Organic compound and light-emitting device

Abstract

To provide an electron-injection organic compound capable of providing a high-performance semiconductor device, and a light-emitting device employing the organic compound.SOLUTION: An organic compound represented by the general formula (G1) in the figure and a light-emitting device employing the organic compound are provided. Note that, in the general formula (G1), R1 to R8 each independently represent any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic hydrocarbon group having 2 to 30 carbon atoms, and a group represented by the structural formula (R-1) in the figure. Note that at least two of the R1 to R8 each represent a group other than hydrogen and that one to four thereof each represent the group represented by the structural formula (R-1).SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] One aspect of the present invention relates to an organic compound and a light-emitting device.

[0002] It should be noted that one aspect of the present invention is not limited to the above-mentioned technical field. Examples of technical fields of one aspect of the present invention include semiconductor devices, display devices, light-emitting devices, energy storage devices, memory devices, electronic devices, lighting devices, input devices (e.g., touch sensors), input / output devices (e.g., touch panels), methods for driving them, or methods for manufacturing them. [Background technology]

[0003] In recent years, display devices have been expected to have applications in a variety of uses. For example, large-scale display devices are used in home television systems (also called televisions or television receivers), digital signage, and PID (Public Information Display). Furthermore, development is progressing on mobile information terminals such as smartphones and tablet devices equipped with touch panels.

[0004] At the same time, there is a demand for higher resolution display devices. Devices that require high-resolution display devices, such as those for virtual reality (VR), augmented reality (AR), substitutional reality (SR), and mixed reality (MR), are being actively developed.

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

[0006] To obtain higher-resolution light-emitting devices using organic EL devices, research is being conducted on patterning organic layers using photolithography methods with photoresists, as an alternative to deposition methods using metal masks. By using photolithography, it is possible to obtain high-resolution display devices with EL layer spacing of several micrometers (see, for example, Patent Document 1). [Prior art documents] [Patent Documents]

[0007] [Patent Document 1] Special Publication No. 2018-521459 [Patent Document 2] Japanese Patent Publication No. 2017-173056 [Overview of the project] [Problems that the invention aims to solve]

[0008] It has long been known that exposure to atmospheric components such as water and oxygen can affect the initial characteristics or reliability of EL layers, and it has been common practice to handle them in a near-vacuum environment. In particular, alkali metals or alkaline earth metals, or compounds thereof, are used for the intermediate layer in light-emitting devices having an electron injection layer or tandem structure. These metals and compounds are highly reactive with water or oxygen, and if the surface of the EL layer is exposed to the atmosphere, it deteriorates rapidly and ceases to function as an electron injection layer or intermediate layer.

[0009] However, as mentioned above, the process of processing using photolithography inevitably requires exposing the surface of the EL layer to the atmosphere.

[0010] In addition, 1,1'-pyridine-2,6-diyl-bis(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine) (abbreviated as hpp2Py) is an organic compound that can be used as an intermediate layer in light-emitting devices having an electron injection layer or tandem structure, instead of the alkali metals or alkaline earth metals or their compounds mentioned above. However, it has high solubility in water and is susceptible to the effects of moisture in the atmosphere.

[0011] Therefore, one aspect of the present invention aims to provide an organic compound having electron injection properties. Alternatively, another aspect of the present invention aims to provide an organic compound having electron injection properties and low water solubility. Alternatively, another aspect of the present invention aims to provide a light-emitting device that can be used in high-definition display devices. Alternatively, another aspect of the present invention aims to provide a tandem-type light-emitting device that can be used in high-definition display devices. Alternatively, another aspect of the present invention aims to provide a highly reliable light-emitting device that can be used in high-definition display devices. Alternatively, another aspect of the present invention aims to provide a highly reliable tandem-type light-emitting device that can be used in high-definition display devices.

[0012] Alternatively, another aspect of the present invention aims to provide a highly reliable display device. Alternatively, another aspect of the present invention aims to provide a high-definition display device. Alternatively, another aspect of the present invention aims to provide a high-definition and highly reliable display device.

[0013] Alternatively, the objectives are to provide novel organic compounds, novel light-emitting devices, novel display devices, novel display modules, and novel electronic devices, respectively.

[0014] Furthermore, the description of these problems does not preclude the existence of other problems. One aspect of the present invention does not necessarily have to solve all of these problems. It is possible to extract other problems from the description in the specification, drawings, and claims. [Means for solving the problem]

[0015] In one aspect of the present invention, an organic compound represented by the following general formula (G1) is provided.

[0016] [ka]

[0017] However, in the above general formula (G1), R 1 ~R 8 Each of these is independently one of hydrogen, a C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group, a substituted or unsubstituted C2 to C30 heteroaromatic hydrocarbon group, and a group represented by the following structural formula (R-1). However, the R 1 ~R 8 The group consists of two or more groups other than hydrogen, and one to four groups represented by the following structural formula (R-1).

[0018] [ka]

[0019] Alternatively, in another aspect of the present invention, in the above configuration, the R 1 ~R 8 Of these, one is a group represented by the following structural formula (R-1), and one is an aromatic hydrocarbon group having 6 to 30 carbon atoms having a group represented by the following general formula (g1), and the remaining ones are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic hydrocarbon group having 2 to 30 carbon atoms, and a group represented by the following structural formula (R-1), and the R 1 ~R 8 This is an organic compound in which 1 to 3 of its components are groups represented by the following structural formula (R-1).

[0020] [Chemical formula]

[0021] [Chemical formula]

[0022] However, in the general formula (g1), one of R 11 to R 18 is a bond and is bonded to an aromatic hydrocarbon group having 6 to 30 carbon atoms having the group represented by the general formula (g1), one of them is a group represented by the above structural formula (R-1), and the rest are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic hydrocarbon group having 2 to 30 carbon atoms, and any one of the groups represented by the above structural formula (R-1), and R 11 to R 18 are such that 1 or more and 3 or less of them are groups represented by the above structural formula (R-1).

[0023] Or, another aspect of the present invention is an organic compound represented by the following general formula (G2).

[0024] [Chemical formula]

[0025] However, in the general formula (G2), R 1 , R 3 , R 6 and R 8 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic hydrocarbon group having 2 to 30 carbon atoms, and any one of the groups represented by the following structural formula (R-1). However, R 1 , R 3 , R6 and R 8 The group consists of two or more groups other than hydrogen, and one to four groups represented by the following structural formula (R-1).

[0026] [ka]

[0027] Alternatively, in another aspect of the present invention, in the above configuration, the R 1 , R 3 , R 6 and R 8 The organic compound is one in which any one of the groups is represented by the following structural formula (R-1), any one of which is a substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, the rest are all hydrogen atoms, and the substituent on the substituted aromatic hydrocarbon group having 6 to 30 carbon atoms is a group represented by the following general formula (g2).

[0028] [ka]

[0029] [ka]

[0030] However, in the above general formula (g2), R 11 , R 13 , R 16 and R 18 One of these is a bonding site, bonded to an aromatic hydrocarbon group having 6 to 30 carbon atoms and the substituent, one of which is the group represented by the above structural formula (R-1), and the rest are hydrogen atoms.

[0031] Alternatively, another aspect of the present invention is an organic compound represented by the following general formula (G3).

[0032] [ka]

[0033] However, in the above general formula (G3), R 1 and R 8 The group is one or both of which are represented by the following structural formula (R-1), and the remaining group is one of the following: an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic hydrocarbon group having 2 to 30 carbon atoms.

[0034] [ka]

[0035] Alternatively, in another aspect of the present invention, in the above configuration, the R 1 The group is represented by the following structural formula (R-1), and R 8 The compound is an organic compound in which a substituent is a C6 to C30 aromatic hydrocarbon group having substituents, and the substituent on the C6 to C30 aromatic hydrocarbon group having substituents is a group represented by the following general formula (g3).

[0036] [ka]

[0037] [ka]

[0038] However, in the above general formula (g3), R 11 The bond is bonded to an aromatic hydrocarbon group having 6 to 30 carbon atoms and the substituent, R 18 This is the group represented by the above structural formula (R-1).

[0039] Alternatively, another aspect of the present invention is an organic compound represented by the following general formula (G4).

[0040] [ka]

[0041] However, in the above general formula (G4), R 3 and R 6 The group is one or both of which are represented by the following structural formula (R-1), and the remaining group is one of the following: an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic hydrocarbon group having 2 to 30 carbon atoms.

[0042] [ka]

[0043] Alternatively, in another aspect of the present invention, in the above configuration, the R 3 The group is represented by the following structural formula (R-1), and R 6 The compound is an organic compound in which a substituent is a C6 to C30 aromatic hydrocarbon group having substituents, and the substituent on the C6 to C30 aromatic hydrocarbon group having substituents is a group represented by the following general formula (g4).

[0044] [ka]

[0045] [ka]

[0046] However, in the above general formula (g4), R 13 R is a bonding hand that is bonded to an aromatic hydrocarbon group having 6 to 30 carbon atoms and the substituents, 16 This is the group represented by the above structural formula (R-1).

[0047] Alternatively, another aspect of the present invention is an organic compound in the above configuration in which the glass transition temperature of the organic compound represented by any one of the general formulas (G1) to (G4) is 70°C or higher.

[0048] Another aspect of the present invention is a light-emitting device having any of the above-mentioned organic compounds.

[0049] Alternatively, another aspect of the present invention is a light-emitting device comprising a first electrode, a second electrode, a first light-emitting unit, an intermediate layer, and a second light-emitting unit, wherein the first light-emitting unit is located between the first electrode and the intermediate layer, and the second light-emitting unit is located between the intermediate layer and the second electrode, and the intermediate layer is any of the above organic compounds.

[0050] Alternatively, another aspect of the present invention is a display module having the above-mentioned light-emitting device and at least one of a connector and an integrated circuit.

[0051] Alternatively, another aspect of the present invention is an electronic device having the above-mentioned light-emitting device and at least one of a housing, a battery, a camera, a speaker, and a microphone. [Effects of the Invention]

[0052] In one aspect of the present invention, an organic compound having electron injection properties can be provided. Alternatively, in another aspect of the present invention, an organic compound having electron injection properties and low water solubility can be provided. Alternatively, in another aspect of the present invention, a light-emitting device usable in high-definition display devices can be provided. Alternatively, in another aspect of the present invention, a tandem-type light-emitting device usable in high-definition display devices can be provided. Alternatively, in another aspect of the present invention, a highly reliable light-emitting device usable in high-definition display devices can be provided. Alternatively, in another aspect of the present invention, a highly reliable tandem-type light-emitting device usable in high-definition display devices can be provided.

[0053] Furthermore, one aspect of the present invention can provide a highly reliable display device. Furthermore, one aspect of the present invention can provide a display device that is high resolution and has good display performance. Furthermore, one aspect of the present invention can provide a display device that has good display quality and good display performance.

[0054] Furthermore, one aspect of the present invention can provide a novel display device, a novel display module, and a novel electronic device.

[0055] Furthermore, the description of these effects does not preclude the existence of other effects. One aspect of the present invention does not necessarily have to possess all of these effects. Other effects can be extracted from the description, drawings, and claims. [Brief explanation of the drawing]

[0056] [Figure 1] Figures 1(A) through 1(C) are diagrams illustrating light-emitting devices. [Figure 2] Figures 2(A) and 2(B) are diagrams illustrating light-emitting devices. [Figure 3] Figures 3(A) and 3(B) are a top view and a cross-sectional view of the light-emitting device. [Figure 4] Figures 4(A) to 4(E) are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 5] Figures 5(A) to 5(D) are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 6] Figures 6(A) to 6(D) are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 7] Figures 7(A) to 7(C) are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 8] Figures 8(A) to 8(C) are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 9] Figures 9(A) to 9(C) are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 10]Figures 10(A) and 10(B) are perspective views showing examples of the display module configuration. [Figure 11] Figures 11(A) and 11(B) are cross-sectional views showing examples of the configuration of a display device. [Figure 12] Figure 12 is a perspective view showing an example of a display device configuration. [Figure 13] Figure 13 is a cross-sectional view showing an example of the configuration of a display device. [Figure 14] Figure 14 is a cross-sectional view showing an example of the configuration of a display device. [Figure 15] Figure 15 is a cross-sectional view showing an example of the configuration of a display device. [Figure 16] Figures 16(A) to 16(D) show examples of electronic devices. [Figure 17] Figures 17(A) through 17(F) show examples of electronic devices. [Figure 18] Figures 18(A) to 18(G) show examples of electronic devices. [Figure 19] Figure 19 shows the luminance-current density characteristics of light-emitting device 1, light-emitting device 2, and comparative light-emitting device 1. [Figure 20] Figure 20 shows the luminance-voltage characteristics of light-emitting device 1, light-emitting device 2, and comparison light-emitting device 1. [Figure 21] Figure 21 shows the current efficiency-luminance characteristics of light-emitting device 1, light-emitting device 2, and comparative light-emitting device 1. [Figure 22] Figure 22 shows the current-voltage characteristics of light-emitting device 1, light-emitting device 2, and comparison light-emitting device 1. [Figure 23] Figure 23 shows the emission spectra of light-emitting device 1, light-emitting device 2, and reference light-emitting device 1. [Figure 24] Figure 24 shows the normalized luminance-time variation characteristics of light-emitting device 1, light-emitting device 2, and comparative light-emitting device 1. [Figure 25] Figure 25 shows the luminance-current density characteristics of light-emitting device 3 and comparison light-emitting device 2. [Figure 26] Figure 26 shows the luminance-voltage characteristics of light-emitting device 3 and comparison light-emitting device 2. [Figure 27] Figure 27 shows the current efficiency-luminance characteristics of light-emitting device 3 and comparative light-emitting device 2. [Figure 28] Figure 28 shows the current-voltage characteristics of light-emitting device 3 and comparison light-emitting device 2. [Figure 29] Figure 29 shows the emission spectra of light-emitting device 3 and reference light-emitting device 2. [Figure 30] Figure 30 shows the normalized luminance-time variation characteristics of light-emitting device 3 and comparative light-emitting device 2. [Figure 31] Figure 31 shows the 1H NMR chart for 2,9hpp2Phen. [Figure 32] Figure 32 shows the 1H NMR chart for 4,7 hpp2Phen. [Figure 33] Figure 33 shows the 1H NMR chart for 9Ph-2hppPhen. [Figure 34] Figures 34(A) through 34(C) show the 1H NMR chart of mhppPhen2P. [Figure 35] Figure 35 shows the luminance-current density characteristics of the light-emitting device 4. [Figure 36] Figure 36 shows the luminance-voltage characteristics of the light-emitting device 4. [Figure 37] Figure 37 shows the current efficiency-luminance characteristics of the light-emitting device 4. [Figure 38] Figure 38 shows the current-voltage characteristics of the light-emitting device 4. [Figure 39] Figure 39 shows the emission spectrum of the light-emitting device 4. [Figure 40] Figure 40 shows the normalized luminance-time variation characteristics of the light-emitting device 4. [Modes for carrying out the invention]

[0057] Embodiments will be described in detail with reference to the drawings. However, it will be readily apparent to those skilled in the art that the present invention is not limited to the following description, and that its form and details can be modified in various ways without departing from the spirit and scope of the present invention. Accordingly, the present invention shall not be construed as being limited to the descriptions of the embodiments shown below.

[0058] 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.

[0059] (Embodiment 1) Vacuum deposition using a metal mask (mask deposition) is widely used as one method for fabricating organic semiconductor 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 and spacing issues with the substrate. On the other hand, it is expected that organic semiconductor devices with more intricate patterns can be realized by processing the shape of organic semiconductor films using photolithography. Furthermore, since photolithography can be easily applied to large areas compared to mask deposition, research on processing organic semiconductor films using photolithography is progressing.

[0060] On the other hand, it has long been known that the EL layer in organic EL devices is affected in its initial characteristics or reliability when exposed to atmospheric components such as water and oxygen, and it has been common practice to handle it in a near-vacuum environment. In particular, alkali metals or alkaline earth metals, or compounds thereof, are used in the intermediate layer of light-emitting devices having an electron injection layer or tandem structure. However, these metals and compounds are highly reactive with water or oxygen, and if the surface of the EL layer is exposed to the atmosphere, it deteriorates rapidly and ceases to function as an intermediate layer.

[0061] In addition, 1,1'-pyridine-2,6-diyl-bis(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine) (abbreviated as hpp2Py) has been proposed as an organic compound that can be used in the electron injection layer instead of the alkali metals or alkaline earth metals or their compounds mentioned above, but it has high solubility in water and is susceptible to the effects of moisture in the atmosphere.

[0062] However, as mentioned above, the process of processing using photolithography inevitably requires exposing the surface of the EL layer to the atmosphere.

[0063] Therefore, in one aspect of the present invention, an organic compound represented by the following general formula (G1) is provided.

[0064] [ka]

[0065] However, in the above general formula (G1), R 1 ~R 8 Each of these is independently one of hydrogen, a C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group, a substituted or unsubstituted C2 to C30 heteroaromatic hydrocarbon group, and a group represented by the following structural formula (R-1). However, the R 1 ~R 8 The group consists of two or more groups other than hydrogen, and one to four groups represented by the following structural formula (R-1).

[0066] [ka]

[0067] An organic compound according to one embodiment of the present invention, having the above-described configuration, possesses electron injection and electron transport properties, and can therefore be used as an electron injection layer in an electron-emitting device and as an intermediate layer (N-type layer) in a tandem-type electron-emitting device, in place of alkali metals or alkaline earth metals, or these compounds.

[0068] Furthermore, because this organic compound has lower solubility in water than hpp2Py mentioned earlier, it is more resistant to exposure to air and aqueous solutions during photolithography, making it possible to provide a light-emitting device with excellent properties.

[0069] Furthermore, light-emitting devices using this organic compound can provide light-emitting devices with better initial characteristics and reliability than those using hpp2Py. It should be noted that hpp2Py and the organic compound according to one embodiment of the present invention represented by the general formula (G1) above are less likely to cause metal contamination of the manufacturing line than alkali metals or alkaline earth metals, or compounds thereof, and are easily vapor-deposited, making them more suitable for use in light-emitting devices manufactured using a photolithography process. Of course, they are also effective in light-emitting devices that do not use a photolithography process.

[0070] Furthermore, the organic compound according to one embodiment of the present invention, represented by the general formula (G1) above, has a relatively high glass transition temperature, with a value of 70°C or higher, making it possible to provide a highly heat-resistant light-emitting device. It can also withstand the heating process in the photolithography process, making it possible to provide a high-definition light-emitting device with excellent properties.

[0071] Furthermore, the organic compound according to one embodiment of the present invention, represented by the general formula (G1) above, has a relatively low LUMO level, which allows for good electron injection and transport properties, and makes it possible to provide a light-emitting device with a good drive voltage.

[0072] Furthermore, the organic compound represented by the above general formula (G1) is preferably a dimer of the phenanthroline skeleton because it improves heat resistance and electron injection. That is, in the organic compound represented by the general formula (G1), R 1 ~R 8 A preferred organic compound is one in which the group is represented by the above structural formula (R-1), and the other in which the group is represented by the following general formula (g1), and is an aromatic hydrocarbon group having 6 to 30 carbon atoms.

[0073] Note, R 1 ~R 8 The remaining six are each independently hydrogen, a C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group, a substituted or unsubstituted C2 to C30 heteroaromatic hydrocarbon group, and the group represented by the above structural formula (R-1), and the R 1 ~R 8 The group in which 1 to 3 of the elements is represented by the above structural formula (R-1).

[0074] [ka]

[0075] However, in the above general formula (g1), R 11 ~R 18 One of them is a bonding site, one of them is a group represented by the above structural formula (R-1), and the remaining ones are each independently hydrogen, a C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group, a substituted or unsubstituted C2 to C30 heteroaromatic hydrocarbon group, and a group represented by the above structural formula (R-1), and the R 11 ~R 18 The group in which 1 to 3 of the elements is represented by the above structural formula (R-1).

[0076] Furthermore, in the organic compound represented by the above general formula (G1), R 2 , R 4, R 5 , R 7 The fact that the compound is hydrogen is preferable because it is easy to synthesize due to the availability of various types of raw materials on the market, and the synthesis cost is low. In other words, another aspect of the present invention is that an organic compound represented by the following general formula (G2) is preferred.

[0077] [ka]

[0078] However, in the above general formula (G2), R 1 , R 3 , R 6 and R 8 Each of these is independently one of hydrogen, a C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group, a substituted or unsubstituted C2 to C30 heteroaromatic hydrocarbon group, and the group represented by the above structural formula (R-1). However, the R 1 , R 3 , R 6 and R 8 In this structure, two or more are groups other than hydrogen, and one to four are groups represented by the above structural formula (R-1).

[0079] Furthermore, the organic compound represented by the above general formula (G2) is preferably a dimer of the phenanthroline skeleton because it improves heat resistance and electron injection. That is, in the organic compound represented by the general formula (G2), R 1 , R 3 , R 6 and R 8 A preferred organic compound is one in which the group is represented by the above structural formula (R-1), and the other in which the group is represented by the following general formula (g2), and is an aromatic hydrocarbon group having 6 to 30 carbon atoms.

[0080] [ka]

[0081] However, in the above general formula (g2), R 11 , R 13 , R 16 and R 18 One of the following is a bonding site, one of which is a group represented by the above structural formula (R-1), and the remaining ones are independently hydrogen, a C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group, a substituted or unsubstituted C2 to C30 heteroaromatic hydrocarbon group, and a group represented by the above structural formula (R-1), R 11 , R 13 , R 16 and R 18 , of which 1 to 3 is the group represented by the above structural formula (R-1). 11 , R 13 , R 16 and R 18 Of these, the group that is neither a bonding group nor a group represented by structural formula (R-1) is preferably hydrogen.

[0082] Furthermore, in the organic compound represented by the above general formula (G1), R 1 and R 8 The presence of substituents is preferable because it improves electron injection. That is, in another aspect of the present invention, an organic compound represented by the following general formula (G3) is preferred.

