstituted ring, which are chemically stable and reliable when used in light-emitting devices. In particular, alkyl groups, cycloalkyl groups, and aryl groups are preferred because they are hydrophobic and thus reduce water solubility, and heteroaryl groups are preferred because they improve transportability. In this case, it is preferable that the substitution positions of groups other than hydrogen on the phenanthroline skeleton are bonded at positions symmetrical with respect to the phenanthroline skeleton, for ease of synthesis.

[0100] Furthermore, in the organic compound represented by the general formula (G1) above, the group represented by (g1) is R ２０ , R ２２ , R ２５ and R ２７ It is preferable that at least one of these is bonded, as this can increase the electron density of the nitrogen atom in the 1,10-phenanthroline skeleton.

[0101] In other words, the organic compound according to one aspect of the present invention is preferably an organic compound represented by the following general formula (G3).

[0102]

[0103] However, in the organic compound represented by the above general formula (G3), R ２２ and R ２５ At least one of the groups is represented by the general formula (g1) above, and the others each independently represent hydrogen (including deuterium), a C1 to C10 alkyl group, a C3 to C10 cycloalkyl group, a C1 to C10 alkoxy group, a substituted or unsubstituted cyclic secondary amino group with 2 to 10 carbon atoms forming the ring, a substituted or unsubstituted C2 to C12 secondary amino group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.

[0104] Note R ２２ and R ２５ It is preferable that both of the groups are represented by the above general formula (g1) because this maximizes the electron density of the nitrogen atom in the 1,10-phenanthroline skeleton.

[0105] Note R ２２ and R ２５In the synthesis, if there is one group represented by the above general formula (g1), the remaining one is one of the following: 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 cyclic secondary amino group having 2 to 10 carbon atoms (substituted or unsubstituted), a secondary amino group having 2 to 12 carbon atoms (substituted or unsubstituted), an aryl group having 6 to 30 carbon atoms (substituted or unsubstituted), or a heteroaryl group having 1 to 30 carbon atoms (substituted or unsubstituted). It is preferable for simplicity, and it is even more preferable for chemical stability and good reliability when used in light-emitting devices that the substituted or unsubstituted ring is a cyclic secondary amino group with 2 to 10 carbon atoms, a substituted or unsubstituted secondary amino group with 2 to 12 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 30 carbon atoms. In particular, alkyl groups, cycloalkyl groups, and aryl groups are preferred because they are hydrophobic and thus reduce water solubility, and heteroaryl groups are preferred because they improve transportability.

[0106] Specific examples of the group represented by the above general formula (g1) include the groups represented by the following structural formulas (g1-1) to (g1-163).

[0107]

[0108]

[0109]

[0110]

[0111] Furthermore, in the above general formulas (G1) to (G3), the alkyl groups having 1 to 10 carbon atoms include, for example, 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 Examples of methyl groups include 2-ethylbutyl group, 1,2-dimethylbutyl group, and 2,3-dimethylbutyl group, 2-ethylhexyl group, 1-ethylpropyl group, heptyl group, octyl group, 3-methylpentyl group, 2-methylpentyl group, 2-ethylbutyl group, 1,2-dimethylbutyl group, and 2,3-dimethylbutyl group, nonyl group, 3,7-dimethyl-1-octyl group, 3,7-dimethyl-2-octyl group, and decyl group.

[0112] In the above general formulas (G1) to (G3), examples of cycloalkyl groups having 3 to 10 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-methylcyclohexyl, cycloheptyl, 1-adamantyl, and 2-adamantyl groups.

[0113] Furthermore, in the above general formulas (G1) to (G3), examples of alkoxy groups having 1 to 10 carbon atoms include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, isobutoxy group, tert-butoxy group, n-pentyloxy group, isopentyloxy group, sec-pentyloxy group, tert-pentyloxy group, neopentyloxy group, n-hexyloxy group, isohexyloxy group, sec-hexyloxy group, tert-hexyloxy group, neohexyloxy group, cyclohexyloxy group, and the like.

[0114] Furthermore, in the above general formulas (G1) to (G3), examples of aryl 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, triphenylenyl group, and the like. Furthermore, if the aryl group having 6 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, or aryl groups having 6 to 13 carbon atoms.

[0115] Furthermore, in the above general formulas (G1) to (G3), examples of heteroaryl groups having 1 to 30 carbon atoms include pyridine-yl group, pyrimidine-yl group, triazine-yl group, phenanthroline-yl group, carbazole-yl group, pyrrole-yl group, thiophene-yl group, furan-yl group, imidazole-yl group, bipyridine-yl group, bipyrimidine-yl group, pyrazine-yl group, bipyrazine-yl group, quinoline-yl group, isoquinoline-yl group, benzoquinoline-yl group, quinoxaline-yl group, benzoquinoxaline-yl group, dibenzoquinoxaline-yl group, azofluoren-yl group, diazofluoren-yl group, benzocarbazole-yl group, dibenzocarbazole-yl group, dibenzofuran-yl group, benzonaphthofuran-yl group, and di Examples of these groups include naphthofuranyl group, dibenzothiophenyl group, benzonaphthothiophenyl group, dinaphthothiophenyl group, benzoflopyridineyl group, benzoflopyrimidineyl group, benzothiopyrimidineyl group, benzothiopyrimidineyl group, naphthoflopyridineyl group, naphthothiopyrimidineyl group, naphthothiopyrimidineyl group, dibenzoquinoxalineyl group, acridineyl group, xantheneyl group, phenothiazineyl group, phenoxazineyl group, phenazineyl group, triazoleyl group, oxazoleyl group, oxadiazoleyl group, thiazoleyl group, thiadiazoleyl group, benzimidazoleyl group, or pyrazoleyl 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, or aryl groups having 6 to 13 carbon atoms.

[0116] Furthermore, in the above general formulas (G1) to (G3), the secondary amino group having 2 to 12 carbon atoms is preferably a cyclic secondary amine, such as a dimethylamino group, diethylamino group, diisopropylamino group, diphenylamino group, or dicyclohexylamino group. When the cyclic secondary amino group having 2 to 10 carbon atoms has substituents, the 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.

[0117] Furthermore, in the above general formulas (G1) to (G3), the cyclic secondary amino group having 2 to 10 carbon atoms represents a monovalent group obtained by removing hydrogen from the nitrogen atom of a cyclic secondary amine having 2 to 10 carbon atoms. Specific examples of cyclic secondary amino groups having 2 to 10 carbon atoms include 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, and octahydro-4,7-methano-1H-isoindoyl Examples include the lu-2-yl group, 2-azabicyclo[3.1.0]hexane-2-yl group, 3-azabicyclo[3.1.0]hexane-2-yl group, 3-azabicyclo[3.2.0]heptan-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]heptan-7-yl group, 5-azabispiro[2.4]heptan-5-yl group, and 5-azabicyclo[2.1.1]hexane-5-yl group. When a cyclic secondary amino group having 2 to 10 carbon atoms has substituents, examples of such substituents include alkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, and substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.

[0118] In the above general formulas (G1) to (G3), as the cyclic secondary amino group having 2 to 10 carbon atoms constituting a substituted or unsubstituted ring, groups represented by the following general formula (g2-1) and the following general formula (g2-2) are preferred because of their high electron-donating property.

[0119]

[0120] Provided that in the above general formula (g2-1) and general formula (g2-2), R ３１ to R ３８ , and R ４１ to R ４６ each independently represent any one of hydrogen (including deuterium), 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, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. In addition, p and q each independently represent an integer of 0 to 2.

[0121] As the cyclic secondary amino group having 2 to 10 carbon atoms constituting a substituted or unsubstituted ring, groups represented by the following structural formulas (A-1) to (A-9) are more preferred because the raw materials are easily available.

[0122]

[0123] In addition, in the above general formulas (G1) to (G3), examples of the arylene group having 6 to 12 carbon atoms include a phenylene group, a biphenyl-diyl group, a naphthalene-diyl group, and the like. When the arylene group having 6 to 12 carbon atoms has a substituent, examples of the substituent include an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and an aryl group having 6 to 13 carbon atoms.

[0124] Examples of the organic compound according to one embodiment of the present invention represented by any one of the above general formulas (G1) to (G3) include organic compounds represented by the following structural formulas (100) to (146).

[0125]

[0126]

[0127]

[0128]

[0129] Next, as an example of the organic compound according to one embodiment of the present invention, a method for synthesizing an organic compound represented by the following general formula (G1) will be described. Note that various reactions can be applied as the synthesis method for general formula (G1), and the synthesis method is not limited to the following.

[0130]

[0131] Provided that in the organic compound represented by the above general formula (G1), R ２０ to R ２７ at least one of which is a group represented by the following general formula (g1), and the others each independently represent hydrogen (including deuterium), 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 substituted or unsubstituted cyclic secondary amino group having 2 to 10 carbon atoms, a substituted or unsubstituted secondary amino group having 2 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms. Further, in the group represented by the above general formula (g1), R １ to R １６ each independently represent hydrogen (including deuterium) or an alkyl group having 1 to 10 carbon atoms, s, t, u and v each independently represent any one of 0 to 3. Further, Ar １ represents a substituted or unsubstituted arylene group, m represents any one of 0 to 2, and when m is 2, the two substituted or unsubstituted arylene groups may be the same as or different from each other.

[0132] The organic compound represented by general formula (G1) can be synthesized by a simple synthesis scheme such as the following synthesis scheme (A-1).

[0133]

[0134] In the above phenanthroline derivative (a1), X ２０ to X ２７At least one of these groups is a halogen or a trifluoromethanesulfonyl group. The others each independently represent hydrogen (including deuterium), a C1 to C10 alkyl group, a C3 to C10 cycloalkyl group, a C1 to C10 alkoxy group, a substituted or unsubstituted C2 to C10 cyclic secondary amino group, a substituted or unsubstituted C2 to C12 secondary amino group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.

[0135] In the polycyclic alkylamine derivative (a2) having the above crosslinked structure, Q is hydrogen when m is 0, and a boronyl group (-B(OH) when m is 1 or greater) ２ ) represents R １ ~R １６ s, t, u and v, Ar １ This is the same as the general formula (g1). Note that when using a boronyl group, boronic acid esters or cyclic triol borate salts may also be used.

[0136] In the synthesis scheme (A-1), if m is 0 in the polycyclic alkylamine derivative (a2) having the crosslinked structure, an organic compound represented by general formula (G1) can be obtained by nucleophilic substitution reaction between the phenanthroline derivative (a1) and the polycyclic alkylamine derivative (a2) having the crosslinked structure, in which the halogen or trifluoromethanesulfonyl group of the phenanthroline derivative represented by general formula (a1) is replaced with the group represented by general formula (g1).

[0137] 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 diazabicycloundecene (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.

[0138] 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 an organic base is used, it may be used as both a base and a solvent.

[0139] 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.

[0140] In the synthesis scheme (A-1), if m is 1 or greater, the phenanthroline derivative (a1) and the phenanthroline derivative (a2) having the crosslinked structure can be coupled by the Suzuki-Miyaura reaction to obtain an organic compound represented by general formula (G1) in which the halogen or trifluoromethanesulfonyl group of the phenanthroline derivative represented by general formula (a1) is replaced by the group represented by general formula (g1).

[0141] 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, trisdibenzylideneacetonedipalladium(O), and the like.

[0142] Ligands for the above palladium catalyst include 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, di(1-adamantyl)-N-butylphosphine, (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, tri(ortho-tolyl)phosphine, triphenylphosphine, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (abbreviated as Xantphos), tricyclohexylphosphine, and the like.

[0143] 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.

[0144] 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.

[0145] 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.

[0146] While organic compounds according to one embodiment 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.

[0147] This embodiment can be used in any combination with other embodiments and examples.

[0148] An organic compound comprising a phenanthroline ring and a polycyclic alkylamine skeleton having a crosslinking structure according to one aspect of the present invention can be synthesized as described above.

[0149] This embodiment can be used in any combination with other embodiments.

[0150] (Embodiment 2) This embodiment will describe in detail a light-emitting device according to one aspect of the present invention. Figure 1A 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 1A and 1B, 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 describe the case where the first electrode 101 functions as the anode and the second electrode 102 functions as the cathode, but this can also be reversed.

[0151] In one embodiment of the present invention, the organic compound layer 103 contains an organic compound represented by at least one of the general formulas (G1) to (G3) in Embodiment 1. Since the organic compound represented by at least one of the general formulas (G1) to (G3) 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 block layer, light-emitting layer 113, intermediate layer, etc. in the light-emitting device shown in Figures 1A and 1B.

[0152] In particular, organic compounds represented by at least one of general formulas (G1) to (G3) form coordination bonds with metals or metal compounds and improve the donor properties of the metal. Therefore, in the light-emitting devices shown in Figures 1A and 1B, 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.

[0153] Alkali metals or alkaline earth metals, or compounds thereof (hereinafter also referred to as Li compounds, etc.), are often used in the electron injection layer 115, the charge generation layer 116, and the intermediate layer. However, these Li compounds, etc., are highly reactive with water or oxygen, and the organic compound layer 103 deteriorates rapidly when exposed to the atmosphere, resulting in a significant decrease in functionality. For this reason, photolithography has been investigated as a processing method for light-emitting devices using the organic compound layer 103, but it has been difficult to obtain light-emitting devices with good characteristics using conventional light-emitting devices.

[0154] However, the electron injection layer 115, charge generation layer 116, and intermediate layer containing the organic compound represented by general formulas (G1) to (G3) disclosed in Embodiment 1 can improve the 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.

