Organic compound, organic semiconductor device and light-emitting device

Abstract

An organic compound with high heat resistance is provided. The organic compound is represented by the general formula (G1). In the general formula (G1), α represents 1 represents a substituted or unsubstituted phenylene group; n is 1 or 2; α 2 represents a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group; m is 0, 1, or 2; Ar 2 represents a group defined by the general formula (Ar 2 -a) or the general formula (Ar 2 -b) is represented; one of R 8 until \R 17 represents a bond; and X represents oxygen or sulfur.

Description

Background of the invention 1. Field of the invention

[0001] One embodiment of the present invention relates to an organic compound, an organic semiconductor device, a light-emitting device, a photoelectric conversion device, a light-emitting device, a light-receiving device, a display device, an electronic device, a lighting device, and an electronic device. It should be noted that one embodiment of the present invention is not limited to the foregoing technical field. The technical field of one embodiment of the invention disclosed in this description and the like relates to an object, a process, or a manufacturing process. One embodiment of the present invention relates to a process, a machine, a product, or a composition.Specific examples for the technical field of an embodiment of the present invention disclosed in this description include a semiconductor device, a display device, a liquid crystal display device, a light-emitting device, a lighting device, an energy storage device, a storage device, an imaging device, an operating method therefor, and a manufacturing method therefor. 2. Description of the state of the art

[0002] In recent years, organic semiconductor devices are expected to find diverse applications. Specific examples of organic semiconductor devices include light-emitting devices, such as organic light-emitting diodes (OLEDs), photoelectric conversion devices, such as organic optical sensors or organic thin-film solar cells, and organic field-effect transistors. Among these, light-emitting devices that utilize electroluminescence (hereinafter referred to as EL) exhibit features such as ease of reduction in thickness and weight, high response speed to input signals, and drive capability with a constant DC voltage current source, and are therefore used in display devices.

[0003] Improving the device properties of organic semiconductor devices involves many challenges that depend on the substance incorporated within the device, such as an organic compound, a metal, or a metal compound. To address these challenges, improvements to the device structure, the development of new substances, and similar measures have been undertaken. For example, Patent Document 1 discloses a hole transport material, which is a type of organic compound, that can increase the emission efficiency of a light-emitting device, which is a type of organic semiconductor device, when the organic compound is used in the light-emitting device. [Reference]

[0004] [Patent Document 1] Japanese Patent Publication No. 2009-298767 Summary of the invention

[0005] One object of an embodiment of the present invention is to provide a novel organic compound. Another object of an embodiment of the present invention is to provide a novel charge carrier transport material. Another object of an embodiment of the present invention is to provide a novel perforated transport material. A further object of an embodiment of the present invention is to provide a highly heat-resistant charge carrier transport material or perforated transport material.

[0006] Another object of an embodiment of the present invention is to provide an organic semiconductor device with a small change in operating voltage over its operating time. Another object of an embodiment of the present invention is to provide an organic semiconductor device with a long operating time. Another object of an embodiment of the present invention is to provide an organic semiconductor device, a light-emitting device, an electronic device, a display device, and an electronic device, each of which has low power consumption.

[0007] It should be noted that the description of these problems does not preclude the existence of further problems. An embodiment of the present invention need not necessarily fulfill all of these problems. Further problems will become apparent from the explanation of the description, the drawings, the claims, and the like, and can be derived from them.

[0008] One embodiment of the present invention is an organic compound represented by the general formula (G1).

[0009] In the general formula (G1) α represents 1 represents a substituted or unsubstituted phenylene group; n is 1 or 2; α 2 represents a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group; m is 0, 1, or 2; R 1 to R 7Each independently represents hydrogen (including deuterium), a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, or a substituted or unsubstituted phenyl group; Ar 2 represents a group defined by the general formula (Ar 2 -a) or the general formula (Ar 2 -b) is represented; one of R 8 to R 17 represents a bond; other R 8 to R 17 as the bond as well as R 18 to R 28 and R 31 to R 34Each independently represents hydrogen (including deuterium), a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a silyl group with 3 to 18 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms; and X represents oxygen or sulfur. If n is 2, a variety of α can be 1 They can be the same or different from each other. If m is 2, a variety of α can be used. 2 be the same or different from each other.

[0010] Another embodiment of the present invention is an organic compound represented by the general formula (G2).

[0011] In the general formula (G2) α represents 2 a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group; m is 0, 1 or 2; R 1 to R 7 and R 35 to R 38 Each independently represents hydrogen (including deuterium), a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms; Ar 2 represents a group defined by the general formula (Ar 2 -a) or the general formula (Ar 2 -b) is represented; one of R 8 to R 17 represents a bond; other R 8 to R 17as the bond as well as R 18 to R 28 and R 31 to R 34 Each independently represents hydrogen (including deuterium), a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a silyl group with 3 to 18 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms; and X represents oxygen or sulfur. If m is 2, a variety of α can be 2 be the same or different from each other.

[0012] Another embodiment of the present invention is the organic compound represented by the general formula (G2), where m is 0.

[0013] Another embodiment of the present invention is an organic compound represented by the general formula (G4).

[0014] In the general formula (G4) R 1 to R 7 and R 35 to R 38 each independently represents hydrogen (including deuterium), a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms; other R 9 to R 17 as the bond as well as R 18 to R 28 and R 31 to R 34Each independently represents hydrogen (including deuterium), a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a silyl group with 3 to 18 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms; and X represents oxygen or sulfur.

[0015] Another embodiment of the present invention is an organic compound represented by the general formula (G5).

[0016] In the general formula (G5) R 1 to R 7 and R35 to R 38 each independently represents hydrogen (including deuterium), a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms; other R 9 to R 17 as the bond as well as R 18 to R 28 and R 31 to R 34Each independently represents hydrogen (including deuterium), a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a silyl group with 3 to 18 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms; and X represents oxygen or sulfur.

[0017] Another embodiment of the present invention is an organic compound represented by the general formula (G7).

[0018] In the general formula (G7) α represents 2a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group; m is 0, 1 or 2; R 1 to R 7 and R 35 to R 38 Each independently represents hydrogen (including deuterium), a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms; Ar 2 represents a group defined by the general formula (Ar 2 -b) is represented; one of R 8 to R 17 represents a bond; other R 8 to R 17 as the bond as well as R 18 to R 34Each independently represents hydrogen (including deuterium), a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a silyl group with 3 to 18 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms; and X represents oxygen or sulfur. If m is 2, a variety of α can be 2 be the same or different from each other.

[0019] Another embodiment of the present invention is the organic compound represented by the general formula (G7), where m is 0.

[0020] Another embodiment of the present invention is an organic compound represented by the structural formula (100) or the structural formula (101).

[0021] Another embodiment of the present invention is an organic semiconductor device comprising the organic compound with any of the aforementioned structures.

[0022] Another embodiment of the present invention is a light-emitting device comprising the organic compound with any of the aforementioned structures.

[0023] Another embodiment of the present invention is a light-emitting device comprising a first electrode, a second electrode, a light-emitting layer and a first layer wherein the light-emitting layer is positioned between the first electrode and the second electrode, the first layer is positioned between the first electrode and the light-emitting layer and the first layer contains an organic compound represented by the general formula (G8).

[0024] In the general formula (G8) α 1 and α 2 each independently represents a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group; n is 1 or 2; m is 0, 1 or 2; R 1 to R 7Each independently represents hydrogen (including deuterium), a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, or a substituted or unsubstituted phenyl group; Ar 2 represents a substituted or unsubstituted benzo[b]naphtho[2,1-d]furanyl group, a substituted or unsubstituted benzo[b]naphtho[2,3-d]furanyl group, a substituted or unsubstituted benzo[b]naphtho[2,1-d]thiophenyl group, or a substituted or unsubstituted benzo[b]naphtho[2,3-d]thiophenyl group; and Ar 3 represents a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted spirobifluorenyl group. If n is 2, a variety of α can be used. 1 They can be the same or different from each other. If m is 2, a variety of α can be used.2 be the same or different from each other.

[0025] Another embodiment of the present invention is a light-emitting device comprising a first electrode, a second electrode, a light-emitting layer and a first layer wherein the light-emitting layer is positioned between the first electrode and the second electrode, the first layer is positioned between the first electrode and the light-emitting layer and the first layer contains an organic compound represented by the general formula (G9).

[0026] In the general formula (G9) α 1 and α 2 each independently represents a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group; n is 1 or 2; m is 0, 1 or 2; R 1 to R 7Each independently represents hydrogen (including deuterium), a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, or a substituted or unsubstituted phenyl group; Ar 2 represents a group defined by the general formula (Ar 2 -a) or the general formula (Ar 2 -b) is represented; one of R 8 to R 17 represents a bond; other R 8 to R 17 as the bond as well as R 18 to R 28 and R 31 to R 34Each independently represents hydrogen (including deuterium), a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a silyl group with 3 to 18 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms; if R 29 and R 30 Each representing a bond, are R 29 and R 30 bound together to form a ring; if neither R 29 still R 30 representing a bond, R 29 and R 30Each independently represents hydrogen (including deuterium), a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a silyl group with 3 to 18 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms; and X represents oxygen or sulfur. If n is 2, a variety of α can be 1 They can be the same or different from each other. If m is 2, a variety of α can be used. 2 be the same or different from each other.

[0027] In the case of the light-emitting layer with any of the above structures, the first layer is preferably in contact with the light-emitting layer.

[0028] In the case of the light-emitting layer with any of the above structures, it is preferred that the first layer is in contact with the light-emitting layer, that the light-emitting layer contains a first host material, a second host material and a light-emitting substance, that the first host material and the second host material in combination form an exciplex, and that the difference between the peak wavelength of the emission spectrum of the exciplex and the peak wavelength of the emission spectrum of the light-emitting substance is less than or equal to 30 nm.

[0029] In the case of the light-emitting layer with any of the above structures, it is preferred that the first layer is in contact with the light-emitting layer and that the light-emitting layer contains a host material and a fluorescent substance.

[0030] According to one embodiment of the present invention, a novel organic compound can be provided. According to one embodiment of the present invention, a novel load carrier transport material can be provided. According to one embodiment of the present invention, a novel perforated transport material can be provided. According to one embodiment of the present invention, a highly heat-resistant load carrier transport material or perforated transport material can be provided.

[0031] According to a further embodiment of the present invention, an organic semiconductor device can be provided with a small change in operating voltage over the operating time. According to a further embodiment of the present invention, an organic semiconductor device with a long operating time can be provided. According to a further embodiment of the present invention, an organic semiconductor device, a light-emitting device, an electronic device, a display device, and an electronic device can each be provided, all of which have low power consumption.

[0032] It should be noted that the description of these effects does not preclude the existence of further effects. An embodiment of the present invention need not necessarily exhibit all of these effects. Further effects can be derived from the explanation of the description, the drawings, and the claims. Brief description of the drawings Fig. 1A to Fig. 1C each represent a structure of an organic semiconductor device of one embodiment. Fig. 2A and Fig. 2B each represent a structure of a device of an embodiment. Fig. 3A to Fig. 3F each represent a structure of a light-emitting device of an embodiment. Fig. 4A and Fig. Figure 4B shows a top view or a cross-sectional view of a display device. Fig. 5A and Fig. 5B are perspective views that represent a structural example of a display module. Fig. 6A and Fig. Figure 6B shows cross-sectional views that illustrate a structural example of a display device. Fig. Figure 7 is a perspective view that shows a structural example of a display device. Fig. Figure 8A is a cross-sectional view showing a structural example of a display device. Fig. 8B and Fig. 8C are cross-sectional views that represent a structural example of a transistor. Fig. Figure 9 is a cross-sectional view that shows a structural example of a display device. Fig. 10A to Fig. Figures 10C are a cross-sectional view and top views that represent a structural example of a display device. Fig. 11A to Fig. 11D are cross-sectional views that represent structural examples of a display device. Fig. 12A to Fig. Figures 12C are a cross-sectional view and top views that represent a structural example of a display device. Fig. 13A to Fig. 13D shows examples of electronic devices. Fig. 14A to Fig. 14F provide examples of electronic devices. Fig. 15A to Fig. 15G provide examples of electronic devices. Fig. Figure 16 represents a structure of a light-emitting device of an example. Fig. 17 shows a 1 H-NMR spectrum of SFNBaBnf(10). Fig. Figure 18 shows an absorption spectrum and an emission spectrum of a toluene solution of SFNBaBnf(10). Fig. Figure 19 shows an absorption spectrum and an emission spectrum of a thin film of SFNBaBnf(10). Fig. 20A and Fig. 20B show a phosphorescence spectrum of SFNBaBnf(10). Fig. 21 shows a 1 H-NMR spectrum of SFNBBnf(II)(4). Fig. Figure 22 shows an absorption spectrum and an emission spectrum of a toluene solution of SFNBBnf(II)(4). Fig. Figure 23 shows an absorption spectrum and an emission spectrum of a thin film of SFNBBnf(II)(4). Fig. 24A and Fig. 24B show a phosphorescence spectrum of SFNBBnf(II)(4). Fig. Figure 25 shows emission spectra of a film of 8mpTP-4mDBtPBfpm, a film of βNCCP and a mixed film of 8mpTP-4mDBtPBfpm and βNCCP. Fig. Figure 26 shows an absorption spectrum and an emission spectrum of Ir(5mppy-d3)2(mbfpypy-d3). Fig. Figure 27 shows luminance-current density properties of a light-emitting device 1, a light-emitting device 2, a light-emitting comparison device 3 and a light-emitting comparison device 4. Fig. Figure 28 shows luminance-voltage properties of the light-emitting devices 1 and 2 and the light-emitting comparison devices 3 and 4. Fig. Figure 29 shows the power efficiency-luminance characteristics of the light-emitting devices 1 and 2 and the light-emitting comparison devices 3 and 4. Fig. Figure 30 shows current density-voltage characteristics of the light-emitting devices 1 and 2 and the light-emitting comparison devices 3 and 4. Fig. Figure 31 shows external quantum efficiency luminance properties of the light-emitting devices 1 and 2 and the light-emitting comparison devices 3 and 4. Fig. Figure 32 shows electroluminescence spectra of the light-emitting devices 1 and 2 and the light-emitting comparison devices 3 and 4. Fig. Figure 33 shows luminance-current density properties of a light-emitting device 5, a light-emitting device 6, a light-emitting comparison device 7 and a light-emitting comparison device 8. Fig. Figure 34 shows luminance-voltage properties of the light-emitting devices 5 and 6 and the light-emitting comparison devices 7 and 8. Fig. Figure 35 shows the power efficiency-luminance characteristics of the light-emitting devices 5 and 6 and the light-emitting comparison devices 7 and 8. Fig. Figure 36 shows current density-voltage properties of the light-emitting devices 5 and 6 and the light-emitting comparison devices 7 and 8. Fig. Figure 37 shows external quantum efficiency luminance properties of the light-emitting devices 5 and 6 and the light-emitting comparison devices 7 and 8. Fig. Figure 38 shows electroluminescence spectra of the light-emitting devices 5 and 6 and the light-emitting comparison devices 7 and 8. Fig. Figure 39 shows the time dependence of the normalized luminance of the light-emitting devices 1 and 2 and the light-emitting comparison devices 3 and 4. Fig. Figure 40 shows the time dependence of the normalized luminance of the light-emitting devices 5 and 6 and the light-emitting comparison devices 7 and 8. Fig. Figure 41 shows luminance-current density properties of a light-emitting device 9, a light-emitting device 10, a light-emitting comparison device 11 and a light-emitting comparison device 12. Fig. Figure 42 shows luminance-voltage properties of the light-emitting devices 9 and 10 and the light-emitting comparison devices 11 and 12. Fig. Figure 43 shows the power efficiency-luminance characteristics of the light-emitting devices 9 and 10 and the light-emitting comparison devices 11 and 12. Fig. Figure 44 shows current density-voltage characteristics of the light-emitting devices 9 and 10 and the light-emitting comparison devices 11 and 12. Fig. Figure 45 shows external quantum efficiency luminance properties of the light-emitting devices 9 and 10 and the light-emitting comparison devices 11 and 12. Fig. Figure 46 shows electroluminescence spectra of the light-emitting devices 9 and 10 and the light-emitting comparison devices 11 and 12. Fig. Figure 47 shows the time dependence of the normalized luminance of the light-emitting devices 9 and 10 and the light-emitting comparison devices 11 and 12. Fig. 48 shows a 1 H NMR spectrum of FLP(2)NBBnf(II)(4). Fig. Figure 49 shows an absorption spectrum and an emission spectrum of a toluene solution of FLP(2)NBBnf(II)(4). Fig. Figure 50 shows an absorption spectrum and an emission spectrum of a thin film of FLP(2)NBBnf(II)(4). Fig. 51A and Fig. 51B show a phosphorescence spectrum of FLP(2)NBBnf(II)(4). Fig. Figure 52 shows luminance-current density properties of a light-emitting device 13 and a light-emitting comparison device 14. Fig. Figure 53 shows luminance-voltage properties of the light-emitting device 13 and the light-emitting comparison device 14. Fig. Figure 54 shows power efficiency-luminance characteristics of the light-emitting device 13 and the light-emitting comparison device 14. Fig. Figure 55 shows current density-voltage characteristics of the light-emitting device 13 and the light-emitting comparison device 14. Fig. Figure 56 shows external quantum efficiency luminance properties of the light-emitting device 13 and the light-emitting comparison device 14. Fig. Figure 57 shows electroluminescence spectra of the light-emitting device 13 and the light-emitting comparison device 14. Fig. Figure 58 shows the time dependence of the normalized luminance of the light-emitting device 13. Detailed description of the invention

[0033] Embodiments of the present invention are described in detail below with reference to the drawings. It should be noted that the present invention is not limited to the following description and that the modes and details of the present invention can be modified in various ways without departing from the concept and scope of the present invention. Therefore, the present invention should not be considered as limited to the description of the following embodiments.

[0034] It should be noted that the position, size, area, or the like of each component shown in drawings and the like is, in some cases, not shown precisely for ease of understanding. Therefore, the disclosed invention is not necessarily limited to the position, size, area, or the like disclosed in the drawings and the like.

[0035] The ordinal numbers, such as "first" and "second," are used in this description and the like for the sake of simplicity, and in some cases they do not indicate the sequence of steps or the order of layer arrangement. Therefore, for example, an appropriate description may be given even if "first" is replaced by "second" or "third." Furthermore, the ordinal numbers in this description and the like are not necessarily the same as those used to specify an embodiment of the present invention.

[0036] When explaining the structures of the present invention in this description and the like with reference to the drawings, in some cases the same components in different drawings are provided with the same reference numerals.

[0037] In this description and similar texts, the terms "film" and "layer" may be used interchangeably. For example, the term "conducting layer" may, in some cases, be replaced by the term "conducting film." Similarly, the term "insulating film" may, in some cases, be replaced by the term "insulating layer." (Version 1)

[0038] In this embodiment, an organic compound of an embodiment of the present invention and an organic semiconductor device of an embodiment of the present invention are described.

[0039] The organic compound of an embodiment of the present invention is a triarylamine having a structure in which a first aryl group, a second aryl group, and a third aryl group are bonded to a nitrogen atom. Triarylamines exhibit a high lowest unoccupied molecular orbital (LUMO) level and a large gap between the highest occupied molecular orbital (HOMO) and the LUMO, resulting in excellent hole transport properties and enabling their use in various organic semiconductor devices.

[0040] In the organic compound of one embodiment of the present invention, the first aryl group comprises a naphthyl group bonded to the nitrogen atom via a phenylene group or a biphenyldiyl group. It should be noted that the naphthyl group and the phenylene group or the biphenyldiyl group may each contain a substituent. A naphthalene ring has a stable structure in which two benzene rings are fused. Since a structure in which a naphthyl group is bonded to a phenylene group or a biphenyldiyl group has a π-electron-conjugated system extending over the naphthyl group and the phenylene group or biphenyldiyl group, the organic compound comprising the first aryl group with such a structure can exhibit high hole transport properties. The organic compound comprising the first aryl group with such a structure can also exhibit high stability.Furthermore, when the first aryl contains such a structural group, the glass transition temperature of the organic compound is increased, leading to improved heat resistance. This makes the organic compound of an embodiment of the present invention highly resistant to high-temperature treatment after film formation. For example, even if the organic compound of an embodiment of the present invention is formed into a film by evaporation and a material requiring evaporation at a very high temperature is deposited over this film, the quality of the film does not change significantly. Moreover, the organic compound of an embodiment of the present invention can be formed into a film of high purity and high quality, since decomposition or deterioration of the organic compound due to heat is unlikely to occur.Consequently, a film with stable quality can be formed. Using such an organic compound, an organic semiconductor device with high reliability and high quality can be manufactured.

[0041] The second aryl group comprises a benzo[b]naphtho[2,1-d]furanyl group, a benzo[b]naphtho[2,3-d]furanyl group, a benzo[b]naphtho[2,1-d]thiophenyl group, or a benzo[b]naphtho[2,3-d]thiophenyl group, which is bonded directly or via an arylene group to the nitrogen. It should be noted that these groups and the arylene group may each contain a substituent. A benzo[b]naphtho[2,1-d]furan ring, a benzo[b]naphtho[2,3-d]furan ring, a benzo[b]naphtho[2,1-d]thiophene ring, and a benzo[b]naphtho[2,3-d]thiophene ring each comprise a fused naphthalene ring. This causes the π-electron-conjugated system to extend, allowing them to easily accept electrons. Therefore, thanks to the second aryl group encompassing any one of these rings present in the organic compound, there is a tendency for the LUMO of the organic compound to spread across the ring.Consequently, the LUMO is less likely to distribute itself over the other aryl groups (first and third aryl groups) in the organic compound of an embodiment of the present invention. This makes the molecule of the organic compound as a whole more resistant to reduction. Therefore, by using the organic compound of an embodiment of the present invention, a significant change in the operating voltage of an organic semiconductor device over its operating time can be prevented. The organic semiconductor device can also exhibit an extended operating life.

[0042] In this description and the like, a benzo[b]-naphtho[2,1-d]furanyl group denotes a monovalent group obtained by eliminating a hydrogen from a benzo[b]naphtho[2,1-d]furan ring, a benzo[b]naphtho[2,3-d]furanyl group denotes a monovalent group obtained by eliminating a hydrogen from a benzo[b]naphtho[2,3-d]furan ring, a benzo[b]naphtho[2,1-d]thiophenyl group denotes a monovalent group obtained by eliminating a hydrogen from a benzo[b]naphtho[2,1-d]thiophene ring, and a benzo[b]naphtho[2,3-d]thiophenyl group denotes a monovalent group obtained by eliminating a hydrogen from a benzo[b]naphtho[2,3-d]thiophene ring.

[0043] The third aryl group comprises a spirobifluorenyl group or a diphenylfluorenyl group directly bonded to the nitrogen atom. It should be noted that the spirobifluorenyl group or the diphenylfluorenyl group can each have one substituent. Since spirobifluorenyl and diphenylfluorenyl groups are bulky, their introduction can reduce intermolecular stacking or similar effects. In particular, their introduction into an organic compound containing many aromatic rings can lower the sublimation temperature of the compound, thus preventing thermal decomposition during sublimation.

[0044] Next, the organic compound of an embodiment of the present invention will be described using general formulas.

[0045] One embodiment of the present invention is an organic compound represented by the general formula (G1).

[0046] In the general formula (G1) α represents 1 represents a substituted or unsubstituted phenylene group; n is 1 or 2; α 2 represents a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group; m is 0, 1, or 2; R 1 to R 7 Each independently represents hydrogen (including deuterium), a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, or a substituted or unsubstituted phenyl group; Ar 2 represents a group defined by the general formula (Ar 2 -a) or the general formula (Ar 2 -b) is represented; one of R8 to R 17 represents a bond; other R 8 to R 17 as the bond as well as R 18 to R 28 and R 31 to R 34 Each independently represents hydrogen (including deuterium), a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a silyl group with 3 to 18 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms; and X represents oxygen or sulfur. If n is 2, a variety of α can be 1They can be the same or different from each other. If m is 2, a variety of α can be used. 2 be the same or different from each other.

[0047] As described above, the organic compound represented by the general formula (G1) exhibits high stability and high heat resistance due to the inclusion of the naphthyl group, which is bonded to the nitrogen via the phenylene or biphenyldiyl group. Consequently, a highly reliable and high-quality organic semiconductor device can be fabricated using such an organic compound.

[0048] As described above, since the organic compound represented by the general formula (G1) comprises a benzo[b]naphtho[2,1-d]furanyl group, a benzo[b]naphtho[2,3-d]furanyl group, a benzo[b]naphtho[2,1-d]thiophenyl group, or a benzo[b]naphtho[2,3-d]thiophenyl group bonded directly or via an arylene group to the nitrogen, the use of this organic compound can prevent a significant change in the operating voltage of an organic semiconductor device over its operating time. The organic semiconductor device may also exhibit an extended operating time.

[0049] Since the organic compound represented by the general formula (G1) includes a spirobifluorene ring, the organic compound has a low sublimation temperature and is less likely to be thermally decomposed during sublimation.

[0050] Another embodiment of the present invention is an organic compound represented by the general formula (G2).

[0051] In the general formula (G2) α represents 2 a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group; m is 0, 1 or 2; R 1 to R 7 and R 35 to R 38 Each independently represents hydrogen (including deuterium), a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms; Ar 2 represents a group defined by the general formula (Ar 2 -a) or the general formula (Ar 2 -b) is represented; one of R 8 to R 17 represents a bond; other R 8 to R 17as the bond as well as R 18 to R 28 and R 31 to R 34 Each independently represents hydrogen (including deuterium), a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a silyl group with 3 to 18 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms; and X represents oxygen or sulfur. If m is 2, a variety of α can be 2 be the same or different from each other.

[0052] General formula (G2) differs from general formula (G1) in that n in general formula (G1) is limited to 1. When n is limited to 1, the molecular weight is lower than when n is 2, preventing an excessive increase in the sublimation temperature of the organic compound. This contributes to improvements in the quality and purity of the film formed by evaporation of the organic compound, leading to greater reliability of the device. Furthermore, when n is limited to 1, the solubility in a solvent is less likely to decrease than when n is 2. This simplifies purification by a general solution process, reduces the strain on the purification process, and makes it easier to achieve high purity of the organic compound, which is preferable.It is preferred that m in the general formula (G2) is 0, as this leads to an increase in these effects.

[0053] Another embodiment of the present invention is an organic compound represented by the general formula (G3).

[0054] In the general formula (G3) R 1 to R 7 and R 35 to R 38 each independently represents hydrogen (including deuterium), a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms; Ar 2 represents a group defined by the general formula (Ar 2 -a) or the general formula (Ar 2 -b) is represented; one of R 8 to R 17 represents a bond; other R 8 to R 17 as the bond as well as R 18 to R 28and R 31 to R 34 Each independently represents hydrogen (including deuterium), a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a silyl group with 3 to 18 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms; and X represents oxygen or sulfur. If n is 2, a variety of α can be 1 They can be the same or different from each other. If m is 2, a variety of α can be used. 2 be the same or different from each other.

[0055] General formula (G3) differs from general formula (G2) in that the phenylene group, the naphthyl group, and m in general formula (G2) are restricted to a p-phenylene group, a 1-naphthyl group, and 0, respectively. When the phenylene group is a p-phenylene group, the π-electron-conjugated system formed by the phenylene and naphthyl groups extends more readily than when the phenylene group is an o-phenylene or an m-phenylene group. This increases the stability of the organic compound. Furthermore, if the phenylene group is a p-phenylene group, the distortion of the molecular structure can be small and the glass transition temperature can be higher than in the case where the phenylene group is an o-phenylene group or an m-phenylene group, which is preferable.If the naphthyl group is a 1-naphthyl group, the hole transport properties, reliability, and heat resistance of the organic compound can be improved more significantly than in the case where the naphthyl group is a 2-naphthyl group. Furthermore, if m is 0, an excessive increase in the sublimation temperature of the organic compound can be prevented, and the reliability of the organic compound can be improved. In this case, the solubility is less likely to decrease, which reduces the strain on the purification process and makes it easier to achieve high purity of the organic compound, which is preferable.

[0056] Another embodiment of the present invention is the organic compound represented by the general formula (G4).

[0057] In the general formula (G4) R 1 to R 7 and R35 to R 38 each independently represents hydrogen (including deuterium), a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms; other R 9 to R 17 as the bond as well as R 18 to R 28 and R 31 to R 34Each independently represents hydrogen (including deuterium), a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a silyl group with 3 to 18 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms; and X represents oxygen or sulfur.

[0058] The general formula (G4) differs from the general formula (G3) in that Ar 2 in the general formula (G3) is restricted to the group defined by the general formula (Ar 2 -a) is represented. If Ar2 the group is defined by the general formula (Ar 2 -a) is shown, the lowest triplet excitation level (T1 level) is higher than that in the case where Ar 2 the group is defined by the general formula (Ar 2 -b) is shown. By using this compound for a layer in contact with a light-emitting layer of a light-emitting device, exciton diffusion from the light-emitting layer into an adjacent layer or the like can be prevented, thus increasing the emission efficiency of the light-emitting device.

[0059] Another embodiment of the present invention is an organic compound represented by the general formula (G5).

[0060] In the general formula (G5) R 1 to R 7 and R 35 to R 38each independently represents hydrogen (including deuterium), a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms; other R 9 to R 17 as the bond as well as R 18 to R 28 and R 31 to R 34Each independently represents hydrogen (including deuterium), a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a silyl group with 3 to 18 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms; and X represents oxygen or sulfur.

