Organic compound
An organic compound with a benzo[h]quinazoline skeleton and heteroaromatic ring enhances electron transport, addressing efficiency and reliability issues in light-emitting devices, enabling low-voltage operation and improved performance.
Patent Information
- Application Number
- JP2025089150
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-05-30
- Filing Date
- 2025-05-28
- Publication Date
- 2025-12-11
AI Technical Summary
Existing organic light-emitting devices face challenges in achieving high emission efficiency, color purity, reliability, and low power consumption, with complex synthesis processes and high material costs hindering their performance and cost competitiveness.
Development of an organic compound with a benzo[h]quinazoline skeleton and a substituted or unsubstituted heteroaromatic ring bonded to a pyridine ring via an arylene group, which can be used in the n-type layer of a tandem light-emitting device, enhancing electron transport properties and allowing low-voltage operation.
The organic compound improves emission efficiency, color purity, and reliability of light-emitting devices while reducing power consumption, making them suitable for display and lighting applications.
Smart Images

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Figure 2025181780000074 
Figure 2025181780000075
Abstract
Description
[Technical Field]
[0001] One embodiment of the present invention relates to an organic compound, an organic semiconductor element, a light-emitting device, a photodiode sensor, a display module, a lighting module, a display device, an electronic device, a lighting device, and an electronic device. Note that one embodiment of the present invention is not limited to the above technical field. The technical field of one embodiment of the invention disclosed in this specification etc. relates to an object, a method, or a manufacturing method. Alternatively, one embodiment of the present invention relates to a process, a machine, manufacture, or a composition of matter. Therefore, more specifically, examples of the technical field of one embodiment of the present invention disclosed in this specification include semiconductor devices, display devices, liquid crystal display devices, lighting devices, power storage devices, memory devices, imaging devices, driving methods thereof, and manufacturing methods thereof. [Background technology]
[0002] Light-emitting devices (also known as organic EL elements), which contain organic compounds as light-emitting materials between a pair of electrodes, have properties such as being thin and lightweight, having high-speed response, and being driven at low voltages, and development of displays that use these elements is underway.
[0003] Furthermore, these light-emitting devices can be fabricated with a continuous two-dimensional light-emitting layer, enabling planar light emission, a feature that is difficult to achieve with point light sources such as incandescent light bulbs or LEDs, or linear light sources such as fluorescent lamps, making them highly useful as surface light sources for lighting applications.
[0004] Although displays and lighting devices using such light-emitting devices are suitable for various electronic devices, there is still room for improvement in their performance and cost competitiveness. Therefore, there is a daily demand for materials with better properties and easier handling, as well as easy synthesis methods for such materials.
[0005] Furthermore, for example, if the synthetic route of the material used in the light-emitting device is complicated, the cost of the raw material will rise significantly. Furthermore, there are problems such as the need for high temperature and pressure during synthesis to increase the yield of the material. Furthermore, there are problems such as the complicated purification process after the synthesis reaction, making it difficult to achieve high purity.
[0006] Patent Document 1 discloses a pyrimidine-based or triazine-based derivative, an electron transport material made of the same, and an organic electroluminescence device containing the same.
[0007] Furthermore, Patent Document 2 discloses an organic compound having two or three benzo[h]quinazoline rings and an organic electroluminescence device containing the same. [Prior art documents] [Patent documents]
[0008] [Patent Document 1] Japanese Patent Application Laid-Open No. 2009-184987 [Patent Document 2] Japanese Patent Application Laid-Open No. 2016-153400 Summary of the Invention [Problem to be solved by the invention]
[0009] An object of one embodiment of the present invention is to provide a novel organic compound.An object of one embodiment of the present invention is to provide a method for synthesizing the novel organic compound.An object of another embodiment of the present invention is to provide an organic compound that can be used in a light-emitting device.An object of one embodiment of the present invention is to provide a light-emitting device with high emission efficiency.An object of one embodiment of the present invention is to provide a light-emitting device with high color purity.An object of one embodiment of the present invention is to provide a light-emitting device with high reliability.An object of one embodiment of the present invention is to provide any one of a display device, an electronic device, and a lighting device with low power consumption.An object of one embodiment of the present invention is to provide any one of a display device, an electronic device, and a lighting device with high reliability.An object of one embodiment of the present invention is to provide any one of a display device, an electronic device, and a lighting device with high color purity.
[0010] The present invention is intended to solve at least one of the above problems. [Means for solving the problem]
[0011] One embodiment of the present invention is an organic compound having a first heteroaromatic ring, a second heteroaromatic ring, and a pyridine ring, wherein the first heteroaromatic ring is a benzo[h]quinazoline skeleton, and the second heteroaromatic ring is a substituted or unsubstituted heteroaromatic ring having 8 to 40 carbon atoms, and the second heteroaromatic ring is different from the first heteroaromatic ring in that the 2-position of the benzo[h]quinazoline skeleton is bonded to the 2-position of the pyridine ring and the second heteroaromatic ring is bonded to any one of the 3-position to the 6-position of the pyridine ring. Note that in the organic compound, the second heteroaromatic ring may be bonded to any one of the 3-position to the 6-position of the pyridine ring via an arylene group.
[0012] One embodiment of the present invention is an organic compound represented by general formula (G1-1).
[0013] [ka]
[0014] In general formula (G1-1), Ar1 represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, n1 represents an integer of 0 to 3, R 1 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, the heteroaromatic ring being different from the benzo[h]quinazoline skeleton and being bonded to the arylene group or the pyridine ring via a carbon-carbon bond; R 2 ~R 11 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
[0015] One embodiment of the present invention is an organic compound represented by general formula (G1-1), excluding an organic compound represented by general formula (N1).
[0016] [ka]
[0017] In the above general formula (G1-1), Ar 1 represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, n1 represents an integer of 0 to 3, R 1 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, and the heteroaromatic ring is bonded to the arylene group or the pyridine ring via a carbon-carbon bond; R 2 ~R 11 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
[0018] [ka]
[0019] In the general formula (N1), A represents a substituent having 3 to 30 carbon atoms and containing an aromatic ring or a heteroaromatic ring. 21 ~R 27each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms; and n is 2 or 3.
[0020] Alternatively, in the general formula (G1-1), n1 represents an integer of 0 to 3, and Ar 1 represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, R 1 represents any one of a pyridine ring, a pyrimidine ring, a triazine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, and a spiro[9H-fluorene-9,9'-[9H]xanthene] ring; R 2 ~R 11 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
[0021] One embodiment of the present invention is an organic compound represented by general formula (G1-2), excluding the organic compound represented by general formula (N1).
[0022] [ka]
[0023] In the general formula (G1-2), n2 and n3 represent integers of 0 to 3. When n2 is 0, n3 represents an integer of 1 to 3, and Ar 3 represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, R 3 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, and the heteroaromatic ring is bonded to the arylene group via a carbon-carbon bond; R 2 and R 5 ~R 11 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. When n3 is 0, n2 represents an integer of 1 to 3, and Ar 2represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, R 2 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, and the heteroaromatic ring is bonded to the arylene group via a carbon-carbon bond; R 3 and R 5 ~R 11 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
[0024] One embodiment of the present invention is an organic compound represented by general formula (G1-3), excluding the organic compound represented by general formula (N1).
[0025] [ka]
[0026] In the general formula (G1-3), n2 and n3 represent integers of 0 to 3. When n2 is 0, n3 represents an integer of 1 to 3, and Ar 3 represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, R 3 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, and the heteroaromatic ring is bonded to the arylene group via a carbon-carbon bond; R 2 and R 6 ~R 16 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. When n3 is 0, n2 represents an integer of 1 to 3, and Ar 2 represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, R 2 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, and the heteroaromatic ring is bonded to the arylene group via a carbon-carbon bond; R 3 and R 6 ~R 16each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
[0027] One embodiment of the present invention is an organic compound represented by general formula (G2-1), excluding the organic compound represented by general formula (N1).
[0028] [ka] In the above general formula (G2-1), R 1 ~R 4 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, provided that R 1 ~R 4 At least one of R represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, and the heteroaromatic ring is bonded to the pyridine ring via a carbon-carbon bond. 5 ~R 11 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
[0029] One embodiment of the present invention is an organic compound represented by general formula (G2-2), excluding the organic compound represented by general formula (N1).
[0030] [ka]
[0031] In the above general formula (G2-2), R 2 and R 3each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, provided that R 2 and R 3 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, and the heteroaromatic ring is bonded to the pyridine ring via a carbon-carbon bond. 5 ~R 11 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
[0032] One embodiment of the present invention is an organic compound represented by general formula (G2-3), excluding the organic compound represented by general formula (N1).
