Organic Compounds and Light-Emitting Devices

Abstract

To provide a novel organic compound which is very convenient, useful or reliable.SOLUTION: The organic compound is represented by the general formula (G1) in the figure, where at least one of R1 to R26 is deuterium and the others are each hydrogen, an alkyl group, a cycloalkyl group, a trialkylsilyl group, an aryl group, or the like.SELECTED DRAWING: None

Description

[Technical Field]

[0001] One aspect of the present invention relates to an organic compound, a light-emitting device, a display device, an electronic device, a light-emitting apparatus, a lighting apparatus, or a semiconductor device.

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

[0003] The practical application of light-emitting devices (organic EL elements) that utilize electroluminescence (EL) using organic compounds is progressing. The basic structure of these light-emitting devices is an organic compound layer (EL layer) containing a light-emitting material sandwiched between a pair of electrodes. By applying a voltage to this element, carriers are injected, and by utilizing the recombination energy of these carriers, light emission can be obtained from the light-emitting material.

[0004] Because these light-emitting devices are self-illuminating, they offer higher visibility compared to liquid crystal displays and are therefore suitable as display pixels. Furthermore, displays using such light-emitting devices do not require a backlight, allowing for thin and lightweight designs, which is a significant advantage. Another characteristic is their extremely fast response time.

[0005] Furthermore, since these light-emitting devices can form a light-emitting layer continuously in two dimensions, they can produce light in a planar manner. This is a feature that is difficult to obtain with point light sources such as incandescent bulbs or LEDs, or line light sources such as fluorescent lamps, and therefore has high value as a planar light source that can be applied to lighting and other applications.

[0006] While displays or lighting devices using light-emitting devices are suitable for various electronic devices, research and development are underway to find light-emitting devices with better efficiency and lifespan.

[0007] While the characteristics of light-emitting devices have improved remarkably, they are still insufficient to meet the high demands for all characteristics, including efficiency and durability. In particular, to solve problems such as burn-in, which are still a concern for EL devices, it is advantageous to minimize the decrease in efficiency due to degradation.

[0008] Degradation is largely determined by the luminescent central material and the surrounding materials; therefore, there is active research being done to develop host materials with favorable properties. [Prior art documents] [Patent Documents]

[0009] [Patent Document 1] International Open Brochure WO2020 / 165694 [Overview of the project] [Problems that the invention aims to solve]

[0010] One aspect of the present invention aims to provide a novel organic compound that is excellent in convenience, usefulness, or reliability. Alternatively, it aims to provide a novel light-emitting device that is excellent in convenience, usefulness, or reliability. Alternatively, it aims to provide a novel display device that is excellent in convenience, usefulness, or reliability. Alternatively, it aims to provide a novel electronic device that is excellent in convenience, usefulness, or reliability. Alternatively, it aims to provide a novel light-emitting device that is excellent in convenience, usefulness, or reliability. Alternatively, it aims to provide a novel lighting device that is excellent in convenience, usefulness, or reliability. Alternatively, it aims to provide a novel organic compound, a novel light-emitting device, a novel display device, a novel electronic device, a novel light-emitting device, a novel lighting device, or a novel semiconductor device.

[0011] Furthermore, the description of these problems does not preclude the existence of other problems. Moreover, one aspect of the present invention does not need to solve all of these problems. Other problems will naturally become apparent from the description in the specification, drawings, and claims, and it is possible to extract other problems from the description in the specification, drawings, and claims. [Means for solving the problem]

[0012] (1) One aspect of the present invention is an organic compound represented by the following general formula (G1).

[0013] [ka]

[0014] However, R 1 ~R 26 At least one of them is deuterium.

[0015] Also, R 1 ~R 7At least one of them is any one of a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted trialkylsilyl group or a substituted or unsubstituted aryl group, and R 1 to R 7 are each independently any one of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted trialkylsilyl group or a substituted or unsubstituted aryl group. In the present specification, hydrogen includes deuterium.

[0016] Also, R 8 to R 26 are each independently any one of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted trialkylsilyl group or a substituted or unsubstituted aryl group. When it is an alkyl group, the number of carbon atoms is 3 or more and 10 or less, when it is a cycloalkyl group, the number of carbon atoms is 3 or more and 10 or less, when it is a trialkylsilyl group, the number of carbon atoms is 3 or more and 12 or less, and when it is an aryl group, the number of carbon atoms is 6 or more and 25 or less.

[0017] (2) Also, one aspect of the present invention is an organic compound represented by the following general formula (G1).

[0018]

Chemical formula

[0019] However, R 1 to R 7 are hydrogen.

[0020] Also, at least one of R 20 to R 26 is deuterium, and the others of R 20 to R 26 and R 8 to R 19Each of these is independently one of the following: hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted trialkylsilyl group, or a substituted or unsubstituted aryl group. If it is an alkyl group, it has 3 to 10 carbon atoms; if it is a cycloalkyl group, it has 3 to 10 carbon atoms; if it is a trialkylsilyl group, it has 3 to 12 carbon atoms; and if it is an aryl group, it has 6 to 25 carbon atoms.

[0021] (3) Another aspect of the present invention is an organic compound represented by the following general formula (G2).

[0022] [ka]

[0023] However, R 1 ~R 7 Each of these is independently either a hydrogen atom or a substituted or unsubstituted aryl group.

[0024] Also, R 8 ~R 19 Each of these is independently one of the following: hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted trialkylsilyl group, or a substituted or unsubstituted aryl group. If it is an alkyl group, it has 3 to 10 carbon atoms; if it is a cycloalkyl group, it has 3 to 10 carbon atoms; if it is a trialkylsilyl group, it has 3 to 12 carbon atoms; and if it is an aryl group, it has 6 to 25 carbon atoms. D represents deuterium.

[0025] (4) Another aspect of the present invention is an organic compound represented by the following general formula (G2).

[0026] [ka]

[0027] However, R1 ~R 7 Each of these is independently a hydrogen atom or a substituted or unsubstituted aryl group, and the aryl group has between 6 and 25 carbon atoms.

[0028] Also, R 8 ~R 19 It is hydrogen.

[0029] This allows for the increased bond dissociation energy of a compound by utilizing carbon-deuterium bonds, which have a higher bond dissociation energy than carbon-hydrogen bonds. Furthermore, it can suppress bond dissociation within the compound structure in the excited state. It can also suppress the degradation or alteration of the compound due to the dissociation of carbon-deuterium bonds. Additionally, it can suppress the formation of degradation products. For example, it can be suitably used in the light-emitting layer of a light-emitting device. It can also be suitably used in a layer in contact with the light-emitting layer of a light-emitting device. In this way, it is possible to provide a novel organic compound with excellent convenience, usefulness, and reliability.

[0030] (5) Another aspect of the present invention is a light-emitting device having a first electrode, a second electrode, and a unit.

[0031] The unit is sandwiched between a first electrode and a second electrode, and the unit contains a luminescent organic compound and the aforementioned organic compound.

[0032] This allows for increased bond dissociation energy of compounds by utilizing carbon-deuterium bonds, which have a higher bond dissociation energy than carbon-hydrogen bonds. Furthermore, it can suppress bond dissociation within the compound structure in the excited state. It can also suppress degradation or alteration of compounds due to carbon-deuterium bond dissociation. Additionally, it can suppress the formation of degradation products. Furthermore, it can suppress the decrease in luminescence efficiency due to degradation products. This also allows for the provision of light-emitting devices with high luminescence efficiency, a good operating life, and reduced changes in emission color during operation. Finally, it allows for the provision of light-emitting devices with high color purity. As a result, it is possible to provide novel light-emitting devices with superior convenience, usefulness, and reliability.

[0033] (6) Another aspect of the present invention is a light-emitting device having a first electrode, a second electrode, and a unit.

[0034] The unit is sandwiched between a first electrode and a second electrode, and the unit comprises a first layer, a second layer, and a third layer.

[0035] The first layer is sandwiched between the second and third layers, and the third layer is sandwiched between the second electrode and the first layer.

[0036] The second layer is sandwiched between the first layer and the first electrode, and the second layer contains a hole-transporting material.

[0037] The first layer contains a luminescent organic compound and the above-mentioned organic compound.

[0038] (7) Another aspect of the present invention is a light-emitting device having a first electrode, a second electrode, and a unit.

[0039] The unit is sandwiched between a first electrode and a second electrode, and the unit comprises a first layer, a second layer, and a third layer.

[0040] The first layer is sandwiched between the second and third layers, and the third layer is sandwiched between the second electrode and the first layer.

[0041] The second layer is sandwiched between the first layer and the first electrode, the second layer comprising a hole-transporting material, and the first layer comprising a luminescent organic compound.

[0042] The third layer contains the above-mentioned organic compound.

[0043] (8) Another aspect of the present invention is the above-mentioned light-emitting device in which a luminescent organic compound EM emits blue fluorescence.

[0044] (9) Another aspect of the present invention is a display device having the above-mentioned light-emitting device and a transistor or substrate.

[0045] (10) Another aspect of the present invention is an electronic device having the above-mentioned display device, a sensor, an operation button, a speaker or a microphone.

[0046] (11) Another aspect of the present invention is a light-emitting device having the above-mentioned light-emitting device and a transistor or substrate.

[0047] (12) Another aspect of the present invention is a lighting device having the above-mentioned light-emitting device and a housing.

[0048] In the drawings attached to this specification, components are classified by function and shown as independent blocks in block diagrams. However, in reality, it is difficult to completely separate components by function, and a single component may be involved in multiple functions.

[0049] In this specification, the term "light-emitting device" includes image display devices using light-emitting elements. Furthermore, modules in which a connector, such as an anisotropic conductive film or TCP (Tape Carrier Package), is attached to a light-emitting element, modules in which a printed circuit board is provided at the end of the TCP, or modules in which an IC (integrated circuit) is directly mounted to a light-emitting element using the COG (Chip On Glass) method may also be included as light-emitting devices. Additionally, lighting fixtures and the like may have light-emitting devices. [Effects of the Invention]

[0050] According to one aspect of the present invention, it is possible to provide a novel organic compound that is excellent in convenience, usefulness, or reliability. Alternatively, it is possible to provide a novel light-emitting device that is excellent in convenience, usefulness, or reliability. Alternatively, it is possible to provide a novel display device that is excellent in convenience, usefulness, or reliability. Alternatively, it is possible to provide a novel electronic device that is excellent in convenience, usefulness, or reliability. Alternatively, it is possible to provide a novel light-emitting device that is excellent in convenience, usefulness, or reliability. Alternatively, it is possible to provide a novel lighting device that is excellent in convenience, usefulness, or reliability. Alternatively, it is possible to provide a novel organic compound, a novel light-emitting device, a novel display device, a novel electronic device, a novel light-emitting device, a novel lighting device, or a novel semiconductor device.

[0051] Furthermore, the description of these effects does not preclude the existence of other effects. Moreover, one aspect of the present invention does not necessarily have to possess all of these effects. Other effects will naturally become apparent from the description in the specification, drawings, and claims, and it is possible to extract other effects from the description in the specification, drawings, and claims. [Brief explanation of the drawing]

[0052] [Figure 1] Figures 1(A) and 1(B) illustrate the configuration of a light-emitting device according to one embodiment of the present invention. [Figure 2]Figures 2(A) and (B) illustrate the configuration of a light-emitting device according to one embodiment of the present invention. [Figure 3] Figures 3(A) and 3(B) illustrate the configuration of a display device according to an embodiment. [Figure 4] Figures 4(A) and 4(B) illustrate the configuration of a display device according to an embodiment. [Figure 5] Figures 5(A) and (B) are conceptual diagrams of an active matrix type light-emitting device. [Figure 6] Figures 6(A) and (B) are conceptual diagrams of an active matrix type light-emitting device. [Figure 7] Figure 7 is a conceptual diagram of an active matrix type light-emitting device. [Figure 8] Figures 8(A) and (B) are conceptual diagrams of a passive matrix type light-emitting device. [Figure 9] Figures 9(A) and (B) are diagrams representing lighting devices. [Figure 10] Figures 10(A) through (D) are diagrams representing electronic devices. [Figure 11] Figures 11(A) through (C) are diagrams representing electronic devices. [Figure 12] Figure 12 is a diagram representing a lighting device. [Figure 13] Figure 13 is a diagram representing a lighting device. [Figure 14] Figure 14 is a diagram representing an in-vehicle display device and lighting system. [Figure 15] Figures 15(A) through (C) are diagrams representing electronic devices. [Figure 16] Figures 16(A) and (B) show the 1H NMR spectra of 2αN-αNPhA-d7. [Figure 17] Figure 17 shows the absorption and emission spectra of 2αN-αNPhA-d7 in a toluene solution. [Figure 18] Figure 18 is a diagram illustrating the configuration of a light-emitting device according to an embodiment. [Figure 19]Figure 19 illustrates the current density-luminance characteristics of the light-emitting device according to the embodiment. [Figure 20] Figure 20 illustrates the brightness-current efficiency characteristics of the light-emitting device according to the embodiment. [Figure 21] Figure 21 illustrates the voltage-luminance characteristics of the light-emitting device according to the embodiment. [Figure 22] Figure 22 illustrates the voltage-current characteristics of the light-emitting device according to the embodiment. [Figure 23] Figure 23 illustrates the luminance-external quantum efficiency characteristics of the light-emitting device according to the embodiment. [Figure 24] Figure 24 illustrates the emission spectrum of the light-emitting device according to the embodiment. [Figure 25] Figure 25 illustrates the change in normalized brightness over time of the light-emitting device according to the embodiment. [Modes for carrying out the invention]

[0053] An organic compound according to one aspect of the present invention is represented by the following general formula (G1).

[0054] [ka]

[0055] However, in the above general formula (G1), R 1 ~R 26 At least one of them is deuterium, R 1 ~R 7 At least one of is a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted trialkylsilyl group, or a substituted or unsubstituted aryl group, R 1 ~R 7 Other than these, each is independently one of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted trialkylsilyl group, or a substituted or unsubstituted aryl group, R 8 ~R26 Each of these is independently one of the following: hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted trialkylsilyl group, or a substituted or unsubstituted aryl group. Alkyl groups have 3 to 10 carbon atoms, cycloalkyl groups have 3 to 10 carbon atoms, trialkylsilyl groups have 3 to 12 carbon atoms, and aryl groups have 6 to 25 carbon atoms.

[0056] This allows for the increased bond dissociation energy of a compound by utilizing carbon-deuterium bonds, which have a higher bond dissociation energy than carbon-hydrogen bonds. Furthermore, it can suppress bond dissociation within the compound structure in the excited state. It can also suppress the degradation or alteration of the compound due to the dissociation of carbon-deuterium bonds. Additionally, it can suppress the formation of degradation products. For example, it can be suitably used in the light-emitting layer of a light-emitting device. It can also be suitably used in a layer in contact with the light-emitting layer of a light-emitting device. In this way, it is possible to provide a novel organic compound with excellent convenience, usefulness, and reliability.

[0057] Embodiments will be described in detail with reference to the drawings. However, it will be readily apparent to those skilled in the art that the present invention is not limited to the following description, and that its form and details can be modified in various ways without departing from the spirit and scope of the present invention. Accordingly, the present invention is not to be interpreted as being limited to the contents of the embodiments shown below. In the configuration of the invention described below, the same reference numerals are used in common across different drawings for the same parts or parts having similar functions, and repeated descriptions are omitted.

[0058] (Embodiment 1) This embodiment describes an organic compound according to one aspect of the present invention.

[0059] <Example 1 of an organic compound> The organic compound described in this embodiment is an organic compound represented by the following general formula (G1).

[0060] [ka]

[0061] However, in the above general formula (G1), R 1 ~R 26 At least one of them is deuterium.

[0062] Also, R 1 ~R 7 At least one of the following is a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted trialkylsilyl group, or a substituted or unsubstituted aryl group. Also, R 1 ~R 7 Other than these, each is independently one of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted trialkylsilyl group, or a substituted or unsubstituted aryl group. In this specification, hydrogen includes deuterium.

[0063] R 8 ~R 26 Each of these is independently one of the following: hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted trialkylsilyl group, or a substituted or unsubstituted aryl group.

[0064] Note, R 1 ~R 26 The alkyl group to be substituted has 3 to 10 carbon atoms, R 1 ~R 26 The cycloalkyl group to be substituted has 3 to 10 carbon atoms, R 1 ~R 26 The trialkylsilyl group to be substituted has 3 to 12 carbon atoms, R 1 ~R 26 The aryl group to be substituted has between 6 and 25 carbon atoms.

[0065] R 1 ~R 26Examples of alkyl groups that can be substituted include propyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, octyl group, and decyl group.

[0066] Also, R 1 ~R 26 Examples of cycloalkyl groups to be substituted include cyclopropyl, cyclopentyl, cyclohexyl, adamantyl, bicyclo[2.2.1]heptyl, and tricyclo[5.2.1.0 2,6 Examples include decanyl groups and noadamantyl groups.

[0067] Also, R 1 ~R 26 Examples of trialkylsilyl groups that can be substituted include trimethylsilyl group, triethylsilyl group, and tert-butyldimethylsilyl group.

[0068] Also, R 1 ~R 26 Examples of aryl groups that can be substituted include phenyl, naphthyl, acenaphthyrenyl, anthryl, phenanthryl, biphenyl, triphenylenyl, fluorenyl, and spirofluorenyl groups.

[0069] Note, R 1 ~R 26 Any of the above-mentioned substituents that can be substituted may have other substituents. Examples of other substituents include the alkyl groups, cycloalkyl groups, trialkylsilyl groups, aryl groups, or deuterium.

[0070] This allows for increasing the bond dissociation energy of a compound by utilizing the carbon-deuterium bond, which has a higher bond dissociation energy than the carbon-hydrogen bond. Also, in general formula (G1), R 1 ~R 26 It is preferable that at least one of them is deuterium because it stabilizes the molecular structure, R 1 ~R 26It is even more preferable if all of the atoms are deuterium. Furthermore, it can suppress bond dissociation within the compound structure in the excited state. It can also suppress degradation or alteration of the compound due to the dissociation of carbon-deuterium bonds. Furthermore, it can suppress the formation of degraded products. For example, it can be suitably used in the light-emitting layer of a light-emitting device. It can also be suitably used in a layer in contact with the light-emitting layer of a light-emitting device. Even if the hydrogen bonded to the carbon of an organic compound is replaced with deuterium, the emission spectrum and quantum yield of the organic compound do not change significantly. Therefore, an organic compound having deuterium instead of hydrogen can improve the heat resistance without impairing the light-emitting properties of the light-emitting device using it. Furthermore, it can suppress the degradation of the organic compound in the manufacturing process of a light-emitting device, for example, in a manufacturing process involving heating such as a vacuum deposition process. Furthermore, it can suppress degradation associated with the operation of the light-emitting device. In this way, a novel organic compound with excellent convenience, usefulness, and reliability can be provided.

[0071] 《Specific Example of an Organic Compound 1》 Specific examples of organic compounds having the above configuration are shown below.

[0072] [ka]

[0073] [ka]

[0074] <Example of an organic compound 2> Furthermore, the organic compound described in this embodiment is an organic compound represented by the following general formula (G1).

[0075] [ka]

[0076] However, in the above general formula (G1), R 1~R 7 It is hydrogen.

[0077] Also, R 20 ~R 26 At least one of them is deuterium, R 20 ~R 26 Other than and R 8 ~R 19 Each of these is independently one of the following: hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted trialkylsilyl group, or a substituted or unsubstituted aryl group.

[0078] Note, R 8 ~R 26 The alkyl group to be substituted has 3 to 10 carbon atoms, R 8 ~R 26 The cycloalkyl group to be substituted has 3 to 10 carbon atoms, R 8 ~R 26 The trialkylsilyl group to be substituted has 3 to 12 carbon atoms, R 8 ~R 26 The aryl group to be substituted has between 6 and 25 carbon atoms.

[0079] Furthermore, the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) of the organic compound represented by general formula (G1) are distributed in the anthracene skeleton. Hydrogen directly bonded to the anthracene skeleton, specifically, preferably R 20 ~R 26 At least one of, more preferably R 20 ~R 26By deuterizing all of the components, the dissociation of carbon-hydrogen bonds that can occur can be suppressed. In other words, the dissociation of carbon-deuterium bonds can be suppressed. Furthermore, the dissociation of carbon-deuterium bonds can be suppressed in the excited state. Furthermore, the dissociation of carbon-deuterium bonds can be suppressed in the hole state. Furthermore, the dissociation of carbon-deuterium bonds can be suppressed in the electron state. In addition, for example, it can be used in the light-emitting layer of a light-emitting device to improve reliability. Furthermore, the decrease in luminescence efficiency associated with the operation of a light-emitting device can be suppressed. As a result, a novel organic compound with excellent convenience, usefulness, or reliability can be provided.

[0080] 《Specific Examples of Organic Compounds 2》 Specific examples of organic compounds having the above configuration are shown below.

[0081] [ka]

[0082] <Example 3 of organic compounds> Furthermore, the organic compound described in this embodiment is an organic compound represented by the following general formula (G2).