[0061] The general formula (G5) differs from the general formula (G3) in that Ar 2 in the general formula (G3) is restricted to the group defined by the general formula (Ar 2 -b) is represented. If Ar2 the group is defined by the general formula (Ar 2 -b) As shown, the organic compound can exhibit higher reliability and higher hole transport properties. Furthermore, the HOMO level of the organic compound is higher than that in the case where Ar 2 the group is defined by the general formula (Ar 2 -a) is represented. The organic compound is also very resistant to repeated oxidation and repeated reduction, which is preferable.

[0062] If Ar 2 is restricted to the group defined by the general formula (Ar 2 -b) is shown, it is also preferable that the third aryl group in the organic compound of an embodiment of the present invention comprises a diphenylfluorenyl group. This is because the organic compound in which Ar 2 the group is defined by the general formula (Ar 2-b) can be very reliable even if the third aryl group does not comprise a spirobifluorenyl group, but a diphenylfluorenyl group.

[0063] Another embodiment of the present invention is an organic compound represented by the general formula (G6).

[0064] In the general formula (G7) 1 represents a substituted or unsubstituted phenylene group; n is 1 or 2; α 2 represents a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group; m is 0, 1, or 2; R 1 to R 7 and R 35 to R 38Each independently represents hydrogen (including deuterium), a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms; Ar 2 represents a group defined by the general formula (Ar 2 -b) is represented; one of R 8 to R 17 represents a bond; other R 8 to R 17 as the bond as well as R 18 to R 34Each independently represents hydrogen (including deuterium), a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a silyl group with 3 to 18 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms; and X represents oxygen or sulfur. If n is 2, a variety of α can be 1 They can be the same or different from each other. If m is 2, a variety of α can be used. 2 be the same or different from each other.

[0065] The general formula (G6) differs from the general formula (G2) in that Ar 2 in the general formula (G2) is restricted to the group defined by the general formula (Ar 2 -b) is represented, and the third aryl group comprises a diphenylfluorenyl group. As described above, the organic compound in which Ar 2 is restricted to the group defined by the general formula (Ar 2 -b) is represented, can be very reliable even if the third aryl group does not comprise a spirobifluorenyl group, but a diphenylfluorenyl group.

[0066] Another embodiment of the present invention is an organic compound represented by the general formula (G7).

[0067] In the general formula (G7) α represents 2a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group; m is 0, 1 or 2; R 1 to R 7 and R 35 to R 38 Each independently represents hydrogen (including deuterium), a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms; Ar 2 represents a group defined by the general formula (Ar 2 -b) is represented; one of R 8 to R 17 represents a bond; other R 8 to R 17 as the bond as well as R 18 to R 34Each independently represents hydrogen (including deuterium), a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a silyl group with 3 to 18 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms; and X represents oxygen or sulfur. If m is 2, a variety of α can be 2 be the same or different from each other.

[0068] General formula (G7) differs from general formula (G6) in that n in general formula (G6) is limited to 1. Limiting n to 1 prevents an excessive increase in the sublimation temperature of the organic compound and improves the reliability of a film formed by evaporation of the organic compound. Furthermore, since the solubility is less likely to decrease, a high purity of the organic compound can be easily achieved in the purification process, which is preferable. It is preferable for m to be 0 in general formula (G7) because this enhances these effects.

[0069] If X is oxygen in any of the above general formulas, the refractive index of the organic compound can be lower than that in the case where X is sulfur. The organic compound with a lower refractive index improves light extraction efficiency when used, for example, in a light-emitting device, which is preferable. It is preferred that X be oxygen because this generally simplifies the synthesis of the organic compound and facilitates its industrial use.

[0070] In contrast, if X is sulfur in any of the above general formulas, the heat resistance (e.g., decomposition temperature, melting point, or sublimation point) of the organic compound can be higher than that in the case where X is oxygen. The organic compound with higher heat resistance is preferably used, for example, in a light-emitting device, in which case an organic semiconductor device can be provided that can operate stably in a high-temperature environment.

[0071] Next, specific examples of substituents that can be used for the organic compounds represented by the general formulas above are described. It should be noted that the groups that can be used in the general formulas above are not limited to the specific examples that follow. Furthermore, in the specific examples described below, some or all of the hydrogen atoms can be deuterium. < <halogen>>

[0072] Specific examples of halogens include fluorine, chlorine, bromine, and iodine. Fluorine, in particular, is preferred because it is chemically stable. <<Geradkettige oder verzweigtkettige Alkyl-Gruppe mit 1 bis 6 Kohlenstoffatomen> >

[0073] A straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms refers to a monovalent group obtained by eliminating a hydrogen (H) atom from a straight-chain or branched-chain alkane with 1 to 6 carbon atoms. Specific examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a neopentyl group, a hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, a neo-hexyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 2-ethylbutyl group, a 1,2-dimethylbutyl group, a 2,3-dimethylbutyl group, and the like. <<Alkenyl-Gruppe mit 2 bis 6 Kohlenstoffatomen> >

[0074] An alkenyl group with 2 to 6 carbon atoms is a monovalent group obtained by removing one hydrogen atom from an alkene with 2 to 6 carbon atoms. Specific examples of an alkenyl group with 2 to 6 carbon atoms include a vinyl group, an aryl group, and a 2,2-dimethylvinyl group. <<Alkinyl-Gruppe mit 2 bis 6 Kohlenstoffatomen> >

[0075] An alkynyl group with 2 to 6 carbon atoms is a monovalent group obtained by removing one hydrogen atom from an alkyne containing 2 to 6 carbon atoms. Specific examples of an alkynyl group with 2 to 6 carbon atoms include an ethynyl group and a prop-2-yn-1-yl group (also called a propargyl group). <<Alkoxy-Gruppe mit 1 bis 6 Kohlenstoffatomen> >

[0076] An alkoxy group with 1 to 6 carbon atoms has a structure in which a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms is bonded to oxygen (O). Specific examples of an alkoxy group with 1 to 6 carbon atoms include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, an isobutoxy group, a tert-butoxy group, an n-pentyloxy group, an isopentyloxy group, a sec-pentyloxy group, a tert-pentyloxy group, a neo-pentyloxy group, an n-hexyloxy group, an isohexyloxy group, a sec-hexyloxy group, a tert-hexyloxy group, a neo-hexyloxy group, a cyclohexyloxy group, and the like. <<Silyl-Gruppe mit 3 bis 18 Kohlenstoffatomen> >

[0077] A silyl group with 3 to 18 carbon atoms has a structure in which three alkyl groups with a total of 3 to 18 carbon atoms or three aryl groups with a total of 3 to 18 carbon atoms are bonded to silicon (Si). Specific examples of a silyl group with 3 to 18 carbon atoms include a trimethylsilyl group, a triethylsilyl group, a tert-butyldimethylsilyl group, a triphenylsilyl group, and the like. <<Cycloalkyl-Gruppe mit 3 bis 10 Kohlenstoffatomen> >

[0078] A cycloalkyl group with 3 to 10 carbon atoms is a monovalent group obtained by removing one hydrogen atom from a monocyclic or polycyclic cycloalkane with 3 to 10 carbon atoms. Specific examples of a cycloalkyl group with 3 to 10 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cycloononyl group, a cyclodecyl group, a norbornyl group, a bicyclo[2,2,2]octyl group, a decahydronaphthyl group, an adamantyl group, and the like.In the case where the cycloalkyl group with 3 to 10 carbon atoms includes a substituent, specific examples of the substituent include a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a trialkylsilyl group with 3 to 10 carbon atoms, a phenyl group, and the like. <<Aryl-Gruppe mit 6 bis 30 Kohlenstoffatomen> >

[0079] An aryl group with 6 to 30 carbon atoms is a monovalent group obtained by removing one hydrogen atom from one of carbon atoms forming a ring of a monocyclic or polycyclic aromatic compound with 6 to 30 carbon atoms. Specific examples of an aryl group with 6 to 30 carbon atoms include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a mesityl group, a biphenyl-2-yl group (o-biphenyl group), a biphenyl-3-yl group (m-biphenyl group), a biphenyl-4-yl group (p-biphenyl group), a 1-naphthyl group, a 2-naphthyl group, a phenylnaphthyl group, a naphthylphenyl group, a terphenyl group, a fluorenyl group, a 9,9-dimethylfluorenyl group, a quaterphenyl group, a spirobifluorenyl group, a phenanthryl group, an anthryl group, a binaphthylphenyl group, a fluoranthenyl group, and the like.In the case where the aryl group with 6 to 30 carbon atoms includes a substituent, specific examples of the substituent include a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a trialkylsilyl group with 3 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, a phenyl group, and the like. <<Heteroaryl-Gruppe mit 2 bis 30 Kohlenstoffatomen> >

[0080] A heteroaryl group with 2 to 30 carbon atoms is a monovalent group obtained by removing a hydrogen atom from one of the carbon atoms forming a ring of a monocyclic or polycyclic heterocyclic aromatic compound with 2 to 30 carbon atoms.Specific examples of a heteroaryl group with 2 to 30 carbon atoms include a carbazolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, a benzocarbazolyl group, a naphthobenzothiophenyl group, a naphthobenzofuranyl group, a dibenzocarbazolyl group, a dinaphthothiophenyl group, a dinaphthofuranyl group, a triazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazolyl group, a pyridinyl group, a benzofuropyrimidinyl group, a benzothiopyrimidinyl group, a benzofuropyrazinyl group, a benzothiopyrazinyl group, a benzofuropyridinyl group, a benzothiopyridinyl group, a bicarbazolyl group, and the like.In the case where the heteroaryl group with 2 to 30 carbon atoms includes a substituent, specific examples of the substituent include a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a trialkylsilyl group with 3 to 10 carbon atoms, a cycloalkyl group with 3 to 10 carbon atoms, a phenyl group, and the like.

[0081] The above substituents are specific examples of the substituent that can be used for the organic compounds represented by the general formulas.

[0082] Specific examples of the organic compounds of embodiments of the present invention, represented by the general formulas above, include organic compounds represented by the structural formulas (100) to (237) below. It should be noted that the organic compound of an embodiment of the present invention is not limited to the organic compounds represented by the following structural formulas.

[0083] Next, methods for synthesizing the organic compounds represented by the general formulas (G1) and (G7) are described as an example of a method for synthesizing the organic compound of an embodiment of the present invention. < <Syntheseverfahren der organischen Verbindung, die durch die allgemeine Formel (G1) dargestellt wird> >

[0084] The organic compound represented by the general formula (G1) can be synthesized according to the synthesis scheme (S-1) and the synthesis scheme (S-9).

[0085] First, the synthesis scheme (S-1) is described. In particular, an amine compound with a naphthalene framework (compound 1) and a spirobifluorene compound (compound 2) are coupled to obtain a spirobifluorenamine compound with a naphthalene framework (compound 3). The synthesis scheme (S-1) is shown below.

[0086] Next, the synthesis scheme (S-2) is described. In particular, the spirobifluorenamine compound with a naphthalene scaffold (compound 3) and a compound with a benzonaphthofuran scaffold or a benzonaphthothiophene scaffold (compound 4) are coupled to obtain the organic compound represented by the general formula (G1). The synthesis scheme (S-2) is shown below.

[0087] The spirobifluorenamine compound with a naphthalene framework (compound 3) in synthesis schemes (S-1) and (S-2) can also be synthesized according to synthesis scheme (S-3). Specifically, a halogenated aryl compound with a naphthalene framework (compound 5) and a spirobifluorenamine compound (compound 6) are coupled to obtain the spirobifluorenamine compound with a naphthalene framework (compound 3). Synthesis scheme (S-3) is shown below.

[0088] Next, the synthesis scheme (S-4) is described. In particular, the spirobifluorenamine compound (compound 6) and the compound with a benzonaphthofuran or benzonaphthothiophene scaffold (compound 4) are coupled to obtain a spirobifluorenamine compound with a benzonaphthofuran or benzonaphthothiophene scaffold (compound 7). The synthesis scheme (S-4) is shown below.

[0089] Next, the synthesis scheme (S-5) is described. In particular, the halogenated aryl compound with a naphthalene framework (compound 5) and a spirobifluorenamine compound with a benzonaphthofuran framework or a benzonaphthothiophene framework (compound 7) are coupled to obtain the organic compound represented by the general formula (G1). The synthesis scheme (S-5) is shown below.

[0090] The spirobifluorenamine compound with a benzonaphthofuran or benzonaphthothiophene scaffold (compound 7) in synthesis schemes (S-4) and (S-5) can also be synthesized according to synthesis scheme (S-6). Specifically, the spirobifluorene compound (compound 2) and an amine compound with a benzonaphthofuran or benzonaphthothiophene scaffold (compound 8) are coupled to obtain the spirobifluorenamine compound with a benzonaphthofuran or benzonaphthothiophene scaffold (compound 7). Synthesis scheme (S-6) is shown below.

[0091] Next, the synthesis scheme (S-7) is described. In particular, the halogenated aryl compound with a naphthalene framework (compound 5) and the amine compound with a benzonaphthofuran framework or a benzonaphthothiophene framework (compound 8) are coupled to obtain an amine compound with a naphthalene framework and a benzonaphthofuran framework or a benzonaphthothiophene framework (compound 9). The synthesis scheme (S-7) is shown below.

[0092] Next, the synthesis scheme (S-8) is described. In particular, the amine compound (compound 9) and the spirobifluorene compound (compound 2) are coupled to obtain the organic compound represented by the general formula (G1). The synthesis scheme (S-8) is shown below.

[0093] The amine compound (compound 9) in synthesis schemes (S-7) and (S-8) can also be synthesized according to synthesis scheme (S-9). Specifically, the amine compound is coupled with a naphthalene framework (compound 1) and the compound with a benzonaphthofuran framework or a benzonaphthothiophene framework (compound 4) to obtain the amine compound (compound 9). Synthesis scheme (S-9) is shown below.

[0094] In the synthesis schemes (S-1) to (S-9) X 1 up to X 3 Each represents chlorine, bromine, iodine or a triflate group independently of one another.

[0095] In the case where the Buchwald-Hartwig reaction using a palladium catalyst is employed in synthesis schemes (S-1) and (S-9), a palladium compound such as bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0) or allylpalladium(II) chloride (dimer) can be used as the palladium catalyst; Tri(tert-butyl)phosphine, tri(n-hexyl)phosphine, tricyclohexylphosphine, di(1-adamantyl)-n-butylphosphine, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, tri(ortho-tolyl)phosphine, di(tert-butyl)(1-methyl-2,2-diphenylcyclopropyl)phosphine (abbreviation: cBRIDP), or the like can be used as a ligand for the palladium catalyst. An organic base, such as sodium tert-butoxide, an inorganic base, such as potassium carbonate, cesium carbonate, or sodium carbonate, or the like can be used as the base in the reaction.A functional host compound, such as 18-crown-6-ether, can also be used in the reaction. Toluene, xylene, benzene, tetrahydrofuran, dioxane, or similar solvents can be used in the reaction.

[0096] A coupling reaction using copper or a copper compound can be employed for each of the synthesis schemes (S-1) to (S-9). Examples of the base to be used include an inorganic base such as potassium carbonate. Suitable solvents for the reaction include 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU), toluene, xylene, benzene, and the like. In the coupling reaction using copper or a copper compound, the target substance can be obtained in a shorter time and in a higher yield if the reaction temperature is higher than or equal to 100 °C; therefore, DMPU or xylene, which has a high boiling point, is preferably used. A reaction temperature higher than or equal to 150 °C is more preferred, and consequently, DMPU is more preferably used.

[0097] The reagents that can be used in synthesis schemes (S-1) to (S-9) are not limited to those described above. The process for synthesizing the organic compound of the present invention, represented by the general formula (G1), is not limited to synthesis schemes (S-1) to (S-9). < <Syntheseverfahren der organischen Verbindung, die durch die allgemeine Formel (G7) dargestellt wird> >

[0098] The organic compound of the present invention, represented by the general formula (G7), can be synthesized by a process similar to the synthesis schemes (S-1) to (S-9), which are the aforementioned processes for synthesizing the organic compound represented by the general formula (G1). In particular, the synthesis schemes (S-10) to (S-16) shown below can be used for the synthesis.

[0099] In synthesis schemes (S-10) to (S-16) X 2 and X 3 like those described (shown) above, and therefore they will not be described here.

[0100] In the synthesis schemes (S-10), (S-15) and (S-16), X represents 4 represents chlorine, bromine, iodine, or a triflate group.

[0101] The same reaction conditions as those in the synthesis schemes (S-1) to (S-9) can be used in synthesis schemes (S-10) to (S-16).

[0102] The method for synthesizing the organic compound of the present invention, which is represented by the general formula (G7), is not limited to synthesis schemes (S-10) to (S-16).

[0103] The organic compounds of embodiments of the present invention can be synthesized by the above methods, however, the present invention is not limited thereto and other synthesis methods may be used.

[0104] The structures described in this embodiment can be used in a suitable combination with any of the structures described in the other embodiments. (Version 2)

[0105] This embodiment describes an organic semiconductor device of an embodiment of the present invention.

[0106] For the organic semiconductor device of an embodiment of the present invention, an organic compound can be used which is represented by the general formula (G8).

[0107] In the general formula (G8) α 1 and α 2 each independently represents a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group; n is 1 or 2; m is 0, 1 or 2; R 1 to R 7 Each independently represents hydrogen (including deuterium), a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, or a substituted or unsubstituted phenyl group; Ar 2 represents a substituted or unsubstituted benzo[b]naphtho[2,1-d]furanyl group, a substituted or unsubstituted benzo[b]naphtho[2,3-d]furanyl group, a substituted or unsubstituted benzo[b]naphtho[2,1-d]thiophenyl group, or a substituted or unsubstituted benzo[b]naphtho[2,3-d]thiophenyl group; and Ar 3 represents a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted spirobifluorenyl group. If n is 2, a variety of α can be used. 1 They can be the same or different from each other. If m is 2, a variety of α can be used. 2 be the same or different from each other.

[0108] For the organic semiconductor device of an embodiment of the present invention, an organic compound can be used which is represented by the general formula (G9).

[0109] In the general formula (G9) α 1 and α 2 each independently represents a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group; n is 1 or 2; m is 0, 1 or 2; R 1 to R 7 Each independently represents hydrogen (including deuterium), a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, or a substituted or unsubstituted phenyl group; Ar 2 represents a group defined by the general formula (Ar 2 -a) or the general formula (Ar 2 -b) is represented; one of R 8 to R 17 represents a bond; other R 8 to R 17 as the bond as well as R 18 to R 28 and R 31 to R 34 Each independently represents hydrogen (including deuterium), a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a silyl group with 3 to 18 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms; if R 29 and R 30 Each representing a bond, are R 29 and R 30 bound together to form a ring; if neither R 29 still R 30 representing a bond, R 29 and R 30 Each independently represents hydrogen (including deuterium), a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a silyl group with 3 to 18 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms; and X represents oxygen or sulfur. If n is 2, a variety of α can be 1 They can be the same or different from each other. If m is 2, a variety of α can be used. 2 be the same or different from each other.

[0110] As described above, the organic compounds represented by the general formulas (G8) and (G9) each exhibit high stability and high heat resistance due to the presence of the naphthyl group bonded to nitrogen via the phenylene or biphenyldiyl group. Consequently, a highly reliable and high-quality organic semiconductor device can be fabricated using such an organic compound.

[0111] Since the organic compound represented by each of the general formulas (G8) and (G9) comprises a benzo[b]naphtho[2,1-d]furanyl group, a benzo[b]naphtho[2,3-d]furanyl group, a benzo[b]naphtho[2,1-d]thiophenyl group, or a benzo[b]naphtho[2,3-d]thiophenyl group bonded directly or via an arylene group to nitrogen, the operating voltage of the organic semiconductor device comprising the organic compound can be prevented from changing significantly over its operating time. Furthermore, the organic semiconductor device can exhibit a long operating lifetime.

[0112] The organic compounds represented by the general formulas (G8) and (G9) can have a low sublimation temperature, which prevents thermal decomposition during sublimation.

[0113] The specific examples of substituents that can be used in the organic compounds represented by the general formulas, as described in embodiment 1, can also be applied to the organic compounds represented by the general formulas (G8) and (G9).

[0114] Specific examples of the organic compounds represented by the general formulas (G8) and (G9) include organic compounds represented by the structural formulas (300) to (344) shown below. It should be noted that the organic compounds represented by the general formulas (G8) and (G9) are not limited to those represented by the structural formulas shown below.

[0115] For the organic semiconductor device of an embodiment of the present invention, any of the organic compounds described in embodiment 1, represented by the general formulas (G1) to (G7), can be used.

[0116] The organic compound represented by any of the general formulas (G1) to (G9) is suitable for use in a light-emitting device of organic semiconductor devices, such as an organic light-emitting diode (OLED), and can also be used for other organic semiconductor devices. Examples of further applications include photoelectric conversion devices, such as an organic optical sensor and an organic thin-film solar cell, an organic field-effect transistor, a semiconductor gas sensor, a diode, an inverter, and a storage device.

[0117] Fig. 1A to Fig. Figure 1C are cross-sectional views showing a light-emitting device, a photoelectric conversion device and an organic field-effect transistor, each of which is an example of the organic semiconductor device of an embodiment of the present invention.

[0118] Fig. Figure 1A shows a cross-sectional view of a light-emitting device 100. The light-emitting device 100 comprises a first electrode 101 and a second electrode 102, which are provided over a substrate 160, and an organic compound layer 103A, which is positioned between the first electrode 101 and the second electrode 102. One of the first electrode 101 and the second electrode 102 serves as the anode, and the other serves as the cathode. The organic compound layer 103A comprises a light-emitting layer 113, and the light-emitting layer 113 contains a light-emitting material. When a voltage is applied between the first electrode 101 and the second electrode 102, light is emitted by the organic compound layer 103A; therefore, the light-emitting device 100 can be used as an organic light-emitting diode.Although not shown, the organic compound layer 103A can, in addition to the light-emitting layer 113, comprise various layers, such as a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, a charge generation layer, and a cap layer. The organic compound layer 103A can comprise a variety of the light-emitting layers 113. In this description, the organic compound layer contained in the light-emitting device 100 is referred to in some cases as the EL layer.The organic compound represented by any of the general formulas (G1) to (G9) can be used among the layers contained in the organic compound layer 103A in the light-emitting layer 113, the hole injection layer, the hole transport layer, the electron blocking layer, the cap layer and the like.

[0119] In the organic compound layer 103A of the light-emitting device 100, the organic compound represented by any of the general formulas (G1) to (G9) is preferably contained in a layer positioned between the light-emitting layer 113 and the anode (the first electrode 101 or the second electrode 102). Here, the layer between the light-emitting layer 113 and the anode is referred to as the first layer. Specific examples of the first layer include a hole injection layer, a hole transport layer, and an electron blocking layer. The organic compound represented by any of the general formulas (G1) to (G9) exhibits high hole transport properties and can therefore be suitably used in the first layer.

[0120] The organic compound represented by any one of the general formulas (G1) to (G9) exhibits a high LUMO level and high electron stability. Therefore, when the first layer containing the organic compound is in contact with the surface of the light-emitting layer 113 on the anode side, degradation of the other layers due to electrons passing from the light-emitting layer 113 to the anode side can be prevented, thus improving the reliability of the light-emitting device 100. Furthermore, since the first layer containing the organic compound represented by any one of the general formulas (G1) to (G9) has a stable film quality, the film quality of the light-emitting layer 113 in contact with the first layer cannot become unstable, thus improving the reliability of the light-emitting device 100.

[0121] It is preferred that the first layer contains the organic compound represented by any of the general formulas (G1) to (G9) in the case where the light-emitting layer 113 has a structure in which exciplex triplet energy transfer (ExTET), i.e., energy transfer from an exciplex to a light-emitting substance, is utilized. It is particularly preferred that the first layer contains the organic compound represented by any of the general formulas (G1) to (G9) in the case where the light-emitting layer 113 comprises a first host material, a second host material, and a light-emitting substance, the first and second host materials together form an exciplex, and the difference between the peak wavelengths of the emission spectra of the exciplex and the light-emitting substance is less than or equal to 30 nm.Since the organic compound represented by any of the general formulas (G1) to (G9) has a high T1 level, the efficiency of energy transfer from the exciplex to the light-emitting substance can be increased by using the organic compound in the first layer. Since the organic compound represented by any of the general formulas (G1) to (G9) has high electron stability, it is particularly preferred that the first layer containing the organic compound be placed in contact with the light-emitting layer 113 to improve the reliability of the light-emitting device 100.

[0122] In the case where the light-emitting layer 113 has the structure in which ExTET is used, which is the energy transfer from the exciplex to the light-emitting substance, and the light-emitting substance emits red light or green light, the first layer containing the organic compound represented by any of the general formulas (G1) to (G9) is expected to achieve a more efficient energy transfer from the exciplex to the light-emitting substance.

[0123] For example, comparing the emission spectra of the first host material, the second host material, and a mixture of these materials can confirm whether the first and second host materials form an exciplex by observing a phenomenon where the emission spectrum of the mixture shifts towards the longer wavelength side than the emission spectrum of any single material (or exhibits an additional peak on the longer wavelength side). Alternatively, comparing the transient PL lifetimes of the first host material, the second host material, and the mixture of these materials can confirm this by observing a difference in the transient response, such as a phenomenon where the transient PL lifetime of the mixture exhibits longer-life components or a larger proportion of delay components than that of any single material.The transient PL can be reformulated as transient electroluminescence (EL). This means that the formation of an exciplex can also be confirmed by a difference in the transient reaction, which is observed by comparing the transient EL of the first host material, the second host material, and the mixed film of these materials.

[0124] It is more preferred that, in the case where the light-emitting layer 113 contains a fluorescent substance, the first layer contains the organic compound represented by any one of the general formulas (G1) to (G9). It is more preferred, in particular, that, in the case where the light-emitting layer 113 contains a host material and a fluorescent substance, the first layer contains the organic compound represented by any one of the general formulas (G1) to (G9). It is even more preferred that, in the case where the light-emitting layer 113 contains a type of host material and a fluorescent substance, the first layer contains the organic compound represented by any one of the general formulas (G1) to (G9).In the case where the light-emitting layer 113 contains a host material and a fluorescent substance, there is a tendency for electrons to pass from the light-emitting layer 113 to the anode side in some cases. If the organic compound, represented by any of the general formulas (G1) to (G9), which has a high LUMO level and high electron resistance, is used in the first layer in contact with the light-emitting layer 113, degradation of the other layers due to electrons passing from the light-emitting layer 113 to the anode side can be prevented, thus improving the reliability of the light-emitting device 100.

[0125] Fig. Figure 1B is a cross-sectional view of a photoelectric conversion device 500. The photoelectric conversion device 500 comprises a first electrode 501 and a second electrode 502 provided above the substrate 160, and an organic compound layer 503 positioned between the first electrode 501 and the second electrode 502. The organic compound layer 503 includes a photoelectric conversion layer 513, and the photoelectric conversion layer 513 contains a photoelectric conversion material. Examples of the photoelectric conversion material include inorganic semiconductors, such as silicon, and organic semiconductors, such as organic compounds.The photoelectric conversion device 500 can generate electrical charges from light incident on the organic compound layer 503 and extract the electrical charge as current; therefore, the photoelectric conversion device 500 can be used for an organic optical sensor, an organic solar cell, or the like. It should be noted that a voltage can be applied between the first electrode 501 and the second electrode 502. Although not shown, the organic compound layer 503 can, in addition to the photoelectric conversion layer 513, comprise various layers, such as a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, and a charge generation layer. The organic compound layer 503 can comprise a variety of the photoelectric conversion layers 513.The organic compound represented by any of the general formulas (G1) to (G9) can be used among the layers contained in the organic compound layer 503 for the photoelectric conversion layer 513, the hole injection layer, the hole transport layer, the electron blocking layer and the like.

[0126] Fig. Figure 1C is a cross-sectional view of an organic field-effect transistor 520. The organic field-effect transistor 520 comprises a gate electrode 521 provided over the substrate 160, a gate insulating layer 522 over the gate electrode, an organic compound layer 523 over the gate insulating layer 522, and an electrode 524 and an electrode 525 over the organic compound layer 523. The electrode 524 serves as one of the source and drain electrodes, and the electrode 525 serves as the other of the source and drain electrodes. For the organic compound layer 523, any of the general formulas (G1) to (G9) can be used. Fig. While the present invention is not limited to the organic field-effect transistor 520, which is a top-contact-bottom-gate type, as defined in Figure 1C, the organic field-effect transistor 520 may, for example, have a bottom-contact-bottom-gate type structure, a bottom-contact-top-gate type structure, a top-contact-top-gate type structure, a top-bottom contact structure, a vertical metal-base structure, or a vertical floating-metal structure.

[0127] When the organic compound represented by any of the general formulas (G1) to (G9) is used for the organic compound layer 103A of the light-emitting device 100, the organic compound layer 503 of the photoelectric conversion device 500, and the organic compound layer 523 of the organic field-effect transistor 520, holes in the organic compound layers can be readily transferred. Furthermore, highly reliable organic semiconductor devices of high quality can be produced. In addition, the service life of the organic semiconductor devices can be extended, i.e., their reliability can be increased. Finally, the power consumption of the organic semiconductor devices can be reduced.

[0128] Next, a device 810 is described in which the light-emitting device 100 and the photoelectric conversion device 500 are provided on the same plane. Fig. Figure 2A represents the device 810, which comprises a light-emitting device 100a and a photoelectric conversion device 500a over a substrate 800. Although not shown, the device 810 can be provided with a partition in a region surrounded by the substrate 800, the first electrode 101, the organic compound layer 103A, a second electrode 802, the organic compound layer 503, and the first electrode 501. By providing the partition, a short circuit between the devices can be prevented. This can also prevent the formation of an irregularity in the second electrode 802 and thus prevent problems such as a connection failure.