[0083] [ka]

[0084] However, in the above general formula (G3), R 1 and R 8 The group is one or both of which are represented by the above structural formula (R-1), and the remainder is one of the following: an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic hydrocarbon group having 2 to 30 carbon atoms.

[0085] Incidentally, the organic compound represented by the above general formula (G3) is preferably a dimer of a phenanthroline skeleton because its heat resistance and electron injection property are improved. That is, in the organic compound represented by the general formula (G3), R 1 and R 8 One of them is a group represented by the above structural formula (R-1), and an organic compound having one group represented by the following general formula (g3) and having an aromatic hydrocarbon group having 6 to 30 carbon atoms is preferable.

[0086]

Chemical formula

[0087] However, in the above general formula (g3), R 11 and R 18 One of them is a bond, and one of them is a group represented by the above structural formula (R-1).

[0088] In addition, in the organic compound represented by the above general formula (G1), it is preferable that R 3 and R 6 have substituents because the electron injection property is improved. That is, another aspect of the present invention preferably uses an organic compound represented by the following general formula (G4).

[0089]

Chemical formula

[0090] However, in the above general formula (G4), R 3 and R 6 One or both of them are groups represented by the above structural formula (R-1), and the rest are any of an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaromatic hydrocarbon group having 2 to 30 carbon atoms.

[0091] Incidentally, the organic compound represented by the above general formula (G4) is preferably a dimer of a phenanthroline skeleton because its heat resistance and electron injection property are improved. That is, in the organic compound represented by the general formula (G4), one of R 3 and R 6 is a group represented by the above structural formula (R-1), and an organic compound having a group represented by the following general formula (g4) and being an aromatic hydrocarbon group having 6 to 30 carbon atoms is preferable.

[0092] [Chemical formula]

[0093] However, in the above general formula (g4), one of R 13 and R 16 is a bond, and one of them is a group represented by the above structural formula (R-1).

[0094] Incidentally, in this specification, examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, and the like.

[0095] Examples of the cycloalkyl group having 3 to 7 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-methylcyclohexyl group, a 2,6-dimethylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like. When these have a substituent, examples of the substituent include an alkyl group having 1 to 6 carbon atoms and a phenyl group.

[0096] Examples of substituted or unsubstituted aromatic hydrocarbon groups having 6 to 30 carbon atoms include groups having a benzene ring, naphthalene ring, fluorene ring, spirofluorene ring, phenanthrene ring, or triphenylene ring. Specifically, examples include phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, mesityl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, 1-naphthyl group, 2-naphthyl group, fluorenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, spirofluorenyl group, phenanthrenyl group, terphenyl group, anthracenyl group, fluoranthenyl group, etc. If these groups have substituents, examples of substituents include alkyl groups having 1 to 6 carbon atoms and phenyl groups.

[0097] Examples of substituted or unsubstituted heteroaromatic hydrocarbon groups having 2 to 30 carbon atoms include groups having a pyrrole ring, pyridine ring, diazine ring, triazine ring, imidazole ring, triazole ring, thiophene ring, or furan ring. If these groups have substituents, examples of substituents include alkyl groups having 1 to 6 carbon atoms and phenyl groups.

[0098] Aromatic hydrocarbon groups having 6 to 30 carbon atoms and a group represented by any of the above general formulas (g1) to (g4) include groups having a benzene ring, naphthalene ring, fluorene ring, spirofluorene ring, phenanthrene ring, or triphenylene ring. Specifically, examples include phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, mesityl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, 1-naphthyl group, 2-naphthyl group, fluorenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, spirofluorenyl group, phenanthrenyl group, terphenyl group, anthracenyl group, fluoranthenyl group, etc., but the phenyl group is particularly preferred. In this case, the bond position of the group represented by any of the above general formulas (g1) to (g4) on the phenyl group is preferably the meta position from the viewpoint of heat resistance.

[0099] Furthermore, with regard to the hydrogen contained in the organic compounds represented by any of the general formulas (G1) to (G4) described above, this specification also includes cases where the hydrogen is deuterium. That is, for example, when it is stated that R is hydrogen, it also includes cases where it is deuterium. Also, for example, in the above structural formula (R-1), a hydrogen atom is bonded to a carbon atom that does not have a substituent listed, and this also includes cases where the hydrogen atom is deuterium.

[0100] Examples of organic compounds represented by any of the general formulas (G1) to (G4) described above include the organic compounds represented by the following structural formulas (100) to (141).

[0101] [ka]

[0102] [ka]

[0103] [ka]

[0104] [ka]

[0105] The organic compound represented by the above general formula (G1) can be obtained by coupling a phenanthroline derivative halogen compound or a compound having a triflate group (a1) with 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine via a Buchwald-Hartwig reaction, as shown in the synthesis scheme below.

[0106] [ka]

[0107] In the above general formula (a1), X 1 ~X 8 Each of these is independently one of hydrogen, deuterium, a C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaromatic hydrocarbon group, and a group represented by the following structural formula (R-1), X 1 ~X 8 At least one of these represents a halogen or a triflate group. Also, X in the above general formula (a1) 1 ~X 8 In this equation, two or more substituents other than hydrogen and deuterium are present. Furthermore, n in the above reaction equation is a positive number, and it is preferable that the value of n is greater than the number of halogen or triflate groups in the above general formula (a1).

[0108] In the above general formula (G1), R 1 ~R 8 Each of these is independently one of the following: hydrogen, deuterium, a C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaromatic hydrocarbon group, and a group represented by the following structural formula (R-1). However, R 1 ~R 8 The group consists of two or more groups other than hydrogen and deuterium, and one to four groups represented by the following structural formula (R-1).

[0109] [ka]

[0110] Examples of palladium catalysts that can be used in the coupling reaction represented by the above synthesis scheme include palladium(II) acetate, tetrakis(triphenylphosphine)palladium(O), and bis(triphenylphosphine)palladium(II) dichloride.

[0111] Examples of ligands for the above palladium catalyst include (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, tri(ortho-tolyl)phosphine, triphenylphosphine, and tricyclohexylphosphine.

[0112] Examples of bases that can be used in the coupling reaction represented by the above synthesis scheme include organic bases such as potassium-tert-butoxide, and inorganic bases such as potassium carbonate and sodium carbonate.

[0113] In the coupling reaction represented by the above synthesis scheme, suitable solvents include toluene, xylene, mesitylene, benzene, tetrahydrofuran, and dioxane. However, the solvents that can be used are not limited to these.

[0114] Furthermore, the reactions carried out in the above synthesis scheme are not limited to the Buchwald-Hartwig reaction; other reactions such as the Migita-Kosugi-Still coupling reaction using organotin compounds, coupling reactions using Grignard reagents, the Ullmann reaction using copper or copper compounds, and nucleophilic substitution reactions can also be used.

[0115] Furthermore, various types of compounds in the above general formula (a1) are commercially available or can be synthesized.

[0116] While organic compounds according to one aspect of the present invention can be synthesized as described above, the present invention is not limited thereto, and may be synthesized by other synthesis methods.

[0117] (Embodiment 2) This embodiment will describe in detail a light-emitting device according to one aspect of the present invention.

[0118] Figure 1 is a schematic diagram of a light-emitting device according to one embodiment of the present invention. The light-emitting device has a first electrode 101 provided on an insulator 100, and an organic compound layer 103 between the first electrode 101 and a second electrode 102. The organic compound layer 103 contains an organic compound represented by general formulas (G1) to (G4) shown in Embodiment 1, and also has at least a light-emitting layer 113. The light-emitting layer 113 is a layer containing a light-emitting substance and emits light when a voltage is applied between the first electrode 101 and the second electrode 102.

[0119] In addition to the light-emitting layer 113, the organic compound layer 103 preferably has functional layers such as a hole injection layer 111, a hole transport layer 112, an electron transport layer 114, and an electron injection layer 115, as shown in Figure 1(A). The organic compound layer 103 may also include functional layers other than those described above, such as a hole blocking layer, an electron blocking layer, an exciton blocking layer, and a charge generation layer. Conversely, none of the above layers may be provided.

[0120] In Embodiment 1, the organic compound represented by any of general formulas (G1) to (G4) is contained in the organic compound layer 103. Since the organic compound has electron transport properties, it is preferable that it is contained in the electron transport layer 114 or the electron injection layer 115. In particular, it is preferable that it is contained in the electron injection layer 115 because it has electron injection properties.

[0121] The organic compound represented by any of the above general formulas (G1) to (G4) has lower solubility in water than hpp2Py mentioned earlier, making it more resistant to exposure to air and aqueous solutions during photolithography and enabling the provision of light-emitting devices with good properties.

[0122] A light-emitting device using an organic compound according to one aspect of the present invention can provide a light-emitting device with better initial characteristics and reliability than a light-emitting device using hpp2Py. Furthermore, unlike alkali metals or alkaline earth metals, or compounds thereof, the organic compound according to one aspect of the present invention has less risk of metal contamination of the manufacturing line and is easy to deposit, making it more suitable for use in light-emitting devices manufactured using a photolithography process. Of course, it is also effective to use it in light-emitting devices that do not use a photolithography process.

[0123] Furthermore, the organic compound according to one embodiment of the present invention, represented by any of the above general formulas (G1) to (G4), has a relatively high glass transition temperature, with a value of 70°C or higher, making it possible to provide a highly heat-resistant light-emitting device. It can also withstand the heating process in the photolithography process, making it possible to provide a high-definition light-emitting device with excellent properties.

[0124] In this embodiment, the first electrode 101 is described as an electrode including an anode, and the second electrode 102 is described as an electrode including a cathode, but this can be reversed. The first electrode 101 and the second electrode 102 are formed as a single-layer structure or a laminated structure, and in the case of 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 the material can be selected according to the required properties such as resistance, ease of processing, reflectivity, light transmittance, and stability.

[0125] The anode is preferably formed using a metal, alloy, conductive compound, or mixture thereof with a high work function (specifically, 4.0 eV or higher). Specifically, examples include indium tin oxide (ITO), indium tin silicon oxide (ITSO) containing silicon or silicon oxide, indium zinc oxide, and indium oxide (IWZO) containing tungsten oxide and zinc oxide. These conductive metal oxide films are usually deposited by sputtering, but they may also be fabricated using methods such as the sol-gel method. An example of a fabrication method is to form indium zinc oxide by sputtering using a target to which 1 to 20 wt% zinc oxide is added to indium oxide. Furthermore, indium oxide (IWZO) containing tungsten oxide and zinc oxide can also be formed by sputtering using a target containing 0.5-5 wt% tungsten oxide and 0.1-1 wt% zinc oxide relative to indium oxide. Other materials that can be used for the anode 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. Graphene can also be used as the anode material. 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), the electrode material can be selected regardless of the work function.

[0126] The hole injection layer 111 is provided in contact with the anode and has the function of facilitating the injection of holes into the organic compound layer 103. The hole injection layer 111 can be formed from phthalocyanine-based compounds such as phthalocyanine (abbreviated as H2Pc), phthalocyanine-based complex compounds such as copper phthalocyanine (abbreviated as CuPc), aromatic amine compounds such as 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated as DPAB) and 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviated as DNTPD), or polymers such as poly(3,4-ethylenedioxythiophene) / (polystyrene sulfonic acid) (abbreviated as PEDOT / PSS).

[0127] Furthermore, the hole injection layer 111 may be formed from a substance having electron-accepting properties. Examples of substances having electron-accepting properties include organic compounds having electron-withdrawing groups (halogen groups, cyano groups, etc.), such as 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviated as F4-TCNQ), chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexazatriphenylene (abbreviated as HAT-CN), 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviated as F6-TCNNQ), and 2-(7-dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyrene-2-ylidene)malononitrile. In particular, compounds in which an electron-withdrawing group is bonded to a condensed aromatic ring having multiple heteroatoms, such as HAT-CN, are thermally stable and preferred. Furthermore, radialene derivatives having an electron-withdrawing group (especially halogen groups such as fluoro groups, cyano groups, etc.) are preferred because they have very high electron-accepting properties. Specific examples include α,α',α''-1,2,3-cyclopropanetriylidenates[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α',α''-1,2,3-cyclopropanetriylidenates[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], and α,α',α''-1,2,3-cyclopropanetriylidenates[2,3,4,5,6-pentafluorobenzeneacetonitrile]. In addition to the organic compounds mentioned above, other acceptor materials that can be used include transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide.

[0128] Furthermore, it is preferable that the hole injection layer 111 be formed from a composite material containing the acceptor material and an organic compound having hole transport properties.

[0129] Various organic compounds with hole-transporting properties can be used 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 organic compound has a hole mobility of / Vs or greater. The hole-transporting organic compound 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.

[0130] Organic compounds having such hole-transporting properties are more preferably those having one of the following skeletons: carbazole, dibenzofuran, dibenzothiophene, or anthracene. 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, organic compounds having these hole-transporting properties are preferred if they 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.

[0131] Organic compounds exhibiting hole transport properties as described above include, specifically, N-(4-biphenyl)-6,N-diphenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BnfABP), N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf), 4,4'-bis(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)-4''-phenyltriphenylamine (abbreviation: BnfBB1BP), and N,N-bis(4-biphenyl)be Nzo[b]naphtho[1,2-d]furan-6-amine (abbreviation: BBABnf(6)), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf(8)), N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviation: BBABnf(II)(4)), N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP), N-[4-(dibenzothiophen-4-yl)phenyl ]-N-phenyl-4-biphenylamine (abbreviation: ThBA1BP), 4-(2-naphthyl)-4',4''-diphenyltriphenylamine (abbreviation: BBAβNB), 4-[4-(2-naphthyl)phenyl]-4',4''-diphenyltriphenylamine (abbreviation: BBAβNBi), 4,4'-diphenyl-4''-(6;1'-binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβNB), 4,4'-diphenyl-4''-(7;1'-binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβ NB-03), 4,4'-diphenyl-4''-(7-phenyl)naphthyl-2-yltriphenylamine (abbreviation: BBAPβNB-03), 4,4'-diphenyl-4''-(6;2'-binaphthyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B), 4,4'-diphenyl-4''-(7;2'-binaphthyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B-03), 4,4'-diphenyl-4''-(4;2'-binaphthyl-1-yl)triphenylamine (abbreviation: BBAβNαNB), 4,4'-Diphenyl-4''-(5;2'-binaphthyl-1-yl)triphenylamine (abbreviation: BBAβNαNB-02), 4-(4-biphenylyl)-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: TPBiAβNB), 4-(3-biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: mTPBiAβNBi), 4-(4-biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4'' -Phenyltriphenylamine (abbreviation: TPBiAβNBi), 4-phenyl-4'-(1-naphthyl)triphenylamine (abbreviation: αNBA1BP), 4,4'-bis(1-naphthyl)triphenylamine (abbreviation: αNBB1BP), 4,4'-diphenyl-4''-[4'-(carbazole-9-yl)biphenyl-4-yl]triphenylamine (abbreviation: YGTBi1BP), 4'-[4-(3-phenyl-9H-carbazole-9-yl)phenyl]tris(1,1' -biphenyl-4-yl)amine (abbreviation: YGTBi1BP-02), 4-[4'-(carbazole-9-yl)biphenyl-4-yl]-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: YGTBiβNB), N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-N-[4-(1-naphthyl)phenyl]-9,9'-spirobio[9H-fluorene]-2-amine (abbreviation: PCBNBSF), N,N-bis([1,1'-biphenyl N,N-bis([1,1'-biphenyl-2-yl)-9,9'-spirobio[9H-fluorene]-2-amine (abbreviation: BBASF), N,N-bis([1,1'-biphenyl]-4-yl)-9,9'-spirobio[9H-fluorene]-4-amine (abbreviation: BBASF(4)), N-(1,1'-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobio[9H-fluorene]-4-amine (abbreviation: oFBiSF), N-(biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzofuran-4-amine (abbreviation: FrBiF), N-[4-(1-naphthyl)phenyl]-N-[3-(6-phenyldibenzofuran-4-yl)phenyl]-1-naphthylamine (abbreviation: mPDBfBNBN), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-phenyl-4'-[4-(9-phenylfluoren- 9-yl)phenyl]triphenylamine (abbreviation: BPAFLBi), 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazole-3 -yl)triphenylamine (abbreviation: PCBNBB), N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9'-spirobio[9H-fluorene]-2-amine (abbreviation: PCBASF), N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H-fluorene-2-amine (abbreviation: PCBBiF), N,N-bis(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobio[9H-fluorene-4- Amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio-9H-fluoren-3-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio-9H-fluoren-2-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio-9H-fluoren-1-amine, N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: PCAFLP(2)), N-(9,Examples include 9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine (abbreviation: PCAFLP(2)-02).

[0132] 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).

[0133] 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.

[0134] 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.

[0135] Furthermore, the material used in the hole injection layer 111 may be an organic compound represented by general formulas (G1) to (G4) as shown in Embodiment 1.

[0136] The hole transport layer 112 is formed by including a material having hole transport properties. The material having hole transport properties is 1 × 10 -6 cm 2 It is preferable that the hole mobility is greater than or equal to / Vs.

[0137] Materials exhibiting the above hole transport properties include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminobiphenyl (abbreviated as TPD), N,N'-bis(9,9'-spirobi[9H-fluoren]-2-yl)-N,N'-diphenyl-4,4'-diaminobiphenyl (abbreviated as BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated as BPAFLP), and 4-phenyl-3'-(9 -phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazole-3-yl) Compounds having an aromatic amine skeleton such as zole-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobio[9H-fluoren]-2-amine (abbreviation: PCBASF), 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)bis Phenyl (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(1,1'-biphenyl-3-yl)-3,3'-bi-9H-carbazole (abbreviation: BismBPCz), 9-(1,1'-biphenyl-3-yl)-9'-(1,1'-biphenyl-4-yl)-9H,9'H-3,3'-bicarbazole (abbreviation: mBPCCBP), 9-(2-naphthyl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (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- Il-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' Compounds having a carbazole skeleton such as ,1”-terphenyl]-4-yl-3,3'-9H,9'H-bicarbazole, N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: PCAFLP(2)), N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine (abbreviation: PCAFLP(2)-02), 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 substances listed as organic compounds with hole-transporting properties used in the composite material of the hole injection layer 111 can also be suitably used as materials constituting the hole transport layer 112.

[0138] The light-emitting layer 113 is a layer having a light-emitting substance, and preferably contains both a light-emitting substance and a host material. The light-emitting layer 113 may also contain other materials. Furthermore, it may be a laminate of two layers with different compositions.

[0139] The luminescent material can be a fluorescent material, a phosphorescent material, a material that exhibits thermally activated delayed fluorescence (TADF), or any other luminescent material.

[0140] Examples of materials that can be used as fluorescent materials in the light-emitting layer 113 include the following. Other fluorescent materials can also be used.

[0141] 5,6-Bis[4-(10-phenyl-9-antryl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-Bis[4'-(10-phenyl-9-antryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), N,N'-Diphenyl-N,N'-Bis[4-(9-phenyl-9H-fluoren-9-yl)phenyl]pyren-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-Bis(3-methylphenyl)-N,N'-Bis[3-(9-phenyl-9H-fluoren-9-yl )phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N,N'-bis[4-(9H-carbazole-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazole-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazole-9-yl)-4'-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-diphenyl-N-[4-( 10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra-tert-butylperylene (abbreviation: TBP), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBAPA), N,N''-(2-tert-butylanthracene-9,10-diyldi-4,1-phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine] (abbreviation: DPABPA), N,9 -Diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: 2PCAPPA), N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA), N,N,N',N',N'',N'',N''',N'''-octaphenyldibenzo[g,p]chrysene-2,7,10,15-tetraamine (abbreviation: DBC1), coumarin 30, N-(9,10-diphenyl-2-anthryl)-N,9-Diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPA BPhA), 9,10-bis(1,1'-biphenyl-2-yl)-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracene-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracene-9-amine (abbreviation: DPhAPhA), coumarin 545T, N,N'-diphenylquinacridone (abbreviation: DPQd), rubren, 5,12-bis(1,1'-biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BPT), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6 -methyl-4H-pyran-4-ylidene)propanedinitrile (abbreviation: DCM1), 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinoridine-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluorantene-3,10-di Amine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinoridine-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinoridine-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTB), 2-(2,6-Bis{2-[4-(dimethylamino)phenyl]ethenyl}-4H-pyran-4-ylidene)propanedinitrile (abbreviation: BisDCM), 2-{2,6-Bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinoridine-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: BisDCJTM), N,N'-diphenyl-N,N'-(1,6-pyrene-diyl)bis[(6-phenylbenzo[b Examples include ]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03), 3,10-bis[N-(9-phenyl-9H-carbazole-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nbf(IV)-02), 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 1,6BnfAPrn-03, are preferred because they have high hole-trapping properties and excellent luminescence efficiency or reliability.

[0142] Also, 5,9-diphenyl-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene (abbreviation: DABNA1), 9-[(1,1'-biphenyl)-3-yl]-N,N,5,11-tetraphenyl-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene-3-amine (abbreviation: DABNA2), 2,12-di(tert-butyl)-5,9-di(4-tert-butylphenyl)-N,N-diphenyl-5H,9H-[1,4]benzazaborino[2,3,4-kl]phenaza Borin-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]phenazabolin-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]phenazabolin (abbreviation: Me-tBu4DABNA), N 7 ,N 7 ,N 13 ,N 13 Condensed heteroaromatic compounds containing nitrogen and boron, such as ,5,9,11,15-octaphenyl-5H,9H,11H,15H-[1,4]benzazabolino[2,3,4-kl][1,4]benzazabolino[4',3',2':4,5][1,4]benzazabolino[3,2-b]phenazabolin-7,13-diamine (abbreviation: ν-DABNA) and 2-(4-tert-butylphenyl)benz[5,6]indro[3,2,1-jk]benzo[b]carbazole (abbreviation: tBuPBibc), particularly compounds having a diaza-boranaphtho-anthracene skeleton, can be suitably used because they produce blue emission with a narrow emission spectrum and good color purity.