[0033] [ka]
[0034] In the above general formula (G2-3), R 2 and R 3 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, provided that R 2 and R 3 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, and the heteroaromatic ring is bonded to the pyridine ring via a carbon-carbon bond. 6 ~R 16 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
[0035] One embodiment of the present invention is an organic compound represented by the structural formula (100), the structural formula (106), the structural formula (204), or the structural formula (210).
[0036] [ka]
[0037] Another embodiment of the present invention is a display device including any of the above light-emitting devices.
[0038] Another embodiment of the present invention is an electronic device including any of the above light-emitting devices and a sensor, an operation button, a speaker, or a microphone.
[0039] Another embodiment of the present invention is a lighting device including the above-described light-emitting device and a housing. [Effects of the Invention]
[0040] According to one embodiment of the present invention, a novel organic compound can be provided. According to one embodiment of the present invention, a synthesis method for a novel organic compound can be provided. According to another embodiment of the present invention, an organic compound that can be used in a light-emitting device can be provided. According to another embodiment of the present invention, a light-emitting device with high emission efficiency can be provided. According to another embodiment of the present invention, a light-emitting device with high color purity can be provided. According to another embodiment of the present invention, a light-emitting device with high reliability can be provided. According to another embodiment of the present invention, a display device, an electronic device, or a lighting device with low power consumption can be provided. According to another embodiment of the present invention, a display device, an electronic device, or a lighting device with high reliability can be provided. According to another embodiment of the present invention, a display device, an electronic device, or a lighting device with high color purity can be provided.
[0041] Note that the description of these effects does not preclude the existence of other effects. Note that one embodiment of the present invention does not necessarily have all of these effects. Note that effects other than these will become apparent from the description in the specification, drawings, claims, etc., and it is possible to extract other effects from the description in the specification, drawings, claims, etc. [Brief explanation of the drawings]
[0042] [Figure 1] 1(A) and 1(B) are schematic diagrams of a light-emitting device. [Figure 2] 2A to 2E are diagrams illustrating the configuration of a light-emitting device. [Figure 3] 3A and 3B are a top view and a cross-sectional view of the light-emitting device. [Figure 4] 4A to 4E are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 5] 5A and 5B are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 6] 6A to 6D are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 7] 7A to 7C are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 8] 8A to 8C are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 9] 9A to 9C are cross-sectional views showing an example of a method for manufacturing a display device. [Figure 10] 10A to 10G are top views showing examples of pixel configurations. [Figure 11] 11A to 11I are top views showing examples of pixel configurations. [Figure 12] 12(A) and 12(B) are perspective views showing configuration examples of a display module. [Figure 13] 13(A) and 13(B) are cross-sectional views showing examples of the configuration of a display device. [Figure 14] FIG. 14 is a perspective view showing an example of the configuration of a display device. [Figure 15] FIG. 15 is a cross-sectional view showing an example of the configuration of a display device. [Figure 16] FIG. 16 is a cross-sectional view showing an example of the configuration of a display device. [Figure 17] Fig. 17(A) is a cross-sectional view showing an example of the configuration of a display device, Fig. 17(B) is a top view showing an example of the configuration of a pixel, and Fig. 17(C) is a top view showing an example of the configuration of an organic resin layer. [Figure 18] FIG. 18 is a cross-sectional view showing an example of the configuration of a display device. [Figure 19] Fig. 19(A) is a cross-sectional view showing a configuration example of a display device, Fig. 19(B) is a top view showing a configuration example of a pixel, and Fig. 19(C) is a top view showing a configuration example of a microlens. [Figure 20] 20A to 20D are diagrams showing examples of electronic devices. [Figure 21] 21A to 21F are diagrams showing examples of electronic devices. [Figure 22] 22A to 22G are diagrams showing examples of electronic devices. [Figure 23] FIG. 23 shows the 1H-NMR spectrum of the organic compound prepared in the example. [Figure 24] FIG. 24 is a diagram illustrating the configuration of a light-emitting device. [Figure 25] FIG. 25 is a diagram illustrating the luminance-current density characteristics of a light-emitting device. [Figure 26] FIG. 26 is a diagram illustrating the luminance-voltage characteristics of a light-emitting device. [Figure 27] FIG. 27 is a diagram illustrating the current efficiency-luminance characteristics of a light-emitting device. [Figure 28] FIG. 28 is a diagram illustrating the current density-voltage characteristics of a light-emitting device. [Figure 29] FIG. 29 is a diagram illustrating the electroluminescence spectrum of the light-emitting device. [Figure 30] FIG. 30 is a diagram illustrating the PL emission spectrum of the organic compound used in the sample. [Figure 31] FIG. 31(A) is a diagram illustrating the emission spectrum of an organic compound used in a light-emitting device, and FIG. 31(B) is a diagram illustrating the absorption spectrum of an organic compound used in a light-emitting device. [Figure 32] FIG. 32 is a diagram illustrating the configuration of a light-emitting device. [Figure 33] FIG. 33 is a diagram illustrating the luminance-current density characteristics of a light-emitting device. [Figure 34] FIG. 34 is a diagram illustrating the luminance-voltage characteristics of a light-emitting device. [Figure 35] FIG. 35 is a diagram illustrating the current efficiency-luminance characteristics of a light-emitting device. [Figure 36] FIG. 36 is a diagram illustrating the current density-voltage characteristics of a light-emitting device. [Figure 37] FIG. 37 is a diagram illustrating the electroluminescence spectrum of the light-emitting device. [Figure 38] FIG. 38 is a diagram illustrating the reliability characteristics of a light-emitting device. [Figure 39] FIG. 39 is a diagram illustrating the luminance-current density characteristics of a light-emitting device. [Figure 40] FIG. 40 is a diagram illustrating the luminance-voltage characteristics of a light-emitting device. [Figure 41] FIG. 41 is a diagram illustrating the current efficiency-luminance characteristics of a light-emitting device. [Figure 42] FIG. 42 is a diagram illustrating the current density-voltage characteristics of a light-emitting device. [Figure 43] FIG. 43 is a diagram illustrating the electroluminescence spectrum of the light-emitting device. [Figure 44] FIG. 44 is a diagram illustrating the reliability characteristics of a light-emitting device. [Figure 45] FIG. 45 shows the 1H-NMR spectrum of the organic compound prepared in the example. [Figure 46] FIG. 46 shows the 1H-NMR spectrum of the organic compound prepared in the example. [Figure 47] FIG. 47 shows the 1H-NMR spectrum of the organic compound prepared in the example. [Figure 48] FIG. 48 is a diagram illustrating the luminance-current density characteristics of a light-emitting device. [Figure 49] FIG. 49 is a diagram illustrating the luminance-voltage characteristics of a light-emitting device. [Figure 50] FIG. 50 is a diagram illustrating the current efficiency-luminance characteristics of a light-emitting device. [Figure 51] FIG. 51 is a diagram illustrating the current density-voltage characteristics of a light-emitting device. [Figure 52] FIG. 52 is a diagram illustrating the electroluminescence spectrum of the light-emitting device. [Figure 53] FIG. 53 is a diagram illustrating the reliability characteristics of a light-emitting device. [Figure 54] FIG. 54 is a diagram illustrating the luminance-current density characteristics of a light-emitting device. [Figure 55] FIG. 55 is a diagram illustrating the luminance-voltage characteristics of a light-emitting device. [Figure 56] FIG. 56 is a diagram illustrating the current efficiency-luminance characteristics of a light-emitting device. [Figure 57] FIG. 57 is a diagram illustrating the current density-voltage characteristics of a light-emitting device. [Figure 58] FIG. 58 is a diagram illustrating the electroluminescence spectrum of the light-emitting device. [Figure 59] FIG. 59 is a diagram illustrating the luminance-current density characteristics of a light-emitting device. [Figure 60] FIG. 60 is a diagram illustrating the luminance-voltage characteristics of a light-emitting device. [Figure 61] FIG. 61 is a diagram illustrating the current efficiency-luminance characteristics of a light-emitting device. [Figure 62] FIG. 62 is a diagram illustrating the current density-voltage characteristics of a light-emitting device. [Figure 63] FIG. 63 is a diagram illustrating the electroluminescence spectrum of the light-emitting device. [Figure 64] FIG. 64 is a diagram illustrating the reliability characteristics of a light-emitting device. DETAILED DESCRIPTION OF THE INVENTION
[0043] Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. However, the present invention is not limited to the following description, and it will be readily understood by those skilled in the art that various changes in form and details can be made without departing from the spirit and scope of the present invention. Therefore, the present invention should not be interpreted as being limited to the description of the embodiments shown below.
[0044] In this specification, etc., a device fabricated using a metal mask or an FMM (fine metal mask, high-resolution metal mask) may be referred to as a device with an MM (metal mask) structure. In addition, in this specification, etc., a device fabricated without using a metal mask or an FMM may be referred to as a device with an MML (metal maskless) structure.