[0129] It should be noted that in device 810, the light-emitting device 100a is used as an organic light-emitting diode (OLED), and the photoelectric conversion device 500a is used as an organic optical sensor. The light-emitting device 100a and the photoelectric conversion device 500a are formed on the same substrate. Therefore, device 810 can have a structure in which an organic optical sensor is incorporated into a display device comprising an organic light-emitting diode, thus enabling device 810 to have a function for displaying an image using the light-emitting device 100a and a function for performing the imaging and detection using the photoelectric conversion device 500a.The organic semiconductor device, whose thickness and weight can be easily reduced, whose surface area can be easily enlarged, and which has a high degree of freedom of shape and design, can be used in various display devices.

[0130] Specific examples of light detected by the photoelectric conversion device 500a include visible light and infrared light. In this description and the like, a blue (B) wavelength range is greater than or equal to 400 nm and less than 490 nm, and blue (B) light has at least one emission spectrum peak in that wavelength range. A green (G) wavelength range is greater than or equal to 490 nm and less than 580 nm, and green (G) light has at least one emission spectrum peak in that wavelength range. A red (R) wavelength range is greater than or equal to 580 nm and less than 700 nm, and red (R) light has at least one emission spectrum peak in that wavelength range.In this description and the like, a wavelength range of visible light is greater than or equal to 400 nm and less than 700 nm, and visible light exhibits at least one emission spectrum peak in that wavelength range. An infrared (IR) wavelength range is greater than or equal to 700 nm and less than 900 nm, and infrared (IR) light exhibits at least one emission spectrum peak in that wavelength range.

[0131] In device 810, the first electrode 101 and the first electrode 501 are provided on the same level. Fig. In step 2A, the first electrodes 101 and 501 are provided over the substrate 800. The first electrodes 101 and 501 can be formed, for example, by processing a conductive film formed over the substrate 800 into island shapes. In other words, the first electrodes 101 and 501 can be formed by the same process.

[0132] Substrate 800 can be a substrate with sufficient heat resistance to withstand the formation of the light-emitting device 100a and the photoelectric conversion device 500a. If an insulating substrate is used, a glass substrate, a quartz substrate, a sapphire substrate, a ceramic substrate, an organic resin substrate, or the like can be used as substrate 800. Alternatively, a semiconductor substrate, such as a monocrystalline or polycrystalline semiconductor substrate made of silicon, silicon carbide, or the like, a compound semiconductor substrate made of silicon germanium or the like, an SOI substrate, or the like, can be used.

[0133] Substrate 800 is particularly preferably the insulating substrate or the semiconductor substrate on which a semiconductor circuit comprising a semiconductor element, such as a transistor, is formed. The semiconductor circuit preferably forms a pixel circuit, a gate driver circuit, a source driver circuit, or the like. In addition to the above, an arithmetic circuit, a memory circuit, or the like may be formed.

[0134] Among the electrodes contained in the light-emitting device 100a and the photoelectric conversion device 500a, a conductive film that transmits visible and infrared light is used as an electrode through which light is emitted or incident. A conductive film that reflects visible and infrared light is preferably used as an electrode through which no light is emitted or incident.

[0135] In the device 810, the second electrode 802 serves as the second electrode of each of the light-emitting device 100a and the photoelectric conversion device 500a.

[0136] The relationship between the potentials of the electrodes is described in the case where the first electrode 101 of the light-emitting device 100a has a potential higher than that of the second electrode 802. In this case, the first electrode 101 serves as the anode of the light-emitting device 100a, and the second electrode 802 serves as the cathode of the light-emitting device 100a. The first electrode 501 of the photoelectric conversion device 500a has a potential lower than that of the second electrode 802. This means that when a first potential, a second potential, and a third potential are applied to the first electrode 101, the second electrode 802, and the first electrode 501, respectively, the first potential is higher than the second potential, and the second potential is higher than the third potential.

[0137] Next, the case is described in which the first electrode 101 of the light-emitting device 100a has a potential lower than that of the second electrode 802. In this case, the first electrode 101 serves as the cathode of the light-emitting device 100a, and the second electrode 802 serves as the anode of the light-emitting device 100a. The first electrode 501 of the photoelectric conversion device 500a has a potential lower than that of the second electrode 802 and a potential higher than that of the first electrode 101. This means that when the first electrode 101, the second electrode 802, and the first electrode 501 are supplied with the first potential, the second potential, and the third potential, respectively, the second potential is higher than the third potential, and the third potential is higher than the first potential.

[0138] In device 810, the organic compound represented by any of the general formulas (G1) to (G9) is preferably used for the organic compound layer 103A and / or the organic compound layer 503. In this case, holes in the organic compound layer 103A and the organic compound layer 503 can be readily transferred. Furthermore, the light-emitting device 100a and the photoelectric conversion device 500a can be very reliable, high-quality organic semiconductor devices. Additionally, the service life of the light-emitting device 100a and the photoelectric conversion device 500a can be extended, i.e., their reliability can be improved.The process in which a hole injection layer of organic compound layer 103A and a hole injection layer of organic compound layer 503 are formed collectively, and the process in which a hole transport layer of organic compound layer 103A and a hole transport layer of organic compound layer 503 are formed collectively, can simplify a process and reduce production costs, which is preferred in mass production.

[0139] Fig. 2B represents a device 810A, which is a variation of device 810. Device 810A differs from device 810 in that the organic compound layer 103A and the organic compound layer 503 comprise a common layer 806 and a common layer 807. In the light-emitting device 100a, the common layers 806 and 807 serve as part of the organic compound layer 103A. In the photoelectric conversion device 500a, the common layers 806 and 807 serve as part of the organic compound layer 503. The common layer 806 comprises, for example, a hole injection layer and a hole transport layer. The common layer 807 comprises, for example, an electron transport layer and an electron injection layer.

[0140] With the shared layers 806 and 807, a photoelectric conversion device can be incorporated into the device 810 without significantly increasing the number of separate device formations, thereby enabling the high-throughput production of the device 810A.

[0141] In device 810A, the organic compound represented by any of the general formulas (G1) to (G9) is preferably used for the common layer 806. Consequently, holes can be easily transferred between the organic compound layer 103A and the organic compound layer 503. Furthermore, the light-emitting device 100a and the photoelectric conversion device 500a can be very reliable, high-quality organic semiconductor devices. Additionally, the service life of the light-emitting device 100a and the photoelectric conversion device 500a can be extended, i.e., their reliability can be improved.

[0142] The resolution of the photoelectric conversion devices 500a described in this embodiment can, for example, be set to a resolution higher than or equal to 100 ppi, preferably higher than or equal to 200 ppi, more preferably higher than or equal to 300 ppi, even more preferably higher than or equal to 400 ppi, and even more preferably higher than or equal to 500 ppi, and lower than or equal to 2000 ppi, lower than or equal to 1000 ppi, or lower than or equal to 600 ppi. In particular, when the photoelectric conversion devices 500a are arranged with a resolution higher than or equal to 200 ppi and lower than or equal to 600 ppi, preferably higher than or equal to 300 ppi and lower than or equal to 600 ppi, the device can be used suitablely for imaging a fingerprint.In fingerprint authentication using a light-emitting and light-receiving device of an embodiment of the present invention, the increased resolution of the photoelectric conversion device 500a enables, for example, the extraction of fingerprint minutiae with high accuracy; therefore, the accuracy of fingerprint authentication can be increased. The resolution is preferably higher than or equal to 500 ppi, in which case the authentication conforms to the standard of the National Institute of Standards and Technology (NIST) or the like. Assuming that the resolution at which the photoelectric conversion devices are arranged is 500 ppi, the size of each pixel is 50.8 µm, which is sufficient for imaging the spacing of fingerprint ridges (typically greater than or equal to 300 µm and less than or equal to 500 µm).

[0143] The structures described in this embodiment can be used in a suitable combination with any of the structures described in the other embodiments. (Version 3)

[0144] In this embodiment, structures of the organic semiconductor devices of an embodiment of the present invention are designed using Fig. 3A to Fig. 3F described. <<Grundlegende Struktur der Licht emittierenden Vorrichtung> >

[0145] A basic structure of a light-emitting device is described. Fig. 3A represents a light-emitting device comprising an EL layer, which in turn comprises a light-emitting layer, between a pair of electrodes. Specifically, the organic compound layer 103 is positioned between the first electrode 101 and the second electrode 102. It should be noted that the organic compound layer 103 can also be referred to as the EL layer.

[0146] Fig. 3B represents a light-emitting device having a multilayer structure (tandem structure) in which a plurality of EL layers (two EL layers 103a and 103b in Fig. 3B) is provided between a pair of electrodes and a charge-generating layer 106 is provided between the EL layers. A light-emitting device with a tandem structure enables the fabrication of a display device that exhibits high efficiency without changing the amount of current.

[0147] The charge-generating layer 106 has a function for injecting electrons into one of the EL layers 103a and 103b and for injecting holes into the other of the EL layers 103a and 103b when a potential difference is created between the first electrode 101 and the second electrode 102. Therefore, the charge-generating layer 106 injects electrons into the organic compound layer 103a and holes into the organic compound layer 103b when in Fig. 3B a voltage is applied such that the potential of the first electrode 101 is higher than that of the second electrode 102.

[0148] It should be noted that, with regard to light extraction efficiency, the charge-generating layer 106 preferably has a visible light transmittance (in particular, the charge-generating layer 106 preferably has a visible light transmittance of 40% or more). The charge-generating layer 106 functions even if it has a lower conductivity than the first electrode 101 or the second electrode 102.

[0149] Fig. Figure 3C describes a multilayer structure of the organic compound layer 103 in the light-emitting device of an embodiment of the present invention. In this case, the first electrode 101 is considered to serve as the anode and the second electrode 102 is considered to serve as the cathode. The organic compound layer 103 has a structure in which a hole injection layer 111, a hole transport layer 112, the light-emitting layer 113, an electron transport layer 114, and an electron injection layer 115 are arranged in that order over the first electrode 101. It should be noted that the light-emitting layer 113 can have a multilayer structure consisting of a plurality of light-emitting layers that emit light of different colors.For example, a light-emitting layer containing a light-emitting substance that emits red light, a light-emitting layer containing a light-emitting substance that emits green light, and a light-emitting layer containing a light-emitting substance that emits blue light can be stacked on top of each other, with one or no layer containing a charge carrier transport material between them. Alternatively, a light-emitting layer containing a light-emitting substance that emits yellow light and a light-emitting layer containing a light-emitting substance that emits blue light can be used in combination. It should be noted that the multilayer structure of the light-emitting layer 113 is not limited to the above.For example, the light-emitting layer 113 can have a multilayer structure consisting of a multitude of light-emitting layers emitting light of the same color. For example, a first light-emitting layer containing a light-emitting substance that emits blue light and a second light-emitting layer containing a light-emitting substance that emits blue light can be stacked on top of each other, with one or no layer containing a charge carrier transport material between them. The structure in which a multitude of light-emitting layers emitting light of the same color are stacked on top of each other can extend the service life; in other words, the structure can achieve higher reliability in some cases than a single-layer structure. In the case where a multitude of EL layers are stacked, as in the one in . Fig. As provided in the tandem structure shown in Figure 3B, the layers in each EL layer are arranged sequentially from the anode side, as described above. If the first electrode 101 is the cathode and the second electrode 102 is the anode, the order of the layers in the organic compound layer 103 is reversed. Specifically, layer 111 above the first electrode 101, which serves as the cathode, is an electron injection layer; layer 112 is an electron transport layer; layer 113 is a light-emitting layer; layer 114 is a hole transport layer; and layer 115 is a hole injection layer.

[0150] The light-emitting layer 113, contained within the EL layers (103, 103a, and 103b), comprises a suitable combination of a light-emitting substance and a variety of other substances, such that fluorescent light of a desired color or phosphorescent light of a desired color can be obtained. The variety of EL layers (103a and 103b) in Fig. 3B can exhibit their respective emission colors. In this case, the light-emitting substances and other substances between the light-emitting layers can differ.

[0151] The light-emitting device of an embodiment of the present invention may have an optical microresonator (microcavity) structure, for example, in Fig. 3C the first electrode 101 is a reflective electrode and the second electrode 102 is a transflective electrode. Therefore, light from the light-emitting layer 113 in the organic compound layer 103 between the electrodes can be brought into resonance, and light emitted via the second electrode 102 can be amplified.

[0152] It should be noted that if the first electrode 101 of the light-emitting device is a reflective electrode having a multilayer structure consisting of a reflective conductive material and a translucent conductive material (a transparent conductive film), optical adjustment can be achieved by controlling the thickness of the transparent conductive film. In particular, if the wavelength of light received from the light-emitting layer 113 is λ, the optical path length between the first electrode 101 and the second electrode 102 (the product of the thickness and the refractive index) is preferably set to mλ / 2 (where m is an integer of 1 or more) or a value close to mλ / 2.

[0153] To amplify the desired light (wavelength: λ) received from the light-emitting layer 113, the optical path length from the first electrode 101 to a region of the light-emitting layer 113 in which the desired light is received (light-emitting region), and the optical path length from the second electrode 102 to the region of the light-emitting layer 113 in which the desired light is received (light-emitting region), are preferably set to (2m'+1)λ / 4 (m' is an integer of 1 or more) or a value close to (2m'+1)λ / 4. Here, the light-emitting region denotes a region of the light-emitting layer 113 in which holes and electrons recombine.

[0154] By such an optical adjustment, the spectrum of specific monochromatic light obtained from the light-emitting layer 113 can be narrowed and light emission with high color purity can be obtained.

[0155] In the above case, the optical path length between the first electrode 101 and the second electrode 102 is, more precisely, the total thickness from a reflection region of the first electrode 101 to a reflection region of the second electrode 102. However, it is difficult to determine the reflection regions of the first electrode 101 and the second electrode 102 precisely; therefore, it is assumed that the above effect can be sufficiently obtained regardless of where the reflection regions of the first electrode 101 and the second electrode 102 are placed. Furthermore, the optical path length between the first electrode 101 and the light-emitting layer that emits the desired light is, more precisely, the optical path length between the reflection region of the first electrode 101 and the light-emitting region of the light-emitting layer that emits the desired light.However, it is difficult to determine exactly the reflection area of ​​the first electrode 101 and the light-emitting area of ​​the light-emitting layer that emits the desired light; therefore, it is assumed that the above effect can be sufficiently obtained regardless of where the reflection area and the light-emitting area of ​​the first electrode 101 and the light-emitting layer that emits the desired light are placed.

[0156] Fig. 3D represents a modification example of the multilayered structure in Fig. 3C. In this case as well, the first electrode 101 is considered to serve as the anode and the second electrode 102 as the cathode. In this modification example, the hole transport layer 112 and the electron transport layer 114 each have a multilayer structure consisting of two layers. In other words, the organic compound layer 103 has a structure in which a hole injection layer 111, a first hole transport layer 112-1, a second hole transport layer 112-2, a light-emitting layer 113, a second electron transport layer 114-2, a first electron transport layer 114-1, and an electron injection layer 115 are arranged one above the other in that order above the first electrode 101. It should be noted that the light-emitting layer 113 is positioned between the first electrode 101 and the second electrode 102.The first hole transport layer 112-1 is positioned between the first electrode 101 and the light-emitting layer 113. The first electron transport layer 114-1 is positioned between the light-emitting layer 113 and the second electrode 102. The hole injection layer 111 is positioned between the first electrode 101 and the hole transport layer 112. The electron injection layer 115 is positioned between the electron transport layer 114 and the second electrode 102. The second hole transport layer 112-2 is positioned between the first hole transport layer 112-1 and the light-emitting layer 113. In other words, the second electron transport layer 114-2 is positioned between the light-emitting layer 113 and the first electron transport layer 114-1.In the case where the organic compound layer 103 has such a multilayer structure, one or more of the hole injection layer 111, the hole transport layer 112 and the light emitting layer 113 preferably contain the organic compound represented by any of the general formulas (G1) to (G9).

[0157] The second hole transport layer 112-2 is provided to prevent, for example, electrons from passing from the light-emitting layer 113 to the side of the first electrode 101. Accordingly, the second hole transport layer 112-2 can also be referred to as an electron-blocking layer. It is particularly preferred that the second hole transport layer 112-2, in contact with the light-emitting layer 113, contains the organic compound represented by any of the general formulas (G1) to (G9). The second electron transport layer 114-2 is provided, for example, to prevent holes from passing from the light-emitting layer 113 to the side of the second electrode 102. Accordingly, the second electron transport layer 114-2 can also be referred to as a hole-blocking layer.

[0158] The in Fig. The light-emitting device shown in Figure 3E is a tandem-structured light-emitting device. Due to its microcavity structure, light (monochromatic light) of different wavelengths can be extracted from the EL layers (103a and 103b). Therefore, it is unnecessary to form separate EL layers to obtain a variety of emission colors (e.g., red, green, and blue). Consequently, high resolution can be easily achieved. A combination with color layers (color filters) is also possible. Furthermore, the emission intensity of light with a specific wavelength can be increased in the forward direction, thereby reducing power consumption.

[0159] The in Fig. The light-emitting device shown in Figure 3F is an example of the one described in Figure 3F. Fig. 3B shows a light-emitting device with the tandem structure and includes, as in Fig. Figure 3F shows three EL layers (103a, 103b, and 103c) arranged one above the other, with charge-generating layers (106a and 106b) positioned between them. The three EL layers (103a, 103b, and 103c) each comprise light-emitting layers (113a, 113b, and 113c), and the emission colors of the light-emitting layers can be freely chosen. For example, light-emitting layer 113a can emit blue light, light-emitting layer 113b can emit red light, green light or yellow light and light-emitting layer 113c can emit blue light, or light-emitting layer 113a can emit red light, light-emitting layer 113b can emit blue light, green light or yellow light, and light-emitting layer 113c can emit red light.

[0160] In the light-emitting device of an embodiment of the present invention, the first electrode 101 and / or the second electrode 102 are translucent electrodes (e.g., transparent electrodes or transflective electrodes). In the case of a transparent electrode, the transparent electrode has a visible light transmittance of 40% or higher. In the case of a translucent electrode, the transflective electrode has a visible light reflectance of 20% or higher and 80% or lower, preferably 40% or higher and 70% or lower. These electrodes preferably have a resistivity of 1 × 10⁻⁶ -2 Ωcm or less.

[0161] If, in the light-emitting device of an embodiment of the present invention, either the first electrode 101 or the second electrode 102 is a reflective electrode, the reflectance for visible light of the reflective electrode is greater than or equal to 40% and less than or equal to 100%, preferably greater than or equal to 70% and less than or equal to 100%. This electrode preferably has a resistivity of 1 × 10 -2 Ωcm or less. <<Spezifische Struktur der Licht emittierenden Vorrichtung> >

[0162] Next, a specific structure of the light-emitting device of an embodiment of the present invention will be described. The description will be given using… Fig. 3E, which represents the tandem structure, was carried out. It should be noted that the structure of the EL layer is also applicable to the structure of light-emitting devices with a single-layer structure in Fig. 3A and Fig. 3C applies. If the light-emitting device is in Fig. Since electrode 3E has a microcavity structure, the first electrode 101 is configured as a reflective electrode and the second electrode 102 is configured as a transflective electrode. Therefore, a single-layer or multi-layer structure can be formed using one or more types of desired electrode materials. It should be noted that the second electrode 102 is formed after the organic compound layer 103b has been formed, using a suitably selected material. <Erste Elektrode und zweite Elektrode>

[0163] Any of the following materials, in a suitable combination, can be used for the first electrode 101 and the second electrode 102, provided that the aforementioned functions of the electrodes can be fulfilled. For example, a metal, an alloy, an electrically conductive compound, a mixture of these, and the like can be appropriately used. In particular, an In-Sn oxide (also known as ITO), an In-Si-Sn oxide (also known as ITSO), an In-Zn oxide, or an In-W-Zn oxide can be used. Furthermore, it is possible to use a metal, such as... B. 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) or neodymium (Nd), or an alloy containing a suitable combination of any of these metals.It is also possible to use an element of Group 1 or an element of Group 2 of the periodic table that have not been described above (e.g. lithium (Li), cesium (Cs), calcium (Ca) or strontium (Sr)), a rare earth metal such as europium (Eu) or ytterbium (Yb), an alloy containing a suitable combination of any of these elements, graphene or the like.

[0164] In the light-emitting device in Fig. In step 3E, when the first electrode 101 is the anode, a hole injection layer 111a and a hole transport layer 112a of the organic compound layer 103a are sequentially arranged over the first electrode 101 by a vacuum evaporation process. After the organic compound layer 103a and the charge generation layer 106 have been formed, a hole injection layer 111b and a hole transport layer 112b of the organic compound layer 103b are similarly sequentially arranged over the charge generation layer 106.

[0165] The in Fig. The light-emitting device shown in Figure 3E can have an optical microresonator (microcavity) structure if the first electrode 101 is a reflective electrode and the second electrode 102 is a transflective electrode. Therefore, light from the light-emitting layer 113 in the organic compound layer 103 between the electrodes can be brought into resonance, and light emitted via the second electrode 102 can be amplified.

[0166] It should be noted that if the first electrode 101 of the light-emitting device is a reflective electrode having a multilayer structure consisting of a reflective conductive material and a translucent conductive material (a transparent conductive film), optical adjustment can be achieved by controlling the thickness of the transparent conductive film. In particular, if the wavelength of light received from the light-emitting layer 113 is λ, the optical path length between the first electrode 101 and the second electrode 102 (the product of the thickness and the refractive index) is preferably set to mλ / 2 (where m is an integer of 1 or more) or a value close to mλ / 2.

[0167] To amplify the desired light (wavelength: λ) received from the light-emitting layer 113, the optical path length from the first electrode 101 to a region of the light-emitting layer 113 in which the desired light is received (light-emitting region), and the optical path length from the second electrode 102 to the region of the light-emitting layer 113 in which the desired light is received (light-emitting region), are preferably set to (2m'+1)λ / 4 (m' is an integer of 1 or more) or a value close to (2m'+1)λ / 4. Here, the light-emitting region denotes a region of the light-emitting layer 113 in which holes and electrons recombine.

[0168] By such an optical adjustment, the spectrum of specific monochromatic light obtained from the light-emitting layer 113 can be narrowed and light emission with high color purity can be obtained.

[0169] In the above case, the optical path length between the first electrode 101 and the second electrode 102 is, more precisely, the total thickness from a reflection region of the first electrode 101 to a reflection region of the second electrode 102. However, it is difficult to determine the reflection regions of the first electrode 101 and the second electrode 102 precisely; therefore, it is assumed that the above effect can be sufficiently obtained regardless of where the reflection regions of the first electrode 101 and the second electrode 102 are placed. Furthermore, the optical path length between the first electrode 101 and the light-emitting layer that emits the desired light is, more precisely, the optical path length between the reflection region of the first electrode 101 and the light-emitting region of the light-emitting layer that emits the desired light.However, it is difficult to precisely determine the reflection area of ​​the first electrode 101 and the light-emitting area of ​​the light-emitting layer that emits the desired light; therefore, it is assumed that the above effect can be sufficiently obtained regardless of where the reflection area and the light-emitting area of ​​the first electrode 101 and the light-emitting layer that emits the desired light are placed.

[0170] In the light-emitting device of an embodiment of the present invention, the first electrode 101 and / or the second electrode 102 are translucent electrodes (e.g., transparent electrodes or transflective electrodes). In the case of a transparent electrode, the transparent electrode has a visible light transmittance of 40% or higher. In the case of a translucent electrode, the transflective electrode has a visible light reflectance of 20% or higher and 80% or lower, preferably 40% or higher and 70% or lower. These electrodes preferably have a resistivity of 1 × 10⁻⁶ -2 Ωcm or less.

[0171] If, in the light-emitting device of an embodiment of the present invention, either the first electrode 101 or the second electrode 102 is a reflective electrode, the reflectance for visible light of the reflective electrode is greater than or equal to 40% and less than or equal to 100%, preferably greater than or equal to 70% and less than or equal to 100%. This electrode preferably has a resistivity of 1 × 10 -2 Ωcm or less. <lochinjektionsschicht>

[0172] The hole injection layers (111, 111a and 111b) inject holes from the first electrode 101 serving as the anode and the charge generation layers (106, 106a and 106b) into the EL layers (103, 103a and 103b) and contain an organic acceptor material and a material with a high hole injection property.

[0173] The organic acceptor material allows holes to be created in another organic compound whose HOMO level is close to the LUMO level of the organic acceptor material when charge separation is induced between the organic acceptor material and the organic compound. Therefore, a compound with an electron-withdrawing group (for example, a halogen group or a cyano group), such as a quinodimethane derivative, a chloranil derivative, or a hexaazatriphenylene derivative, can be used as the organic acceptor material.Examples of the organic acceptor material include 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ), 3,6-difluoro-2,5,7,7,8,8-hexacyanoquinodimethane, chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN), 1,3,4,5,7,8-hexafluorotetracyanonaphthoquinodimethane (abbreviation: F6-TCNNQ) and 2-(7-dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyren-2-ylidene)malononitrile. It should be noted that among organic acceptor materials, a compound in which electron-withdrawing groups are bonded to fused aromatic rings, each comprising a multitude of heteroatoms, such as HAT-CN, is particularly preferred because it exhibits high acceptor properties and stable film quality against heat. Additionally, a [3]radialene derivative with an electron-withdrawing group (in particular a cyano group or a halogen group, such as...) is preferred.a fluorine group), which has a very high electron accepting property; specific examples include α,α',α''-1,2,3-cyclopropanetriylidentris[4-cyano-2,3,5,6-tetrafluorobenzolacetonitrile], α,α',α''-1,2,3-cyclopropanetriylidentris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzolacetonitrile] and α,α',α''-1,2,3-cyclopropanetriylidentris[2,3,4,5,6-pentafluorobenzolacetonitrile].

[0174] A material with high hole injection properties can be an oxide of a metal belonging to groups 4 to 8 of the periodic table (e.g., a transition metal oxide such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, or manganese oxide). Specific examples include molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide, and rhenium oxide. Among the aforementioned oxides, molybdenum oxide is preferred because it is stable in atmospheric air, has low hygroscopic properties, and is easy to handle. Other examples include a perylenetetracarboxylic acid derivative, such as... B. Dichinoxalino[2,3-a:2',3'-c]phenazine (abbreviation: HATNA), 2,3,8,9,14,15-hexafluorodichinoxalino[2,3-a-2',3'-c]phenazine (abbreviation: HATNA-F6), 3,4,9,10-perylenetetracarboxylic diimide (abbreviation: PTCDI) or 3,4,9,10-perylenetetracarboxyl-bis-benzimidazole (abbreviation: PTCBI); (C 60 -I h )-[5,6]Fullerene (abbreviation: C 60 ); (C 70 -D 5h )-[5,6]Fullerene (abbreviation: C 70 ); an organic compound, such as phthalocyanine (abbreviation: H₂Pc); and a metal phthalocyanine containing copper, zinc, cobalt, iron, chromium, nickel, or the like, or a derivative thereof, such as copper phthalocyanine (abbreviation: CuPc), zinc phthalocyanine (abbreviation: ZnPc), cobalt phthalocyanine (abbreviation: CoPc), iron phthalocyanine (abbreviation: FePc), tin phthalocyanine (abbreviation: SnPc), tin oxide phthalocyanine (abbreviation: SnOPc), titanium oxide phthalocyanine (abbreviation: TiOPc), or vanadium oxide phthalocyanine (abbreviation: VOPc). A phthalocyanine-based metal complex, such as... B. CuPc or ZnPc, and 2,3,8,9,14,15-hexafluorodichinoxalino[2,3-a:2',3'-c]phenazine are particularly preferred. Among these materials, CuPc and ZnPc are preferred because they are inexpensive and have advantageous properties.The use of ZnPc, which has a low diffusion coefficient with respect to silicon, reduces the likelihood that metal diffusion into a semiconductor will adversely affect the semiconductor properties; therefore, ZnPc is particularly suitable for a display device manufactured using a silicon semiconductor.

[0175] Other examples include aromatic amine compounds, which are low-molecular-weight compounds, such as... B. 4,4',4''-Tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-Tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-Bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), N,N'-Bis[4-bis(3-methylphenyl)aminophenyl]-N,N'-diphenyl-4,4'-diaminobiphenyl (abbreviation: DNTPD), 1,3,5-Tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-Bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2) and 3-[N-(1-Naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1).

[0176] Other examples include high-molecular-weight compounds (e.g., oligomers, dendrimers, and polymers), such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: poly-TPD). Alternatively, a high-molecular-weight compound to which an acid has been added can be used, such as poly(3,4-ethylenedioxythiophene) / polystyrenesulfonic acid (abbreviation: PEDOT / PSS) or polyaniline / polystyrenesulfonic acid (abbreviation: PAni / PSS).

[0177] A material with high hole injection properties can be a mixed material containing a hole transport material and the organic acceptor material (electron acceptor material) described above. In this case, the organic acceptor material extracts electrons from the hole transport material, creating holes in the hole injection layer 111. These holes are then injected through the hole transport layer 112 into the light-emitting layer 113. It should be noted that the hole injection layer 111 can be configured as a single-layer structure using a mixed material containing a hole transport material and an organic acceptor material (electron acceptor material), or as a multi-layer structure consisting of a layer containing a hole transport material and a layer containing an organic acceptor material (electron acceptor material).

[0178] The hole transport material preferably has a hole mobility of higher than or equal to 1 × 10 -6 cm 2 / Vs in the case where the square root of the electric field strength [V / cm] is 600. It should be noted that other substances can also be used, as long as the substances have higher hole transport properties than electron transport properties.