[0083] [ka]

[0084] However, in the above general formula (G2), R 1 ~R 7 Each of these is independently either a hydrogen atom or a substituted or unsubstituted aryl group.

[0085] Also, R 8 ~R 19 Each of these is independently one of the following: hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted trialkylsilyl group, or a substituted or unsubstituted aryl group.

[0086] In addition, the alkyl group to be substituted for R 8 or R 19 has 3 to 10 carbon atoms, and the cycloalkyl group to be substituted for R 8 or R 19 has 3 to 10 carbon atoms, and the trialkylsilyl group to be substituted for R 8 or R 19 has 3 to 12 carbon atoms, and the aryl group to be substituted for R 8 or R 19 has 6 to 25 carbon atoms.

[0087] In addition, the HOMO and LUMO of the organic compound represented by the general formula (G2) are distributed in the anthracene skeleton. By deuterating all of the hydrogens directly bonded to the anthracene skeleton, specifically, R 20 or R 26 it is possible to suppress bond dissociation that can occur in the carbon-hydrogen bond. That is, it is possible to suppress the dissociation of the carbon-deuterium bond. Also, in the excited state, it is possible to suppress the dissociation of the carbon-deuterium bond. Also, in the state having a hole, it is possible to suppress the dissociation of the carbon-deuterium bond. Also, in the state having an electron, it is possible to suppress the dissociation of the carbon-deuterium bond. Further, for the substituents introduced into the naphthyl group substituted at the 2-position and 9-position of the anthracene skeleton and the phenyl group substituted at the 10-position, an effect of improving the heat resistance of the organic compound of the present invention can be expected. Also, an effect of adjusting the molecular orientation can be expected. Also, an effect of improving the light extraction efficiency of the light-emitting device can be expected. Also, an effect of adjusting the carrier transportability can be expected. Also, the carrier balance of the light-emitting device can be adjusted. Also, the driving voltage of the light-emitting device can be reduced. As a result, it is possible to provide a novel organic compound excellent in convenience, usefulness or reliability.

[0088] 《Specific Example 3 of Organic Compound》 Specific examples of the organic compound having the above configuration are shown below.

[0089]

Chemical Formula

[0090] <Example 4 of organic compounds> Furthermore, the organic compound described in this embodiment is an organic compound represented by the following general formula (G2).

[0091] [ka]

[0092] However, in the above general formula (G2), R 1 ~R 7 Each of these is independently a hydrogen atom or a substituted or unsubstituted aryl group.

[0093] Also, R 8 ~R 19 It is hydrogen.

[0094] Note, R 1 ~R 7 The aryl group to be substituted has between 6 and 25 carbon atoms.

[0095] 《Specific Examples of Organic Compounds 4》 Specific examples of organic compounds having the above configuration are shown below.

[0096] [ka]

[0097] [ka]

[0098] <Methods for synthesizing organic compounds> A method for synthesizing an organic compound according to one aspect of the present invention will be explained below using the synthesis scheme shown.

[0099] The organic compound represented by general formula (G1) can be obtained, for example, by coupling an anthracene derivative halogen compound or a compound having a triflate group with a naphthalene compound boronic acid or organoboron compound and a benzene compound boronic acid or organoboron compound via the Suzuki-Miyaura coupling reaction.

[0100] (a1) is a halogen compound or a compound having a triflate group of an anthracene derivative, (a2) and (a3) ​​are boronic acids or organoboron compounds of naphthalene compounds, and (a4) is a boronic acid or organoboron compound of benzene compounds.

[0101] [ka]

[0102] In the above synthesis scheme, R 1 ~R 26 At least one of them is deuterium. Also, R 1 ~R 7 At least one of the following is a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted trialkylsilyl group, or a substituted or unsubstituted aryl group. Also, R 1 ~R 7 Other than these, each is independently one of the following: hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted trialkylsilyl group, or a substituted or unsubstituted aryl group. 8 ~R 26 Each of these is independently one of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted trialkylsilyl group, or a substituted or unsubstituted aryl group. Also, R 27 and R 28 It is hydrogen.

[0103] Also, R 29 ~R 34Each of these independently represents either hydrogen or an alkyl group having 1 to 6 carbon atoms, R 29 and R 30 , R 31 and R 32 , R 33 and R 34 They may be joined to each other to form a ring.

[0104] Also, X 1 ~X 3 Each of these independently represents a halogen or a triflate group, and X 1 ~X 3 In the case of halogens, chlorine, bromine, and iodine are particularly preferred.

[0105] Examples of palladium catalysts that can be used in the coupling reaction represented by the above synthesis scheme include palladium(II) acetate, tetrakis(triphenylphosphine)palladium(O), and bis(triphenylphosphine)palladium(II) dichloride.

[0106] Examples of ligands for the above-mentioned palladium catalyst include tri(ortho-tolyl)phosphine, triphenylphosphine, and tricyclohexylphosphine.

[0107] Examples of bases that can be used in the coupling reaction represented by the above synthesis scheme include organic bases such as sodium tert-butoxide, and inorganic bases such as potassium carbonate and sodium carbonate.

[0108] In the coupling reaction represented by the above synthesis scheme, suitable solvents include mixed solvents of toluene and water, mixed solvents of toluene and an alcohol such as ethanol and water, mixed solvents of xylene and water, mixed solvents of xylene and an alcohol such as ethanol and water, mixed solvents of benzene and water, mixed solvents of benzene and an alcohol such as ethanol and water, and mixed solvents of ethers such as ethylene glycol dimethyl ether and water. However, the solvents that can be used are not limited to these. Furthermore, mixed solvents of toluene and water, or mixed solvents of toluene, ethanol and water, or mixed solvents of ethers such as ethylene glycol dimethyl ether and water are more preferred.

[0109] Furthermore, in the Suzuki-Miyaura coupling reaction shown in the above synthesis scheme, an organoboron compound or boronic acid of an anthracene compound may be coupled with a halide or triflate-substituted naphthalene compound and a halide or triflate-substituted benzene compound.

[0110] Furthermore, the reactions carried out in the above synthesis scheme are not limited to the Suzuki-Miyaura coupling reaction; the Migita-Kosugi-Still coupling reaction using organotin compounds, coupling reactions using Grignard reagents, and the Ullmann reaction using copper or copper compounds can also be used.

[0111] Furthermore, examples of halogenating reagents that can be used in the halogenation reaction described in the above synthesis scheme include bromine, iodine, N-bromosuccinimide, N-chlorosuccinimide, and N-iodosuccinimide.

[0112] Furthermore, examples of solvents that can be used in the halogenation reaction in the above synthesis scheme include acetone, toluene, N,N-dimethylformamide, ethyl acetate, chloroform, and dichloromethane.

[0113] Furthermore, in the above scheme, if the hydrogen in any of the units (a1) to (a4) is deuterated, a deuterated product can be obtained by the deuteration reaction of the desired unit.

[0114] Furthermore, as a synthesis method for (G1), R in (G1) 1 ~R 26 (G1) can also be obtained by using a compound that does not contain deuterium as a precursor to (G1) and deuterating the precursor.

[0115] In the above deuteration reaction, suitable solvents include benzene-d6, toluene-d8, xylene-d10, and heavy water. However, the solvents that can be used are not limited to these.

[0116] Furthermore, in the above deuteration reaction, examples of catalysts that can be used include molybdenum(V) chloride, tungsten(VI) chloride, niobium(V) chloride, tantalum(V) chloride, aluminum(III) chloride, titanium(IV) chloride, and tin(IV) chloride. However, the catalysts that can be used are not limited to these.

[0117] An anthracene compound for host materials according to one aspect of the present invention can be synthesized as described above.

[0118] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0119] (Embodiment 2) In this embodiment, the configuration of a light-emitting device 550X according to one aspect of the present invention will be described with reference to Figures 1(A) and (B).

[0120] Figure 1(A) is a cross-sectional view illustrating the configuration of a light-emitting device according to one embodiment of the present invention, and Figure 1(B) is a diagram illustrating the energy levels of the material used in the light-emitting device according to one embodiment of the present invention.

[0121] In this specification, variables that take integer values ​​of 1 or more may be used as signs. For example, (p), which includes a variable p that takes an integer value of 1 or more, may be used as part of a sign that identifies any of up to p components. Also, for example, (m,n), which includes a variable m and a variable n that take integer values ​​of 1 or more, may be used as part of a sign that identifies any of up to m × n components.

[0122] <Example configuration of the 550X light-emitting device> The light-emitting device 550X described in this embodiment includes an electrode 551X, an electrode 552X, and a unit 103X. Electrode 552X overlaps with electrode 551X, and unit 103X is sandwiched between electrodes 551X and 552X.

[0123] <Example configuration of Unit 103X> Unit 103X has a single-layer or multi-layer structure. For example, unit 103X has layers 111X, 112, and 113 (see Figure 1(A)). Unit 103X has the function of emitting optical ELX.

[0124] Layer 111X is sandwiched between layers 112 and 113, layer 112 is sandwiched between electrode 551X and layer 111X, and layer 113 is sandwiched between electrode 552X and layer 111X.

[0125] For example, a layer selected from functional layers such as an emissive layer, a hole transport layer, an electron transport layer, and a carrier block layer can be used in unit 103X. Furthermore, a layer selected from functional layers such as a hole injection layer, an electron injection layer, an exciton block layer, and a charge generation layer can also be used in unit 103X.

[0126] 《Example of Layer 111X Configuration 1》 A material with carrier transport properties can be used in layer 111X. For example, a material with carrier transport properties can be used as the host material. It is preferable to use a host material with a larger band gap than the luminescent material contained in layer 111X. This suppresses energy transfer from excitons generated in layer 111X to the host material.

[0127] [Example 1 of host material configuration having an anthracene skeleton] Organic compounds having an anthracene skeleton can be used as host materials. In particular, organic compounds having an anthracene skeleton are suitable when fluorescent materials are used as the light-emitting material. This makes it possible to realize light-emitting devices with good luminescence efficiency and durability.

[0128] For example, the organic compound described in Embodiment 1 can be used as the host material.

[0129] This allows for increased bond dissociation energy of compounds by utilizing carbon-deuterium bonds, which have a higher bond dissociation energy than carbon-hydrogen bonds. Furthermore, it can suppress bond dissociation within the compound structure in the excited state. It can also suppress degradation or alteration of compounds due to carbon-deuterium bond dissociation. Additionally, it can suppress the formation of degradation products. Furthermore, it can suppress the decrease in luminescence efficiency due to degradation products. This also allows for the provision of light-emitting devices with high luminescence efficiency, a good operating life, and reduced changes in emission color during operation. Finally, it allows for the provision of light-emitting devices with high color purity. As a result, it is possible to provide novel light-emitting devices with superior convenience, usefulness, and reliability.

[0130] [Example of mixed material composition] Furthermore, a material composed of a mixture of multiple substances can be used as the host material. For example, a material with hole-transporting properties and a material with electron-transporting properties can be used in the mixture. For example, a material with hole-transporting properties that can be used in layer 112 can be used in the mixture. Also, for example, a material with electron-transporting properties that can be used in layer 113 can be used in the mixture.

[0131] The weight ratio of hole-transporting material to electron-transporting material in the mixed material should be (hole-transporting material / electron-transporting material) = (1 / 19) or greater and (19 / 1) or less. This allows for easy adjustment of the carrier transport properties of layer 111X. Furthermore, the recombination region can be easily controlled.

[0132] 《Example of Layer 111X Configuration 2》 For example, a light-emitting material can be used for layer 111X. Alternatively, a light-emitting material and a host material can be used for layer 111X. Layer 111X can also be referred to as a light-emitting layer. It is preferable to place layer 111X in the region where holes and electrons recombine. This allows the energy generated by carrier recombination to be efficiently emitted as light.

[0133] Furthermore, it is preferable to position layer 111X away from the metal used for electrodes, etc. This makes it possible to suppress the quenching phenomenon caused by the metal used for electrodes, etc.

[0134] Furthermore, it is preferable to adjust the distance from the reflective electrodes, etc., to the layer 111X and position the layer 111X at an appropriate location according to the emission wavelength. This allows for the amplification of the light amplitudes by utilizing the interference phenomenon between the light reflected by the electrodes, etc., and the light emitted by the layer 111X. In addition, it is possible to strengthen light of a predetermined wavelength and narrow the light spectrum. Furthermore, a vivid emission color can be obtained with high intensity. In other words, by positioning the layer 111X at an appropriate location between the electrodes, etc., a microcavity structure can be constructed.

[0135] For example, fluorescent materials, phosphorescent materials, or materials exhibiting thermally delayed fluorescence (TADF) can be used as luminescent materials. This allows the energy generated by carrier recombination to be released from the luminescent material as photo-ELX (see Figure 1(A)).

[0136] [Fluorescent material] A fluorescent material can be used in layer 111X. For example, the fluorescent materials exemplified below can be used in layer 111X. However, this is not limited to these examples, and various known fluorescent materials can be used in layer 111X.

[0137] Specifically, these include 5,6-bis[4-(10-phenyl-9-antryl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl-9-antryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), N,N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), and N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl] Nyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N,N'-bis[4-(9H-carbazole-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazole-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazole-9-yl)-4'-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviation :2YGAPPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra(tert-butyl)perylene (abbreviation: TBP), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBAPA), N,N''-(2-tert-butylanthracene-9,10-diyldi-4,1-phenylene)bis[N,N',N '-triphenyl-1,4-phenylenediamine' (abbreviation: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: 2PCAPPA), N,N'-(pyrene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03), 3,10-bis[N-(9-phenyl-9H-carbazole-2-yl)-N-phenylamino]naphtho[2,3-b;[6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nbf(IV)-02), 3,10-bis[N-(dibenzofuran-3-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10FrA2Nbf(IV)-02), etc. can be used.

[0138] In particular, condensed aromatic diamine compounds, such as pyrenediamine compounds like 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6BnfAPrn-03, are preferred because they exhibit high hole-trapping properties and excellent luminescence efficiency or reliability.

[0139] Also, N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA), N,N,N',N',N'',N'',N''',N'''-octaphenyldibenzo[g,p]chrysen-2,7,10,15-tetraamine (abbreviation: DBC1), coumarin 30, 9,10-diphenyl-2-[N-phenyl-N-(9-phenylcarbazole-3-yl)-amino]-anthracene (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-to Riphenyl-1,4-phenylenediamine (abbreviated as 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPABPhA), 9,10-bis(1,1'-biphenyl-2-yl)-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracene-2-amine (abbreviated as 2YGABPhA), N,N,9-triphenylanthracene-9-amine (abbreviated as DPhAPhA), coumarin 545T, N,N'-diphenylquinacridone (abbreviated as DPQd), rubren, 5,12-bis(1,1'-biphenyl-4-yl)-6,11-diphenyltetracene (abbreviated as BPT), etc. can be used.

[0140] Also, 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl-4H-pyran-4-ylidene)propanedinitrile (abbreviation: DCM1), 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinoridine-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N',N'-tetrakis (4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluorantene-3,10-diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]k [Noridin-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]quinoridin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTB), 2-(2,6-bis{2-[4-(di You can use methylamino)phenyl]ethenyl}-4H-pyran-4-ylidene)propanedinitrile (abbreviation: BisDCM), 2-{2,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinoridine-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: BisDCJTM), etc.

[0141] [Substances exhibiting thermally activated delayed fluorescence (TADF)] TADF material can be used for layer 111X. For example, the TADF material exemplified below can be used as a luminescent material. However, it is not limited to this, and various known TADF materials can be used as luminescent materials.

[0142] TADF materials have a small difference between the S1 and T1 energy levels, allowing for reverse intersystem crossing (upconversion) from a triplet excited state to a singlet excited state with minimal thermal energy. This enables efficient generation of singlet excited states from triplet excited states. Furthermore, the triplet excitation energy can be converted into luminescence.

[0143] Furthermore, an excited complex (also called an exciplex) that forms an excited state with two types of substances has an extremely small difference between the S1 and T1 levels and functions as a TADF material that can convert triplet excitation energy into singlet excitation energy.

[0144] Furthermore, the phosphorescence spectrum observed at low temperatures (e.g., 77K to 10K) can be used as an indicator of the T1 level. For TADF materials, when a tangent is drawn at the short-wavelength tail of the fluorescence spectrum and the energy at the wavelength of the extrapolation is taken as the S1 level, and when a tangent is drawn at the short-wavelength tail of the phosphorescence spectrum and the energy at the wavelength of the extrapolation is taken as the T1 level, it is preferable that the difference between S1 and T1 is 0.3 eV or less, and more preferably 0.2 eV or less.

[0145] Furthermore, when using TADF material as a light-emitting material, it is preferable that the S1 level of the host material is higher than the S1 level of the TADF material. Also, it is preferable that the T1 level of the host material is higher than the T1 level of the TADF material.

[0146] For example, fullerenes and their derivatives, acridines and their derivatives, eosin derivatives, etc., can be used as TADF materials. In addition, metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd), etc., can be used as TADF materials.

[0147] Specifically, the following can be used: protoporphyrin-tin fluoride complex (SnF2(Proto IX)), mesoporphyrin-tin fluoride complex (SnF2(Meso IX)), hematoporphyrin-tin fluoride complex (SnF2(Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complex (SnF2(Copro III-4Me)), octaethylporphyrin-tin fluoride complex (SnF2(OEP)), etioporphyrin-tin fluoride complex (SnF2(Etio I)), octaethylporphyrin-platinum chloride complex (PtCl2OEP), etc., whose structural formulas are shown below.

[0148] [ka]

[0149] Furthermore, for example, heterocyclic compounds having one or both of a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring can be used as TADF materials.

[0150] Specifically, the structural formulas are as follows: 2-(biphenyl-4-yl)-4,6-bis(12-phenylindoro[2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ), 9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazol (abbreviation: PCCzTzn), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 2-[4-(10H-phenoxazine-10-yl)phenyl]-4 ,6-diphenyl-1,3,5-triazine (abbreviated as PXZ-TRZ), 3-[4-(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (abbreviated as PPZ-3TPT), 3-(9,9-dimethyl-9H-acridine-10-yl)-9H-xanthene-9-one (abbreviated as ACRXTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviated as DMAC-DPS), 10-phenyl-10H,10'H-spiro[acridine-9,9'-anthracene]-10'-one (abbreviated as ACRSA), etc. can be used.

[0151] [ka]

[0152] The heterocyclic compound is preferred because it has both a π-electron-excess heteroaromatic ring and a π-electron-deficient heteroaromatic ring, resulting in high electron transport and hole transport properties. In particular, among the skeletons having a π-electron-deficient heteroaromatic ring, the pyridine skeleton, diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton), and triazine skeleton are preferred because they are stable and reliable. In particular, the benzoflopyrimidine skeleton, benzothienopyrimidine skeleton, benzoflopyrazine skeleton, and benzothienopyrazine skeleton are preferred because they have high acceptability and are reliable.

[0153] Furthermore, among skeletons having a π-electron-excess heteroaromatic ring, the acridine skeleton, phenoxazine skeleton, phenothiazine skeleton, furan skeleton, thiophene skeleton, and pyrrole skeleton are stable and reliable, and therefore it is preferable to have at least one of these skeletons. Dibenzofuran is preferred as the furan skeleton, and dibenzothiophene is preferred as the thiophene skeleton. Indole, carbazole, indrocarbazole, bicarbazole, and 3-(9-phenyl-9H-carbazole-3-yl)-9H-carbazole are particularly preferred as the pyrrole skeleton.

[0154] Furthermore, a substance in which a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring are directly bonded is particularly preferable because both the electron-donating and electron-accepting properties of the π-electron-rich heteroaromatic ring are strengthened, resulting in a smaller energy difference between the S1 and T1 levels, thus efficiently obtaining thermally activated delayed fluorescence. Alternatively, an aromatic ring bonded to an electron-withdrawing group such as a cyano group may be used instead of the π-electron-deficient heteroaromatic ring. Additionally, aromatic amine skeletons, phenazine skeletons, and the like can be used as the π-electron-rich skeleton.

[0155] Furthermore, as π-electron-deficient skeletons, xanthene skeletons, thioxanthene dioxide skeletons, oxadiazole skeletons, triazole skeletons, imidazole skeletons, anthraquinone skeletons, boron-containing skeletons such as phenylborane or volanthrene, aromatic rings or heteroaromatic rings having a nitrile group or cyano group such as benzonitrile or cyanobenzene, carbonyl skeletons such as benzophenone, phosphine oxide skeletons, sulfone skeletons, and the like can be used.

[0156] Thus, a π-electron-deficient skeleton and a π-electron-excess skeleton can be used instead of at least one of a π-electron-deficient heteroaromatic ring and a π-electron-excess heteroaromatic ring.

[0157] Example of Layer 112 configuration For example, a material with hole-transporting properties can be used for layer 112. Layer 112 can also be referred to as a hole-transporting layer. It is preferable to use a material for layer 112 that has a larger band gap than the luminescent material contained in layer 111X. This suppresses energy transfer from excitons generated in layer 111X to layer 112.

[0158] [Materials with hole transport properties] The hole mobility is 1 × 10⁻⁶. -6 cm 2 Materials with a Vs of / Vs or higher can be suitably used as materials with hole transport properties.