[0155] 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 formulas (G1) to (G3) 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.

[0156] 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 insulator 1000 side. However, a so-called reverse stacking configuration is also possible, in which the second electrode 102 is formed on the insulator 1000 side. In this case, the light-emitting device has a stacked structure in the following order from the insulator 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), and 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.

[0157] Furthermore, the first electrode 101 and the second electrode 102 may be formed as a single-layer structure or a laminated structure. If they have a laminated structure, the layer in contact with the organic compound layer 103 functions as the anode or cathode. When the electrodes have a laminated 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.

[0158] The anode is preferably formed using a metal, alloy, conductive compound, or mixture thereof with a large work function (specifically, 4.0 eV or more). 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 containing tungsten oxide and zinc oxide (IWZO) can also be formed by sputtering using a target containing 0.5 to 5 wt% tungsten oxide and 0.1 to 1 wt% zinc oxide relative to indium oxide. 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 laminated on Ti is preferred 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.

[0159] 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 contains phthalocyanine (abbreviated as H ２It can be formed from phthalocyanine compounds or complex compounds such as Pc, copper phthalocyanine (abbreviated as CuPc), aromatic amine compounds such as 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), or polymers such as poly(3,4-ethylenedioxythiophene) / polystyrene sulfonic acid (abbreviated as PEDOT / PSS).

[0160] 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-hexaazatriphenylene (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 complex atoms, such as HAT-CN, are thermally stable and therefore preferred. Furthermore, [3]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 substances that can be used include transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide. Furthermore, phthalocyanine (abbreviation: H) can also be used. ２The hole injection layer 111 can also be formed by phthalocyanine compounds or complex compounds such as Pc, copper phthalocyanine (abbreviated as CuPc), aromatic amine compounds such as 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), 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.

[0161] 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.

[0162] 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 1 / Vs or higher. 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.

[0163] 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.

[0164] 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), 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'-spirobi[9H-fluorene]-2-amine (abbreviation: BBASF), N,N-bis(biphenyl-4-yl)-9,9'-spirobi[9H-fluorene]-4-amine (abbreviation: BBASF(4)), N-(biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobi[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: PCBi1BP), 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'-spirobi-9H-fluoren-3-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-2-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-1-amine, 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).

[0165] 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).

[0166] 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.

[0167] 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.

[0168] The hole transport layer 112 is formed by including a material that has hole transport properties. The material that has hole transport properties is 1 × 10 −６ cm ２ It is preferable that the hole mobility is greater than or equal to / Vs.

[0169] The hole transport layer 112 may be a single-layer structure or a 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.

[0170] 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.

[0171] 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: PCBi1BP), 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-carbazole-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9'-spirobi[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), 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: βNCBP), 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 phenylen-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'-spirobi-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.

[0172] The light-emitting layer 113 is a layer containing a light-emitting central material. It is also preferable that it contains a host material.

[0173] The luminescent central material may be a fluorescent material, a phosphorescent material, a thermally activated delayed fluorescence (TADF) material, or any other luminescent material.

[0174] 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.

[0175] 5,6-bis[4-(10-phenyl-9-antryl)phenyl]-2,2'-bipyridine (abbreviation: PAPP2BPy), 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: 2YGAAPPA), 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 to[1,2-d]furan)-8-amine] (abbreviation: 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 (abbreviation: 3,10PCA2Nbf(IV)-02), and 3,10-bis[N-(dibenzofuran-3-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10FrA2Nbf(IV)-02). In particular, condensed aromatic diamine compounds, such as pyrenediamine compounds like 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6BnfAPPrn-03, are preferred because they exhibit high hole-trapping properties and excellent luminescence efficiency or reliability.

[0176] 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 diazaboranaphtho-anthracene skeleton, can be suitably used because they produce blue emission with a narrow emission spectrum and good color purity.

[0177] In addition to these, 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]benzazaborino[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)indro[3,2,1-de]indro[3',2',1':8,1][1,4]benzazavolino[2,3,4-kl]phenazavolin (abbreviation: BBCz-Y), can be suitably used.

[0178] 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.

[0179] Tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazole-3-yl-κN2]phenyl-κC}Iridium(III) (Abbreviation: [Ir(mpptz-dmp) ３ ]), Tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazolato) iridium (III) (abbreviation: [Ir(Mptz) ３ ]), organometallic iridium complexes having a 4H-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 ]) an organometallic iridium complex having a 1H-triazole skeleton, such as fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpim) ３]), Tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridine]iridium(III) (abbreviation: [Ir(dmpimpt-Me) ３ ]), organometallic iridium complexes having an imidazole skeleton such as tris(2-{1-[2,6-bis(1-methylethyl)phenyl]-1H-imidazole-2-yl-κN3}-4-cyanophenyl-κC) iridium(III) (abbreviation: CNImIr), tris[(6-tert-butyl-3-phenyl-2H-imidazol[4,5-b]pyrazine-1-yl-κC2)phenyl-κC] iridium(III) (abbreviation: [Ir(cb) ３ Organometallic complexes having a benzimidazolidene skeleton such as ]), 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(CF) ３ ppy) 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 (abbreviated as 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) (abbreviated as PtON-TBBI). These compounds exhibit phosphorescence with a blue hue 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.

[0180] 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)), (acetylacetonate)bis[6-(2-norbornyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(nbppm) ２ (acac)), (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(mpmpppm) ２ (acac)), (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm) ２ Organometallic iridium complexes having a pyrimidine skeleton such as (acac) (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 Organometallic iridium complexes having a pyrazine skeleton such as (acac), Tris(2-phenylpyridinato-N,C) ２’ Iridium (III) (abbreviation: [Ir(ppy) ３ ]), bis(2-phenylpyridinate-N,C ２’ Iridium (III) acetylacetonate (abbreviation: [Ir(ppy) ２ (acac)), bis(benzo[h]quinolinate)iridium(III)acetylacetonate (abbreviation: [Ir(bzq) ２(acac)), Tris(benzo[h]quinolinate) Iridium(III) (abbreviation: [Ir(bzq) ３ ]), Tris(2-phenylquinolinato-N,C) ２’ Iridium (III) (abbreviation: [Ir(pq) ３ ]), bis(2-phenylquinolinato-N,C ２’ Iridium(III) acetylacetonate (abbreviation: [Ir(pq) ２ (acac)]), [2-d3-methyl-8-(2-pyridinyl-κN)benzofl[2,3-b]pyridine-κC]bis[2-(5-d ３ [Methyl-2-pyridinyl-κN2)phenyl-κC]iridium(III) (abbreviation: Ir(5mppy-d) ３ ) ２ (mbfpypy-d ３ )), {2-(methyl-d ３ )-8-[4-(1-methylethyl-1-d)-2-pyridinyl-κN]benzofl[2,3-b]pyridin-7-yl-κC]bis{5-(methyl-d ３ )-2-[5-(methyl-d ３ )-2-pyridinyl-κN]phenyl-κC}iridium(III) (abbreviation: Ir(5mtpy-d6) ２ (mbfpypy-iPr-d ４ )), [2-(methyl-d ３ )-8-(2-pyridinyl-κN)benzofloxacin[2,3-b]pyridinyl-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(ppy) ２ (mbfpypy-d ３ )), [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-d ３ [methyl-5-phenyl-2-pyridinyl-κN2)phenyl-κC]bis[2-(5-d ３ [Iridium (III) (abbreviation: [Ir(5mppy-d)])(methyl-2-pyridinyl-κN2)phenyl-κC) ３ )2(mdppy-d３ ) )]), [2-methyl-8-(2-pyridinyl-κN)benzofl[2,3-b]pyridine-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(ppy) ２ (mbfpypy)), Tris{2-[5-(methyl-d3)-4-phenyl-2-pyridinyl-κN]phenyl-κC}Iridium(III) (abbreviation: Ir(5m4dppy-d ３ ) ３ In addition to organometallic iridium complexes with a pyridine skeleton such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [Tb(acac) ３ Rare earth metal complexes such as (Phen) (2-{1-(5-tert-butylbiphenyl-2-yl)-4-[3-tert-butyl-5-(4-phenyl-2-pyridinyl-κN)phenyl-κC6]-2-benzimidazolyl-κN3}-4,6-di-tert-butylphenolate-κO)platinum(II) (abbreviation: Pt(tBudpppymmtBubiz-tBubp) Examples of organometallic platinum complexes include [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)phenolato-κO]platinum(II) (abbreviation: Pt(4tButpppypyp-mmtBup)). These compounds mainly exhibit phosphorescence with a green hue and have emission peaks in the wavelength range from 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.

[0181] Also, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir(5mdppm) ２ (dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm) ２(dpm)]), bis[4,6-di(naphthalene-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(d1npm) ２ Organometallic iridium complexes having a pyrimidine skeleton such as (dpm)]), (acetylacetonato)bis(2,3,5-triphenylpyradinato)iridium(III) (abbreviation: [Ir(tppr) ２ (acac)), bis(2,3,5-triphenylpyrazinate)(dipivaloylmethanato) iridium(III) (abbreviation: [Ir(tppr) ２ (dpm)]), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq) ２ Organometallic iridium complexes having a pyrazine skeleton such as (acac), 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 In addition to organometallic iridium complexes with a pyridine skeleton such as [-κC]iridium(III), there are platinum complexes such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP), and tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: [Eu(DBM)] ３ (Phen)]), Tris[1-(2-tenoyl)-3,3,3-trifluoroacetonate](monophenanthroline) europium(III) (abbreviation: [Eu(TTA) ３Examples include rare earth metal complexes such as (Phen)). These compounds exhibit phosphorescent emission with a red hue and have emission peaks in the wavelength range of 600 nm to 700 nm. In addition, 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.

[0182] In addition to the phosphorescent compounds described above, other known phosphorescent compounds may be selected and used.

[0183] 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. As a metal-containing porphyrin, for example, the protoporphyrin-tin fluoride complex (SnF) shown in the following structural formula is used. ２ (Proto IX)), Mesoporphyrin-Tin Fluoride Complex (SnF ２ (Meso IX), hematoporphyrin-tin fluoride complex (SnF ２ (Hemato IX), coproporphyrin tetramethyl ester-tin fluoride complex (SnF ２ (Copro III-4Me)), Octaethylporphyrin-Tin Fluoride Complex (SnF ２ (OEP)), Ethioporphyrin-Tin Fluoride Complex (SnF ２ (Etio I)), Octaethylporphyrin-Platinum Chloride Complex (PtCl ２ OEP (Open Economic Programme) and others can also be mentioned.

[0184]

[0185] Furthermore, the following structural formulas represent 2-(biphenyl-4-yl)-4,6-bis(12-phenylindoro[2,3-a]carbazole-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ), 9-(4,6-diphenyl-1,3,5-triazine-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzTZn), 2-{4-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-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-dihydrophenadin-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.

[0186]

[0187] Furthermore, a TADF material in which the singlet excited state and the triplet excited state are in thermal equilibrium may be used as the TADF material. 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.

[0188]

[0189] 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.

[0190] 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.

[0191] Furthermore, the phosphorescence spectrum observed at low temperatures (for example, from 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 the S1 level and the T1 level is 0.3 eV or less, and more preferably 0.2 eV or less.

[0192] 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.

[0193] 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.

[0194] 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.

[0195] 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.

[0196] 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: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBi1BP), 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'-spirobi[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'-spirobi-9H-fluoren-1-amine, 9-[3-(triphenylsilyl)phenyl]-3,Compounds having 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), 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. Furthermore, it is more preferable to use organic compounds having an amine skeleton or a fluorene skeleton. Furthermore, organic compounds having amine and fluorene skeletons are preferred because they are highly reliable and have high hole transport properties, thereby reducing the power consumption of light-emitting devices.

[0197] 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 x 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.

[0198] Examples of electron-transporting materials include bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviated as BeBq). ２Preferably, metal complexes such as bis(2-methyl-8-quinolinolato)(4-phenylphenololato)aluminum(III) (abbreviated as BAlq), bis(8-quinolinolato)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazollyl)phenololato]zinc(II) (abbreviated as ZnPBO), and bis[2-(2-benzothiazolyl)phenololato]zinc(II) (abbreviated as ZnBTZ), and organic compounds having a π-electron-deficient heteroaromatic ring are preferred. 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.

[0199] 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 acceptor properties and good reliability.