[0179] Materials with high hole transport properties, such as a compound with a π-electron-rich heteroaromatic ring (e.g., a carbazole derivative, a furan derivative, and a thiophene derivative) and an aromatic amine (an organic compound with an aromatic amine skeleton), are preferred as hole transport materials. The organic compound described in embodiments 1 and 2 exhibits hole transport properties and can be used as a hole transport material.

[0180] Examples of the carbazole derivative (an organic compound with a carbazole ring) include a bicarbazole derivative (e.g., a 3,3'-bicarbazole derivative) and an aromatic amine with a carbazolyl group.

[0181] Specific examples of the bicarbazole derivative (e.g., a 3,3'-bicarbazole derivative) include 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 9,9'-bis(biphenyl-4-yl)-3,3'-bi-9H-carbazole (abbreviation: BisBPCz), 9,9'-bis(biphenyl-3-yl)-3,3'-bi-9H-carbazole (abbreviation: BismBPCz), 9-(biphenyl-3-yl)-9'-(biphenyl-4-yl)-9H,9'H-3,3'-bicarbazole (abbreviation: mBPCCBP), and 9-(2-naphthyl)-9'-phenyl-9H,9'H-3,3'-bi-9H-carbazole (abbreviation: βNCCP).

[0182] Spezifische Beispiele für das aromatische Amin mit einer Carbazolyl-Gruppe umfassen 4-Phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamin (Abkürzung: PCBA1BP), N-(Biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazol-3-amin (Abkürzung: PCBiF), N-(Biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amin (Abkürzung: PCBBiF), N-[4-(9-Phenyl-9H-carbazol-3-yl)phenyl]bis(9,9-dimethyl-9H-fluoren-2-yl)amin (Abkürzung: PCBFF), N-(1,1'-Biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-4-amin, N-[4-(9-Phenyl-9H-carbazol-3-yl)phenyl]-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-4-amin, N-(1,1'-Biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-diphenyl-9H-fluoren-2-amin, N-(1,1'-Biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-diphenyl-9H-fluoren-4-amin, N-(1,1'-Biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi(9H-fluoren)-2-amin, N-(1,1'-Biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi(9H-fluoren)-4-amin, N-[4-(9-Phenyl-9H-carbazol-3-yl)phenyl]-N-(1,1':3',1''-terphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amin, N-[4-(9-Phenyl-9H-carbazol-3-yl)phenyl]-N-(1,1':4',1''-terphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amin, N-[4-(9-Phenyl-9H-carbazol-3-yl)phenyl]-N-(1,1':3',1 „-terphenyl-4-yl)-9,9-dimethyl-9H-fluoren-4-amin, N-[4-(9-Phenyl-9H-carbazol-3-yl)phenyl]-N-(1,1':4',1"-terphenyl-4-yl)-9,9-dimethyl-9H-fluoren-4-amin, 4,4'-Diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamin (Abkürzung: PCBBi1BP), 4-(1-Naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamin (Abkürzung: PCBANB), 4,4'-Di(1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamin (Abkürzung: PCBNBB), 4-Phenyldiphenyl-(9-phenyl-9H-carbazol-3-yl)amin (Abkürzung: PCA1BP), N,N'-Bis(9-phenylcarbazol-3-yl)-N,N-diphenylbenzol-1,3-diamin (Abkürzung: PCA2B), N,N',N'-Triphenyl-N,N',N'-tris(9-phenylcarbazol-3-yl)benzol-1,3,5-triamin (Abkürzung: PCA3B), 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'-spirobi[9H-fluoren]-2-amine (abbreviation: PCBASF), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-Bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-Naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), 3-[N-(4-Diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA1), 3,6-Bis[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA2), 3,6-Bis[N-(4-diphenylaminophenyl)-N-(1-naphthyl)amino]-9-phenylcarbazole (abbreviation: PCzTPN2), N-(9,9-Spirobi[9H-fluorene]-2-yl)-N,9-diphenylcarbazole-3-amine (abbreviation: PCASF), N-[4-(9H-Carbazol-9-yl)phenyl]-N-(4-phenyl)phenylaniline (abbreviation: YGA1BP), N,N'-Bis[4-(carbazol-9-yl)phenyl]-N,N'-diphenyl-9,9-dimethylfluorene-2,7-diamine (abbreviation: YGA2F) and 4,4',4''-Tris(carbazol-9-yl)triphenylamine (abbreviation: TCTA).,

[0183] Other examples of the carbazole derivative include 9-[4-(9-Phenyl-9H-carbazol-3-yl)phenyl]phenanthrene (abbreviation: PCPPn), 3-[4-(1-Naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 1,3-Bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-Di(N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-Bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviation: CzTP), 1,3,5-Tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB) and 9-[4-(10-Phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA).

[0184] Specific examples of the furan derivative (an organic compound with a furan ring) include 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II) and 4-{ 3-[3-(9-Phenyl-9H-fluoren-9-yl)phenyl]phenyl} d dibenzofuran (abbreviation: mmDBFFLBi-II).

[0185] Specific examples of the thiophene derivative (an organic compound with a thiophene ring) include 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III) and 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV).

[0186] Specific examples of the aromatic amine include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminobiphenyl (abbreviation: TPD), N,N'-bis(9,9'-spirobi[9H-fluoren]-2-yl)-N,N'-diphenyl-4,4'-diaminobiphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), N-(9,9-Dimethyl-9H-fluoren-2-yl)-N-{9,9-dimethyl-2-[N'-phenyl-N'-(9,9-dimethyl-9H-fluoren-2-yl)amino]-9H-fluoren-7-yl}phenylamine (abbreviation: DFLADFL), N-(9,9-Dimethyl-2-diphenylamino-9H-fluoren-7-yl)diphenylamine (abbreviation: DPNF), N-(9,9-Spirobi[9H-fluoren]-2-yl)-N,N',N'-triphenyl-1,4-phenyldiamine (abbreviation: DPASF), N,N'-Diphenyl-N,N'-bis(4-diphenylaminophenyl)spirobi[9H-fluoren]-2,7-diamine (abbreviation: DPA2SF), 4,4',4''-Tris[N-(1-naphthyl)-N-phenylamino]triphenylamine (abbreviation: 1'-TNATA), 4,4',4''-Tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-Tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: m-MTDATA), N,N'-Di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'-Bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), DNTPD, 1,3,5-Tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), N-(4-Biphenyl)-6,N-diphenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BnfABP), N,N-Bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf), 4,4'-Bis(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)-4''-phenyltriphenylamine (abbreviation: BnfBB1BP), N,N-Bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-6-amine (abbreviation: BBABnf(6)), N,N-Bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf(8)), N,N-Bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviation: BBABnf(II)(4)), N,N-Bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP),N-[4-(Dibenzothiophen-4-yl)phenyl]-N-phenyl-4-biphenylamine (abbreviation: ThBA1BP), 4-(2-Naphthyl)-4',4''-diphenyltriphenylamine (abbreviation: BBAßNB), 4-[4-(2-Naphthyl)phenyl]-4',4''-diphenyltriphenylamine (abbreviation: BBAßNBi), 4,4'-Diphenyl-4''-([2,1'-binaphthyl]-6-yl)triphenylamine (abbreviation: BBAαNβNB), 4,4'-Diphenyl-4''-([2,1'-binaphthyl]-7-yl)triphenylamine (abbreviation: BBAαNβNB-03), 4,4'-Diphenyl-4''-(7-phenyl)naphthyl-2-yltriphenylamine (abbreviation: BBAPßNB-03), 4,4'-Diphenyl-4''-([2,2'-binaphthyl]-6-yl)triphenylamine (abbreviation: BBA(βN2)B), 4,4'-Diphenyl-4''-([2,2'-binaphthyl]-7-yl)triphenylamine (abbreviation: BBA(ßN2)B-03), 4,4'-Diphenyl-4''-([1,2'-binaphthyl]-4-yl)triphenylamine (abbreviation: BBAßNαNB), 4,4'-Diphenyl-4''-([1,2'-binaphthyl]-5-yl)triphenylamine (abbreviation: BBAßNαNB-02), 4-(4-Biphenylyl)-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: TPBiAßNB), 4-(3-Biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: mTPBiAβNBi),4-(4-Biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: TPBiAßNBi), 4-Phenyl-4'-(1-naphthyl)-triphenylamine (abbreviation: αNBA1BP), 4,4'-Bis(1-naphthyl)triphenylamine (abbreviation: αNBB1BP), 4,4'-Diphenyl-4''-[4'-(carbazol-9-yl)biphenyl-4-yl]triphenylamine (abbreviation: YGTBi1BP), 4'-[4-(3-Phenyl-9H-carbazol-9-yl)phenyl]tris(biphenyl-4-yl)amine (abbreviation: YGTBi1BP-02), 4-[4'-(Carbazol-9-yl)biphenyl-4-yl]-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: YGTBiβNB), N-[4-(9-Phenyl-9H-carbazol-3-yl)phenyl]-N-[4-(1-naphthyl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: PCBNBSF), N,N-Bis(biphenyl-4-yl)-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: BBASF), N,N-Bis(biphenyl-4-yl)-9,9'-spirobi[9H-fluorene]-4-amine (abbreviation: BBASF(4)), N-(Biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[9H-fluoren]-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'-[4-(9-phenylfluoren-9-yl)phenyl]triphenylamine (abbreviation: BPAFLBi), N,N-Bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-4-amine, N,N-Bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-3-amine, N,N-Bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-2-amine and N,N-Bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-1-amine.,

[0187] Other examples of hole transport materials include high-molecular-weight compounds (e.g., oligomers, dendrimers, and polymers), such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: poly-TPD). Alternatively, a high-molecular-weight compound to which an acid has been added can be used, such as poly(3,4-ethylenedioxythiophene) / polystyrenesulfonic acid (abbreviation: PEDOT / PSS) or polyaniline / polystyrenesulfonic acid (abbreviation: PAni / PSS).

[0188] It should be noted that the hole transport material is not limited to the above examples and any of the various known materials can be used alone or in combination as the hole transport material.

[0189] The hole injection layers (111, 111a and 111b) can be formed by any of the known film formation processes, such as a vacuum evaporation process. < Hole transport layer>

[0190] The hole transport layers (112, 112a, and 112b) transport the holes injected by the hole injection layers (111, 111a, and 111b) from the first electrode 101 to the light-emitting layers (113, 113a, and 113b). It should be noted that the hole transport layers (112, 112a, and 112b) each contain a hole transport material. Therefore, the hole transport layers (112, 112a, and 112b) can be formed using any of the hole transport materials that can be used for the hole injection layers (111, 111a, and 111b).

[0191] It should be noted that in the light-emitting device of an embodiment of the present invention, the organic compound used for the hole transport layers (112, 112a and 112b) can also be used for the light-emitting layers (113, 113a and 113b). The same organic compound is preferably used for both the hole transport layers (112, 112a and 112b) and the light-emitting layers (113, 113a and 113b), in which case holes can be efficiently transported from the hole transport layers (112, 112a and 112b) to the light-emitting layers (113, 113a and 113b). <Licht emittierende Schicht>

[0192] The light-emitting layers (113, 113a, and 113b) contain a light-emitting substance. It should be noted that a substance with an emission color of blue, violet, blue-violet, green, yellow-green, yellow, orange, red, or the like may be appropriately used as the light-emitting substance in the light-emitting layers (113, 113a, and 113b). If a variety of light-emitting layers are provided, the use of different light-emitting substances in the light-emitting layers allows for different emission colors (e.g., white light emission obtained by a combination of complementary emission colors). If a variety of light-emitting layers are provided, the light-emitting layers can all be the same color.A structure in which multiple light-emitting layers, all emitting light of the same color, are stacked on top of each other can, in some cases, achieve higher reliability than a single-layer structure. Furthermore, a multi-layer structure, in which a light-emitting layer contains two or more types of light-emitting substances, can be used.

[0193] The light-emitting layers (113, 113a and 113b) can each contain, in addition to a light-emitting substance (a guest material), one or more types of organic compounds (e.g. a host material).

[0194] In the case where a plurality of host materials are used in the light-emitting layers (113, 113a, and 113b), a second host material is preferably a substance exhibiting a larger energy gap than those of a known guest material and a first host material. Preferably, the lowest singlet excitation energy level (S1 level) of the second host material is higher than that of the first host material, and the lowest triplet excitation energy level (T1 level) of the second host material is higher than that of the guest material. With such a structure, an exciplex can be formed by the two types of host materials.To efficiently form an exciplex, a compound that readily accepts holes (a hole transport material) and a compound that readily accepts electrons (an electron transport material) are preferably combined. With the above structure, high efficiency, low voltage, and a long lifetime can be achieved simultaneously.

[0195] Organic compounds used as host materials (including the first and second host materials) include hole transport materials, which can be used for the hole transport layers (112, 112a, and 112b) described above, and electron transport materials, which can be used for the electron transport layers (114, 114a, and 114b) described below, provided they meet the requirements of the host material used in the light-emitting layer. Another example is an exciplex formed from two or more types of organic compounds (the first and second host materials).An exciplex whose excited state is formed by two or more types of organic compounds exhibits a very small difference between the S1 and T1 levels and serves as a thermally activated delayed fluorescence (TADF) material capable of converting triplet excitation energy to singlet excitation energy. In an example of a preferred combination of two or more types of organic compounds forming an exciplex, one compound of the two or more organic compounds has a π-electron-deficient heteroaromatic ring, and the other compound has a π-electron-rich heteroaromatic ring. A phosphorescent substance, such as an iridium-, rhodium-, or platinum-based organometallic complex or a metal complex, can be used as a component of the combination to form an exciplex.The organic compound represented by any of the general formulas (G1) to (G9), which has been described in embodiments 1 and 2, has a hole transport property and can therefore be used as a host material.

[0196] There is no particular restriction regarding the light-emitting substances that can be used for the light-emitting layers (113, 113a and 113b), and a light-emitting substance that converts the singlet excitation energy into light in the visible light range, or a light-emitting substance that converts the triplet excitation energy into light in the visible light range, can be used. <<Licht emittierende Substanz, die Singulett-Anregungsenergie in Licht umwandelt> >

[0197] Examples of light-emitting substances that convert singlet excitation energy into light emission and can be used in the light-emitting layers (113, 113a, and 113b) include the following substances that emit fluorescent light (fluorescent substances): a pyrene derivative, an anthracene derivative, a triphenylene derivative, a fluorene derivative, a carbazole derivative, a dibenzothiophene derivative, a dibenzofuran derivative, a dibenzoquinoxaline derivative, a quinoxaline derivative, a pyridine derivative, a pyrimidine derivative, a phenanthrene derivative, and a naphthalene derivative. A pyrene derivative is particularly preferred because it has a high emission quantum yield.Specific examples of the pyrene derivative include 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'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-bis(dibenzofuran-2-yl)-N,N'-diphenylpyrene-1,6-diamine (abbreviation: 1,6FrAPrn), N,N'-bis(dibenzothiophene-2-yl)-N,N'-diphenylpyrene-1,6-diamine (abbreviation: 1,6ThAPrn), N,N'-(pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-6-amine] (abbreviation: 1,6BnfAPrn), N,N'-(pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-02) and N,N'-(pyrene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03).

[0198] Furthermore, it is possible, for example, to form 5,6-Bis[4-(10-phenyl-9-anthryl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-Bis[4'-(10-phenyl-9-anthryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), N,N'-Bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-Diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), 4-(10-Phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), 4-[4-(10-Phenyl-9-anthryl)phenyl]-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPBA), Perylene, 2,5,8,11-Tetra-tert-butylperylene (abbreviation: TBP), 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,to use 10-diphenyl-2-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: 2PCAPPA) and N-[4-(9, 10-Diphenyl-2-anthryl)phenyl]-N, N, N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA).

[0199] It is also possible, for example, to use N-[9,10-Bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N-(9,10-Diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-Bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), 9,10-Bis(biphenyl-2-yl)-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracene-2-amine (abbreviation: 2YGABPhA), N,N,9-Triphenylanthracene-9-amine (abbreviation: DPhAPhA), Coumarin 545T, N,N'-Diphenylquinacridone (abbreviation: DPQd), Rubren, 5,12-Bis(biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BPT), 2-(2-{2-[4-(Dimethylamino)phenyl]ethenyl}-6-methyl-4H-pyran-4-ylidene)propanedinitrile (abbreviation: DCM1), 2-{2-Methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-α]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), 2-{2-Isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTI), 2-{2-tert-Butyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTB), 2-(2,6-Bis{2-[4-(dimethylamino)phenyl]ethenyl}-4H-pyran-4-ylidene)propanedinitrile (abbreviation: BisDCM), 2-{2,6-Bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: BisDCJTM), 1,6BnfAPrn-03, N,N'-Diphenyl-N,N'-bis(9-phenyl-9H-carbazol-2-yl)naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviation: 3,10PCA2Nbf(IV)-02) or 3,10-Bis[N-(dibenzofuran-3-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10FrA2Nbf(IV)-02). In particular, for example, a pyrenediamine compound such as 1,6FLPAPrn, 1,6mMemFLPAPrn or 1.6BnfAPrn-03 can be used. <<Licht emittierende Substanz, die Triplett-Anregungsenergie in eine Lichtemission umwandelt> >

[0200] Examples of light-emitting substances that convert triplet excitation energy into light and can be used in the light-emitting layer 113 include substances that emit phosphorescent light (phosphorescent substances) and TADF materials that exhibit thermally activated delayed fluorescence.

[0201] A phosphorescent substance is a compound that emits phosphorescence light but does not emit fluorescence light at temperatures higher than or equal to a low temperature (e.g., 77 K) and lower than or equal to room temperature (i.e., higher than or equal to 77 K and lower than or equal to 313 K). The phosphorescent substance preferably contains a metal element with a high spin-orbit interaction and may, for example, be an organometallic complex, a metal complex (platinum complex), or a rare-earth metal complex. In particular, the phosphorescent substance preferably contains a transition metal element.It is preferred that the phosphorescent substance contains a platinum group element (ruthenium (Ru), rhodium (Rh), palladium (Pd), osmium (Os), iridium (Ir) or platinum (Pt)), in particular iridium, in which case the probability of the direct transition between the singlet ground state and the triplet excitation state can be increased. <<Phosphoreszierende Substanz (von 450 nm bis 570 nm: Blau oder Grün)> >

[0202] Examples of phosphorescent substances that emit blue or green light and whose emission spectrum has a peak wavelength greater than or equal to 450 nm and less than or equal to 570 nm include the following substances.

[0203] Examples of the phosphorescent substance include organometallic complexes with a 4H-triazole ring, such as Tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN 2 ]phenyl-κC}iridium(III) (abbreviation: [Ir(mpptz-dmp)3]), Tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Mptz)3]), Tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPrptz-3b)3]) and Tris[3-(5-biphenyl)-5-isopropyl-4-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPr5btz)3]); organometallic complexes with a 1H-triazole ring, such as... B. Tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(Mptz1-mp)3]) and Tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Prptz1-Me)3]); organometallic complexes with an imidazole ring, such asfac-Tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpmi)3]) and Tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmpimpt-Me)3]; and organometallic complexes in which a phenylpyridine derivative with an electron-withdrawing group is a ligand, such as Bis[2-(4',6'-difluorophenyl)pyridinato-N,C. 2' ]iridium(III)tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), Bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2' ]iridium(III)picolinate (abbreviation: Flrpic), Bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N,C 2' }iridium(III)picolinate (abbreviation: [Ir(CF3ppy)2(pic)]) and Bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2' ]iridium(III)acetylacetonate (abbreviation: FIr(acac)). <<Phosphoreszierende Substanz (von 495 nm bis 590 nm: Grün oder Gelb)> >

[0204] Examples of phosphorescent substances that emit green or yellow light and whose emission spectrum has a peak wavelength greater than or equal to 495 nm and less than or equal to 590 nm include the following substances.

[0205] Examples of the phosphorescent substance include organometallic iridium complexes with a pyrimidine ring, such as... B. 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-t{ert-butyl-4-phenylpyrimidinato]iridium (III) (abbreviation: [Ir(tBuppm)2(acac)]), (Acetylacetonato)bis[6-(2-norbornyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]), (Acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenylpyrimidinato]iridium(III) (Abbreviation: [Ir(mpmppm)2(acac)]), (Acetylacetonato)bis{4,6-dimethyl-2-[6-(2,6-dimethylphenyl)-4-pyrimidinyl-κN 3 ]phenyl-κC}iridium(III) (abbreviation: [Ir(dmppm-dmp)2(acac)]) and (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)2(acac)]); organometallic iridium complexes with a pyrazine ring, such as (acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-Me)2(acac)]) and (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]); organometallic iridium complexes with a pyridine ring, such as B. Tris(2-phenylpyridinato-N,C 2' )iridium(III) (abbreviation: [Ir(ppy)3]), Bis(2-phenylpyridinato-N,C 2' )iridium(III)acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), Bis(benzo[h]quinolinato)iridium(III)acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), Tris(benzo[h]quinolinato)iridium(III) (abbreviation: [Ir(bzq)3]), Tris(2-phenylquinolinato-N,C 2' )iridium(III) (abbreviation: [Ir(pq)3]), Bis(2-phenylquinolinato-N,C 2' ), Bis[2-(2-pyridinyl-κN)phenyl-κC][2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC], [2-d3-methyl-8-(2-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridinyl-κN 2 )phenyl-κC]iridium(III) (Abbreviation: Ir(5mppy-d3)2(mbfpypy-d3)), {2-(Methyl-d3)-8-[4-(1-methylethyl-1-d)-2-pyridinyl-κN]benzofuro[2,3-b]pyridin-7-yl-κC}bis{5-(methyl-d3)-2-[5-(methyl-d3)-2-pyridinyl-κN]phenyl-κC}iridium(III) (Abbreviation: Ir(5mtpy-d6)2(mbfpypy-iPr-d4)), [2-d3-methyl-(2-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (Abbreviation: Ir(ppy)2(mbfpypy-d3)) and [2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(ppy)2(mdppy)); organometallic complexes, such as bis(2,4-diphenyl-1,3-oxazolato-N, C 2' )iridium(III)acetylacetonate (abbreviation: [Ir(dpo)2(acac)]), Bis{2-[4'-(perfluorophenyl)phenyl]pyridinato-N,C 2' }iridium(III)acetylacetonate (abbreviation: [Ir(p-PF-ph)2(acac)]) and bis(2-phenylbenzothiazolato-N,C 2' )iridium(III)acetylacetonate (abbreviation: [Ir(bt)2(acac)]); and a rare earth metal complex, such as Tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [Tb(acac)3(Phen)]). <<Phosphoreszierende Substanz (von 570 nm bis 750 nm: Gelb oder Rot)> >

[0206] Examples of phosphorescent substances that emit yellow or red light and whose emission spectrum has a peak wavelength greater than or equal to 570 nm and less than or equal to 750 nm include the following substances.

[0207] Examples of the phosphorescent substance include organometallic complexes with a pyrimidine ring, 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 (dipivaloylmethanato)bis[4,6-di(naphthalen-1-yl)pyrimidinato]iridium(III) (abbreviation: [Ir(d1npm)2(dpm)]); organometallic complexes with a pyrazine ring, such as... B. (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)]), Bis{4,6-dimethyl-2-[3-(3,5-dimethylphenyl)-5-phenyl-2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl-3,5-heptanedionato-κ 2 O,O')iridium(III) (abbreviation: [Ir(dmdppr-P)2(dibm)]), Bis{4,6-dimethyl-2-[5-(4-cyano-2,6-dimethylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,2,6, 6-tetramethyl-3,5-heptanedionato-κ 2 O,O')iridium(III) (abbreviation: [Ir(dmdppr-dmCP)2(dpm)]), Bis{2-[5-(2,6-dimethylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN]-4,6-dimethylphenyl-κC}(2,2',6,6'-tetramethyl-3,5-heptanedionato-κ 2 O,O')iridium(III) (abbreviation: [Ir(dmdppr-dmp)2(dpm)]), (Acetylacetonato)bis[2-methyl-3-phenylquinoxalinato-N,C 2' ]Iridium(III) (abbreviation: [Ir(mpq)2(acac)]), (Acetylacetonato)bis(2,3-diphenylquinoxalinato-N,C 2' )iridium(III) (abbreviation: [Ir(dpq)2(acac)]) and (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq)2(acac)]); organometallic complexes with a pyridine ring, such as 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)]) and bis[4,6-dimethyl-2-(2-quinolinyl-κN)phenyl-κC](2,4-pentanedionato-κ 2 O,O')iridium(III) (abbreviation: [Ir(dmpqn)2(acac)]); a platinum complex, such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrinplatin(II) (abbreviation: [PtOEP]); and rare earth metal complexes, such as Tris(1,3-diphenyl-1,3-propanediumoate)(monophenanthroline)europium(III) (abbreviation: [Eu(DBM)3(Phen)]) and Tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: [Eu(TTA)3(Phen)]). < <tadf-material>>

[0208] Any of the materials described below can be used as the TADF material. The TADF material is a material that exhibits a small difference between its S1 level and its T1 level (preferably less than or equal to 0.20 eV), allows upconversion of a triplet excitation state to a singlet excitation state (i.e., reverse intersystem crossing) using low thermal energy, and efficiently emits light (fluorescence) from the singlet excitation state. Thermally activated delayed fluorescence is efficiently obtained under the condition that the energy difference between the triplet excitation energy level and the singlet excitation energy level is greater than or equal to 0.00 eV and less than or equal to 0.20 eV, preferably greater than or equal to 0.00 eV and less than or equal to 0.10 eV.Delayed fluorescent light from the TADF material refers to light emission that has a spectrum similar to that of normal fluorescent light and a very long lifetime. The lifetime is longer than or equal to 1 × 10⁻⁶. -6 seconds or longer than or equal to 1 × 10 -3 Seconds.

[0209] It should be noted that the TADF material can also be used as an electron transport material, hole transport material, or host material.

[0210] Examples of TADF material include fullerene, a derivative thereof, an acridine derivative such as proflavin, and eosin. Other examples include a metal-containing porphyrin, such as a porphyrin containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd). Examples of metal-containing porphyrins include a protoporphyrin tin fluoride complex (abbreviation: SnF2(Proto IX)), a mesoporphyrin tin fluoride complex (abbreviation: SnF2(Meso IX)), a hematoporphyrin tin fluoride complex (abbreviation: SnF2(Hämato IX)), a coproporphyrin tetramethyl ester tin fluoride complex (abbreviation: SnF2(Copro III-4Me)), an octaethylporphyrin tin fluoride complex (abbreviation: SnF2(OEP)), an etioporphyrin tin fluoride complex (abbreviation: SnF2(Etio I)) and an octaethylporphyrin platinum chloride complex (abbreviation: PtCl2OEP).

[0211] Furthermore, a heteroaromatic compound can comprise a π-electron-rich heteroaromatic compound and a π-electron-poor heteroaromatic compound, such as:2-(Biphenyl-4-yl)-4,6-bis(12-phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 2-[4-(10H-phenoxazin-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4-(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-Dimethyl-9H-acridin-10-yl)-9H-xanthen-9-one (abbreviation: ACRXTN), Bis[4-(9,9-dimethyl-9,10-dihydroacridin)phenyl]sulfone (abbreviation: DMAC-DPS), 10-Phenyl-1OH,10'H-spiro[acridin-9,9'-anthracene]-10'-one (abbreviation: ACRSA), 4-(9'-Phenyl-[3,3'-bi-9H-carbazole]-9-yl)benzofuro[3,2-d]pyrimidine (abbreviation: 4PCCzBfpm), 4-[4-(9'-Phenyl-[3,3'-bi-9H-carbazole]-9-yl)phenyl]benzofuro[3,2-d]pyrimidine (abbreviation: 4PCCzPBfpm) or 9-[3-(4,6-Diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn-02).

[0212] It should be noted that a substance in which a π-electron-rich heteroaromatic compound is directly bonded to a π-electron-poor heteroaromatic compound is particularly preferred, since both the donor property of the π-electron-rich heteroaromatic compound and the acceptor property of the π-electron-poor heteroaromatic compound are enhanced, and the energy difference between the singlet and triplet excitation states becomes small. A TADF material in which the singlet and triplet excitation states are in thermal equilibrium (TADF100) can be used. Since such a TADF material enables a short emission lifetime (excitation lifetime), the efficiency of a light-emitting device is less likely to be reduced in a high luminance range.

[0213] In addition to the above, another example of a material with a function for converting triplet excitation energy into light emission is a nanostructure of a transition metal compound with a perovskite structure. In particular, a nanostructure of a metal halide perovskite material is preferred. The nanostructure is preferably a nanoparticle or a nanorod.

[0214] The organic compound (e.g., the host material) used in combination with the light-emitting substance (the guest material) described above in the light-emitting layers (113, 113a and 113b) can be one or more types selected from substances with a larger energy gap than the light-emitting substance (the guest material). <<Wirtsmaterial für Fluoreszenz> >

[0215] In the case where the light-emitting substance used in the light-emitting layers (113, 113a, and 113b) is a fluorescent substance, an organic compound (a host material) used in combination with the fluorescent substance is preferably an organic compound that has a high energy level in a singlet excitation state and a low energy level in a triplet excitation state, or an organic compound with a high fluorescence quantum yield. Therefore, for example, the hole transport material (described above) and the electron transport material (described below) shown in this embodiment can be used, provided they are organic compounds that meet such a condition. Furthermore, the organic compounds described in embodiments 1 and 2 can be used.

[0216] With regard to a preferred combination with the light-emitting substance (the fluorescent substance), examples of the organic compound (the host material), some of which overlap with the specific examples above, include condensed polycyclic aromatic compounds, such as an anthracene derivative, a tetracene derivative, a phenanthrene derivative, a pyrene derivative, a chrysene derivative, and a dibenzo[g,p]chrysene derivative.