[0045] (Embodiment 1) In this embodiment, an organic compound which is one embodiment of the present invention will be described.
[0046] <Examples of organic compounds> An organic compound according to one embodiment of the present invention includes a first heteroaromatic ring, a second heteroaromatic ring, and a pyridine ring. The first heteroaromatic ring has a benzo[h]quinazoline skeleton. The second heteroaromatic ring is a substituted or unsubstituted heteroaromatic ring having 8 to 40 carbon atoms and is different from the first heteroaromatic ring. The 2-position of the benzo[h]quinazoline skeleton is bonded to the 2-position of the pyridine ring. The second heteroaromatic ring is bonded to any one of the 3- to 6-positions of the pyridine ring or to any one of the 3- to 6-positions of the pyridine ring via an arylene group.
[0047] That is, the organic compound of one embodiment of the present invention is an organic compound in which a benzo[h]quinazoline skeleton and a heteroaromatic ring other than the benzo[h]quinazoline skeleton are bonded to a pyridine ring. Alternatively, the organic compound of one embodiment of the present invention is an organic compound in which a benzo[h]quinazoline skeleton and a heteroaromatic ring other than the benzo[h]quinazoline skeleton are bonded to a pyridine ring via an arylene group.
[0048] When mixed with a metal or a metal compound, the organic compound of one embodiment of the present invention can be coordinately bonded to the nitrogen atom of the pyridine in the 2-(2-pyridyl)benzo[h]quinazoline skeleton and one of the nitrogen atoms of the benzo[h]quinazoline in a chelated form. Therefore, when mixed with a metal or a metal compound, the organic compound of one embodiment of the present invention can stabilize the metal or metal compound that functions as an electron donor, and therefore can be suitably used for an n-type layer in an intermediate layer of a tandem light-emitting device. Thus, the organic compound of one embodiment of the present invention is suitable as a material for forming the n-type layer in an intermediate layer of a tandem light-emitting device. Therefore, in the case of a tandem light-emitting device that requires a high driving voltage, the organic compound of one embodiment of the present invention is preferably used in an intermediate layer or an electron-transporting layer, because it can be driven at a low voltage.
[0049] Furthermore, the organic compound of one embodiment of the present invention also has a heteroaromatic ring other than the benzo[h]quinazoline skeleton. The heteroaromatic ring can impart a function to the organic compound that is not included in the function of the benzo[h]quinazoline skeleton. In other words, it is easy to design an organic compound according to desired properties.
[0050] The heteroaromatic ring can be broadly classified into a π-electron-deficient heteroaromatic ring and a π-electron-rich heteroaromatic ring. For example, the LUMO (Lowest Unoccupied Molecular Orbital) level can be adjusted by using a π-electron-deficient heteroaromatic ring. In addition, the electron transport property can be further improved.
[0051] Alternatively, the π-electron-rich heteroaromatic ring can be used to adjust the HOMO (Highest Occupied Molecular Orbital) level and the LUMO level. Furthermore, the π-electron-rich heteroaromatic ring can improve the hole-transport property of the organic compound, so that the organic compound of one embodiment of the present invention can also be used in a functional layer other than an intermediate layer or an electron-transport layer.
[0052] Further, the organic compound of one embodiment of the present invention can be represented by the following general formulas (G1-1) to (G1-3) and (G2-1) to (G2-3).
[0053] <Organic Compound Example 1> One embodiment of the present invention is an organic compound represented by general formula (G1-1), excluding an organic compound represented by general formula (N1).
[0054] [ka]
[0055] However, in the above general formula (G1-1), Ar 1 represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, n1 represents an integer of 0 to 3, R 1 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, the heteroaromatic ring being bonded to an arylene group or a pyridine ring via a carbon-carbon bond; R 2 ~R 11 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
[0056] [ka]
[0057] In the general formula (N1), A represents a substituent having 3 to 30 carbon atoms and containing an aromatic ring or a heteroaromatic ring.21 ~R 27 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms; and n is 2 or 3.
[0058] In addition, in the general formula (G1-1), by bonding a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms to the pyridine ring, heat resistance is improved, and deterioration of film quality in a process requiring heating can be suppressed.
[0059] In addition, in general formula (G1-1), the heteroaromatic ring can be bonded to an arylene group or a pyridine ring via a carbon-carbon bond to increase stability in the excited state.
[0060] Furthermore, by removing general formula (N1) from general formula (G1-1), the heteroaromatic ring having 3 to 40 carbon atoms is other than a benzo[h]quinazoline skeleton. Therefore, in the organic compound represented by general formula (G1-1), when viewed from the center of the pyridine ring, the heteroaromatic ring and the benzo[h]quinazoline skeleton are asymmetric.
[0061] <Organic Compound Example 2> One embodiment of the present invention is an organic compound represented by general formula (G1-2), except for the organic compound represented by general formula (N1) shown in Example 1 of the organic compound.
[0062] [ka]
[0063] In the general formula (G1-2), n2 and n3 represent integers of 0 to 3. When n2 is 0, n3 represents an integer of 1 to 3, and Ar 3 represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, R 3 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, and the heteroaromatic ring is bonded to the arylene group via a carbon-carbon bond; R 2 and R 5~R 11 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. Alternatively, when n3 is 0, n2 represents an integer of 1 to 3, and Ar 2 represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, R 2 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, and the heteroaromatic ring is bonded to the arylene group via a carbon-carbon bond; R 3 and R 5 ~R 11 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
[0064] In general formula (G1-2), R 2 or R 3 When R is a heteroaromatic ring, the planarity of the entire molecule is increased, and the conjugation is extended, which is preferable because the electron transport property is improved. In addition, the molecular weight is increased, which is preferable because the heat resistance is improved.
[0065] <Organic Compound Example 3> Another embodiment of the present invention is an organic compound represented by general formula (G1-3), excluding the organic compound represented by general formula (N1) shown in Example 1 of the organic compound.
[0066] [ka]
[0067] In the general formula (G1-3), n2 and n3 represent integers of 0 to 3. When n2 is 0, n3 represents an integer of 1 to 3, and Ar 3 represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, R 3 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, and the heteroaromatic ring is bonded to the arylene group via a carbon-carbon bond; R2 and R 6 ~R 16 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. Alternatively, when n3 is 0, n2 represents an integer of 1 to 3, and Ar 2 represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, R 2 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, and the heteroaromatic ring is bonded to the arylene group via a carbon-carbon bond; R 3 and R 6 ~R 16 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
[0068] R in general formula (G1-2) 5 The general formula (G1-3) in which a phenyl group is substituted is preferred because it stabilizes the molecular structure.
[0069] <Organic Compound Example 4> One embodiment of the present invention is an organic compound represented by general formula (G2-1), except for the organic compound represented by general formula (N1) shown in Example 1 of the organic compound.
[0070] [ka]
[0071] However, in the above general formula (G2-1), R 1 ~R 4 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, provided that R 1 ~R 4At least one of R represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, and the heteroaromatic ring is bonded to the pyridine ring via a carbon-carbon bond. 5 ~R 11 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
[0072] In general formula (G2-1), R 1 ~R 4 By containing a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms in any one of the above, the molecular weight increases, the heat resistance improves, and deterioration of the film quality in a process requiring heating can be suppressed.
[0073] <<Organic Compound Example 5>> One embodiment of the present invention is an organic compound represented by general formula (G2-2), except for the organic compound represented by general formula (N1) shown in Example 1 of the organic compound.
[0074] [ka]
[0075] However, in the above general formula (G2-2), R 2 and R 3 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, provided that R 2 and R 3 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, and the heteroaromatic ring is bonded to the pyridine ring via a carbon-carbon bond. 5 ~R 11 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
[0076] In general formula (G2-2), R 2 or R 3 When R is a heteroaromatic ring, the planarity of the entire molecule is increased, and the conjugation is extended, which improves the electron transport property. In addition, the molecular weight is increased, which improves the heat resistance.
[0077] <<Example 6 of organic compounds>> Another embodiment of the present invention is an organic compound represented by general formula (G2-3), excluding the organic compound represented by general formula (N1) shown in Example 1 of the organic compound.
[0078] [ka]
[0079] However, in the above general formula (G2-3), R 2 and R 3 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, provided that R 2 and R 3 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, and the heteroaromatic ring is bonded to the pyridine ring via a carbon-carbon bond. 6 ~R 16 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
[0080] R in general formula (G2-2) 5 The general formula (G2-3) in which a phenyl group is substituted is preferred because it stabilizes the molecular structure.