[0200] 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 Organic compounds having an azole skeleton such as CO11), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), 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-phenan Organic compounds containing heteroaromatic rings with a pyridine skeleton, such as throline (abbreviation: mTpPPhen), 2-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-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]Quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]Quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(9H-carbazole-9-yl)biphenyl-3-yl]dibenzo[f,h]Quinoxaline (abbreviation: 2mCzBPDBq), 2-[4'-(9-phenyl-9H-carbazole-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), 2-{3-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-9-yl]phenyl}dibenzo[f,h]quinoxaline Noxaline (abbreviation: 2mPCCzPDBq), 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-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(dibenzothio [Phen-4-yl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6-bis[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-(dibenzo [4-(2-naphthyl)phenyl]-[1]benzoflozyrimidine (abbreviation: 8(βN2)-4mDBtPBfpm), 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-f Phenylpyrimidine (abbreviation: 6mBP-4Cz2PPm), 2,6-bis(4-naphthalene-1-ylphenyl)-4-[4-(3-pyridyl)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 Organic compounds having a diazine skeleton such as −(p-terphenyl-3-yl)−4-[3-(dibenzothiophen-4-yl)phenyl]−[1]benzoflou[3,2-d]pyrimidine (abbreviation: 8mpTP-4mDBtPBfpm), 11-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]phenantro[9',10':4,5]flou[2,3-b]pyrazine (abbreviation: 11mDBtBPPnfpr), 2-(biphenyl-4-yl)−4-phenyl-6-(9,9'-spirobio[9H-fluorene]-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- [Iyl]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-phenylindoro[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), 2,4,6-tris(2-pyridyl)-1,3,5-triazine (abbreviation: 2Py3Tzn), 11-[4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine-2-yl]-11,12-dihydro-12-(biphenyl-3-yl)in Dro[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-6-(9-phenyl-3-dibenzofuranyl)-1, 3,5-triazine-2-yl]-9H-carbazole (abbreviation: PDBf-PCzTZn), 9-[4-(4,6-diphenyl-1,3,5-triazine-2-yl)-2-dibenzothienyl]-2-phenyl-9H-carbazole (abbreviation: PCzDBtTZn), 2,4-diphenyl-6-[3'-(spiro[7H-benzo[c]fluoren-7,9'-[9H]xanthene]-2'-yl)biphenyl-3-yl]-1,3,5-triazine (abbreviation: mSbfxBPTZn), 3'-[4-phenyl-6-(spiro[9H-fluoren-9,Examples of organic compounds containing heteroaromatic rings having a triazine skeleton include 9'-[9H]xanthene]-2'-yl)-1,3,5-triazine-2-yl]biphenyl-4-carbonitrile (abbreviated as mpCNBP-SFxTZn) and 2,2'-[1,2-naphthalenediyldi(4,1-phenylene)]bis(4,6-diphenyl-1,3,5-triazine) (abbreviated as TZnP2N). 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.

[0201] Furthermore, the organic compounds represented by general formulas (G1) to (G3) disclosed in Embodiment 1 can also be suitably used as host materials having electron-transporting properties. By using the organic compounds represented by general formulas (G1) to (G3) disclosed in Embodiment 1 as host materials having electron-transporting properties, phosphorescent compounds with wavelengths longer than green can be emitted.

[0202] 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.

[0203] This is very effective when the above-mentioned luminescent material is a fluorescent luminescent material. Also, in order to obtain high luminescence efficiency in this case, the S of the TADF material １ The energy level is S of the fluorescent material. １ It is preferable that the level be higher than the level. Also, the T of the TADF material １ The energy level is S of the fluorescent material. １It is preferable that the level be higher than the level of the TADF material. １ The energy level is the T of the fluorescent material. １ A level higher than the current level is preferable.

[0204] 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 a smooth transfer of excitation energy from the TADF material to the fluorescent material, resulting in efficient emission.

[0205] 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, saturated hydrocarbons, specifically alkyl groups having 3 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 carbon atoms, and trialkylsilyl groups having 3 to 10 carbon atoms. It is even more preferable to have multiple protecting groups. Substituents without π bonds have poor carrier transport function, and therefore can increase the distance between the TADF material and the luminescent phosphoform of the fluorescent 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.

[0206] 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 into 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 host material 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 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. Also, it is preferable to include a dibenzofuran skeleton because reliability can be ensured without lowering the T1 level.

[0207] Examples of such substances include 9-phenyl-3-[4-(10-phenyl-9-antryl)phenyl]-9H-carbazole (abbreviated as PCzPA), 3-[4-(1-naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviated as PCPN), 9-[4-(10-phenyl-9-antryl)phenyl]-9H-carbazole (abbreviated as CzPA), and 7-[4-(10-phenyl-9-antryl) Phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl]benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-[4-(9-phenyl-9H-fluoren-9-yl)biphenyl-4'-yl]anthracene (abbreviation: FLPPA), 9-(1-naphthyl)-10-[4-(2 -Naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth), 9-(1-naphthyl)-10-(2-naphthyl)anthracene (abbreviation: α,βADN), 2-(10-phenylanthracene-9-yl)dibenzofuran, 2-(10-phenyl-9-antryl)benzo[b]naphtho[2,3-d]furan (abbreviation: Bnf(II)PhA), 9-(2-naphthyl)-10-[3-(2-naphthyl) Examples include [phenyl]anthracene (abbreviated as βN-mβNPAnth), 1-{4-[10-(biphenyl-4-yl)-9-anthryl]phenyl}-2-ethyl-1H-benzimidazole (abbreviated as EtBImPBPhA), and 7-(phenyl-2,3,4,5,6-d5)-1-[10-(phenyl-2,3,4,5,6-d5)-9-anthryl]dibenzofuran (abbreviated as PDBfPhA-d10). In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA are preferred choices because they exhibit very good properties.

[0208] 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 should be 1:19 to 19:1.

[0209] 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.

[0210] 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.

[0211] Furthermore, at least one of the materials forming the excitation complex may be a phosphorescent material. This allows for the efficient conversion of the triplet excitation energy to the singlet excitation energy through reverse intersystem crossing.

[0212] 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).

[0213] 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 may be read as 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.

[0214] The electron transport layer 114 is a layer containing an electron-transporting material. The electron-transporting material has an electron mobility of 1 × 10⁻¹⁶ at an electric field strength [V / cm] square root of 600. −７ cm ２ / Vs or more, preferably 1 x 10 −６ cm ２ A substance having an electron mobility of 1 / 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.

[0215] 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.

[0216] 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, organic compounds containing a heteroaromatic ring having a pyridine skeleton, and organic compounds containing 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 and organic compounds containing a heteroaromatic ring having a triazine skeleton have high electron transport properties and contribute to reducing the driving voltage. In particular, organic compounds having a phenanthroline skeleton such as mTpPPhen, PnNPhen, and mPPhen2P are preferred, and organic compounds having a phenanthroline dimer structure such as mPPhen2P are more preferred due to their superior stability.

[0217] Furthermore, the organic compounds represented by general formulas (G1) to (G3) disclosed in Embodiment 1 can also be suitably used in the electron transport layer 114. By using the organic compounds represented by general formulas (G1) to (G3) 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 compounds represented by general formulas (G1) to (G3) disclosed in Embodiment 1 have high electron transport properties and contribute to reducing the driving voltage.

[0218] The electron transport layer 114 may have a laminated structure. Furthermore, the layer in contact with the light-emitting layer 113 in the laminated 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.

[0219] 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) (abbreviated as hpp2Py). The electron injection layer 115 may also be a layer containing these materials within a layer made of an electron-transporting substance.

[0220] Furthermore, it is preferable that the electron injection layer 115 contains an organic compound represented by general formulas (G1) to (G3) disclosed in Embodiment 1. By including the organic compound represented by general formulas (G1) to (G3) disclosed in Embodiment 1, the electron injection properties are improved, and a light-emitting device with a low driving voltage can be made possible. In addition, the electron injection layer 115 containing the organic compound represented by general formulas (G1) to (G3) disclosed in Embodiment 1 can improve the donor properties of the metal or metal compound by coordinating with the metal or metal compound. As a result, even if the electron injection layer 115 is exposed to an atmospheric environment, the impairment of the function of the electron injection layer 115 can be suppressed, thereby suppressing the rise in driving voltage and making it possible to provide a light-emitting device with good characteristics.

[0221] The electron injection layer may further contain a second organic compound comprising a π-electron-deficient heteroaromatic ring. The presence of this second organic compound can improve heat resistance, electron transport, and other properties.

[0222] The π-electron-deficient heteroaromatic rings of the second organic compound described above are preferably heteroaromatic rings having an azole skeleton (imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadiazole ring, thiadiazole ring), heteroaromatic rings having a pyridine skeleton, heteroaromatic rings having a diazine skeleton, and heteroaromatic rings having a triazine skeleton. Diazine rings (pyrazine ring, pyrimidine ring, pyridazine ring) or triazine rings are particularly preferred because they are electrochemically stable and have high electron transport properties.

[0223] Furthermore, the π-electron-deficient heteroaromatic ring of the second organic compound may have a fused ring structure.

[0224] As the second organic compound, an organic compound having electron-transporting properties can be used. The electron-transporting organic compound 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 x 10 −６ cm ２ A material having an electron mobility of / Vs or higher is preferred. However, other materials can also be used as long as they have higher electron transport capabilities than holes.

[0225] Specifically, as organic compounds having electron-transporting properties, the materials described above as organic compounds having a π-electron-deficient heteroaromatic ring skeleton that can be used as a host material in the light-emitting layer can also be used.

[0226] Furthermore, as the second organic compound, an organic compound having two or more heteroaromatic rings bonded or fused to each other, and in total having three or more heteroatoms among these two or more heteroaromatic rings, is particularly preferred. For example, as the organic compound used for the second organic compound, it is preferable to use an organic compound represented by the following general formula (G1-1) or general formula (G1-2).

[0227]

[0228] In the above general formula (G1-1), A １ A ２ and A ３ Each of these independently represents a substituted or unsubstituted heteroaromatic ring with 1 to 30 carbon atoms, A １ A ２ and A ３ They may form fused rings with each other.

[0229] The organic compound represented by general formula (G1-1) has a conjugated double bond in which the nitrogen atoms on the heteroaromatic ring are arranged in the order N-C-C-N, and has the function of interacting with metals at three or more densities. Because organic compounds having such a structure readily interact with metals, they can be suitably used as intermediate layers.

[0230] In the above general formula (G1-1), A １ A２ and A ３ Examples of substituted or unsubstituted heteroaromatic rings having 1 to 30 carbon atoms, represented by the formula, include heteroaromatic rings having a pyridine skeleton (pyridine ring, quinoline ring, isoquinoline ring, naphthyridine ring, bipyridine ring, phenanthridine ring, phenanthroline ring, antilysine ring, azafluorantene ring), heteroaromatic rings having a diazine skeleton (pyrazine ring, pyrimidine ring, pyridazine ring, quinoxaline ring, benzoquinoxaline ring, dibenzoquinoxaline ring, quinine ring) Examples include zoline rings, benzoxynazoline rings, phthalazine rings, cinnoline rings, pteridine rings, phenazine rings), heteroaromatic rings having a triazine skeleton, heteroaromatic rings having an azole skeleton (imidazole rings, benzimidazole rings, pyrazole rings, oxazole rings, thiazole rings, triazole rings, oxadiazole rings, thiadiazole rings), and so on, with heteroaromatic rings having a pyridine skeleton or heteroaromatic rings having a diazine skeleton being particularly preferred. However, A １ A ２ and A ３ The substituted or unsubstituted heteroaromatic rings with 1 to 30 carbon atoms represented by these are not limited to these. １ A ２ and A ３ They may form fused rings with each other. For example, A １ and A ２ These elements may bond to each other to form a phenanthroline ring.

[0231]

[0232] In the above general formula (G1-2), A1 and A2 each independently represent a substituted or unsubstituted heteroaromatic ring having 1 to 30 carbon atoms, A1 and A2 may form a fused ring with each other, and A1 has 2 or more nitrogen atoms.

[0233] Organic compounds represented by the general formula (G1-2) have conjugated double bonds in which the nitrogen atoms on the heteroaromatic ring are arranged in the order N-C-C-N, and have the function of interacting with metals at two or more dentations. Because organic compounds having such a structure readily interact with metals, they can be suitably used as intermediate layers.

[0234] In the above general formula (G1-2), A １ Examples of substituted or unsubstituted heteroaromatic rings having 1 to 30 carbon atoms represented by A include heteroaromatic rings having a diazine skeleton (pyrazine ring, pyrimidine ring, pyridazine ring, quinoxaline ring, benzoquinoxaline ring, dibenzoquinoxaline ring, quinazoline ring, benzoquinazoline ring, phthalazine ring, sinnoline ring, pteridine ring, phenazine ring), heteroaromatic rings having a triazine skeleton, and heteroaromatic rings having an azole skeleton (imidazole ring, benzimidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadiazole ring, thiadiazole ring). ２ Examples of substituted or unsubstituted heteroaromatic rings having 1 to 30 carbon atoms, represented by the formula, include heteroaromatic rings having a pyridine skeleton (pyridine ring, quinoline ring, isoquinoline ring, naphthyridine ring, bipyridine ring, phenanthridine ring, phenanthroline ring, antilysine ring, azafluorantene ring), heteroaromatic rings having a diazine skeleton (pyrazine ring, pyrimidine ring, pyridazine ring, quinoxaline ring, benzoquinoxaline ring, dibenzoquinoxaline ring, quinine ring) Examples include zoline rings, benzoxynazoline rings, phthalazine rings, cinnoline rings, pteridine rings, phenazine rings), heteroaromatic rings having a triazine skeleton, heteroaromatic rings having an azole skeleton (imidazole rings, benzimidazole rings, pyrazole rings, oxazole rings, thiazole rings, triazole rings, oxadiazole rings, thiadiazole rings), and so on, with heteroaromatic rings having a pyridine skeleton or heteroaromatic rings having a diazine skeleton being particularly preferred. However, A １ and A ２ The substituted or unsubstituted heteroaromatic rings with 1 to 30 carbon atoms represented by these are not limited to these. １ , and A ２ They may form fused rings with each other. For example, A １ and A ２ These molecules may bond to each other to form a pyrazinoquinoxaline ring.

[0235] Furthermore, substituents that can be applied to the above-mentioned general formulas (G1-1) and (G1-2) include C1 to C10 alkyl groups, C3 to C10 cycloalkyl groups, C6 to C30 aryl groups, C6 to C30 arylene groups, and C1 to C30 heteroaryl groups. Some or all of the hydrogens may be deuterium. Moreover, the groups that can be applied to the above general formulas are not limited to the following specific examples.