[0217] Specific examples of the organic compound (host material) preferably used in combination with the fluorescent substance include 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 3-[4-(1-naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 9,10-diphenylanthracene (abbreviation: DPAnth), N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), YGAPA, PCAPA, N,9-Diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazol-3-amine (abbreviation: PCAPBA), N-(9,10-Diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), 6,12-Dimethoxy-5,11-diphenylchrysene, N,N,N',N',N',N'',N'',N''',N'''-Octaphenyldibenzo[g,p]chrysene-2,7,10,15-tetraamine (abbreviation: DBC1), 9-[4-(10-Phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA),7-[4-(10-Phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 6-[3-(9,10-Diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-Phenyl-10-[4'-(9-phenyl-9H-fluoren-9-yl)biphenyl-4-yl]anthracene (abbreviation: FLPPA), 9,10-Bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-Di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-Butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9-(1-Naphthyl)-10-(2-naphthyl)anthracene (abbreviation: α,β-ADN), 2-(10-Phenylanthracene-9-yl)dibenzofuran, 2-(10-Phenyl-9-anthryl)-benzo[b]naphtho[2,3-d]furan (abbreviation: Bnf(II)PhA), 9-(1-Naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth), 2,9-Di(1-naphthyl)-10-phenylanthracene (abbreviation: 2αN-αNPhA), 9-(1-Naphthyl)-10-[3-(1-naphthyl)phenyl]anthracene (abbreviation: αNmαNPAnth), 9-(2-Naphthyl)-10-[3-(1-naphthyl)phenyl]anthracene (abbreviation: βNmαNPAnth), 9-(1-Naphthyl)-10-[4-(1-naphthyl)phenyl]anthracene (abbreviation: αN-αNPAnth),9-(2-Naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: βN-βNPAnth), 2-(1-Naphthyl)-9-(2-naphthyl)-10-phenylanthracene (abbreviation: 2αN-βNPhA), 9-(2-Naphthyl)-10-[3-(2-naphthyl)phenyl]anthracene (abbreviation: βN-mβNPAnth), 1-{4-[10-(Biphenyl-4-yl)-9-anthryl]phenyl}-2-ethyl-1H-benzimidazole (abbreviation: EtBImPBPhA), 9,9'-Bianthryl (abbreviation: BANT), 9,9'-(Stilben-3,3'-diyl)diphenanthrene (abbreviation: DPNS) 9,9'-(Stilben-4,4'-diyl)diphenanthrene (abbreviation: DPNS2), 1,3,5-Tri(1-pyrenyl)benzene (abbreviation: TPB3), 5,12-Diphenyltetracene and 5,12-Bis(biphenyl-2-yl)tetracene. <<Wirtsmaterial für Phosphoreszenz> >

[0218] In the case where the light-emitting substance used in the light-emitting layers (113, 113a and 113b) is a phosphorescent substance, an organic compound with a triplet excitation energy (an energy difference between a ground state and a triplet excitation state) higher than that of the light-emitting substance is preferably selected as the organic compound (host material) used in combination with the phosphorescent substance. It should be noted that when a plurality of organic compounds (e.g., a first host material and a second host material (or an auxiliary material)) are used to form an exciplex in combination with a light-emitting substance, the plurality of organic compounds are preferably mixed with the phosphorescent substance.Furthermore, the organic compounds described in embodiments 1 and 2 can be used.

[0219] With such a structure, light emission can be efficiently achieved through exciplex triplet energy transfer (ExTET), which is the transfer of energy from an exciplex to a light-emitting substance. It should be noted that a combination of the many organic compounds that readily form an exciplex is preferred, and it is particularly advantageous to combine a compound that readily accepts holes (hole transport material) with a compound that readily accepts electrons (electron transport material).

[0220] With regard to a preferred combination with the light-emitting substance (phosphorescent substance), examples of the organic compounds (the host material and the auxiliary material), some of which are mentioned in the specific examples above, include an aromatic amine (an organic compound with an aromatic amine skeleton), a carbazole derivative (an organic compound with a carbazole ring), a dibenzothiophene derivative (an organic compound with a dibenzothiophene ring), a dibenzofuran derivative (an organic compound with a dibenzofuran ring), an oxadiazole derivative (an organic compound with an oxadiazole ring), a triazole derivative (an organic compound with a triazole ring), a benzimidazole derivative (an organic compound with a benzimidazole ring), and a quinoxaline derivative (an organic compound with a quinoxaline ring).a dibenzoquinoxaline derivative (an organic compound with a dibenzoquinoxaline ring), a pyrimidine derivative (an organic compound with a pyrimidine ring), a triazine derivative (an organic compound with a triazine ring), a pyridine derivative (an organic compound with a pyridine ring), a bipyridine derivative (an organic compound with a bipyridine ring), a phenanthroline derivative (an organic compound with a phenanthroline ring), a furodiazine derivative (an organic compound with a furodiazine ring), and zinc- or aluminum-based metal complexes.

[0221] Specific examples of the aromatic amine and the carbazole derivative, which are organic compounds with high hole transport properties among the organic compounds described above, are the same as the specific examples of the hole transport materials described above, and these materials are preferred as host material.

[0222] Specific examples of the dibenzothiophene derivative and the dibenzofuran derivative, which are organic compounds with high hole transport properties among the organic compounds described above, include 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II), 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II), DBT3P-II, 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV) and 4-[3-(Triphenylen-2-yl)phenyl]dibenzothiophene (abbreviation: mDBTPTp-II). Such derivatives are preferred as host material.

[0223] Other examples of preferred host materials include metal complexes with an oxazole-based ligand or a thiazole-based ligand, such as bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO) and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ).

[0224] Among the aforementioned organic compounds, specific examples include the oxadiazole derivative, the triazole derivative, the benzimidazole derivative, the quinoxaline derivative, the dibenzoquinoxaline derivative, the quinazoline derivative, and the phenanthroline derivative, which are organic compounds with high electron transport properties; an organic compound comprising a heteroaromatic ring with a polyazole ring, such as...2-(4-Biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-Bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-Phenyl-1,3,4-oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviation: CO11), 3-(4-Biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 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) or 4,4'-Bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs); an organic compound comprising a heteroaromatic ring with a phenanthroline ring, such as bathophenanthroline (abbreviation: Bphen), bathocuproine (abbreviation: BCP), 2,9-Di(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen) or 2,2'-(1,3-phenylene)bis(9-phenyl-1,10-phenanthroline) (abbreviation: mPPhen2P); and an organic compound comprising a heteroaromatic ring with a dibenzoquinoxaline ring, such as2-[3-(Dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(Dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-Carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 2-[4-(3,6-Diphenyl-9H-carbazol-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(Dibenzothiophen-4-yl)phenyl]dibenzo[fh]quinoxaline (abbreviation: 7mDBTPDBq-II) 6-[3-(Dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II), 2-{4-[9,10-Di(2-naphthyl)-2-anthryl]phenyl}-1-phenyl-1H-benzimidazole (abbreviation: ZADN) or 2-[4'-(9-Phenyl-9H-carbazol-3-yl)-3,1'-biphenyl-1-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mpPCBPDBq). These organic compounds are preferred as host material.

[0225] Among the aforementioned organic compounds, specific examples include the pyridine derivative, the diazine derivative (e.g., the pyrimidine derivative, the pyrazine derivative, and the pyridazine derivative), the triazine derivative, and the furodiazine derivative, which are organic compounds with high electron transport properties; organic compounds comprising a heteroaromatic ring with a diazine ring, such as... B. 4,6-Bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-Bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6-Bis[3-(9H-carbazol-9-yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), 2-{4-[3-(N-Phenyl-9H-carbazol-3-yl)-9H-carbazol-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), 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-Tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), 9,9'-[Pyrimidin-4,6-diylbis(biphenyl-3,3'-diyl)]bis(9H-carbazol) (Abkürzung: 4,6mCzBP2Pm), 2-[3'-(9,9-Dimethyl-9H-fluoren-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazin (Abkürzung: mFBPTzn), 8-(Biphenyl-4-yl)-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidin (Abkürzung: 8BP-4mDBtPBfpm), 9-[3'-(Dibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazin (Abkürzung: 9mDBtBPNfpr), 9-[3'-(Dibenzothiophen-4-yl)biphenyl-4-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazin (Abkürzung: 9pmDBtBPNfpr), 11-[3'-(Dibenzothiophen-4-yl)biphenyl-3-yl]phenanthro[9',10':4,5]furo[2,3-b]pyrazin (Abkürzung: 11mDBtBPPnfpr), 11-[3'-(Dibenzothiophen-4-yl)biphenyl-4-yl]phenanthro[9',10':4,5]furo[2,3-b]pyrazin, 11-[(3'-(9H-Carbazol-9-yl)biphenyl-3-yl]phenanthro[9',10':4,5]furo[2,3-h]pyrazin, 12-(9'-Phenyl-[3,3'-bi-9H-carbazol]-9-yl)phenanthro[9',10':4,5]furo[2,3-b]pyrazin (Abkürzung: 12PCCzPnfpr), 9-[3'-(9-Phenyl-9H-carbazol-3-yl)biphenyl-4-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazin (Abkürzung: 9pmPCBPNfpr), 9-(9'-Phenyl-[3,3'-bi-9H-carbazol]-9-yl)naphtho[1',2':4,5]furo[2,3-b]pyrazin (Abkürzung: 9PCCzNfpr), 10-(9'-Phenyl-[3,3'-bi-9H-carbazol]-9-yl)naphtho[1',2':4,5]furo[2,3-b]pyrazin (Abkürzung: 10PCCzNfpr), 9-[3'-(6-Phenylbenzo[b]naphtho[1,2-d]furan-8-yl)biphenyl-3-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazin (Abkürzung: 9mBnfBPNfpr), 9-{3-[6-(9,9-Dimethylfluoren-2-yl)dibenzothiophen-4-yl]phenyl}naphtho[1',2':4,5]furo[2,3-b]pyrazin (Abkürzung: 9mFDBtPNfpr), 9-[3'-(6-Phenyldibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazin (Abkürzung: 9mDBtBPNfpr-02), 9-[3-(9'-Phenyl-[3,3'-bi-9H-carbazol]-9-yl)phenyl]naphtho[1',2':4,5]furo[2,3-b]pyrazin (Abkürzung: 9mPCCzPNfpr), 9-[3'-(2,8-Diphenyldibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazin, 11-[3'-(2,8-Diphenyldibenzothiophen-4-yl)biphenyl-3-yl]phenanthro[9',10':4,5]furo[2,3-b]pyrazin, 5-[3-(4,6-Diphenyl-1,3,5-triazin-2-yl)phenyl]-7,7-dimethyl-5H,7H-indeno[2,1-b]carbazole (abbreviation: mlNc(II)PTzn), 2-[3'-(Triphenylen-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mTpBPTzn), 2-(Biphenyl-4-yl)-4-phenyl-6-(9,9'-spirobi[9H-fluorene]-2-yl)-1,3,5-triazine (abbreviation: BP-SFTzn), 2,6-Bis(4-naphthalen-1-ylphenyl)-4-[4-(3-pyridyl)phenyl]pyrimidine (abbreviation: 2,4NP-6PyPPm), 3-[9-(4,6-Diphenyl-1,3,5-triazine-2-yl)-2-dibenzofuranyl]-9-phenyl-9H-carbazole (abbreviation: PCDBfTzn), 2-(Biphenyl-3-yl)-4-phenyl-6-[8-([1,1':4',1''-terphenyl]-4-yl)-1-dibenzofuranyl]-1,3,5-triazine (abbreviation: mBP-TPDBfTzn), 6-(Biphenyl-3-yl)-4-[3,5-bis(9H-carbazol-9-yl)phenyl)-2-phenylpyrimidine (abbreviation: 6mBP-4Cz2PPm) and 4-[3,5-Bis(9H-carbazol-9-yl)phenyl]-2-phenyl-6-(biphenyl-4-yl)pyrimidine (abbreviation: 6BP-4Cz2PPm), and these materials are preferred as host material.

[0226] Among the aforementioned organic compounds, specific examples of metal complexes exhibiting high electron transport properties include zinc- or aluminum-based metal complexes, such as tris(8-quinolinolato)aluminium(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminium(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinolato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminium(III) (abbreviation: BAlq), and bis(8-quinolinolato)zinc(II) (abbreviation: Znq), and metal complexes with a quinoline ring or a benzoquinoline ring. These metal complexes are preferred as host materials.

[0227] Furthermore, high molecular weight compounds, such as poly(2,5-pyridindiyl) (abbreviation: PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy), are preferred as host material.

[0228] Furthermore, the following organic compounds with a diazine ring, exhibiting bipolarity, high hole transport, and high electron transport properties, can be used as host material: 9-Phenyl-9'-(4-phenyl-2-quinazolinyl)-3,3'-bi-9H-carbazole (abbreviation: PCCzQz), 2-[4'-(9-Phenyl-9H-carbazol-3-yl)-3,1'-biphenyl-1-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mpPCBPDBq), 5-[3-(4,6-Diphenyl-1,3,5-triazin-2-yl)phenyl]-7,7-dimethyl-5H,7H-indeno[2,1-b]carbazole (abbreviation: mlNc(II)PTzn), 11-[4-(Biphenyl-4-yl)-6-phenyl-1,3,5-triazin-2-yl]-11,12-dihydro-12-phenyl-indolo[2,3-a]carbazole (abbreviation: BP-Icz(II)Tzn) and 7-[4-(9-Phenyl-9H-carbazol-2-yl)quinazolin-2-yl]-7H-dibenzo[c,g]carbazole (abbreviation: PC-cgDBCzQz). <elektronentransportschicht>

[0229] The electron transport layers (114, 114a and 114b) transport electrons injected by the electron injection layers (115, 115a and 115b) described below from the second electrode 102 and the charge generation layers (106, 106a and 106b) to the light-emitting layers (113, 113a and 113b). The heat resistance of the light-emitting device of an embodiment of the present invention can be improved by including the stacked electron transport layers. The electron transport material used in the electron transport layers (114, 114a and 114b) is preferably a substance with an electron mobility of 1 × 10⁻⁶ or higher. -6 cm 2 / Vs in the case where the square root of the electric field strength [V / cm] is 600. It should be noted that any other substance can also be used, as long as the substance has an electron transport property that is higher than its hole transport property. The electron transport layers (114, 114a, and 114b) can function even with a single-layer structure and can have a multi-layer structure comprising two or more layers. If a photolithography process is carried out over the electron transport layer, which contains the above-described mixed material that has heat resistance, any adverse effect of the thermal process on the device properties can be reduced. < <elektronentransportmaterial>>

[0230] An organic compound with high electron transport properties can be used as the electron transport material for the electron transport layers (114, 114a, and 114b), and for example, a heteroaromatic compound can be used. The term heteroaromatic compound refers to a cyclic compound containing at least two different types of elements in a ring. Examples of cyclic structures include a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, and the like, among which a five-membered ring and a six-membered ring are particularly preferred. The elements contained in the heteroaromatic compound are preferably, in addition to carbon, one or more of nitrogen, oxygen, sulfur, and the like.A heteroaromatic compound containing nitrogen (a nitrogenous heteroaromatic compound) is particularly preferred, and any of the materials with high electron transport properties (electron transport materials), such as a nitrogenous heteroaromatic compound and a π-electron-deficient heteroaromatic compound comprising the nitrogenous heteroaromatic compound, is preferably used.

[0231] It should be noted that the electron transport material can differ from the materials used in the light-emitting layer. Not all excitons generated by charge carrier recombination in the light-emitting layer can contribute to light emission, and some excitons diffuse into a layer in contact with or near the light-emitting layer. To avoid this phenomenon, the energy level (the lowest singlet excitation level or the lowest triplet excitation level) of a material used for the layer in contact with or near the light-emitting layer is preferably higher than that of a material used for the light-emitting layer itself.Therefore, if a material different from the material of the light-emitting layer is used as the electron transport material, a highly efficient device can be obtained.

[0232] A heteroaromatic compound is an organic compound that includes at least one heteroaromatic ring.

[0233] The heteroaromatic ring comprises any one of a pyridine ring, a diazine ring, a triazine ring, a polyazole ring, an oxazole ring, a thiazole ring, and the like. A heteroaromatic ring with a diazine ring comprises a heteroaromatic ring with a pyrimidine ring, a pyrazine ring, a pyridazine ring, or the like. A heteroaromatic ring with a polyazole ring comprises a heteroaromatic ring with an imidazole ring, a triazole ring, or an oxadiazole ring.

[0234] A heteroaromatic ring comprises a condensed heteroaromatic ring with a condensed ring structure. Examples of condensed heteroaromatic rings include a quinoline ring, a benzoquinoline ring, a quinoxaline ring, a dibenzoquinoxaline ring, a quinazoline ring, a benzoquinazoline ring, a dibenzoquinazoline ring, a phenanthroline ring, a furodiazine ring, and a benzimidazole ring.

[0235] Examples of heteroaromatic compounds with a five-membered ring structure, which are heteroaromatic compounds containing carbon and one or more of nitrogen, oxygen, sulfur, and the like, include a heteroaromatic compound with an imidazole ring, a heteroaromatic compound with a triazole ring, a heteroaromatic compound with an oxazole ring, a heteroaromatic compound with an oxadiazole ring, a heteroaromatic compound with a thiazole ring, and a heteroaromatic compound with a benzimidazole ring.

[0236] Examples of heteroaromatic compounds with a six-membered ring structure, which are heteroaromatic compounds containing carbon and one or more elements of nitrogen, oxygen, sulfur, and the like, include heteroaromatic compounds with a heteroaromatic ring such as a pyridine ring, a diazine ring (a pyrimidine ring, a pyrazine ring, a pyridazine ring, or the like), a triazine ring, or a polyazole ring. Further examples include heteroaromatic compounds with a bipyridine structure, heteroaromatic compounds with a terpyridine structure, and the like, which are included in examples of heteroaromatic compounds in which pyridine rings are linked.

[0237] Examples of the heteroaromatic compound with a condensed ring structure, which partially comprises the aforementioned six-membered ring structure, include a heteroaromatic compound with a condensed heteroaromatic ring such as a quinoline ring, a benzoquinoline ring, a quinoxaline ring, a dibenzoquinoxaline ring, a phenanthroline ring, a furodiazine ring (including a structure in which an aromatic ring is condensed with a furan ring of a furodiazine ring), or a benzimidazole ring.

[0238] Specific examples of the heteroaromatic compound described above, with a five-membered ring structure (a polyazole ring (including an imidazole ring, a triazole ring, or an oxadiazole ring), an oxazole ring, a thiazole ring, or a benzimidazole ring), include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviation: CO11), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-Butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), 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) and 4,4'-Bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs).

[0239] Specific examples of the heteroaromatic compound described above with a six-membered ring structure (including a heteroaromatic ring with a pyridine ring, a diazine ring, a triazine ring, or the like) include: a heteroaromatic compound comprising a heteroaromatic ring with a pyridine ring, such as 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy) or 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB); a heteroaromatic compound comprising a heteroaromatic ring with a triazine ring, such as... B. 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-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), 5-[3-(4,6-Diphenyl-1,3,5-triazin-2-yl)phenyl]-7,7-dimethyl-5H,7H-indeno[2,1-b]carbazole (abbreviation: mINc(II)PTzn), 2-[3'-(Triphenylen-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mTpBPTzn), 2-(Biphenyl-4-yl)-4-phenyl-6-(9,9'-spirobi[9H-fluorene]-2-yl)-1,3,5-triazine (abbreviation: BP-SFTzn), 2,6-Bis(4-naphthalen-1-ylphenyl)-4-[4-(3-pyridyl)phenyl]pyrimidine (abbreviation: 2,4NP-6PyPPm), 3-[9-(4,6-Diphenyl-1,3,5-triazine-2-yl)-2-dibenzofuranyl]-9-phenyl-9H-carbazole (abbreviation: PCDBfTzn), 2-(Biphenyl-3-yl)-4-phenyl-6-{8-[(1,1':4',1''-terphenyl)-4-yl]-1-dibenzofuranyl}-1,3,5-triazine (abbreviation: mBP-TPDBfTzn), 2-{3-[3-(Dibenzothiophen-4-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mDBtBPTzn) or mFBPTzn; and a heteroaromatic compound comprising a heteroaromatic ring with a diazine (pyrimidine) ring, such as... B. 4,6-Bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-Bis[3-(dibenzothiophen-4-yl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6-Bis[3-(9H-carbazol-9-yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), 4,6mCzBP2Pm, 6-(Biphenyl-3-yl)-4-[3,5-bis(9H-carbazol-9-yl)phenyl]-2-phenylpyrimidine (abbreviation: 6mBP-4Cz2PPm), 4-[3,5-Bis(9H-carbazol-9-yl)phenyl]-2-phenyl-6-(biphenyl-4-yl)pyrimidine (abbreviation: 6BP-4Cz2PPm), 4-[3-(Dibenzothiophen-4-yl)phenyl]-8-(naphthalen-2-yl)-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8βN-4mDBtPBfpm), 8BP-4mDBtPBfpm, 9mDBtBPNfpr, 9pmDBtBPNfpr, 3,8-Bis[3-(dibenzothiophen-4-yl)phenyl]benzofuro[2,3-b]pyrazine (abbreviation: 3,8mDBtP2Bfpr), 4,8-Bis[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 4,8mDBtP2Bfpm), 8-[3'-(Dibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]furo[3,2-d]pyrimidine (abbreviation: 8mDBtBPNfpm) or 8-([2,2'-Binaphthalene]-6-yl]-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8(βN2)-4mDBtPBfpm). It should be noted that the above aromatic compounds, which comprise a heteroaromatic ring, are heteroaromatic compounds with comprise a condensed heteroaromatic ring.

[0240] Other examples include heteroaromatic compounds comprising a heteroaromatic ring with a diazine (pyrimidine) ring, such as... B. 2,2'-(pyridine-2,6-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviation: 2,6(P-Bqn)2Py), 2,2'-([2,2'-bipyridine]-6,6'-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviation: 6,6'(P-Bqn)2BPy), 2,2'-(pyridine-2,6-diyl)bis{4-[4-(2-naphthyl)phenyl]-6-phenylpyrimidine} (abbreviation: 2,6(NP-PPm)2Py) or 6-(biphenyl-3-yl)-4-[3,5-bis(9H-carbazol-9-yl)phenyl]-2-phenylpyrimidine (abbreviation: 6mBP-4Cz2PPm), and a heteroaromatic compound, which includes a heteroaromatic ring with a triazine ring, such as 2,4,6-Tris[3'-(pyridin-3-yl)biphenyl-3-yl]-1,3,5-triazine (abbreviation: TmPPPyTz), 2,4,6-Tris(2-pyridyl)-1,3,5-triazine (abbreviation: 2Py3Tzn) or 2-[3-(2,6-Dimethyl-3-pyridinyl)-5-(9-phenanthryl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mPn-mDMePyPTzn).

[0241] Specific examples of the heteroaromatic compound with a condensed ring structure described above, which partially comprises a six-membered ring structure (the heteroaromatic compound with a condensed ring structure), include a heteroaromatic compound with a quinoxaline ring, such as:Bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), 2,9-Di(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen), 2,2'-(1,3-phenylene)bis(9-phenyl-1,10-phenanthroline) (abbreviation: mPPhen2P), 2,2'-(pyridine-2,6-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviation: 2,6(P-Bqn)2Py), 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (Abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-Carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 2-[4-(3,6-Diphenyl-9H-carbazol-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(Dibenzothiophen-4-yl)phenyl]dibenzo[fh]quinoxaline (abbreviation: 7mDBTPDBq-II), 6-[3-(Dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II) and 2mpPCBPDBq.

[0242] For the electron transport layers (114, 114a and 114b), in addition to the heteroaromatic compounds described above, any of the metal complexes listed below can be used. Examples of the metal complexes include a metal complex with a quinoline ring or a benzoquinoline ring, such as tris(8-quinolinolato)aluminium(III) (abbreviation: Alq3), Almq3, 8-quinolinolatolithium (abbreviation: Liq), BeBq2, bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminium(III) (abbreviation: BAlq) or bis(8-quinolinolato)zinc(II) (abbreviation: Znq), and a metal complex with an oxazole ring or a thiazole ring, such as... B. Bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO) or Bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ).

[0243] High molecular weight compounds, such as poly(2,5-pyridindiyl) (abbreviation: PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy), can be used as electron transport materials.

[0244] Each of the electron transport layers (114, 114a and 114b) is not limited to a single layer and can be a layer arrangement of two or more layers, each containing any one of the aforementioned substances. <elektroneninjektionsschicht>

[0245] The electron injection layers (115, 115a and 115b) contain a substance with high electron injection properties. These layers are designed to increase the efficiency of electron injection from the second electrode 102 and are preferably formed using a material whose LUMO level is only slightly different (less than or equal to 0.50 eV) from the work function of a material used for the second electrode 102. Therefore, the electron injection layer 115 can be formed using an alkali metal, an alkaline earth metal, or a compound thereof, such as... B. Lithium, cesium, lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), 8-quinolinolatolithium (abbreviation: Liq), 2-(2-pyridyl)phenolatolithium (abbreviation: LiPP), 2-(2-pyridyl)-3-pyridinolatolithium (abbreviation: LiPPy), 4-phenyl-2-(2-pyridyl)phenolatolithium (abbreviation: LiPPP), an oxide of lithium (LiO). x ) or cesium carbonate. A rare-earth metal or a rare-earth metal compound, such as erbium fluoride (ErF3) or ytterbium (Yb), can also be used. It is also possible to use a compound comprising a 1,3,4,6,7,8-tetrahydro-2H-pyrimido[1,2-a]pyrimidine framework, such as... B. 1-(9,9'-Spirobi[9H-fluoren]-2-yl)-1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (abbreviation: 2hppSF), 1,1'-(9,9'-Spirobi[9H-fluoren]-2,7-diyl)bis(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine) (abbreviation: 2,7hpp2SF) or 1,1'-Pyridine-2,6-diyl-bis(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine) (abbreviation: hpp2Py), to use. To form the electron injection layers (115, 115a and 115b), two or more of the above materials can be mixed or stacked. An electride can also be used for the electron injection layers (115, 115a and 115b).Examples of an electride include substances in which electrons are added to a calcium oxide-aluminum oxide at a high concentration. Any of the substances listed above can also be used to form the electron transport layers (114, 114a and 114b).

[0246] A mixed material containing an organic compound and an electron donor (donor) can also be used for the electron injection layers (115, 115a, and 115b). Such a mixed material is excellent in both electron injection and electron transport properties, since electrons are generated in the organic compound by the electron donor. Here, the organic compound is preferably a material that is excellent in transporting the generated electrons; in particular, for example, the electron transport materials described above that are used for the electron transport layers (114, 114a, and 114b), such as a metal complex and a heteroaromatic compound, can be used. Preferably, a substance is used that exhibits electron donor properties with respect to an organic compound.In particular, an alkali metal, an alkaline earth metal, and a rare earth metal are preferred, and lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like are specified. Furthermore, an alkali metal oxide and an alkaline earth metal oxide are preferred, and lithium oxide, calcium oxide, barium oxide, and the like are specified. Alternatively, a Lewis base, such as magnesium oxide, may be used. As a further alternative, an organic compound, such as tetrathiafulvalene (abbreviation: TTF), may be used. Alternatively, a layered arrangement of two or more of these materials may be used.

[0247] A mixed material containing an organic compound and a metal can also be used for the electron injection layers (115, 115a and 115b). The organic compound used here preferably has a LUMO level higher than or equal to -3.60 eV and lower than or equal to -2.30 eV. Furthermore, a material with an unshared electron pair is preferred.

[0248] Therefore, a mixed material obtained by mixing a metal and the heteroaromatic compound specified above as a material suitable for the electron transport layer can be used as the organic compound used in the aforementioned mixed material. Preferred examples of the heteroaromatic compound include materials with an unshared electron pair, such as a heteroaromatic compound with a five-membered ring structure (e.g., an imidazole ring, a triazole ring, an oxazole ring, an oxadiazole ring, a thiazole ring, or a benzimidazole ring), a heteroaromatic compound with a six-membered ring structure (e.g.,a pyridine ring, a diazine ring (including a pyrimidine ring, a pyrazine ring, a pyridazine ring, or the like), a triazine ring, a bipyridine ring, or a terpyridine ring), and a heteroaromatic compound with a fused ring structure partially comprising a six-membered ring structure (e.g., a quinoline ring, a benzoquinoline ring, a quinoxaline ring, a dibenzoquinoxaline ring, or a phenanthroline ring). Since the materials have been specifically described above, their description is omitted here.

[0249] The metal used for the aforementioned mixed material is preferably a transition metal belonging to Group 5, Group 7, Group 9 or Group 11 of the periodic table, or a material belonging to Group 13 of the periodic table; examples include Ag, Cu, Al and In. The organic compound forms a singly occupied molecular orbital (SOMO) with the transition metal.

[0250] To amplify light received from the light-emitting layer 113b, the optical path length between the second electrode 102 and the light-emitting layer 113b is preferably less than one-quarter of the wavelength λ of the light emitted by the light-emitting layer 113b. In this case, the optical path length can be adjusted by changing the thickness of the electron transport layer 114b or the electron injection layer 115b.

[0251] When the two EL layers (103a and 103b) are provided and the charge-generating layer 106 is located between the multitude of EL layers as in the light-emitting device in Fig. If 3E is provided, a structure can be obtained in which a multitude of EL layers are arranged on top of each other between the pair of electrodes (the structure is also called a tandem structure). <ladungserzeugungsschicht>

[0252] The charge-generating layer 106 has a function for injecting electrons into the organic compound layer 103a and for injecting holes into the organic compound layer 103b when a voltage is applied between the first electrode (anode) 101 and the second electrode (cathode) 102. The charge-generating layer 106 can be either a p-type layer, in which an electron acceptor is added to a hole transport material, or an electron injection buffer layer, in which an electron donor is added to an electron transport material. Alternatively, both of these structures can be stacked on top of each other. Furthermore, an electron conduction layer can be provided between the p-type layer and the electron injection buffer layer.It should be noted that forming the charge-generating layer 106 using any of the above materials can prevent an increase in operating voltage caused by the layer arrangement of the EL layers.