[0081] In the general formulae (G1-1) to (G1-3), examples of the arylene group represented by Ar include a phenylene group, a biphenyl-diyl group, a naphthalene-diyl group, a fluorene-diyl group, an anthracene-diyl group, a phenanthrene-diyl group, a terphenyl-diyl group, a triphenylene-diyl group, a tetracene-yl group, a benzanthracene-diyl group, a spirobi[9H-fluorene]-diyl group, a dibenzofuran-diyl group, and a dibenzothiophene-diyl group.
[0082] In addition, in the general formulae (G1-1) to (G1-3) and the general formulae (G2-1) to (G2-3), R n Specific examples of the substituent represented by (n is an arbitrary integer) are shown below.
[0083] Examples of the heteroaromatic ring having 3 to 40 carbon atoms include π-electron-deficient heteroaromatic rings such as pyridine, pyrimidine, triazine, quinoline, isoquinoline, fullerazine, naphthyridine, quinoxaline, quinazoline, cinnoline, phenanthridine, acridine, phenanthroline, phenazine, dibenzo[f,h]quinoline, dibenzo[f,h]quinoxaline, and dibenzo[f,h]quinazoline, as well as π-electron-rich heteroaromatic rings such as dibenzofuran, dibenzothiophene, carbazole, thianthrene, xanthene, thioxanthene, phenoxathiin, spiro[9H-fluorene-9,9′-[9H]xanthene], spiro[9H-fluorene-9,9′-[9H]thioxanthene], and dibenzo[f,h]quinoline. The heteroaromatic ring can be appropriately selected depending on the properties required for the organic compound.
[0084] Therefore, the organic compound of one embodiment of the present invention can be used not only for the electron-transport layer but also for functional layers other than the electron-transport layer, such as an intermediate layer.
[0085] Among the heteroaromatic rings described above, it is preferable to use a heteroaromatic ring having 8 to 40 carbon atoms. A carbon number of 8 or more is preferable because the glass transition temperature (Tg) can be increased to 100°C or higher, a carbon number of 12 or more is more preferable because the glass transition temperature (Tg) can be increased to 120°C or higher, and a carbon number of 25 or more is even more preferable because the glass transition temperature (Tg) can be increased to 150°C or higher.
[0086] Furthermore, when a heteroaromatic ring having 3 to 7 carbon atoms is used, it is preferable that it has a substituent. In particular, the above-mentioned effects can be achieved by making the total number of carbon atoms in the heteroaromatic ring and the carbon atoms in the substituent 8 or more. Specific examples of heteroaromatic rings having 3 to 7 carbon atoms and having a substituent include triazines having a substituent with 3 or more carbon atoms. Other examples include pyrimidines, pyrazines, and pyridazines having a substituent with 4 or more carbon atoms. Other examples include pyridines having a substituent with 5 or more carbon atoms.
[0087] Furthermore, when the heteroaromatic ring has a substituent, the substituent can be selected from an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, a cyano group, a hydroxyl group, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
[0088] When the substituent bonded to the aromatic hydrocarbon group is an alkyl group having 1 to 6 carbon atoms, specific examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, an n-hexyl group, etc. Furthermore, examples of a cycloalkyl group having 3 to 6 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc. Furthermore, examples of an aryl group having 6 to 13 carbon atoms include a phenyl group, a naphthyl group, a biphenyl group, a fluorenyl group, etc.
[0089] Specific examples of the alkyl group having 1 to 10 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a neopentyl group, a hexyl group, an isohexyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 2-ethylbutyl group, a 1,2-dimethylbutyl group, and a 2,3-dimethylbutyl group.
[0090] Specific examples of the aryl group having 6 to 30 carbon atoms include a phenyl group, a biphenyl group, a terphenyl group, a tolyl group, a xylyl group, an indenyl group, a naphthyl group, a binaphthyl group, a fluorenyl group, a spirofluorenyl group, a phenanthryl group, and a triphenylenyl group.
[0091] When the aryl group has a substituent, the substituent can be an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. Specific examples of the substituent include a cyano group and a hydroxyl group. The substituents bonded to the aromatic hydrocarbon groups described above can also be referenced.
[0092] In addition, in the general formulae (G1-1) to (G1-3) and the following general formulae (G2-1) to (G2-3), hydrogen may be replaced with deuterium as appropriate.
[0093] <Example> Next, specific examples of organic compounds according to one embodiment of the present invention, each having a structure represented by any of the above general formulas (G1-1) to (G1-3) and the following general formulas (G2-1) to (G2-3), are shown below.
[0094] [ka]
[0095] [ka]
[0096] [ka]
[0097] [ka]
[0098] The organic compounds represented by the above structural formulas (100) to (123) and the above structural formulas (200) to (223) are examples of organic compounds represented by any of the above general formulas (G1-1) to (G1-3) and the following general formulas (G2-1) to (G2-3); however, the organic compounds of one embodiment of the present invention are not limited thereto.
[0099] <Method for synthesizing organic compounds> A synthesis method for an organic compound represented by the following general formula (G1-1), which is an example of an organic compound according to one embodiment of the present invention, is described below. Note that various reactions can be applied to synthesize the organic compound represented by the general formula (G1-1), and the synthesis method is not limited to the following synthesis method.
[0100] [ka]
[0101] In the above general formula (G1-1), Ar 1 represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, n1 represents an integer of 0 to 3, R 1 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, and the heteroaromatic ring is bonded to an arylene group or a pyridine ring via a carbon-carbon bond; R 2 ~R 11each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
[0102] The organic compound represented by the general formula (G1-1) can be synthesized by a simple synthesis scheme such as the following synthesis scheme (s-1) or synthesis scheme (s-2).
[0103] [ka]
[0104] [ka]
[0105] In synthetic scheme (S-1), an amidine derivative (s1) and a chalcone derivative (s2) are reacted in an appropriate solvent and base to produce an organic compound, which is then reacted with a dehydrogenating agent in an appropriate solvent to produce a 2-(2-pyridyl)benzo[h]quinazoline derivative represented by general formula (s3). In this reaction, sodium hydroxide, potassium carbonate, or the like can be used as the base. Examples of dehydrogenating agents include benzoquinone derivatives and sulfur. When a benzoquinone derivative is used, chloranil or 2,3-dichloro-5,6-dicyano-p-benzoquinone is preferred.
[0106] In synthetic scheme (S-2), the 2-(2-pyridyl)benzo[h]quinazoline derivative (s3) synthesized in synthetic scheme (S-1) and compound (s4) are coupled by Suzuki-Miyaura reaction to obtain an organic compound represented by general formula (G1-1), which is one embodiment of the present invention.
[0107] In the synthetic scheme (S-1), R 2 ~R 11each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
[0108] In the synthetic scheme (S-1), X 1 represents a halogen or a triflate group, and in the case of a halogen, chlorine, bromine, or iodine is particularly preferred. However, the halogen is not limited to these, and X 1 may be an organoboron group, a boronic acid, an organotin group, or the like.
[0109] In the synthetic scheme (S-2), X 1 is the same as above. Also, X 2 represents a boronyl group (-B(OH)2). 2 When X is a boronyl group, a boronate ester or a cyclic triol borate salt may be used. However, the present invention is not limited to these. 2 may be chlorine, bromine, iodine, a triflate group, or the like.
[0110] In the compound (s4) of the synthetic scheme (S-2), Ar 1 represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, n1 represents an integer of 0 to 3, R 1 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms.
[0111] In the above general formula (G1-1), Ar 1 represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, n1 represents an integer of 0 to 3, R 1 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, and the heteroaromatic ring is bonded to an arylene group or a pyridine ring via a carbon-carbon bond; R 2 ~R 11 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
[0112] Examples of palladium catalysts that can be used in the coupling reaction represented by the above synthesis scheme (S-2) include palladium(II) acetate, tetrakis(triphenylphosphine)palladium(0), and bis(triphenylphosphine)palladium(II) dichloride.
[0113] Examples of the ligand for the palladium catalyst include 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, di(1-adamantyl)-N-butylphosphine, (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, tri(ortho-tolyl)phosphine, triphenylphosphine, and tricyclohexylphosphine.
[0114] Examples of the base that can be used in the coupling reaction represented by the above synthesis scheme (S-2) include organic bases such as potassium tert-butoxide, and inorganic bases such as potassium carbonate and sodium carbonate.
[0115] Examples of solvents that can be used in the coupling reaction represented by the above synthesis scheme (S-2) include toluene, xylene, mesitylene, benzene, tetrahydrofuran, dioxane, etc. However, the solvents that can be used are not limited to these.
[0116] The reaction performed in the above synthesis scheme (S-2) is not limited to the Suzuki-Miyaura reaction, but may also be the Buchwald-Hartwig reaction, the Migita-Kosugi-Still coupling reaction using an organotin compound, a coupling reaction using a Grignard reagent, the Ullmann reaction using copper or a copper compound, a nucleophilic substitution reaction, or the like.