[0236] The following are specific examples of organic compounds represented by the general formulas (G1-1) and (G1-2) described above.

[0237]

[0238]

[0239]

[0240] In other words, a light-emitting device having an electron injection layer 115 containing an organic compound represented by general formulas (G1) to (G3) disclosed in Embodiment 1 and a metal or metal compound can be manufactured without a significant increase in driving voltage and will have good characteristics, even when processed by a photolithography method that includes an air exposure process.

[0241] Alternatively, a charge generation layer 116 may be provided instead of the electron injection layer 115 (Figure 1B). 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.

[0242] 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.

[0243] 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. Furthermore, it is preferable to use a phthalocyanine-based material or a metal complex having a metal-oxygen bond and an aromatic ligand as the electron-transporting material used in the electron relay layer 118.

[0244] Specifically, the electron-transporting material used in the electron relay layer 118 can be a perylenetetracarboxylic acid derivative such as 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), 3,4,9,10-perylenetetracarboxylic acid diimide (abbreviated as PTCDI), 3,4,9,10-perylenetetracarboxyl-bis-benzimidazole (abbreviated as PTCBI), (C60-Ih)[5,6]fullerene (abbreviated as C60), or (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, and examples of such compounds include phthalocyanine (abbreviated as H ２Phthalocyanine compounds such as Pc can be used. 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. 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.

[0245] The electron injection buffer layer 119 can be made of 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)).

[0246] Furthermore, if the electron injection buffer layer 119 is formed by including an electron-transporting substance and a donor substance, the donor substance can include 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 above.

[0247] Furthermore, it is preferable that the electron injection buffer layer 119 contains an organic compound represented by general formula (G1) to general formula (G3) disclosed in Embodiment 1. By including an organic compound represented by general formula (G1) to general formula (G3) disclosed in Embodiment 1, electron injection performance is improved, and a light-emitting device with a low driving voltage can be made possible.

[0248] Furthermore, the electron injection buffer layer 119 containing the organic compound represented by general formulas (G1) to (G3) disclosed in Embodiment 1 can improve the donor properties of the metal or metal compound by coordinating with the metal or metal compound. As a result, even if the charge generation layer 116 is exposed to an atmospheric environment, the function of the electron injection buffer layer 119 is suppressed, thereby suppressing an increase in the driving voltage and providing a light-emitting device with good characteristics.

[0249] Furthermore, the electron injection buffer layer 119 may also contain a second organic compound. The second organic compound can be made of the same material as the second organic compound in the electron injection layer. By including the second organic compound in the electron injection buffer layer 119, improvements in heat resistance and electron transport can be achieved.

[0250] 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 formulas (G1) to (G3) 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.

[0251] 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), and elements belonging to Group 1 or Group 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 (CaF)) containing these. ２ Examples include 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 the aforementioned material with a small 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 cathodes, regardless of the magnitude of the work function.

[0252] Furthermore, if the second electrode 102 is formed from 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. In addition, the light extraction efficiency can be improved by forming a cap layer on the second electrode 102 from a material with a high refractive index (for example, a material with a paraphotonic refractive index (NO) of 1.90 or higher at a wavelength of 450 nm, a paraphotonic refractive index (NO) of 1.80 or higher at a wavelength of 520 nm, or a paraphotonic refractive index (NO) of 1.75 or higher at a wavelength of 630 nm). It is preferable to use an organic compound for the cap layer because it is easy to form.

[0253] 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 a wet method using a metal paste.

[0254] 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.

[0255] Furthermore, each electrode or layer described above may be formed using different film deposition methods.

[0256] 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 1C. This light-emitting device has multiple light-emitting units between the anode and the cathode. Each light-emitting unit has a configuration substantially similar to the organic compound layer 103 shown in Figure 1A. In other words, the light-emitting device shown in Figure 1C is a light-emitting device having multiple light-emitting units, while the light-emitting device shown in Figure 1A or Figure 1B is a light-emitting device having one light-emitting unit.

[0257] In Figure 1C, 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 light-emitting unit 511 and the second light-emitting unit 512. The first electrode 501 and the second electrode 502 correspond to the first electrode 101 and the second electrode 102 in Figure 1A, respectively, and the same explanation as given in the explanation of Figure 1A 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.

[0258] 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 1C, 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.

[0259] The intermediate layer 513 is preferably formed with the same configuration as the charge generation layer 116 described in Figure 1B. 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.

[0260] In particular, the electron injection buffer layer 119 in the intermediate layer 513 preferably contains an organic compound represented by general formula (G1) to general formula (G3) disclosed in Embodiment 1. By including the organic compound represented by general formula (G1) to general formula (G3) disclosed in Embodiment 1, electron injection performance is improved, and a light-emitting device with a low driving voltage can be made possible.

[0261] Furthermore, the electron injection buffer layer 119 containing the organic compound represented by general formulas (G1) to (G3) disclosed in Embodiment 1 can improve the 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 503 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.

[0262] 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 formulas (G1) to (G3) as disclosed in Embodiment 1 and a metal or metal compound can be manufactured without a large 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.

[0263] 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.

[0264] 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.

[0265] Figure 1C 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 long-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.

[0266] Furthermore, by making the emission colors of each light-emitting unit different, it is possible to obtain a desired hue of emission from the entire light-emitting device. 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 of emission from the first light-emitting unit and blue hues of emission 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, it is possible to provide a light-emitting device with extremely high current efficiency.

[0267] 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.

[0268] This embodiment can be used in any combination with other embodiments.

[0269] (Embodiment 3) In this embodiment, a display device manufactured using the light-emitting devices described in Embodiments 1 and 2 will be described with reference to Figure 2. Figure 2A is a top view showing the display device, and Figure 2B is a cross-sectional view obtained by cutting Figure 2A along lines A-B and C-D. 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.

[0270] 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 here, a printed wiring board (PWB) may be attached to this FPC. In this specification, the display device includes not only the display device itself, but also the state in which the FPC or PWB is attached to it.

[0271] Next, the cross-sectional structure will be explained using Figure 2B. 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.

[0272] The element substrate 610 may be made using a substrate made of glass, quartz, organic resin, metal, alloy, semiconductor, or a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (Polyvinyl Fluoride), polyester, or acrylic resin.

[0273] 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.

[0274] 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 with crystalline regions in part) may be used. Using a crystalline semiconductor is preferable because it can suppress the degradation of transistor characteristics.

[0275] 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.

[0276] 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 system oxide (where M is a metal such as Al, Ti, Ga, Ge, Y, Zr, Sn, La, Ce, or Hf).

[0277] 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.

[0278] By using such materials as semiconductor layers, fluctuations in electrical properties can be suppressed, enabling the realization of highly reliable transistors.

[0279] Further, due to its low off-state current, the transistor including the above-described semiconductor layer can retain charge accumulated in a capacitor via the transistor over a long period of time. By applying such a transistor to pixels, it is possible to stop the driving circuit while maintaining the gray level of the pixels in each display region. As a result, an electronic device with significantly reduced power consumption can be realized.

[0280] For stabilizing the characteristics of a transistor and the like, it is preferable to provide a base film. As the base film, an inorganic insulating film such as a silicon oxide film, a silicon nitride film, a silicon oxynitride film, or a silicon nitride oxide film is used, and the base film can be formed as a single layer or a stacked layer. The base film can be formed by sputtering, CVD (Chemical Vapor Deposition) (such as plasma CVD, thermal CVD, or MOCVD (Metal Organic CVD)), ALD (Atomic Layer Deposition), a coating method, a printing method, or the like. Note that the base film does not need to be provided if it is not necessary.

[0281] Note that FET 623 is one of the transistors formed in the driving circuit portion 601. The driving circuit may be formed of various CMOS circuits, PMOS circuits, or NMOS circuits. Although this embodiment shows a driver-integrated type in which the driving circuit is formed over a substrate, such a structure is not necessarily required, and the driving circuit can be formed outside instead of over the substrate.

[0282] Further, the pixel portion 602 is formed of a plurality of pixels including a switching FET 611, a current controlling FET 612, and a first electrode 613 electrically connected to the drain thereof; however, the structure is not limited thereto, and the pixel portion may be a combination of three or more FETs and a capacitive element.

[0283] Note that an insulator 614 is formed to cover an end portion of the first electrode 613. Here, the insulator 614 can be formed using a positive photosensitive acrylic resin film.

[0284] Furthermore, in order to improve the coverage of an organic compound layer and the like formed later, a curved surface having a curvature is formed at an upper end portion or a lower end portion of the insulator 614. For example, when a positive photosensitive acrylic resin is used as a material of the insulator 614, it is preferable that only the upper end portion of the insulator 614 is provided with a curved surface having a radius of curvature (0.2 μm to 3 μm). Further, as the insulator 614, either a negative photosensitive resin or a positive photosensitive resin can be used.

[0285] An organic compound layer 616 and a second electrode 617 are each formed on the first electrode 613. Here, as a material used for the first electrode 613 functioning as an anode, it is desirable to use a material having a large work function. For example, in addition to single-layer films such as an ITO film, a silicon-containing indium tin oxide film, an indium oxide film containing 2 to 20 wt% of zinc oxide, a titanium nitride film, a chromium film, a tungsten film, a Zn film, and a Pt film, a laminate of a titanium nitride film and a film containing aluminum as a main component, a three-layer structure of a titanium nitride film, a film containing aluminum as a main component, and a titanium nitride film, or the like can be used. Note that with a laminated structure, the resistance as a wiring is low, good ohmic contact can be obtained, and furthermore the structure can function as an anode.

[0286] Further, the organic compound layer 616 is formed by various methods such as a vapor deposition method using a vapor deposition mask, an inkjet method, and a spin coating method. The organic compound layer 616 includes the structures described in Embodiment 1 and Embodiment 2. Further, as other materials constituting the organic compound layer 616, low-molecular-weight compounds or high-molecular-weight compounds (including oligomers and dendrimers) may be used.

[0287] Furthermore, it is preferable to use a material with a small 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. When 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, or zinc oxide (ZnO)) as the second electrode 617.

[0288] The first electrode 613, the organic compound layer 616, and the second electrode 617 form a light-emitting device. This light-emitting device is the light-emitting device described in Embodiment 1 and Embodiment 2. Although the pixel portion is made up of multiple light-emitting devices, the display device in this embodiment may contain a mixture of light-emitting devices described in Embodiment 1 and Embodiment 2 and light-emitting devices having other configurations.

[0289] 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 the effects of moisture, which is a preferred configuration.

[0290] 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.

[0291] Although not shown in Figure 2, a cap layer and / or protective film may be provided on the second electrode. Forming a cap layer can improve the light extraction efficiency. Preferably, the cap layer is formed using a material having, for example, a paraphotonic refractive index (NO) of 1.90 or higher at a wavelength of 450 nm, a paraphotonic refractive index (NO) of 1.80 or higher at a wavelength of 520 nm, or a paraphotonic refractive index (NO) of 1.75 or higher at a wavelength of 630 nm. Furthermore, it is preferable to form the cap layer by depositing an organic compound by vapor deposition, as this method can be easily performed.

[0292] The protective film can be formed from an organic resin film or an inorganic insulating film. It is particularly preferable to use a material that can be formed using the atomic layer deposition (ALD) method for the protective film. Using the ALD method allows for the formation of a dense protective film with reduced defects such as cracks and pinholes, or a film with a uniform thickness. Furthermore, it reduces damage to the processed component during the formation of the protective film.

[0293] Furthermore, a protective film may be formed to cover the exposed portion of the sealing material 605. The protective film can also be provided to cover the surface and sides of the pair of substrates, the sealing layer, the insulating layer, and other exposed surfaces.

[0294] The protective film can be made of a material that is impermeable to impurities such as water. Therefore, it is possible to effectively suppress the diffusion of impurities such as water from the outside to the inside.

[0295] 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.

[0296] 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.

[0297] As described above, a display device manufactured using the light-emitting devices described in Embodiment 1 and Embodiment 2 can be obtained.

[0298] Since the display device in this embodiment uses the light-emitting devices described in Embodiment 1 and Embodiment 2, a display device with good characteristics can be obtained. Specifically, because the light-emitting devices described in Embodiment 1 and Embodiment 2 have high luminous efficiency, it is possible to make a display device with low power consumption. Furthermore, since the light-emitting devices described in Embodiment 1 and Embodiment 2 have good reliability, a highly reliable display device can be made. In addition, the light-emitting devices described in Embodiment 1 and Embodiment 2 can be made into a light-emitting device with good display quality.

[0299] Furthermore, this embodiment can be freely combined with other embodiments.

[0300] (Embodiment 4) Multiple light-emitting devices 130 are formed on the insulating layer 175 as illustrated in Figures 3A and 3B to constitute a display device. In this embodiment, another embodiment of the display device of the present invention will be described in detail.

[0301] 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.

[0302] In this specification, when describing matters common to, for example, 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.

[0303] 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 combinations of other colors of sub-pixels may also 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 yellow (Y), and four sub-pixels of R, G, B, and infrared (IR).

[0304] In this specification and other documents, the row direction may be referred to as the X direction and the column direction as the Y direction. The X and Y directions intersect, for example, perpendicularly.

[0305] Figure 3A 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.