[0253] In the case where the charge-generating layer 106 is a p-type layer in which an electron acceptor is added to a hole-transporting material that is an organic compound, any of the materials described in this embodiment can be used as the hole-transporting material. Examples of the electron acceptor include 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ) and chloranil. Other examples include oxides of metals belonging to groups 4 to 8 of the periodic table. Specific examples include vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide. Any of the acceptor materials described above can be used. Furthermore, a mixed film obtained by mixing materials of a p-type layer or a layered arrangement of films containing the respective materials can be used.

[0254] In the case where the charge-generating layer 106 is an electron injection buffer layer in which an electron donor is added to an electron transport material, any of the materials described in this embodiment can be used as the electron transport material. An alkali metal, an alkaline earth metal, a rare earth metal, a metal belonging to Group 2 or Group 13 of the periodic table, or an oxide or carbonate thereof can be used as the electron donor. In particular, lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), ytterbium (Yb), indium (In), lithium oxide (Li₂O), cesium carbonate, or the like are preferably used. An alkali metal compound, such as Liq, can be used. An organic compound, such as tetrathianaphthacene, can be used as the electron donor. An organic compound containing a 1,3,4,6,7,8-tetrahydro-2H-pyrimido[1,2-a]pyrimidine skeleton, such asA compound containing 2hppSF, 2,7hpp2SF, or hpp2Py can be used as an electron donor. When any of these organic compounds is used as the electron donor, the electron transport material to be combined with the electron donor is preferably an organic compound comprising a heteroaromatic ring with a phenanthroline ring, such as bathophenanthroline (abbreviation: Bphen), bathocuproine (abbreviation: BCP), 2,9-di(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen), or 2,2'-(1,3-phenylene)bis(9-phenyl-1,10-phenanthroline) (abbreviation: mPPhen2P), in which case the operating voltage of the light-emitting device can be reduced.

[0255] If an electron transfer layer is provided in the charge generation layer 106 between a p-type layer and an electron injection buffer layer, the electron transfer layer contains at least one substance with electron transport properties and has a function for preventing interaction between the electron injection buffer layer and the p-type layer and for facilitating electron transfer. The LUMO level of the substance with electron transport properties in the electron transfer layer preferably lies between the LUMO level of the acceptor substance in the p-type layer and the LUMO level of the substance with electron transport properties in the electron transfer layer that is in contact with the charge generation layer 106.In particular, the LUMO level of the substance with electron transport properties in the electron conduction layer can be higher than or equal to -5.00 eV, preferably higher than or equal to -5.00 eV and lower than or equal to -3.00 eV. It should be noted that the substance with electron transport properties in the electron conduction layer is preferably a phthalocyanine-based material or a metal complex having a metal-oxygen bond and an aromatic ligand.

[0256] It should be noted that, with regard to light extraction efficiency, the charge-generating layer 106 preferably has a visible light transmittance (in particular, the charge-generating layer 106 preferably has a visible light transmittance of 40% or higher). The charge-generating layer 106 functions even if it has a lower conductivity than the first electrode 101 and the second electrode 102.

[0257] Although Fig. 3E represents the structure in which two of the organic compound layers 103 are arranged on top of each other, three or more EL layers can be arranged on top of each other, with charge-generating layers provided between each pair of adjacent EL layers. <cap-schicht>

[0258] Although in Fig. 3A to Fig. Not shown in Figure 3F, a cap layer can be provided over the second electrode 102 of the light-emitting device. For example, a material with a high refractive index can be used for the cap layer. Providing the cap layer over the second electrode 102 can improve the extraction efficiency of light emitted via the second electrode 102.

[0259] Specific examples of a material that can be used for the cap layer include 5,5'-Diphenyl-2,2'-di-5H-[1]benzothieno[3,2-c]carbazole (abbreviation: BisBTc) and 4,4',4''-(Benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II). <substrat>

[0260] The light-emitting device described in this embodiment can be formed on any number of different substrates. It should be noted that the type of substrate is not limited to any particular kind. Examples of substrates include semiconductor substrates (e.g., a single-crystal substrate and a silicon substrate), an SOI substrate, a glass substrate, a quartz substrate, a plastic substrate, a metal substrate, a stainless steel substrate, a substrate comprising a stainless steel foil, a tungsten substrate, a substrate comprising a tungsten foil, a flexible substrate, a mounting film and paper, or a base material film containing a fiber material.

[0261] Examples of the glass substrate include barium borosilicate glass, aluminum borosilicate glass, and soda-lime glass. Examples of the flexible substrate, affixing film, and base material film include plastics, typically polyethylene terephthalate (PET), polyethylene naphthalate (PEN), and polyethersulfone (PES); a synthetic resin, such as an acrylic resin, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyamide, polyimide, aramid, an epoxy resin, an evaporation-formed inorganic film, and paper.

[0262] For the fabrication of the light-emitting device in this embodiment, a gas-phase process, such as an evaporation process, or a liquid-phase process, such as a rotational coating process or an inkjet process, can be used. If an evaporation process is used, a physical vapor deposition (PVD) process, such as a sputtering process, an ion plating process, an ion beam evaporation process, a molecular beam evaporation process, or a vacuum evaporation process, a chemical vapor deposition (CVD) process, or the like can be employed.In particular, the layers with different functions (the hole injection layer 111, the hole transport layer 112, the light-emitting layer 113, the electron transport layer 114 and the electron injection layer 115) contained in the EL layers of the light-emitting device can be formed by an evaporation process (e.g. a vacuum evaporation process), a coating process (e.g. a dip coating process, a nozzle coating process, a rod coating process, a rotary coating process or a spray coating process), a printing process (e.g. an inkjet process, a screen printing (stencil printing), an offset printing (planographic printing), a flexographic printing (relief printing), an intaglio printing or a microcontact printing) or the like.

[0263] In cases where a film-forming process, such as a coating or printing process, is used, a high-molecular-weight compound (e.g., an oligomer, a dendrimer, or a polymer), a medium-molecular-weight compound (a compound between a low-molecular-weight compound and a high-molecular-weight compound with a molecular weight of 400 to 4000), an inorganic compound (e.g., a quantum dot material), or the like can be used. The quantum dot material can be a colloidal quantum dot material, an alloyed quantum dot material, a core-shell quantum dot material, a core-quantum quantum dot material, or the like.

[0264] Materials that can be used for the layers (the hole injection layer 111, the hole transport layer 112, the light-emitting layer 113, the electron transport layer 114 and the electron injection layer 115) contained in the organic compound layer 103 of the light-emitting device described in this embodiment are not limited to the materials described in this embodiment, and other materials can be used in combination as long as the functions of the layers are fulfilled.

[0265] The structures described in this embodiment can be used in a suitable combination with any of the structures described in the other embodiments. (Version 4)

[0266] In this embodiment, a display device of an embodiment of the present invention is based on Fig. 4A and Fig. 4B described in detail.

[0267] A display device 600 comprises a pixel section 177 in which a plurality of pixels 178 are arranged in a matrix. The pixel 178 comprises a subpixel 110R, a subpixel 110G and a subpixel 110B.

[0268] In this description and similar texts, for example, the common description of subpixels 110R, 110G, and 110B is sometimes given using the collective term "subpixel 110". Regarding other components that are to be distinguished from one another using letters of the alphabet, common features of the components are sometimes described using reference symbols without the letters of the alphabet.

[0269] Subpixel 110R emits red light, subpixel 110G emits green light, and subpixel 110B emits blue light. Therefore, an image can be displayed on pixel section 177. It should be noted that in this embodiment, three colors—red (R), green (G), and blue (B)—are given as examples of colors of light emitted by subpixels; however, subpixels of different combinations of colors can be used. The number of subpixels is not limited to three and can be four or more. Examples of four subpixels include subpixels emitting light of four colors: R, G, B, and white (W); subpixels emitting light of four colors: R, G, B, and Y; and four subpixels emitting light of R, G, B, and infrared (IR).

[0270] In this description and similar texts, the row direction and column direction are sometimes referred to as the X-direction and Y-direction, respectively. The X-direction and the Y-direction intersect each other and are, for example, perpendicular to each other.

[0271] Fig. Figure 4A 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. It should be noted that subpixels of different colors can be arranged in the Y direction and that subpixels of the same color can be arranged in the X direction.

[0272] Outside pixel section 177, a connection section 140 is provided, and an area 141 may also be provided. Area 141 is provided between pixel section 177 and connection section 140. The organic connection layer 103 is provided in area 141. A conductive layer 151C is provided in connection section 140.

[0273] Although Fig. As shown in Figure 4A, where area 141 and connecting section 140 are positioned on the right side of pixel section 177, the positions of area 141 and connecting section 140 are not particularly restricted. The number of areas 141 and the number of connecting sections 140 can each be one or more.

[0274] Fig. 4B is an example of a cross-sectional view along the dashed-dotted line A1-A2 in Fig. 4A. As in Fig. As shown in Figure 4A, the display device 600 comprises an insulating layer 171, a conductive layer 172 above the insulating layer 171, an insulating layer 173 above the insulating layer 171 and the conductive layer 172, an insulating layer 174 above the insulating layer 173, and the insulating layer 175 above the insulating layer 174. The insulating layer 171 is provided over a substrate (not shown). An opening reaching the conductive layer 172 is provided in the insulating layers 175, 174, and 173, and a terminal plug 176 is provided to fill the opening.

[0275] In pixel section 177, the light-emitting device 130 is provided above the insulating layer 175 and the terminal plug 176. A protective layer 135 is provided to cover the light-emitting device 130. A substrate 120 is bonded to the protective layer 135 by a resin layer 122. An inorganic insulating layer 125 and an insulating layer 127 above the inorganic insulating layer 125 are preferably provided between the adjacent light-emitting devices 130.

[0276] Although in the cross-sectional view in Fig. 4B Since the inorganic insulating layer 125 and the insulating layer 127 each appear as a plurality of layers, the inorganic insulating layer 125 and the insulating layer 127 are each preferably a continuous layer when the display device 600 is viewed from above. That is to say, the inorganic insulating layer 125 and the insulating layer 127 preferably comprise opening sections above first electrodes.

[0277] In Fig. Figure 4B shows a light-emitting device 130R, a light-emitting device 130G, and a light-emitting device 130B as light-emitting devices 130. The light-emitting devices 130R, 130G, and 130B emit light of different colors. For example, the light-emitting device 130R can emit red light, the light-emitting device 130G can emit green light, and the light-emitting device 130B can emit blue light. Alternatively, the light-emitting device 130R, the light-emitting device 130G, or the light-emitting device 130B can emit visible light of another color or infrared light.

[0278] The display device of an embodiment of the present invention can, for example, be a top-emission display device in which light is emitted in the direction opposite to that of a substrate above which light-emitting devices are formed. It should be noted that the display device of an embodiment of the present invention can also be a bottom-emission type.

[0279] Examples of a light-emitting substance contained in the light-emitting device 130 include organic compounds or organometallic complexes, such as a substance that emits fluorescent light (a fluorescent material), a substance that emits phosphorescent light (a phosphorescent material), and a substance that exhibits thermally activated delayed fluorescence (a thermally activated delayed fluorescence, TADF, material). Other examples include inorganic compounds (e.g., a quantum dot material).

[0280] The light-emitting device 130R has a structure as described in embodiment 3. The light-emitting device 130R comprises the first electrode (pixel electrode), which includes a conductive layer 151R and a conductive layer 152R, an organic compound layer 103R over the first electrode, a common layer 104 over the organic compound layer 103R, and a common electrode 155 over the common layer 104. The common electrode 155 corresponds to the second electrode 102 of embodiments 2 and 3. Although the common layer 104 is not necessarily provided, it is preferably provided to reduce damage to the organic compound layer 103R during processing. In the case where the common layer 104 is provided, it is preferably an electron injection layer.

[0281] The light-emitting device 130G has a structure as described in embodiment 3. The light-emitting device 130G comprises the first electrode (pixel electrode), which includes a conductive layer 151G and a conductive layer 152G, an organic compound layer 103G over the first electrode, the common layer 104 over the organic compound layer 103G, and the common electrode 155 over the common layer 104. The common electrode 155 corresponds to the second electrode 102 of embodiments 2 and 3. Although the common layer 104 is not necessarily provided, it is preferably provided to reduce damage to the organic compound layer 103G during processing.

[0282] The light-emitting device 130B has a structure as described in embodiment 3. The light-emitting device 130B comprises the first electrode (pixel electrode), which includes a conductive layer 151B and a conductive layer 152B, an organic compound layer 103B over the first electrode, the common layer 104 over the organic compound layer 103B, and the common electrode 155 over the common layer 104. The common electrode 155 corresponds to the second electrode 102 of embodiments 2 and 3. Although the common layer 104 is not necessarily provided, it is preferably provided to reduce damage to the organic compound layer 103B during processing.

[0283] In the light-emitting device, one of the pixel electrodes and the common electrode serve as the anode, and the other serves as the cathode. The following description assumes that the pixel electrode serves as the anode and the common electrode as the cathode, unless otherwise specified.

[0284] The organic compound layers 103R, 103G, and 103B are island-shaped layers insulated either by a light-emitting device or by an emissive paint. By providing the island-shaped organic compound layer 103 in each of the light-emitting devices 130, leakage current between adjacent light-emitting devices 130 can be prevented, even in a high-resolution display. This prevents crosstalk, enabling a display with very high contrast. In particular, a display with high power efficiency at low luminance can be obtained.

[0285] The island-shaped organic compound layer 103 is formed by creating an EL film and processing the EL film using a lithographic process. It should be noted that the organic compound layer 103 is sometimes referred to as the EL layer.

[0286] In the display device of an embodiment of the present invention, the first electrode (pixel electrode) of the light-emitting device preferably has a multilayered structure. For example, in the Fig. In the example shown in Figure 4B, the first electrode of the light-emitting device 130 comprises a layer arrangement of the conductive layer 151 (conducting layers 151R, 151G, and 151B) and the conductive layer 152 (conducting layers 152R, 152G, and 152B). In the case where, for example, the display device 600 is a top-emission type and the pixel electrode of the light-emitting device 130 serves as the anode, the conductive layer 151 preferably has a high reflectivity for visible light, and the conductive layer 152 preferably has a transmittance for visible light and a high work function. The higher the reflectivity for visible light of the pixel electrode, the higher the extraction efficiency of the light emitted by the organic compound layer 103 when the display device 600 is a top-emission type.The higher the work function of the pixel electrode, the easier it is to inject holes into the organic compound layer 103 when the pixel electrode acts as the anode. Consequently, if the pixel electrode of the light-emitting device 130 is a layer arrangement consisting of the conductive layer 151 with high reflectivity for visible light and the conductive layer 152 with a high work function, the light-emitting device 130 can exhibit high light extraction efficiency and a low operating voltage. In this description and similar passages, the conductive layers 151R, 151G, and 151B are sometimes described using the collective term "conductive layer 151".

[0287] In the case where the conductive layer 151 has a high reflectivity for visible light, the reflectivity for visible light of the conductive layer 151 is preferably higher than or equal to 40% and lower than or equal to 100%, or higher than or equal to 70% and lower than or equal to 100%. If the conductive layer 152 is used as an electrode with a transmittance property for visible light, it preferably has, for example, a transmittance for visible light of higher than or equal to 40%.

[0288] If such a pixel electrode is a layered arrangement consisting of a large number of layers, the quality of which could change, for example, as a result of a reaction between the layers. If, for instance, a film formed after the pixel electrode is created is removed by a wet etching process, contact with a chemical solution could cause galvanic corrosion.

[0289] Therefore, in this embodiment of the display device 600, an insulating layer 156 (insulating layers 156R, 156G, and 156B) is preferably formed on the side surfaces of the conductive layers 151 and 152. This prevents a chemical solution from coming into contact with the conductive layer 151, for example, when a film formed after the formation of the pixel electrode, which comprises the conductive layer 151 and the conductive layer 152, is removed by a wet etching process. Accordingly, the occurrence of galvanic corrosion in the pixel electrode, for example, can be prevented. This allows the display device 600 to be manufactured using a high-yield process and is therefore cost-effective. Furthermore, the generation of a defect in the display device 600 can be prevented, making the display device 600 very reliable.In this description and the like, the common description of the conducting layers 156R, 156G and 156B is in some cases given using the collective term “conducting layer 156”.

[0290] A metallic material can be used, for example, for the conductive layer 151. In particular, it is possible to use, for example, a metal 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), or neodymium (Nd), or an alloy containing a suitable combination of any of these metals.

[0291] For the conductive layer 152, an oxide containing one or more selected elements from indium, tin, zinc, gallium, titanium, aluminum, and silicon can be used. For example, a conductive oxide containing one or more of the following is preferably used: 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, indium zinc oxide containing silicon, and the like. In particular, an indium tin oxide containing silicon can be used suitablely for the conductive layer 152 because, for example, it has a work function of 4.0 eV or higher.

[0292] The conductive layer 151 and the conductive layer 152 can each be a layer arrangement consisting of multiple layers containing different materials. In this case, the conductive layer 151 can include a layer formed using a material that can be used for the conductive layer 152, such as a conductive oxide. Furthermore, the conductive layer 152 can include a layer formed using a material that can be used for the conductive layer 151, such as a metallic material. If the conductive layer 151 is a layer arrangement of two or more layers, for example, a layer in contact with the conductive layer 152 can be formed using a material that can be used for the conductive layer 152.

[0293] The structure described in this embodiment can be used in a suitable combination with any of the structures described in other embodiments. (Version 5)

[0294] This embodiment describes a display device of an embodiment of the present invention.

[0295] The display device of this embodiment can be a high-resolution display device. Therefore, in this embodiment, the display device can be used for display sections of information terminal devices (portable devices), such as information terminal devices in the form of a wristwatch or bracelet, and display sections of portable devices that can be worn on the head, such as a VR device, like a head-mounted display (HMD), and a glasses-like AR device.

[0296] The display device in this embodiment can be a high-definition display device or a large display device. Accordingly, the display device in this embodiment can be used for display sections of a digital camera, a digital video camera, a digital photo frame, a mobile phone, a portable game console, a portable information terminal, and an audio playback device, in addition to display sections of electronic devices with a relatively large screen, such as a television, desktop and laptop PCs, a computer monitor, and the like, digital signage, and a large gaming machine, such as a pinball machine. [Display module]

[0297] Fig. Figure 5A is a perspective view of a display module 280. The display module 280 comprises a display device 600A and an FPC 290. It should be noted that the display device included in the display module 280 is not limited to the display device 600A and can be any of the display devices 600B to 600F described below.

[0298] The display module 280 comprises a substrate 291 and a substrate 292. The display module 280 includes a display section 281. The display section 281 is an area of ​​the display module 280 on which an image is displayed and is an area in which light emitted by pixels provided in a pixel section 284 to be described can be seen.

[0299] Fig. Figure 5B is a perspective view schematically illustrating the structure on the side of substrate 291. Above substrate 291 are arranged a circuit section 282, a pixel circuit section 283 above circuit section 282, and pixel section 284 above pixel circuit section 283. Additionally, a connection section 285 for connecting to the FPC 290 is included in a section above substrate 291 that does not overlap with pixel section 284. Connection section 285 and circuit section 282 are electrically connected to each other via a conductor section 286, which is formed from a plurality of conductors.

[0300] Pixel section 284 comprises a multitude of pixels 284a arranged periodically. An enlarged view of a pixel 284a is shown on the right in Fig. 5B is shown. Any of the structures described in the preceding embodiments can be applied to pixel 284a. Fig. 5B provides an example in which pixel 284a has a structure similar to that of the one in Fig. 4A shows pixel 178, which is similar to the pixel shown.

[0301] The pixel circuit section 283 comprises a plurality of pixel circuits 283a that are arranged periodically.

[0302] A pixel circuit 283a is a circuit that controls the operation of a variety of elements contained within a pixel 284a. For example, the pixel circuit 283a may include at least one selector transistor, one current-control transistor (driver transistor), and one capacitor per light-emitting device. A gate signal is input to a gate of the selector transistor, and a video signal is input to a source and drain terminal of the selector transistor. Thus, an active-matrix display device is achieved.

[0303] Circuit section 282 comprises a circuit for operating the pixel circuits 283a in pixel circuit section 283. For example, circuit section 282 preferably comprises a gate line driver circuit and / or a source line driver circuit. Circuit section 282 may also include at least one arithmetic circuit, a memory circuit, a power supply circuit, and the like.

[0304] The FPC 290 serves as a conduit for supplying an external video signal, power supply potential, or the like to circuit section 282. An IC can be mounted on the FPC 290.

[0305] The display module 280 can have a structure in which the pixel circuit section 283 and / or the circuit section 282 are arranged below the pixel section 284; therefore, the aperture ratio (the effective display area ratio) of the display section 281 can be significantly high. For example, the aperture ratio of the display section 281 can be greater than or equal to 40% and less than 100%, preferably greater than or equal to 50% and less than or equal to 95%, and more preferably greater than or equal to 60% and less than or equal to 95%. Furthermore, the pixels 284a can be arranged very densely, and therefore the display section 281 can have a very high definition.For example, the pixels 284a in the display section 281 are arranged such that they have a definition of preferably higher than or equal to 2000 ppi, more preferably higher than or equal to 3000 ppi, even more preferably higher than or equal to 5000 ppi, even more preferably higher than or equal to 6000 ppi and lower than or equal to 20000 ppi or lower than or equal to 30000 ppi.

[0306] Such a display module 280 has a very high resolution and can therefore be used in a VR device, such as a head-mounted display (HMD) or a glasses-like AR device. For example, even in the case of a structure where the display section of the display module 280 is viewed through a lens, the pixels of the very high-resolution display section 281 contained in the display module 280 are prevented from being detected when the display section is magnified by the lens, thus enabling the display to provide a high level of immersion. However, the display module 280 can also be used in electronic devices that include a relatively small display section. For example, the display module 280 can be advantageously used in the display section of a wearable electronic device, such as a wristwatch. [Display device 600A]

[0307] The in Fig. The display device 600A shown in Figure 6A comprises a substrate 301, the light-emitting devices 130R, 130G and 130B, a capacitor 240 and a transistor 310.

[0308] Substrate 301 corresponds to substrate 291 in Fig. 5A and Fig. 5B. The transistor 310 comprises a channel-forming region in the substrate 301. The substrate 301 can be, for example, a semiconductor substrate such as a single-crystal silicon substrate. The transistor 310 comprises a portion of the substrate 301, a conductive layer 311, a low-resistance region 312, an insulating layer 313, and an insulating layer 314. The conductive layer 311 serves as the gate electrode. The insulating layer 313 is positioned between the substrate 301 and the conductive layer 311 and serves as the gate insulating layer. The low-resistance region 312 is a region in which the substrate 301 is doped with an impurity and serves as the source or drain. The insulating layer 314 is provided such that it covers the side face of the conductive layer 311.

[0309] An element insulating layer 315 is provided between two adjacent transistors 310 such that it is embedded in the substrate 301.

[0310] An insulating layer 261 is provided such that it covers the transistor 310, and the capacitor 240 is provided above the insulating layer 261.

[0311] The capacitor 240 comprises a conductive layer 241, a conductive layer 245, and an insulating layer 243 between the conductive layers 241 and 245. The conductive layer 241 serves as one electrode of the capacitor 240, the conductive layer 245 serves as the other electrode of the capacitor 240, and the insulating layer 243 serves as the dielectric of the capacitor 240.

[0312] The conductive layer 241 is provided above the insulating layer 261 and is embedded in an insulating layer 254. The conductive layer 241 is electrically connected to a terminal of the source and drain of the transistor 310 via a terminal plug 271 embedded in the insulating layer 261. The insulating layer 243 is provided such that it covers the conductive layer 241. The conductive layer 245 is provided in a region that overlaps with the conductive layer 241, with the insulating layer 243 lying between them.

[0313] An insulating layer 255 is provided such that it covers the capacitor 240. The insulating layer 174 is provided over the insulating layer 255. The insulating layer 175 is provided over the insulating layer 174. The light-emitting devices 130R, 130G, and 130B are provided over the insulating layer 175. Fig. 6A provides an example in which the light-emitting devices 130R, 130G and 130B each exhibit the properties described in Fig. Figure 1A shows a multilayered structure. An insulator is provided in areas between adjacent light-emitting devices. For example, in Fig. 6A the inorganic insulating layer 125 and the insulating layer 127 above the inorganic insulating layer 125 are provided in these areas.

[0314] The insulating layer 156R is provided such that it comprises an area overlapping the side surface of the conductive layer 151R of the light-emitting device 130R. The insulating layer 156G is provided such that it comprises an area overlapping the side surface of the conductive layer 151G of the light-emitting device 130G. The insulating layer 156B is provided such that it comprises an area overlapping the side surface of the conductive layer 151B of the light-emitting device 130B. The conductive layer 152R is provided such that it covers the conductive layer 151R and the insulating layer 156R. The conductive layer 152R is provided such that it covers the conductive layer 151R and the insulating layer 156R. The conductive layer 152G is provided in such a way that it covers the conductive layer 151G and the insulating layer 156G.The conductive layer 152B is provided such that it covers the conductive layer 151B and the insulating layer 156B. The sacrificial layer 158R is positioned over the organic compound layer 103R. The sacrificial layer 158G is positioned over the organic compound layer 103G. A sacrificial layer 158R is positioned over the organic compound layer 103R of the light-emitting device 130R. A sacrificial layer 158G is positioned over the organic compound layer 103G of the light-emitting device 130G. A sacrificial layer 158B is positioned over the organic compound layer 103B of the light-emitting device 130B.

[0315] Each of the conductive layers 151R, 151G, and 151B is electrically connected to a source and drain terminal of the corresponding transistor 310 via a terminal plug 256 embedded in the insulating layers 243, 255, 174, and 175, the conductive layer 241 embedded in the insulating layer 254, and the terminal plug 271 embedded in the insulating layer 261. The top of the insulating layer 175 is at the same level, or substantially at the same level, as the top of the terminal plug 256. Any number of different conductive materials can be used for the terminal plugs.

[0316] The protective layer 135 is provided via the light-emitting devices 130R, 130G, and 130B. A substrate 120 is bonded to the protective layer 135 by a resin layer 122. Reference can be made to embodiment 4 for details of the light-emitting device 130 and the components above it up to the substrate 120. The substrate 120 corresponds to substrate 292 in Fig. 5A.

[0317] Fig. 6B presents a variation example of the in Fig. The display device 600A shown in 6A. The one in Fig. The light-emitting device shown in Figure 6B comprises the color layers 136R, 136G, and 136B, and each of the light-emitting devices 130 comprises an area that overlaps with one of the color layers 136R, 136G, and 136B. In the Fig. In the display device shown in Figure 6B, the light-emitting device 130 can, for example, emit white light. For example, the color layer 136R, the color layer 136G, and the color layer 136B can transmit red light, green light, and blue light, respectively. [Display device 600B]

[0318] Fig. Figure 7 is a perspective view of the display device 600B, and Fig. Figure 8A is a cross-sectional view of the display device 600B.

[0319] In the display device 600B, a substrate 352 and a substrate 351 are bonded together. Fig. In Figure 7, substrate 352 is represented by a dashed line.

[0320] The display device 600B comprises the pixel section 177, the connecting section 140, a circuit 356, a line 355 and the like. Fig. Figure 7 shows an example in which an integrated circuit (IC) 354 and an FPC 353 are mounted on the display device 600B. Therefore, the Fig. The structure shown in Figure 7 can be considered a display module comprising the display device 600B, the IC, and the FPC. Here, a display device in which a substrate is equipped with a connecting element, such as an FPC, or mounted with an IC, is referred to as a display module.

[0321] The connection section 140 is provided outside of the pixel section 177. The connection section 140 can be provided along one side or multiple sides of the pixel section 177. The number of connection sections 140 can be one or more. Fig. Figure 7 presents an example in which the connecting section 140 is provided such that it encloses the four sides of the pixel section 177. In the connecting section 140, a common electrode of a light-emitting device is electrically connected to a conductive layer so that a potential can be applied to the common electrode.

[0322] Circuit 356 can, for example, be used as a sampling line driver circuit.

[0323] Line 355 serves to supply a signal and current to pixel section 177 and circuit 356. The signal and current are input to line 355 externally via FPC 353 or IC 354.

[0324] Fig. Figure 7 presents an example in which IC 354 is provided to substrate 351 by a chip-on-glass (COG) process, a chip-on-film (COF) process, or the like. IC 354 could, for example, be an IC comprising a sampling line driver circuit, a signal line driver circuit, or the like. It should be noted that the display device 600B and the display module are not necessarily provided with an IC. Alternatively, the IC could, for example, be mounted on the FPC by a COF process.

[0325] Fig. Figure 8A shows an example of cross-sections of part of an area comprising the FPC 353, part of the circuit 356, part of the pixel section 177, part of the connection section 140 and part of an area comprising an end section, the display device 600B.

[0326] The in Fig. 8A Display device 600B comprises a transistor 201, a transistor 205, the light-emitting device 130R which emits red light, the light-emitting device 130G which emits green light, the light-emitting device 130B which emits blue light, and the like between the substrate 351 and the substrate 352.

[0327] The multilayered structure of each of the light-emitting devices 130R, 130G and 130B is the same as that which is in Fig. Figure 1A is shown, with the exception of the structure of the pixel electrode. For details of the light-emitting devices, reference can be made to the preceding embodiments.