[0159] For example, amine compounds or organic compounds having a π-electron-rich heteroaromatic ring skeleton can be used in hole-transporting materials. Specifically, compounds having an aromatic amine skeleton, a carbazole skeleton, a thiophene skeleton, a furan skeleton, etc., can be used. Compounds having an aromatic amine skeleton or a carbazole skeleton are particularly preferred because they offer good reliability, high hole transportability, and contribute to reducing the driving voltage.

[0160] Examples of compounds having an aromatic amine skeleton include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated as BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated as mBPAFLP), and 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCBA1BP). ,4'-diphenyl-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]spiro-9,9'-bifluoren-2-amine (abbreviation: PCBASF), etc. can be used.

[0161] Examples of compounds having a carbazole skeleton include 1,3-bis(N-carbazolyl)benzene (abbreviated as mCP), 4,4'-di(N-carbazolyl)biphenyl (abbreviated as CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviated as CzTP), 3,3'-bis(9-phenyl-9H-carbazole) (abbreviated as PCCP), and the like.

[0162] Examples of compounds having a thiophene skeleton include 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviated as DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviated as DBTFLP-III), 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviated as DBTFLP-IV), and others.

[0163] Examples of compounds having a furan skeleton include 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II), 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II), and others.

[0164] Example of Layer 113 configuration For example, electron-transporting materials, materials with an anthracene skeleton, and mixed materials can be used for layer 113. Layer 113 can also be referred to as an electron transport layer. It is preferable to use a material for layer 113 that has a larger band gap than the luminescent material contained in layer 111X. This suppresses energy transfer from excitons generated in layer 111X to layer 113.

[0165] [Materials with electron transport properties] For example, metal complexes or organic compounds having a π-electron-deficient heteroaromatic ring skeleton can be used as electron-transporting materials.

[0166] Under the condition that the square root of the electric field strength [V / cm] is 600, the electron mobility is 1 × 10⁻⁶. -7 cm 2 / Vs or more, 5×10 -5 cm 2Materials with a Vs of 0.5 / Vs or less can be suitably used as electron-transporting materials. This makes it possible to suppress electron transport in the electron transport layer, control the amount of electrons injected into the light-emitting layer, or prevent the light-emitting layer from becoming electron-excessive.

[0167] Examples of metal complexes that can be used include bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviated as BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviated as BAlq), bis(8-quinolinolato)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviated as ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviated as ZnBTZ), and the like.

[0168] Organic compounds having a π-electron-deficient heteroaromatic ring skeleton include, for example, heterocyclic compounds having a polyazole skeleton, heterocyclic compounds having a diazine skeleton, heterocyclic compounds having a pyridine skeleton, and heterocyclic compounds having a triazine skeleton. In particular, heterocyclic compounds having a diazine skeleton and heterocyclic compounds having a pyridine skeleton are preferred due to their good reliability. Furthermore, heterocyclic compounds having a diazine (pyrimidine or pyrazine) skeleton have high electron transport properties, which can reduce the driving voltage.

[0169] Examples of heterocyclic compounds having a polyazole skeleton include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviated as TAZ), and 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as O XD-7), 9-[4-(5-phenyl-1,3,4-oxadiazole-2-yl)phenyl]-9H-carbazole (abbreviated as CO11), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviated as TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviated as mDBTBIm-II), etc. can be used.

[0170] Examples of heterocyclic compounds having a diazine skeleton include 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3-(3'-dibenzothiophen-4-yl)biphenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), and 2-[3'-(9H-carbazole-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline. Noxaline (abbreviation: 2mCzBPDBq), 4,6-bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,8-bis[3-(dibenzothiophen-4-yl)phenyl]benzo[h]quinazoline (abbreviation: 4,8mDBtP2Bqn), etc. can be used.

[0171] Examples of heterocyclic compounds having a pyridine skeleton include 3,5-bis[3-(9H-carbazole-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), and others.

[0172] Examples of the heterocyclic compound having a triazine skeleton include, for example, 2-[3'-(9,9-dimethyl-9H-fluorene-2-yl)-1,1'-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn), 2-[(1,1'-biphenyl)-4-yl]-4-phenyl-6-[9,9'-spirobi(9H-fluorene)-2-yl]-1,3,5-triazine (abbreviation: BP-SFTzn), 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-8-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mBnfBPTzn), 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-6-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mBnfBPTzn-02), etc.

[0173] [Material 1 having an anthracene skeleton] An organic compound having an anthracene skeleton can be used for the layer 113. In particular, the organic compound having an anthracene skeleton described in Embodiment 1 can be used for the layer 113.

[0174] [Material 2 having an anthracene skeleton] In addition, an organic compound containing both an anthracene skeleton and a heterocyclic skeleton can be preferably used. For example, an organic compound containing both an anthracene skeleton and a nitrogen-containing 5-membered ring skeleton can be used. Alternatively, an organic compound containing both a nitrogen-containing 5-membered ring skeleton containing two heteroatoms in the ring and an anthracene skeleton can be used. Specifically, a pyrazole ring, an imidazole ring, an oxazole ring, a thiazole ring, etc. can be preferably used for the heterocyclic skeleton.

[0175] For example, an organic compound containing both an anthracene skeleton and a nitrogen-containing 6-membered ring skeleton can be used. Alternatively, an organic compound containing both a nitrogen-containing 6-membered ring skeleton containing two heteroatoms in the ring and an anthracene skeleton can be used. Specifically, a pyrazine ring, a pyrimidine ring, a pyridazine ring, etc. can be preferably used for the heterocyclic skeleton.

[0176] [Composition Example of Composite Material] In addition, a material obtained by mixing a plurality of substances can be used for layer 113. Specifically, a composite material containing an alkali metal, an alkali metal compound or an alkali metal complex and a substance having electron transporting properties can be used for layer 113. It is more preferable that the HOMO level of the material having electron transporting properties is -6.0 eV or more.

[0177] For example, a composite material of a substance having acceptor properties and a material having hole transporting properties can be used for layer 104. Specifically, a composite material of a substance having acceptor properties and a substance having a relatively deep HOMO level HM1 of -5.7 eV or more and -5.4 eV or less can be used for layer 104 (see Fig. 1(B)). In combination with the configuration in which such a composite material is used for layer 104, the composite material can be suitably used for layer 113. Thereby, the reliability of the light-emitting device can be improved.

[0178] In addition, a configuration in which a material having hole transporting properties is used for layer 112 can be combined with the configuration in which the composite material is used for layer 104 and the composite material is used for layer 113, and can be suitably used. For example, a substance having a HOMO level HM2 in the range of -0.2 eV or more and 0 eV or less with respect to the relatively deep HOMO level HM1 can be used for layer 112 (see Fig. 1(B)). Thereby, the reliability of the light-emitting device can be improved. In this specification and the like, the above light-emitting device may be referred to as a Recombination-Site Tailoring Injection structure (ReSTI structure).

[0179] A configuration in which an alkali metal, an alkali metal compound or an alkali metal complex is present with a concentration difference (including the case where it is 0) in the thickness direction of layer 113 is preferable.

[0180] For example, metal complexes containing an 8-hydroxyquinolinate structure can be used. Alternatively, methyl-substituted metal complexes containing an 8-hydroxyquinolinate structure (e.g., 2-methyl-substituted or 5-methyl-substituted) can also be used.

[0181] As metal complexes containing the 8-hydroxyquinolinate structure, 8-hydroxyquinolinate-lithium (abbreviated as Liq), 8-hydroxyquinolinate-sodium (abbreviated as Naq), etc., can be used. In particular, monovalent metal ion complexes are preferred, among lithium complexes, and Liq is more preferred.

[0182] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0183] (Embodiment 3) In this embodiment, the configuration of a light-emitting device 550X according to one aspect of the present invention will be described with reference to Figure 1(A).

[0184] <Example configuration of the 550X light-emitting device> The light-emitting device 550X described in this embodiment includes an electrode 551X, an electrode 552X, a unit 103X, and a layer 104. Electrode 552X overlaps with electrode 551X, and unit 103X is sandwiched between electrodes 551X and 552X. Layer 104 is also sandwiched between electrode 551X and unit 103X. For example, the configuration described in Embodiment 2 can be used for unit 103X.

[0185] <Example configuration of electrode 551X> For example, conductive materials can be used for electrode 551X. Specifically, films containing metals, alloys, or conductive compounds can be used for electrode 551X in a single layer or in a multilayer structure.

[0186] For example, a film that efficiently reflects light can be used for electrode 551X. Specifically, an alloy containing silver and copper, an alloy containing silver and palladium, or a metal film such as aluminum can be used for electrode 551X.

[0187] Furthermore, for example, a metal film that transmits some of the light and reflects other parts of the light can be used for the electrode 551X. This allows for the creation of a microcavity structure in the light-emitting device 550X. Alternatively, it may be possible to extract light of a predetermined wavelength more efficiently than other light. Alternatively, it may be possible to extract light with a narrow spectral full width at half maximum. Alternatively, it may be possible to extract light of vivid colors.

[0188] Furthermore, for example, a film that is transparent to visible light can be used for the electrode 551X. Specifically, a thin metal film, alloy film, or conductive oxide film that is thin enough to transmit light can be used for the electrode 551X in a single layer or in a multilayer structure.

[0189] In particular, materials with a work function of 4.0 eV or higher can be suitably used for electrode 551X.

[0190] For example, conductive oxides containing indium can be used. Specifically, indium oxide, indium oxide-tin oxide (abbreviated as ITO), indium oxide-tin oxide containing silicon or silicon oxide (abbreviated as ITSO), indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide (abbreviated as IWZO), etc., can be used.

[0191] Furthermore, conductive oxides containing zinc can be used, for example. Specifically, zinc oxide, zinc oxide with added gallium, and zinc oxide with added aluminum can be used.

[0192] Further, for example, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), or nitrides of metallic materials (e.g., titanium nitride) can be used. Alternatively, graphene can be used.

[0193] 《Configuration Example 1 of Layer 104》 A material having hole injection property can be used for layer 104. Also, layer 104 can be referred to as a hole injection layer.

[0194] For example, when the square root of the electric field strength [V / cm] is 600, the hole mobility is 1×10 -3 cm 2 / Vs or less, such a material can be used for layer 104. Also, a film having a resistivity of 1×10 4 [Ω·cm] or more and 1×10 7 [Ω·cm] or less can be used for layer 104. Preferably, layer 104 has a resistivity of 5×10 4 [Ω·cm] or more and 1×10 7 [Ω·cm] or less, and more preferably, it has a resistivity of 1×10 5 [Ω·cm] or more and 1×10 7 [Ω·cm] or less.

[0195] 《Configuration Example 2 of Layer 104》 Specifically, a substance having acceptor property can be used for layer 104. Alternatively, a composite material containing a plurality of substances can be used for layer 104. Thereby, holes can be easily injected, for example, from electrode 551X. Or, the driving voltage of light-emitting device 550X can be reduced.

[0196] [Substance having acceptor property] Organic compounds and inorganic compounds can be used as the substance having acceptor property. The substance having acceptor property can extract electrons from an adjacent hole transport layer or a material having hole transport property by applying an electric field.

[0197] For example, compounds having electron-withdrawing groups (halogen or cyano groups) can be used as acceptor materials. Furthermore, organic compounds with acceptor properties are easily vapor-deposited and readily formed into films. This can increase the productivity of the 550X light-emitting device.

[0198] Specifically, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviated as F4-TCNQ), chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviated as HAT-CN), 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviated as F6-TCNNQ), 2-(7-dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyrene-2-ylidene)malononitrile, etc. can be used.

[0199] In particular, compounds in which an electron-withdrawing group is bonded to a condensed aromatic ring having multiple heteroatoms, such as HAT-CN, are thermally stable and therefore preferred.

[0200] Furthermore, radialene derivatives having electron-withdrawing groups (especially halogen groups such as fluoro groups or cyano groups) [3] are preferred because they have very high electron-accepting properties.

[0201] Specifically, α,α',α''-1,2,3-cyclopropanetriylidenates[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α',α''-1,2,3-cyclopropanetriylidenates[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], α,α',α''-1,2,3-cyclopropanetriylidenates[2,3,4,5,6-pentafluorobenzeneacetonitrile], etc., can be used.

[0202] Furthermore, molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide, and the like can be used as acceptor materials.

[0203] Furthermore, phthalocyanine-based complex compounds such as phthalocyanine (abbreviated as H2Pc) and copper phthalocyanine (CuPc), and compounds having an aromatic amine skeleton such as 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated as DPAB) and N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviated as DNTPD) can be used.

[0204] Furthermore, polymers such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) can be used.

[0205] [Example of composite material composition 1] Furthermore, for example, a composite material containing an acceptor and a hole transporter can be used for layer 104. This allows not only materials with high work functions but also materials with low work functions to be used for electrode 551X. Alternatively, the material to be used for electrode 551X can be selected from a wide range of materials, regardless of the work function.

[0206] For example, compounds having an aromatic amine skeleton, carbazole derivatives, aromatic hydrocarbons, aromatic hydrocarbons having a vinyl group, and polymer compounds (oligomers, dendrimers, polymers, etc.) can be used as hole transport materials in composite materials. Furthermore, if the hole mobility is 1 × 10⁻⁶ -6 cm 2 Materials with a Vs of 1 / V or higher can be suitably used as materials with hole transport properties in composite materials.

[0207] Furthermore, materials with relatively deep HOMO levels can be suitably used as hole-transporting materials in composite materials. Specifically, it is preferable that the HOMO level is between -5.7 eV and -5.4 eV. This facilitates the injection of holes into unit 103X. It also facilitates the injection of holes into layer 112. In addition, it improves the reliability of the light-emitting device 550X.

[0208] Examples of compounds having an aromatic amine skeleton include N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviated as DTDPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated as DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviated as DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviated as DPA3B).

[0209] Examples of carbazole derivatives include 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarb You can use zole (abbreviated as PCzPCN1), 4,4'-di(N-carbazolyl)biphenyl (abbreviated as CBP), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene (abbreviated as TCPB), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as CzPA), 1,4-bis[4-(N-carbazolyl)phenyl]-2,3,5,6-tetraphenylbenzene, etc.

[0210] Examples of aromatic hydrocarbons include 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 2-tert-butyl-9,10-di(1-naphthyl)anthracene, 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 2-tert-butyl-9,10-bis(4-phenylphenyl)anthracene (abbreviation: t-BuDBA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 9,10-diphenylanthracene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation: t-BuAnth), 9,10-bis(4-methyl-1-naphthyl)anthracene (abbreviation: DMNA), and 2-tert-butyl-9,10 -Bis[2-(1-naphthyl)phenyl]anthracene, 9,10-bis[2-(1-naphthyl)phenyl]anthracene, 2,3,6,7-tetramethyl-9,10-di(1-naphthyl)anthracene, 2,3,6,7-tetramethyl-9,10-di(2-naphthyl)anthracene, 9,9'-bianthryl, 10,10'-diphenyl-9,9'-bianthryl, 10,10'-bis(2-phenylphenyl)-9,9'-bianthryl, 10,10'-bis[(2,3,4,5,6-pentaphenyl)phenyl]-9,9'-bianthryl, anthracene, tetracene, rubrene, perylene, 2,5,8,11-tetra(tert-butyl)perylene, pentacene, coronene, etc. can be used.

[0211] Examples of aromatic hydrocarbons having a vinyl group include 4,4'-bis(2,2-diphenylvinyl)biphenyl (abbreviated as DPVBi), 9,10-bis[4-(2,2-diphenylvinyl)phenyl]anthracene (abbreviated as DPVPA), and the like.

[0212] Examples of polymer compounds that can be used include poly(N-vinylcarbazole) (abbreviated as PVK), poly(4-vinyltriphenylamine) (abbreviated as PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated as PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated as Poly-TPD), and the like.

[0213] Furthermore, for example, substances comprising any of the carbazole skeleton, dibenzofuran skeleton, dibenzothiophene skeleton, and anthracene skeleton can be suitably used as hole-transporting materials in composite materials. In addition, substances comprising aromatic amines having substituents including a dibenzofuran ring or a dibenzothiophene ring, aromatic monoamines having a naphthalene ring, or aromatic monoamines in which a 9-fluorenyl group is bonded to the nitrogen of the amine via an arylene group can be used as hole-transporting materials in composite materials. Moreover, using a substance having an N,N-bis(4-biphenyl)amino group can improve the reliability of the light-emitting device 550X.

[0214] Examples of these materials include N-(4-biphenyl)-6,N-diphenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BnfABP), N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf), 4,4'-bis(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)-4''-phenyltriphenylamine (abbreviation: BnfBB1BP), and N,N-bis(4-biphenyl)benzo[b]naphtho[1,2 -d]furan-6-amine (abbreviation: BBABnf(6)), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf(8)), N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviation: BBABnf(II)(4)), N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP), N-[4-(dibenzothiophen-4-yl)phenyl]-N-phenyl -4-biphenylamine (abbreviation: ThBA1BP), 4-(2-naphthyl)-4',4''-diphenyltriphenylamine (abbreviation: BBAβNB), 4-[4-(2-naphthyl)phenyl]-4',4''-diphenyltriphenylamine (abbreviation: BBAβNBi), 4,4'-diphenyl-4''-(6;1'-binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβNB), 4,4'-diphenyl-4''-(7;1'-binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβNB-0 3) 4,4'-diphenyl-4''-(7-phenyl)naphthyl-2-yltriphenylamine (abbreviation: BBAPβNB-03), 4,4'-diphenyl-4''-(6;2'-binaphthyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B), 4,4'-diphenyl-4''-(7;2'-binaphthyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B-03), 4,4'-diphenyl-4''-(4;2'-binaphthyl-1-yl)triphenylamine (abbreviation: BBAβNαNB), 4,4'-Diphenyl-4''-(5;2'-binaphthyl-1-yl)triphenylamine (abbreviation: BBAβNαNB-02), 4-(4-biphenylyl)-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: TPBiAβNB), 4-(3-biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: mTPBiAβNBi), 4-(4-biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4' '-phenyltriphenylamine (abbreviation: TPBiAβNBi), 4-phenyl-4'-(1-naphthyl)triphenylamine (abbreviation: αNBA1BP), 4,4'-bis(1-naphthyl)triphenylamine (abbreviation: αNBB1BP), 4,4'-diphenyl-4''-[4'-(carbazole-9-yl)biphenyl-4-yl]triphenylamine (abbreviation: YGTBi1BP), 4'-[4-(3-phenyl-9H-carbazole-9-yl)phenyl]tris(1, 1'-biphenyl-4-yl)amine (abbreviation: YGTBi1BP-02), 4-[4'-(carbazole-9-yl)biphenyl-4-yl]-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: YGTBiβNB), N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-N-[4-(1-naphthyl)phenyl]-9,9'-spirobio[9H-fluorene]-2-amine (abbreviation: PCBNBSF), N,N-bis([1,1'-bi Phenyl]-4-yl)-9,9'-spirobio[9H-fluorene]-2-amine (abbreviation: BBASF), N,N-bis([1,1'-biphenyl]-4-yl)-9,9'-spirobio[9H-fluorene]-4-amine (abbreviation: BBASF(4)), N-(1,1'-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobio[9H-fluorene]-4-amine (abbreviation: oFBiSF), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzofuran-4-amine (abbreviation: FrBiF), N-[4-(1-naphthyl)phenyl]-N-[3-(6-phenyldibenzofuran-4-yl)phenyl]-1-naphthylamine (abbreviation: mPDBfBNBN), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-phenyl-4' -[4-(9-phenylfluoren-9-yl)phenyl]triphenylamine (abbreviation: BPAFLBi), 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'- Di(1-naphthyl)-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBNBB), N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]spiro-9,9'-bifluoren-2-amine (abbreviation: PCBASF), N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF), N,N-bis(9 ,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio-9H-fluoren-4-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio-9H-fluoren-3-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio-9H-fluoren-2-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobio-9H-fluoren-1-amine, etc. can be used.

[0215] [Example of composite material composition 2] For example, a composite material containing an acceptor, a hole transporter, and an alkali metal fluoride or alkaline earth metal fluoride can be used as a hole injection material. In particular, a composite material in which fluorine atoms make up 20% or more of the atomic ratio can be suitably used. This can lower the refractive index of layer 104. Alternatively, a layer with a low refractive index can be formed inside the light-emitting device 550X. Alternatively, the external quantum efficiency of the light-emitting device 550X can be improved.

[0216] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0217] (Embodiment 4) In this embodiment, the configuration of a light-emitting device 550X according to one aspect of the present invention will be described with reference to Figure 1(A).

[0218] <Example configuration of the 550X light-emitting device> The light-emitting device 550X described in this embodiment includes an electrode 551X, an electrode 552X, a unit 103X, and a layer 105. Electrode 552X overlaps with electrode 551X, and unit 103X is sandwiched between electrodes 551X and 552X. Layer 105 is sandwiched between unit 103X and electrode 552X. For example, the configuration described in Embodiment 2 can be used for unit 103X.

[0219] <Example configuration of electrode 552X> For example, conductive materials can be used for electrode 552X. Specifically, materials containing metals, alloys, or conductive compounds can be used for electrode 552X in a single layer or in a multilayer structure.