[0306] A connecting portion 140 and a region 141 may be provided on the outside of the pixel portion 177. If a region 141 is provided, it is located between the pixel portion 177 and the connecting portion 140. If a region 141 is provided, an organic compound layer is provided in the region 141. A conductive layer 151C is provided in the connecting portion 140.

[0307] Figure 3 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 multiple.

[0308] Figure 3B is an example of a cross-sectional view between the dashed line A1-A2 in Figure 3A. As shown in Figure 3B, 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.

[0309] 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.

[0310] In Figure 3B, 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.

[0311] In Figure 3B, the light-emitting device 130 is shown as light-emitting device 130R, light-emitting device 130G, and light-emitting device 130B. Light-emitting devices 130R, 130G, and 130B are light-emitting devices that 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.

[0312] 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.

[0313] 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, a common layer 104 on the organic compound layer 103R, and a second electrode (common electrode) 102 on the common layer. Note that the common layer 104 may or may not be provided, but providing the common layer 104 is preferable because it can reduce damage to the organic compound layer 103R during processing.

[0314] The light-emitting device 130G includes a first electrode 101G (pixel electrode) consisting of a conductive layer 151G and a conductive layer 152G, an organic compound layer 103G on the first electrode, a common layer 104 on the organic compound layer 103G, and a second electrode (common electrode) 102 on the common layer. Note that the common layer 104 may or may not be provided, but providing the common layer 104 is preferable because it can reduce damage to the organic compound layer 103G during processing.

[0315] The light-emitting device 130B has a configuration as shown in Embodiment 1 and Embodiment 2. It includes a first electrode 101B (pixel electrode) consisting of a conductive layer 151B and a conductive layer 152B, an organic compound layer 103B on the first electrode, a common layer 104 on the organic compound layer 103B, and a second electrode (common electrode) 102 on the common layer. Note that the common layer 104 may or may not be provided, but providing the common layer 104 is preferable because it can reduce damage to the organic compound layer 103B during processing. In addition, 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 1 and Embodiment 2.

[0316] Note that the common layer 104 is preferably an electron injection layer or an electron transport layer, and more preferably an electron injection layer. In addition, when it is an electron transport layer, the electron transport layer preferably has a laminated structure, and among the laminated layers, it is more preferable that 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.

[0317] Furthermore, since the light-emitting devices 130R and 130G are also light-emitting devices manufactured through a photolithography process, it is possible to create light-emitting devices with low drive voltages, in which the increase in drive voltage due to the photolithography process is suppressed.

[0318] 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, it is assumed that the pixel electrodes function as the anode and the common electrodes function as the cathode.

[0319] 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.

[0320] The island-shaped organic compound layers 103 are formed by depositing an organic compound film and then processing the organic compound film using photolithography.

[0321] Preferably, the organic compound layer 103 is provided so as to cover the upper 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.

[0322] 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 3B, the first electrode of the light-emitting device 130 is in a stacked configuration of a conductive layer 151 and a conductive layer 152.

[0323] 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.

[0324] 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.

[0325] 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.

[0326] 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.

[0327] Next, an example of a method for manufacturing a display device 100 having the configuration shown in Figure 3A will be explained using Figures 4 to 9. Figures 4 to 9 are cross-sectional views taken along A1-A2 and B1-B2 in Figure 3A.

[0328] [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.

[0329] 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.

[0330] Furthermore, when processing the thin films that make up the display device, the processing can be done using methods such as photolithography.

[0331] 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.

[0332] For etching thin films, dry etching, wet etching, or sandblasting methods can be used.

[0333] First, as shown in Figure 2A, 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.

[0334] As the substrate, a substrate having at least enough 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.

[0335] Next, as shown in Figure 4A, 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.

[0336] Next, as shown in Figure 4A, conductive films 151f, 152R, 152G, 152B, and 152C are formed on the plug 176 and the insulating layer 175, respectively. These films will later become conductive layers 151R, 151G, 151B, and 151C. 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.

[0337] Next, as shown in Figure 4A, a resist mask 191 is formed on the conductive film 152f. The resist mask 191 can be formed by applying a photosensitive material (photoresist), exposing it to light, and developing it.

[0338] Next, as shown in Figure 4B, for example, the conductive films 151f and 152f in areas that do not overlap with the resist mask 191 are removed. This forms the conductive layers 151 and 152.

[0339] Next, as shown in Figure 4C, the resist mask 191 is removed. The resist mask 191 can be removed, for example, by ashing using oxygen plasma.

[0340] Next, as shown in Figure 4D, 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.

[0341] For the insulating film 156f, 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, such as silicon oxidative nitride, can be used.

[0342] Next, as shown in Figure 4E, insulating layer 156R, insulating layer 156G, insulating layer 156B, and insulating layer 156C are formed by processing the insulating film 156f.

[0343] Next, as shown in Figure 5A, 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 5A, the organic compound film 103Rf is not formed on the conductive layer 152C.

[0344] Next, as shown in Figure 5A, a sacrificial film 158Rf and a mask film 159Rf are formed.

[0345] 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.

[0346] 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.

[0347] 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 embodiment of the present invention contains the first compound, it is possible to provide a display device with good display quality even after undergoing a heating process at a higher temperature.

[0348] 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.

[0349] 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, the ALD method (Atomic Layer Deposition method) or vacuum deposition method is preferred over the sputtering method.

[0350] The sacrificial film 158Rf and the mask film 159Rf can be, for example, one or more of the following: metal films, alloy films, metal oxide films, semiconductor films, organic insulating films, and inorganic insulating films.

[0351] 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.

[0352] 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.

[0353] 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.

[0354] For the sacrificial film 158Rf and the 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, a compound containing the above semiconductor material can be used.

[0355] 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.

[0356] Next, as shown in Figure 5A, a resist mask 190R is formed. The resist mask 190R can be formed by applying a photosensitive material (photoresist), exposing it to light, and developing it.

[0357] 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.

[0358] Next, as shown in Figure 5B, 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.

[0359] 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.

[0360] 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.

[0361] The resist mask 190R can be removed in the same manner as the resist mask 191.

[0362] Next, as shown in Figure 5B, 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.

[0363] As a result, as shown in Figure 5B, 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.

[0364] The organic compound film 103Rf is preferably processed by anisotropic etching. In particular, anisotropic dry etching is preferred. Alternatively, wet etching may be used.

[0365] 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.

[0366] 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. Moreover, it suppresses problems such as the adhesion of reaction products generated during etching.

[0367] When using the dry etching method, for example, H ２ CF ４ , C ４ F ８ SF ６ CHF ３ , Cl ２ , H ２ O, BCl ３ It is preferable to use a gas containing one or more of the Group 18 elements, such as He or 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.

[0368] Next, as shown in Figure 6A, an organic compound film 103Gf, which will later become the organic compound layer 103G, is formed.

[0369] 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.

[0370] Next, as shown in Figure 6A, 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 the mask film 159Gf 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 190G are the same as those applicable to the resist mask 190R.

[0371] The resist mask 190G is placed in a position that overlaps with the conductive layer 152G.

[0372] Next, as shown in Figure 6B, 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.

[0373] Next, as shown in Figure 6C, an organic compound film 103Bf is formed.

[0374] 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 configuration as the organic compound film 103Rf.

[0375] Next, as shown in Figure 6C, a sacrificial film 158Bf and a mask film 159Bf are formed in sequence. After that, a 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.

[0376] The resist mask 190B is placed in a position that overlaps with the conductive layer 152B.

[0377] Next, as shown in Figure 6D, 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.

[0378] As a result, as shown in Figure 6D, 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.

[0379] 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.

[0380] 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-shaped 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.

[0381] Next, as shown in Figure 7A, it is preferable to remove the mask layer 159R, mask layer 159G, and mask layer 159B.

[0382] 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.

[0383] 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.

[0384] 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.

[0385] Next, as shown in Figure 7B, an inorganic insulating film 125f is formed.

[0386] Next, as shown in Figure 7C, an insulating film 127f, which will later become an insulating layer 127, is formed on the inorganic insulating film 125f.

[0387] The substrate temperature when forming the inorganic insulating film 125f and the 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.

[0388] 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.

[0389] 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 film with high coverage. As the inorganic insulating film 125f, for example, it is preferable to form an aluminum oxide film using the ALD method.

[0390] 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.

[0391] 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.

[0392] 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.

[0393] 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).

[0394] Next, as shown in Figure 8A, development is performed to remove the exposed area of ​​the insulating film 127f and form the insulating layer 127a.

[0395] Next, as shown in Figure 8B, 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.

[0396] 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.

[0397] When performing dry etching, it is preferable to use a chlorine-based gas. Examples of chlorine-based gases include Cl ２ , BCl ３ SiCl ４ , and CCl ４ These can be used individually or in combination of two or more gases. In addition, oxygen gas, hydrogen gas, helium gas, and argon gas, etc., can be added to the chlorine-based gas as appropriate, individually or in combination of two or more gases. By using dry etching, thin areas of the sacrificial layer 158R, sacrificial layer 158G, and sacrificial layer 158B can be formed with good in-plane uniformity.

[0398] 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.

[0399] 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, for wet etching of an aluminum oxide film, an aqueous TMAH solution, which is an alkaline solution, can be used. 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 formed 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.

[0400] 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.

[0401] 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.

[0402] Here, the presence of oxygen barrier insulating layers (for example, an aluminum oxide film) as sacrificial layers 158R, 158G, and 158B reduces the diffusion of oxygen into organic compound layers 103R, 103G, and 103B.

[0403] 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 8C). 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.

[0404] In the first etching process, by not completely removing the sacrificial layers 158R, 158G, and 158B, and leaving them in a thinned state, it is possible to prevent the organic compound layers 103R, 103G, and 103B from being damaged and degraded during the heat treatment. Therefore, the reliability of the light-emitting device can be improved.

[0405] Next, as shown in Figure 9A, 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 layers 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.

[0406] The edges of the inorganic insulating layer 125 are covered with the insulating layer 127. Figure 9A 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.

[0407] 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.

[0408] Next, as shown in Figure 9B, a common electrode 155 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 155 can be formed by methods such as sputtering or vacuum deposition.

[0409] Next, as shown in Figure 9C, a protective layer 131 is formed on the common electrode 155. 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, by using a material with a paraphotonic refractive index (NO) of 1.90 or higher at a wavelength of 450 nm, a paraphotonic refractive index (NO) of 1.80 or higher at a wavelength of 520 nm, or a paraphotonic refractive index (NO) of 1.75 or higher at a wavelength of 630 nm, 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. The cap layer can also serve as a protective layer.

[0410] 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 device 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.

[0411] 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.

[0412] As described above, in the method for manufacturing a display device according to one aspect of the present invention, the island-shaped organic compound layers 103R, 103G, and 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 layers 103R, 103G, and 103B in adjacent subpixels. Therefore, it is possible to suppress the generation of leakage current between subpixels. This prevents crosstalk and makes it possible to 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.

[0413] (Embodiment 5) This embodiment describes a display device according to one aspect of the present invention.

[0414] 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, as well as 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.

[0415] Furthermore, the display device of this embodiment can be a high-resolution display device or a large display device. Therefore, the display device of this embodiment can be used in electronic devices with relatively large screens, such as television systems, 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.

[0416] [Display Module] Figure 10A 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 the display device 100A, but may be any of the display devices 100B to 100E described later.

[0417] The display module 280 has a substrate 291 and a substrate 292. The substrate 291 can be made of glass, quartz, 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. The substrate 292 can be made of one of the above materials that is translucent. The display module 280 has a display section 281. The display section 281 is the area in the display module 280 that displays the image, and is the area in which light from each pixel provided in the pixel section 284, which will be described later, can be seen.

[0418] Figure 10B 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 composed of multiple wires.

[0419] The pixel section 284 has a plurality of pixels 284a arranged periodically. An enlarged view of one pixel 284a is shown on the right side of Figure 10B. Various configurations described in the previous embodiment can be applied to the pixels 284a.

[0420] The pixel circuit section 283 has a plurality of pixel circuits 283a arranged periodically.

[0421] One pixel circuit 283a is a circuit that controls the driving of multiple elements that a single pixel 284a has.

[0422] 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.

[0423] The FPC 290 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 FPC 290.

[0424] 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, thereby making it possible to achieve an extremely high aperture ratio (effective display area ratio) for the display section 281.

[0425] Because such a display module 280 is extremely high-resolution, it can be suitably used in VR devices such as HMDs or AR devices in the form of 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, enabling a highly immersive display. Furthermore, the display module 280 is not limited to this and can be suitably used in electronic devices having relatively small display parts.

[0426] [Display device 100A] The display device 100A shown in Figure 11A includes a substrate 301, a light-emitting device 130R, a light-emitting device 130G, a light-emitting device 130B, a capacitor 240, and a transistor 310.

[0427] The substrate 301 corresponds to the substrate 291 in Figures 11A and 11B. The transistor 310 is a transistor having a channel formation region in the substrate 301. As the substrate 301, a semiconductor substrate such as a single-crystal silicon substrate can be used. The transistor 310 has a part of the 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 the substrate 301 and the conductive layer 311 and functions as a gate insulating layer. The low-resistance region 312 is a region of the 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.

[0428] Furthermore, an element isolation layer 315 is provided between two adjacent transistors 310 so as to be embedded in the substrate 301.

[0429] Furthermore, an insulating layer 261 is provided to cover the transistor 310, and a capacitance 240 is provided on the insulating layer 261.