[0328] Light-emitting device 130R comprises a conductive layer 224R, a conductive layer 151R above conductive layer 224R, and a conductive layer 152R above conductive layer 151R. Light-emitting device 130G comprises a conductive layer 224G, a conductive layer 151G above conductive layer 224G, and a conductive layer 152G above conductive layer 151G. Light-emitting device 130B comprises a conductive layer 224B, a conductive layer 151B above conductive layer 224B, and a conductive layer 152B above conductive layer 151B. Here, the conductive layers 224R, 151R, and 152R can be collectively referred to as the pixel electrode of light-emitting device 130R. The conductive layers 151R and 152R, with the exception of the conductive layer 224R, can also be referred to as the pixel electrode of the light-emitting device 130R.Similarly, the conductive layers 224G, 151G, and 152G can be collectively referred to as the pixel electrode of the light-emitting device 130G; the conductive layers 151G and 152G, with the exception of conductive layer 224G, can also be referred to as the pixel electrode of the light-emitting device 130G. The conductive layers 224B, 151B, and 152B can be collectively referred to as the pixel electrode of the light-emitting device 130B; the conductive layers 151B and 152B, with the exception of conductive layer 224B, can also be referred to as the pixel electrode of the light-emitting device 130B.

[0329] The conductive layer 224R is connected via an opening provided in an insulating layer 214 to a conductive layer 222b contained in the transistor 205. An end section of the conductive layer 151R is positioned further outward than an end section of the conductive layer 224R. The insulating layer 156R is provided such that it includes an area in contact with the side face of the conductive layer 151R, and the conductive layer 152R is provided such that it covers the conductive layer 151R and the insulating layer 156R.

[0330] The conductive layers 224G, 151G and 152G and the insulating layer 156G in the light-emitting device 130G are not described in detail, as they are each similar to the conductive layers 224R, 151R and 152R and the insulating layer 156R in the light-emitting device 130R; the same applies to the conductive layers 224B, 151B and 152B and the insulating layer 156B in the light-emitting device 130B.

[0331] The conductive layers 224R, 224G and 224B each have a recessed section that covers the opening provided in the insulating layer 214. A layer 128 is embedded in the recessed section.

[0332] Layer 128 serves to fill the recessed areas of conductive layers 224R, 224G, and 224B to maintain planarity. Above conductive layers 224R, 224G, and 224B, as well as layer 128, conductive layers 151R, 151G, and 151B are provided, each electrically connected to conductive layers 224R, 224G, and 224B. Therefore, the areas overlapping the recessed areas of conductive layers 224R, 224G, and 224B can also be used as light-emitting regions, thereby increasing the pixel aperture ratio.

[0333] Layer 128 can be an insulating layer or a conductive layer. Any of various inorganic insulating materials, organic insulating materials, and conductive materials can be suitably used for layer 128. In particular, layer 128 is preferably formed using an insulating material, and more specifically, preferably using an organic insulating material. Layer 128 can, for example, be formed using an organic insulating material that is suitable for insulating layer 127.

[0334] The protective layer 135 is provided over the light-emitting devices 130R, 130G, and 130B. The protective layer 135 and the substrate 352 are bonded together with an adhesive layer 142. The substrate 352 is provided with an opaque layer 157. A solid sealing structure, a hollow sealing structure, or the like can be used to seal the light-emitting device 130. Fig. 8A employs a solid sealing structure in which a space between substrate 352 and substrate 351 is filled with the adhesive layer 142. Alternatively, the space can be filled with an inert gas (e.g., nitrogen or argon), i.e., a hollow sealing structure can be used. In this case, the adhesive layer 142 can be provided in a frame form such that it does not overlap with the light-emitting device. Furthermore, the space can be filled with a resin other than the frame-shaped adhesive layer 142.

[0335] Fig. Figure 8A shows an example in which the interconnect section 140 comprises 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. In the Fig. In the example shown in Figure 8A, the insulating layer 156C is provided such that it covers an area that overlaps with the side surface of the conductive layer 151C.

[0336] The display device 600B has a top-emission structure. Light from the light-emitting device is emitted towards the substrate 352. The substrate 352 is preferably made of a material with high transmittance for visible light. The pixel electrode contains a material that reflects visible light, and a counter electrode (the common electrode 155) contains a material that transmits visible light.

[0337] Transistor 201 and transistor 205 are formed on substrate 351. These transistors can be formed using the same materials and in the same steps.

[0338] An insulating layer 211, an insulating layer 213, an insulating layer 215, and an insulating layer 214 are provided above the substrate 351 in that order. A portion of the insulating layer 211 serves as the gate insulating layer of each transistor. A portion of the insulating layer 213 also serves as the gate insulating layer of each transistor. The insulating layer 215 is provided in such a way that it covers the transistors. The insulating layer 214 is provided in such a way that it covers the transistors and functions as a planarization layer. It should be noted that the number of gate insulating layers and the number of insulating layers covering the transistors are not limited, and there can be one or more of each.

[0339] A material that does not readily allow the diffusion of impurities, such as water and hydrogen, is preferably used for at least one of the insulating layers covering the transistors. This is because such an insulating layer can act as a barrier layer. With such a structure, the diffusion of external impurities into the transistors can be effectively prevented, thus improving the reliability of a display device.

[0340] An inorganic insulating film is preferably used as any of the insulating layers 211, 213, and 215. For example, a silicon nitride film, a silicon oxynitride film, a silicon oxide film, a silicon nitride oxide film, an aluminum oxide film, or an aluminum nitride film can be used as the inorganic insulating film. A hafnium oxide film, a yttrium oxide film, a zirconium oxide film, a gallium oxide film, a tantalum oxide film, a magnesium oxide film, a lanthanum oxide film, a cerium oxide film, a neodymium oxide film, or the like can also be used. Two or more of the aforementioned insulating films can also be arranged one above the other.

[0341] An organic insulating layer is suitable as insulating layer 214, serving as a planarizing layer. Examples of materials that can be used for the organic insulating layer include an acrylic resin, a polyimide resin, an epoxy resin, a polyamide resin, a polyimidamide resin, a siloxane resin, a benzocyclobutene-based resin, a phenolic resin, and precursors of these resins. The insulating layer 214 can have a multilayer structure consisting of an organic insulating layer and an inorganic insulating layer. The outermost layer of the insulating layer 214 preferably serves as an etch-resistant layer. This can prevent the formation of a depression in the insulating layer 214 during the processing of the conductive layer 224R, 151R, or 152R, or the like. Alternatively, a depression in the insulating layer 214 can be provided during the processing of the conductive layer 224R, 151R, or 152R, or the like.

[0342] Transistors 201 and 205 each comprise a conductive layer 221, which serves as the gate; an insulating layer 211, which serves as the gate insulating layer; a conductive layer 222a and a conductive layer 222b, which serve as the source and drain, respectively; a semiconductor layer 231; an insulating layer 213, which serves as the gate insulating layer; and a conductive layer 223, which serves as the gate. Here, multiple layers obtained by processing the same conductive film are represented by the same hatching pattern. The insulating layer 211 is positioned between the conductive layer 221 and the semiconductor layer 231. The insulating layer 213 is positioned between the conductive layer 223 and the semiconductor layer 231.

[0343] There is no particular restriction regarding the structure of the transistors included in the display device of this embodiment. For example, a planar transistor, a staggered transistor, or an inverted staggered transistor can be used. A top-gate transistor or a bottom-gate transistor can also be used. Alternatively, gates can be provided above and below a semiconductor layer in which a channel is formed.

[0344] The structure, in which the semiconductor layer forming a channel is provided between two gates, is used for each of transistors 201 and 205. The two gates can be connected together and supplied with the same signal to operate the transistor. Alternatively, the transistor's threshold voltage can be controlled by applying a threshold-control potential to one of the two gates and an operating potential to the other.

[0345] There is no particular restriction regarding the crystallinity of a semiconductor material used for the transistors, and either an amorphous semiconductor or a semiconductor with crystallinity (a microcrystalline semiconductor, a polycrystalline semiconductor, a single-crystal semiconductor, or a semiconductor that partially comprises crystalline regions) can be used. Preferably, a semiconductor with crystallinity is used, in which case a deterioration of the transistor properties can be prevented.

[0346] The semiconductor layer of the transistor preferably contains a metal oxide. This means that a transistor containing a metal oxide in its channel-forming region (hereinafter referred to as an OS transistor) is preferably used in the display device of this embodiment.

[0347] Examples of an oxide semiconductor with crystallinity include a c-axis aligned crystalline oxide semiconductor (CAAC-OS) and a nanocrystalline oxide semiconductor (nc-OS).

[0348] Alternatively, a transistor containing silicon in its channel-forming region (a silicon transistor) can be used. Examples of silicon include monocrystalline silicon, polycrystalline silicon, and amorphous silicon. In particular, a transistor containing low-temperature polysilicon (LTPS) in its semiconductor layer (hereinafter also referred to as an LTPS transistor) can be used. The LTPS transistor exhibits high field-effect mobility and advantageous frequency characteristics.

[0349] Using silicon transistors, such as LTPS transistors, a circuit requiring high-frequency operation (e.g., a source driver circuit) can be implemented on the same substrate as the display section. This simplifies the external circuitry mounted on the display device and reduces component and assembly costs.

[0350] An open-circuit transistor (OS transistor) exhibits a much higher field-effect mobility than a transistor containing amorphous silicon. Furthermore, the OS transistor has a very low leakage current between a source and a drain in the off-state, and charges accumulated in a capacitor connected in series with the transistor can be retained for extended periods. Additionally, the use of an OS transistor can reduce the power consumption of the display device.

[0351] To increase the luminance of the light-emitting device in the pixel circuit, the amount of current flowing through the light-emitting device must be increased. To increase the current, the source-drain voltage of a driver transistor in the pixel circuit must be increased. An OS transistor has a higher voltage rating between its source and drain than a Si transistor; therefore, a higher voltage can be applied between the source and drain of the OS transistor. Thus, when an OS transistor is used as the driver transistor in the pixel circuit, the amount of current flowing through the light-emitting device can be increased, thereby increasing its luminance.

[0352] Regarding the saturation characteristics of a current flowing when transistors operate in a saturation region, even if the source-drain voltage of an OS transistor gradually increases, a more stable current (saturation current) can be conducted through the OS transistor than through a Si transistor. Therefore, using an OS transistor as a driver transistor allows a stable current to be conducted through light-emitting devices, even if, for example, the current-voltage characteristics of the light-emitting devices vary. In other words, when the OS transistor operates in the saturation region, the source-drain current changes very little with an increase in the source-drain voltage; thus, the luminance of the light-emitting device can remain stable.

[0353] As described above, by using OS transistors as driver transistors included in the pixel circuits, it is possible, for example, to suppress degradation of the black level, increase the luminance, increase the number of gray levels, and suppress fluctuations of light-emitting devices.

[0354] For example, the semiconductor layer preferably contains indium, M (M is one or more of gallium, aluminum, silicon, boron, yttrium, tin, copper, vanadium, beryllium, titanium, iron, nickel, germanium, zirconium, molybdenum, lanthanum, cerium, neodymium, hafnium, tantalum, tungsten, and magnesium), and zinc. In particular, M is preferably one or more of aluminum, gallium, yttrium, and tin.

[0355] For the semiconductor layer, an oxide containing indium (In), gallium (Ga), and zinc (Zn) (also known as IGZO) is particularly preferred. An oxide containing indium, tin, and zinc is preferred. An oxide containing indium, gallium, tin, and zinc is preferred. An oxide containing indium (In), aluminum (Al), and zinc (Zn) (also known as IAZO) is preferred. An oxide containing indium (In), aluminum (Al), gallium (Ga), and zinc (Zn) (also known as IAGZO) is preferred. Alternatively, an oxide containing indium (also known as IO) is preferred.

[0356] If the semiconductor layer is an In-M-Zn oxide, the atomic fraction of In is preferably higher than or equal to the atomic fraction of M in the In-M-Zn oxide. Examples of the atomic ratios of the metal elements in such an In-M-Zn oxide are In:M:Zn = 1:1:1, 1:1:1.2, 2:1:3, 3:1:2, 4:2:3, 4:2:4.1, 5:1:3, 5:1:6, 5:1:7, 5:1:8, 6:1:6, and 5:2:5, and a composition close to any of the above atomic ratios. It should be noted that "close to the atomic ratio" includes 30% of an intended atomic ratio.

[0357] If the atomic ratio is described as In:Ga:Zn = 4:2:3 or a composition close to it, this includes the case where the atomic fraction of Ga is greater than or equal to 1 and less than or equal to 3, and the atomic fraction of Zn is greater than or equal to 2 and less than or equal to 4, where the atomic fraction of In is 4. Furthermore, if the atomic ratio is described as In:Ga:Zn = 5:1:6 or a composition close to it, this includes the case where the atomic fraction of Ga is greater than 0.1 and less than or equal to 2, and the atomic fraction of Zn is greater than or equal to 5 and less than or equal to 7, where the atomic fraction of In is 5.Furthermore, if the atomic ratio is described as In:Ga:Zn = 1:1:1 or a composition close to it, the case is included in which the atomic fraction of Ga is greater than 0.1 and less than or equal to 2 and the atomic fraction of Zn is greater than 0.1 and less than or equal to 2, where the atomic fraction of In is 1.

[0358] The transistors contained in circuit 356 and the transistors contained in pixel section 177 may have the same structure or different structures. One structure, or two or more types of structures, may be used for a variety of transistors contained in circuit 356. Similarly, one structure, or two or more types of structures, may be used for a variety of transistors contained in pixel section 177.

[0359] All transistors contained in pixel section 177 can be OS transistors, or all transistors contained in pixel section 177 can be Si transistors. Alternatively, some of the transistors contained in pixel section 177 can be OS transistors, and the others can be Si transistors.

[0360] For example, if both an LTPS transistor and an OS transistor are used in pixel section 177, the display device can exhibit low power consumption and high drive capability. It should be noted that a structure using an LTPS transistor and an OS transistor in combination is sometimes referred to as an LTPO. For instance, it is preferred that an OS transistor be used as a switch to control an electrical connection between lines, and an LTPS transistor be used as a current-controlling transistor.

[0361] For example, a transistor contained in pixel section 177 serves as a transistor for controlling the current flowing through the light-emitting device and can be referred to as a driver transistor. A source and drain terminal of the driver transistor are electrically connected to the pixel electrode of the light-emitting device. An LTPS transistor is preferably used as the driver transistor. In this case, the amount of current flowing through the light-emitting device can be increased in the pixel circuit.

[0362] Another transistor, contained within pixel section 177, acts as a switch to control whether a pixel is selected or not and can also be called a selection transistor. One gate of the selection transistor is electrically connected to a gate line, and one terminal of its source and drain are electrically connected to a source line (signal line). An OS transistor is preferably used as the selection transistor. In this case, the gray level of the pixel itself can be maintained at a very low frame rate (e.g., less than or equal to 1 fps), thus reducing power consumption by stopping the driver when displaying a still image.

[0363] As described above, the display device of an embodiment of the present invention can all have a high aperture ratio, high resolution, high display quality and low power consumption.

[0364] It should be noted that the display device of one embodiment of the present invention has a structure comprising the OS transistor and the light-emitting device with a metal maskless (MML) structure. This structure can greatly reduce leakage current that could flow through a transistor and leakage current that could flow between adjacent light-emitting devices (in some cases referred to as horizontal or lateral leakage current). By displaying images on the display device with this structure, the viewer can be provided with one or more of the crispness, sharpness, high color saturation, and high contrast ratio of an image.If a leakage current that could flow through the transistor and a lateral leakage current that could flow between the light-emitting devices are very low, light leakage during black display (deterioration of the black level) or the like can be minimized.

[0365] In particular, in the case where a side-by-side (SBS) structure, which is the structure described above for the separate formation or coloration of light-emitting layers, is used in a light-emitting device with an MML structure, a layer provided between light-emitting devices (for example, also referred to as an organic layer or common layer shared by the light-emitting devices) is separated; consequently, lateral leakage current can be prevented or be very low.

[0366] Fig. 8B and Fig. 8C represents further structural examples of transistors.

[0367] Transistors 209 and 210 each comprise the conductive layer 221, which serves as the gate; the insulating layer 211, which serves as the gate insulating layer; the semiconductor layer 231, which includes a channel-forming region 231i and a pair of low-resistance regions 231n; the conductive layer 222a, which is connected to one of the pair of low-resistance regions 231n; the conductive layer 222b, which is connected to the other of the pair of low-resistance regions 231n; an insulating layer 225, which serves as the gate insulating layer; the conductive layer 223, which serves as the gate; and the insulating layer 215, which covers the conductive layer 223. The insulating layer 211 is positioned between the conductive layer 221 and the channel-forming region 231i. The insulating layer 225 is positioned at least between the conductive layer 223 and the channel-forming region 231i. Furthermore, an insulating layer 218 covering the transistor can be provided.

[0368] Fig. Figure 8B represents an example of transistor 209, in which the insulating layer 225 covers the top and side surfaces of semiconductor layer 231. The conductive layer 222a and the conductive layer 222b are connected to the corresponding low-resistance regions 231n via openings provided in the insulating layer 225 and the insulating layer 215. One of the conductive layers 222a and 222b serves as the source and the other as the drain.

[0369] In the Fig. In transistor 210 shown in Figure 8C, the insulating layer 225 overlaps with the channel-forming region 231i of the semiconductor layer 231, but not with the low-resistance regions 231n. For example, the Fig. The structure shown in Figure 8C can be obtained by processing the insulating layer 225 using the conductive layer 223 as a mask. Fig. 8C provides the insulating layer 215 to cover the insulating layer 225 and the conductive layer 223, and the conductive layer 222a and the conductive layer 222b are connected to the corresponding low-resistance regions 231n via openings in the insulating layer 215.

[0370] A connection section 204 is provided in an area of ​​substrate 351 that does not overlap with substrate 352. In the connection section 204, the conductor 355 is electrically connected to the FPC 353 via a conductive layer 166 and a connection layer 242. As an example, the conductive layer 166 has a multilayer structure consisting of a conductive film obtained by processing the same conductive film as conductive layers 224R, 224G, and 224B; a conductive film obtained by processing the same conductive film as conductive layers 151R, 151G, and 151B; and a conductive film obtained by processing the same conductive film as conductive layers 152R, 152G, and 152B. The conductive layer 166 is exposed at the top of the connection section 204. Thus, the connection section 204 and the FPC 353 can be electrically connected to each other via the connection layer 242.

[0371] The opaque layer 157 is preferably provided on the surface of the substrate 352 on the side of the substrate 351. The opaque layer 157 can be provided over an area between adjacent light-emitting devices, in the connecting section 140, in the circuit 356, and the like. Various optical components can be arranged on the outside of the substrate 352.

[0372] A material that can be used for substrate 120 can be used for each of substrates 351 and 352.

[0373] A material that can be used for the resin layer 122 can also be used for the adhesive layer 142.

[0374] An anisotropic conductive film (ACF), anisotropic conductive paste (ACP), or the like can be used as the connecting layer 242. [Display device 600C]

[0375] The in Fig. The display device 600C shown in 9 differs from the one in Fig. The display device 600B shown in 8A is distinguished mainly by the fact that it has a bottom-emission structure.

[0376] Light from the light-emitting device is emitted towards the substrate 351. Preferably, a material with high transmittance for visible light is used for the substrate 351. In contrast, there is no restriction regarding the light transmittance of a material used for the substrate 352.

[0377] The opaque layer 157 is preferably formed between the substrate 351 and the transistor 201 and between the substrate 351 and the transistor 205. Fig. Figure 9 provides an example in which the opaque layer 157 is provided over the substrate 351, an insulating layer 153 is provided over the opaque layer 157, and the transistors 201 and 205 and the like are provided over the insulating layer 153.

[0378] The light-emitting device 130R comprises a conductive layer 112R, a conductive layer 126R above the conductive layer 112R and a conductive layer 129R above the conductive layer 126R.

[0379] The light-emitting device 130B comprises a conductive layer 112B, a conductive layer 126B above the conductive layer 112B and a conductive layer 129B above the conductive layer 126B.

[0380] A material with high transmittance for visible light is used for each of the conductive layers 112R, 112B, 126R, 126B, 129R and 129B. A material that reflects visible light is preferably used for the common electrode 155.

[0381] Although in Fig. Not shown in Figure 9, the light-emitting device 130G is also provided.

[0382] Although Fig. As 9 and the like provide an example in which the top of layer 128 includes a flat section, the shape of layer 128 is not particularly restricted. [Display device 600D]

[0383] The 600D display device with a bottom-emission structure, which is in Fig. Figure 10A is an example of a bottom-emission indicator device, which differs from the indicator device 600C shown in Figure 600C. Fig. 9 is shown. The display device 600D differs from the display device 600C in that it includes an organic resin layer 180. It should be noted that in the drawings reference numerals of some of the components that are shown in Fig. 9 are shown, omitted, for details of the components reference can be made to the description which is based on Fig. 9 has been carried out.

[0384] Fig. Figure 10B shows a top-down layout of pixel 178 (one pixel 178a and one pixel 178b), each comprising subpixel 110 (subpixels 110R, 110G, 110B and 110W), and Fig. Figure 10C shows a top view of the organic resin layer 180 in an area where subpixels 110R and 110W of pixel 178 are formed. A region of subpixel 110R between the opaque layers 317 can be represented as width 110Rw in a light-emitting region.

[0385] As in Fig. As shown in Figure 10A, the organic resin layer 180 is provided over the insulating layer 214. As shown in Fig. 10C and the area in Fig. As shown in Figure 10A, which is enclosed by the dashed line, the organic resin layer 180 includes a recessed section 181 (recessed sections 181a and 181b) having a curved surface, at least in one region where the subpixel is formed. It should be noted that the recessed section 181 can be provided outside the light-emitting region, such as a recessed section 181c. With recessed section 181c, light emission generated in a region overlapping with the opaque layer 317, or light propagating towards the region overlapping with the opaque layer 317, can be refracted and extracted from the light-emitting region, thereby improving the emission efficiency.

[0386] A multitude of recessed sections 181 can be formed in a matrix. The recessed sections 181a and 181b can be provided in contact with each other or can be provided such that they have a flat surface between them.

[0387] Although in Fig. 10A and Fig. 10C the top surface shape and the cross-sectional shape of the recessed section hexagonal ( Fig. 10C) or semicircular ( Fig. 10A), other shapes may be used as needed. Examples of a top-view shape of the recessed section include polygons, such as a triangle, a quadrilateral (including a rectangle and a square), and a pentagon, these polygons with rounded corners, an ellipse, and a circle.

[0388] An insulating layer containing an organic material can be used as an organic resin layer 180. Examples of materials used for the organic resin layer 180 include an acrylic resin, a polyimide resin, an epoxy resin, an imide resin, a polyamide resin, a polyimidamide resin, a silicone resin, a siloxane resin, a benzocyclobutene-based resin, a phenolic resin, and precursors of these resins. The organic resin layer 180 can be formed using an organic material such as polyvinyl alcohol (PVA), polyvinyl butyral, polyvinylpyrrolidone, polyethylene glycol, polyglycerin, pullulan, water-soluble cellulose, or an alcohol-soluble polyamide resin.

[0389] A photosensitive resin can also be used for the organic resin layer 180. A photoresist can be used for the photosensitive resin. Either a positive or a negative photosensitive material can be used as the photosensitive resin.

[0390] The organic resin layer 180 can contain a material that absorbs visible light. For example, the organic resin layer 180 itself can be formed from a material that absorbs visible light, or the organic resin layer 180 can contain a pigment that absorbs visible light. For example, the organic resin layer 180 can be formed using a resin that can be used as a color filter, transmitting red, blue, or green light and absorbing light of the other colors, or a resin that contains carbon black as a pigment and serves as a black matrix.

[0391] The first electrode 101 (the first electrode 101R and a first electrode 101W) lies above the organic resin layer 180, and the organic compound layer 103 lies above the first electrode 101. End sections of the first electrodes 101 and the organic compound layer 103 can be covered with the insulating layer 127.

[0392] The first electrode 101, which forms over the organic resin layer 180, also has a recessed section along the recessed section of the organic resin layer 180. The organic compound layer 103, which forms over the first electrode 101, also has a recessed section along the recessed section of the first electrode 101. The common layer 104, which forms over the organic compound layer 103, also has a recessed section along the recessed section of the organic compound layer 103. The common electrode 155, which forms over the common layer 104, also has a recessed section along the recessed section of the common layer 104.This means that the recessed sections of the organic resin layer 180, the first electrode 101, the organic compound layer 103, the common layer 104 and the common electrode 155 overlap with each other.

[0393] The common layer 104 lies above the organic compound layer 103 and the insulating layer 127, and the common electrode 155 lies above the common layer 104. The protective layer 135 is provided above the common electrode 155, and the substrate 352 is bonded using the adhesive layer 142.

[0394] Although in Fig. Not shown in 10A, the light-emitting devices 130G and 130B are also provided. [Display device 600E]

[0395] The in Fig. The display device 600E shown in Figure 11A is a modification example of the one described in Figure 11A. Fig. 8A shows the top emission display device 600B and differs from the display device 600B mainly in that it includes the color layers 136R, 136G and 136B.

[0396] In the display device 600E, the light-emitting device 130 comprises an area that overlaps with one of the color layers 136R, 136G, and 136B. The color layers 136R, 136G, and 136B can be provided on the surface of the substrate 352 on the side of the substrate 351. End sections of the color layers 136R, 136G, and 136B can overlap with the opaque layer 157.

[0397] In the display device 600E, the light-emitting device 130 can, for example, emit white light. For example, the color layers 136R, 136G, and 136B can transmit red, green, and blue light, respectively. It should be noted that in the display device 600E, the color layers 136R, 136G, and 136B can be provided between the protective layer 135 and the adhesive layer 142.

[0398] Although Fig. 8A, Fig. As 11A and the like each represent an example in which the top of layer 128 includes a flat section, the shape of layer 128 is not particularly restricted. Fig. 11B to Fig. Figure 11D shows modification examples of layer 128.

[0399] As in Fig. 11B and Fig. As shown in Figure 11D, the top surface of layer 128 can have a shape such that, in a cross-sectional view, its center and surrounding area are recessed (i.e., a shape with a concave surface). A common layer 154 can be provided such that it is in contact with the common electrode 155.

[0400] As in Fig. As shown in Figure 11C, the top of layer 128 can have a shape in which, in a cross-sectional view, its center and its surroundings bulge, i.e., a shape with a convex surface.

[0401] The top surface of layer 128 can have a convex surface and / or a concave surface. The number of convex surfaces and the number of concave surfaces contained in the top surface of layer 128 are unlimited and can each be one, two, or more.

[0402] The top height of layer 128 and the top height of conductive layer 224R can be the same or substantially the same, or they can differ. For example, the top height of layer 128 can be lower or higher than the top height of conductive layer 224R.

[0403] In the Fig. In the example shown in Figure 11B, it can be said that layer 128 is fitted into the recessed section of the conductive layer 224R. In contrast, as shown in Fig. Figure 11D shows that layer 128 also exists outside the recessed section of the conductive layer 224R, i.e., that the top of layer 128 can extend over the recessed section. [Display device 600F]

[0404] The in Fig. The display device 600F shown in Figure 12A is a modification example of the one described in Figure 12A. Fig. 8A to Fig. 8C shows the top-emission display device 600B, which includes microlenses 182 over the color layers 136R, 136G, and 136B. It should be noted that the reference numerals of the components that refer to those in Fig. 8A to Fig. 8C are the same, in some cases they may be omitted, and for details of such components refer to the description for Fig. 8A to Fig. 8C is referred to.

[0405] Fig. Figure 12B shows a top-down layout of pixel 178 (pixels 178a and 178b), each comprising subpixels 110 (subpixels 110R, 110G and 110B), and Fig. Figure 12C shows a top view of the microlenses 182 in an area where subpixels 110R, 110G, and 110B of pixel 178 are formed. It should be noted that the width of the area where the common electrode 155 and the organic compound layer 103 are in contact corresponds to a width of 110Gw in the light-emitting region of subpixel 110G.

[0406] At the in Fig. 12A to Fig. In the display device 600F shown in Figure 12C, a planarizing film 143 is provided over the protective layer 135, and the color layers 136R, 136G, and 136B are provided over a planarizing film 144. The planarizing film 144 is provided to cover the color layers 136R, 136G, and 136B. The microlenses 182 are provided over the planarizing film 144.

[0407] It should be noted that, as in Fig. Figure 12C shows that the microlens 182 is preferably provided for each of the subpixels in an area in which the subpixel is formed.

[0408] Although the top surface shape of the microlens 182 in Fig. While Figure 12C shows a hexagon, other shapes can be used as needed. Examples of the top-view shape of the microlens 182 include polygons such as a triangle, a quadrilateral (including a rectangle and a square), and a pentagon, these polygons with rounded corners, an ellipse, and a circle.

[0409] The microlens 182 can be formed using a material similar to that of the organic resin layer 180.

[0410] This embodiment can be suitably combined with the other embodiments or examples. In this description, where a multitude of structural examples are shown for one embodiment, the structural examples can be combined as needed. (Version 6)

[0411] In this embodiment, electronic devices of embodiments of the present invention are described.

[0412] Electronic devices of this embodiment include the display device of an embodiment of the present invention in their display sections. The display device of an embodiment of the present invention is very reliable, and its resolution and definition can be easily increased. Therefore, the display device of an embodiment of the present invention can be used for display sections of various electronic devices.

[0413] Examples of electronic devices include, in addition to electronic devices with a relatively large screen, such as a television, a desktop or notebook PC, a computer monitor and the like, digital signage and a large gaming machine, such as a pinball machine, a digital camera, a digital video camera, a digital photo frame, a mobile phone, a portable gaming console, a portable information terminal and an audio playback device.