[0117] Various types of the compounds (s1), (s2), and (s4) used in the synthetic schemes (S-1) and (S-2) are commercially available or can be synthesized, so that many types of organic compounds represented by general formula (G1-1) can be synthesized. Therefore, the organic compounds of one embodiment of the present invention are characterized by a wide variety.
[0118] The organic compound of one embodiment of the present invention can be synthesized as described above; however, the present invention is not limited thereto, and the compound may be synthesized by other synthesis methods.
[0119] This embodiment mode can be used in any combination with other embodiment modes and examples.
[0120] (Embodiment 2) In this embodiment mode, a structure of a light-emitting device using the organic compound shown in Embodiment Mode 1 will be described.
[0121] Displays using organic EL elements (hereinafter also referred to as light-emitting devices) as display elements (organic EL displays) have been in practical use for some time. To achieve full-color display, such displays typically have pixels that emit light of at least three colors: red, green, and blue.
[0122] A light-emitting device is provided for each of the pixels for each emission color, and in a side-by-side type, or so-called color-coded display, each light-emitting device has a different light-emitting material depending on the emission color of the corresponding pixel.
[0123] The organic compound described in embodiment 1 has good carrier transport properties, particularly excellent electron transport properties, and therefore can be suitably used as a carrier transport layer, particularly an electron transport layer, an electron injection layer, or a host material in a light-emitting device.
[0124] One embodiment of the present invention provides a light-emitting device using the organic compound described in Embodiment 1 as an electron-transporting material or the organic compound described in Embodiment 1 as a host material.
[0125] Furthermore, when the organic compound of one embodiment of the present invention is used in a layer in contact with the anode side of a charge generation layer used in a tandem light-emitting device or the like, the degree of crosstalk can be reduced, and a display device with high display quality can be easily provided. The charge generation layer will be described in detail later in the description of the light-emitting device.
[0126] Therefore, one embodiment of the present invention provides a tandem light-emitting device using the organic compound described in Embodiment 1 as a material for an intermediate layer of the device.
[0127] <Example of light-emitting device configuration> 1A is a schematic cross-sectional view of a light-emitting device 10 of one embodiment of the present invention. The light-emitting device 10 includes a pair of electrodes (a first electrode 101 and a second electrode 102) and an organic compound layer 103 provided between the pair of electrodes. The organic compound layer 103 includes at least a light-emitting layer 113.
[0128] The organic compound layer 103 shown in FIG. 1A includes functional layers such as a hole-injection layer 111, a hole-transport layer 112, an electron-transport layer 114, and an electron-injection layer 115 in addition to the light-emitting layer 113.
[0129] In the present embodiment, the first electrode 101 of the pair of electrodes is described as an anode and the second electrode 102 as a cathode, but the configuration of the light-emitting device 10 is not limited to this. That is, the first electrode 101 may be the cathode and the second electrode 102 may be the anode, and the layers between the electrodes may be stacked in the reverse order. That is, the stacking order may be, from the anode side, the hole injection layer 111, the hole transport layer 112, the light-emitting layer 113, the electron transport layer 114, and the electron injection layer 115.
[0130] 1A, the organic compound layer 103 may have at least one selected from a hole-injection layer 111, a hole-transport layer 112, an electron-transport layer 114, and an electron-injection layer 115. Alternatively, the organic compound layer 103 may have a functional layer having a function of reducing a hole- or electron-injection barrier, improving hole- or electron-transport properties, inhibiting hole- or electron-transport properties, suppressing quenching caused by an electrode, or the like. Each functional layer may be a single layer or may have a stacked structure of multiple layers.
[0131] Fig. 1(B) is a cross-sectional view schematically illustrating an example of the light-emitting layer 113 shown in Fig. 1(A). The light-emitting layer 113 shown in Fig. 1(B) includes a host material 118 (organic compounds 118_1 and 118_2) and a guest material 119 (light-emitting substance).
[0132] A light-emitting organic compound may be used as the guest material 119, and the light-emitting organic compound is preferably a substance that can emit phosphorescence (hereinafter also referred to as a phosphorescent compound).
[0133] In the light-emitting layer 113, the host material 118 is present in the largest amount by weight, and the guest material 119 is dispersed in the host material 118. As described above, the lowest triplet excitation energy level (T1 level) of the host material 118 (organic compound 118_1 and organic compound 118_2) of the light-emitting layer 113 is preferably higher than the T1 level of the guest material 119 of the light-emitting layer 113.
[0134] The host material 118 (organic compound 118_1 and organic compound 118_2) in the light-emitting layer 113 preferably forms an exciplex (also called an exciplex). Note that an exciplex is an excited state consisting of two or more substances, and in the case of photoexcitation, it is formed when one substance in an excited state interacts with the other substance in a ground state.
[0135] <Basic structure of light-emitting devices> The basic structure of a light-emitting device will be described in more detail below with reference to Figures 2(A) to 2(E). Figure 2(A) shows a light-emitting device having a structure (single structure) in which an organic compound layer (also called an EL layer) including a light-emitting layer is sandwiched between a pair of electrodes. Specifically, the light-emitting device has a structure in which an organic compound layer 103 is sandwiched between a first electrode 101 and a second electrode 102.
[0136] 2B shows a light-emitting device having a stacked structure (tandem structure) in which a plurality of organic compound layers (103a, 103b) (two layers in FIG. 2B) are disposed between a pair of electrodes and a charge generation layer 106 is disposed between the organic compound layers. A light-emitting device having a tandem structure can realize a highly efficient light-emitting device without changing the amount of current.
[0137] The charge generation layer 106 has a function of injecting electrons into one organic compound layer (103a or 103b) and injecting holes into the other organic compound layer (103b or 103a) when a potential difference is generated between the first electrode 101 and the second electrode 102. Therefore, in FIG. 2B, when a voltage is applied to the first electrode 101 so that the potential thereof is higher than that of the second electrode 102, electrons are injected from the charge generation layer 106 into the organic compound layer 103a and holes are injected into the organic compound layer 103b.
[0138] From the viewpoint of light extraction efficiency, the charge generation layer 106 is preferably transparent to visible light (specifically, the visible light transmittance of the charge generation layer 106 is 40% or more). The charge generation layer 106 functions even if it has lower conductivity than the first electrode 101 and the second electrode 102.
[0139] FIG. 2C shows a stacked structure of the organic compound layer 103 of the light-emitting device according to one embodiment of the present invention. In this case, the first electrode 101 functions as an anode, and the second electrode 102 functions as a cathode. The organic compound layer 103 has a structure in which a hole injection layer 111, a hole transport layer 112, a light-emitting layer 113, an electron transport layer 114, and an electron injection layer 115 are sequentially stacked over the first electrode 101. The light-emitting layer 113 may have a stacked structure of a plurality of light-emitting layers emitting different light colors. For example, a light-emitting layer containing a red light-emitting substance, a light-emitting layer containing a green light-emitting substance, and a light-emitting layer containing a blue light-emitting substance may be stacked, or a layer containing a carrier-transporting material may be interposed between the light-emitting layers. Alternatively, a light-emitting layer containing a yellow light-emitting substance and a light-emitting layer containing a blue light-emitting substance may be combined. However, the stacked structure of the light-emitting layer 113 is not limited to the above. For example, the light-emitting layer 113 may have a structure in which multiple light-emitting layers emitting the same light-emitting color are stacked. For example, a first light-emitting layer containing a blue light-emitting substance and a second light-emitting layer containing a blue light-emitting substance are stacked, or a layer containing a carrier-transporting material is interposed between the layers. A structure in which multiple light-emitting layers emitting the same light-emitting color are stacked may have higher reliability than a single-layer structure. Even in the case of a tandem structure as shown in FIG. 2B, in which multiple light-emitting layers are provided, each light-emitting layer is stacked in order from the anode side as described above. Furthermore, when the first electrode 101 is a cathode and the second electrode 102 is an anode, the stacking order of the organic compound layers 103 is reversed. Specifically, the structure is such that 111 on the first electrode 101, which is a cathode, is an electron injection layer, 112 is an electron transport layer, 113 is a light-emitting layer, 114 is a hole transport layer, and 115 is a hole injection layer.
[0140] The light-emitting layer 113 included in the organic compound layers (103, 103a, 103b) each contains a light-emitting substance and an appropriate combination of multiple substances, and can be configured to emit fluorescent or phosphorescent light of a desired emission color. The light-emitting layer 113 may also have a stacked structure that emits different light colors. In this case, different materials may be used for the light-emitting substance and other substances used in each stacked light-emitting layer. Alternatively, a structure in which different light-emitting colors are emitted from the multiple organic compound layers (103a, 103b) shown in Figure 2(B) may also be used. In this case, different materials may be used for the light-emitting substance and other substances used in each light-emitting layer.