[0220] For example, the material that can be used for electrode 551X described in Embodiment 3 can be used for electrode 552X. In particular, a material with a smaller work function than electrode 551X can be suitably used for electrode 552X. Specifically, a material with a work function of 3.8 eV or less is preferred.

[0221] For example, elements belonging to Group 1 of the periodic table, elements belonging to Group 2 of the periodic table, rare earth metals, and alloys containing these can be used for electrode 552X.

[0222] Specifically, lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), strontium (Sr), europium (Eu), ytterbium (Yb), and alloys containing these elements (MgAg, AlLi) can be used in electrode 552X.

[0223] Example of Layer 105 configuration For example, an electron-injection material can be used for layer 105. Layer 105 can also be referred to as an electron-injection layer.

[0224] Specifically, a donor material can be used in layer 105. Alternatively, a composite material of a donor material and an electron-transporting material can be used in layer 105. Alternatively, an electride can be used in layer 105. This makes it easier to inject electrons from electrode 552X, for example. Alternatively, not only materials with low work functions but also materials with high work functions can be used in electrode 552X. Alternatively, a material for electrode 552X can be selected from a wide range of materials, regardless of work function. Specifically, Al, Ag, ITO, silicon, or indium oxide-tin oxide containing silicon oxide can be used in electrode 552X. Alternatively, the driving voltage of the light-emitting device 550X can be reduced.

[0225] [Substances with donor properties] For example, alkali metals, alkaline earth metals, rare earth metals, or compounds thereof (oxides, halides, carbonates, etc.) can be used as donor substances. Alternatively, organic compounds such as tetratianaphthalene (abbreviated as TTN), nickerosene, and decamethylnickerosene can also be used as donor substances.

[0226] Examples of alkali metal compounds (including oxides, halides, and carbonates) that can be used include lithium oxide, lithium fluoride (LiF), cesium fluoride (CsF), lithium carbonate, cesium carbonate, 8-hydroxyquinolinatolithium (abbreviated as Liq), etc.

[0227] As alkaline earth metal compounds (including oxides, halides, and carbonates), calcium fluoride (CaF2), etc., can be used.

[0228] [Example of composite material composition 1] Furthermore, materials composed of multiple types of substances can be used as materials with electron injection properties. For example, a substance with donor properties and a material with electron transport properties can be used as a composite material.

[0229] [Materials with electron transport properties] For example, metal complexes or organic compounds having a π-electron-deficient heteroaromatic ring skeleton can be used in electron-transporting materials. For instance, an electron-transporting material that can be used in unit 103X described in Embodiment 2 can be used in the composite material.

[0230] [Example of composite material composition 2] Furthermore, a composite material can be made from a microcrystalline alkali metal fluoride and an electron-transporting material. Alternatively, a composite material can be made from a microcrystalline alkaline earth metal fluoride and an electron-transporting material. In particular, a composite material containing 50 wt% or more of alkali metal fluoride or alkaline earth metal fluoride can be suitably used. Alternatively, a composite material containing an organic compound having a bipyridine skeleton can be suitably used. This can lower the refractive index of layer 105, or improve the external quantum efficiency of the light-emitting device 550X.

[0231] [Example of composite material composition 3] For example, a composite material containing a first organic compound having lone pairs of electrons and a first metal can be used for layer 105. Furthermore, it is preferable that the sum of the number of electrons in the first organic compound and the first metal is odd. The molar ratio of the first metal to one mole of the first organic compound is preferably 0.1 to 10, more preferably 0.2 to 2, and even more preferably 0.2 to 0.8.

[0232] As a result, the first organic compound, which has lone pairs of electrons, can interact with the first metal to form a partially occupied molecular orbital (SOMO). Furthermore, when injecting electrons from electrode 552X into layer 105, the barrier between them can be reduced. Additionally, because the first metal has poor reactivity with water or oxygen, the moisture resistance of the light-emitting device 550X can be improved.

[0233] Furthermore, the spin density measured using electron spin resonance (ESR) is preferably 1 × 10⁻⁶. 16 spins / cm 3 The above is more comfortable 5x10 16 spins / cm 3 More preferably 1 × 10 17 spins / cm 3 The composite material described above can be used for layer 105.

[0234] [Organic compounds with lone pairs of electrons] For example, electron-transporting materials can be used in organic compounds containing lone pairs of electrons. For instance, compounds having electron-deficient heteroaromatic rings can be used. Specifically, compounds having at least one of a pyridine ring, a diazine ring (pyrimidine ring, pyrazine ring, pyridazine ring), or a triazine ring can be used. This allows for a reduction in the driving voltage of the light-emitting device 550X.

[0235] Furthermore, it is preferable that the LUMO level of the organic compound containing a lone pair of electrons is between -3.6 eV and -2.3 eV. In general, the HOMO and LUMO levels of the organic compound can be estimated by methods such as cyclic voltammetry (CV), photoelectron spectroscopy, optical absorption spectroscopy, and inverse photoelectron spectroscopy.

[0236] For example, 4,7-diphenyl-1,10-phenanthroline (abbreviated as BPhen), 2,9-di(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviated as NBPhen), diquinoxalino[2,3-a:2',3'-c]phenazine (abbreviated as HATNA), and 2,4,6-tris[3'-(pyridine-3-yl)biphenyl-3-yl]-1,3,5-triazine (abbreviated as TmPPPyTz) can be used in organic compounds containing lone pairs of electrons. NBPhen has a higher glass transition temperature (Tg) and superior heat resistance compared to BPhen.

[0237] Furthermore, copper phthalocyanine can be used, for example, in organic compounds that possess lone pairs of electrons. Note that copper phthalocyanine has an odd number of electrons.

[0238] [First Metal] For example, if the first organic compound having a lone pair of electrons has an even number of electrons, a composite material of the first metal and the first organic compound, which belong to an odd group in the periodic table, can be used for layer 105.

[0239] For example, manganese (Mn), a metal of Group 7; cobalt (Co), a metal of Group 9; copper (Cu), silver (Ag), and gold (Au), metals of Group 11; and aluminum (Al) and indium (In), metals of Group 13, are all odd-numbered groups in the periodic table. Furthermore, elements of Group 11 have lower melting points compared to elements of Group 7 or 9, making them suitable for vacuum deposition. In particular, silver (Ag) is preferred due to its low melting point.

[0240] Furthermore, by using Ag in the electrode 552X and layer 105, the adhesion between layer 105 and electrode 552X can be improved.

[0241] Furthermore, if the number of electrons in the first organic compound, which has a lone pair of electrons, is odd, a composite material of the first metal and the first organic compound, which belong to an even group in the periodic table, can be used for layer 105. For example, iron (Fe), a metal in group 8, belongs to an even group in the periodic table.

[0242] [Electride] For example, a material obtained by adding a high concentration of electrons to a mixed oxide of calcium and aluminum can be used as an electron-injection material.

[0243] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0244] (Embodiment 5) In this embodiment, the configuration of a light-emitting device 550X according to one aspect of the present invention will be described with reference to Figure 2(A).

[0245] Figure 2(A) is a cross-sectional view illustrating the configuration of a light-emitting device according to one embodiment of the present invention.

[0246] <Example configuration of the 550X light-emitting device> Furthermore, the light-emitting device 550X described in this embodiment includes an electrode 551X, an electrode 552X, a unit 103X, and a layer 106 (see Figure 2(A)). Electrode 552X overlaps with electrode 551X, and unit 103X is sandwiched between electrodes 551X and 552X. Layer 106 is sandwiched between electrode 552X and unit 103X.

[0247] 《Example of Layer 106 Configuration 1》 Layer 106 has the function of supplying electrons to the anode side and holes to the cathode side when a voltage is applied. Layer 106 can also be called a charge generation layer.

[0248] For example, a hole-injectable material that can be used in layer 104 as described in Embodiment 3 can be used in layer 106. Specifically, a composite material can be used in layer 106.

[0249] Furthermore, for example, a laminated film obtained by laminating a film containing the composite material with a film containing a hole-transporting material can be used for layer 106.

[0250] 《Example of Layer 106 Configuration 2》 Layer 106 comprises layer 106_1 and layer 106_2. Layer 106_2 is sandwiched between layer 106_1 and electrode 552X.

[0251] 《Example of Layer 106_1 Configuration》 For example, an electron-transporting material can be used for layer 106_1. Layer 106_1 can also be called an electron relay layer. Using layer 106_1 allows the layer in contact with the anode side of layer 106_1 to be separated from the layer in contact with the cathode side of layer 106_1. This reduces the interaction between the layer in contact with the anode side of layer 106_1 and the layer in contact with the cathode side of layer 106_1. Electrons can be smoothly supplied to the layer in contact with the anode side of layer 106_1.

[0252] A material having a LUMO level between the LUMO level of an acceptor material contained in the layer in contact with the anode side of layer 106_1 and the LUMO level of a material contained in the layer in contact with the cathode side of layer 106_1 can be suitably used in layer 106_1.

[0253] For example, a material having a LUMO level in the range of -5.0 eV or higher, preferably -5.0 eV to -3.0 eV, can be used for layer 106_1.

[0254] Specifically, phthalocyanine-based materials can be used in layer 106_1. Alternatively, metal complexes having metal-oxygen bonds and aromatic ligands can be used in layer 106_1.

[0255] Example of layer 106_2 configuration For example, a hole-injectable material that can be used in layer 104 as described in Embodiment 3 can be used in layer 106_2. Specifically, a composite material can be used in layer 106_2.

[0256] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0257] (Embodiment 6) In this embodiment, the configuration of a light-emitting device 550X according to one aspect of the present invention will be described with reference to Figure 2(B).

[0258] Figure 2(B) is a cross-sectional view illustrating the configuration of a light-emitting device according to one embodiment of the present invention, which has a configuration different from that shown in Figure 2(A).

[0259] <Example configuration of the 550X light-emitting device> The light-emitting device 550X described in this embodiment includes an electrode 551X, an electrode 552X, a unit 103X, a layer 106, and a unit 103X2 (see Figure 2(B)).

[0260] Unit 103X is sandwiched between electrodes 552X and 551X, and layer 106 is sandwiched between electrodes 552X and unit 103X.

[0261] Unit 103X2 is sandwiched between electrode 552X and layer 106. Unit 103X2 also has the function of emitting light ELX2.

[0262] Furthermore, the light-emitting device 550X has a layer 105_2, which is sandwiched between layer 106 and unit 103X.

[0263] In other words, the light-emitting device 550X has multiple stacked units between electrodes 551X and 552X. The number of stacked units is not limited to two; three or more units can be stacked. A configuration comprising multiple stacked units sandwiched between electrodes 551X and 552X, and a layer 106 sandwiched between the multiple units, is sometimes referred to as a stacked light-emitting device or a tandem light-emitting device.

[0264] This allows for high-brightness light emission while maintaining a low current density. Alternatively, reliability can be improved. Alternatively, the drive voltage can be reduced when comparing at the same brightness. Alternatively, power consumption can be suppressed.

[0265] 《Example Configuration of Unit 103X2》 Unit 103X2 comprises layers 111X2, 112_2, and 113_2. Layer 111X2 is sandwiched between layers 112_2 and 113_2.

[0266] The configuration used in unit 103X can also be used in unit 103X2. For example, the same configuration as unit 103X can be used in unit 103X2.

[0267] 《Example Configuration of Unit 103X2 2》 Furthermore, a different configuration from that of unit 103X can be used for unit 103X2. For example, a configuration that emits light with a different hue than the emitted color of unit 103X can be used for unit 103X2.

[0268] Specifically, a unit 103X that emits red and green light and a unit 103X2 that emits blue light can be stacked and used. This makes it possible to provide a light-emitting device that emits light of a desired color. For example, a light-emitting device that emits white light can be provided.

[0269] Example of Layer 106 configuration Layer 106 has the function of supplying electrons to one of unit 103X or unit 103X2 and holes to the other. For example, the layer 106 described in Embodiment 5 can be used.

[0270] 《Example of Layer 105_2 Configuration》 Layer 105_2 contains an electron-injection material. Layer 105_2 can also be referred to as the electron-injection layer. For example, the material that can be used for layer 105, as described in Embodiment 4, can be used for layer 105_2.

[0271] <Method for fabricating the 550X light-emitting device> For example, the electrodes 551X, 552X, unit 103X, layer 106, and unit 103X2 can be formed using dry, wet, vapor deposition, droplet ejection, coating, or printing methods. Furthermore, different methods can be used to form each component.

[0272] Specifically, the light-emitting device 550X can be manufactured using vacuum deposition equipment, inkjet equipment, spin coaters, coating equipment, gravure printing equipment, offset printing equipment, screen printing equipment, and the like.

[0273] For example, electrodes can be formed using a wet method or a sol-gel method with a paste of a metallic material. Furthermore, an indium oxide-zinc oxide film can be formed by sputtering using a target containing 1 wt% to 20 wt% zinc oxide relative to indium oxide. Additionally, an indium oxide (IWZO) film containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5 wt% to 5 wt% tungsten oxide and 0.1 wt% to 1 wt% zinc oxide relative to indium oxide.

[0274] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0275] (Embodiment 7) In this embodiment, the configuration of a display device 700 according to one aspect of the present invention will be described with reference to Figures 3(A) and 3(B).

[0276] Figure 3(A) is a cross-sectional view illustrating the configuration of a display device 700 according to one embodiment of the present invention, and Figure 3(B) is a cross-sectional view illustrating the configuration of a display device 700 according to a different embodiment of the present invention from Figure 3(A).

[0277] In this specification, devices fabricated using a metal mask or FMM (Fine Metal Mask, a high-resolution metal mask) may be referred to as MM (Metal Mask) structured devices. In addition, in this specification, devices fabricated without using a metal mask or FMM may be referred to as MML (Metal Maskless) structured devices.

[0278] In fabrication methods using fine metal masks, it is difficult to reduce the spacing between adjacent light-emitting devices to, for example, less than 10 μm. In fabrication methods using photolithography on a glass substrate, the spacing between adjacent light-emitting devices can be reduced to, for example, less than 10 μm, 5 μm or less, 3 μm or less, 2 μm or less, 1.5 μm or less, 1 μm or less, or 0.5 μm or less. Furthermore, in fabrication methods using photolithography on a silicon wafer, for example, using an exposure system for LSIs, the spacing between adjacent light-emitting devices can be reduced to 500 nm or less, 200 nm or less, 100 nm or less, and even 50 nm or less.

[0279] This significantly reduces the area of ​​the non-emitting region between adjacent light-emitting devices. It also makes it possible to bring the aperture ratio closer to 100%. For example, in a display device according to one aspect of the present invention, the aperture ratio can be 40% or more, 50% or more, 60% or more, 70% or more, 80% or more, and even 90% or more, while still being less than 100%.

[0280] <Example of display device 700 configuration 1> The display device 700 described in this embodiment has a light-emitting device 550X(i,j) and a light-emitting device 550Y(i,j) (see Figure 3(A)). The light-emitting device 550Y(i,j) is adjacent to the light-emitting device 550X(i,j).

[0281] Furthermore, the display device 700 has an insulating film 521, and the light-emitting devices 550X(i,j) and 550Y(i,j) are formed on the insulating film 521.

[0282] 《Example configuration of the light-emitting device 550X(i,j)》 The light-emitting device 550X(i,j) has an electrode 551X(i,j), an electrode 552X(i,j), and a unit 103X(i,j). It also has layers 104 and 105.

[0283] For example, the light-emitting devices described in Embodiments 2 to 6 can be used in the light-emitting device 550X(i,j). Specifically, the configuration that can be used for electrode 551X can be used for electrode 551X(i,j). Also, the configuration that can be used for unit 103X can be used for unit 103X(i,j). Furthermore, the configuration that can be used for layer 104 can be used for layer 104 of the light-emitting device 550X(i,j), and the configuration that can be used for layer 105 can be used for layer 105 of the light-emitting device 550X(i,j).

[0284] 《Example Configuration 1 of Light-Emitting Device 550Y(i,j)》 The light-emitting device 550Y(i,j) described in this embodiment has an electrode 551Y(i,j), an electrode 552Y(i,j), and a unit 103Y(i,j) (see Figure 3(A)). Electrode 552Y(i,j) overlaps with electrode 551Y(i,j), and unit 103Y(i,j) is sandwiched between electrodes 551Y(i,j) and 552Y(i,j).

[0285] Electrode 551Y(i,j) is adjacent to electrode 551X(i,j), and electrode 551Y(i,j) has a gap 551XY(i,j) between it and electrode 551X(i,j).

[0286] Furthermore, for example, a material that can be used for electrode 551X(i,j) can also be used for electrode 551Y(i,j). The potential supplied to electrode 551Y(i,j) may be the same as or different from that supplied to electrode 551X(i,j). By supplying a different potential, the light-emitting device 550Y(i,j) can be driven under different conditions than the light-emitting device 550X(i,j).

[0287] 《Example Configuration of Unit 103Y(i,j) 1》 Unit 103Y(i,j) comprises a single-layer structure or a multi-layer structure. For example, unit 103Y(i,j) comprises layer 111Y(i,j), layer 112, and layer 113 (see Figure 3(A)). Layer 111Y(i,j) is sandwiched between layers 112 and 113, layer 112 is sandwiched between electrode 551Y(i,j) and layer 111Y(i,j), and layer 113 is sandwiched between electrode 552Y(i,j) and layer 111Y(i,j).

[0288] For example, a layer selected from functional layers such as an emissive layer, a hole transport layer, an electron transport layer, and a carrier block layer can be used in unit 103Y(i,j). Furthermore, a layer selected from functional layers such as a hole injection layer, an electron injection layer, an exciton block layer, and a charge generation layer can also be used in unit 103Y(i,j).

[0289] 《Example Configuration 2 of Light-Emitting Device 550Y(i,j)》 Furthermore, the light-emitting device 550Y(i,j) has layer 104 and layer 105. Layer 104 is sandwiched between electrode 551Y(i,j) and unit 103Y(i,j), and layer 105 is sandwiched between unit 103Y(i,j) and electrode 552Y(i,j).

[0290] Furthermore, some of the components of the light-emitting device 550X(i,j) can be used in some of the components of the light-emitting device 550Y(i,j). This allows for the commonality of some components and simplifies the manufacturing process.

[0291] <Example configuration of display device 700 2> Furthermore, the display device 700 described in this embodiment has an insulating film 528 (see Figure 3(A)).

[0292] 《Example of the configuration of insulating film 528》 The insulating film 528 has an opening, one of which overlaps with electrode 551X(i,j), and the other opening overlaps with electrode 551Y(i,j).

[0293] <Example configuration of display device 700 3> The display device 700 described in this embodiment includes a light-emitting device 550X(i,j) and a light-emitting device 550Y(i,j), where the light-emitting device 550Y(i,j) is adjacent to the light-emitting device 550X(i,j) (see Figure 3(B)).

[0294] The light-emitting device 550X(i,j) includes electrodes 551X(i,j), 552X(i,j), and unit 103X(i,j). It also includes layers 104X(i,j) and 105, and the configuration that can be used for layer 104 can be used for layer 104X(i,j).

[0295] The light-emitting device 550Y(i,j) includes an electrode 551Y(i,j), an electrode 552Y(i,j), and a unit 103Y(i,j). It also includes layers 104Y(i,j) and 105, and electrode 551Y(i,j) has a gap 551XY(i,j) between it and electrode 551X(i,j).

[0296] Layer 104Y(i,j) is sandwiched between electrodes 551Y(i,j) and 552Y(i,j), and is in contact with electrode 551Y(i,j). Layer 104Y(i,j) contains a material that has hole-injection properties. Furthermore, layer 104Y(i,j) has a gap 104XY(i,j) between it and layer 104X(i,j), and the gap 104XY(i,j) overlaps with the gap 551XY(i,j).

[0297] Furthermore, the light-emitting device 550Y(i,j) includes unit 103Y(i,j), and unit 103Y(i,j) has a gap between it and the light-emitting device 550X(i,j).

[0298] The differences between this device and the display device 700 described using Figure 3(A) are that layer 104Y(i,j) has a gap 104XY(i,j) between it and layer 104X(i,j), and in the configuration of unit 103Y(i,j), layer 112Y(i,j) has a gap between it and layer 112X(i,j), and layer 113Y(i,j) has a gap between it and layer 113X(i,j). Here, the differences will be explained in detail, and the above explanation will be used as a reference for similar configurations.

[0299] Example of layer 104Y(i,j) configuration A material with hole-injection properties can be used in layer 104Y(i,j). Furthermore, layer 104Y(i,j) can be referred to as a hole-injection layer. For example, a configuration that can be used in layer 104 can be used in layer 104Y(i,j). Specifically, 1 × 10 4 [Ω cm] or more 1×10 7 A film having a resistivity of [Ω·cm] or less can be used for layer 104Y(i,j). Preferably, layer 104Y(i,j) is 5 × 10 4 [Ω cm] or more 1×10 7 Having a resistivity of [Ω·cm] or less, more preferably 1 × 10⁻⁶ 5 [Ω cm] or more 1×10 7 It has a resistivity of [Ω·cm] or less.