[0430] The capacitor 240 has a conductive layer 241, a conductive layer 245, and an insulating layer 243 located between them. The conductive layer 241 functions as one electrode of the capacitor 240, the conductive layer 245 functions as the other electrode of the capacitor 240, and the insulating layer 243 functions as the dielectric of the capacitor 240.

[0431] 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.

[0432] 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.

[0433] 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.

[0434] 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.

[0435] 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 devices 130 to the substrate 120 can be found in Embodiment 4. The substrate 120 corresponds to the substrate 292 in Figure 10A.

[0436] Figure 11B is a modified example of the display device 100A shown in Figure 11A. The display device shown in Figure 11B 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 11B, 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.

[0437] [Display device 100B] Figure 12 shows a perspective view of the display device 100B, and Figure 12 shows a cross-sectional view of the display device 100C.

[0438] 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.

[0439] 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 an IC 354 and an FPC 353 are mounted on the display device 100B. Therefore, the configuration shown in Figure 12 can also be called a display module having a 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 to the substrate, or on which an IC is mounted.

[0440] The connection portion 140 is provided on the outside of the pixel portion 177. There may be one or more connection portions 140. 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.

[0441] For example, a scan line drive circuit can be used as circuit 356.

[0442] 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.

[0443] Figure 12 shows an example in which IC 354 is provided on the substrate 351 using the COG (Chip On Glass) method or the COF (Chip On Film) method. 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 the FPC, for example, using the COF method.

[0444] Figure 13 shows an example of a cross-section of the display device 100C, obtained by cutting a portion of the region 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 region including the end portion of the display device 100B in Figure 12.

[0445] [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 the substrate 351 and the substrate 352.

[0446] Details of the light-emitting devices 130R, 130G, and 130B can be found in Embodiment 4.

[0447] 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.

[0448] 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 end of the conductive layer 151R is located outside the end 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.

[0449] 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.

[0450] 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.

[0451] 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.

[0452] 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.

[0453] 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 sealing structure or a hollow sealing structure can be applied to seal 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 sealing structure. Alternatively, the space may be filled with an inert gas (such as nitrogen or argon), indicating a hollow sealing 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.

[0454] 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.

[0455] 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 counter electrodes (common electrodes 155) contain a material that transmits visible light.

[0456] 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.

[0457] It is preferable to use an inorganic insulating film as the insulating layer 211, insulating layer 213, and insulating layer 215.

[0458] An organic insulating layer is preferred for the insulating layer 214, which functions as a planarizing layer.

[0459] 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.

[0460] 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. The conductive layer 166 is exposed on the upper surface of the connection portion 204. This allows the connection portion 204 and FPC 353 to be electrically connected via the connection layer 242.

[0461] 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. Various optical components can also be arranged on the outside of the substrate 352.

[0462] Materials suitable for use on substrate 120 can be applied to substrate 351 and substrate 352, respectively.

[0463] As the adhesive layer 142, a material that can be used for the resin layer 122 can be applied.

[0464] As the connecting layer 242, an anisotropic conductive film (ACF) or an anisotropic conductive paste (ACP) can be used.

[0465] [Display device 100D] The display device 100D shown in Figure 14 differs from the display device 100C shown in Figure 14 mainly in that it is a bottom-emission type display device.

[0466] The light emitted by the light-emitting device is emitted towards the substrate 351. It is preferable to use a material with high transmittance 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.

[0467] 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.

[0468] 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.

[0469] 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.

[0470] 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.

[0471] Although the light-emitting device 130G is not shown in Figure 14, it is also provided.

[0472] 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.

[0473] [Display Device 100D2] Display device 100D2 shown in Figure 15 is an example of a bottom-emission type display device that differs from display device 100D shown in Figure 15. Display device 100D2 differs from 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 15 may be omitted, and details should be referred to in the description in Figure 15.

[0474] Furthermore, Figure 15B shows the top view layout of a pixel 178 (pixels 178a and 178b) having sub-pixels 110 (sub-pixels 110R, 110G, 110B, and 110W), and Figure 15C 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 space between the light-shielding layers 317 is the width 110Rw of the light-emitting region of sub-pixel 110R.

[0475] As shown in Figure 15A, the organic resin layer 180 is provided on the insulating layer 214. As shown in the region enclosed by the dashed line in Figure 15A and in Figure 15C, the organic resin layer 180 has curved recesses 181 (recesses 181a and 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.

[0476] Multiple recesses 181 may be formed on the matrix. Recesses 181a and 181b may be in contact with each other, or there may be a plane between them.

[0477] Furthermore, in Figure 15, the upper surface shape of the recess is shown as a hexagon (Figure 15C) and the cross-sectional shape as a semicircle (Figure 15A), but other shapes may be used as needed. For example, the upper 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.

[0478] 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.

[0479] 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.

[0480] 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.

[0481] 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.

[0482] 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.

[0483] 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.

[0484] Although the light-emitting devices 130G and 130B are not shown in Figure 15, they are also provided.

[0485] [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.

[0486] 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.

[0487] In the display device 100E, 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. The display device 100E may also be configured to have the colored layers 132R, 132G, and 132B placed between the protective layer 131 and the adhesive layer 142.

[0488] [Display device 100E2] The display device 100E2 shown in Figure 17 is a modified version of the display device 100E shown in Figure 16, and has a microlens 182 on the colored layer 132R, the colored layer 132G, and the 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.

[0489] Figure 17B shows the top view layout of a pixel 178 (pixels 178a and 178b) having sub-pixels 110 (sub-pixels 110R, 110G, and 110B), and Figure 17C shows the top view of the microlens 182 in the region where the sub-pixels 110R and 110G of pixel 178 are formed. The region where the common electrode 155 and the organic compound layer 103 are in contact is the width 110Gw of the light-emitting region of sub-pixel 110G.

[0490] The display device 100E2 shown in Figure 17A has a planarization film 143 on a protective layer 131, and a colored layer 132R, a colored layer 132G, and a colored layer 132B on the planarization film 144. The planarization film 144 is provided so as to cover the colored layers 132R, 132G, and 132B. A microlens 182 is provided on the planarization film 144.

[0491] Furthermore, as shown in Figure 17C, the microlenses 182 may be provided for each sub-pixel in the region where the sub-pixels are formed.

[0492] In Figure 17C, 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 polygons, a polygon with rounded corners, an ellipse, or a circle.

[0493] The microlens 182 can be formed using the same material as the organic resin layer 180.

[0494] 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.

[0495] (Embodiment 6) This embodiment describes an electronic device according to one aspect of the present invention.

[0496] 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.

[0497] 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.

[0498] An example of a wearable device that can be worn on the head will be explained using Figures 18A to 18D.

[0499] The electronic device 700A shown in Figure 18A and the electronic device 700B shown in Figure 18B 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.

[0500] 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.

[0501] Electronic devices 700A and 700B can each 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.

[0502] 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.

[0503] 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.

[0504] Furthermore, electronic devices 700A and 700B are equipped with batteries that can be charged wirelessly, wired, or both.

[0505] The housing 721 may also be provided with a touch sensor module.

[0506] 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.

[0507] The electronic device 800A shown in Figure 18C and the electronic device 800B shown in Figure 18D 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.

[0508] 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.

[0509] The display unit 820 is located inside the housing 821 in a position visible through the lens 832. Furthermore, by displaying different images on a pair of display units 820, a three-dimensional display using parallax can be achieved.

[0510] 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.

[0511] The attachment portion 823 allows the user to attach the electronic device 800A or the electronic device 800B to their head.

[0512] 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.

[0513] The electronic device 800A may have a vibration mechanism that functions as a bone conduction earphone.

[0514] 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 in the electronic devices.

[0515] An electronic device according to one aspect of the present invention may have a function for wireless communication with an earphone 750.

[0516] Furthermore, the electronic device may have an earphone section. The electronic device 700B shown in Figure 18B 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.

[0517] Similarly, the electronic device 800B shown in Figure 18D 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.

[0518] 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.

[0519] The electronic device 6500 shown in Figure 19A is a portable information terminal that can be used as a smartphone.

[0520] 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.

[0521] 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.

[0522] Figure 19B is a schematic cross-sectional view of the housing 6501 including the end on the microphone 6506 side.

[0523] 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.

[0524] 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).

[0525] 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.

[0526] 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.

[0527] Figure 19C 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.

[0528] 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.

[0529] The television device 7100 shown in Figure 19C can be operated using the operation switches on the housing 7171 and a separate remote control unit 7151.

[0530] Figure 19D 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.

[0531] 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.

[0532] Figures 19E and 19F show examples of digital signage that can be used in shop windows and display cases.

[0533] The digital signage 7300 shown in Figure 19E includes 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.

[0534] Figure 19F 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.

[0535] In Figures 19E and 19F, 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.

[0536] 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.

[0537] 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 19E and 19F, 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.

[0538] 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.

[0539] Furthermore, as shown in Figures 19E and 19F, it is preferable that the digital signage 7300 or digital signage 7400 can be linked wirelessly with an information terminal device 7311 or information terminal device 7411 such as a smartphone owned by the user.

[0540] The electronic equipment shown in Figures 20A to 20G 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, and the like.

[0541] The electronic devices shown in Figures 20A to 20G have various functions. For example, they may have functions to display various information (still images, videos, text images, etc.) on a display unit, a touch panel function, a function to display a calendar, date or time, a function to control processing by various software (programs), a wireless communication function, a function to read and process programs or data recorded on a recording medium, and so on.

[0542] Details of the electronic equipment shown in Figures 20A to 20G will be explained below.

[0543] Figure 20A 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 20A 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 title 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 same location where information 9051 is displayed.

[0544] Figure 20B 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.

[0545] Figure 20C 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. The left side of the housing 9000 has operation keys 9005 as buttons for operation, and the bottom has connection terminals 9006.

[0546] Figure 20D 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.

[0547] Figures 20E to 20G are perspective views showing a foldable portable information terminal 9201. Figure 20E shows the portable information terminal 9201 in an unfolded state, Figure 20G shows it in a folded state, and Figure 20F shows a perspective view of the state in between, transitioning from one of Figures 20E or 20G 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.

[0548] 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.

[0549] (Synthesis Example 1) In this example, we will describe the synthesis method of 4,7-di(4-azatricyclo[5.2.2.0,2,6]undecane-4-yl)-1,10-phenanthroline (abbreviated as Acu2Phen), which is shown by structural formula (100) in Embodiment 1. The structure of Acu2Phen is shown below.

[0550]

[0551] <Synthesis of Acu2Phen> In a 100 mL three-necked flask, 1.59 g (6.38 mmol) of 4,7-dichloro-1,10-phenanthroline, 3.00 g (16.0 mmol) of 4-azatricyclo[5.2.2.0,2,6]undecane hydrochloride, and 4.87 g (32.0 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) were added and stirred at 100°C for 7 hours under a nitrogen stream. After stirring, the mixture was allowed to cool to room temperature. Water was added to the mixture, and extraction was performed with chloroform. The extract was concentrated to obtain a solid. This solid was recrystallized with chloroform and acetone, and the precipitated solid was collected by suction filtration to obtain a light brown solid (1.89 g, yield 61.8%). The synthesis scheme for Acu2Phen is shown in equation (a-1) below.

[0552]

[0553] The obtained light brown solid (1.89 g) was purified by sublimation using the train sublimation method. Sublimation purification was performed at a pressure of 2.8 × 10⁻⁶. −２ The experiment was conducted by heating at Pa and a heating temperature of 230°C for 46 hours. As a result, the target substance was obtained as a pale yellow solid (0.560 g, recovery rate 29.6%).

[0554] Acu2Phen after sublimation purification １ The HNMR spectra are shown in Figures 21A to 21C. Figure 21B is a magnified view of the 1 ppm to 4 ppm range of Figure 21A, and Figure 21C is a magnified view of the 6.5 ppm to 9 ppm range. １ The results of the 1HNMR measurement are shown below. From these results, it was confirmed that Acu2Phen was obtained by this synthesis method.

[0555] １HNMR (CDCl ３ , 500MHz): δ = δ8.86 (d, J = 5.3Hz, 2H), 8.05 (s, 2H), 6.94 (d, J = 5.3Hz, 2H), 3.57-3.51 ( m, 8H), 2.55-2.49 (m, 4H), 1.94-1.89 (m, 4H), 1.72-1.57 (m, 12H), 1.51-1.40 (m, 4H).

[0556] The glass transition temperature (Tg) of Acu2Phen was measured. Tg was measured using a differential scanning calorimetry system (DSC8500, PerkinElmer Japan Co., Ltd.). Acu2Phen powder was placed in an aluminum cell, heated until it melted, cooled to -10°C, and then heated again at a rate of 40°C / min. The result showed that the Tg of Acu2Phen was 110°C.

[0557] Next, a solubility test was conducted for Acu2Phen. This test was performed at 1 atmosphere and room temperature (RT).

[0558] <Solubility test of Acu2Phen by LC / MS analysis> LC / MS analysis was performed using a Waters Acquity UPLC for LC (liquid chromatography) separation and a Waters Xevo G2 Tof MS for MS (mass spectrometry). For LC separation, an Acquity UPLC BEH C8 column (2.1 × 100 mm, 1.7 μm) was used. Mobile phase A was acetonitrile and mobile phase B was a 0.1% formic acid aqueous solution. The sample injection volume was 5.0 μL. The analysis was performed using a photodiode array detector at a wavelength of 265 nm ± 1 nm.