[0141] In addition, in a light-emitting device according to one embodiment of the present invention, for example, the first electrode 101 shown in FIG. 2C may be a reflective electrode, the second electrode 102 may be a semi-transmissive and semi-reflective electrode, and a micro-optical resonator (microcavity) structure may be formed. This allows light emitted from the light-emitting layer 113 included in the organic compound layer 103 to resonate between the two electrodes, thereby enhancing the intensity of light emitted from the second electrode 102. Therefore, high definition can be easily achieved. Furthermore, the intensity of light emitted from a specific wavelength in the front direction can be enhanced, thereby reducing power consumption.
[0142] When the first electrode 101 of the light-emitting device is a reflective electrode having a laminated structure of a reflective conductive material and a light-transmitting conductive material (transparent conductive film), optical adjustment can be performed by controlling the film thickness of the transparent conductive film. Specifically, it is preferable to adjust the optical distance (product of film thickness and refractive index) between the first electrode 101 and the second electrode 102 to mλ / 2 (where m is an integer of 1 or greater) or in the vicinity thereof, for the wavelength λ of light obtained from the light-emitting layer 113.
[0143] Furthermore, in order to amplify the desired light (wavelength: λ) obtained from the light-emitting layer 113, it is preferable to adjust the optical distance from the first electrode 101 to the region (light-emitting region) in the light-emitting layer 113 where the desired light is obtained and the optical distance from the second electrode 102 to the region (light-emitting region) in the light-emitting layer 113 where the desired light is obtained to be (2m'+1)λ / 4 (where m' is an integer of 1 or greater) or close to that. Note that the light-emitting region here refers to the recombination region of holes and electrons in the light-emitting layer 113.
[0144] By performing such optical adjustment, the spectrum of the specific monochromatic light obtained from the light-emitting layer 113 can be narrowed, and light emission with good color purity can be obtained.
[0145] In the above case, the optical distance between the first electrode 101 and the second electrode 102 can be strictly defined as the total thickness from the reflective region of the first electrode 101 to the reflective region of the second electrode 102. However, since it is difficult to precisely determine the reflective regions of the first electrode 101 and the second electrode 102, the above-mentioned effect can be sufficiently achieved by assuming any position of the first electrode 101 and the second electrode 102 as the reflective region. Furthermore, the optical distance between the first electrode 101 and the light-emitting layer from which desired light is obtained can be strictly defined as the optical distance between the reflective region of the first electrode 101 and the light-emitting region of the light-emitting layer from which desired light is obtained. However, since it is difficult to precisely determine the reflective region of the first electrode 101 and the light-emitting region of the light-emitting layer from which desired light is obtained, the above-mentioned effect can be sufficiently achieved by assuming any position of the first electrode 101 as the reflective region and any position of the light-emitting layer from which desired light is obtained as the light-emitting region.
[0146] The light-emitting device shown in Figure 2(D) has a tandem structure. The tandem structure allows the device to emit light with high brightness. Furthermore, the tandem structure can reduce the current required to obtain the same brightness compared to a single structure, thereby improving reliability. Furthermore, power consumption can be reduced.
[0147] The light-emitting device shown in FIG. 2(E) is an example of the tandem-structure light-emitting device shown in FIG. 2(B). As shown in the figure, the light-emitting device has a structure in which three organic compound layers (103a, 103b, 103c) are stacked with charge generation layers (106a, 106b) sandwiched between them. Each of the three organic compound layers (103a, 103b, 103c) has a light-emitting layer (113a, 113b, 113c), and the light-emitting colors of the light-emitting layers can be freely combined. For example, the light-emitting layer 113a can be blue, the light-emitting layer 113b can be red, green, or yellow, and the light-emitting layer 113c can be blue. Alternatively, the light-emitting layer 113a can be red, the light-emitting layer 113b can be blue, green, or yellow, and the light-emitting layer 113c can be red.
[0148] In the light-emitting device according to one embodiment of the present invention, at least one of the first electrode 101 and the second electrode 102 is a light-transmitting electrode (such as a transparent electrode or a semi-transmitting / semi-reflective electrode). When the light-transmitting electrode is a transparent electrode, the visible light transmittance of the transparent electrode is 40% or more. In addition, when the semi-transmitting / semi-reflective electrode is used, the visible light reflectance of the semi-transmitting / semi-reflective electrode is 20% or more and 80% or less, preferably 40% or more and 70% or less. Furthermore, these electrodes have a resistivity of 1×10 -2 It is preferable to set it to Ωcm or less.
[0149] In the above-described light-emitting device according to one embodiment of the present invention, when one of the first electrode 101 and the second electrode 102 is a reflective electrode (a reflective electrode), the reflectivity of the reflective electrode for visible light is set to 40% to 100%, preferably 70% to 100%. -2 It is preferable to set it to Ωcm or less.
[0150] <Specific structure of light-emitting device> Next, a specific structure of a light-emitting device according to one embodiment of the present invention will be described. Here, a tandem structure will be described with reference to FIG. 2D. The single-structure light-emitting devices shown in FIGS. 2A and 2C also have the same organic compound layer structure. When the light-emitting device shown in FIG. 2D has a microcavity structure, the first electrode 101 is formed as a reflective electrode, and the second electrode 102 is formed as a semi-transmissive and semi-reflective electrode. Therefore, a single or multiple desired electrode materials can be used to form a single layer or a stacked layer. The second electrode 102 is formed by selecting an appropriate material after the organic compound layer 103b is formed.
[0151] <Light-emitting device materials> <Light-emitting layer> The light-emitting layers (113, 113a, 113b) are layers containing a light-emitting substance. Light-emitting substances that can be used for the light-emitting layers (113, 113a, 113b) include substances that emit light of colors such as blue, purple, blue-purple, green, yellow-green, yellow, orange, and red. When multiple light-emitting layers are provided, different light-emitting substances can be used for each light-emitting layer to produce different light-emitting colors (for example, white light emission obtained by combining complementary light-emitting colors). Furthermore, a stacked structure in which each light-emitting layer contains different light-emitting substances may be used.
[0152] Furthermore, the light-emitting layers (113, 113a, 113b) may contain one or more organic compounds (host materials, etc.) in addition to the light-emitting substance (guest material).
[0153] 1B can be used as the light-emitting layer 113. In the light-emitting layer 113, the host material 118 is present in the largest amount by weight, and the guest material 119 (phosphorescent compound) is dispersed in the host material 118. The T1 level of the host material 118 (organic compound 118_1 and organic compound 118_2) of the light-emitting layer 113 is preferably higher than the T1 level of the guest material 119 of the light-emitting layer 113.
[0154] The lowest triplet excitation energy level (T1 level) can be calculated from the emission edge obtained by measuring the emission spectrum (phosphorescence spectrum) at a low temperature (e.g., 10 K) using a thin film of the sample. The sample form when measuring the emission spectrum of the luminescence center substance may be a thin film or a solution, but a solution is preferred from the viewpoint of verifying the state of isolated molecules. A solvent with relatively low polarity, such as toluene or chloroform, is preferred for the solution. When the luminescence center substance is a phosphorescent compound, the lowest triplet excitation energy level (T1 level) can be measured at a low temperature (e.g., 10 K) or room temperature (e.g., 298 K), and can be calculated from the emission edge obtained by measuring the emission spectrum (phosphorescence spectrum). The emission edge can be calculated by drawing a tangent at the point where the absolute value of the slope on the short-wavelength side of the peak (or shoulder peak) observed at the shortest wavelength of the emission spectrum (phosphorescence spectrum) is maximum, and then calculating the tangent from the intersection point of the tangent with the horizontal axis (wavelength) or the baseline.
[0155] Light-emitting substances that can be used as guest materials include, for example, substances that emit red light. Furthermore, as the substance that emits red light, a substance that emits phosphorescence, particularly an organometallic complex, is more preferable. Examples of such light-emitting substances include organometallic compounds having a pyrimidine skeleton, such as (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)]), and bis[4,6-di(naphthalen-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(d1npm)2(dpm)]). Iridium complexes, organometallic iridium complexes with a pyrazine skeleton such as (acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(tppr)2(dpm)]), and (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq)2(acac)]), tris(1-phenylisoquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(piq)3]), bis(1-phenylisoquinolinato-N,C 2’) iridium(III) acetylacetonate (abbreviated as [Ir(piq)2(acac)]), (3,7-diethyl-4,6-nonanedionato-κO4,κO6)bis[2,4-dimethyl-6-[7-(1-methylethyl)-1-isoquinolinyl-κN]phenyl-κC]iridium(III), and (3,7-diethyl-4,6-nonanedionato-κO4,κO6)bis[2,4-dimethyl-6-[5-(1-methylethyl)-2-quinolinyl-κN]phenyl-κC]iridium(III). In addition to iridium complexes, platinum complexes such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP) and rare earth metal complexes such as tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: [Eu(DBM)3(Phen)]) and tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: [Eu(TTA)3(Phen)]) are also useful. These complexes have emission peaks in the wavelength range from 600 nm to 700 nm. Organometallic iridium complexes with a pyrazine skeleton can emit red light with good chromaticity. Compounds in which some of the hydrogen atoms in these compounds are replaced with deuterium can also be used. Other known substances that exhibit red phosphorescence can also be used.