[0414] In particular, the display device of an embodiment of the present invention can have a high resolution and can therefore be advantageously used for an electronic device with a relatively small display area. Examples of such an electronic device include information terminals in the form of a wristwatch and a bracelet (wearable devices) and wearable devices that can be worn on the head, such as a VR device, a head-mounted display, a glasses-like AR device, and an MR device.

[0415] The resolution of the display device in an embodiment of the present invention is preferably as high as HD (number of pixels: 1280 × 720), FHD (number of pixels: 1920 × 1080), WQHD (number of pixels: 2560 × 1440), WQXGA (number of pixels: 2560 × 1600), 4K (number of pixels: 3840 × 2160) or 8K (number of pixels: 7680 × 4320). In particular, a resolution of 4K, 8K or higher is preferred. The pixel density (resolution) of the display device of an embodiment of the present invention is preferably higher than or equal to 100 ppi, more preferably higher than or equal to 300 ppi, even more preferably higher than or equal to 500 ppi, even more preferably higher than or equal to 1000 ppi, even more preferably higher than or equal to 2000 ppi, even more preferably higher than or equal to 3000 ppi, even more preferably higher than or equal to 5000 ppi, even more preferably higher than or equal to 7000 ppi.With such a high-definition and / or high-resolution display device, the electronic device can provide a more realistic impression, depth perception, and the like. There is no particular limitation regarding the screen ratio (aspect ratio) of the display device in an embodiment of the present invention. For example, the display device is compatible with various screen ratios, such as 1:1 (one square), 4:3, 16:9, and 16:10.

[0416] The electronic device in this embodiment may include a sensor (a sensor with a function for measuring force, displacement, position, speed, acceleration, angular velocity, rotational speed, distance, light, liquid, magnetism, temperature, a chemical substance, sound, time, hardness, electric field, current, voltage, electrical power, radiation, flow rate, humidity, gradient, vibration, an odor, or infrared rays).

[0417] The electronic device in this embodiment can have various functions. For example, the electronic device in this embodiment can have a function for displaying various information (e.g., a still image, a moving image, and a text image) on the display section, a touchscreen function, a function for displaying a calendar, the date, the time, and the like, a function for executing various types of software (programs), a wireless communication function, and a function for reading a program or data that is / are stored in a storage medium.

[0418] Examples of a portable device that can be worn on the head are given based on: Fig. 13A to Fig. 13D described. These wearable devices have at least one function for displaying AR content, one function for displaying VR content, one function for displaying SR content, and one function for displaying MR content. The electronic device with a function for displaying content of at least one of AR, VR, SR, MR, and the like enables the user to experience a higher level of immersion.

[0419] One in Fig. 13A shown electronic device 700A and one in Fig. The electronic device 700B shown in Figure 13B comprises a pair of display screens 751, a pair of housings 721, a communication section (not shown), a pair of carrying sections 723, a control section (not shown), an imaging section (not shown), a pair of optical components 753, a frame 757 and a pair of nose pads 758.

[0420] The display device of an embodiment of the present invention can be used for the display screens 751. Therefore, a very reliable electronic device is obtained.

[0421] The electronic devices 700A and 700B can each project images displayed on the display screens 751 onto display areas 756 of the optical components 753. Since the optical components 753 have a light-transmitting property, the user can see images displayed on the display areas that superimpose transmission images viewed through the optical components 753. Consequently, the electronic devices 700A and 700B are electronic devices capable of performing AR display.

[0422] In electronic devices 700A and 700B, a camera suitable for forward imaging can be provided as an imaging section. Furthermore, if electronic devices 700A and 700B are provided with an accelerometer, such as a gyroscope sensor, the orientation of the user's head can be detected, and an image corresponding to this orientation can be displayed on the display areas 756.

[0423] The communication section includes a wireless communication device, and a video signal can, for example, be supplied via the wireless communication device. Alternatively, or in addition to the wireless communication device, a connecting element can be provided, which may be connected to a cable for supplying a video signal and a power supply.

[0424] The electronic devices 700A and 700B are supplied with a battery, allowing them to be charged wirelessly and / or via cable.

[0425] A touch sensor module can be provided in the 721 enclosure. The touch sensor module has a function for detecting touch on the exterior of the 721 enclosure. By detecting a tap, slide, or similar action from the user with the touch sensor module, various types of processing are enabled. For example, a moving image can be paused or resumed by tapping, and it can be fast-forwarded or rewound by sliding. If the touch sensor module is provided in each of the two 721 enclosures, the operating possibilities can be expanded.

[0426] Various touch sensors can be applied to the touch sensor module. For example, any of the following types of touch sensors can be used: a capacitive type, a resistive type, an infrared type, an electromagnetic induction type, a surface acoustic wave type, and an optical type. In particular, a capacitive sensor or an optical sensor is preferably used for the touch sensor module.

[0427] In the case where an optical touch sensor is used, a photoelectric conversion device (also called a photoelectric conversion element) can be used as the light-receiving element. An inorganic semiconductor and / or an organic semiconductor can be used for an active layer of the photoelectric conversion device.

[0428] One in Fig. 13C shown electronic device 800A and one in Fig. The electronic device 800B shown in 13D comprises a pair of display sections 820, a housing 821, a communication section 822, a pair of support sections 823, a control section 824, a pair of imaging sections 825 and a pair of lenses 832.

[0429] The display device of an embodiment of the present invention can be used in the display sections 820. Therefore, a very reliable electronic device is obtained.

[0430] The display sections 820 are positioned within the housing 821 such that they are seen through the lenses 832. If the pair of display sections 820 shows different images, a three-dimensional display can be achieved using parallax.

[0431] The electronic devices 800A and 800B can be considered electronic devices for VR. The user wearing the electronic device 800A or 800B can see images displayed on the display sections 820 through the lenses 832.

[0432] The electronic devices 800A and 800B preferably include a mechanism for adjusting the lateral positions of the lenses 832 and the display sections 820, such that the lenses 832 and the display sections 820 are optimally positioned according to the positions of the user's eyes. Furthermore, the electronic devices 800A and 800B preferably include a mechanism for adjusting the focus by changing the distance between the lenses 832 and the display sections 820.

[0433] The electronic device 800A or the electronic device 800B can be mounted on the user's head using the supporting sections 823. For example, it shows Fig. Figure 13C provides an example in which the wearable section 823 has a shape such as a temple (also referred to as a connection or the like) of eyeglasses; however, an embodiment of the present invention is not limited to this. The wearable section 823 can have any shape that allows the user to wear the electronic device, e.g., the shape of a helmet or a band.

[0434] Imaging section 825 has a function for obtaining information about the external environment. Data obtained by imaging section 825 can be output to display section 820. An image sensor can be used for imaging section 825. Furthermore, a variety of cameras can be provided to support a variety of fields of view, such as a telescopic field of view and a wide-angle field of view.

[0435] Although an example providing Figure Section 825 is described here, only a distance sensor (hereinafter also referred to as the sensing section) capable of measuring the distance between the user and an object needs to be provided. In other words, Figure Section 825 is an embodiment of the sensing section. For example, an image sensor or a distance image sensor, such as a LiDAR (light detection and ranging) sensor, can be used as the sensing section. By using images obtained by the camera and images contained by the distance image sensor, more information can be obtained, enabling gesture operation with greater accuracy.

[0436] The electronic device 800A may include a vibration mechanism that functions as a bone conduction earphone. For example, at least one of the display section 820, the housing 821, and the wearable section 823 may include the vibration mechanism. Therefore, the user can enjoy videos and sounds simply by wearing the electronic device 800A, without requiring an additional audio device such as headphones, earphones, or a speaker.

[0437] The electronic devices 800A and 800B may each include an input port. A cable may be connected to the input port for supplying a video signal from a video output device or the like, for supplying power to charge a battery provided in the electronic device, and the like.

[0438] The electronic device of an embodiment of the present invention can have a function for performing wireless communication with earphones 750. The earphones 750 comprise a communication section (not shown) and have a wireless communication function. The earphones 750 can receive information (e.g., audio data) from the electronic device using the wireless communication function. For example, the electronic device 700A in Fig. 13A has a function for transmitting information to the 750 earphones with the wireless communication function. As a further example, the electronic device 800A features Fig. 13C includes a function for transmitting information to the 750 earbuds with the wireless communication function.

[0439] The electronic device may include an earphone section. The electronic device 700B in Fig. 13B includes earphone sections 727. For example, the earphone section 727 can be connected to the control section via a cable. Part of a cable connecting the earphone section 727 and the control section can be positioned inside the housing 721 or the wearable section 723.

[0440] Similarly, the electronic device 800B includes Fig. 13D Earpiece sections 827. For example, the earpiece section 827 can be connected to the control section 824 via a line. Part of a line connecting the earpiece section 827 and the control section 824 can be positioned inside the housing 821 or the wearable section 823. Alternatively, the earpiece sections 827 and the wearable sections 823 can include magnets. This is preferred because the earpiece sections 827 can be attached to the wearable sections 823 by a magnetic force and can therefore be easily stored.

[0441] The electronic device may include an audio output port to which earphones, headphones, or the like can be connected. The electronic device may also include an audio input port and / or an audio input mechanism. For example, an audio input mechanism could be a sound-collecting device such as a microphone. The electronic device may function as a headset by including the audio input mechanism.

[0442] As described above, both the spectacle-like device (e.g., the electronic devices 700A and 700B) and the safety-spectacle-like device (e.g., the electronic devices 800A and 800B) are preferable as electronic devices in an embodiment of the present invention.

[0443] The electronic device of an embodiment of the present invention can transmit information to the earphones via a wired or wireless connection.

[0444] One in Fig. 14A shown electronic device 6500 is a portable information terminal that can be used as a smartphone.

[0445] The electronic device 6500 comprises a housing 6501, a display section 6502, a power button 6503, buttons 6504, a speaker 6505, a microphone 6506, a camera 6507, a light source 6508, and the like. The display section 6502 has a touchscreen function.

[0446] The display device of an embodiment of the present invention can be used in the display section 6502. Therefore, a very reliable electronic device is obtained.

[0447] Fig. Figure 14B is a schematic cross-sectional view that includes an end section of the housing 6501 that is closer to the microphone 6506.

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

[0449] The display panel 6511, the optical component 6512 and the touch sensor panel 6513 are attached to the protective component 6510 by a bonding layer (not shown).

[0450] Part of the display panel 6511 is folded back in an area outside the display section 6502, and an FPC 6515 is connected to the folded-back part. An IC 6516 is mounted on the FPC 6515. The FPC 6515 is connected to a terminal provided on the printed circuit board 6517.

[0451] The display device of an embodiment of the present invention can be used in the display field 6511. Therefore, a very lightweight electronic device can be achieved. Since the display field 6511 is very thin, the high-capacity battery 6518 can be mounted without increasing the thickness of the electronic device. Furthermore, a portion of the display field 6511 is folded back, providing a connection section with the FPC 6515 on the rear of the pixel section, thus enabling the creation of an electronic device with a narrow bezel.

[0452] Fig. Figure 14C represents an example of a television set. In a television set 7100, a display section 7000 is installed in a housing 7171. Here, the housing 7171 is supported by a stand 7173.

[0453] The display device of an embodiment of the present invention can be used in the display section 7000. Therefore, a very reliable electronic device is obtained.

[0454] A service of the in Fig. The operation of the television set 7100 shown in Figure 14C can be carried out using an operating switch provided in the housing 7171 and a separate remote control 7151. Alternatively, the display section 7000 can include a touch sensor, and the television set 7100 can be operated by touching the display section 7000 with a finger or the like. The remote control 7151 can be provided with a display section for showing information output by the remote control 7151. The television channels and volume can be controlled by operating buttons or a touchscreen on the remote control 7151, and a video displayed on the display section 7000 can be controlled.

[0455] It should be noted that the 7100 television set includes a receiver, a modem, and similar components. The receiver allows for the reception of general television broadcasts. When the television set is connected to a communication network via the modem, either wirelessly or via a fixed connection, one-way (from a sender to a receiver) or two-way (e.g., between a sender and a receiver or between receivers) information communication can take place.

[0456] Fig. Figure 14D represents an example of a laptop PC. A laptop PC 7200 comprises a case 7211, a keyboard 7212, a pointing device 7213, an external connection port 7214, and the like. The display section 7000 is built into the case 7211.

[0457] The display device of an embodiment of the present invention can be used in the display section 7000. Therefore, a very reliable electronic device is obtained.

[0458] Fig. 14E and Fig. 14F presents examples of digital signage that can be used for shop windows, display cases and the like.

[0459] One in Fig. The Digital Signage 7300 shown in Figure 14E comprises a housing 7301, the display section 7000, a speaker 7303, and the like. The Digital Signage 7300 may also include an LED lamp, an operating button (including a power switch or an operating switch), a connection port, various sensors, a microphone, and the like.

[0460] Fig. 14F represents a Digital Signage 7400 mounted on a cylindrical column 7401. The Digital Signage 7400 includes the display section 7000, which is provided along a curved surface of the column 7401.

[0461] In Fig. 14E and Fig. 14F, the display device of an embodiment of the present invention can be used in the display section 7000. Therefore, a very reliable electronic device is obtained.

[0462] A larger area of ​​ad space 7000 can increase the amount of information that can be presented at once. The larger ad space 7000 attracts more attention, thus increasing the effectiveness of advertising, for example.

[0463] In particular, in the case where the display device of an embodiment of the present invention is used for the Digital Signage 7300 and the Digital Signage 7400, which are in Fig. 14E and Fig. 14F, which can be used to display advertisements and the like, the display device, which is a translucent panel, increases the flexibility of the display. A translucent display device can be manufactured, for example, by using a conductor and a carrier part, each formed from a conductive film that transmits visible light, and by regulating the distance between pixel electrodes.

[0464] By using the light-emitting tandem device of an embodiment of the present invention, in addition to the conductor and the carrier part, each formed from the conductive film that transmits visible light, the luminance per pixel can be increased. This means that an advantageous display can be achieved even if the aperture ratio of the display device is reduced; therefore, the light transmission property of the display section of the display device can be increased. Consequently, such a structure is suitably used in the translucent display device of an embodiment of the present invention.

[0465] As in Fig. 14E and Fig. As shown in Figure 14F, it is preferred that the Digital Signage 7300 or the Digital Signage 7400 can interact with an information terminal device 7311 or an information terminal device 7411, such as a smartphone owned by a user, via wireless communication. For example, information from an advertisement displayed on the display section 7000 can be displayed on a screen of the information terminal device 7311 or the information terminal device 7411. By operating the information terminal device 7311 or the information terminal device 7411, a displayed image on the display section 7000 can be switched.

[0466] It is possible to configure the Digital Signage 7300 or the Digital Signage 7400 to run a game using the screen of the Information Terminal 7311 or the Information Terminal 7411 as a controller. This allows an unlimited number of users to participate in and enjoy the game simultaneously.

[0467] The in Fig. 15A to Fig. The electronic devices shown in 15G include a housing 9000, a display section 9001, a loudspeaker 9003, an operating button 9005 (including a power switch or an operating switch), a connecting port 9006, a sensor 9007 (a sensor having a function to measure force, displacement, position, velocity, acceleration, angular velocity, rotational speed, distance, light, liquid, magnetism, temperature, a chemical substance, sound, time, hardness, electric field, current, voltage, electrical power, radiation, flow rate, humidity, gradient, oscillation, an odor or infrared rays), a microphone 9008 and the like.

[0468] The in Fig. 15A to Fig. The electronic devices depicted in Article 15G have various functions. For example, the electronic devices may have a function for displaying various types of information (e.g., a still image, a moving image, and a text image) on the display section, a touchscreen function, a function for displaying a calendar, date, time, and the like, a function for controlling processing using various types of software (programs), a wireless communication function, and a function for reading and processing a program or data stored on a storage medium. It should be noted that the functions of the electronic devices are not limited to these, and the electronic devices may have various functions. The electronic devices may include a variety of display sections.The electronic devices may each be equipped with a camera or the like and have a function for taking a still image or a moving image, a function for storing the recorded image in a storage medium (an external storage medium or a storage medium built into the camera), a function for displaying the recorded image on the display section, and the like.

[0469] The following are the electronic devices in Fig. 15A to Fig. 15G described in detail.

[0470] Fig. Figure 15A is a perspective view of a portable information terminal 9171. For example, the portable information terminal 9171 can be used as a smartphone. The portable information terminal 9171 may include the speaker 9003, the connection port 9006, the sensor 9007, or the like. The portable information terminal 9171 can display character and image information on its various surfaces. Fig. Figure 15A shows an example where three icons 9050 are displayed. Additionally, information 9051, represented by dashed rectangles, can be displayed on another surface of the display section 9001. Examples of information 9051 include notification of the arrival of an email, SNS message, call, or the like; the subject and sender of an email, SNS message, or the like; the date, time, remaining battery power, and radio wave intensity. Alternatively, the icon 9050, or the like, can be displayed in the location where the information 9051 is shown.

[0471] Fig. Figure 15B is a perspective view of a portable information terminal 9172. The portable information terminal 9172 has a function for displaying information on three or more surfaces of the display section 9001. In the example shown here, information 9052, information 9053, and information 9054 are displayed on different surfaces. For example, the user of the portable information terminal 9172 can check information 9053, which is displayed in such a way that it can be viewed from above the portable information terminal 9172, with the portable information terminal 9172 kept in a breast pocket of their clothing. Therefore, the user can see the display without removing the portable information terminal 9172 from the pocket and can, for example, decide whether to answer the call.

[0472] Fig. Figure 15C is a perspective view of a tablet terminal 9173. The tablet terminal 9173 is suitable, for example, for running various applications, such as making mobile phone calls, sending and receiving emails, viewing and editing texts, playing music, internet communication, and running computer games. The tablet terminal 9173 includes the display section 9001, the camera 9002, the microphone 9008, and the speaker 9003 on the front of the housing 9000; the control buttons 9005 on the left side of the housing 9000; and the connection port 9006 on the bottom of the housing 9000.

[0473] Fig. Figure 15D is a perspective view of a portable information terminal 9200 in the form of a wristwatch. The portable information terminal 9200 can be used, for example, as a smartwatch (registered trademark). The portable information terminal 9200 can include the operating button 9005 as a knob for operation on the left side of the case 9000 and the sensor 9007 on the underside of the case 9000. Although the case 9000, which has a curved wristband shape, is shown as an example, a belt or the like can be used in combination with the case 9000 to make the portable information terminal 9200 wearable. The display surface of the display section 9001 is curved, and an image can be displayed on the curved display surface. An energy storage device 9004 can have a curved shape along the case 9000.The energy storage device 9004 is flexible and can be bent to accommodate changes in shape when the user puts on or takes off the portable information terminal 9200. A charging control IC connected to the energy storage device 9004 can be provided. Furthermore, two-way communication between the portable information terminal 9200 and a headset suitable for wireless communication is possible, enabling hands-free telephone calls. The portable information terminal 9200 can wirelessly transmit data to another information terminal and can be charged wirelessly. The connection port 9006 can be provided in the housing 9000, allowing for wired data transmission and charging.

[0474] Fig. 15E to Fig. 15G are perspective views of a foldable portable information terminal 9201. Fig. Figure 15E is a perspective view showing the Portable Information Terminal 9201 open. Fig. 15G is a perspective view showing the Portable Information Terminal 9201 folded. Fig. Figure 15F is a perspective view depicting the portable information terminal 9201, which is in one of the states in Fig. 15E and Fig. 15G is shifted into the other. When the portable information terminal 9201 is opened, a seamless, large display area is easily searchable. The display section 9001 of the portable information terminal 9201 is supported by three housings 9000 connected to each other by hinges 9055. For example, the display section 9001 can be folded with a radius of curvature greater than or equal to 0.1 mm and less than or equal to 150 mm.

[0475] This embodiment can be suitably combined with the other embodiments or examples. In this description, where a multitude of structural examples are shown for one embodiment, the structural examples can be combined as needed. [Example 1]<<Synthesebeispiel 1> >

[0476] This synthesis example describes a method for synthesizing the organic compound of the present invention, represented by structural formula (100) in embodiment 1, namely N-[4-(1-naphthyl)phenyl]-N-(9,9'-spirobi[9H-fluorene]-2-yl)benzo[b]naphtho[2,1-d]furan-10-amine (abbreviation: SFNBaBnf(10)). The structure of SFNBaBnf(10) is shown below. <Synthese von SFNBaBnf(10)>

[0477] Into a 100 ml three-necked flask, 3.5 g (6.6 mmol) of N-[4-(1-naphthyl)phenyl]-N-(9,9'-spirobi[9H-fluorene]-2-amine and 2.0 g (6.7 mmol) of 10-bromobenzo[b]naphtho[2,1-d]furan were added. After the air in the flask had been replaced with nitrogen, 2.1 g (22 mmol) of sodium tert-butoxide (abbreviation: t BuONa) and 34 ml of toluene were added. This mixture was degassed by stirring under reduced pressure. The mixture was then heated to 60 °C. To this reaction solution, 0.40 ml (0.15 mmol) of tri-tert-butylphosphine (abbreviation: P( t Bu)3) (10 wt% hexane solution) and 41 mg (71 µmol) bis(dibenzylideneacetone)palladium(0) were added, and stirring was carried out for 4 hours at 120 °C. Toluene was added to this mixture, and the resulting mixture was subjected to suction filtration through aluminum oxide, Celite (FUJIFILM Wako Pure Chemical Corporation, catalog no. 537-02305), and Florisil (FUJIFILM Wako Pure Chemical Corporation, catalog no. 066-05265). The resulting filtrate was concentrated to obtain 5.8 g of a white solid containing the target compound. This solid was purified by high-performance liquid chromatography (HPLC) (mobile phase: chloroform) to obtain 5.2 g of a white solid containing the target compound. 3.1 g of the resulting white solid were purified by a train sublimation process.In the sublimation purification, the solid was heated for 24 hours at 310 °C under a pressure of 1.60 Pa. After sublimation purification, 2.1 g of a white target solid were obtained (yield: 43%, collection rate: 68%). The synthesis scheme (s-1) of SFNBaBnf(10) is shown below.

[0478] The results of a 1 H-NMR measurements of the obtained white solid are given below. Fig. 17 shows a 1 ¹H NMR spectrum. This shows that SFNBaBnf(10) was obtained in this synthesis example.

[0479] 1 H-NMR (dichloromethane-d2, 500 MHz): δ = 7.99-7.94 (m, 3H), 7.91-7.83 (m, 5H), 7.78 (d, J = 9.0 Hz, 1H), 7.71 (d, J = 7.5 Hz, 3H), 7.55-7.47 (m, 4H), 7.42-7.14 (br-m, 12H), 7.04 (br, 1H), 6.78 (t, J = 7.0 Hz, 2H), 6.69 (d, J = 7.5 Hz, 2H), 6.59 (br-d, J = 8.0 Hz, 2H).

[0480] The molecular weight of the obtained white solid was measured by LC / MS analysis. It should be noted that the LC / MS analysis involved liquid chromatography (LC) separation using UltiMate 3000, manufactured by Thermo Fisher Scientific KK, and mass spectrometry (MS) using Q Exactive, also manufactured by Thermo Fisher Scientific KK.

[0481] As a result, a signal at m / z of 749 was observed, while the mass of the target substance was calculated to be 749, revealing that SFNBaBnf(10) was obtained. <Messung von physikalischen Eigenschaften>

[0482] Next, the UV-VIS absorption spectra (hereinafter referred to simply as absorption spectra) and photoluminescence (PL) spectra (hereinafter referred to simply as emission spectra) of a toluene solution and a thin film of SFNBaBnf(10) were measured. The absorption spectrum was measured using a UV-VIS spectrophotometer (V-770DS, manufactured by JASCO Corporation). The emission spectrum was measured using a fluorescence spectrophotometer (FP-8600DS, JASCO Corporation).

[0483] To calculate the absorption spectrum of the toluene solution of SFNBaBnf(10), the absorption spectrum of toluene placed in a quartz cell was measured and then subtracted from the absorption spectrum of the toluene solution of SFNBaBnf(10) placed in a quartz cell.

[0484] To obtain the absorption and emission spectra of the thin film, a test sample was measured. The test sample was prepared as follows: SFNBaBnf(10) was formed over a quartz substrate by vacuum evaporation and sealed using another quartz substrate as a counter-substrate. It should be noted that the emission spectrum was obtained by measuring the sealed sample, and the absorption spectrum was obtained by measuring the sample after the seal was removed and the counter-substrate was extracted. The absorption spectrum was obtained by subtracting the absorption spectrum of the quartz substrate from the absorption spectrum of SFNBaBnf(10) formed over the quartz substrate.

[0485] Fig. 18 and Fig. Figure 19 shows the measurement results for the toluene solution and the thin film, respectively. According to the measurements, the toluene solution of SFNBaBnf(10) exhibits an absorption peak at approximately 357 nm, the thin film of SFNBaBnf(10) exhibits an absorption peak at approximately 362 nm...

Claims

[1] Organic compound represented by the general formula (G1), where: α 1 represents a substituted or unsubstituted phenylene group; n 1 or 2 is; α 2 represents a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group; m 0, 1 or 2 is; R 1 to R 7 each independently represent hydrogen, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, or a substituted or unsubstituted phenyl group; Ar 2 represents a group that is defined by the general formula (Ar 2 -a) or the general formula (Ar 2 -b) is represented; one of R 8 to R 17represents a bond; other R 8 until \R 17 as the bond as well as R 18 to R 28 and R 31 to R 34 each independently represent hydrogen, a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a silyl group with 3 to 18 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms; and X represents oxygen or sulfur. [2] Organic compound according to claim 1, where the organic compound is represented by the general formula (G2), and where R 1 to R 7 and R 35 to R 38 Each can independently represent hydrogen, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms. [3] Organic compound according to claim 2, wherein m in the general formula (G2) is 0. [4] Organic compound according to claim 1, wherein the organic compound is represented by the general formula (G4), and where: R 35 to R 38 each independently represent hydrogen, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms; and R 9 to R17 , R 18 to R 28 and R 31 to R 34 Each can independently represent hydrogen, a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a silyl group with 3 to 18 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms. [5] Organic compound according to claim 1, wherein the organic compound is represented by the general formula (G5), and where: R 35 to R 38each independently represent hydrogen, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms; and R 9 to R 17 , R 18 to R 28 and R 31 to R 34Each can independently represent hydrogen, a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a silyl group with 3 to 18 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms. [6] Organic compound according to claim 1, wherein the organic compound is represented by the structural formula (100) or the structural formula (101), [7] Organic semiconductor device comprising: the organic compound according to claim 1. [8] Light-emitting device comprising: the organic compound according to claim 1. [9] Organic compound represented by the general formula (G7), where: α 2 represents a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group; m 0, 1 or 2 is; R 1 to R 7 and R 35 to R 38 each independently represent hydrogen, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms; Ar 2 represents a group that is defined by the general formula (Ar 2 -b) is represented; one of R 8 to R 17 represents a bond; other R 8 to R 17as the bond as well as R 18 to R 34 each independently represent hydrogen, a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a silyl group with 3 to 18 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms; and X represents oxygen or sulfur. [10] Organic compound according to claim 9, wherein m is 0. [11] Organic semiconductor device comprising: the organic compound according to claim 9. [12] Light-emitting device comprising: the organic compound according to claim 9. [13] Light-emitting device comprising: a first electrode; a second electrode; a light-emitting layer; and a first layer, where the light-emitting layer lies between the first electrode and the second electrode, wherein the first layer lies between the first electrode and the light-emitting layer, wherein the first layer comprises an organic compound represented by the general formula (G8), and where: α 1 and α 2 each independently represents a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene-diyl group; n 1 or 2 is; m 0, 1 or 2 is; R 1 to R 7each independently represent hydrogen, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, or a substituted or unsubstituted phenyl group; Ar 2 a substituted or unsubstituted benzo[b]naphtho[2,1-d]furanyl group, a substituted or unsubstituted benzo[b]naphtho[2,3-d]furanyl group, a substituted or unsubstituted benzo[b]naphtho[2,1-d]thiophenyl group, or a substituted or unsubstituted benzo[b]naphtho[2,3-d]thiophenyl group; and Ar 3 represents a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted spirobifluorenyl group. [14] Light-emitting device according to claim 13, where the organic compound in the first layer is represented by the general formula (G9), and where: Ar 2 represents a group that is defined by the general formula (Ar 2 -a) or the general formula (Ar 2 -b) is represented; one of R 8 until \R 17 represents a bond; other R 8 until \R 17 as the bond as well as R 18 to R 28 and R 31 to R 34each independently represents hydrogen, a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a silyl group with 3 to 18 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms; if R 29 and R 30 each represent a bond, R 29 and R 30 are tied together to form a ring; if neither R 29 still R 30 represents a bond, R 29 and R 30each independently represent hydrogen, a halogen, a cyano group, a straight-chain or branched-chain alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a silyl group with 3 to 18 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms; and X represents oxygen or sulfur. [15] Light-emitting device according to claim 13, wherein the first layer is in contact with the light-emitting layer. [16] Light-emitting device according to claim 13, where the first layer is in contact with the light-emitting layer, wherein the light-emitting layer comprises a first host material, a second host material and a light-emitting substance, wherein the first host material and the second host material combine to form an exciplex, and where the difference between a peak wavelength of an emission spectrum of the exciplex and a peak wavelength of an emission spectrum of the light-emitting substance is less than or equal to 30 nm. [17] Light-emitting device according to claim 13, wherein the first layer is in contact with the light-emitting layer, and wherein the light-emitting layer comprises a host material and a fluorescent substance.

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