[0300] Furthermore, layer 104Y(i,j) has a gap 104XY(i,j) between it and layer 104X(i,j). This makes it possible to drastically suppress the current flowing between layer 104Y(i,j) and layer 104X(i,j). It also suppresses the crosstalk phenomenon, which causes adjacent light-emitting devices to operate unintentionally. In addition, it is possible to provide a display device 700 in which the occurrence of crosstalk is suppressed.

[0301] 《Example 3 of Unit 103Y(i,j) Configuration》 Unit 103Y(i,j) comprises layers 111Y(i,j), 112Y(i,j), and 113Y(i,j) (see Figure 3(B)).

[0302] Layer 111Y(i,j) is sandwiched between layers 112Y(i,j) and 113Y(i,j), and layer 111Y(i,j) has a gap between it and layer 111X(i,j).

[0303] Layer 112Y(i,j) is sandwiched between layer 111Y(i,j) and electrode 551Y(i,j), and layer 112Y(i,j) has a gap between it and layer 112X(i,j).

[0304] Layer 113Y(i,j) is sandwiched between layer 111Y(i,j) and electrode 552Y(i,j), and layer 113Y(i,j) has a gap between it and layer 113X(i,j).

[0305] In other words, unit 103Y(i,j) has a groove between it and unit 103X(i,j), and unit 103Y(i,j) has one side wall along the groove. Unit 103X(i,j) also has another side wall along the groove, and this other side wall faces the first side wall.

[0306] <Example configuration of display device 700 4> The display device 700 described in this embodiment has, for example, an insulating film 529XY(i,j) (see Figure 3(B)).

[0307] 《Example of the configuration of insulating film 529XY(i,j)》 The insulating film 529XY(i,j) comprises insulating film 529(1) and insulating film 529(2).

[0308] The insulating film 529(1) is sandwiched between the insulating film 529(2) and the insulating film 521, and the insulating film 529(1) is in contact with the insulating film 521. The insulating film 529(1) also includes a region in contact with the side wall of unit 103Y(i,j) and a region in contact with the side wall of unit 103X(i,j).

[0309] <Example configuration of display device 700 5> Furthermore, the display device 700 described in this embodiment includes a layer 111Y(i,j) (see Figure 3(A) or Figure 3(B)).

[0310] 《Example of layer 111Y(i,j) configuration 1》 For example, a luminescent material, or a luminescent material and a host material, can be used for layer 111Y(i,j). Layer 111Y(i,j) can also be referred to as the luminescent layer. It is preferable to position layer 111Y(i,j) in a region where holes and electrons recombine. This allows the energy generated by carrier recombination to be efficiently emitted as light. It is also preferable to position layer 111Y(i,j) away from metals used in electrodes, etc. This suppresses quenching caused by metals used in electrodes, etc.

[0311] For example, a different luminescent material can be used in layer 111Y(i,j) than the luminescent material used in layer 111X(i,j). Specifically, luminescent materials with different hues can be used in layer 111Y(i,j). This allows for the arrangement of luminescent devices with different hues. Alternatively, additive color mixing can be performed using multiple luminescent devices with different hues. Or, colors with hues that cannot be displayed by individual luminescent devices can be represented.

[0312] For example, a light-emitting device that emits blue light, a light-emitting device that emits green light, and a light-emitting device that emits red light can be placed in the display device 700. Alternatively, a light-emitting device that emits white light, a light-emitting device that emits yellow light, and a light-emitting device that emits infrared light can be placed in the display device 700.

[0313] 《Example of layer 111Y(i,j) configuration 2》 For example, fluorescent materials, phosphorescent materials, or TADF materials can be used as luminescent materials. This allows the energy generated by carrier recombination to be released from the luminescent material as photo-ELY (see Figure 3(A) or Figure 3(B)).

[0314] [Fluorescent material] For example, a fluorescent material that can be used in layer 111X can be used in layer 111Y(i,j). However, it is not limited to this, and various known fluorescent materials can be used in layer 111Y(i,j).

[0315] [Phosphorescent material] A phosphorescent material can be used in layer 111Y(i,j). For example, the phosphorescent materials exemplified below can be used in layer 111Y(i,j). However, this is not limited to these, and various known phosphorescent materials can be used in layer 111Y(i,j).

[0316] For example, organometallic iridium complexes having a 4H-triazole skeleton, organometallic iridium complexes having a 1H-triazole skeleton, organometallic iridium complexes having an imidazole skeleton, organometallic iridium complexes with a phenylpyridine derivative having an electron-withdrawing group as a ligand, organometallic iridium complexes having a pyrimidine skeleton, organometallic iridium complexes having a pyrazine skeleton, organometallic iridium complexes having a pyridine skeleton, rare earth metal complexes, platinum complexes, etc., can be used in layer 111Y(i,j).

[0317] [Phosphorescent material (blue)] Examples of organometallic iridium complexes having a 4H-triazole skeleton include tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazole-3-yl-κN2]phenyl-κC}iridium(III) (abbreviation: [Ir(mpptz-dmp)3]), tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Mptz)3]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPrptz-3b)3]), etc.

[0318] Examples of organometallic iridium complexes having a 1H-triazole skeleton include tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(Mptz1-mp)3]), tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Prptz1-Me)3]), etc.

[0319] Examples of organometallic iridium complexes having an imidazole skeleton include fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpmi)3]), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridine]iridium(III) (abbreviation: [Ir(dmpimpt-Me)3]), etc.

[0320] Examples of organometallic iridium complexes using phenylpyridine derivatives having electron-withdrawing groups as ligands include bis[2-(4',6'-difluorophenyl)pyridinate-N,C 2’ Iridium(III) tetrakis(1-pyrazolyl) borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridinate-N,C 2’Iridium(III) picolinate (abbreviation: Firpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinate-N,C 2’ Iridium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyridinate-N,C 2’ Iridium(III) acetylacetonate (abbreviated as FIracac), etc., can be used.

[0321] These compounds exhibit blue phosphorescence and have emission wavelength peaks between 440 nm and 520 nm.

[0322] [Phosphorescent material (green)] Examples of organometallic iridium complexes having a pyrimidine skeleton include tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)3]), tris(4-t-butyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonato)bis(6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [ Ir(tBuppm)2(acac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]), (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm)2(acac)]), (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)2(acac)]), etc. can be used.

[0323] Examples of organometallic iridium complexes having a pyrazine skeleton include (acetylacetonato)bis(3,5-dimethyl-2-phenylpyradinato)iridium(III) (abbreviation: [Ir(mppr-Me)2(acac)]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyradinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]), etc.

[0324] Examples of organometallic iridium complexes having a pyridine skeleton include tris(2-phenylpyridinato-N,C) 2’ Iridium(III) (abbreviation: [Ir(ppy)3]), bis(2-phenylpyridinate-N,C) 2’ Iridium(III) acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), bis(benzo[h]quinolinate)iridium(III) acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), tris(benzo[h]quinolinate)iridium(III) (abbreviation: [Ir(bzq)3]), tris(2-phenylquinolinate-N,C) 2’ Iridium(III) (abbreviation: [Ir(pq)3]), bis(2-phenylquinolinato-N,C) 2’ Iridium(III) acetylacetonate (abbreviation: [Ir(pq)2(acac)]), [2-d3-methyl-8-(2-pyridinyl-κN)benzofl[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridinyl-κN2)phenyl-κC]iridium(III) (abbreviation: [Ir(5mppy-d3)2(mbfpypy-d3)]), [2-d3-methyl-(2-pyridinyl-κN)benzofl[2,3-b]pyridine-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(ppy)2(mbfpypy-d3)]), etc. can be used.

[0325] Examples of rare earth metal complexes include tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [Tb(acac)3(Phen)]).

[0326] These compounds primarily exhibit green phosphorescence and have emission wavelength peaks between 500 nm and 600 nm. Furthermore, organometallic iridium complexes with a pyrimidine skeleton are remarkably superior in terms of reliability or luminescence efficiency.

[0327] [Phosphorescent material (red)] Examples of organometallic iridium complexes having a pyrimidine skeleton include (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinato](dipvaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)]), bis[4,6-di(naphthalene-1-yl)pyrimidinato](dipvaloylmethanato)iridium(III) (abbreviation: [Ir(d1npm)2(dpm)]), etc.

[0328] Examples of organometallic iridium complexes having a pyrazine skeleton include (acetylacetonato)bis(2,3,5-triphenylpyradinato)iridium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2,3,5-triphenylpyradinato)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(tppr)2(dpm)]), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq)2(acac)]), etc.

[0329] Examples of organometallic iridium complexes having a pyridine skeleton include tris(1-phenylisoquinolinato-N,C) 2’ Iridium(III) (abbreviation: [Ir(piq)3]), bis(1-phenylisoquinolinato-N,C) 2’ Iridium(III) acetylacetonate (abbreviation: [Ir(piq)2(acac)]), etc., can be used.

[0330] Examples of rare earth metal complexes that can be used include tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: [Eu(DBM)3(Phen)]), tris[1-(2-tenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: [Eu(TTA)3(Phen)]), etc.

[0331] Examples of platinum complexes that can be used include 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviated as PtOEP).

[0332] These compounds exhibit red phosphorescence and have an emission peak between 600 nm and 700 nm. Furthermore, organometallic iridium complexes with a pyrazine skeleton produce red emission with a chromaticity suitable for use in display devices.

[0333] [Substances exhibiting thermally activated delayed fluorescence (TADF)] For example, a TADF material that can be used for layer 111X can be used for layer 111Y(i,j). However, this is not limited to this, and various known TADF materials can be used for layer 111Y(i,j).

[0334] 《Example of layer 111Y(i,j) configuration 3》 Materials with carrier transport properties can be used as the host material. For example, materials with hole transport properties, materials with electron transport properties, TADF materials, materials with anthracene skeletons, and mixed materials can be used as the host material. For example, a host material that can be used in layer 111X can be used in layer 111Y(i,j). It is preferable to use a material with a larger band gap than the luminescent material contained in layer 111Y(i,j) as the host material. This makes it possible to suppress energy transfer from excitons generated in layer 111Y(i,j) to the host material.

[0335] [Materials with hole transport properties] The hole mobility is 1 × 10⁻⁶. -6 cm 2 Materials with a Vs of / Vs or higher can be suitably used as materials with hole transport properties.

[0336] For example, a hole-transporting material that can be used in layer 112 can be used in layer 111Y(i,j). Specifically, a hole-transporting material that can be used in a hole-transporting layer can be used in layer 111Y(i,j).

[0337] [Materials with electron transport properties] For example, metal complexes or organic compounds having a π-electron-deficient heteroaromatic ring skeleton can be used as electron-transporting materials.

[0338] For example, an electron-transporting material that can be used in layer 113 can be used in layer 111Y(i,j). Specifically, an electron-transporting material that can be used in an electron transport layer can be used in layer 111Y(i,j).

[0339] [Materials containing an anthracene skeleton] Organic compounds having an anthracene skeleton can be used as host materials. In particular, organic compounds having an anthracene skeleton are suitable when fluorescent materials are used as the light-emitting material. This makes it possible to realize light-emitting devices with good luminescence efficiency and durability. Furthermore, the organic compounds described in Embodiment 1 can be used as host materials.

[0340] Among organic compounds having an anthracene skeleton, organic compounds having a diphenylanthracene skeleton, particularly a 9,10-diphenylanthracene skeleton, are preferred because they are chemically stable. Furthermore, when the host material has a carbazole skeleton, it is preferred because the hole injection and transport properties are enhanced. In particular, when the host material contains a dibenzocarbazole skeleton, the HOMO level becomes about 0.1 eV shallower than that of carbazole, making it easier for holes to enter, and it is also preferred because it has excellent hole transport properties and high heat resistance. From the viewpoint of hole injection and transport properties, a benzofluorene skeleton or a dibenzofluorene skeleton may be used instead of a carbazole skeleton.

[0341] Therefore, substances having both a 9,10-diphenylanthracene skeleton and a carbazole skeleton, substances having both a 9,10-diphenylanthracene skeleton and a benzocarbazole skeleton, and substances having both a 9,10-diphenylanthracene skeleton and a dibenzocarbazole skeleton are preferred as host materials.

[0342] For example, 6-[3-(9,10-diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-{4-(9-phenyl-9H-fluoren-9-yl)biphenyl-4'-yl}anthracene (abbreviation: FLPPA), 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth), 9-phenyl-3-[4-(10-phenyl [Lu-9-anthryl)phenyl]-9H-carbazole (abbreviated as PCzPA), 9-[4-(10-phenyl-9-antracenyl)phenyl]-9H-carbazole (abbreviated as CzPA), 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated as cgDBCzPA), 3-[4-(1-naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviated as PCPN), etc. can be used.

[0343] In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA exhibit very good characteristics.

[0344] [Substances exhibiting thermally activated delayed fluorescence (TADF)] TADF materials can be used as host materials. When TADF materials are used as host materials, the triplet excitation energy generated by the TADF material can be converted into singlet excitation energy through reverse intersystem crossing. Furthermore, the excitation energy can be transferred to the light-emitting material. In other words, the TADF material functions as an energy donor, and the light-emitting material functions as an energy acceptor. This can increase the luminescence efficiency of the light-emitting device.

[0345] This is particularly effective when the light-emitting material is a fluorescent material. Furthermore, in order to obtain high luminescence efficiency, it is preferable that the S1 level of the TADF material is higher than that of the fluorescent material. Also, it is preferable that the T1 level of the TADF material is higher than that of the fluorescent material. Therefore, it is preferable that the T1 level of the TADF material is higher than that of the fluorescent material.

[0346] Furthermore, it is preferable to use a TADF material that exhibits emission that overlaps with the wavelength of the lowest-energy absorption band of the fluorescent material. This is preferable because it allows for smooth transfer of excitation energy from the TADF material to the fluorescent material, resulting in efficient emission.

[0347] Furthermore, for singlet excitation energy to be efficiently generated from triplet excitation energy by reverse intersystem crossing, it is preferable that carrier recombination occurs in the TADF material. It is also preferable that the triplet excitation energy generated in the TADF material does not transfer to the triplet excitation energy of the fluorescent substance. To achieve this, it is preferable that the fluorescent substance has protecting groups around the luminescent phosphoform (the skeleton that causes luminescence). Preferred protecting groups are substituents without π bonds, and saturated hydrocarbons are preferred. Specifically, examples include alkyl groups having 3 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 carbon atoms, and trialkylsilyl groups having 3 to 10 carbon atoms. It is even more preferable to have multiple protecting groups. Substituents without π bonds have poor carrier transport function, and therefore can increase the distance between the TADF material and the luminescent phosphoform of the fluorescent substance with little effect on carrier transport or carrier recombination.

[0348] Here, the term "luminescent phosphat" refers to the group of atoms (skeleton) that causes light emission in a fluorescent material. The luminescent phosphat preferably has a skeleton with π bonds, preferably contains an aromatic ring, and preferably has a fused aromatic ring or a fused heteroaromatic ring.

[0349] Examples of condensed aromatic rings or condensed heteroaromatic rings include phenanthrene skeletons, stilbene skeletons, acridone skeletons, phenoxazine skeletons, and phenothiazine skeletons. In particular, fluorescent materials having naphthalene skeletons, anthracene skeletons, fluorene skeletons, chrysene skeletons, triphenylene skeletons, tetracene skeletons, pyrene skeletons, perylene skeletons, coumarin skeletons, quinacridone skeletons, and naphthobisbenzofuran skeletons are preferred because they have high fluorescence quantum yields.

[0350] For example, TADF material, which can be used as a luminescent material, can be used as a host material.

[0351] [Example of mixed material composition 1] Furthermore, a material composed of a mixture of multiple substances can be used as the host material. For example, a material with electron-transporting properties and a material with hole-transporting properties can be used in the mixture. The weight ratio of the material with hole-transporting properties to the material with electron-transporting properties in the mixture should be such that the ratio of the material with hole-transporting properties to the material with electron-transporting properties is between 1 / 19 and 19 / 1. This allows for easy adjustment of the carrier transport properties of layer 111Y(i,j). In addition, the recombination region can be easily controlled.

[0352] [Example of mixed material composition 2] Materials mixed with phosphorescent substances can be used as host materials. Phosphorescent substances can also be used as energy donors to supply excitation energy to fluorescent substances when fluorescent substances are used as the light-emitting material.

[0353] A mixed material containing a material that forms an excited complex can be used as the host material. For example, a material in which the emission spectrum of the formed excited complex overlaps with the wavelength of the lowest-energy absorption band of the luminescent substance can be used as the host material. This allows for smoother energy transfer and improved luminescence efficiency, or it can suppress the driving voltage.

[0354] A phosphorescent material can be used in at least one of the materials forming the excitation complex. This allows for the utilization of reverse intersystem crossing. Alternatively, the triplet excitation energy can be efficiently converted to the singlet excitation energy.

[0355] For a combination of materials to form an excited complex, it is preferable that the HOMO level of the hole-transporting material is higher than or equal to the HOMO level of the electron-transporting material. Alternatively, it is preferable that the LUMO level of the hole-transporting material is higher than or equal to the LUMO level of the electron-transporting material. This allows for efficient formation of the excited complex. The LUMO and HOMO levels of the materials can be derived from their electrochemical properties (reduction potential and oxidation potential). Specifically, the reduction potential and oxidation potential can be measured using cyclic voltammetry (CV) measurement.

[0356] The formation of excited complexes can be confirmed, for example, by comparing the emission spectra of a hole-transporting material, an electron-transporting material, and a mixed film made by mixing these materials, and observing that the emission spectrum of the mixed film shifts to a longer wavelength than the emission spectra of each individual material (or has a new peak on the longer wavelength side). Alternatively, it can be confirmed by comparing the transient photoluminescence (PL) of a hole-transporting material, the transient PL of an electron-transporting material, and the transient PL of a mixed film made by mixing these materials, and observing differences in the transient response, such as the transient PL lifetime of the mixed film having a longer lifetime component or a larger proportion of the delayed component than the transient PL lifetime of each individual material. Furthermore, the transient PL mentioned above can be replaced with transient electroluminescence (EL). That is, the formation of excited complexes can also be confirmed by comparing the transient EL of a hole-transporting material, the transient EL of an electron-transporting material, and the transient EL of a mixed film made by mixing these materials, and observing the differences in the transient response.

[0357] 《Example of layer 112Y(i,j) configuration》 For example, a hole-transporting material can be used in layer 112Y(i,j). Layer 112Y(i,j) can also be referred to as a hole-transporting layer. It is preferable to use a material in layer 112Y(i,j) that has a larger band gap than the luminescent material contained in layer 111Y(i,j). This suppresses energy transfer from excitons generated in layer 111Y(i,j) to layer 112Y(i,j). Furthermore, the configuration used for layer 112 described in Embodiment 2 can also be used for layer 112Y(i,j).

[0358] 《Example of layer 113Y(i,j) configuration》 For example, electron-transporting materials, materials with an anthracene skeleton, and mixed materials can be used in layer 113Y(i,j). Furthermore, layer 113Y(i,j) can be referred to as an electron transport layer. It is preferable to use a material with a larger band gap than the luminescent material contained in layer 111Y(i,j) in layer 113Y(i,j). This suppresses energy transfer from excitons generated in layer 111Y(i,j) to layer 113Y(i,j). The configurations that can be used for layer 113, as described in Embodiment 2, can also be used for layer 113Y(i,j).

[0359] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0360] (Embodiment 8) In this embodiment, the configuration of a display device 700 according to one aspect of the present invention will be described with reference to Figures 4(A) and 4(B).

[0361] Figure 4(A) is a cross-sectional view illustrating the configuration of a display device 700 according to one embodiment of the present invention, and Figure 4(B) is a cross-sectional view illustrating the configuration of a display device 700 according to a different embodiment of the present invention from Figure 4(A).

[0362] <Example of display device 700 configuration 1> The display device 700 described in this embodiment includes a light-emitting device 550X(i,j) and a photoelectric conversion device 550S(i,j) (see Figure 4(A)). The photoelectric conversion device 550S(i,j) is adjacent to the light-emitting device 550X(i,j).

[0363] Furthermore, the display device 700 has an insulating film 521, and the light-emitting device 550X(i,j) and the photoelectric conversion device 550S(i,j) are formed on the insulating film 521.

[0364] 《Example configuration of the light-emitting device 550X(i,j)》 The light-emitting device 550X(i,j) has an electrode 551X(i,j), an electrode 552X(i,j), and a unit 103X(i,j). It also has layers 104 and 105.

[0365] For example, the light-emitting devices described in Embodiments 2 to 6 can be used in the light-emitting device 550X(i,j). Specifically, the configuration that can be used in electrode 551X can be used in electrode 551X(i,j). Also, the configuration that can be used in unit 103X can be used in unit 103X(i,j). Furthermore, the configuration that can be used in layer 104 can be used in layer 104, and the configuration that can be used in layer 105 can be used in layer 105.

[0366] 《Example Configuration 1 of Photoelectric Conversion Device 550S(i,j)》 The photoelectric conversion device 550S(i,j) includes an electrode 551S(i,j), an electrode 552S(i,j), and a unit 103S(i,j). Electrode 552S(i,j) overlaps with electrode 551S(i,j), and unit 103S(i,j) is sandwiched between electrodes 552S(i,j) and 551S(i,j).