[0143] In addition to these, there is 9,10,11-tris[3,6-bis(1,1-dimethylethyl)-9H-carbazole-9-yl]-2,5,15,18-tetrakis(1,1-dimethylethyl)indoro[3,2,1-de]indoro[3',2',1':8,1][1,4]benzazavolino[2,3,4-kl]phenazavolin (abbreviation: BBCz-G), 9,11-Bis[3,6-Bis(1,1-dimethylethyl)-9H-carbazole-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-Y) can be suitably used.

[0144] When a phosphorescent material is used as the light-emitting material in the light-emitting layer 113, the following are some examples of materials that can be used.

[0145] Organometallic iridium with a 4H-triazole skeleton, such as Tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium(III) (abbreviation: [Ir(mpptz-dmp)3]) and Tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Mptz)3]). Complexes, organometallic iridium complexes having a 1H-triazole skeleton such as tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(Mptz1-mp)3]), tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Prptz1-Me)3]), fac-tris[1-( [2,6-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]), Tris(2-[1-{2,6-bis(1-methylethyl)phenyl}-1H-imidazole-2-yl-κN3] Organometallic iridium complexes having an imidazole skeleton such as -4-cyanophenyl-κC) (abbreviation: CNImIr), organometallic complexes having a benzimidazolidene skeleton such as tris[(6-tert-butyl-3-phenyl-2H-imidazo[4,5-b]pyrazine-1-yl-κC2)phenyl-κC]iridium(III) (abbreviation: [Ir(cb)3]), bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ Iridium(III) tetrakis(1-pyrazolyl) borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridinate-N,C 2’ Iridium(III) picolinate (abbreviation: Firpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinate-N,C 2’Iridium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyridinate-N,C 2’ Examples include organometallic iridium complexes that use phenylpyridine derivatives having electron-withdrawing groups, such as iridium(III) acetylacetonate (abbreviated as FIracac), as ligands. These compounds exhibit blue phosphorescence and have emission peaks in the wavelength range of 450 nm to 520 nm.

[0146] Also, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)3]), tris(4-t-butyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonato)bis(6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2(acac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]), (acetylacetonato)bis[5-methyl-6- Organometallic iridium complexes having a pyrimidine skeleton, such as (2-methylphenyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm)2(acac)]), (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)2(acac)]), organometallic iridium complexes having a pyrazine skeleton, such as (acetylacetonato)bis(3,5-dimethyl-2-phenylpyradinato)iridium(III) (abbreviation: [Ir(mppr-Me)2(acac)]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyradinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]), and tris(2-phenylpyrimidinato-N,C 2’Iridium(III) (abbreviation: [Ir(ppy)3]), bis(2-phenylpyridinate-N,C) 2’ Iridium(III) acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), bis(benzo[h]quinolinate)iridium(III) acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), tris(benzo[h]quinolinate)iridium(III) (abbreviation: [Ir(bzq)3]), tris(2-phenylquinolinate-N,C) 2’ Iridium(III) (abbreviation: [Ir(pq)3]), bis(2-phenylquinolinato-N,C) 2’) Iridium(III) acetylacetonate (abbreviation: [Ir(pq)2(acac)]), [2-d3-methyl-8-(2-pyridinyl-κN)benzoflof[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridinyl-κN2)phenyl-κC] Iridium(III) (abbreviation: [Ir(5mppy-d3)2(mbfpypy-d3)]), [2-d3 -methyl-(2-pyridinyl-κN)benzofloxacin[2,3-b]pyridinyl-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(ppy)2(mbfpypy-d3)]), [2-(4-d3-methyl-5-phenyl-2-pyridinyl-κN2)phenyl-κC]bis[2-(5-d3-methyl-2-pyridinyl-κN2)phenyl Examples include organometallic iridium complexes with a pyridine skeleton, such as [nyl-κC]iridium(III) (abbreviation: [Ir(5mppy-d3)2(mdppy-d3)]), [2-methyl-(2-pyridinyl-κN)benzofl[2,3-b]pyridine-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(ppy)2(mbfpypy)]), and [2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium (abbreviation: [Ir(ppy)2(mdppy)]), as well as rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [Tb(acac)3(Phen)]). These compounds primarily exhibit green phosphorescence and have emission peaks in the wavelength range of 500 nm to 600 nm. Organometallic iridium complexes with a pyrimidine skeleton are particularly preferred due to their outstanding reliability and luminescence efficiency.

[0147] Furthermore, organometallic iridium complexes having a pyrimidine skeleton, such as (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)]), and bis[4,6-di(naphthalene-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(d1npm)2(dpm)]), Organometallic iridium complexes with a pyrazine skeleton, such as (acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(tppr)2(dpm)]), and (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq)2(acac)]), and tris(1-phenylisoquinolinato-N,C) 2’ Iridium(III) (abbreviation: [Ir(piq)3]), bis(1-phenylisoquinolinato-N,C) 2’) Iridium(III) acetylacetonate (abbreviation: [Ir(piq)2(acac)]), (3,7-diethyl-4,6-nonanedionato-κO4,κO6)bis[2,4-dimethyl-6-[7-(1-methylethyl)-1-isoquinolinyl-κN]phenyl-κC]iridium(III), (3,7-diethyl-4,6-nonanedionato-κO4,κO6)bis[2,4-dimethyl-6-[5-(1-methylethyl)-2-quinolinyl-κN]phenyl-κC]iridium(III) are organometallic iridium compounds with a pyridine skeleton. In addition to dinium complexes, other examples include platinum complexes such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviated as PtOEP), and rare earth metal complexes such as tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviated as [Eu(DBM)3(Phen)]) and tris[1-(2-tenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviated as [Eu(TTA)3(Phen)]). These compounds exhibit red phosphorescence and have emission peaks in the wavelength range of 600 nm to 700 nm. Furthermore, organometallic iridium complexes with a pyrazine skeleton yield red emission with good chromaticity.

[0148] In addition to the phosphorescent compounds described above, other known phosphorescent compounds may be selected and used.

[0149] As TADF materials, fullerenes and their derivatives, acridines and their derivatives, eosin derivatives, etc., can be used. Also, metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd) can be used. Examples of metal-containing porphyrins include protoporphyrin-tin fluoride complexes (SnF2(Proto IX)), mesoporphyrin-tin fluoride complexes (SnF2(Meso IX)), hematoporphyrin-tin fluoride complexes (SnF2(Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complexes (SnF2(Copro III-4Me)), octaethylporphyrin-tin fluoride complexes (SnF2(OEP)), etioporphyrin-tin fluoride complexes (SnF2(Etio I)), and octaethylporphyrin-platinum chloride complexes (PtCl2OEP), as shown in the following structural formulas.

[0150] [ka]

[0151] Furthermore, the following structural formulas represent 2-(biphenyl-4-yl)-4,6-bis(12-phenylindoro[2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ), 9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazol (abbreviation: PCCzTzn), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 2-[4-(10H-phenoxazine-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn) Heterocyclic compounds having one or both of a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring can also be used, such as PXZ-TRZ, 3-[4-(5-phenyl-5,10-dihydrophenazine-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (abbreviated as PPZ-3TPT), 3-(9,9-dimethyl-9H-acridine-10-yl)-9H-xanthene-9-one (abbreviated as ACRXTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviated as DMAC-DPS), and 10-phenyl-10H,10'H-spiro[acridine-9,9'-anthracene]-10'-one (abbreviated as ACRSA). The heterocyclic compound is preferred because it has both a π-electron-excess heteroaromatic ring and a π-electron-deficient heteroaromatic ring, resulting in high electron transport and hole transport properties. Among the skeletons having a π-electron-deficient heteroaromatic ring, the pyridine skeleton, diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton), and triazine skeleton are preferred because they are stable and reliable. In particular, the benzoflopyrimidine skeleton, benzothienopyrimidine skeleton, benzoflopyrazine skeleton, and benzothienopyrazine skeleton are preferred because they have high acceptability and are reliable. Furthermore, among the skeletons having a π-electron-excess heteroaromatic ring, the acridine skeleton, phenoxazine skeleton, phenothiazine skeleton, furan skeleton, thiophene skeleton, and pyrrole skeleton are preferred because they are stable and reliable, and therefore it is preferable to have at least one of these skeletons.Furthermore, a dibenzofuran skeleton is preferred as the furan skeleton, and a dibenzothiophene skeleton is preferred as the thiophene skeleton. In addition, as the pyrrole skeleton, indole skeleton, carbazole skeleton, indrocarbazole skeleton, bicarbazole skeleton, and 3-(9-phenyl-9H-carbazole-3-yl)-9H-carbazole skeleton are particularly preferred. Substances in which a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring are directly bonded are particularly preferred because both the electron-donating and electron-accepting properties of the π-electron-rich heteroaromatic ring are strengthened, and the energy difference between the S1 and T1 levels is reduced, thus efficiently obtaining thermally activated delayed fluorescence. In addition, an aromatic ring to which an electron-withdrawing group such as a cyano group is bonded may be used instead of the π-electron-deficient heteroaromatic ring. Furthermore, aromatic amine skeletons, phenazine skeletons, etc., can be used as the π-electron-rich skeleton. Furthermore, as π-electron-deficient skeletons, xanthene skeletons, thioxanthene dioxide skeletons, oxadiazole skeletons, triazole skeletons, imidazole skeletons, anthraquinone skeletons, boron-containing skeletons such as phenylborane and volanthrene, aromatic rings having a nitrile group or a cyano group such as benzonitrile or cyanobenzene, heteroaromatic rings, carbonyl skeletons such as benzophenone, phosphine oxide skeletons, sulfone skeletons, etc., can be used. In this way, π-electron-deficient skeletons and π-electron-excess skeletons can be used instead of at least one of π-electron-deficient heteroaromatic rings and π-electron-excess heteroaromatic rings.

[0152] [ka]

[0153] TADF materials are materials that have a small difference between the S1 and T1 energy 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.

[0154] Furthermore, an excited complex (also called an exciplex) that forms an excited state with two types of substances has an extremely small difference between the S1 and T1 levels and functions as a TADF material that can convert triplet excitation energy into singlet excitation energy.

[0155] Furthermore, the phosphorescence spectrum observed at low temperatures (e.g., 77K to 10K) can be used as an indicator of the T1 level. For TADF materials, when a tangent is drawn at the short-wavelength tail of the fluorescence spectrum and the energy at the wavelength of the extrapolation is taken as the S1 level, and when a tangent is drawn at the short-wavelength tail of the phosphorescence spectrum and the energy at the wavelength of the extrapolation is taken as the T1 level, it is preferable that the difference between S1 and T1 is 0.3 eV or less, and more preferably 0.2 eV or less.

[0156] 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.

[0157] As the host material for the light-emitting layer, various carrier transport materials such as electron transport materials and / or hole transport materials, or the TADF material mentioned above, can be used.

[0158] Preferred materials for hole transport 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.

[0159] Such hole-transporting materials more preferably have one of the following skeletons: carbazole, dibenzofuran, dibenzothiophene, or anthracene. 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 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.

[0160] Examples of materials possessing such hole transport properties 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), and 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylami (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine ( Aromatic compounds such as PCBANB (abbreviated as PCBA), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCBNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]fluoren-2-amine (abbreviated as PCBAF), and N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9'-spirobio[9H-fluoren]-2-amine (abbreviated as PCBASF) Compounds having a fragrance amine skeleton, compounds having a carbazole skeleton such as 1,3-bis(N-carbazolyl)benzene (abbreviated as mCP), 4,4'-di(N-carbazolyl)biphenyl (abbreviated as CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviated as CzTP), 3,3'-bis(9-phenyl-9H-carbazole) (abbreviated as PCCP), 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviated as 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 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.

[0161] For materials exhibiting electron transport properties, the electron mobility at which the square root of the electric field strength [V / cm] is 600 is 1 × 10⁻⁶. -7 cm 2 / Vs or more, preferably 1 × 10 -6 cm 2 A material having an electron mobility of / Vs or higher is preferred. However, any material with higher electron transport capabilities than holes can be used.

[0162] Preferred materials with electron transport properties include metal complexes such as bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviated as BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviated as BAlq), bis(8-quinolinolato)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazollyl)phenolato]zinc(II) (abbreviated as ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviated as ZnBTZ), as well as organic compounds having a π-electron-deficient heteroaromatic ring skeleton. Examples of organic compounds having a π-electron-deficient heteroaromatic ring skeleton include organic compounds containing a heteroaromatic ring having a polyazole 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.

[0163] 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.

[0164] Examples of organic compounds having a π-electron-deficient heteroaromatic ring skeleton include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviated as TAZ), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as OXD-7), and 9-[4-(5-phenyl-1,3,4-oxadiazole- Organic compounds having an azole skeleton, such as 2-yl)phenyl]-9H-carbazole (abbreviation: CO11), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), 4,4'-bis(5-methylbenzoxazole-2-yl)stilbene (abbreviation: BzOS), and 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 Organic compounds containing heteroaromatic rings with a pyridine skeleton, such as -phenanthroline (abbreviation: mTpPPhen), 2-phenyl-9-(2-triphenylenyl)-1,10-phenanthroline (abbreviation: Ph-TpPhen), 2-[4-(9-phenantrenyl)-1-naphthalenyl]-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-(3'-dibenzothiophen-4-yl)biphenyl]dibenzo[f,h]Quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]Quinoxaline (abbreviation: 2mCzBPDBq), 2-[4'-(9-phenyl-9H-carbazol-3-yl)-3,1'-biphenyl-1-yl]dibenzo[f,h]Quinoxaline (abbreviation: 2mpPCBPDBq), 2-[4-(3,6-diphenyl-9H- Carbazole-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPDBq-II), 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II), 9-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]flo[2,3-b]pyrazine (abbreviation: 9mDBtBPNfpr), 9-[3'- [(dibenzothiophen-4-yl)biphenyl-4-yl]naphtho[1',2':4,5]flo[2,3-b]pyrazine (abbreviation: 9pmDBtBPNfpr), 4,6-bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl)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-(1,1'-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)(1,1'-biphenyl-3-yl)]naphtho[1',2':4,5]flo[3,2-d]pyrimidine (abbreviation: 8mDBtBPNfpm), 8-[(2,2'-binaphthalene)-6-yl]-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzoflo[3,2-d]pyrimidine (abbreviation: 8(βN2)-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-(1,1'-biphenyl-3-yl)-4-[3,5-bis(9H-carbazole-9-yl)phenyl]-2-phenylpyrimidine (abbreviation: 6mBP-4Cz2PPm), 2,6-bis(4-naphthalene-1-ylphenyl)-4-[4-(3-pyridyl)phenyl]pyrimidine (abbreviation: 2,4NP-6PyPPm), 4-[3,5-bis(9H-carbazole-9-yl)phenyl Organic compounds having a diazine skeleton such as ]-2-phenyl-6-(1,1'-biphenyl-4-yl)pyrimidine (abbreviation: 6BP-4Cz2PPm), 7-[4-(9-phenyl-9H-carbazole-2-yl)quinazolin-2-yl]-7H-dibenzo[c,g]carbazole (abbreviation: PC-cgDBCzQz), 2-[(1,1'-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-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 9-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn-02), 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)-1,1'-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazin (abbreviation: mFBPTzn), 5-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-7,7-dimethyl-5 H,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'-(pyridine-3-yl)biphenyl-3-yl)-1,3,5-triazine (abbreviation: TmPPPyTz), 2-[3-(2,6-dimethyl-3-pyridinyl [Lu)-5-(9-phenantrenyl)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-phenyl-indoro[2,3-a]carbazole (abbreviation: BP-Icz(II)Tzn), 2-[3'-(triphenylene-2-yl)-1,1'-biphenyl [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-[1,1'-biphenyl]-3-yl-4-phenyl-6-(8-[1,1':4',1''-terphenyl]-4-yl-1-dibenzofuranyl)-1,3,Organic compounds containing a heteroaromatic ring having a triazine skeleton such as 5-triazine (abbreviation: mBP-TPDBfTzn) can be mentioned. Further, an organic compound containing a heteroaromatic ring having a diazine skeleton or an organic compound containing a heteroaromatic ring having a pyridine skeleton, and an organic compound containing a heteroaromatic ring having a triazine skeleton are preferable because of their good reliability. In particular, an organic compound containing a heteroaromatic ring having a diazine (pyrimidine or pyrazine) skeleton and an organic compound containing a heteroaromatic ring having a triazine skeleton have high electron transport properties and contribute to reducing the driving voltage.,

[0165] As the TADF material that can be used as the host material, those mentioned above as the TADF material can be used in the same manner. When the TADF material is used as the host material, the triplet excitation energy generated in the TADF material is converted into singlet excitation energy by reverse intersystem crossing, and further energy transfer to the light-emitting substance can increase the luminous efficiency of the light-emitting device. At this time, the TADF material functions as an energy donor, and the light-emitting substance functions as an energy acceptor.

[0166] This is very effective when the above light-emitting substance is a fluorescent light-emitting substance. Also, at this time, in order to obtain high luminous efficiency, it is preferable that the S1 level of the TADF material is higher than the S1 level of the fluorescent light-emitting substance. Also, it is preferable that the T1 level of the TADF material is higher than the S1 level of the fluorescent light-emitting substance. Therefore, it is preferable that the T1 level of the TADF material is higher than the T1 level of the fluorescent light-emitting substance.

[0167] Also, it is preferable to use a TADF material that exhibits light emission overlapping with the wavelength of the absorption band on the lowest energy side of the fluorescent light-emitting substance. By doing so, the transfer of excitation energy from the TADF material to the fluorescent light-emitting substance becomes smooth, and light emission can be obtained efficiently, which is preferable.

[0168] Furthermore, for singlet excitation energy to be efficiently generated from triplet excitation energy by reverse intersystem crossing, it is preferable that carrier recombination occurs in the TADF material. It is also preferable that the triplet excitation energy generated in the TADF material does not transfer to the triplet excitation energy of the fluorescent material. To achieve this, it is preferable that the fluorescent material has protecting groups around the luminescent phosphoform (the skeleton that causes luminescence). Preferred protecting groups are substituents without π bonds, and saturated hydrocarbons are preferred. Specifically, examples include alkyl groups having 3 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 carbon atoms, and trialkylsilyl groups having 3 to 10 carbon atoms. It is even preferable to have multiple protecting groups. Substituents without π bonds have poor carrier transport function, and therefore can increase the distance between the TADF material and the luminescent phosphoform of the fluorescent material with little effect on carrier transport or carrier recombination. Here, the luminescent phosphoform refers to the atomic group (skeleton) that causes luminescence in the fluorescent material. The luminescent phosphodiosity 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 condensed aromatic rings or condensed heteroaromatic rings include phenanthrene skeletons, stilbene skeletons, acridone skeletons, phenoxazine skeletons, and phenothiazine skeletons. Fluorescent materials having naphthalene, anthracene, fluorene, chrysene, triphenylene, tetracene, pyrene, perylene, coumarin, quinacridone, or naphthobisbenzofuran skeletons are particularly preferred due to their high fluorescence quantum yield.

[0169] When using a fluorescent material as the light-emitting material, a material having 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, materials having a diphenylanthracene skeleton, and especially a 9,10-diphenylanthracene skeleton, are preferred because they are 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 carbazole, is even more preferred because the HOMO is about 0.1 eV shallower than carbazole, making it easier for holes to enter. In particular, a dibenzocarbazole skeleton is preferred as the HOMO is about 0.1 eV shallower than carbazole, making it easier for holes to enter, and it also has excellent hole transport properties and high heat resistance. Therefore, a more preferable host material is a substance having both a 9,10-diphenylanthracene skeleton and a carbazole skeleton (or a benzocarbazole skeleton or dibenzocarbazole skeleton). Furthermore, from the viewpoint of hole injection and transport properties, a benzofluorene skeleton or a dibenzofluorene skeleton may be used instead of the carbazole skeleton.Examples of such substances include 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviated as PCzPA), 3-[4-(1-naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviated as PCPN), 9-[4-(10-phenyl-9-antracenyl)phenyl]-9H-carbazole (abbreviated as CzPA), 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated as cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl]benzo[b]naphtho[1,2-d]furan (abbreviated as 2mBnfPPA), and 9-phenyl-10-[4-(9-phenyl-9H-fluoren-9-yl)biphenyl-4'-yl] Anthracene (abbreviation: FLPPA), 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth), 9-(1-naphthyl)-10-(2-naphthyl)anthracene (abbreviation: α,βADN), 2-(10-phenylanthracene-9-yl)dibenzofuran, 2-(10-phenyl-9-anthracenyl)benzo[b] Examples include naphtho[2,3-d]furan (abbreviated as Bnf(II)PhA), 9-(2-naphthyl)-10-[3-(2-naphthyl)phenyl]anthracene (abbreviated as βN-mβNPAnth), and 1-[4-(10-[1,1'-biphenyl]-4-yl-9-anthracenyl)phenyl]-2-ethyl-1H-benzimidazole (abbreviated as EtBImPBPhA). In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA exhibit very good properties and are therefore preferred choices.

[0170] 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.

[0171] 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.

[0172] 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.

[0173] Furthermore, at least one of the materials forming the excitation complex may be a phosphorescent material. By doing so, the triplet excitation energy can be efficiently converted to singlet excitation energy through reverse intersystem crossing.

[0174] 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).

[0175] The formation of excited complexes can be confirmed, for example, by comparing the emission spectra of a hole-transporting material, an electron-transporting material, and a mixed film made by mixing these materials, and observing that the emission spectrum of the mixed film shifts to a longer wavelength than the emission spectra of each individual material (or has a new peak on the longer wavelength side). Alternatively, it can be confirmed by comparing the transient photoluminescence (PL) of a hole-transporting material, the transient PL of an electron-transporting material, and the transient PL of a mixed film made by mixing these materials, and observing differences in the transient response, such as the transient PL lifetime of the mixed film having a longer lifetime component or a larger proportion of the delayed component than the transient PL lifetime of each individual material. Furthermore, the transient PL mentioned above can be replaced with transient electroluminescence (EL). That is, the formation of excited complexes can also be confirmed by comparing the transient EL of a hole-transporting material, the transient EL of an electron-transporting material, and the transient EL of a mixed film made by mixing these materials, and observing the differences in the transient response.