[0156] Furthermore, when a red light-emitting substance is not used as the light-emitting substance, or when light-emitting devices having different configurations are included in the same light-emitting device, the light-emitting substance may be a fluorescent light-emitting substance, a phosphorescent light-emitting substance, a substance exhibiting thermally activated delayed fluorescence (TADF), or any other light-emitting substance.
[0157] Examples of materials that can be used as a luminescent substance that emits fluorescent light in the light-emitting layer 113 include the following: In addition, other fluorescent luminescent substances can also be used.
[0158] 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl-9-anthryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), N,N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine )phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-diphenyl-N-[4-( 10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra-tert-butylperylene (abbreviation: TBP), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-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-carbazol-3-amine (abbreviated as 2PCAPPA), N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPAPPA), N,N,N',N',N'',N'',N''',N'''-octaphenyldibenzo[g,p]chrysene-2,7,10,15-tetraamine (abbreviated as DBC1), Coumarin 30, N-(9,10-diphenyl-2-anthryl)-N,9-Diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA) , 9,10-bis(biphenyl-2-yl)-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), Coumarin 545T, N,N'-diphenylquinacridone (abbreviation: DPQd), rubrene, 5,12-bis(biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BPT), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl-4H-pyra N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhTD), 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM1), 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhTD), Name: p-mPhAFD), 2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTB),6-Bis{2-[4-(dimethylamino)phenyl]ethenyl}-4H-pyran-4-ylidene)propanedinitrile (abbreviation: BisDCM), 2-{2,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: BisDCJTM), N,N'-diphenyl-N,N'-(1,6-pyren-diyl)bis[(6-phenylbenzo[b]naphtho]] Examples include N,N'-diphenyl-N,N'-bis(9-phenyl-9H-carbazol-2-yl)naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviation: 3,10PCA2Nbf(IV)-02), and 3,10-bis[N-(dibenzofuran-3-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10FrA2Nbf(IV)-02). In particular, condensed aromatic diamine compounds, such as pyrenediamine compounds, such as 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6BnfAPrn-03, are preferred because of their high hole-trapping properties and excellent luminous efficiency and reliability.
[0159] In addition, 5,9-diphenyl-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene (abbreviation: DABNA1), 9-(biphenyl-3-yl)-N,N,5,11-tetraphenyl-5H,9H-[1,4]benzazaborino[2,3,4-kl]phenazaborin-3-amine (abbreviation: DABNA2), 2,12-di(tert-butyl)-5,9-di(4-tert-butylphenyl)-N,N-diphenyl -5H,9H-[1,4]benzazaborino[2,3,4-kl]phenazaborin-7-amine (abbreviation: DPhA-tBu4DABNA), 2,12-di(tert-butyl)-N,N,5,9-tetra(4-tert-butylphenyl)-5H,9H-[1,4]benzazaborino[2,3,4-kl]phenazaborin-7-amine (abbreviation: tBuDPhA-tBu4DABNA), 2,12-di(tert-butyl)-5,9 -Di(4-tert-butylphenyl)-7-methyl-5H,9H-[1,4]benzazaborino[2,3,4-kl]phenazaborine (abbreviation: Me-tBu4DABNA), N7,N7,N13,N13,5,9,11,15-octaphenyl-5H,9H,11H,15H-[1,4]benzazaborino[2,3,4-kl][1,4]benzazaborino[4',3',2':4,5][1,4]benzazaborino[3,2 Nitrogen- and boron-containing condensed heteroaromatic compounds, such as [-b]phenazaborine-7,13-diamine (abbreviation: ν-DABNA) and 2-(4-tert-butylphenyl)benz[5,6]indolo[3,2,1-jk]benzo[b]carbazole (abbreviation: tBuPBibc), in particular compounds with a diaza-boranaphtho-anthracene skeleton, are suitable for use because they have a narrow emission spectrum and can emit blue light with good color purity.
[0160] In addition to these, 9,10,11-tris[3,6-bis(1,1-dimethylethyl)-9H-carbazolyl-9-yl]-2,5,15,18-tetrakis(1,1-dimethylethyl)indolo[3,2,1-de]indolo[3',2',1':8,1][1,4]benzazaborino[2,3,4-kl]phenazaborine (abbreviation: BBCz-G), 9,11-bis[ Compounds having an indole skeleton such as [3,6-bis(1,1-dimethylethyl)-9H-carbazolyl-9-yl]-2,5,15,18-tetrakis(1,1-dimethylethyl)indolo[3,2,1-de]indolo[3',2',1':8,1][1,4]benzazaborino[2,3,4-kl]phenazaborine (abbreviation: BBCz-Y) can be preferably used.
[0161] When a phosphorescent material is used as the light-emitting material in the light-emitting layer 113, examples of materials that can be used include the following.
[0162] Tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium(III) (abbreviation: [Ir(mpptz-dmp)3]), 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) organometallic iridium complexes with a 4H-triazole skeleton, such as tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(Mptz1-mp)3]) and tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Prptz1-Me)3]). Organometallic iridium complexes with a triazole skeleton, including fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpim)3]), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmpimpt-Me)3]), and tris(2-{1-[2,6-bis(1-methylethyl)phenyl]-1H-imidazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmpimpt-Me)3]). Organometallic iridium complexes with an imidazole skeleton, such as tris[(6-tert-butyl-3-phenyl-2H-imidazo[4,5-b]pyrazin-1-yl-κC2)phenyl-κC]iridium(III) (abbreviation: [Ir(cb)3]), and organometallic iridium complexes with a benzimidazolidene skeleton, such as bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’]iridium(III) picolinate (abbreviation: FIrpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N,C 2’}iridium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ Examples include organometallic iridium complexes with phenylpyridine derivatives containing electron-withdrawing groups, such as ]iridium(III) acetylacetonate (abbreviated as FIr(acac)), and platinum complexes such as (2-{3-[3-(3,5-di-tert-butylphenyl)benzimidazol-1-yl-2-ylidene-κC2]phenoxy-κC2}-9-(4-tert-butyl-2-pyridinyl-κN)carbazole-2,1-diyl-κC1)platinum(II) (abbreviated as PtON-TBBI). These compounds exhibit blue phosphorescence, with peak emission in the wavelength range from 440 nm to 520 nm. Compounds in which some of the hydrogen atoms in these compounds are replaced with deuterium can also be used.
[0163] Also, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)3]), tris(4-t-butyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonato)bis(6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2(acac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]), (acetylacetonato)bis[5-methyl-6- Organometallic iridium complexes with a pyrimidine skeleton, such as (2-methylphenyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm)2(acac)]) and (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)2(acac)]), organometallic iridium complexes with a pyrazine skeleton, such as (acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-Me)2(acac)]) and (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]), and tris(2-phenylpyridinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(ppy)3]), bis(2-phenylpyridinato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), tris(benzo[h]quinolinato)iridium(III) (abbreviation: [Ir(bzq)3]), tris(2-phenylquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(pq)3]), bis(2-phenylquinolinato-N,C 2’) iridium(III) acetylacetonate (abbreviation: [Ir(pq)2(acac)]), [2-d3-methyl-8-(2-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridinyl-κN2)phenyl-κC]iridium(III) (abbreviation: Ir(5mppy-d3)2(mbfpypy-d3)), {2-(methyl-d3)-8-[4-(1-methylethyl-1-d)-2-pyridinyl-κN]benzofuro[2,3-b]pyridin-7-yl-κC}bis{5-(methyl-d3)-2-[5 {2-(methyl-d3)-2-pyridinyl-κN]phenyl-κC}iridium(III) (abbreviated as Ir(5mtpy-d6)2(mbfpypy-iPr-d4)), [2-d3-methyl-(2-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviated as Ir(ppy)2(mbfpypy-d3)), [2-(4-d3-methyl-5-phenyl-2-pyridinyl-κN2)phenyl-κC]bis[2-(5-d3-methyl-2-pyridinyl-κN2)phenyl -κC]iridium(III) (abbreviation: [Ir(5mppy-d3)2(mdppy-d3)]), [2-methyl-(8-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(ppy)2(mbfpypy)), [2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(ppy)2(mdppy)), tris{2-[5-(methyl- In addition to organometallic iridium complexes with a pyridine skeleton, such as (2-{1-(5-tert-butylbiphenyl-2-yl)-4-[3-tert-butyl-5-(4-phenyl-2-pyridinyl-κN)phenyl-κC6]-2-benzimidazolyl-κN3}-4,6-di-tert-butylphenolato-κO)platinum(II) (abbreviation: Pt(tBudppymmtBubiz-tBubp)), [2-(4-(3,Examples include organometallic platinum complexes such as (5-di-tert-butylphenyl)-6-{3-[4-(5'-tert-butyl[1,1':3',1''-terphenyl]-2'-yl)-2-pyridinyl-κN]phenyl-κC2}-2-pyridinyl-κN)phenolato-κO]platinum(II) (abbreviated as Pt(4tButpppypyp-mmtBup)), and rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviated as [Tb(acac)3(Phen)]). These compounds primarily exhibit green phosphorescence, with peak emission in the wavelength range of 500 to 600 nm. Organometallic iridium complexes with a pyrimidine skeleton are particularly preferred because of their outstanding reliability and luminous efficiency. Compounds in which some of the hydrogen atoms in these compounds are replaced with deuterium atoms can also be used.