[0367] Electrode 551S(i,j) is sandwiched between unit 103S(i,j) and insulating film 521, and electrode 551S(i,j) has a gap 551XS(i,j) between it and electrode 551X(i,j).

[0368] 《Example Configuration of Unit 103S(i,j) 1》 Unit 103S(i,j) absorbs light hv and supplies electrons to one electrode and holes to the other electrode. For example, unit 103S(i,j) supplies holes to electrode 551S(i,j) and electrons to electrode 552S(i,j).

[0369] Unit 103S(i,j) has a single-layer structure or a multi-layer structure. For example, unit 103S(i,j) comprises layer 114S(i,j), layer 112, and layer 113 (see Figure 4(A)). Layer 114S(i,j) is sandwiched between layers 112 and 113, layer 112 is sandwiched between electrode 551S(i,j) and layer 114S(i,j), and layer 113 is sandwiched between electrode 552S(i,j) and layer 114S(i,j).

[0370] For example, a layer selected from functional layers such as a photoelectric conversion layer, a hole transport layer, an electron transport layer, and a carrier block layer can be used in unit 103S.

[0371] 《Example of layer 114S(i,j) configuration 1》 Layer 114S(i,j) can be called a photoelectric conversion layer. Layer 114S(i,j) absorbs light hv and supplies electrons to the layer adjacent to it and holes to the layer adjacent to it. For example, layer 114S(i,j) supplies holes to layer 112 and electrons to layer 113. For example, materials that can be used in organic solar cells can be used in layer 114S(i,j). Specifically, electron-accepting materials and electron-donating materials can be used in layer 114S(i,j).

[0372] [Examples of electron-accepting materials] For example, fullerene derivatives, non-fullerene electron acceptors, etc., can be used as electron-accepting materials.

[0373] Examples of electron-accepting materials include C 60 Fullerene, C 70 Fullerene, [6,6]-phenyl-C 71-Methyl butyrate (abbreviation: PC71BM), [6,6]-phenyl-C 61 -Methyl butyrate (abbreviation: PC61BM), 1',1'',4',4''-tetrahydro-di[1,4]methanonaphthaleno[1,2:2',3',56,60:2'',3''][5,6]fullerene-C 60 (Abbreviation: ICBA) etc. can be used.

[0374] Furthermore, non-fullerene electron acceptors can include, for example, perylene derivatives, compounds having a dicyanomethyleneindanone group, etc. N,N'-dimethyl-3,4,9,10-perylenetetracarboxylic acid diimide (abbreviated as Me-PTCDI), etc.

[0375] [Examples of electron-donating materials] For example, phthalocyanine compounds, tetracene derivatives, quinacridone derivatives, rubrene derivatives, etc., can be used as electron-donating materials.

[0376] Examples of electron-donating materials include copper(II) phthalocyanine (abbreviated as CuPc), tin(II) phthalocyanine (abbreviated as SnPc), zinc phthalocyanine (abbreviated as ZnPc), tetraphenyldibenzoperifuranthene (abbreviated as DBP), rubrene, and others.

[0377] 《Example of layer 114S(i,j) configuration 2》 For example, a single-layer structure or a multi-layer structure can be used for layer 114S(i,j). Specifically, a bulk heterojunction type structure can be used for layer 114S(i,j). Alternatively, a heterojunction type structure can be used for layer 114S(i,j).

[0378] [Example of mixed material composition] For example, a mixed material containing electron-accepting and electron-donating materials can be used in layer 114S(i,j) (see Figure 4(A)). A configuration in which a mixed material containing electron-accepting and electron-donating materials is used in layer 114S(i,j) can be called a bulk heterojunction type.

[0379] Specifically, C 70 A mixed material containing fullerene and DBP can be used in layer 114S(i,j).

[0380] [Example of heterozygous type] Layers 114N(i,j) and 114P(i,j) can be used as layer 114S(i,j) (see Figure 4(B)). Layer 114N(i,j) is sandwiched between one electrode and layer 114P(i,j), and layer 114P(i,j) is sandwiched between layer 114N(i,j) and the other electrode. For example, layer 114N(i,j) is sandwiched between electrode 552S(i,j) and layer 114P(i,j), and layer 114P(i,j) is sandwiched between layer 114N(i,j) and electrode 551S(i,j).

[0381] n-type semiconductors can be used in layer 114N(i,j). For example, Me-PTCDI can be used in layer 114N(i,j).

[0382] Furthermore, a p-type semiconductor can be used in layer 114P(i,j). For example, rubrene can be used in layer 114P(i,j).

[0383] Furthermore, a photoelectric conversion device 550S(i,j) having a configuration in which layer 114P(i,j) is in contact with layer 114N(i,j) can be called a PN junction type photodiode.

[0384] This embodiment can be appropriately combined with other embodiments shown in this specification.

[0385] (Embodiment 9) This embodiment describes a light-emitting device using a light-emitting device described in any one of Embodiments 2 to 6.

[0386] In this embodiment, a light-emitting device manufactured using the light-emitting device described in any one of Embodiments 2 to 6 will be described with reference to Figure 5. Figure 5(A) is a top view showing the light-emitting device, and Figure 5(B) is a cross-sectional view obtained by cutting Figure 5(A) along A and C. This light-emitting device has a pixel section 602 and a drive circuit section, indicated by dotted lines, which control the light emission of the light-emitting device. The drive circuit section includes a source line drive circuit 601 and a gate line drive circuit 603. The light-emitting device also includes a sealing substrate 604 and a sealing material 605, with the sealing material 605 surrounding a space 607.

[0387] The routing wiring 608 is for transmitting signals input to the source line drive circuit 601 and the gate line drive circuit 603, and receives video signals, clock signals, start signals, reset signals, etc. from the FPC (flexible printed circuit) which serves as the external input terminal 609. Although only the FPC is shown in the diagram, a printed circuit board (PWB) may be attached to this FPC. In this specification, the light-emitting device includes not only the light-emitting device itself, but also the state in which the FPC or PWB is attached to it.

[0388] Next, the cross-sectional structure will be explained using Figure 5(B). A drive circuit section and a pixel section are formed on the element substrate 610, and here, the source line drive circuit 601, which is the drive circuit section, and one pixel in the pixel section 602 are shown.

[0389] The element substrate 610 may be manufactured using a substrate made of glass, quartz, organic resin, metal, alloy, semiconductor, or other materials, as well as a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (Polyvinyl Fluoride), polyester, or acrylic resin.

[0390] The structure of the transistor used in the pixel or driving circuit is not particularly limited. For example, it may be an inverse staggered transistor or a staggered transistor. It may also be a top-gate or bottom-gate transistor. The semiconductor material used for the transistor is not particularly limited; for example, silicon, germanium, silicon carbide, gallium nitride, etc., can be used. Alternatively, an oxide semiconductor containing at least one of indium, gallium, and zinc, such as an In-Ga-Zn metal oxide, may be used.

[0391] The crystallinity of the semiconductor material used in the transistor is not particularly limited; amorphous semiconductors, crystalline semiconductors (microcrystalline semiconductors, polycrystalline semiconductors, single-crystal semiconductors, or semiconductors having a crystalline region in part) may be used. Using a crystalline semiconductor is preferable because it can suppress the degradation of transistor characteristics.

[0392] Here, it is preferable to use oxide semiconductors for semiconductor devices such as transistors used in the pixels or driving circuits described above, as well as transistors used in touch sensors and the like, which will be described later. In particular, it is preferable to use oxide semiconductors with a wider bandgap than silicon. By using oxide semiconductors with a wider bandgap than silicon, the current in the off state of the transistor can be reduced.

[0393] The above oxide semiconductor preferably contains at least indium (In) or zinc (Zn). More preferably, it is an oxide semiconductor containing an oxide represented as an In-M-Zn oxide (where M is a metal such as Al, Ti, Ga, Ge, Y, Zr, Sn, La, Ce, or Hf).

[0394] In particular, it is preferable to use an oxide semiconductor film as the semiconductor layer, which has multiple crystalline portions, the c-axis of which is oriented perpendicular to the surface on which the semiconductor layer is formed or to the upper surface of the semiconductor layer, and which does not have grain boundaries between adjacent crystalline portions.

[0395] By using such materials as semiconductor layers, fluctuations in electrical properties can be suppressed, enabling the realization of highly reliable transistors.

[0396] Furthermore, due to its low off-current, the transistor having the aforementioned semiconductor layer can retain the charge stored in the capacitor via the transistor for a long period of time. By applying such transistors to pixels, it becomes possible to maintain the gradation of the image displayed in each display area while simultaneously stopping the drive circuit. As a result, electronic devices with extremely reduced power consumption can be realized.

[0397] It is preferable to provide an undercoat to stabilize the characteristics of the transistor. As the undercoat, an inorganic insulating film such as a silicon oxide film, silicon nitride film, silicon oxynitride film, or silicon nitride film can be used and fabricated as a single layer or in layers. The undercoat can be formed using sputtering, CVD (Chemical Vapor Deposition) (plasma CVD, thermal CVD, MOCVD (Metal Organic CVD), etc.), ALD (Atomic Layer Deposition), coating, printing, etc. Note that the undercoat may be omitted if not necessary.

[0398] Note that FET623 is one of the transistors formed in the source line drive circuit 601. The drive circuit can be formed using various CMOS, PMOS, or NMOS circuits. In this embodiment, a driver-integrated type with the drive circuit formed on the substrate is shown, but this is not necessarily required, and the drive circuit can be formed externally instead of on the substrate.

[0399] Furthermore, although the pixel section 602 is formed by a plurality of pixels including a switching FET 611 and a current control FET 612 and a first electrode 613 electrically connected to its drain, it is not limited to this, and the pixel section may be a combination of three or more FETs and a capacitive element.

[0400] Furthermore, an insulator 614 is formed to cover the end of the first electrode 613. This can be formed by using a positive-type photosensitive acrylic resin film.

[0401] Furthermore, in order to ensure good coverage of the EL layer and the like that will be formed later, a curved surface with curvature is formed at the upper or lower end of the insulator 614. For example, when a positive-type photosensitive acrylic resin is used as the material for the insulator 614, it is preferable to have a curved surface with a radius of curvature (0.2 μm or more and 3 μm or less) only at the upper end of the insulator 614. In addition, either a negative-type photosensitive resin or a positive-type photosensitive resin can be used as the insulator 614.

[0402] An EL layer 616 and a second electrode 617 are formed on the first electrode 613, respectively. Here, it is desirable to use a material with a large work function for the first electrode 613 which functions as an anode. For example, in addition to single-layer films such as ITO film, silicon-containing indium tin oxide film, indium oxide film containing 2 wt% to 20 wt% zinc oxide, titanium nitride film, chromium film, tungsten film, Zn film, and Pt film, a laminate of titanium nitride film and a film mainly composed of aluminum, or a three-layer structure of titanium nitride film, a film mainly composed of aluminum, and titanium nitride film can be used. Furthermore, a laminated structure has low resistance as wiring, good ohmic contact can be obtained, and it can function as an anode.

[0403] Furthermore, the EL layer 616 is formed by various methods such as vapor deposition using a vapor deposition mask, inkjet printing, and spin coating. The EL layer 616 includes the configuration described in any one of Embodiments 2 to 6. In addition, other materials constituting the EL layer 616 may be low molecular weight compounds or high molecular weight compounds (including oligomers and dendrimers).

[0404] Furthermore, it is preferable to use a material with a small work function (such as Al, Mg, Li, Ca, or alloys or compounds thereof (MgAg, MgIn, AlLi, etc.)) for the second electrode 617, which is formed on the EL layer 616 and functions as a cathode. When light generated in the EL layer 616 is transmitted through the second electrode 617, it is preferable to use a laminate of a thin metal film and a transparent conductive film (such as ITO, indium oxide containing 2 wt% to 20 wt% zinc oxide, indium tin oxide containing silicon, zinc oxide (ZnO), etc.) as the second electrode 617.

[0405] The first electrode 613, the EL layer 616, and the second electrode 617 form a light-emitting device. This light-emitting device is the light-emitting device described in any one of Embodiments 2 to 6. The pixel portion has multiple light-emitting devices formed on it, and in the light-emitting device of this embodiment, both the light-emitting device described in any one of Embodiments 2 to 6 and light-emitting devices having other configurations may be mixed together.

[0406] Furthermore, by bonding the sealing substrate 604 to the element substrate 610 with the sealing material 605, the light-emitting device 618 is provided in the space 607 surrounded by the element substrate 610, the sealing substrate 604, and the sealing material 605. The space 607 may be filled with an inert gas (such as nitrogen or argon) or with the sealing material. A recess is formed in the sealing substrate, and a desiccant is placed therein to suppress deterioration due to the effects of moisture, which is a preferred configuration.

[0407] Furthermore, it is preferable to use epoxy resin or glass frit for the sealing material 605. It is also desirable that these materials are as impermeable to moisture and oxygen as possible. In addition to glass substrates or quartz substrates, plastic substrates made of FRP, PVF, polyester, or acrylic resin can be used as the material for the sealing substrate 604.

[0408] Although not shown in Figures 5(A) and 5(B), a protective film may be provided on the second electrode 617. The protective film may be formed of an organic resin film or an inorganic insulating film. Alternatively, the protective film may be formed to cover the exposed portion of the sealing material 605. Furthermore, the protective film can be provided to cover the surface and sides of the pair of substrates, the sealing layer, the insulating layer, and other exposed sides.

[0409] The protective film can be made of a material that is impermeable to impurities such as water. Therefore, it is possible to effectively suppress the diffusion of impurities such as water from the outside to the inside.

[0410] Materials that constitute the protective film can include oxides, nitrides, fluorides, sulfides, ternary compounds, metals, or polymers. For example, materials containing aluminum oxide, hafnium oxide, hafnium silicate, lanthanum oxide, silicon oxide, strontium titanate, tantalum oxide, titanium oxide, zinc oxide, niobium oxide, zirconium oxide, tin oxide, yttrium oxide, cerium oxide, scandium oxide, erbium oxide, vanadium oxide, or indium oxide can be used. Other materials containing aluminum nitride, hafnium nitride, silicon nitride, tantalum nitride, titanium nitride, niobium nitride, molybdenum nitride, zirconium nitride, or gallium nitride can be used. Nitrides containing titanium and aluminum, oxides containing titanium and aluminum, oxides containing aluminum and zinc, sulfides containing manganese and zinc, sulfides containing cerium and strontium, oxides containing erbium and aluminum, oxides containing yttrium and zirconium can be used.

[0411] It is preferable to form the protective film using a film deposition method that provides good step coverage. One such method is atomic layer deposition (ALD). It is preferable to use a material that can be formed using the ALD method for the protective film. By using the ALD method, it is possible to form a dense protective film with reduced defects such as cracks or pinholes, or a protective film with a uniform thickness. Furthermore, it is possible to reduce the damage inflicted on the processed member when forming the protective film.

[0412] For example, by forming a protective film using the ALD method, a uniform and defect-free protective film can be formed on surfaces with complex uneven shapes, or on the top, sides, and back surfaces of a touch panel.

[0413] As described above, a light-emitting device can be obtained using the light-emitting device described in any one of Embodiments 2 to 6.

[0414] Since the light-emitting device in this embodiment uses the light-emitting device described in any one of Embodiments 2 to 6, a light-emitting device with good characteristics can be obtained. Specifically, since the light-emitting device described in any one of Embodiments 2 to 6 has good luminous efficiency, it is possible to make a light-emitting device with low power consumption.

[0415] Figures 6(A) and 6(B) show examples of light-emitting devices that are made full-color by forming a light-emitting device that emits white light and providing a colored layer (color filter), etc. Figure 6(A) shows a substrate 1001, a base insulating film 1002, a gate insulating film 1003, a gate electrode 1006, a gate electrode 1007, a gate electrode 1008, a first interlayer insulating film 1020, a second interlayer insulating film 1021, a peripheral portion 1042, a pixel portion 1040, a drive circuit portion 1041, electrodes 1024W, 1024R, 1024G, and 1024B of the light-emitting device, a partition wall 1025, an EL layer 1028, an electrode 1029 of the light-emitting device, a sealing substrate 1031, a sealing material 1032, etc.

[0416] Furthermore, in Figure 6(A), the colored layers (red colored layer 1034R, green colored layer 1034G, and blue colored layer 1034B) are provided on a transparent substrate 1033. A black matrix 1035 may also be provided. The transparent substrate 1033 on which the colored layers and black matrix are provided is aligned and fixed to the substrate 1001. The colored layers and black matrix 1035 are covered with an overcoat layer 1036. In Figure 6(A), there is an emissive layer that emits light to the outside without transmitting through the colored layers, and an emissive layer that emits light to the outside by transmitting through each colored layer. Light that does not transmit through the colored layers is white, and light that transmits through the colored layers is red, green, and blue, so an image can be represented with four colored pixels.

[0417] Figure 6(B) shows an example in which colored layers (red colored layer 1034R, green colored layer 1034G, and blue colored layer 1034B) are formed between the gate insulating film 1003 and the first interlayer insulating film 1020. Thus, the colored layers may also be provided between the substrate 1001 and the encapsulating substrate 1031.

[0418] Furthermore, although the light-emitting device described above is a bottom-emission type device that extracts light from the substrate 1001 on which the FET is formed, it may also be a top-emission type device that extracts light from the sealing substrate 1031. A cross-sectional view of the top-emission type light-emitting device is shown in Figure 7. In this case, the substrate 1001 can be a substrate that does not transmit light. The process is the same as for the bottom-emission type light-emitting device until the connecting electrode that connects the FET and the anode of the light-emitting device is fabricated. After that, a third interlayer insulating film 1037 is formed covering the electrode 1022. This insulating film may also play a planarization role. The third interlayer insulating film 1037 can be formed using the same material as the second interlayer insulating film, as well as other known materials.

[0419] Electrodes 1024W, 1024R, 1024G, and 1024B of the light-emitting device are designated as anodes here, but they may also be cathodes. Furthermore, in the case of a top-emission type light-emitting device as shown in Figure 7, it is preferable that electrodes 1024W, 1024R, 1024G, and 1024B be reflective electrodes. The configuration of the EL layer 1028 is as described as unit 103 in any one of Embodiments 2 to 6, and the element structure is such that white light emission can be obtained.

[0420] In the top emission structure shown in Figure 7, sealing can be performed with a sealing substrate 1031 having colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B). A black matrix 1035 may be provided on the sealing substrate 1031 so as to be located between pixels. The colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B) or the black matrix may be covered with an overcoat layer 1036. The sealing substrate 1031 should be a translucent substrate. In addition, although an example of full-color display using four colors, red, green, blue, and white, is shown here, it is not particularly limited, and full-color display may be performed using four colors, red, yellow, green, and blue, or three colors, red, green, and blue.

[0421] In top-emission type light-emitting devices, a microcavity structure can be suitably applied. A light-emitting device having a microcavity structure is obtained by using a reflective electrode as the first electrode and a semi-transparent / semi-reflective electrode as the second electrode. There is at least an EL layer between the reflective electrode and the semi-transparent / semi-reflective electrode, and there is at least a light-emitting layer that forms a light-emitting region.

[0422] The reflective electrode has a visible light reflectance of 40% to 100%, preferably 70% to 100%, and its resistivity is 1 × 10⁻⁶. -2 The film thickness is assumed to be Ωcm or less. Furthermore, the semi-transparent / semi-reflective electrode has a visible light reflectance of 20% to 80%, preferably 40% to 70%, and its resistivity is 1 × 10⁻⁶. -2 Assume the membrane is less than Ωcm in diameter.

[0423] The light emitted from the light-emitting layer contained in the EL layer is reflected by the reflective electrode and the semi-transparent / semi-reflective electrode, causing resonance.

[0424] This light-emitting device allows you to change the optical distance between the reflective electrode and the semi-transparent / semi-reflective electrode by changing the thickness of the transparent conductive film or the aforementioned composite material, carrier transport material, etc. This makes it possible to strengthen light of resonant wavelengths and attenuate light of non-resonant wavelengths between the reflective electrode and the semi-transparent / semi-reflective electrode.

[0425] Furthermore, since the light reflected back by the reflective electrode (first reflected light) interferes significantly with the light that directly enters the semi-transparent / semi-reflective electrode from the light-emitting layer (first incident light), it is preferable to adjust the optical distance between the reflective electrode and the light-emitting layer to (2n-1)λ / 4 (where n is a natural number greater than or equal to 1, and λ is the wavelength of the light emission to be amplified). By adjusting this optical distance, the phases of the first reflected light and the first incident light can be aligned, and the light emission from the light-emitting layer can be further amplified.

[0426] In the above configuration, the EL layer may have a structure with multiple light-emitting layers or a structure with a single light-emitting layer. For example, it may be applied to a configuration in which multiple EL layers are provided in a single light-emitting device with a charge generation layer in between, and one or more light-emitting layers are formed in each EL layer, in combination with the tandem light-emitting device configuration described above.