[0176] The electron transport layer 114 is a layer containing an electron-transporting material. The electron-transporting material has an electron mobility of 1 × 10⁻¹⁰ at an electric field strength [V / cm] square root of 600. -7 cm 2 / Vs or more, preferably 1 × 10 -6 cm 2 A material having an electron mobility of / Vs or higher is preferred. However, any material that has higher electron transport properties than hole transport properties can be used. As the material having the above electron transport properties, 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 a polyazole 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.

[0177] As electron-transporting materials that can be used in the electron transport layer 114, the same materials listed as electron-transporting materials for the light-emitting layer 113 can be used. Among these, organic compounds containing heteroaromatic rings having a diazine 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. Among these, 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. In addition, organic compounds represented by general formulas (G1) to (G4) shown in Embodiment 1 can also be used.

[0178] The electron transport layer 114 may have a multilayer structure. Furthermore, the layer in contact with the light-emitting layer 113 in the multilayer electron transport layer 114 may function as a hole-blocking layer. When the electron transport layer in contact with the light-emitting layer functions as a hole-blocking layer, it is preferable to use a material whose HOMO level is 0.5 eV or more deeper than the HOMO level of the material contained in the light-emitting layer 113.

[0179] The electron injection layer 115 preferably contains an organic compound represented by general formula (G1) to general formula (G4) as shown in Embodiment 1.

[0180] The organic compound represented by any of the above general formulas (G1) to (G4) has lower solubility in water than hpp2Py mentioned earlier, making it more resistant to exposure to air and aqueous solutions during photolithography and enabling the provision of light-emitting devices with good properties.

[0181] A light-emitting device using an organic compound according to one aspect of the present invention can provide a light-emitting device with better initial characteristics and reliability than a light-emitting device using hpp2Py. Furthermore, hpp2Py and the organic compound according to one aspect of the present invention, represented by any of the above general formulas (G1) to (G4), are less likely to cause metal contamination of the manufacturing line than alkali metals or alkaline earth metals, or compounds thereof, and are easily vapor-deposited. Therefore, they are more suitably used in light-emitting devices manufactured using a photolithography process. Of course, their use in light-emitting devices that do not use a photolithography process is also effective.

[0182] Furthermore, the organic compound according to one embodiment of the present invention, represented by any of the above general formulas (G1) to (G4), has a relatively high glass transition temperature, with a value of 70°C or higher, making it possible to provide a highly heat-resistant light-emitting device. It can also withstand the heating process in the photolithography process, making it possible to provide a high-definition light-emitting device with excellent properties.

[0183] Furthermore, the electron injection layer 115 may include a compound or complex of an alkali metal or alkaline earth metal such as 8-hydroxyquinolinatolithium (abbreviated as Liq), or a layer containing 1,1'-pyridine-2,6-diylbis(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine) (abbreviated as hpp2Py).

[0184] The electron injection layer 115 may be made by using the above-mentioned materials alone, or by incorporating them into a layer made of materials having electron transport properties.

[0185] Alternatively, a charge generation layer 116 may be provided instead of the electron injection layer 115 (Figure 1(B)). The charge generation layer 116 is a layer that can inject holes into the layer in contact with the cathode side and electrons into the layer in contact with the anode side by applying a potential. The charge generation layer 116 includes at least a P-type layer 117. The P-type layer 117 is preferably formed using a composite material listed above as a material that can constitute the hole injection layer 111. The P-type layer 117 may also be formed by laminating a film containing the acceptor material and a film containing the hole transport material as materials that constitute 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.

[0186] Furthermore, it is preferable that the charge generation layer 116 includes, in addition to the P-type layer 117, one or both of the electronic relay layer 118 and the N-type layer 119.

[0187] The electron relay layer 118 contains at least an electron-transporting material and has the function of preventing interaction between the N-type layer 119 and the P-type layer 117, thereby smoothly transferring electrons. The LUMO level of the electron-transporting material contained in the electron relay layer 118 is preferably 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, more preferably -5.0 eV or higher and -3.0 eV or lower. 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.

[0188] For the N-type layer 119, it is possible to use substances with high electron injection properties such as alkali metals, alkaline earth metals, rare earth metals, and their compounds (alkali metal compounds (including oxides such as lithium oxide, halides, carbonates such as lithium carbonate and cesium carbonate), alkaline earth metal compounds (including oxides, halides, carbonates), or rare earth metal compounds (including oxides, halides, carbonates)). In addition, for the N-type layer 119, it is preferable to use an organic compound represented by any one of the general formulas (G1) to (G4) in Embodiment 1.

[0189] Also, when the N-type layer 119 is formed by including a substance having electron transporting properties and a donor substance, as the donor substance, in addition to alkali metals, alkaline earth metals, rare earth metals, and their compounds (alkali metal compounds (including oxides such as lithium oxide, halides, carbonates such as lithium carbonate and cesium carbonate), alkaline earth metal compounds (including oxides, halides, carbonates), or rare earth metal compounds (including oxides, halides, carbonates)), organic compounds such as tetrathianaphthacene (abbreviation: TTN), nickelocene, decamethylnickelocene, and organic compounds represented by any one of the general formulas (G1) to (G4) in Embodiment 1 can also be used. Note that, as the substance having electron transporting properties, it can be formed using the same materials as those constituting the electron transport layer 114 described above.

[0190] The second electrode 102 is an electrode that includes a cathode. The second electrode 102 may have a layered structure, in which case the layer in contact with the organic compound layer 103 functions as the cathode. As the material forming the cathode, metals, alloys, electrically conductive compounds, and mixtures thereof with a small work function (specifically 3.8 eV or less) can be used. Specific examples of such cathode materials include alkali metals such as lithium (Li) or cesium (Cs), elements belonging to group 1 or 2 of the periodic table such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys (MgAg, AlLi) and compounds (lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), etc.) containing these, rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these. However, by providing an electron injection layer 115 or a thin film of a material with a low work function between the second electrode 102 and the electron transport layer, various conductive materials such as Al, Ag, ITO, silicon, or indium oxide-tin oxide containing silicon oxide can be used as the cathode, regardless of the magnitude of the work function.

[0191] 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.

[0192] These conductive materials can be formed using dry methods such as vacuum deposition or sputtering, inkjet printing, or spin coating. Alternatively, they may be formed using a wet method with a sol-gel process, or using a metal paste.

[0193] 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.

[0194] Furthermore, each electrode or layer described above may be formed using different film deposition methods.

[0195] Next, an embodiment of a light-emitting device (also called a stacked device or tandem device) with a configuration in which multiple light-emitting units are stacked will be described with reference to Figure 1(C). This light-emitting device has multiple light-emitting units between the anode and the cathode. Each light-emitting unit has a configuration almost identical to the organic compound layer 103 shown in Figure 1(A). In other words, the light-emitting device shown in Figure 1(C) is a light-emitting device having multiple light-emitting units, while the light-emitting devices shown in Figures 1(A) and 1(B) are light-emitting devices having one light-emitting unit.

[0196] In Figure 1(C), a first light-emitting unit 511 and a second light-emitting unit 512 are stacked between the first electrode 501 and the second electrode 502, and an intermediate layer 513 is provided between the first 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 1(A), respectively, and the same components described in the explanation of Figure 1(A) can be applied. Furthermore, the first light-emitting unit 511 and the second light-emitting unit 512 may have the same configuration or different configurations.

[0197] The intermediate layer 513 has the function of injecting electrons into one light-emitting unit and holes into the other light-emitting unit when a voltage is applied to the first electrode 501 and the second electrode 502. That is, in Figure 1(C), when a voltage is applied such that the potential of the anode is higher than the potential of the cathode, the intermediate layer 513 should inject electrons into the first light-emitting unit 511 and holes into the second light-emitting unit 512.

[0198] The intermediate layer 513 is preferably formed with the same configuration as the charge generation layer 116 described in Figure 1(B). The composite material of organic compound and metal oxide used in the P-type layer has excellent carrier implantation and carrier transport properties, enabling low-voltage and low-current operation. If the anode side of the light-emitting unit is in contact with the intermediate layer 513, the intermediate layer 513 can also act as a hole injection layer for the light-emitting unit, so the light-emitting unit does not need to have a hole injection layer.

[0199] Furthermore, it is preferable to provide an N-type layer 119 in the intermediate layer 513. In this case, it is even more preferable that the N-type layer 119 contains an organic compound represented by any of the general formulas (G1) to (G4) described in Embodiment 1.

[0200] The organic compounds represented by any of the above general formulas (G1) to (G4) have lower solubility in water than the hpp2Py mentioned earlier, making them more resistant to exposure to air and aqueous solutions during photolithography and enabling the provision of light-emitting devices with good properties.

[0201] Furthermore, light-emitting devices using the organic compound represented by any of the above general formulas (G1) to (G4) can provide light-emitting devices with better initial characteristics and reliability than those using hpp2Py. It should be noted that hpp2Py and the organic compound according to one embodiment of the present invention, represented by any of the above general formulas (G1) to (G4), are less likely to cause metal contamination of the manufacturing line than alkali metals or alkaline earth metals, or compounds thereof, and are easily vapor-deposited, making them more suitable for use in light-emitting devices manufactured using a photolithography process. Of course, they are also suitable for light-emitting devices manufactured using processes that do not employ photolithography.

[0202] Furthermore, the organic compound according to one embodiment of the present invention, represented by any of the above general formulas (G1) to (G4), has a relatively high glass transition temperature, having a value of 70°C or higher, making it possible to provide a highly heat-resistant light-emitting device. It can also withstand heating processes, particularly heating processes in photolithography, making it possible to provide a high-definition light-emitting device with excellent properties.

[0203] Furthermore, if an N-type layer 119 is formed in the intermediate layer, the N-type layer 119 will play 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 (in this case, the first light-emitting unit 511).

[0204] Figure 1(C) illustrates a light-emitting device having two light-emitting units, but the same principles can be applied to light-emitting devices with three or more stacked light-emitting units. As in the light-emitting device according to this embodiment, by arranging multiple light-emitting units separated between a pair of electrodes by an intermediate layer 513, high-brightness light emission can be achieved while maintaining a low current density, and a longer-life element can be realized. Furthermore, a light-emitting device that can be driven at a low voltage and consumes little power can be realized.

[0205] Furthermore, by making the light-emitting colors of each light-emitting unit different, it is possible to obtain a desired color of light 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 light-emitting colors from the first light-emitting unit and blue light-emitting color from the second light-emitting unit.

[0206] Furthermore, each layer, such as the organic compound layer 103, the first light-emitting unit 511, the second light-emitting unit 512, and the intermediate 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.

[0207] Figure 2(A) shows two adjacent light-emitting devices (light-emitting device 130a, light-emitting device 130b) included in a display device according to one embodiment of the present invention.

[0208] The light-emitting device 130a has an organic compound layer 103a between a first electrode 101a on an insulating layer 175 and an opposing second electrode 102. The organic compound layer 103a is shown to have a hole injection layer 111a, a hole transport layer 112a, a light-emitting layer 113a, an electron transport layer 114a, and an electron injection layer 115, but it may be a layer having a different laminated structure.

[0209] The light-emitting device 130b has an organic compound layer 103b between the first electrode 101b on the insulating layer 175 and the opposing second electrode 102. The organic compound layer 103b is shown to have a hole injection layer 111b, a hole transport layer 112b, a light-emitting layer 113b, an electron transport layer 114b, and an electron injection layer 115, but it may be a layer having a different laminated structure.

[0210] Furthermore, it is preferable that the electron injection layer 115 and the second electrode 102 are a continuous, shared layer in the light-emitting devices 130a and 130b. In addition, the organic compound layers 103a and 103b other than the electron injection layer 115 are processed by photolithography after the layer that will become the electron transport layer 114a and after the layer that will become the electron transport layer 114b are formed, and are therefore independent of each other. Furthermore, the edges (contours) of the organic compound layers 103a other than the electron injection layer 115 are processed by photolithography and therefore roughly coincide with the substrate in the direction perpendicular to it. Similarly, the edges (contours) of the organic compound layers 103b other than the electron injection layer 115 are processed by photolithography and therefore roughly coincide with the substrate in the direction perpendicular to it. Furthermore, it is preferable that the organic compound represented by any of the general formulas (G1) to (G4) described in Embodiment 1 is contained in the layer on the cathode side from the light-emitting layer, and more preferably contained in the electron injection layer 115.

[0211] Furthermore, because the organic compound layer is processed by photolithography, a gap d exists between the organic compound layer 103a and the organic compound layer 103b. In addition, the distance between the first electrode 101a and the first electrode 101b can be made smaller than when mask deposition is performed because the organic compound layer is processed by photolithography, and can be set to 2 μm or more and 5 μm or less.

[0212] Figure 2(B) shows two adjacent tandem light-emitting devices (light-emitting device 130c, light-emitting device 130d) included in a display device according to one embodiment of the present invention.

[0213] The light-emitting device 130c has an organic compound layer 103c between the first electrode 101c and the second electrode 102 on an insulating layer 175. The organic compound layer 103c has a configuration in which a first light-emitting unit 501c and a second light-emitting unit 502c are stacked with an intermediate layer 116c in between. Although Figure 2(B) shows an example in which two light-emitting units are stacked, a configuration in which three or more light-emitting units are stacked is also possible. The first light-emitting unit 501c has a hole injection layer 111c, a first hole transport layer 112c_1, a first light-emitting layer 113c_1, and a first electron transport layer 114c_1. The intermediate layer 116c has a P-type layer 117c, an electron relay layer 118c, and an N-type layer 119c. The electron relay layer 118c may or may not be present. The second light-emitting unit 502c has a second hole transport layer 112c_2, a second light-emitting layer 113c_2, a second electron transport layer 114c_2, and an electron injection layer 115.

[0214] The light-emitting device 130d has an organic compound layer 103d between the first electrode 101d and the second electrode 102 on an insulating layer 175. The organic compound layer 103d has a configuration in which the first light-emitting unit 501d and the second light-emitting unit 502d are stacked with an intermediate layer 116d in between. Although Figure 2(B) shows an example in which two light-emitting units are stacked, a configuration in which three or more light-emitting units are stacked is also possible. The first light-emitting unit 501d has a hole injection layer 111d, a first hole transport layer 112d_1, a first light-emitting layer 113d_1, and a first electron transport layer 114d_1. The intermediate layer 116d has a P-type layer 117d, an electron relay layer 118d, and an N-type layer 119d. The electron relay layer 118d may or may not be present. The second light-emitting unit 502d includes a second hole transport layer 112d_2, a second light-emitting layer 113d_2, a second electron transport layer 114d_2, and an electron injection layer 115.

[0215] The organic compound represented by any of the general formulas (G1) to (G4) described in Embodiment 1 is preferably contained in the electron carrier region layer, and more preferably in the electron injection layer 115 or the N-type layer 119c, N-type layer 119d. It is particularly preferable that it be contained in the N-type layer 119c and N-type layer 119d.

[0216] When a light-emitting device processed using photolithography is a tandem type light-emitting device, using alkali metals or alkaline earth metals, or compounds thereof, in the N-type layer may cause metal contamination of the equipment or line during processing. However, such contamination does not occur when using an organic compound represented by any of the general formulas (G1) to (G4). Furthermore, since the organic compounds represented by any of the general formulas (G1) to (G4) have lower water solubility than hpp2Py, they are less affected by atmospheric components. Therefore, by using them in the N-type layer of the intermediate layer, it is possible to provide a light-emitting device with superior initial characteristics and reliability compared to when hpp2Py is used. In addition, since the organic compounds represented by any of the general formulas (G1) to (G4) have better heat resistance (higher Tg) than hpp2Py, by using them in the N-type layer of the intermediate layer, it is possible to provide a light-emitting device with higher heat resistance and reliability compared to when hpp2Py is used.

[0217] Furthermore, it is preferable that the electron injection layer 115 and the second electrode 102 are a continuous, shared layer in the light-emitting devices 130c and 130d. In addition, the organic compound layers 103c and 103d other than the electron injection layer 115 are processed by photolithography after the formation of the layer that will become the second electron transport layer 114c_2 and after the formation of the layer that will become the second electron transport layer 114d_2, respectively, and are therefore independent of each other. Furthermore, the edges (contours) of the organic compound layers 103c other than the electron injection layer 115 are processed by photolithography and therefore roughly coincide with the substrate in the direction perpendicular to it. Similarly, the edges (contours) of the organic compound layers 103d other than the electron injection layer 115 are processed by photolithography and therefore roughly coincide with the substrate in the direction perpendicular to it.

[0218] Furthermore, because the organic compound layer is processed by photolithography, a gap d exists between the organic compound layer 103c and the organic compound layer 103d. In addition, the distance between the first electrode 101c and the first electrode 101d can be made smaller than when mask deposition is performed because the organic compound layer is processed by photolithography, and can be set to 2 μm to 5 μm.

[0219] (Embodiment 3) This embodiment describes a configuration in which a light-emitting device according to one aspect of the present invention is used as a display element for a display device.

[0220] As illustrated in Figures 3(A) and 3(B), multiple light-emitting devices 130 are formed on the insulating layer 175 to constitute a display device.

[0221] The display device 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.

[0222] In this specification, for example, when describing matters common to sub-pixels 110R, 110G, and 110B, they may be referred to simply as sub-pixel 110. Similarly, when describing matters common to other components distinguished by letters, the letters may be omitted and the corresponding symbols used.

[0223] Sub-pixel 110R emits red light, sub-pixel 110G emits green light, and sub-pixel 110B emits blue light. This allows an image to be displayed on the pixel section 177. In this embodiment, three sub-pixels of red (R), green (G), and blue (B) are used as an example, but other combinations of sub-pixels of other colors may be used. Furthermore, the number of sub-pixels is not limited to three, but may be four or more. Examples of four sub-pixels include four sub-pixels of R, G, B, and white (W), four sub-pixels of R, G, B, and Y, and four sub-pixels of R, G, B, and infrared (IR).

[0224] In this specification and other documents, the row direction is sometimes referred to as the X direction, and the column direction as the Y direction. The X and Y directions intersect, for example, perpendicularly.

[0225] Figure 3(A) shows an example where subpixels of different colors are arranged in the X direction, and subpixels of the same color are arranged in the Y direction. Alternatively, subpixels of different colors may be arranged in the Y direction, and subpixels of the same color may be arranged in the X direction.

[0226] A connecting portion 140 and a region 141 may be provided on the outside of the pixel portion 177. The region 141 is provided between the pixel portion 177 and the connecting portion 140. An organic compound layer 103 is provided in the region 141. A conductive layer 151C is provided in the connecting portion 140.

[0227] Figure 3(A) shows an example where region 141 and connection portion 140 are located to the right of the pixel portion 177, but the positions of region 141 and connection portion 140 are not particularly limited. Also, region 141 and connection portion 140 may be singular or plural.

[0228] Figure 3(B) is an example of a cross-sectional view between the dashed line A1-A2 in Figure 3(A). As shown in Figure 3(B), the display device 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.

[0229] 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.

[0230] In Figure 3(B), multiple cross-sections of the inorganic insulating layer 125 and the insulating layer 127 are shown, but when the display device is viewed from above, it is preferable that the inorganic insulating layer 125 and the insulating layer 127 are connected as one unit. In other words, it is preferable that the insulating layer 127 is an insulating layer having an opening on the first electrode.

[0231] Figure 3(B) shows light-emitting devices 130R, 130G, and 130B as light-emitting devices 130. Light-emitting devices 130R, 130G, and 130B emit light of different colors. 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.

[0232] 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.

[0233] The light-emitting device 130R has the configuration shown in Embodiment 2. It includes a first electrode (pixel electrode) consisting of a conductive layer 151R and a conductive layer 152R, a first layer 104R on the first electrode, an organic compound layer (second layer 105 on the first layer 104R), and a second electrode (common electrode) 102 on the second layer 105. The second layer 105 is preferably located on the second electrode (common electrode) side of the light-emitting layer, and is preferably a hole blocking layer, an electron transport layer, or an electron injection layer. With this configuration, damage to the light-emitting layer or active layer during the photolithography process can be suppressed, and good film quality and electrical properties can be expected. In addition, there may be several layers, such as electron injection layers, as common layers in contact with the second electrode (common electrode).

[0234] The light-emitting device 130G has the configuration shown in Embodiment 2. It includes a first electrode (pixel electrode) consisting of a conductive layer 151G and a conductive layer 152G, a first layer 104G on the first electrode, a second layer 105 on the first layer 104G, and a second electrode (common electrode) 102 on the second layer 105. The second layer 105 is preferably an electron injection layer.

[0235] The light-emitting device 130B has the configuration shown in Embodiment 2. It includes a first electrode (pixel electrode) consisting of a conductive layer 151B and a conductive layer 152B, a first layer 104B on the first electrode, a second layer 105 on the first layer 104B, and a second electrode (common electrode) 102 on the second layer 105. The second layer 105 is preferably an electron injection layer.

[0236] Of the pixel electrodes (first electrodes) and common electrodes (second electrodes) of the light-emitting device, one functions as the anode and the other as the cathode. In this embodiment, unless otherwise specified, the pixel electrodes function as the anode and the common electrodes function as the cathode.

[0237] The first layers 104R, 104G, and 104B are independent island-like structures, each or each corresponding to a specific light-emitting color. Preferably, the first layers 104R, 104G, and 104B do not overlap with each other. By providing the first layer 104 in an island-like structure 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 levels.

[0238] The island-shaped first layer 104 is formed by depositing an EL film and processing the EL using photolithography.

[0239] Preferably, the first layer 104 is provided so as to cover the top and side surfaces of the first electrode (pixel electrode) of the light-emitting device 130. This makes it easier to increase the aperture ratio of the display device compared to a configuration in which the edges of the first layer 104 are located inward from the edges of the pixel electrode. In addition, by covering the side surfaces of the pixel electrode of the light-emitting device 130 with the first layer 104, contact between the pixel electrode and the second electrode 102 can be suppressed, thereby suppressing short circuits of the light-emitting device 130.