[0559] 1 mg of Acu2Phen was placed in a 5 mL sample vial, 2 mL of chloroform was added, and sonication was performed for 10 minutes. After confirming that the solid was completely dissolved, this solution was diluted 10-fold with acetonitrile to prepare a 50 mg / L solution. Based on this solution, solutions with concentrations of 5 mg / L, 0.5 mg / L, 0.05 mg / L, 0.005 mg / L, and 0.0005 mg / L were prepared by dilution with acetonitrile. LC / MS analysis was performed using the prepared solutions. Absorption peaks derived from Acu2Phen were obtained at concentrations of 0.05 mg / L and above, but no absorption peaks derived from Acu2Phen were obtained at concentrations of 0.005 mg / L and 0.0005 mg / L.

[0560] Next, the solubility of Acu2Phen in water was measured.

[0561] Acu2Phen 1 mg was placed in a 5 mL sample vial, 1 mL of water was added, and the mixture was subjected to sonication for 5 minutes. The mixture was filtered using a membrane filter to remove solids, and the resulting filtrate was analyzed by LC / MS.

[0562] As a result, no absorption peak originating from Acu2Phen was obtained from LC / MS analysis. From the results obtained from LC / MS analysis, it was found that the solubility of Acu2Phen in water is 0.05 mg / L or less. It was found that Acu2Phen is an organic compound with very low solubility in water.

[0563] Similarly, when the Tg of Hid2Phen was measured, it was found to be 102°C. Thus, it was found that Acu2Phen is an organic compound with higher heat resistance than Hid2Phen. This is because Acu2Phen has a group containing a polycyclic alkylamine skeleton with a cross-linking structure, which suppresses the vibration and rotation of the cyclic alkylamine skeleton compared to Hid2Phen, which has a group containing a cyclic alkylamine skeleton without a cross-linking structure, thereby improving its heat resistance.

[0564] Furthermore, when the solubility of Hid2Phen in water was measured in the same way as that of Acu2Phen, it was found that the Tg was 102°C and 5.5 mg of Hid2Phen dissolves in 1 mL of water. The solubility of Hid2Phen in water is 5.5 × 10⁻⁶ by weight fraction. −３ This can be converted to the following. Thus, it was found that Acu2Phen is an organic compound with significantly lower solubility in water than Hid2Phen.

[0565] Thus, it was found that Acu2Phen is an organic compound having a phenanthroline ring and a polycyclic alkylamine skeleton with a cross-linking structure, resulting in high heat resistance and low solubility in water. This makes it highly suitable as a material for constructing light-emitting devices that are processed by a heating process and a photolithography process involving exposure to air, water, and aqueous solutions.

[0566] In this example, the method for manufacturing and the characteristics of a light-emitting device 1, which is a light-emitting device according to one aspect of the present invention, will be described in detail. The structural formulas of the main compounds used in light-emitting device 1-1 are shown below.

[0567]

[0568] (Method for fabricating the light-emitting device 1) First, a silver-palladium-copper alloy (APC: Ag-Pd-Cu) is deposited on a glass substrate from the substrate side to a thickness of 100 nm as a reflective electrode by sputtering, and indium tin oxide (ITSO) containing silicon oxide is laminated to a thickness of 50 nm by sputtering as a transparent electrode, forming a first electrode 101 with a size of 2 mm x 2 mm. The transparent electrode functions as an anode and is considered together with the reflective electrode to be the first electrode 101.

[0569] 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.

[0570] After that, approximately 1 x 10 −４The 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.

[0571] Next, the substrate was fixed to a holder provided in a vacuum deposition apparatus so that the surface on which the first electrode 101 was formed was facing downwards. A hole injection layer 111 was then 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 onto the inorganic insulating film and the first electrode 101 by a vapor deposition method.

[0572] A first hole transport layer was formed by depositing PCBiF onto the hole injection layer 111 to a thickness of 130 nm.

[0573] 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-d ３ -methyl-8-(2-pyridinyl-κN)benzoflox[2,3-b]pyridine-κC]bis[2-(5-d ３ [Methyl-2-pyridinyl-κN2)phenyl-κC]iridium(III) (abbreviation: Ir(5mppy-d) ３ ) ２ (mbfpypy-d ３ )) and in weight ratio 0.5:0.5:0.1 (= 8mpTP-4mDBtPBfpm:βNCCP:Ir(5mppy-d ３ ) ２ (mbfpypy-d ３ A first light-emitting layer was formed by co-depositing to a film thickness of 40 nm.

[0574] Subsequently, 2-{3-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-9-yl]phenyl}dibenzo[f,h]quinoxaline (abbreviated as 2mPCCzPDBq), represented by the above structural formula (v), was deposited to a thickness of 10 nm to form the first electron transport layer.

[0575] After the formation of the first electron transport layer, 2,2'-([2,2'-bipyridine]-6,6'-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviated as 6,6'(P-Bqn)2BPy) represented by the above structural formula (vi), 4,7-di(4-azatricyclo[5.2.2.0,2,6]undecane-4-yl)-1,10-phenanthroline (abbreviated as Acu2Phen) represented by the above structural formula (vii), and lithium oxide (Li ２ O) and in volume ratio 0.5:0.5:0.02 (=6,6'(P-Bqn)2BPy:Acu2Phen:Li ２ O) A first layer was formed by co-depositing to a thickness of 5 nm, a third layer was formed by depositing copper phthalocyanine (abbreviated as CuPc) represented by the above structural formula (viii) to a thickness of 2 nm, and a second layer was formed by co-depositing PCBiF and OCHD-003 in a weight ratio of 1:0.15 (= PCBiF:OCHD-003) to a thickness of 10 nm, thereby forming an intermediate layer.

[0576] A second hole transport layer was formed by depositing PCBBiF onto the intermediate layer to a thickness of 50 nm.

[0577] On the second hole transport layer, 8mpTP-4mDBtPBfpm, βNCCP, and Ir(5mppy-d ３ ) ２ (mbfpypy-d ３ ) and are in a weight ratio of 0.5:0.5:0.1 (= 8mpTP-4mDBtPBfpm:βNCCP:Ir(5mppy-d ３ ) ２ (mbfpypy-d ３ A second light-emitting layer was formed by co-depositing to a thickness of 40 nm.

[0578] 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.

[0579] Subsequently, lithium fluoride (LiF) and ytterbium (Yb) were co-deposited in a volume ratio of 1:0.5 (= LiF:0.5) with a film thickness of 1.5 nm to form an electron injection layer. Then, silver (Ag) and magnesium (Mg) were co-deposited in a volume ratio of 1:0.1 with a film thickness of 15 nm to form a 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.

[0580] 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 the light-emitting device 1.

[0581] The device structure of light-emitting device 1 is shown below.

[0582]

[0583] Figure 22 shows the luminance-current density characteristics of the light-emitting device 1, 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 spectrum. Furthermore, the luminance of the light-emitting device 1 is 1000 cd / m². ２ Table 2 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.

[0584]

[0585] Furthermore, the light-emitting device 1 has a current density of 50 mA / cm². ２ Figure 27 shows the normalized brightness time-varying characteristics with an initial brightness of 100% when driven by a constant current.

[0586] Figures 22 to 26 and Table 2 show that the light-emitting device 1 using Acu2Phen as the intermediate layer in a tandem type light-emitting device exhibits high current efficiency and functions as a tandem type light-emitting device. Furthermore, Figure 27 shows that the light-emitting device 1 using Acu2Phen as the intermediate layer in a tandem type light-emitting device is a highly reliable light-emitting device.

[0587] From the above results, it was found that the light-emitting device in which the organic compound represented by general formula (G1) to general formula (G3) is used in the first layer of the tandem type light-emitting device in Embodiment 1 is a light-emitting device with good characteristics.

[0588] In this embodiment, the method for manufacturing and the characteristics of a light-emitting device 2, which is a light-emitting device according to one aspect of the present invention, will be described in detail. The structural formulas of the main compounds used in the light-emitting device 2 are shown below.

[0589]

[0590] (Method for fabricating the light-emitting device 2) First, a silver-palladium-copper alloy (APC: Ag-Pd-Cu) is deposited on a glass substrate from the substrate side as a reflective electrode to a thickness of 100 nm by sputtering, and indium tin oxide (ITSO) containing silicon oxide is laminated as a transparent electrode to a thickness of 50 nm by sputtering, forming a first electrode 101 with a size of 2 mm x 2 mm. The transparent electrode functions as an anode and is considered together with the reflective electrode as the first electrode 101.

[0591] 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.

[0592] After that, approximately 1 x 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.

[0593] Next, the substrate was fixed to a holder provided in a vacuum deposition apparatus so that the surface on which the first electrode 101 was formed was facing downwards. A hole injection layer 111 was then 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 onto the inorganic insulating film and the first electrode 101 by a vapor deposition method.

[0594] A first hole transport layer was formed by depositing PCBiF onto the hole injection layer 111 to a thickness of 130 nm.

[0595] 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-d ３ -methyl-8-(2-pyridinyl-κN)benzoflox[2,3-b]pyridine-κC]bis[2-(5-d ３ [Methyl-2-pyridinyl-κN2)phenyl-κC]iridium(III) (abbreviation: Ir(5mppy-d) ３ ) ２ (mbfpypy-d ３ )) and in weight ratio 0.5:0.5:0.1 (= 8mpTP-4mDBtPBfpm:βNCCP:Ir(5mppy-d ３ ) ２ (mbfpypy-d ３ A first light-emitting layer was formed by co-depositing to a film thickness of 40 nm.

[0596] Subsequently, 2-{3-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-9-yl]phenyl}dibenzo[f,h]quinoxaline (abbreviated as 2mPCCzPDBq), represented by the above structural formula (v), was deposited to a thickness of 10 nm to form the first electron transport layer.

[0597] After the formation of the first electron transport layer, 2,2'-([2,2'-bipyridine]-6,6'-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviated as 6,6'(P-Bqn)2BPy) represented by the above structural formula (vi), 4,7-di(4-azatricyclo[5.2.2.0,2,6]undecane-4-yl)-1,10-phenanthroline (abbreviated as Acu2Phen) represented by the above structural formula (vii), and lithium oxide (Li ２ O) and in volume ratio 0.5:0.5:0.02 (=6,6'(P-Bqn)2BPy:Acu2Phen:Li ２ O) A first layer was formed by co-depositing to a thickness of 5 nm, a third layer was formed by depositing copper phthalocyanine (abbreviated as CuPc) represented by the above structural formula (viii) to a thickness of 2 nm, and a second layer was formed by co-depositing PCBiF and OCHD-003 in a weight ratio of 1:0.15 (= PCBiF:OCHD-003) to a thickness of 10 nm, thereby forming an intermediate layer.

[0598] A second hole transport layer was formed by depositing PCBBiF onto the intermediate layer to a thickness of 50 nm.

[0599] On the second hole transport layer, 8mpTP-4mDBtPBfpm, βNCCP, and Ir(5mppy-d ３ ) ２ (mbfpypy-d ３ ) and are in a weight ratio of 0.5:0.5:0.1 (= 8mpTP-4mDBtPBfpm:βNCCP:Ir(5mppy-d ３ ) ２ (mbfpypy-d ３ A second light-emitting layer was formed by co-depositing to a thickness of 40 nm.

[0600] 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.

[0601] Next, the sample was processed using photolithography. After removing the sample with the second electron transport layer formed from the vacuum deposition apparatus, an aluminum oxide film with a thickness of 30 nm was deposited at 80°C using the ALD (Atomic Layer Deposition) method, with trimethylaluminum (TMA) as the precursor and water vapor as the oxidizing agent, to form the first sacrificial layer. At this time, the surface of the second electron transport layer was exposed to the atmosphere. Next, a molybdenum (Mo) film with a thickness of 50 nm was deposited using the sputtering method to form the second sacrificial layer.

[0602] Subsequently, a photoresist was formed on the second sacrificial layer, and a 3 μm wide slit was formed using lithography at a position 3.5 μm away from the end of the first electrode. Specifically, the resist was used as a mask, and sulfur hexafluoride (SF6) was used. ６ ), oxygen (O ２ The second sacrificial layer was processed using an etching gas containing ), followed by an etching gas containing oxygen, and then the resist was removed using a solution containing tetramethylammonium hydroxide (TMAH). Next, the second sacrificial layer was used as a hard mask with fluoroform (CHF ３ ) and helium (He), CHF ３ The first sacrificial layer was processed using an etching gas containing He at a flow rate ratio of 1:49. After this, oxygen (O) ２ The second electron transport layer, second light-emitting layer, second hole transport layer, intermediate layer, first electron transport layer, first light-emitting layer, first hole transport layer, and hole injection layer were processed using an etching gas containing ).

[0603] After processing, the second sacrificial layer is SF ６ , O ２The first sacrificial layer was removed using an etching gas containing , and then the second electron transport layer was exposed by removing the first sacrificial layer using an aqueous solution containing hydrofluoric acid and phosphoric acid.

[0604] A sample with the second electron transport layer exposed was measured at approximately 1 × 10⁻⁶. −４ Vacuum firing was performed at 100°C for 1 hour in a heating chamber within a vacuum deposition apparatus where the internal pressure was reduced to Pa.

[0605] As described above, processing and heat treatment were performed using photolithography, as well as treatment with water and water-based chemical solutions.

[0606] Subsequently, lithium fluoride (LiF) and ytterbium (Yb) were co-deposited in a volume ratio of 1:0.5 (= LiF:0.5) and with a film thickness of 1.5 nm to form an electron injection layer. Then, silver (Ag) and magnesium (Mg) were co-deposited in a volume ratio of 1:0.1 and with a film thickness of 15 nm to form a second electrode 102. Furthermore, 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviated as 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.