[0427] By incorporating a microcavity structure, it becomes possible to enhance the emission intensity of specific wavelengths, thereby reducing power consumption. Furthermore, in the case of a light-emitting device that displays images using four sub-pixels of red, yellow, green, and blue, the brightness is enhanced by the yellow emission, and since a microcavity structure tailored to the wavelength of each color can be applied to all sub-pixels, a light-emitting device with excellent characteristics can be achieved.

[0428] Since the light-emitting device in this embodiment uses the light-emitting device described in any one of Embodiments 2 to 6, a light-emitting device with good characteristics can be obtained. Specifically, since the light-emitting device described in any one of Embodiments 2 to 6 has good luminous efficiency, it is possible to make a light-emitting device with low power consumption.

[0429] Up to this point, we have described an active matrix type light-emitting device, but from here on we will describe a passive matrix type light-emitting device. Figures 8(A) and 8(B) show a passive matrix type light-emitting device manufactured by applying the present invention. Figure 8(A) is a perspective view of the light-emitting device, and Figure 8(B) is a cross-sectional view of Figure 8(A) cut along the X and Y lines. In Figures 8(A) and 8(B), an EL layer 955 is provided on the substrate 951 between electrodes 952 and 956. The ends of electrodes 952 are covered with an insulating layer 953. A partition layer 954 is provided on the insulating layer 953. The side walls of the partition layer 954 have a slope such that the distance between one side wall and the other side wall narrows as it approaches the substrate surface. In other words, the cross-section of the partition layer 954 in the short-side direction is trapezoidal, with the bottom side (facing the same direction as the surface direction of the insulating layer 953 and in contact with the insulating layer 953) being shorter than the top side (facing the same direction as the surface direction of the insulating layer 953 and not in contact with the insulating layer 953). By providing the partition layer 954 in this way, it is possible to prevent malfunctions of the light-emitting device caused by static electricity, etc. Furthermore, even in a passive matrix type light-emitting device, the light-emitting device described in any one of Embodiments 2 to 6 can be used, resulting in a light-emitting device with good reliability or low power consumption.

[0430] As described above, the light-emitting device is suitable for use as a display device for representing images because it is possible to control each of the numerous minute light-emitting devices arranged in a matrix.

[0431] Furthermore, this embodiment can be freely combined with other embodiments.

[0432] (Embodiment 10) In this embodiment, an example of using the light-emitting device described in any one of Embodiments 2 to 6 as an illumination device will be described with reference to Figure 9. Figure 9(B) is a top view of the illumination device, and Figure 9(A) is a cross-sectional view taken at ef in Figure 9(B).

[0433] In this embodiment, the lighting device has a first electrode 401 formed on a translucent substrate 400 which serves as a support. The first electrode 401 corresponds to the electrode 551X in any one of Embodiments 2 to 6. When light is extracted from the first electrode 401 side, the first electrode 401 is formed from a translucent material.

[0434] A pad 412 for supplying voltage to the second electrode 404 is formed on the substrate 400.

[0435] An EL layer 403 is formed on the first electrode 401. The EL layer 403 corresponds to a configuration combining layer 104, unit 103, and layer 105 in any one of Embodiments 2 to 6, or a configuration combining layer 104, unit 103X, layer 106, unit 103X2, and layer 105. Please refer to the respective descriptions for details on these configurations.

[0436] A second electrode 404 is formed by covering the EL layer 403. The second electrode 404 corresponds to electrode 552X in any one of Embodiments 2 to 6. When light emission is extracted from the first electrode 401 side, the second electrode 404 is formed of a material with high reflectivity. Voltage is supplied to the second electrode 404 by connecting it to the pad 412.

[0437] As described above, the lighting device shown in this embodiment has a light-emitting device having a first electrode 401, an EL layer 403, and a second electrode 404. Since this light-emitting device is a light-emitting device with high luminous efficiency, the lighting device in this embodiment can be a lighting device with low power consumption.

[0438] The lighting device is completed by fixing and sealing the substrate 400, on which the light-emitting device having the above configuration is formed, and the sealing substrate 407 using sealing materials 405 and 406. Either sealing material 405 or 406 may be used. In addition, a desiccant can be mixed into the inner sealing material 406 (not shown in Figure 9(B)), which allows for the adsorption of moisture and leads to improved reliability.

[0439] Furthermore, by extending the pad 412 and a portion of the first electrode 401 outside the sealing material 405 and sealing material 406, it can be used as an external input terminal. Alternatively, an IC chip 420 with a converter or the like may be provided on top of it.

[0440] As described above, the lighting device described in this embodiment is equipped with the light-emitting device described in any one of Embodiments 2 to 6, and can be a lighting device with low power consumption.

[0441] (Embodiment 11) This embodiment describes an example of an electronic device that includes a light-emitting device as described in any one of Embodiments 2 to 6. The light-emitting device described in any one of Embodiments 2 to 6 has good luminous efficiency and low power consumption. As a result, the electronic device described in this embodiment can be an electronic device having a light-emitting section with low power consumption.

[0442] Examples of electronic devices to which the above-mentioned light-emitting devices are applied include television equipment (also called televisions or television receivers), monitors for computers, digital cameras, digital video cameras, digital photo frames, mobile phones (also called mobile phones or mobile phone devices), portable game consoles, personal digital assistants, sound playback devices, and large game machines such as pachinko machines. Specific examples of these electronic devices are shown below.

[0443] Figure 10(A) shows an example of a television system. The television system has a display unit 7103 incorporated into a housing 7101. This figure also shows a configuration in which the housing 7101 is supported by a stand 7105. The display unit 7103 is capable of displaying images, and the display unit 7103 is configured by arranging the light-emitting devices described in any one of Embodiments 2 to 6 in a matrix.

[0444] The television system can be operated using the operation switches on the housing 7101 or a separate remote control unit 7110. The remote control unit 7110 has operation keys 7109 that allow for channel or volume control, and the image displayed on the display unit 7103 can be controlled. Alternatively, a display unit 7107 may be provided on the remote control unit 7110 to display output information.

[0445] The television system shall consist of a receiver or modem. The receiver will be able to receive general television broadcasts, and by connecting to a wired or wireless communication network via the modem, it will also be possible to perform one-way (from sender to receiver) or two-way (between sender and receiver, or between receivers, etc.) information communication.

[0446] Figure 10(B) shows a computer, which includes a main unit 7201, a housing 7202, a display unit 7203, a keyboard 7204, an external connection port 7205, a pointing device 7206, etc. This computer is manufactured by arranging the light-emitting devices described in any one of Embodiments 2 to 6 in a matrix and using them for the display unit 7203. The computer in Figure 10(B) may also take the form shown in Figure 10(C). The computer in Figure 10(C) is provided with a second display unit 7210 instead of the keyboard 7204 and pointing device 7206. The second display unit 7210 is a touch panel, and input can be performed by operating the input display shown on the second display unit 7210 with a finger or a dedicated pen. In addition to the input display, the second display unit 7210 can also display other images. The display unit 7203 may also be a touch panel. The two screens are connected by a hinge, which prevents problems such as scratching or damaging the screens when storing or transporting the device.

[0447] Figure 10(D) shows an example of a mobile terminal. The mobile terminal includes a display unit 7402 incorporated into a housing 7401, as well as operation buttons 7403, an external connection port 7404, a speaker 7405, a microphone 7406, and the like. The mobile terminal has a display unit 7402 made by arranging the light-emitting devices described in any one of Embodiments 2 to 6 in a matrix.

[0448] The mobile terminal shown in Figure 10(D) can also be configured to allow information input by touching the display unit 7402 with a finger or other object. In this case, operations such as making a phone call or composing an email can be performed by touching the display unit 7402 with a finger or other object.

[0449] The display unit 7402 has three main modes. The first is a display mode that primarily displays images, the second is an input mode that primarily inputs information such as text, and the third is a display + input mode that combines the display mode and the input mode.

[0450] For example, when making a phone call or composing an email, the display unit 7402 should be set to a text input mode, which primarily focuses on text input, and the user should input the characters displayed on the screen. In this case, it is preferable to display a keyboard or number buttons on most of the screen of the display unit 7402.

[0451] Furthermore, by providing a detection device with tilt-detecting sensors such as a gyroscope and an accelerometer inside the mobile terminal, the orientation of the mobile terminal (portrait or landscape) can be determined, and the screen display of the display unit 7402 can be automatically switched accordingly.

[0452] Furthermore, the screen mode can be switched by touching the display unit 7402 or by operating the operation button 7403 on the housing 7401. It is also possible to switch modes depending on the type of image displayed on the display unit 7402. For example, if the image signal displayed on the display unit is video data, it can be switched to display mode; if it is text data, it can be switched to input mode.

[0453] Furthermore, in input mode, the system may detect a signal detected by the optical sensor of the display unit 7402 and, if there is no input via touch operation on the display unit 7402 for a certain period of time, control may be made to switch the screen mode from input mode to display mode.

[0454] The display unit 7402 can also function as an image sensor. For example, by touching the display unit 7402 with the palm or finger, palm prints, fingerprints, etc., can be captured to perform user authentication. Furthermore, by using a backlight that emits near-infrared light or a sensing light source that emits near-infrared light in the display unit, finger veins, palm veins, etc., can also be captured.

[0455] Figure 11(A) is a schematic diagram showing an example of a cleaning robot.

[0456] The cleaning robot 5100 has a display 5101 on its top surface, multiple cameras 5102 on its sides, a brush 5103, and control buttons 5104. Although not shown in the illustration, the cleaning robot 5100 also has wheels, a suction port, etc. on its underside. The cleaning robot 5100 is also equipped with various sensors, including an infrared sensor, an ultrasonic sensor, an accelerometer, a piezoelectric sensor, a light sensor, and a gyroscope. Furthermore, the cleaning robot 5100 is equipped with a means of wireless communication.

[0457] The cleaning robot 5100 is self-propelled, can detect dirt 5120, and can suck up the dirt through a suction port located on its underside.

[0458] Furthermore, the cleaning robot 5100 can analyze images captured by the camera 5102 to determine the presence or absence of obstacles such as walls, furniture, or steps. If the image analysis detects objects that could become entangled in the brush 5103, such as wiring, it can stop the brush 5103 from rotating.

[0459] The display 5101 can display information such as the remaining battery level or the amount of dirt collected. The path taken by the cleaning robot 5100 may also be displayed on the display 5101. Alternatively, the display 5101 may be a touch panel, and operation buttons 5104 may be provided on the display 5101.

[0460] The cleaning robot 5100 can communicate with a portable electronic device 5140, such as a smartphone. Images captured by the camera 5102 can be displayed on the portable electronic device 5140. Therefore, the owner of the cleaning robot 5100 can check the status of the room even when they are away from home. In addition, the display on the display 5101 can be viewed on the portable electronic device 5140, such as a smartphone.

[0461] A light-emitting device according to one aspect of the present invention can be used in a display 5101.

[0462] The robot 2100 shown in Figure 11(B) includes a computing unit 2110, a microphone 2102, an upper camera 2103, a speaker 2104, a display 2105, a lower camera 2106, an obstacle sensor 2107, and a movement mechanism 2108.

[0463] The microphone 2102 has the function of detecting the user's voice and ambient sounds. The speaker 2104 has the function of emitting sound. The robot 2100 can communicate with the user using the microphone 2102 and speaker 2104.

[0464] The display 2105 has the function of displaying various types of information. The robot 2100 can display the information desired by the user on the display 2105. The display 2105 may be equipped with a touch panel. The display 2105 may also be a detachable information terminal, and by installing it in a fixed position on the robot 2100, charging and data transfer can be made possible.

[0465] The upper camera 2103 and the lower camera 2106 have the function of imaging the area around the robot 2100. In addition, the obstacle sensor 2107 can detect the presence or absence of obstacles in the direction of travel when the robot 2100 moves forward using the movement mechanism 2108. The robot 2100 can recognize its surrounding environment and move safely using the upper camera 2103, the lower camera 2106 and the obstacle sensor 2107. The light-emitting device according to one aspect of the present invention can be used in the display 2105.

[0466] Figure 11(C) shows an example of a goggle-type display. The goggle-type display includes, for example, a housing 5000, a display unit 5001, a speaker 5003, an LED lamp 5004, operation keys (including a power switch or operation switch), connection terminals 5006, a sensor 5007 (including functions for measuring force, displacement, position, velocity, acceleration, angular velocity, rotational speed, distance, light, liquid, magnetism, temperature, chemical substances, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared radiation), a microphone 5008, a display unit 5002, a support unit 5012, an earphone 5013, etc.

[0467] A light-emitting device according to one aspect of the present invention can be used in the display unit 5001 and the display unit 5002.

[0468] Figure 12 shows an example in which the light-emitting device described in any one of Embodiments 2 to 6 is used in a desk lamp, which is a lighting device. The desk lamp shown in Figure 12 has a housing 2001 and a light source 2002, and the lighting device described in Embodiment 10 may be used as the light source 2002.

[0469] Figure 13 shows an example of using the light-emitting device described in any one of Embodiments 2 to 6 as an indoor lighting device 3001. Since the light-emitting device described in any one of Embodiments 2 to 6 is a light-emitting device with high luminous efficiency, it can be used as a lighting device with low power consumption. Furthermore, since the light-emitting device described in any one of Embodiments 2 to 6 can be made to cover a large area, it can be used as a large-area lighting device. In addition, since the light-emitting device described in any one of Embodiments 2 to 6 is thin, it can be used as a thin lighting device.

[0470] The light-emitting device described in any one of Embodiments 2 to 6 can also be mounted on the windshield or dashboard of an automobile. Figure 14 shows one embodiment in which the light-emitting device described in any one of Embodiments 2 to 6 is used on the windshield or dashboard of an automobile. Display areas 5200 to 5203 are display areas provided using the light-emitting device described in any one of Embodiments 2 to 6.

[0471] Display area 5200 and display area 5201 are display devices equipped with a light-emitting device according to any one of Embodiments 2 to 6, which is installed on the windshield of an automobile. The light-emitting device according to any one of Embodiments 2 to 6 can be made into a so-called see-through display device, where the opposite side is visible, by making the first electrode and the second electrode from translucent electrodes. If the display is in a see-through state, it can be installed on the windshield of an automobile without obstructing the view. When providing transistors for driving, it is preferable to use translucent transistors such as organic transistors made of organic semiconductor materials or transistors using oxide semiconductors.

[0472] The display area 5202 is a display device equipped with a light-emitting device described in any one of Embodiments 2 to 6, which is provided on the pillar. By displaying images from an imaging means provided on the vehicle body on the display area 5202, the field of view obstructed by the pillar can be supplemented. Similarly, the display area 5203 provided on the dashboard can compensate for blind spots and enhance safety by displaying images from an imaging means provided on the outside of the vehicle, which is obstructed by the vehicle body. By displaying images in a way that supplements the parts that are not visible, safety checks can be performed more naturally and without discomfort.

[0473] Display area 5203 can provide various information by displaying navigation information, speed or RPM, mileage, fuel level, gear status, air conditioning settings, etc. The display items and layout can be changed as needed to suit the user's preferences. This information can also be provided in display areas 5200 to 5202. Furthermore, display areas 5200 to 5203 can also be used as lighting devices.

[0474] Figures 15(A) to 15(C) also show the foldable portable information terminal 9310. Figure 15(A) shows the portable information terminal 9310 in its unfolded state. Figure 15(B) shows the portable information terminal 9310 in an intermediate state, transitioning from either the unfolded or folded state to the other. Figure 15(C) shows the portable information terminal 9310 in its folded state. The portable information terminal 9310 offers excellent portability in its folded state and excellent readability of the display due to its seamless, wide display area in its unfolded state.

[0475] The display panel 9311 is supported by three housings 9315 connected by a hinge 9313. The display panel 9311 may also be a touch panel (input / output device) equipped with a touch sensor (input device). Furthermore, the display panel 9311 can be reversibly transformed from an unfolded state to a folded state by bending the two housings 9315 via the hinge 9313. A light-emitting device according to one aspect of the present invention can be used in the display panel 9311.

[0476] Furthermore, the configuration shown in this embodiment can be used by appropriately combining the configurations shown in Embodiments 2 to 6.

[0477] As described above, the application range of the light-emitting device equipped with the light-emitting device described in any one of Embodiments 2 to 6 is extremely broad, and this light-emitting device can be applied to electronic devices in all fields. By using the light-emitting device described in any one of Embodiments 2 to 6, it is possible to obtain electronic devices with low power consumption.

[0478] This embodiment can be appropriately combined with other embodiments shown in this specification. [Examples]

[0479] (Synthesis Example 1) This example describes the physical properties and synthesis method of an organic compound according to one embodiment of the present invention. Specifically, the synthesis method of 2,9-di(1-naphthyl)-10-phenylanthracene-1,3,4,5,6,7,8-d7 (abbreviated as 2αN-αNPhA-d7), shown by structural formula (029) in Embodiment 1, will be described. The structure of 2αN-αNPhA-d7 is shown below.

[0480] [ka]

[0481] <Step 1: Synthesis of 2-bromoanthracene-1,3,4,5,6,7,8,9,10-d9> 2.6 g (10 mmol) of 2-bromoanthracene was added to a 50 mL three-necked flask, and the flask was purged with nitrogen. 20 mL of toluene-d8 and 0.90 g (3.3 mmol) of molybdenum(V) pentachloride (MoCl5) were added, and the mixture was stirred under a nitrogen stream at 80°C for 11 hours.

[0482] After stirring, toluene and 2N hydrochloric acid were added to the mixture, separating it into an aqueous layer and an organic layer. The target substance in the aqueous layer was extracted using toluene. The obtained extract and the organic layer were combined, washed with saturated sodium bicarbonate aqueous solution and saturated brine, and then dried over magnesium sulfate. This mixture was filtered by natural filtration, and the filtrate was concentrated to obtain a brown solid.

[0483] Toluene was added to the obtained solid and heated. The mixture was then filtered by suction through Florizil (Wako Pure Chemical Industries, Ltd., catalog number: 066-05265), Celite (Wako Pure Chemical Industries, Ltd., catalog number: 537-02305), and alumina to obtain the filtrate. The obtained filtrate was concentrated to obtain a brown solid.

[0484] The obtained solid was recrystallized with toluene and hexane to remove impurities through recrystallization. The filtrate obtained by suction filtration was concentrated to yield 1.1 g of the target white solid in a yield of 41%. The synthesis scheme for Step 1 is shown below (a-1).

[0485] [ka]

[0486] Furthermore, when the molecular weight of the solid obtained in step 1 was measured by LC / MS (Liquid chromatography / mass spectrometry), it was found that the m / e ratio was 265, relative to the molecular weight of the target substance (265), thus indicating that 2-bromoanthracene-1,3,4,5,6,7,8,9,10-d9 was obtained.

[0487] <Step 2: Synthesis of 2-(1-naphthyl)anthracene-1,3,4,5,6,7,8,9,10-d9> 1.1 g (4.1 mmol) of 2-bromoanthracene-1,3,4,5,6,7,8,9,10-d9, 0.90 g (5.2 mmol) of 1-naphthaleneboronic acid, and 60 mg (0.20 mmol) of tri(o-tolyl)phosphine (abbreviated as P(o-tol)3) were added to a 100 mL three-necked flask, and the flask was purged with nitrogen. 35 mL of toluene (abbreviated as Toluene), 10 mL of ethanol (abbreviated as EtOH), and 5 mL of 2 M potassium carbonate (abbreviated as K2CO3) aqueous solution were added, and the flask was degassed under reduced pressure. Then, 20 mg (89 μmol) of palladium(II) acetate (abbreviated as Pd(OAc)2) was added to the mixture, and the mixture was stirred at 90°C for 6 hours under a nitrogen stream.

[0488] After stirring, water was added to the mixture to separate it into an aqueous layer and an organic layer. The target substance in the aqueous layer was extracted using toluene. The obtained extract and the organic layer were combined, washed with water and saturated brine, and then dried over magnesium sulfate. This mixture was filtered by natural filtration, and the filtrate was concentrated to obtain a brown oily substance.

[0489] The resulting oily substance was purified by silica gel column chromatography, yielding 1.2 g of the target product as a white solid in 93% yield. The synthesis scheme is shown below (a-2).

[0490] [ka]

[0491] Furthermore, the white solid obtained in step 2 above 1 The results of the 1H NMR measurement are shown below. From these results, it was found that 2-(1-naphthyl)anthracene-1,3,4,5,6,7,8,9,10-d9 was obtained.

[0492] 1 H NMR (CDCl3,300MHz): σ=8.14-7.90 (m, 3H), 7.66-7.42 (m, 4H).

[0493] <Step 3: Synthesis of 2-(1-naphthyl)-9-bromoanthracene-1,3,4,5,6,7,8,10-d8> 1.2 g (3.8 mmol) of 2-(1-naphthyl)anthracene-1,3,4,5,6,7,8,9,10-d9 was added to a 1 L round-bottom flask, and the flask was purged with nitrogen. 30 mL of toluene and 30 mL of N,N-dimethylformamide (DMF) were added, and the mixture was stirred at room temperature. 0.75 g (4.2 mmol) of N-bromosuccinimide (NBS) was added to this solution, and the mixture was stirred at room temperature for 21 hours.