[0240] Furthermore, in a display device according to one aspect of the present invention, it is preferable that the first electrode (pixel electrode) of the light-emitting device be in a stacked configuration. For example, in the example shown in Figure 3(B), the first electrode of the light-emitting device 130 is in a stacked configuration of a conductive layer 151 provided on the insulating layer 171 side and a conductive layer 152 provided on the organic compound layer side.

[0241] 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.

[0242] 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.

[0243] 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.

[0244] Furthermore, it is preferable that the end of the conductive layer 151 has a tapered shape. Specifically, it is preferable that the end 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 end of the conductive layer 152 tapered, the coverage of the first layer 104 provided along the side surface of the conductive layer 152 can be improved.

[0245] In one embodiment of the present invention, the light-emitting device 130 has the configuration shown in Embodiment 2, making it possible to provide a highly reliable display device.

[0246] Next, an example of a method for manufacturing a display device having the configuration shown in Figure 3(A) will be explained using Figures 4 to 9.

[0247] [Example of manufacturing method] Thin films (insulating films, semiconductor films, conductive films, etc.) that constitute a display device can be formed using methods such as sputtering, chemical vapor deposition (CVD), vacuum deposition, pulsed laser deposition (PLD), or atomic layer deposition (ALD).

[0248] 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.

[0249] Furthermore, when processing the thin films that make up the display device, the processing can be done using methods such as photolithography.

[0250] 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.

[0251] For etching thin films, dry etching, wet etching, or sandblasting methods can be used.

[0252] First, as shown in Figure 4(A), an insulating layer 171 is formed on a substrate (not shown). Next, a conductive layer 172 and a conductive layer 179 are formed on the insulating layer 171, and an insulating layer 173 is formed on the insulating layer 171 so as to cover the conductive layers 172 and 179. Next, an insulating layer 174 is formed on the insulating layer 173, and an insulating layer 175 is formed on the insulating layer 174.

[0253] As the substrate, a substrate with at least sufficient heat resistance to withstand subsequent heat treatment can be used. For example, glass substrates, quartz substrates, sapphire substrates, ceramic substrates, or organic resin substrates, single-crystal semiconductor substrates made of silicon or silicon carbide, polycrystalline semiconductor substrates, compound semiconductor substrates such as silicon germanium, and SOI substrates can be used.

[0254] Next, as shown in Figure 4(A), openings reaching the conductive layer 172 are formed in the insulating layer 175, insulating layer 174, and insulating layer 173. Subsequently, a plug 176 is formed to fill these openings.

[0255] Next, as shown in Figure 4(A), a conductive film 151f, which will later become conductive layers 151R, 151G, 151B, and 151C, is formed on the plug 176 and the insulating layer 175. For example, a metallic material can be used as the conductive film 151f.

[0256] Next, as shown in Figure 4(A), a resist mask 191 is formed on the conductive film 151f. The resist mask 191 can be formed by applying a photosensitive material (photoresist), exposing it to light, and developing it.

[0257] Next, as shown in Figure 4(B), the conductive film 151f in areas that do not overlap with the resist mask 191 is removed. This forms the conductive layer 151.

[0258] Next, as shown in Figure 4(C), the resist mask 191 is removed. The resist mask 191 can be removed, for example, by ashing using oxygen plasma.

[0259] Next, as shown in Figure 4(D), insulating film 156f, which will later become insulating layer 156R, insulating layer 156G, insulating layer 156B, and insulating layer 156C, is formed on conductive layer 151R, conductive layer 151G, conductive layer 151B, conductive layer 151C, and insulating layer 175.

[0260] The insulating film 156f can be an inorganic insulating film such as an oxide insulating film, a nitride insulating film, an oxidative nitride insulating film, or a nitride oxide insulating film, for example, silicon oxidative nitride.

[0261] Next, as shown in Figure 4(E), insulating layer 156R, insulating layer 156G, insulating layer 156B, and insulating layer 156C are formed by processing the insulating film 156f.

[0262] Next, as shown in Figure 5(A), a conductive film 152f is formed on the conductive layer 151R, conductive layer 151G, conductive layer 151B, conductive layer 151C, insulating layer 156R, insulating layer 156G, insulating layer 156B, insulating layer 156C, and insulating layer 175.

[0263] For example, a conductive oxide can be used as the conductive film 152f. The conductive film 152f may be laminated.

[0264] Next, as shown in Figure 5(B), the conductive film 152f is processed to form conductive layers 152R, 152G, 152B, and 152C.

[0265] Next, as shown in Figure 5(C), the organic compound film 103Rf is formed on the conductive layer 152R, the conductive layer 152G, the conductive layer 152B, and the insulating layer 175. Note that, as shown in Figure 5(C), the organic compound film 103Rf is not formed on the conductive layer 152C.

[0266] Next, as shown in Figure 5(C), a sacrificial film 158Rf and a mask film 159Rf are formed.

[0267] 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.

[0268] 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.

[0269] 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 an organic compound represented by general formulas (G1) to (G4) shown in Embodiment 1, it is possible to provide a display device with good display quality even after undergoing a heating process at a higher temperature.

[0270] 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.

[0271] Furthermore, it is preferable that the sacrificial film 158Rf, which is formed in contact with the organic compound film 103Rf, is formed using a method that causes less damage to the organic compound film 103Rf than the mask film 159Rf. For example, ALD or vacuum deposition is preferred over sputtering.

[0272] The sacrificial film 158Rf and the mask film 159Rf can be one or more of the following, for example, metal films, alloy films, metal oxide films, semiconductor films, organic insulating films, and inorganic insulating films.

[0273] 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.

[0274] 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.

[0275] 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.

[0276] For the sacrificial film 158Rf and mask film 159Rf, it is preferable to use semiconductor materials such as silicon or germanium, for example, because they have high compatibility with semiconductor manufacturing processes. Alternatively, compounds containing the above semiconductor materials can be used.

[0277] 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.

[0278] Next, as shown in Figure 5(C), a resist mask 190R is formed. The resist mask 190R can be formed by applying a photosensitive material (photoresist), followed by exposure and development.

[0279] 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.

[0280] Next, as shown in Figure 5(D), 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.

[0281] By using the wet etching method, 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 aqueous tetramethylammonium hydroxide (TMAH), dilute hydrofluoric acid, oxalic acid, phosphoric acid, acetic acid, nitric acid, or a mixture thereof.

[0282] 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.

[0283] Resist mask 190R can be removed in the same manner as resist mask 191.

[0284] Next, as shown in Figure 5(D), 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.

[0285] As a result, as shown in Figure 5(D), the laminated structure of the organic compound layer 103R, the sacrificial layer 158R, and the mask layer 159R remains on the conductive layer 152R. In addition, the conductive layers 152G and 152B are exposed.

[0286] The organic compound film 103Rf is preferably processed by anisotropic etching. In particular, anisotropic dry etching is preferred. Alternatively, wet etching may be used.

[0287] 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.

[0288] Furthermore, an etching gas containing oxygen may be used. Including oxygen in the etching gas can increase the etching rate. Therefore, etching can be performed under low power conditions while maintaining a sufficiently fast etching rate. This suppresses damage to the organic compound film 103Rf. In addition, it suppresses problems such as the adhesion of reaction products generated during etching.

[0289] When using the dry etching method, it is preferable to use a gas containing one or more of the Group 18 elements, such as H2, CF4, C4F8, SF6, CHF3, Cl2, H2O, BCl3, or He, Ar, as the etching gas. Alternatively, it is preferable to use a gas containing one or more of these elements and oxygen as the etching gas. Alternatively, oxygen gas may be used as the etching gas.

[0290] Next, as shown in Figure 6(A), an organic compound film 103Gf, which will later become the organic compound layer 103G, is formed.

[0291] 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.

[0292] Next, as shown in Figure 6(A), a sacrificial film 158Gf and a mask film 159Gf are formed in sequence. After that, a resist mask 190G is formed. The materials and formation methods for the sacrificial film 158Gf and mask film 159Gf are the same as those applicable to the sacrificial film 158Rf and mask film 159Rf. The materials and formation methods for the resist mask 190G are the same as those applicable to the resist mask 190R.

[0293] The resist mask 190G is placed in a position that overlaps with the conductive layer 152G.

[0294] Next, as shown in Figure 6(B), a portion of the mask film 159Gf is removed using the resist mask 190G to form a mask layer 159G. The mask layer 159G remains on the conductive layer 152G. After that, the resist mask 190G is removed. Next, the mask layer 159G is used as a mask to remove a portion of the sacrificial film 158Gf to form a sacrificial layer 158G. Subsequently, the organic compound film 103Gf is processed to form an organic compound layer 103G.

[0295] Next, as shown in Figure 6(C), an organic compound film 103Bf is formed.

[0296] The organic compound film 103Bf can be formed by the same method as that used to form the organic compound film 103Rf. Furthermore, the organic compound film 103Bf can have the same structure as the organic compound film 103Rf.

[0297] Next, as shown in Figure 6(C), the sacrificial film 158Bf and the mask film 159Bf are formed in sequence. After that, the resist mask 190B is formed. The materials and formation methods for the sacrificial film 158Bf and the mask film 159Bf are the same as those applicable to the sacrificial film 158Rf and the mask film 159Rf. The materials and formation methods for the resist mask 190B are the same as those applicable to the resist mask 190R.

[0298] The resist mask 190B is placed in a position that overlaps with the conductive layer 152B.

[0299] Next, as shown in Figure 6(D), a portion of the mask film 159Bf is removed using the resist mask 190B to form the mask layer 159B. The mask layer 159B remains on the conductive layer 152B. After that, the resist mask 190B is removed. Next, the mask layer 159B is used as a mask to remove a portion of the sacrificial film 158Bf to form the sacrificial layer 158B. Next, the organic compound film 103Bf is processed to form the organic compound layer 103B. For example, the mask layer 159B and the sacrificial layer 158B are used as a hard mask to remove a portion of the organic compound film 103Bf to form the organic compound layer 103B.

[0300] As a result, as shown in Figure 6(D), the laminated structure of the organic compound layer 103B, the sacrificial layer 158B, and the mask layer 159B remains on the conductive layer 152B. In addition, the mask layers 159R and 159G are exposed.

[0301] 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.

[0302] As described above, the distance between two adjacent organic compound layers 103R, 103G, and 103B formed using photolithography can be narrowed to 8 μm or less, 5 μm or less, 3 μm or less, 2 μm or less, or 1 μm or less. Here, this distance can be defined, for example, by the distance between two adjacent opposing ends of organic compound layers 103R, 103G, and 103B. By narrowing the distance between the island-like organic compound layers in this way, a display device with high resolution and a large aperture ratio can be provided. Furthermore, the distance between the first electrodes between adjacent light-emitting devices can also be narrowed, for example, to 10 μm or less, 8 μm or less, 5 μm or less, 3 μm or less, or 2 μm or less. It is preferable that the distance between the first electrodes between adjacent light-emitting devices is 2 μm or more and 5 μm or less.

[0303] Next, as shown in Figure 7(A), it is preferable to remove the mask layer 159R, mask layer 159G, and mask layer 159B.

[0304] The same method as the mask layer processing method can be used for the mask layer removal process. In particular, by using a wet etching method, the damage inflicted on the organic compound layer 103 when removing the mask layer can be reduced compared to when using a dry etching method.

[0305] 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.

[0306] 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.

[0307] Next, as shown in Figure 7(B), an inorganic insulating film 125f is formed.

[0308] Next, as shown in Figure 7(C), an insulating film 127f, which will later become the insulating layer 127, is formed on the inorganic insulating film 125f.

[0309] The substrate temperature when forming the inorganic insulating film 125f and insulating film 127f is preferably 60°C or higher, 80°C or higher, 100°C or higher, or 120°C or higher, and 200°C or lower, 180°C or lower, 160°C or lower, 150°C or lower, or 140°C or lower, respectively.

[0310] 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.

[0311] The inorganic insulating film 125f is preferably formed using, for example, the ALD method. The ALD method is preferable because it can reduce film formation damage and allow for the formation of a highly covering film. For example, it is preferable to form an aluminum oxide film as the inorganic insulating film 125f using the ALD method.

[0312] 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.

[0313] 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.

[0314] 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.

[0315] 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).

[0316] Next, as shown in Figure 8(A), development is performed to remove the exposed area of ​​the insulating film 127f and form the insulating layer 127a.

[0317] Next, as shown in Figure 8(B), etching is performed using the insulating layer 127a as a mask to remove a portion of the inorganic insulating film 125f and thin the film thickness of parts of the sacrificial layer 158R, sacrificial layer 158G, and sacrificial layer 158B. As a result, the inorganic insulating layer 125 is formed beneath the insulating layer 127a. In addition, the surfaces of the thinned portions of the sacrificial layer 158R, sacrificial layer 158G, and sacrificial layer 158B are exposed. In the following, the etching process using the insulating layer 127a as a mask may be referred to as the first etching process.

[0318] 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.

[0319] When performing dry etching, it is preferable to use a chlorine-based gas. As chlorine-based gases, Cl2, BCl3, SiCl4, and CCl4 can be used individually or in mixtures of two or more gases. In addition, oxygen gas, hydrogen gas, helium gas, and argon gas can be added to the above chlorine-based gases individually or in mixtures of two or more gases as appropriate. By using dry etching, regions with thin film thickness in sacrificial layers 158R, 158G, and 158B can be formed with good in-plane uniformity.

[0320] 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.

[0321] Furthermore, it is preferable to perform the first etching process by wet etching. By using the wet etching method, damage to the organic compound layer 103R, organic compound layer 103G, and organic compound layer 103B can be reduced compared to when the dry etching method is used. For example, wet etching can be performed using an alkaline solution. For example, TMAH, which is an alkaline solution, can be used for wet etching of an aluminum oxide film. Alternatively, an acidic solution containing fluoride can be used. In this case, wet etching can be performed using a paddle method. It is preferable that the inorganic insulating film 125f is deposited using the same material as the sacrificial layer 158R, sacrificial layer 158G, and sacrificial layer 158B, as the above etching process can be performed in a single step.

[0322] 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.

[0323] 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.

[0324] Here, the presence of oxygen barrier insulating layers (e.g., an aluminum oxide film) as sacrificial layers 158R, 158G, and 158B reduces the diffusion of oxygen into organic compound layers 103R, 103G, and 103B.

[0325] Next, a heat treatment (also called post-bake) is performed. By performing the heat treatment, the insulating layer 127a can be deformed into an insulating layer 127 having a tapered shape on its side surface (Figure 8(C)). This heat treatment is performed at a temperature lower than the heat resistance temperature of the organic compound layer. The heat treatment can be performed at a substrate temperature of 50°C to 200°C, preferably 60°C to 150°C, and more preferably 70°C to 130°C. The heating atmosphere may be an atmospheric atmosphere or an inert gas atmosphere. The heating atmosphere may also be an atmospheric pressure atmosphere or a reduced pressure atmosphere. This improves the adhesion between the insulating layer 127 and the inorganic insulating layer 125, and also improves the corrosion resistance of the insulating layer 127.

[0326] In the first etching process, by not completely removing sacrificial layers 158R, 158G, and 158B, and leaving them in a thinned state, it is possible to prevent damage and degradation of organic compound layers 103R, 103G, and 103B during the heat treatment. Therefore, the reliability of the light-emitting device can be improved.

[0327] Next, as shown in Figure 9(A), etching is performed using the insulating layer 127 as a mask to remove a portion of the sacrificial layer 158R, sacrificial layer 158G, and sacrificial layer 158B. This creates openings in each of the sacrificial layer 158R, sacrificial layer 158G, and sacrificial layer 158B, exposing the upper surfaces of the organic compound layer 103R, organic compound layer 103G, organic compound layer 103B, and conductive layer 152C. In the following, this etching process may be referred to as the second etching process.

[0328] The edges of the inorganic insulating layer 125 are covered with the insulating layer 127. Figure 9(A) also shows an example where the insulating layer 127 covers a portion of the edge of the sacrificial layer 158G (specifically, the tapered portion formed by the first etching process), while the tapered portion formed by the second etching process is exposed.

[0329] 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.

[0330] Next, as shown in Figure 9(B), 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 sputtering or vacuum deposition. At this time, as shown in Figure 3, the organic compound layer 103 may be formed as a laminated structure of the organic compound layer 103 and the second layer 105, and the common electrode 155 may be formed on top of that.

[0331] Next, as shown in Figure 9(C), 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.

[0332] 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 the method for manufacturing a display device according to one aspect 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.

[0333] 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 makes it possible to prevent crosstalk and realize a display device with extremely high contrast. Moreover, even a display device having a tandem type light-emitting device manufactured using photolithography can be provided with good characteristics.

[0334] (Embodiment 4) This embodiment describes a display device according to one aspect of the present invention.

[0335] The display device of this embodiment can be a high-definition display device. Therefore, the display device of this embodiment can be used, for example, as a display unit for information terminals (wearable devices) such as wristwatches and bracelets, and as a display unit for wearable devices that can be worn on the head, such as VR devices such as head-mounted displays (HMDs) and AR devices such as glasses.

[0336] Furthermore, the display device of this embodiment can be a high-resolution display device or a large-screen display device. Therefore, the display device of this embodiment can be used in electronic devices with relatively large screens, such as television equipment, desktop or notebook personal computers, computer monitors, digital signage, and large game machines such as pachinko machines, as well as in the display units of digital cameras, digital video cameras, digital photo frames, mobile phones, portable game consoles, personal information terminals, and audio playback devices.

[0337] [Display Module] Figure 10(A) shows a perspective view of the display module 280. The display module 280 includes a display device 100A and an FPC 290. Note that the display device included in the display module 280 is not limited to display device 100A, but may be any of the display devices 100B to 100E described later.

[0338] The display module 280 has substrates 291 and 292. The display module 280 has a display unit 281. The display unit 281 is an area in the display module 280 that displays an image, and is an area in which light from each pixel provided in the pixel unit 284, which will be described later, can be seen.

[0339] Figure 10(B) shows a schematic perspective view illustrating the configuration of the substrate 291. On the substrate 291, a circuit section 282, a pixel circuit section 283 on the circuit section 282, and a pixel section 284 on the pixel circuit section 283 are stacked. In addition, a terminal section 285 for connecting to the FPC 290 is provided in the portion of the substrate 291 that does not overlap with the pixel section 284. The terminal section 285 and the circuit section 282 are electrically connected by a wiring section 286, which is composed of multiple wires.

[0340] The pixel section 284 has a plurality of pixels 284a arranged periodically. A magnified view of one pixel 284a is shown on the right side of Figure 10(B). Various configurations described in the previous embodiment can be applied to the pixel 284a. Figure 10(B) shows an example where the pixel 284a has a configuration similar to the pixel 178 shown in Figure 3.

[0341] The pixel circuit section 283 has a plurality of pixel circuits 283a arranged periodically.

[0342] One pixel circuit 283a is a circuit that controls the driving of multiple elements that a single pixel 284a has.

[0343] 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.

[0344] The FPC290 functions as wiring for supplying video signals or power potential, etc., to the circuit section 282 from an external source. An IC may also be mounted on the FPC290.

[0345] Since the display module 280 can be configured such that one or both of the pixel circuit section 283 and the circuit section 282 are stacked on the lower side of the pixel section 284, the aperture ratio (effective display area ratio) of the display section 281 can be made extremely high.

[0346] Because such a display module 280 is extremely high-resolution, it can be suitably used in VR devices such as HMDs or AR devices such as glasses. For example, even in a configuration where the display part of the display module 280 is viewed through lenses, the display module 280 has an extremely high-resolution display part 281, so even when the display part is magnified with lenses, pixels are not visible, and a highly immersive display can be achieved. Furthermore, the display module 280 is not limited to this and can be suitably used in electronic devices having relatively small display parts.

[0347] [Display device 100A] The display device 100A shown in Figure 11(A) includes a substrate 301, light-emitting devices 130R, 130G, 130B, a capacitor 240, and a transistor 310.

[0348] Substrate 301 corresponds to substrate 291 in Figures 10(A) and 10(B). Transistor 310 is a transistor having a channel formation region in substrate 301. For substrate 301, a semiconductor substrate such as a single-crystal silicon substrate can be used. Transistor 310 has a part of substrate 301, a conductive layer 311, a low-resistance region 312, an insulating layer 313, and an insulating layer 314. The conductive layer 311 functions as a gate electrode. The insulating layer 313 is located between substrate 301 and the conductive layer 311 and functions as a gate insulating layer. The low-resistance region 312 is a region of substrate 301 doped with impurities and functions as a source or drain. The insulating layer 314 is provided covering the side surface of the conductive layer 311.

[0349] Furthermore, an element isolation layer 315 is provided between two adjacent transistors 310 so as to be embedded in the substrate 301.

[0350] Furthermore, an insulating layer 261 is provided covering the transistor 310, and a capacitance 240 is provided on the insulating layer 261.

[0351] The capacitor 240 has a conductive layer 241, a conductive layer 245, and an insulating layer 243 located between them. The conductive layer 241 acts as one electrode of the capacitor 240, the conductive layer 245 acts as the other electrode of the capacitor 240, and the insulating layer 243 acts as the dielectric of the capacitor 240.

[0352] 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.

[0353] 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.

[0354] 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.

[0355] 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.

[0356] 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 3. The substrate 120 corresponds to the substrate 292 in Figure 10(A).

[0357] Figure 11(B) shows a modified example of the display device 100A shown in Figure 11(A). The display device shown in Figure 11(B) has a colored layer 132R, a colored layer 132G, and a colored layer 132B, and the light-emitting device 130 has a region that overlaps with one of the colored layers 132R, 132G, and 132B. In the display device shown in Figure 11(B), the light-emitting device 130 can emit, for example, white light. Also, for example, the colored layer 132R can transmit red light, the colored layer 132G can transmit green light, and the colored layer 132B can transmit blue light.

[0358] [Display device 100B] Figure 12 shows a perspective view of the display device 100B, and Figure 13 shows a cross-sectional view of the display device 100B, designated as the display device 100C.

[0359] 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.

[0360] The display device 100B includes a pixel section 177, a connection section 140, a circuit 356, and wiring 355, etc. Figure 12 shows an example in which IC 354 and FPC 353 are mounted on the display device 100B. Therefore, the configuration shown in Figure 12 can also be called a display module having the display device 100B, an IC (integrated circuit), and an FPC. Here, a display module is a display device on which a connector such as an FPC is attached, or on which an IC is mounted.