[0607] 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 the light-emitting device 2.

[0608] The device structure of light-emitting device 2 is shown below.

[0609]

[0610] Figure 28 shows the luminance-current density characteristics of light-emitting device 2, Figure 29 shows the current efficiency-luminance characteristics, Figure 30 shows the luminance-voltage characteristics, Figure 31 shows the current density-voltage characteristics, and Figure 32 shows the field emission spectrum. Furthermore, the luminance of light-emitting device 1 is 1000 cd / m². ２Table 4 shows the main characteristics of the vicinity. Luminance, CIE chromaticity, and field emission spectrum were measured using a spectroradiometer (Topcon SR-UL1R) at room temperature.

[0611]

[0612] Furthermore, the light-emitting device 1 has a current density of 50 mA / cm². ２ Figure 33 shows the normalized brightness time-varying characteristics with an initial brightness of 100% when driven by a constant current.

[0613] Figures 28 to 33 and Table 4 show that the light-emitting device 2 using Acu2Phen as the intermediate layer in a tandem-type light-emitting device exhibits high current efficiency and functions as a tandem-type light-emitting device. Furthermore, it was found that even when processing by photolithography is performed during the fabrication process of the light-emitting device, the light-emitting device according to one embodiment of the present invention exhibits a small increase in driving voltage and is a light-emitting device with good characteristics.

[0614] From the above results, it was found that the light-emitting device using the organic compounds shown as general formulas (G1) to (G3) in Embodiment 1 as the first layer in a tandem-type light-emitting device is a light-emitting device with good properties. Furthermore, it was found that the light-emitting device according to one aspect of the present invention exhibits little degradation in properties even when processed by photolithography during the manufacturing process, and is a light-emitting device with good properties.

[0615] (Reference Example 1) This reference example shows the results of a solubility test of Hid2Phen. The molecular structure of Hid2Phen is shown below.

[0616]

[0617] A solubility test was conducted on Hid2Phen.

[0618] <Solubility test of Hid2Phen by LC / MS analysis> LC / MS analysis was performed using a Waters Acquity UPLC for LC (liquid chromatography) separation and a Waters Xevo G2 Tof MS for MS (mass spectrometry). For LC separation, an Acquity UPLC BEH C8 column (2.1 × 100 mm, 1.7 μm) was used. Mobile phase A was acetonitrile and mobile phase B was a 0.1% formic acid aqueous solution. The sample injection volume was 5.0 μL. This test was performed at 1 atm and room temperature (RT), and the photodiode array detector wavelength was 263 nm ± 1 nm.

[0619] 0.4 mg of Hid2Phen was placed in a 5 mL sample vial, 2 mL of chloroform was added, and sonication was performed for 5 minutes. After confirming that the solid was completely dissolved, this solution was diluted 10-fold with acetonitrile to prepare a 20 mg / L solution. Based on this solution, solutions with concentrations of 10 mg / L, 5 mg / L, and 1 mg / L were prepared by dilution with acetonitrile. LC / MS analysis was performed using the prepared solutions, and a calibration curve was created using the absorption peak area values ​​derived from Hid2Phen obtained for each concentration.

[0620] Next, we measured the solubility of Hid2Phen in water.

[0621] 1 mg of Hid2Phen was placed in a 5 mL sample vial, 1 mL of water was added, and the mixture was subjected to sonication for 5 minutes. The mixture was filtered using a membrane filter to remove the solid, and the resulting filtrate was analyzed by LC / MS.

[0622] From the calibration curve and the absorption peak area values ​​derived from Hid2Phen obtained by LC / MS analysis, it was found that 5.5 mg of Hid2Phen dissolves in 1 mL of water. The solubility of Hid2Phen in water is 5.5 × 10⁻⁶ by weight fraction. −３ It can be converted to this.

[0623] 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: Sub-pixel, 110G: Sub-pixel, 110R: Sub-pixel, 110W: Sub-pixel, 110: Sub-pixel, 111: Hole injection layer, 112B: Conductive layer, 112R: Conductive Electron layer, 112: Hole transport layer, 113: Light-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: Substrate, 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: Layer, 129B: Conductive layer, 129R: Conductive layer, 130B: Light-emitting device, 130G: Light-emitting device, 130R: Light-emitting device, 130: Light-emitting device, 131: Protective layer, 132B: Colored layer, 132G: Colored layer, 132R: Colored layer, 140: Connection part, 141: Region, 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-shielding layer, 158B: Sacrificial layer, 158Bf: Sacrificial film , 158G: Sacrificial layer, 158Gf: Sacrificial film, 158R: Sacrificial layer, 158Rf: Sacrificial film, 159B: Mask layer, 159Bf: Mask film, 159G: Mask layer, 159Gf: Mask film, 159R: Mask layer, 159Rf: Mask film, 166: Conductive layer, 171: Insulating layer, 172: Conductive layer, 173: Insulating layer, 174: Insulating layer, 175: Insulating layer, 176: Plug, 177: Pixel part, 178: Pixel, 178a: Pixel, 178b: Pixel, 179: Conductive layer, 190B: Resist mask, 190G: Resist mask, 190R: Resist mask, 191: Resist mask,201: Transistor, 204: Connector, 205: Transistor, 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: Capacitor, 241: Conductive layer, 242: Connector layer, 243: Insulating layer, 245: Conductive layer, 254: Insulating layer, 255: Insulating layer, 256: Plug, 261: Insulating layer, 271: Plug, 280: Display module, 281: Display unit, 282: Circuit unit, 283a: Pixel circuit , 283: Pixel circuit section, 284a: Pixel, 284: Pixel section, 285: Terminal section, 286: Wiring section, 290: FPC, 291: Substrate, 292: Substrate, 301: Substrate, 310: Transistor, 311: Conductive layer, 312: Low-resistance region, 313: Insulating layer, 314: Insulating layer, 315: Element isolation layer, 317: Light-shielding layer, 351: Substrate, 352: Substrate, 353: FPC, 354: IC, 355: Wiring, 356: Circuit, 501: First electrode, 502: Second electrode, 503: Organic compound layer, 511: First light-emitting unit, 512: Second light-emitting unit, 513: Intermediate layer, 601: Source line driving circuit, 601: Drive circuit section, 602: Pixel section, 603: Gate line drive circuit, 604: Encapsulation substrate, 605: Sealing material, 607: Space, 608: Wiring, 610: Element substrate, 611: Switching FET, 612: Current control FET, 613: First electrode, 614: Insulator, 616: Organic compound layer, 617: Second electrode, 618: Light-emitting device, 623: FET, 700A: Electronic equipment, 700B: Electronic equipment, 721: Housing, 723: Mounting section, 727: Earphone section, 750: Earphone, 751: Display panel, 753: Optical component, 756: Display area 757: Frame, 758: Nose pad, 800A: Electronic equipment, 800B: Electronic equipment, 820: Display unit, 821: Housing, 822: Communication unit, 823: Mounting unit, 824: Control unit, 825: Imaging unit, 827: Earphone unit, 832: Lens, 1000: Insulating layer, 6500: Electronic equipment, 6501: Housing, 6502: Display unit, 6503: Power button, 6504: Button, 6505: Speaker, 6506: Microphone, 6507: Camera, 6508: Light source, 6510: Protective member, 6511: Display panel, 6512: Optical member, 6513: Touch sensor panel6515: FPC, 6516: IC, 6517: Printed circuit board, 6518: Battery, 7000: Display unit, 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: Pillar, 7411: Information terminal, 9000: Enclosure, 9001: Display unit, 9002: Camera, 9003: Speaker, 9005: Operation key, 9006: Connection terminal, 9007: Sensor, 9008: Microphone, 9050: Icon, 9051: Information, 9052: Information, 9053: Information, 9054: Information, 9055: Hinge, 9171: Portable information terminal, 9172: Portable information terminal, 9173: Tablet terminal, 9200: Portable information terminal, 9201: Portable information terminal,

Claims

1. Organic compounds represented by general formula (G1). (However, this excludes organic compounds represented by structural formulas (10) and (11) below.) (However, in the organic compound represented by the above general formula (G1), R ２０ ~R ２７ At least one of the groups is represented by the general formula (g1) above, and the others each independently represent hydrogen (including deuterium), a C1 to C10 alkyl group, a C3 to C10 cycloalkyl group, a C1 to C10 alkoxy group, a substituted or unsubstituted cyclic secondary amino group with 2 to 10 carbon atoms forming a ring, a substituted or unsubstituted C2 to C12 secondary amino group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group. Furthermore, in the group represented by the general formula (g1) above, R １ ~R １６ Each of the following independently represents hydrogen (including deuterium) or an alkyl group having 1 to 10 carbon atoms, and each of the following independently represents one of the values ​​from 0 to 3. Also, Ar １ (where m represents a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, and m represents any of 0 to 2, where m is 2, the two substituted or unsubstituted arylene groups may be the same or different.) 2. In claim 1, the R ２０ ~R ２７ An organic compound in which two of the groups are represented by the above general formula (g1).

3. The organic compound according to claim 2, wherein R ２０ to R ２３ any one of, and R ２４ to R ２７ any one of is a group represented by the above general formula (g1).

4. Organic compounds represented by general formula (G2). (However, this excludes organic compounds represented by structural formulas (10) and (11) below.) (However, in the organic compound represented by the above general formula (G2), R ２０ , R ２２ , R ２５ and R ２７ At least one of the groups is represented by the general formula (g1) above, and the others each independently represent hydrogen (including deuterium), a C1 to C10 alkyl group, a C3 to C10 cycloalkyl group, a C1 to C10 alkoxy group, a substituted or unsubstituted cyclic secondary amino group with 2 to 10 carbon atoms forming a ring, a substituted or unsubstituted C2 to C12 secondary amino group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group. Furthermore, in the group represented by the general formula (g1) above, R １ ~R １６ Each of the following independently represents hydrogen (including deuterium) or an alkyl group having 1 to 10 carbon atoms, and each of the following independently represents one of the values ​​from 0 to 3. Also, Ar １ (where m represents a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, and m represents any of 0 to 2, where m is 2, the two substituted or unsubstituted arylene groups may be the same or different.) 5. Organic compounds represented by general formula (G3). (However, this excludes organic compounds represented by structural formulas (10) and (11) below.) (However, in the organic compound represented by the above general formula (G3), R ２２ and R ２５ At least one of the groups is represented by the general formula (g1) above, and the others each independently represent hydrogen (including deuterium), a C1 to C10 alkyl group, a C3 to C10 cycloalkyl group, a C1 to C10 alkoxy group, a substituted or unsubstituted cyclic secondary amino group with 2 to 10 carbon atoms forming a ring, a substituted or unsubstituted C2 to C12 secondary amino group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group. Furthermore, in the group represented by the general formula (g1) above, R １ ~R １６ Each of the following independently represents hydrogen (including deuterium) or an alkyl group having 1 to 10 carbon atoms, and each of the following independently represents one of the values ​​from 0 to 3. Also, Ar １ (where m represents a substituted or unsubstituted arylene group, and m represents any value from 0 to 2; if m is 2, the two substituted or unsubstituted arylene groups may be the same or different.) 6. An organic compound in which the group represented by the general formula (g1) is the group represented by the following general formula (g2), according to any one of claims 1 to 5. (Note that in the group represented by the above general formula (g2), R １ ~R １６ Each of the following independently represents hydrogen (including deuterium) or an alkyl group having 1 to 10 carbon atoms, and u and v each independently represent one of 0 to 3. Also, Ar １ (where m represents a substituted or unsubstituted arylene group, and m represents any value from 0 to 2; if m is 2, the two substituted or unsubstituted arylene groups may be the same or different.) 7. The organic compound according to claim 6, wherein u and v each independently represent 0 or 1.

8. An organic compound in which the group represented by the general formula (g1) is the group represented by the following general formula (g3), according to any one of claims 1 to 5. (Note that in the group represented by the above general formula (g3), R １ ~R １６ Each of these independently represents hydrogen (including deuterium) or an alkyl group having 1 to 10 carbon atoms, Ar １ (where m represents a substituted or unsubstituted arylene group, and m represents any value from 0 to 2; if m is 2, the two substituted or unsubstituted arylene groups may be the same or different.) 9. An organic compound in which the group represented by the general formula (g1) is the group represented by the following general formula (g4), according to any one of claims 1 to 5. (Note that in the group represented by the above general formula (g3), R １ ~R １６ Each of these independently represents hydrogen (including deuterium) or an alkyl group having 1 to 10 carbon atoms, Ar １ (where m represents a substituted or unsubstituted arylene group, and m represents any value from 0 to 2; if m is 2, the two substituted or unsubstituted arylene groups may be the same or different.) 10. A material for an intermediate layer of a tandem light-emitting device comprising the organic compound according to any one of claims 1 to 5.

11. A tandem-type light-emitting device using the organic compound described in any one of claims 1 to 5 as an intermediate layer.

12. A tandem light-emitting device using an organic compound according to any one of claims 1 to 5 and a metal or metal compound as an intermediate layer.

13. A tandem light-emitting device using an organic compound according to any one of claims 1 to 5 and an organic compound having at least one of a pyridine skeleton and a diazine skeleton as an intermediate layer.

14. A tandem light-emitting device having an intermediate layer comprising an organic compound according to any one of claims 1 to 5, an organic compound having at least one of a pyridine skeleton and a diazine skeleton, and a metal or a metallic compound.

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