[0494] After stirring, water was added to the mixture, and the aqueous layer was extracted with toluene. The obtained extract and the organic layer were combined, washed with water and saturated brine, and then dried over magnesium sulfate. This mixture was filtered by natural filtration, and the filtrate was concentrated to obtain a brown solid.

[0495] The obtained solid was purified by adding toluene and methanol and irradiating it with ultrasound, yielding 0.60 g of the target white solid in a yield of 40%. The synthesis scheme for Step 3 is shown below (a-3).

[0496] [ka]

[0497] Furthermore, the white solid obtained in step 3 above 1 The results of the 1H NMR measurement are shown below. From these results, it was found that 2-(1-naphthyl)-9-bromoanthracene-1,3,4,5,6,7,8,10-d8 was obtained.

[0498] 1 H NMR (CDCl3,300MHz):σ=7.99-7.92(m, 3H), 7.63-7.44(m, 4H).

[0499] <Step 4: Synthesis of 2,9-di(1-naphthyl)anthracene-1,3,4,5,6,7,8,10-d8> 0.60 g (1.5 mmol) of 2-(1-naphthyl)-9-bromoanthracene-1,3,4,5,6,7,8,10-d8, 0.30 g (1.7 mmol) of 1-naphthaleneboronic acid, and 30 mg (99 μmol) of tri(o-tolyl)phosphine were added to a 50 mL three-necked flask, and the flask was purged with nitrogen. 15 mL of toluene, 4 mL of ethanol, and 2 mL of 2 M potassium carbonate aqueous solution were added, and the flask was degassed under reduced pressure. Then, 10 mg (45 μmol) of palladium(II) acetate was added to the mixture, and the mixture was stirred at 90°C for 2 hours under a nitrogen stream.

[0500] After stirring, water was added to the mixture, and the aqueous layer was extracted with toluene. The resulting extract and the organic layer were combined, washed with water and saturated brine, and then dried over magnesium sulfate. This mixture was filtered by natural filtration, and the filtrate was concentrated to obtain a brown oily substance.

[0501] The resulting oily substance was purified by silica gel column chromatography, yielding 0.60 g of the target product as a white solid in 89% yield. The synthesis scheme is shown below (a-4).

[0502] [ka]

[0503] Furthermore, the white solid obtained in step 4 above 1 The results of the 1H NMR measurement are shown below. From these results, it was found that 2,9-di(1-naphthyl)anthracene-1,3,4,5,6,7,8,10-d8 was obtained.

[0504] 1 H NMR (CDCl3,300MHz):σ=7.97-7.92(m, 2H), 7.83-7.75(m, 3H), 7.65-7.38(m, 5H), 7.33-7.16(m, 4H).

[0505] <Step 5: Synthesis of 2,9-di(1-naphthyl)-10-bromoanthracene-1,3,4,5,6,7,8-d7> 0.99 g (2.3 mmol) of 2,9-di(1-naphthyl)anthracene-1,3,4,5,6,7,8,10-d8 was added to a 500 mL round-bottom flask, and the flask was purged with nitrogen. 20 mL of toluene and 30 mL of DMF were added, and the mixture was heated to 50°C to dissolve. After returning to room temperature, the mixture was stirred. 0.50 g (2.8 mmol) of N-bromosuccinimide was added to this solution, and the mixture was stirred at room temperature for 21 hours.

[0506] After stirring, water was added to the mixture, and the aqueous layer was extracted with toluene. The obtained extract and the organic layer were combined, washed with water and saturated brine, and then dried over magnesium sulfate. This mixture was filtered by natural filtration, and the filtrate was concentrated to obtain a brown solid.

[0507] The obtained solid was recrystallized with toluene, yielding 1.0 g of the target white solid in 87% yield. The synthesis scheme for Step 5 is shown below (a-5).

[0508] [ka]

[0509] Furthermore, the white solid obtained in step 5 above 1 The results of the 1H NMR measurement are shown below. From these results, it was found that 2,9-di(1-naphthyl)-10-bromoanthracene-1,3,4,5,6,7,8-d7 was obtained.

[0510] 1 H NMR (CDCl3,300MHz):σ=7.98-7.93(m, 2H), 7.84-7.73(m, 3H), 7.64-7.38(m, 5H), 7.32-7.13(m, 4H).

[0511] <Step 6: Synthesis of 2αN-αNPhA-d7> 0.7 g (1.4 mmol) of 2,9-di(1-naphthyl)-10-bromoanthracene-1,3,4,5,6,7,8-d7, 0.20 g (1.6 mmol) of phenylboronic acid, and 60 mg (0.20 mmol) of tri(o-tolyl)phosphine were added to a 200 mL three-necked flask, and the flask was purged with nitrogen. 15 mL of toluene, 4 mL of ethanol, and 2 mL of 2 M potassium carbonate aqueous solution were added, and the flask was degassed under reduced pressure. Then, 20 mg (89 μmol) of palladium(II) acetate was added to the mixture, and the mixture was stirred at 90°C for 2 hours under a nitrogen stream.

[0512] After stirring, water was added to the mixture, and the aqueous layer was extracted with toluene. The obtained extract and the organic layer were combined, washed with water and saturated brine, and then dried over magnesium sulfate. This mixture was filtered by natural filtration, and the filtrate was concentrated to obtain a brown solid.

[0513] The obtained solid was recrystallized with toluene, yielding 0.61 g of the target yellowish-white solid in 88% yield. The synthesis scheme for Step 6 is shown below (a-6).

[0514] [ka]

[0515] The deuterated chloroform (CDCl3) solution of the obtained compound 1 The 1H NMR spectra of the yellowish-white solid are shown in Figures 16(A) and 16(B). 1 The results of the 1H NMR measurement are shown below. From these results, it was found that 2αN-αNPhA-d7 (structural formula (029)) was obtained.

[0516] 1 H NMR (CDCl3,300MHz):σ=7.98-7.94(m, 2H), 7.81-7.74(m, 3H), 7.68-7.58(m, 7H), 7.53-7.35(m, 3H), 7.30-7.18(m, 4H).

[0517] The obtained yellowish-white solid (0.60 g) was purified by sublimation using the train sublimation method. Sublimation purification was performed by heating the yellowish-white solid at 225°C for 15 hours under a pressure of 3.0 Pa. After sublimation purification, the target yellow solid was obtained in a yield of 0.49 g with a recovery rate of 82%.

[0518] <Physical properties> The ultraviolet-visible absorption and emission spectra of a toluene solution of 2αN-αNPhA-d7 are explained using Figure 17.

[0519] Figure 17 illustrates the wavelength dependence of absorption intensity and emission intensity.

[0520] The ultraviolet-visible absorption spectrum of a toluene solution of 2αN-αNPhA-d7 showed a peak in absorption intensity around 403 nm (see Figure 17). The emission spectrum also showed a peak in emission intensity around 420 nm. Light with a wavelength of 380 nm was used as excitation light.

[0521] For measuring the ultraviolet-visible absorption spectrum, an ultraviolet-visible spectrophotometer (V-770DS, manufactured by JASCO Corporation) was used. For measuring the emission spectrum, a spectrofluorometer (FP-8600DS, manufactured by JASCO Corporation) was used. [Examples]

[0522] In this embodiment, a light-emitting device 1 according to one aspect of the present invention will be described with reference to Figures 18 to 25.

[0523] Figure 18 is a diagram illustrating the configuration of the light-emitting device 550X.

[0524] Figure 19 illustrates the current density-luminance characteristics of the light-emitting device 1 and the comparison device 1.

[0525] Figure 20 illustrates the luminance-current efficiency characteristics of light-emitting device 1 and comparator device 1.

[0526] Figure 21 illustrates the voltage-luminance characteristics of the light-emitting device 1 and the comparator device 1.

[0527] Figure 22 illustrates the voltage-current characteristics of the light-emitting device 1 and the comparator device 1.

[0528] Figure 23 illustrates the luminance-external quantum efficiency characteristics of light-emitting device 1 and comparison device 1. The external quantum efficiency was calculated from the luminance, assuming that the light distribution characteristics of the light-emitting device are Lambertsian.

[0529] Figure 24 shows the light-emitting device 1 and comparison device 1 at 1000 cd / m².2 This diagram illustrates the emission spectrum when the light source is emitted at a specific brightness level.

[0530] Figure 25 shows a constant current density (50 mA / cm²). 2 This figure illustrates the change over time in the normalized brightness of light-emitting device 1 and comparison device 1 when they are illuminated using ).

[0531] <Light-emitting device 1> The light-emitting device 1 described in this embodiment has the same configuration as the light-emitting device 550X (see Figure 18).

[0532] The light-emitting device 1 includes an electrode 551, an electrode 552, and a unit 103. Electrode 552 overlaps with electrode 551, and unit 103 is sandwiched between electrodes 551 and 552.

[0533] Unit 103 comprises layers 111, 112, and 113, with layer 111 sandwiched between layers 112 and 113.

[0534] Furthermore, layer 113 is sandwiched between electrode 552 and layer 111, layer 112 is sandwiched between layer 111 and electrode 551, and layer 112 contains a hole-transporting material.

[0535] Layer 111 contains the luminescent organic compound EM and an organic compound represented by the following general formula (G1).

[0536] [ka]

[0537] However, in the above general formula (G1), R 1 ~R 26 At least one of them is deuterium.

[0538] Also, R 1 ~R 7At least one of the following is a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted trialkylsilyl group, or a substituted or unsubstituted aryl group. Also, R 1 ~R 7 Other than these, each is independently one of the following: hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted trialkylsilyl group, or a substituted or unsubstituted aryl group.

[0539] R 8 ~R 26 Each of these is independently one of the following: hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted trialkylsilyl group, or a substituted or unsubstituted aryl group.

[0540] Note, R 1 ~R 26 The alkyl group to be substituted has 3 to 10 carbon atoms, R 1 ~R 26 The cycloalkyl group to be substituted has 3 to 10 carbon atoms, R 1 ~R 26 The trialkylsilyl group to be substituted has 3 to 12 carbon atoms, R 1 ~R 26 The aryl group to be substituted has between 6 and 25 carbon atoms.

[0541] Configuration of Light-Emitting Device 1 Table 1 shows the configuration of the light-emitting device 1. The structural formulas of the materials used in the light-emitting device described in this embodiment are shown below. In the table of this embodiment, subscripts and superscripts are written in standard size for convenience. For example, subscripts used in abbreviations and superscripts used in units are written in standard size in the table. These descriptions in the table can be interpreted with reference to the description in the specification.

[0542] [Table 1]

[0543] [ka]

[0544] 《Method for fabricating light-emitting device 1》 The light-emitting device 1 described in this embodiment was fabricated using a method comprising the following steps.

[0545] [Step 1] In the first step, electrode 551 was formed. Specifically, it was formed by sputtering using indium tin oxide (ITSO), which contains silicon or silicon oxide, as the target.

[0546] Electrode 551 contains ITSO and has a thickness of 70 nm and 4 mm 2 It has an area of ​​(2mm x 2mm).

[0547] Next, the substrate on which the electrode 551 was formed was washed with water, fired at 200°C for 1 hour, and then subjected to UV ozone treatment for 370 seconds. -4 The substrate was introduced into a vacuum deposition apparatus where the internal pressure was reduced to approximately Pa, and vacuum firing was performed at 170°C for 30 minutes in the heating chamber within the vacuum deposition apparatus. After that, the substrate was allowed to cool for about 30 minutes.

[0548] [Step 2] In the second step, layer 104 was formed on electrode 551. Specifically, the material was co-deposited using resistance heating.

[0549] Layer 104 contains N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviated as BBABnf) and an electron acceptor material (abbreviated as OCHD-003) in a ratio of BBABnf:OCHD-003 = 1:0.1 (by weight), and has a thickness of 10 nm. The electron acceptor material OCHD-003 contains fluorine and has a molecular weight of 672.

[0550] [Step 3] In the third step, layer 112(1) was formed on layer 104. Specifically, the material was deposited using a resistance heating method.

[0551] Layer 112(1) contains BBABnf and has a thickness of 20 nm.

[0552] [Step 4] In the fourth step, layer 112(2) was formed on layer 112(1). Specifically, the material was deposited using a resistance heating method.

[0553] Layer 112(2) contains 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl-9H-carbazole) (abbreviated as PCzN2) and has a thickness of 10 nm.

[0554] [Step 5] In the fifth step, layer 111 was formed on layer 112(2). Specifically, the material was co-deposited using the resistance heating method.

[0555] Layer 111 contains 2,9-di(1-naphthyl)-10-phenylanthracene-1,3,4,5,6,7,8-d7 (abbreviated as 2αN-αNPhA-d7) and 3,10-bis[N-(9-phenyl-9H-carbazole-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviated as 3,10PCA2Nbf(IV)-02) in a weight ratio of 2αN-αNPhA-d7:3,10PCA2Nbf(IV)-02 = 1:0.015 and has a thickness of 25 nm. 3,10PCA2Nbf(IV)-02 is an organic compound that emits blue fluorescence, and 3,10PCA2Nbf(IV)-02 was used as the luminescent organic compound EM.

[0556] [Step 6] In the sixth step, layer 113(1) was formed on layer 111. Specifically, the material was deposited using a resistance heating method.

[0557] Layer 113(1) contains 2-[3-(3'-dibenzothiophen-4-yl)biphenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II) and has a thickness of 10 nm.

[0558] [Step 7] In the seventh step, layer 113(2) was formed on layer 113(1). Specifically, the material was deposited using a resistance heating method.

[0559] Layer 113(2) contains 2,9-di(2-naphthyl)-4,7-diphenyl-1,10-phenanthroline (abbreviated as NBPhen) and has a thickness of 20 nm.

[0560] [Step 8] In the eighth step, layer 105 was formed on layer 113(2). Specifically, the material was deposited using a resistance heating method.

[0561] Layer 105 contains lithium fluoride (abbreviated as LiF) and has a thickness of 1 nm.

[0562] [Step 9] In the ninth step, an electrode 552 was formed on layer 105. Specifically, the material was deposited using a resistance heating method.

[0563] Electrode 552 contains aluminum (abbreviated as Al) and has a thickness of 150 nm.

[0564] Operating characteristics of the light-emitting device 1 When power was supplied, the light-emitting device 1 emitted ELX light (see Figure 18). The operating characteristics of the light-emitting device 1 were measured at room temperature (see Figures 19 to 24). A spectroradiometer (Topcon SR-UL1R) was used to measure luminance, CIE chromaticity, and emission spectrum.

[0565] The fabricated light-emitting device has a brightness of 1000 cd / m². 2Table 2 shows the main initial characteristics when the light-emitting device is activated at a certain current density (50 mA / cm²). 2 Table 2 shows the LT95, which is the time elapsed until the brightness decreases to 95% of the initial brightness after emitting light using the specified method. The characteristics of other light-emitting devices, whose configuration will be described later, are also listed in Table 2.

[0566] [Table 2]

[0567] Light-emitting device 1 was found to exhibit good characteristics. In particular, the time it took for the brightness to decrease to 95% of the initial brightness was longer than that of comparison device 1, demonstrating high reliability.

[0568] By utilizing carbon-deuterium bonds, which have a higher bond dissociation energy than carbon-hydrogen bonds, the bond dissociation energy of compounds can be increased. Furthermore, bond dissociation within the compound structure in the excited state can be suppressed. Additionally, degradation or alteration of the compound due to carbon-deuterium bond dissociation can be suppressed. Furthermore, the formation of degradation products can be reduced. Moreover, the decrease in luminescence efficiency due to degradation products can be suppressed. Furthermore, a light-emitting device with high luminescence efficiency can be provided. Furthermore, a light-emitting device with a good operating life can be provided. Furthermore, changes in emission color associated with operation can be suppressed. Furthermore, a light-emitting device with high color purity can be provided. As a result, a novel light-emitting device with excellent convenience, usefulness, and reliability has been provided.

[0569] (Reference example) The comparative device 1 fabricated in this example has the same configuration as the light-emitting device 550X (see Figure 18).

[0570] Configuration of Comparison Device 1 Table 1 shows the configuration of comparative device 1. Note that it differs from light-emitting device 1 in that 2,9-di(1-naphthyl)-10-phenylanthracene (abbreviated as 2αN-αNPhA) is used instead of 2αN-αNPhA-d7. The structural formula of 2αN-αNPhA is shown below.

[0571] [ka]

[0572] 《Method for fabricating comparative device 1》 Comparative device 1, described in this reference example, was fabricated using a method comprising the steps outlined below. Note that the fabrication method for comparative device 1 differs from that of light-emitting device 1 in that 2αN-αNPhA was used instead of 2αN-αNPhA-d7 in the step of forming layer 111. Here, the differences will be explained in detail, and the parts using the same method will be based on the explanation above.

[0573] [Step 5] In the fifth step, layer 111 was formed on layer 112(2). Specifically, the material was co-deposited using the resistance heating method.

[0574] Layer 111 contains 2αN-αNPhA and 3,10PCA2Nbf(IV)-02 in a weight ratio of 2αN-αNPhA:3,10PCA2Nbf(IV)-02 = 1:0.015 and has a thickness of 25 nm. [Explanation of Symbols]

[0575] ELX Hikari ELX2 Light ELY Hikari hv light HM1 HOMO level HM2 HOMO level 103 units 103S Unit 103X Unit 103X2 Unit 103Y Unit 104 layers 104X layer 104XY gap 104Y layer 105 layers 105_2 layers 106 layers 106_1 layer 106_2 layers 111 layers 111X layer 111X2 layers 111Y layer 112 layers 112_2 layer 112X layer 112X2 layers 112Y layer 113 layers 113_2 layer 113X layer 113Y layer 114N layer 114P layer 114S layer 400 circuit boards 401 Electrode 403 EL layer 404 Electrode 405 sealant 406 Sealant 407 Sealing substrate 412 pads 420 IC chips 521 Insulating film 528 Insulating film 529 Insulating film 529XY insulating film 550S Photoelectric Conversion Device 550X Light-Emitting Device 550Y light-emitting device 551 Electrode 551S electrode 551X electrode 551XS Gap 551XY gap 551Y electrode 552 Electrode 552S electrode 552X electrode 552Y electrode 601 Source Line Drive Circuit 602 pixel section 603 Gate wire drive circuit 604 Sealing substrate 605 Sealant 607 Space 608 Wiring 609 External input terminal 610 element substrate 611 Switching FET 612 Current-Controlled FET 613 Electrode 614 Insulators 616 EL layer 617 Electrode 618 Light-emitting devices 623 FET 700 Display device 951 circuit board 952 Electrode 953 Insulating layer 954 Partition layer 955 EL layer 956 Electrode 1001 circuit board 1002 Underlying insulating film 1003 Gate Insulator 10:06 Guard Station 1007 🙏 1008 Gate 1020 Interlayer insulating film 1021 Interlayer insulating film 1022 Electrode 1024B Electrode 1024G electrode 1024R electrode 1024W electrode 1025 Bulkhead 1028 EL layer 1029 Electrode 1031 Sealing substrate 1032 Sealant 1033 Base material 1034B Colored layer 1034G colored layer 1034R colored layer 1035 Black Matrix 1036 Overcoat layer 1037 Interlayer insulating film 1040 pixel section 1041 Drive circuit section 1042 Peripheral area 2001 cabinet 2002 light source 2100 Robots 2102 Microphone 2103 Top camera 2104 Speaker 2105 Display 2106 Lower Camera 2107 Obstacle Sensor 2108 Moving mechanism 2110 Arithmetic equipment 3001 Lighting device 5000 cabinets 5001 Display section 5002 Display section 5003 Speaker 5004 LED Lamp 5006 Connection terminal 5007 Sensor 5008 Microphone 5012 Support part 5013 Earphones 5100 Cleaning Robot 5101 Display 5102 Camera 5103 Brush 5104 Operation Buttons 5120 Garbage 5140 Portable electronic devices 5200 display area 5201 Display area 5202 Display area 5203 Display area 7101 enclosure 7103 Display section 7105 Stand 7107 Display section 7109 Operation Keys 7110 Remote Control Unit 7201 Main Unit 7202 enclosure 7203 Display section 7204 Keyboard 7205 External connection port 7206 Pointing device 7210 Display section 7401 enclosure 7402 Display section 7403 Operation Buttons 7404 External connection port 7405 Speaker 7406 Microphone 9310 Mobile Information Terminal 9311 Display Panel 9313 Hinge 9315 enclosure

Claims

1. An organic compound represented by the general formula (G1). 【Chemical 1】 In the above general formula (G1), R １ to R ２６ at least one of which is deuterium, R １ to R ７ at least one of which is any one of a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted trialkylsilyl group, or a substituted or unsubstituted aryl group, R １ to R ７ others are each independently any one of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted trialkylsilyl group or a substituted or unsubstituted aryl group, R ８ to R ２６ is each independently any one of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted trialkylsilyl group or a substituted or unsubstituted aryl group, The alkyl group has 3 to 10 carbon atoms, The cycloalkyl group has 3 to 10 carbon atoms, The trialkylsilyl group has 3 to 12 carbon atoms, The aryl group has 6 to 25 carbon atoms.

2. A light-emitting device including the organic compound according to Claim 1 between a first electrode and a second electrode.

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