[0361] 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.

[0362] For example, a scan line drive circuit can be used as circuit 356.

[0363] 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.

[0364] Figure 12 shows an example in which IC 354 is mounted on substrate 351 using COG (Chip On Glass) or COF (Chip On Film) methods. IC 354 can be an IC having, for example, a scan line drive circuit or a signal line drive circuit. Note that the display device 100B and the display module may be configured without an IC. Alternatively, the IC may be mounted on an FPC, for example, using the COF method.

[0365] Figure 13 shows an example of a cross-section of the display device 100B when a portion of the area including the FPC 353, a portion of the circuit 356, a portion of the pixel portion 177, a portion of the connection portion 140, and a portion of the area including the end portion are cut.

[0366] [Display device 100C] The display device 100C shown in Figure 13 has a transistor 201, a transistor 205, a light-emitting device 130R that emits red light, a light-emitting device 130G that emits green light, and a light-emitting device 130B that emits blue light, etc., between substrates 351 and 352.

[0367] Details of the light-emitting devices 130R, 130G, and 130B can be found in Embodiment 1.

[0368] 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.

[0369] The conductive layer 224R is connected to the conductive layer 222b of the transistor 205 through an opening provided in the insulating layer 214. The edge of the conductive layer 151R is located outside the edge of the conductive layer 224R. The insulating layer 156R is provided so as to have a region in contact with the side surface of the conductive layer 151R, and the conductive layer 152R is provided so as to cover the conductive layer 151R and the insulating layer 156R.

[0370] 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.

[0371] 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.

[0372] Layer 128 has the function of 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.

[0373] 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.

[0374] A protective layer 131 is provided on the light-emitting devices 130R, 130G, and 130B. The protective layer 131 and the substrate 352 are bonded via an adhesive layer 142. A light-shielding layer 157 is provided on the substrate 352. A solid encapsulation structure or a hollow encapsulation structure can be applied to encapsulate the light-emitting devices 130. In Figure 13, the space between the substrate 352 and the substrate 351 is filled with the adhesive layer 142, indicating a solid encapsulation structure. Alternatively, the space may be filled with an inert gas (such as nitrogen or argon), indicating a hollow encapsulation structure. In this case, the adhesive layer 142 may be provided 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, which is provided in a frame shape.

[0375] 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.

[0376] The display device 100B 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. If the light-emitting device emits infrared or near-infrared light, it is preferable to use a material with high transmittance to those. The pixel electrodes contain a material that reflects visible light, and the counter electrodes (common electrodes 155) contain a material that transmits visible light.

[0377] 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.

[0378] It is preferable to use an inorganic insulating film as the insulating layer 211, insulating layer 213, and insulating layer 215.

[0379] An organic insulating layer is preferred for the insulating layer 214, which functions as a planarizing layer.

[0380] Transistors 201 and 205 each 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.

[0381] A connection portion 204 is provided in the region of substrate 351 where substrate 352 does not overlap. At the connection portion 204, the wiring 355 is electrically connected to the FPC 353 via the conductive layer 166 and the connecting layer 242. The conductive layer 166 is shown as an example of a laminated structure consisting of a conductive film obtained by processing the same conductive film as conductive layers 224R, 224G, and 224B, a conductive film obtained by processing the same conductive film as conductive layers 151R, 151G, and 151B, and a conductive film obtained by processing the same conductive film as conductive layers 152R, 152G, and 152B. On the upper surface of the connection portion 204, the conductive layer 166 is exposed. This allows the connection portion 204 and the FPC 353 to be electrically connected via the connecting layer 242.

[0382] It is preferable to provide a light-shielding layer 157 on the surface of the substrate 352 that faces the substrate 351. The light-shielding layer 157 can be provided between adjacent light-emitting devices, at connection points 140, and in circuits 356, etc. In addition, various optical components can be arranged on the outside of the substrate 352.

[0383] Materials that can be used for substrate 120 can be applied to substrate 351 and substrate 352, respectively.

[0384] As the adhesive layer 142, a material that can be used for the resin layer 122 can be applied.

[0385] As the connecting layer 242, an anisotropic conductive film (ACF) or an anisotropic conductive paste (ACP) can be used.

[0386] [Display device 100D] The display device 100D shown in Figure 14 differs from the display device 100C shown in Figure 13 mainly in that it is a bottom-emission type display device.

[0387] The light emitted by the light-emitting device is projected onto the substrate 351. It is preferable to use a material with high transparency to visible light for the substrate 351. On the other hand, the light transmittance of the material used for the substrate 352 is not a requirement.

[0388] It is preferable to form a light-shielding layer 157 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 157 is provided on the substrate 351, an insulating layer 153 is provided on the light-shielding layer 157, and transistors 201, 205, etc. are provided on the insulating layer 153.

[0389] 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.

[0390] 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.

[0391] 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 common electrode 155.

[0392] Although the light-emitting device 130G is not shown in Figure 14, it is also provided.

[0393] 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.

[0394] [Display device 100E] The display device 100E shown in Figure 15 is a modified version of the display device 100B shown in Figure 13, and differs from the display device 100B mainly in that it has a colored layer 132R, a colored layer 132G, and a colored layer 132B.

[0395] 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.

[0396] In the display device 100E, the light-emitting device 130 can emit, for example, white light. Furthermore, for example, the colored layer 132R can transmit red light, the colored layer 132G can transmit green light, and the colored layer 132B can transmit blue light. The display device 100E may also be configured with the colored layers 132R, 132G, and 132B placed between the protective layer 131 and the adhesive layer 142.

[0397] Figures 13 to 15 show an example in which the upper surface of layer 128 has a flat portion, but the shape of layer 128 is not particularly limited.

[0398] 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.

[0399] (Embodiment 5) This embodiment describes an electronic device according to one aspect of the present invention.

[0400] 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 high display performance and is easily made high-definition and high-resolution. Therefore, it can be used in the display units of various electronic devices.

[0401] 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.

[0402] In particular, a display device according to one aspect of the present invention can be used suitably in electronic devices having a relatively small display area because it can increase the resolution. Examples of such electronic devices include wristwatch-type and bracelet-type information terminals (wearable devices), as well as wearable devices that can be worn on the head, such as VR devices such as head-mounted displays, AR devices such as glasses, and MR devices.

[0403] The electronic device of this embodiment may have sensors (including those with functions to measure 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).

[0404] An example of a wearable device that can be worn on the head is illustrated using Figures 16(A) to 16(D).

[0405] The electronic device 700A shown in Figure 16(A) and the electronic device 700B shown in Figure 16(B) each include a pair of display panels 751, a pair of housings 721, a communication unit (not shown), a pair of mounting units 723, a control unit (not shown), an imaging unit (not shown), a pair of optical members 753, a frame 757, and a pair of nose pads 758.

[0406] 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.

[0407] Electronic devices 700A and 700B can project an image displayed on the display panel 751 onto the display area 756 of the optical element 753. Because the optical element 753 is translucent, the user can see the image displayed on the display area superimposed on the transmitted image visible through the optical element 753.

[0408] 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.

[0409] 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.

[0410] Furthermore, electronic devices 700A and 700B are equipped with batteries that can be charged wirelessly, wired, or both.

[0411] The housing 721 may be provided with a touch sensor module.

[0412] 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.

[0413] The electronic device 800A shown in Figure 16(C) and the electronic device 800B shown in Figure 16(D) each include a pair of display units 820, a housing 821, a communication unit 822, a pair of mounting units 823, a control unit 824, a pair of imaging units 825, and a pair of lenses 832.

[0414] 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.

[0415] The display unit 820 is located inside the housing 821, in a position where it can be seen through the lens 832. Furthermore, by displaying different images on a pair of display units 820, a three-dimensional display using parallax can also be performed.

[0416] 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.

[0417] The attachment part 823 allows the user to attach the electronic device 800A or the electronic device 800B to their head.

[0418] 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.

[0419] The electronic device 800A may have a vibration mechanism that functions as a bone conduction earphone.

[0420] Electronic devices 800A and 800B may each have input terminals. Cables can be connected to the input terminals to supply video signals from video output devices, etc., and power for charging batteries provided within the electronic devices.

[0421] An electronic device according to one aspect of the present invention may have a function for wireless communication with an earphone 750.

[0422] Furthermore, the electronic device may have an earphone section. The electronic device 700B shown in Figure 16(B) has an earphone section 727. Some of the wiring connecting the earphone section 727 and the control unit may be located inside the housing 721 or the mounting section 723.

[0423] Similarly, the electronic device 800B shown in Figure 16(D) has an earphone unit 827. For example, the earphone unit 827 and the control unit 824 can be connected to each other by a wire.

[0424] 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.

[0425] The electronic device 6500 shown in Figure 17(A) is a portable information terminal that can be used as a smartphone.

[0426] 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.

[0427] 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.

[0428] Figure 17(B) is a schematic cross-sectional view of the housing 6501 including the end on the microphone 6506 side.

[0429] 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.

[0430] 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).

[0431] 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.

[0432] 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.

[0433] Figure 17(C) shows an example of a television system. The television system 7100 has a display unit 7000 incorporated into a housing 7171. Here, the housing 7171 is shown supported by a stand 7173.

[0434] 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.

[0435] The television device 7100 shown in Figure 17(C) can be operated using the operation switches on the housing 7171 and a separate remote control unit 7151.

[0436] Figure 17(D) shows an example of a notebook personal computer. The notebook personal computer 7200 has a casing 7211, a keyboard 7212, a pointing device 7213, and an external connection port 7214, etc. A display unit 7000 is incorporated into the casing 7211.

[0437] 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.

[0438] Figures 17(E) and 17(F) show examples of digital signage.

[0439] The digital signage 7300 shown in Figure 17(E) comprises a housing 7301, a display unit 7000, and a speaker 7303, etc. Furthermore, it may include LED lamps, operation keys (including a power switch or operation switch), connection terminals, various sensors, a microphone, etc.

[0440] Figure 17(F) shows a digital signage 7400 mounted on a cylindrical column 7401. The digital signage 7400 has a display unit 7000 that is provided along the curved surface of the column 7401.

[0441] In Figures 17(E) and 17(F), a display device according to one embodiment of the present invention can be applied to the display unit 7000. Therefore, a highly reliable electronic device can be made.

[0442] 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.

[0443] Furthermore, as shown in Figures 17(E) and 17(F), it is preferable that the digital signage 7300 or digital signage 7400 can be linked wirelessly with an information terminal 7311 or information terminal 7411 such as a smartphone owned by the user.

[0444] The electronic equipment shown in Figures 18(A) to 18(G) includes a housing 9000, a display unit 9001, a speaker 9003, operation keys 9005 (including a power switch or operation switch), connection terminals 9006, sensors 9007 (including functions for measuring force, displacement, position, velocity, acceleration, angular velocity, rotational speed, distance, light, liquid, magnetism, temperature, chemical substances, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared radiation), a microphone 9008, etc.

[0445] The electronic devices shown in Figures 18(A) to 18(G) 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, etc.

[0446] Details of the electronic equipment shown in Figures 18(A) to 18(G) will be explained below.

[0447] Figure 18(A) is a perspective view showing a personal digital information terminal (PDI) 9171. The PDI 9171 can be used, for example, as a smartphone. The PDI 9171 may also be equipped with a speaker 9003, a connection terminal 9006, or a sensor 9007. Furthermore, the PDI 9171 can display text and image information on multiple surfaces. Figure 18(A) shows an example where three icons 9050 are displayed. Information 9051, indicated by a dashed rectangle, can also be displayed on other surfaces of the display unit 9001. Examples of information 9051 include notifications of incoming emails, SNS messages, phone calls, etc., the subject of emails or SNS messages, the sender's name, date and time, time, battery level, signal strength, etc. Alternatively, icons 9050, etc., may be displayed in the position where the information 9051 is displayed.

[0448] Figure 18(B) is a perspective view showing the personal digital assistant (PDA) 9172. The PDA 9172 has the function of displaying information on three or more sides of the display unit 9001. Here, an example is shown in which information 9052, information 9053, and information 9054 are displayed on different sides. For example, a user can check information 9053, which is displayed in a position that can be observed from above the PDA 9172, while the PDA 9172 is stored in the breast pocket of their clothing.

[0449] Figure 18(C) is a perspective view showing the tablet terminal 9173. The tablet terminal 9173 can run various applications, such as mobile phone calls, email, document viewing and creation, music playback, internet communication, and computer games. The tablet terminal 9173 has a display unit 9001, a camera 9002, a microphone 9008, and a speaker 9003 on the front of the housing 9000. The left side of the housing 9000 has operation keys 9005 as buttons for operation, and the bottom has connection terminals 9006.

[0450] Figure 18(D) is a perspective view showing a wristwatch-type personal information terminal 9200. The personal information terminal 9200 can be used, for example, as a smartwatch (registered trademark). The display unit 9001 has a curved display surface, allowing it to display information along the curved surface. The personal information terminal 9200 can also make hands-free calls by communicating with, for example, a wireless communication headset. Furthermore, the personal information terminal 9200 can transmit data to other information terminals and be charged via the connection terminal 9006. Charging may be performed by wireless power supply.

[0451] Figures 18(E) to 18(G) are perspective views showing a foldable portable information terminal 9201. Figure 18(E) shows the portable information terminal 9201 in an unfolded state, Figure 18(G) shows it in a folded state, and Figure 18(F) shows a state in between, transitioning from one of Figures 18(E) or 18(G) to the other. The portable information terminal 9201 offers excellent portability in its folded state and excellent readability of the display due to its seamless, wide display area in its unfolded state. The display unit 9001 of the portable information terminal 9201 is supported by three housings 9000 connected by hinges 9055. For example, the display unit 9001 can be bent with a radius of curvature of 0.1 mm to 150 mm.

[0452] This embodiment can be appropriately combined with other embodiments or examples. Furthermore, if multiple configuration examples are shown within a single embodiment in this specification, these configuration examples can be appropriately combined. [Examples]

[0453] In this embodiment, the detailed manufacturing method and characteristics of light-emitting devices 1 and 2 according to one aspect of the present invention, as well as a comparative light-emitting device 1, will be described.

[0454] The structural formulas of the main compounds used in this example are shown below.

[0455] [ka]

[0456] (Method for fabricating light-emitting device 1) First, a 100 nm layer of silver (Ag) was sequentially layered on a glass substrate using a sputtering method, and a 10 nm layer of indium tin oxide (ITSO) containing silicon dioxide was sequentially layered on the glass substrate using a sputtering method to form a first electrode 101 measuring 2 mm x 2 mm. The transparent electrode functions as an anode and, together with the reflective electrode, is considered to be part of the first electrode 101.

[0457] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water, baked at 200°C for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

[0458] After that, approximately 1 × 10 -4 The substrate was introduced into a vacuum deposition apparatus where the internal pressure was reduced to Pa. After vacuum firing at 170°C for 60 minutes in the heating chamber of the vacuum deposition apparatus, the substrate was allowed to cool for approximately 30 minutes.

[0459] Next, the substrate was fixed to a holder provided in the vacuum deposition apparatus so that the surface on which the first electrode 101 was formed was facing downwards. On the first electrode 101, a hole injection layer 111 was formed by co-depositing 10 nm of N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviated as PCBBiF), represented by the above structural formula (i), and an electron acceptor material (OCHD-003) containing fluorine with a molecular weight of 672, in a weight ratio of 1:0.03 (=PCBBiF:OCHD-003).

[0460] A 20 nm layer of PCBBiF was deposited on the hole injection layer 111 to form a first hole transport layer.

[0461] Next, on the first hole transport layer, 4,8-bis[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofloflo[3,2-d]pyrimidine (abbreviated as 4,8mDBtP2Bfpm), represented by the above structural formula (ii), 9-(2-naphthyl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviated as βNCCP), represented by the above structural formula (iii), and [2-d3], represented by the above structural formula (iv) -methyl-(2-pyridinyl-κN)benzofl[2,3-b]pyridine-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(ppy)2(mbfpypy-d3)) was co-deposited at a weight ratio of 0.5:0.5:0.1 (=4,8mDBtP2Bfpm:βNCCP:Ir(ppy)2(mbfpypy-d3)) at a thickness of 40 nm to form the first light-emitting layer.

[0462] Subsequently, 2-{3-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-9-yl]phenyl}dibenzo[f,h]quinoxaline (abbreviation: 2mPCCzPDBq), represented by the above structural formula (v), was deposited to a thickness of 35 nm to form the first electron transport layer.

[0463] After the formation of the first electron transport layer, 2,2'-(1,3-phenylene)bis(9-phenyl-1,10-phenanthroline) (abbreviated as mPPhen2P), represented by the above structural formula (vi), and 2,9-bis(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine-1-yl)-1,10-phenanthroline (abbreviated as 2,9hpp2Phen), represented by the above structural formula (vii), were co-deposited at a weight ratio of 1:1 (=mPPhen2P:2,9hpp2Phen) to a thickness of 5 nm. Copper phthalocyanine (abbreviated as CuPc), represented by the above structural formula (viii), was deposited at a thickness of 2 nm. Furthermore, PCBBiF and OCHD-003 were co-deposited at a weight ratio of 1:0.15 (=PCBBiF:OCHD-003) to a thickness of 10 nm to form an intermediate layer.

[0464] A second hole transport layer was formed by depositing PCBBiF at a 40 nm layer on the intermediate layer.

[0465] A second light-emitting layer was formed on the second hole transport layer by co-depositing 4,8mDBtP2Bfpm, βNCCP, and Ir(ppy)2(mbfpypy-d3) at a weight ratio of 0.5:0.5:0.1 (=4,8mDBtP2Bfpm:βNCCP:Ir(ppy)2(mbfpypy-d3)) at a thickness of 40 nm.

[0466] Subsequently, 2mPCCzPDBq was deposited to a thickness of 20 nm, and then mPPhen2P was deposited to a thickness of 20 nm to form a second electron transport layer.

[0467] Then, under vacuum (approximately 1 x 10⁻⁶) -4 At Pa, lithium fluoride (LiF) and ytterbium (Yb) were co-deposited at a volume ratio of 1:0.5 (=LiF:Yb) to a thickness of 1.5 nm. Subsequently, silver (Ag) and magnesium (Mg) were co-deposited at a volume ratio of 1:0.1 to a thickness of 15 nm to form a second electrode 102, thereby fabricating a light-emitting device according to one embodiment of the present invention. Furthermore, a 70 nm film of 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviated as DBT3P-II), represented by the above structural formula (ix), was deposited on the second electrode 102 as a cap layer to improve the light extraction efficiency.

[0468] 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.

[0469] (Method for fabricating light-emitting device 2) Light-emitting device 2 was fabricated in the same manner as light-emitting device 1, except that 2,9hpp2Phen in light-emitting device 1 was replaced with 4,7-bis(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine-1-yl)-1,10-phenanthroline (abbreviated as 4,7hpp2Phen), represented by the above structural formula (x).

[0470] (Method for fabricating comparative light-emitting device 1) Comparative light-emitting device 1 was fabricated in the same manner as light-emitting device 1, except that 2,9hpp2Phen in light-emitting device 1 was replaced with 1,1'-pyridine-2,6-diyl-bis(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine) (abbreviated as hpp2Py), represented by the above structural formula (xi).

[0471] The device structures of light-emitting device 1, light-emitting device 2, and comparative light-emitting device 1 are shown below.

[0472] [Table 1]

[0473] Figure 19 shows the luminance-current density characteristics of light-emitting device 1, light-emitting device 2, and comparative light-emitting device 1, Figure 20 shows the luminance-voltage characteristics, Figure 21 shows the current efficiency-luminance characteristics, Figure 22 shows the current-voltage characteristics, and Figure 23 shows the emission spectra. 2 Table 2 shows the main characteristics of the vicinity. Luminance, CIE chromaticity, and emission spectrum were measured using a spectroradiometer (Topcon SR-UL1R) at room temperature.

[0474] [Table 2]

[0475] As shown in Figures 19 to 23, it was found that light-emitting devices 1 and 2 are light-emitting devices with good current efficiency, especially in the low-brightness region.

[0476] Next, a current density of 50 mA / cm². 2 Figure 24 shows the results of measuring the change in brightness with respect to the operating time during constant current drive. From Figure 24, it can be seen that light-emitting device 1 and light-emitting device 2 are light-emitting devices with better characteristics, having a longer lifespan than comparative light-emitting device 1. [Examples]

[0477] In this embodiment, the detailed manufacturing method and characteristics of a light-emitting device 3 according to one aspect of the present invention and a comparative light-emitting device 2 will be described.

[0478] The structural formulas of the main compounds used in this example are shown below.

[0479] [ka]

[0480] (Method for fabricating light-emitting device 3) First, a 100 nm layer of silver (Ag) was sequentially layered on a glass substrate using a sputtering method, and a 10 nm layer of indium tin oxide (ITSO) containing silicon dioxide was sequentially layered on the glass substrate using a sputtering method to form a first electrode 101 measuring 2 mm x 2 mm. The transparent electrode functions as an anode and, together with the reflective electrode, is considered to be part of the first electrode 101.

[0481] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water, baked at 200°C for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

[0482] After that, approximately 1 × 10 -4 The substrate was introduced into a vacuum deposition apparatus where the internal pressure was reduced to Pa. After vacuum firing at 170°C for 60 minutes in the heating chamber of the vacuum deposition apparatus, the substrate was allowed to cool for approximately 30 minutes.

[0483] Next, the substrate was fixed to a holder provided in the vacuum deposition apparatus so that the surface on which the first electrode 101 was formed was facing downwards. On the first electrode 101, a hole injection layer 111 was formed by co-depositing 10 nm of N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviated as PCBBiF), represented by the above structural formula (i), and an electron acceptor material (OCHD-003) containing fluorine with a molecular weight of 672, in a weight ratio of 1:0.03 (=PCBBiF:OCHD-003).

[0484] A 20 nm layer of PCBBiF was deposited on the hole injection layer 111 to form a first hole transport layer.

[0485] Next, on the first hole transport layer, 4,8-bis[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofloflo[3,2-d]pyrimidine (abbreviated as 4,8mDBtP2Bfpm), represented by the above structural formula (ii), 9-(2-naphthyl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviated as βNCCP), represented by the above structural formula (iii), and [2-d3], represented by the above structural formula (iv) -methyl-(2-pyridinyl-κN)benzofl[2,3-b]pyridine-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(ppy)2(mbfpypy-d3)) was co-deposited at a weight ratio of 0.5:0.5:0.1 (=4,8mDBtP2Bfpm:βNCCP:Ir(ppy)2(mbfpypy-d3)) at a thickness of 40 nm to form the first light-emitting layer.

[0486] Subsequently, 2-{3-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-9-yl]phenyl}dibenzo[f,h]quinoxaline (abbreviation: 2mPCCzPDBq), represented by the above structural formula (v), was deposited to a thickness of 25 nm to form the first electron transport layer.

[0487] After the formation of the first electron transport layer, 2,9-bis(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine-1-yl)-1,10-phenanthroline (abbreviated as 2,9hpp2Phen), represented by the above structural formula (vii), was deposited to a thickness of 5 nm. Then, copper phthalocyanine (abbreviated as CuPc), represented by the above structural formula (viii), was deposited to a thickness of 2 nm. Furthermore, PCBBiF and OCHD-003 were co-deposited at a weight ratio of 1:0.15 (=PCBBiF:OCHD-003) to form an intermediate layer at a thickness of 10 nm.

[0488] A second hole transport layer was formed by depositing PCBBiF at a 40 nm layer on the intermediate layer.

[0489] A second light-emitting layer was formed on the second hole transport layer by co-depositing 4,8mDBtP2Bfpm, βNCCP, and Ir(ppy)2(mbfpypy-d3) at a weight ratio of 0.5:0.5:0.1 (=4,8mDBtP2Bfpm:βNCCP:Ir(ppy)2(mbfpypy-d3)) at a thickness of 40 nm.

[0490] Subsequently, 2mPCCzPDBq was deposited to a thickness of 20 nm, and then mPPhen2P was deposited to a thickness of 20 nm to form a second electron transport layer.

[0491] Then, under vacuum (approximately 1 x 10⁻⁶) -4 At Pa, lithium fluoride (LiF) and ytterbium (Yb) were co-deposited at a volume ratio of 2:1 (=LiF:Yb) to a thickness of 1.5 nm. Subsequently, silver (Ag) and magnesium (Mg) were co-deposited at a volume ratio of 1:0.1 to a thickness of 15 nm to form a second electrode 102, thereby fabricating a light-emitting device according to one embodiment of the present invention. Furthermore, a 70 nm film of 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviated as DBT3P-II), represented by the above structural formula (ix), was deposited on the second electrode 102 as a cap layer to improve the light extraction efficiency.

[0492] 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 3.

[0493] (Method for fabricating comparative light-emitting device 2) Comparative light-emitting device 2 was fabricated in the same manner as light-emitting device 3, except that 2,9hpp2Phen in light-emitting device 3 was replaced with 1,1'-pyridine-2,6-diyl-bis(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine) (abbreviated as hpp2Py), represented by the above structural formula (xi).

[0494] The device structures of light-emitting device 3 and comparative light-emitting device 2 are shown below.

[0495] [Table 3]

[0496] Figure 25 shows the luminance-current density characteristics of light-emitting device 3 and comparative light-emitting device 2, Figure 26 shows the luminance-voltage characteristics, Figure 27 shows the current efficiency-luminance characteristics, Figure 28 shows the current-voltage characteristics, and Figure 29 shows the emission spectra. 2 Table 4 shows the main characteristics of the vicinity. Luminance, CIE chromaticity, and emission spectrum were measured using a spectroradiometer (Topcon SR-UL1R) at room temperature.

[0497] [Table 4]

[0498] As shown in Figures 25 to 29, the light-emitting device 3 was found to be a light-emitting device with good current efficiency, especially in the low-brightness region, and also a light-emitting device with a low driving voltage. This is thought to be because the LUMO level of 2,9hpp2Phen is lower than that of hpp2Py, resulting in good electron injection and transport properties.

[0499] Next, a current density of 50 mA / cm². 2 Figure 30 shows the results of measuring the change in brightness with respect to the operating time during constant current drive. From Figure 30, it can be seen that the light-emitting device 3 is a light-emitting device with better characteristics, including a longer lifespan, than the comparative light-emitting device 2. [Examples]

[0500] <<Synthesis Example 1>> In this example, the synthesis method of 2,9-bis(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine-1-yl)-1,10-phenanthroline (abbreviated as 2,9hpp2Phen), which was shown as structural formula (100) in Embodiment 1, will be specifically described. The structure of 2,9hpp2Phen is shown below.

[0501] [ka]

[0502] <Synthesis of 2,9-bis(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine-1-yl)-1,10-phenanthroline (abbreviation: 2,9hpp2Phen)> 6.3 g (19 mmol) of 2,9-dibromo-1,10-phenanthroline, 5.7 g (41 mmol) of 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine, 12.6 g (112 mmol) of potassium tert-butoxide, and 93 mL of toluene were placed in a 200 mL three-necked flask and degassed by stirring under reduced pressure. After stirring this mixture at 60°C, 0.43 g (1.9 mmol) of palladium(II) acetate (abbreviation: Pd(OAc)2) and 2.3 g (3.7 mmol) of 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (abbreviation: rac-BINAP) were added, and the mixture was stirred at 90°C for 4 hours. After the specified time, 50 mL of tetrahydrofuran was added to the resulting mixture, and it was filtered by suction. The obtained filtrate was concentrated to obtain a brown oily substance. Methanol was added to the oily substance, and the mixture was filtered by suction to remove insoluble matter. After concentrating the obtained filtrate, ethyl acetate was added, and the mixture was filtered by suction to obtain 3.8 g of brown solid. 400 mL of toluene was added to 2.1 g of the obtained solid and the mixture was heated. The heated solution was filtered while hot to remove insoluble matter. The obtained filtrate was concentrated to obtain a solid. Ethyl acetate was added to the obtained solid and the mixture was filtered by suction to obtain 0.75 g of yellow solid in a yield of 9%. 0.73 g of the obtained solid was purified by sublimation using the train sublimation method. This was carried out by heating at 235°C for 15.5 hours under conditions of a pressure of 4.6 Pa and an argon flow rate of 10 mL / min. After sublimation purification, 0.16 g of yellow solid was obtained with a recovery rate of 27%. The synthesis scheme is shown below.

[0503] [ka]

[0504] Furthermore, the protons of the yellow solid obtained by the above scheme ( 1 H) was measured by nuclear magnetic resonance (NMR). The obtained values ​​are shown below. 1 The 1H NMR chart is shown in Figure 31. From this, it can be seen that in this synthesis example, 2,9hpp2Phen, which is one embodiment of the present invention represented by the above-mentioned structural formula (100), was obtained.

[0505] 1 H NMR.δ(CDCl3,500MHz):1.90-1.95(m,4H),2.10-2.15(m,4H),3.24-3.30(m,8H),3.46(t,J=5. 73Hz,4H),4.34(t,J=5.73Hz,4H),7.49(s,2H),7.91(d,J=9.16Hz,2H),8.02(d,J=8.59Hz,2H).

[0506] The glass transition temperature (Tg) of 2,9hpp2Phen was measured. Tg was measured using a differential scanning calorimetry system (DSC8500, PerkinElmer Japan Co., Ltd.) by placing the powder in an aluminum cell and heating it at a rate of 40°C / min. As a result, the Tg of 2,9hpp2Phen was found to be 87°C.

[0507] Next, we present the results of a calculation that verified the solubility of 2,9hpp2Phen in water.

[0508] For the calculations, we used Desmond as the classical molecular dynamics software. OPLS2005 was used for the force field. The calculations were performed on a high-performance computer (HPE Apollo 6500).

[0509] The computational model used a reference cell containing approximately 32 molecules. For each material, the initial molecular structure was determined by mixing multiple structures with energies close to the most stable (singlet ground state) obtained from first-principles calculations in roughly equal proportions, and arranging them randomly to prevent molecular collisions. Subsequently, the structures were randomly moved and rotated using Monte Carlo simulated annealing with OPLS2005 as the force field, thereby moving the molecules. Furthermore, the molecules were moved towards the center of the reference cell to maximize density, resulting in the initial configuration.

[0510] For the first-principles calculations described above, the Jaguar quantum chemistry software was used to calculate the most stable structure in the singlet ground state using density functional theory (DFT). The basis set used was 6-31G**, and the functional was B3LYP-D3. The structures used for the quantum chemistry calculations were sampled by performing conformational analysis using mixed torsional / low-mode sampling with the Maestro GUI from Schrödinger. The calculations were performed on a high-performance computer (HPE Apollo 6500).

[0511] The initial configuration described above was simulated using Brownian motion, followed by an NVT ensemble. The ensemble was then treated as an NPT, and calculations were performed with a sufficient relaxation time (30 ns) under conditions of 1 atm and 300 K for a step time (2 fs) that reproduces molecular vibrations, thereby calculating the amorphous solid.

[0512] The solubility parameter δ of the obtained amorphous solid is defined as follows: δ = [(ΔHv - RT) / Vm] 1 / 2

[0513] Here, ΔHv represents the heat of vaporization, obtained by subtracting the total energy of individual molecules averaged across the entire molecular dynamics calculation from the energy of the reference cell; Vm represents the molar volume; R represents the gas constant; and T represents the temperature. The calculation results for each material were analyzed, and a polarization term δp was obtained by decomposing the electrostatic contribution for the solubility parameter.

[0514] As a result, the δp value for 2,9hpp2Phen was 9.1, and the δp value for hpp2py was 9.4.

[0515] Regarding the solubility parameter in water, the measured value δp, which corresponds to the polarization term, is disclosed as 16.0 in, for example, Japanese Patent Application Publication No. 2017-173056. Since a larger absolute value of the difference in the solubility parameter indicates that it is less soluble, it was found that 2,9hpp2Phen is less soluble in water than hpp2py.

[0516] Furthermore, the electrochemical properties (oxidation and reduction reaction properties) of 2,9hpp2Phen were measured by cyclic voltammetry (CV). For the measurement, an electrochemical analyzer (ALS Model 600A, manufactured by BAS Corporation) was used, and dehydrated N,N-dimethylformamide (DMF) (manufactured by Aldrich Corporation, 99.8%, catalog number: 22705-6) was used as the solvent. Tetra-n-butylammonium perchlorate (n-Bu4NClO4) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836), which is the supporting electrolyte, was dissolved to a concentration of 100 mmol / L, and the target substance was further dissolved to a concentration of 2 mmol / L to prepare the solution.

[0517] Furthermore, a platinum electrode (PTE platinum electrode manufactured by BAS Corporation) was used as the working electrode, a platinum electrode (Pt counter electrode (5cm) manufactured by BAS Corporation) was used as the auxiliary electrode, and Ag / Ag was used as the reference electrode. + Electrodes (RE7 non-aqueous solvent reference electrode, manufactured by BAS Corporation) were used for each measurement. The measurements were performed at room temperature (20°C to 25°C).

[0518] Furthermore, the scan speed during CV measurement was standardized to 0.1 V / sec, and the oxidation potential Ea [V] and reduction potential Ec [V] with respect to the reference electrode were measured. Ea was defined as the intermediate potential of the oxidation-reduction wave, and Ec was defined as the intermediate potential of the reduction-oxidation wave. Here, since the potential energy of the reference electrode used in this embodiment with respect to the vacuum level is known to be -4.94 [eV], the HOMO level [eV] = -4.94 - Ea and the LUMO level [eV] = -4.94 - Ec can be used to determine the HOMO level and LUMO level, respectively.

[0519] Furthermore, CV measurements were repeated 100 times, and the oxidation-reduction wave at the 100th cycle was compared with the oxidation-reduction wave at the 1st cycle to investigate the electrical stability of the compound.

[0520] As a result of measuring the oxidation potential Ea [V] of 2,9hpp2Phen, it was found that the HOMO level is around -5.6 eV. On the other hand, from the measurement of the reduction potential Ec [V], it was found that the LUMO level is -2.3 eV. Since the HOMO level of hpp2Py is around -5.3 eV and the LUMO level is around -2.1 eV, it was found that 2,9hpp2Phen has deeper HOMO and LUMO levels than hpp2Py. [Examples]

[0521] ≪Synthesis Example 2≫ In this example, the synthesis method of 4,7-bis(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine-1-yl)-1,10-phenanthroline (abbreviated as 4,7hpp2Phen), which was shown as structural formula (101) in Embodiment 1, will be specifically described. The structure of 4,7hpp2Phen is shown below.

[0522] [ka]

[0523] <Synthesis of 4,7-bis(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine-1-yl)-1,10-phenanthroline (abbreviation: 4,7hpp2Phen)> 5.5 g (16 mmol) of 4,7-dibromo-1,10-phenanthroline, 5.0 g (36 mmol) of 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine, 11 g (98 mmol) of potassium tert-butoxide, and 81 mL of toluene were placed in a 200 mL three-necked flask and degassed by stirring under reduced pressure. After stirring this mixture at 60°C, 0.37 g (1.7 mmol) of palladium(II) acetate (abbreviation: Pd(OAc)2) and 2.0 g (3.2 mmol) of 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (abbreviation: rac-BINAP) were added, and the mixture was stirred at 90°C for 5 hours. After the specified time, 50 mL of tetrahydrofuran was added to the resulting mixture, and it was filtered by suction. The resulting filtrate was concentrated to obtain a brown oily substance. Ethyl acetate was added to the obtained oily substance, and the mixture was filtered by suction to obtain a solid. Methanol was added to the solid, and the mixture was filtered by suction to remove insoluble matter. The obtained filtrate was concentrated, and ethyl acetate was added, and the mixture was filtered by suction to obtain a brown solid. 1.5 g of the obtained solid was added to 600 mL of toluene and heated. The heated solution was filtered while hot to remove insoluble matter. The obtained filtrate was concentrated to obtain a solid. Ethyl acetate was added to the obtained solid, and the mixture was filtered by suction to obtain 0.92 g of a yellow solid in a yield of 12%.

[0524] The obtained solid (0.88 g) was purified by sublimation using the train sublimation method. Pressure: 1.9 × 10⁻⁶ -3 The yellow solid was heated at 260°C for 23 hours under Pa conditions. After sublimation purification, 39 mg of the target product was obtained with a recovery rate of 5%. The synthesis scheme is shown below.

[0525] [ka]

[0526] Furthermore, the protons of the yellow solid obtained by the above scheme ( 1 H) was measured by nuclear magnetic resonance (NMR). The obtained values ​​are shown below. 1The 1H NMR chart is shown in Figure 32. From this, it can be seen that in this synthesis example, 4,7hpp2Phen, which is one embodiment of the present invention represented by the above-mentioned structural formula (101), was obtained.

[0527] 1 H NMR.δ(CDCl3,500MHz):1.86-1.91(m,4H),2.21(s,4H),3.21(t,J=5.73Hz,4H),3.28(t,J=5.73Hz,4 H),3.36(t,J=6.30Hz,4H),3.66(s,4H),7.37(d,J=5.15Hz,2H),7.81(s,2H),9.06(d,J=5.15Hz,2H).

[0528] Next, we present the results of a calculation verifying the solubility of 4,7hpp2Phen in water. The calculation was performed in the same manner as described in Example 1.

[0529] As a result, the δp for 4,7hpp2Phen was 8.6, and the δp for hpp2py was 9.4.

[0530] Regarding the solubility parameter in water, the measured value δp, which corresponds to the polarization term, is disclosed as 16.0 in, for example, Japanese Patent Application Publication No. 2017-173056. Since a larger absolute value of the difference in the solubility parameter indicates that it is less soluble, it was found that 4,7hpp2Phen is less soluble in water than hpp2py.

[0531] Furthermore, the electrochemical properties (oxidation and reduction reaction properties) of 4,7hpp2Phen were measured by cyclic voltammetry (CV). For the measurement, an electrochemical analyzer (ALS Model 600A, manufactured by BAS Corporation) was used, and dehydrated N,N-dimethylformamide (DMF) (manufactured by Aldrich Corporation, 99.8%, catalog number: 22705-6) was used as the solvent. Tetra-n-butylammonium perchlorate (n-Bu4NClO4) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836), which is the supporting electrolyte, was dissolved to a concentration of 100 mmol / L, and the target substance was further dissolved to a concentration of 2 mmol / L to prepare the solution.

[0532] Furthermore, a platinum electrode (PTE platinum electrode manufactured by BAS Corporation) was used as the working electrode, a platinum electrode (Pt counter electrode (5cm) manufactured by BAS Corporation) was used as the auxiliary electrode, and Ag / Ag was used as the reference electrode. + Electrodes (RE7 non-aqueous solvent reference electrode, manufactured by BAS Corporation) were used for each measurement. The measurements were performed at room temperature (20°C to 25°C).

[0533] Furthermore, the scan speed during CV measurement was standardized to 0.1 V / sec, and the oxidation potential Ea [V] and reduction potential Ec [V] with respect to the reference electrode were measured. Ea was defined as the intermediate potential of the oxidation-reduction wave, and Ec was defined as the intermediate potential of the reduction-oxidation wave. Here, since the potential energy of the reference electrode used in this embodiment with respect to the vacuum level is known to be -4.94 [eV], the HOMO level [eV] = -4.94 - Ea and the LUMO level [eV] = -4.94 - Ec can be used to determine the HOMO level and LUMO level, respectively.

[0534] Furthermore, CV measurements were repeated 100 times, and the oxidation-reduction wave at the 100th cycle was compared with the oxidation-reduction wave at the 1st cycle to investigate the electrical stability of the compound.

[0535] As a result of measuring the oxidation potential Ea [V] of 4,7hpp2Phen, it was found that the HOMO level is around -5.6 eV. On the other hand, from the measurement of the reduction potential Ec [V], it was found that the LUMO level is -2.5 eV. Since the HOMO level of hpp2Py is around -5.3 eV and the LUMO level is around -2.1 eV, it was found that 4,7hpp2Phen has deeper HOMO and LUMO levels than hpp2Py. [Examples]

[0536] ≪Synthesis Example 3≫ In this example, the synthesis method of 2-(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine-1-yl)-9-phenyl-1,10-phenanthroline (abbreviated as 9Ph-2hppPhen), shown as structural formula (102) in Embodiment 1, will be specifically described. The structure of 9Ph-2hppPhen is shown below.

[0537] [ka]

[0538] <Synthesis of 2-(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine-1-yl)-9-phenyl-1,10-phenanthroline (abbreviation: 9Ph-2hppPhen)> 6.1 g (21 mmol) of 2-chloro-9-phenyl-1,10-phenanthroline, 6.7 g (48 mmol) of 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine, and 100 mL of toluene were placed in a 200 mL three-necked flask and stirred at 100 °C under a nitrogen atmosphere for 11 hours.

[0539] After a predetermined time, the reaction solution was concentrated, methanol was added to the solid, and the mixture was filtered by suction to remove insoluble matter. The resulting filtrate was concentrated, and toluene was added and heated. The heated solution was filtered while hot to remove insoluble matter. The resulting filtrate was concentrated to obtain a solid. Ethyl acetate was added to the obtained solid and filtered by suction to obtain 5.3 g of a yellowish-white solid in 64% yield. 5.0 g of the obtained solid was purified by sublimation using the train sublimation method. This was carried out by heating at 220°C for 18 hours under conditions of a pressure of 3.0 Pa and an argon flow rate of 12 mL / min. After sublimation purification, 2.54 g of a yellowish-white solid was obtained in 51% recovery. The synthesis scheme is shown below.

[0540] [ka]

[0541] Furthermore, the protons of the yellowish-white solid obtained by the above scheme ( 1 H) was measured by nuclear magnetic resonance (NMR). The obtained values ​​are shown below. 1 The 1H NMR chart is shown in Figure 33. From this, it can be seen that in this synthesis example, 9Ph-2hppPhen, which is one embodiment of the present invention represented by the above-mentioned structural formula (102), was obtained.

[0542] 1 H NMR.δ(CDCl3,500MHz):1.92-1.96(m,2H),2.16-2.21(m,2H),3.28-3.32(m,4H),3.49 (t,J=5.73Hz,2H),4.34(t,J=5.73Hz,2H),7.46(t,J=7.45Hz,1H),7.55(d,J=7.45Hz, 2H),7.61(d,J=8.59Hz,1H),7.68(d,J=8.59Hz,1H),7.97(d,J=9.16Hz,1H),8.06(d,J =8.02Hz,1H),8.17(d,J=9.16Hz,1H),8.25(d,J=8.02Hz,1H),8.39(d,J=6.87Hz,2H).

[0543] The glass transition temperature (Tg) of 9Ph-2hppPhen was measured. Tg was measured using a differential scanning calorimetry system (DSC8500, PerkinElmer Japan Co., Ltd.) by placing the powder in an aluminum cell and heating it at a rate of 40°C / min. As a result, the Tg of 9Ph-2hppPhen was found to be 71°C.

[0544] Furthermore, the electrochemical properties (oxidation and reduction reaction properties) of 9Ph-2hppPhen were measured by cyclic voltammetry (CV). For the measurement, an electrochemical analyzer (ALS Model 600A, manufactured by BAS Corporation) was used, and dehydrated N,N-dimethylformamide (DMF) (manufactured by Aldrich Corporation, 99.8%, catalog number: 22705-6) was used as the solvent. Tetra-n-butylammonium perchlorate (n-Bu4NClO4) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836), which is the supporting electrolyte, was dissolved to a concentration of 100 mmol / L, and the target substance was further dissolved to a concentration of 2 mmol / L to prepare the solution.

[0545] Furthermore, a platinum electrode (PTE platinum electrode manufactured by BAS Corporation) was used as the working electrode, a platinum electrode (Pt counter electrode (5cm) manufactured by BAS Corporation) was used as the auxiliary electrode, and Ag / Ag was used as the reference electrode. + Electrodes (RE7 non-aqueous solvent reference electrode, manufactured by BAS Corporation) were used for each measurement. The measurements were performed at room temperature (20°C to 25°C).

[0546] Furthermore, the scan speed during CV measurement was standardized to 0.1 V / sec, and the oxidation potential Ea [V] and reduction potential Ec [V] with respect to the reference electrode were measured. Ea was defined as the intermediate potential of the oxidation-reduction wave, and Ec was defined as the intermediate potential of the reduction-oxidation wave. Here, since the potential energy of the reference electrode used in this embodiment with respect to the vacuum level is known to be -4.94 [eV], the HOMO level [eV] = -4.94 - Ea and the LUMO level [eV] = -4.94 - Ec can be used to determine the HOMO level and LUMO level, respectively.

[0547] Furthermore, CV measurements were repeated 100 times, and the oxidation-reduction wave at the 100th cycle was compared with the oxidation-reduction wave at the 1st cycle to investigate the electrical stability of the compound.

[0548] As a result of measuring the oxidation potential Ea [V] of 9Ph-2hppPhen, it was found that the HOMO level is around -5.5 eV. On the other hand, from the measurement of the reduction potential Ec [V], it was found that the LUMO level is -2.6 eV. Since the HOMO level of hpp2Py is around -5.3 eV and the LUMO level is around -2.1 eV, it was found that 9Ph-2hppPhen has deeper HOMO and LUMO levels than hpp2Py. [Examples]

[0549] <<Synthesis Example 4>> In this example, we will specifically describe the synthesis method of 2,2'-(1,3-phenylene)bis[9-(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine-1-yl)-1,10-phenanthroline] (abbreviated as mhppPhen2P), which was shown as structural formula (113) in Embodiment 1. The structure of mhppPhen2P is shown below.

[0550] [ka]

[0551] <Step 1: Synthesis of 9,9'-(1,3-phenylene)bis[2-bromo-1,10-phenanthroline]> 16.7 g (49 mmol) of 2,9-dibromo-1,10-phenanthroline, 5.4 g (17 mmol) of 1,3-bis(pinacol) benzenediboronic acid, 49 mL of 2M potassium carbonate aqueous solution, 66 mL of toluene, and 16 mL of ethanol were placed in a 200 mL three-necked flask, and the mixture was degassed by stirring under reduced pressure. After stirring this mixture at 60°C, 3.1 g (3 mmol) of tetrakis(triphenylphosphine)palladium(0) (abbreviation: Pd(PPh3)4) was added, and the mixture was stirred at 90°C for 10 hours.

[0552] After a predetermined time, the reaction solution was filtered by suction, and the solid was washed with water and ethanol. The resulting filtrate was heated in toluene to dissolve it, filtered through a filtration aid consisting of layers of Celite, alumina, and Celite, and the filtrate was concentrated to obtain a solid. The obtained solid was purified by silica gel column chromatography (toluene-toluene:ethyl acetate = 3:1). The obtained solid was recrystallized in toluene to obtain 2.6 g of a white solid in a yield of 27%. The synthesis scheme for Step 1 is shown below.

[0553] [ka]

[0554] <Step 2: Synthesis of 2,2'-(1,3-phenylene)bis[9-(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine-1-yl)-1,10-phenanthroline] (abbreviation: mhppPhen2P)> 2.6 g (4 mmol) of 9,9'-(1,3-phenylene)bis[2-bromo-1,10-phenanthroline] synthesized in Step 1, 1.4 g (10 mmol) of 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine, and 25 mL of toluene were placed in a 200 mL three-necked flask, and the mixture was degassed by stirring under reduced pressure. After stirring this mixture at 60°C, 0.1 g (0.3 mmol) of palladium(II) acetate (abbreviation: Pd(OAc)2) and 0.3 g (0.5 mmol) of 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (abbreviation: rac-BINAP) were added, and the mixture was stirred at 90°C for 4 hours.

[0555] After a predetermined time, methanol was added to the resulting mixture, and the mixture was filtered by suction to remove insoluble matter. The obtained filtrate was concentrated, ethyl acetate was added, and the mixture was filtered by suction to obtain 7.2 g of a brown oily substance. 200 mL of toluene was added to the obtained brown oily substance and it was heated. The heated solution was filtered while hot to remove insoluble matter. The obtained filtrate was concentrated to obtain a solid. Ethyl acetate was added to the obtained solid and the mixture was filtered by suction to obtain 1.6 g of a yellow solid in a yield of 52%. The synthesis scheme for Step 2 is shown below.

[0556] [ka]

[0557] Furthermore, the protons of the yellow solid obtained by the above scheme ( 1 H) was measured by nuclear magnetic resonance (NMR). The obtained values ​​are shown below. 1 The 1H NMR chart is shown in Figure 34. From this, it can be seen that in this synthesis example, mhppPhen2P, which is one embodiment of the present invention represented by the above-mentioned structural formula (113), was obtained.

[0558] 1 H NMR.δ(CDCl3,500MHz):1.92-1.97(m,4H),2.12-2.18(m,4H),3.27-3.33(m,8H),3. 49(t,J=5.73Hz,4H),4.55(t,J=6.30Hz,4H),7.65(d,J=8.59Hz,2H),7.70(d,J=8.59 Hz,2H),7.74(t,J=8.02Hz,1H),8.00(d,J=9.16Hz,2H),8.19(d,J=8.59Hz,2H),8.2 9(sd,J=2.29Hz,4H),8.57(dd,J1=8.02Hz,J2=1.72Hz,2H),9.54(ts,J=1.72Hz,1H). [Examples]

[0559] In this example, the detailed manufacturing method and characteristics of a light-emitting device 4 according to one embodiment of the present invention will be described. The structural formulas of the main compounds used in this example are shown below.

[0560] [ka]

[0561] (Method for fabricating light-emitting device 4) First, a 100 nm layer of silver (Ag) was sequentially layered on a glass substrate using a sputtering method, and a 10 nm layer of indium tin oxide (ITSO) containing silicon dioxide was sequentially layered on the glass substrate using a sputtering method to form a first electrode 101 measuring 2 mm x 2 mm. The transparent electrode functions as an anode and, together with the reflective electrode, is considered to be part of the first electrode 101.

[0562] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water, baked at 200°C for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

[0563] After that, approximately 1 × 10 -4 The substrate was introduced into a vacuum deposition apparatus where the internal pressure was reduced to Pa. After vacuum firing at 170°C for 60 minutes in the heating chamber of the vacuum deposition apparatus, the substrate was allowed to cool for approximately 30 minutes.

[0564] Next, the substrate was fixed to a holder provided in the vacuum deposition apparatus so that the surface on which the first electrode 101 was formed was facing downwards. On the first electrode 101, a hole injection layer 111 was formed by co-depositing 10 nm of N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviated as PCBBiF), represented by the above structural formula (i), and an electron acceptor material (OCHD-003) containing fluorine with a molecular weight of 672, in a weight ratio of 1:0.03 (=PCBBiF:OCHD-003).

[0565] A 20 nm layer of PCBBiF was deposited on the hole injection layer 111 to form a first hole transport layer.

[0566] Next, on the first hole transport layer, 8-(1,1':4',1''-terphenyl-3-yl)-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzoflo[3,2-d]pyrimidine (abbreviation: 8mpTP-4mDBtPBfpm) represented by the above structural formula (xii), 9-(2-naphthyl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: βNCCP) represented by the above structural formula (xiii), and [2- A first light-emitting layer was formed by co-depositing d3-methyl-8-(2-pyridinyl-κN)benzofl[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridinyl-κN2)phenyl-κC]iridium(III) (abbreviation: Ir(5mppy-d3)2(mbfpypy-d3)) at a weight ratio of 0.5:0.5:0.1 (=8mpTP-4mDBtPBfpm:βNCCP:Ir(5mppy-d3)2(mbfpypy-d3)) at a thickness of 40 nm.

[0567] Subsequently, 2-{3-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-9-yl]phenyl}dibenzo[f,h]quinoxaline (abbreviation: 2mPCCzPDBq), represented by the above structural formula (v), was deposited to a thickness of 10 nm to form the first electron transport layer.

[0568] After the formation of the first electron transport layer, 2,2'-(1,3-phenylene)bis(9-phenyl-1,10-phenanthroline) (abbreviation: mPPhen2P) represented by the above structural formula (vi) and 2-(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine-1-yl)-9-phenyl-1,10-phenanthroline (abbreviation: 9Ph-2hppP) represented by the above structural formula (xiv) are formed. After co-depositing 5 nm of hen in a weight ratio of 0.5:0.5 (= mPPhen2P:9Ph-2hppPhen), copper phthalocyanine (abbreviated as CuPc) represented by the above structural formula (viii) was deposited to a thickness of 2 nm, and then PCBBiF and OCHD-003 were co-deposited at a weight ratio of 1:0.15 (= PCBBiF:OCHD-003) to form an intermediate layer at a thickness of 10 nm.

[0569] A second hole transport layer was formed by depositing PCBBiF at a 65 nm layer on the intermediate layer.

[0570] A second light-emitting layer was formed on the second hole transport layer by co-depositing 8mpTP-4mDBtPBfpm, βNCCP, and Ir(5mppy-d3)2(mbfpypy-d3) at a weight ratio of 0.5:0.5:0.1 (=8mpTP-4mDBtPBfpm:βNCCP:Ir(5mppy-d3)2(mbfpypy-d3)) at a thickness of 40 nm to form a second light-emitting layer.

[0571] Subsequently, 2mPCCzPDBq was deposited to a thickness of 20 nm, and then mPPhen2P was deposited to a thickness of 20 nm to form a second electron transport layer.

[0572] After that, under vacuum (approximately 1 × 10⁻⁶ -4 At Pa, lithium fluoride (LiF) and ytterbium (Yb) were co-deposited at a volume ratio of 2:1 (=LiF:Yb) to a thickness of 1.5 nm, and then silver (Ag) and magnesium (Mg) were co-deposited at a volume ratio of 1:0.1 to a thickness of 15 nm to form the second electrode 102. Furthermore, a 70 nm film of 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), represented by the above structural formula (ix), was deposited on the second electrode 102 as a cap layer to improve the light extraction efficiency.

[0573] 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 4.

[0574] The device structure of the light-emitting device 4 is shown below.

[0575] [Table 5]

[0576] Figure 35 shows the luminance-current density characteristics of the light-emitting device 4, Figure 36 shows the luminance-voltage characteristics, Figure 37 shows the current efficiency-luminance characteristics, Figure 38 shows the current-voltage characteristics, and Figure 39 shows the field emission spectrum. 2 Table 6 shows the main characteristics of the vicinity. Luminance, CIE chromaticity, and emission spectrum were measured using a spectroradiometer (Topcon SR-UL1R) at room temperature.

[0577] [Table 6]

[0578] As shown in Figures 35 to 39, the light-emitting device 4 was found to be a light-emitting device with good characteristics, and in particular, a light-emitting device with good current efficiency in the low-brightness region. It was also found to be a light-emitting device with a low driving voltage.

[0579] Next, a current density of 50 mA / cm². 2 Figure 40 shows the results of measuring the change in brightness with respect to the operating time during constant current drive. From Figure 40, it was found that the light-emitting device 4 is a light-emitting device with good characteristics and a long lifespan. [Explanation of Symbols]

[0580] 100A display device 100B display device 100C display device 100E display device 100D display device 100 Insulator 101a First electrode 101b First electrode 101c First electrode 101d First electrode 101 First electrode 102 Second electrode 103a Organic compound layer 103B Organic compound layer 103b Organic compound layer 103Bf Organic compound film 103c Organic compound layer 103d Organic compound layer 103G organic compound layer 103Gf organic compound film 103R Organic compound layer 103Rf Organic compound film 103 Organic compound layer 104 The first layer 104R Layer 1 104G Layer 1 104B Layer 1 105 The second layer 110B subpixel 110G sub-pixels 110R sub-pixel 110 subpixels 111a Hole injection layer 111b Hole injection layer 111c Hole injection layer 111d Hole injection layer 111 Hole injection layer 112 Hole transport layer 112a Hole transport layer 112b Hole transport layer 112c_1 Hole transport layer 112c_2 Hole transport layer 112d_1 Hole transport layer 112d_2 Hole transport layer 112R conductive layer 112B Conductive layer 113 Emitting layer 113a Light-emitting layer 113b Emitting layer 113c_1 Emitting layer 113c_2 Emitting layer 113d_1 Emitting layer 113d_2 Emitting layer 114 Electron transport layer 114a Electron transport layer 114b Electron transport layer 114c_1 Electron transport layer 114c_2 Electron transport layer 114d_1 Electron transport layer 114d_2 Electron transport layer 115 Electron injection layer 116 Charge generation layer 116c middle class 116d middle class 117 P type layer 117c P type layer 117d P type layer 118 Electron relay layer 118c Electron Relay Layer 118d Electron relay layer 119 N-type layer 119c N-type layer 119d N-type layer 120 circuit boards 122 Resin layer 125f inorganic insulating film 125 Inorganic insulating layer 126R conductive layer 126B Conductive layer 127a Insulating layer 127f insulating film 127 Insulating layer 128 layers 129R conductive layer 129B Conductive layer 130a Light-emitting device 130B Light-emitting device 130b Light-emitting device 130c light-emitting device 130d light-emitting device 130G Light-emitting Device 130R Light-emitting Device 130 Light-emitting devices 131 Protective layer 132B Colored layer 132G colored layer 132R colored layer 140 Connection part 141 areas 142 Adhesive layer 151B Conductive layer 151C conductive layer 151cf conductive film 151f Conductive film 151G conductive layer 151R conductive layer 151 Conductive layer 152B Conductive layer 152C conductive layer 152f Conductive film 152G conductive layer 152R conductive layer 152 Conductive layer 153 Insulating layer 155 Common electrode 156B Insulating layer 156C insulating layer 156f insulating film 156G insulating layer 156R Insulating Layer 156 Insulating layer 157 Light blocking layer 158B Sacrifice Layer 158Bf sacrificial membrane 158G Sacrifice Layer 158Gf sacrificial membrane 158R Sacrifice Layer 158Rf sacrificial membrane 159B Mask layer 159Bf mask film 159G mask layer 159 Gf mask film 159R mask layer 159Rf mask membrane 166 Conductive layer 171 Insulating layer 172 Conductive layer 173 Insulating layer 174 Insulating layer 175 Insulating layer 176 plug 177 pixel section 178 pixels 179 Conductive layer 190B Resist Mask 190G Resist Mask 190R Resist Mask 191 Resist Mask 201 Transistors 204 Connection part 205 transistors 211 Insulating layer 213 Insulating layer 214 Insulating layer 215 Insulating layer 221 Conductive layer 222a conductive layer 222b Conductive layer 223 Conductive layer 224B Conductive layer 224C conductive layer 224G conductive layer 224R conductive layer 231 Semiconductor layer 240 capacity 241 Conductive layer 242 Connecting Layers 243 Insulating layer 245 Conductive layer 254 Insulating layer 255 Insulating layer 256 plug 261 Insulating layer 271 Plug 280 Display Modules 281 Display section 282 Circuit section 283a Pixel Circuit 283 Pixel Circuit Section 284a pixels 284 pixel section 285 Terminal section 286 Wiring section 290 FPC 291 circuit boards 292 circuit boards 301 circuit board 310 transistors 311 Conductive layer 312 Low resistance region 313 Insulating layer 314 Insulating layer 315 element isolation layer 351 circuit board 352 circuit boards 353 FPC 354 IC 355 Wiring 356 circuits 501 First electrode 501c First light-emitting unit 501d First light-emitting unit 502 Second electrode 502c Second light-emitting unit 502d Second light-emitting unit 511 First light-emitting unit 512 Second light-emitting unit 513 Middle Class 700A electronic equipment 700B Electronic equipment 721 cabinet 723 Mounting part 727 Earphone section 750 Earphones 751 Display Panel 753 Optical components 756 Display area 757 frames 758 Nose pads 800A electronic equipment 800B Electronic equipment 820 Display section 821 cabinet 822 Communications Department 823 Mounting part 824 Control Unit 825 Imaging Unit 827 Earphone section 832 Lens 6500 Electronic equipment 6501 enclosure 6502 Display section 6503 Power button 6504 button 6505 Speaker 6506 Mike 6507 Camera 6508 Light source 6510 Protective component 6511 Display Panel 6512 Optical components 6513 Touch Sensor Panel 6515 FPC 6516 IC 6517 Printed circuit board 6518 Battery 7000 Display 7100 Television equipment 7151 Remote Control Unit 7171 enclosure 7173 Stand 7200 Notebook Personal Computer 7211 enclosure 7212 Keyboard 7213 Pointing device 7214 External connection port 7300 Digital Signage 7301 enclosure 7303 Speaker 7311 Information terminal 7400 Digital Signage 7401 pillars 7411 Information terminal 9000 cabinets 9001 Display section 9002 Camera 9003 Speaker 9005 Operation Keys 9006 Connection terminal 9007 Sensor 9008 Microphone 9050 Icon 9051 Information 9052 Information 9053 Information 9054 Information 9055 Hinge 9171 Mobile Information Terminal 9172 Mobile Information Terminal 9173 Tablet device 9200 Mobile Information Terminal 9201 Mobile Information Terminal

Claims

1. An organic compound represented by the following general formula (G1). 【Chemistry 1】 (However, in the above general formula (G1), R １ ~R ８ Each of these is independently one of hydrogen, a C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group, a substituted or unsubstituted C2 to C30 heteroaromatic hydrocarbon group, and a group represented by the following structural formula (R-1). However, the R １ ~R ８ (The group consists of two or more groups other than hydrogen, and one to four groups represented by the following structural formula (R-1).) 【Chemistry 2】

2. In claim 1, The aforementioned R １ ~R ８ Any one of the groups is represented by the following structural formula (R-1), any one of which is an aromatic hydrocarbon group having 6 to 30 carbon atoms having a group represented by the general formula (g1), and the remaining groups are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic hydrocarbon group having 2 to 30 carbon atoms, and a group represented by the following structural formula (R-1), and the R １ ~R ８ This refers to an organic compound in which 1 to 3 of its components are groups represented by the following structural formula (R-1). 【Transformation 3】 【Chemistry 4】 (However, in the above general formula (g1), R １１ to R １８ is such that any one of them is a bond and is bonded to an aromatic hydrocarbon group having 6 to 30 carbon atoms and represented by the above general formula (g1), any one of them is a group represented by the above structural formula (R-1), and the rest are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic hydrocarbon group having 2 to 30 carbon atoms, and any one of the groups represented by the above structural formula (R-1), and R １１ to R １８ is such that 1 or more and 3 or less of them are groups represented by the above structural formula (R-1). )

3. An organic compound represented by the following general formula (G2). 【Transformation 5】 (However, in the above general formula (G2), R １ , R ３ , R ６ and R ８ Each of these is independently one of hydrogen, a C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group, a substituted or unsubstituted C2 to C30 heteroaromatic hydrocarbon group, and a group represented by the following structural formula (R-1). However, the R １ , R ３ , R ６ and R ８ (The group consists of two or more groups other than hydrogen, and one to four groups represented by the following structural formula (R-1).) 【Transformation 6】

4. In claim 3, The aforementioned R １ , R ３ , R ６ and R ８ In this, one of the groups is represented by the following structural formula (R-1), one of which is a substituted aromatic hydrocarbon group having 6 to 30 carbon atoms, and the rest are all hydrogen atoms. An organic compound in which the substituent on the C6 to C30 aromatic hydrocarbon group having the substituent is a group represented by the following general formula (g2). 【Transformation 7】 【Transformation 8】 (However, in the above general formula (g2), R １１ , R １３ , R １６ and R １８ One of these is a bonding site, bonded to an aromatic hydrocarbon group having 6 to 30 carbon atoms and the substituent, with one of them being the group represented by the above structural formula (R-1), and the rest being hydrogen.

5. An organic compound represented by the following general formula (G3). 【Chemistry 9】 (However, in the above general formula (G3), R １ and R ８ (One or both of these groups are represented by the following structural formula (R-1), and the remaining group is one of the following: an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic hydrocarbon group having 2 to 30 carbon atoms.) 【Chemistry 10】

6. In claim 5, The aforementioned R １ This is the group represented by the following structural formula (R-1), R ８ is an aromatic hydrocarbon group having 6 to 30 carbon atoms and having substituents, An organic compound in which the substituent on the C6 to C30 aromatic hydrocarbon group having the substituent is a group represented by the following general formula (g3). 【Chemistry 11】 【Chemistry 12】 (However, in the above general formula (g3), R １１ R is a bonding site and is bonded to an aromatic hydrocarbon group having 6 to 30 carbon atoms and the substituent, １８ This is the group represented by the above structural formula (R-1).

7. An organic compound represented by the following general formula (G4). 【Chemistry 13】 (However, in the above general formula (G4), R ３ and R ６ (One or both of these groups are represented by the following structural formula (R-1), and the remaining group is one of the following: an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic hydrocarbon group having 2 to 30 carbon atoms.) 【Chemistry 14】

8. In claim 7, The aforementioned R ３ This is the group represented by the following structural formula (R-1), R ６ is an aromatic hydrocarbon group having 6 to 30 carbon atoms and having substituents, An organic compound in which the substituent on the C6 to C30 aromatic hydrocarbon group having the substituent is a group represented by the following general formula (g4). 【Chemistry 15】 【Chemistry 16】 (However, in the above general formula (g4), R １３ R is a bonding site and is bonded to an aromatic hydrocarbon group having 6 to 30 carbon atoms and the substituent, １６ This is the group represented by the above structural formula (R-1).

9. In any one of claims 1 to 8, An organic compound having a glass transition temperature of 70°C or higher.

10. A light-emitting device having an organic compound according to any one of claims 1 to 8.

11. It comprises a first electrode, a second electrode, a first light-emitting unit, an intermediate layer, and a second light-emitting unit. The first light-emitting unit is located between the first electrode and the intermediate layer, The second light-emitting unit is located between the intermediate layer and the second electrode, The intermediate layer is a light-emitting device having an organic compound according to any one of claims 1 to 8.

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