[0164] The red phosphorescent material described above can also be used. In addition to the phosphorescent compounds described above, known phosphorescent compounds may be selected and used.
[0165] TADF materials include fullerene and its derivatives, acridine and its derivatives, eosin derivatives, etc. Also available are metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd). Examples of the metal-containing porphyrin include 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)), and octaethylporphyrin-platinum chloride complex (PtCl2OEP), all of which are shown in the following structural formulas.
[0166]
change
[0167] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[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'-bicarbazole (abbreviation: PCCzTzn), 9-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-3,3'-bi-9H-carbazole (abbreviation: PCCzPTzn), and 2-[4-(10H-phenoxazin-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: PXZ), which are shown in the following structural formulas, are also available. Heterocyclic compounds having either or both of a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring, such as 3-[4-(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-dimethyl-9H-acridin-10-yl)-9H-xanthen-9-one (abbreviation: ACRXTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviation: DMAC-DPS), and 10-phenyl-10H,10'H-spiro[acridin-9,9'-anthracene]-10'-one (abbreviation: ACRSA), can also be used. The heterocyclic compound has a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring, and therefore has high electron transport and hole transport properties, and is therefore preferred. Among the skeletons having a π-electron-deficient heteroaromatic ring, pyridine skeleton, diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton), and triazine skeleton are preferred because they are stable and reliable. In particular, benzofuropyrimidine skeleton, benzothienopyrimidine skeleton, benzofuropyrazine skeleton, and benzothienopyrazine skeleton are preferred because they have high acceptor properties and good reliability. Furthermore, among the skeletons having a π-electron-rich heteroaromatic ring, acridine skeleton, phenoxazine skeleton, phenothiazine skeleton, furan skeleton, thiophene skeleton, and pyrrole skeleton are preferred because they are stable and reliable. Furthermore, a dibenzofuran skeleton is preferred as a furan skeleton, and a dibenzothiophene skeleton is preferred as a thiophene skeleton.Particularly preferred pyrrole skeletons include an indole skeleton, a carbazole skeleton, an indolocarbazole skeleton, a bicarbazole skeleton, and a 3-(9-phenyl-9H-carbazol-3-yl)-9H-carbazole skeleton. Substances in which a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring are directly bonded are particularly preferred because the electron-donating property of the π-electron-rich heteroaromatic ring and the electron-accepting property of the π-electron-deficient heteroaromatic ring are both enhanced, thereby reducing the energy difference between the S1 level and the T1 level, thereby enabling efficient thermally activated delayed fluorescence. Instead of the π-electron-deficient heteroaromatic ring, an aromatic ring bonded to an electron-withdrawing group such as a cyano group may be used. Examples of π-electron-rich skeletons that can be used include aromatic amine skeletons and phenazine skeletons. Examples of usable π-electron-deficient skeletons include a xanthene skeleton, a thioxanthene dioxide skeleton, an oxadiazole skeleton, a triazole skeleton, an imidazole skeleton, an anthraquinone skeleton, a boron-containing skeleton such as phenylborane or boranthrene, an aromatic ring or heteroaromatic ring having a nitrile group or a cyano group such as benzonitrile or cyanobenzene, a carbonyl skeleton such as benzophenone, a phosphine oxide skeleton, a sulfone skeleton, etc. In this way, a π-electron-deficient skeleton and a π-electron-rich skeleton can be used in place of at least one of a π-electron-deficient heteroaromatic ring and a π-electron-rich heteroaromatic ring.
[0168] [ka]
[0169] Alternatively, TADF materials may be used, which are capable of extremely fast and reversible intersystem crossing and emit light according to a thermal equilibrium model between singlet and triplet excited states. Such TADF materials have an extremely short emission lifetime (excitation lifetime) for TADF materials, and can suppress efficiency decline in the high-brightness region of light-emitting devices. Specific examples include materials with the molecular structure shown below.
[0170] [ka]
[0171] TADF materials are materials with a small difference between the S1 and T1 levels, and have the ability to convert triplet excitation energy to singlet excitation energy through reverse intersystem crossing. Therefore, triplet excitation energy can be upconverted to singlet excitation energy (reverse intersystem crossing) using a small amount of thermal energy, allowing for efficient generation of a singlet excited state. Triplet excitation energy can also be converted into light emission.
[0172] Furthermore, exciplexes (also known as exciplexes), which form an excited state with two types of substances, have an extremely small difference between the S1 and T1 levels and function as TADF materials that can convert triplet excitation energy into singlet excitation energy.
[0173] Note that the phosphorescence spectrum observed at low temperatures (for example, 77 K to 10 K) can be used as an indicator of the T1 level. For a TADF material, when a tangent line is drawn at the base of the short wavelength side of the fluorescence spectrum and the energy of the wavelength of the extrapolated line is defined as the S1 level, and a tangent line is drawn at the base of the short wavelength side of the phosphorescence spectrum and the energy of the wavelength of the extrapolated line is defined as the T1 level, the difference between the S1 level and the T1 level is preferably 0.3 eV or less, and more preferably 0.2 eV or less.
[0174] When a TADF material is used as a light-emitting material, the S1 level of the host material is preferably higher than the S1 level of the TADF material, and the T1 level of the host material is preferably higher than the T1 level of the TADF material.
[0175] As an electron-transporting material (corresponding to a first organic compound in one embodiment of the present invention) used as the host material, the organic compound described in Embodiment 1 is preferable. For example, a metal complex such as bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), or bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), or an organic compound having a π-electron-deficient heteroaromatic ring can be used. Examples of organic compounds having a π-electron-deficient heteroaromatic ring include 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 1,3-bis[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviation: CO11), 2,2′,2″-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2- Organic compounds containing heteroaromatic rings with an azole skeleton, such as [3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 4,6-bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-Bis[3-(dibenzothiophen-4-yl)phenyl]pyrimidine (abbreviated as 4,6mDBTP2Pm-II), 2,4-bis[4-(1-naphthyl)phenyl]-6-[4-(3-pyridyl)phenyl]pyrimidine (abbreviated as 2,4NP-6PyPPm), 6-(biphenyl-3-yl)-4-[3,5-bis(9H-carbazol-9-yl)phenyl]-2-phenylpyrimidine (abbreviated as 6mBP-4Cz2PPm), 4-[3,5-bis(9H-carbazol-9-yl)phenyl]-2-phenyl-6-(biphenyl-4-yl) Organic compounds containing heteroaromatic rings with a diazine skeleton, such as pyrimidine (abbreviation: 6BP-4Cz2PPm) and 7-[4-(9-phenyl-9H-carbazol-2-yl)quinazolin-2-yl]-7H-dibenzo[c,g]carbazole (abbreviation: PC-cgDBCzQz), organic compounds containing heteroaromatic rings with a pyridine skeleton, such as 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy) and 1,3,5-tri[(3-pyridyl)-phenyl-3-yl]benzene (abbreviation: TmPyPB), and organic compounds containing heteroaromatic rings with a pyridine skeleton, such as 2-[3 '-(9,9-dimethyl-9H-fluoren-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn), 2-(biphenyl-4-yl)-4-phenyl-6-(9,9'-spirobi[9H-fluoren]-2-yl)-1,3,5-triazine (abbreviation: BP-SFTzn), 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-8-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mBnfBPTzn), 2-{3-[3-(benzo[b] naphtho[1,2-d]furan-6-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mBnfBPTzn-02), 5-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-7,7-dimethyl-5H,7H-indeno[2,1-b]carbazole (abbreviation: mINc(II)PTzn), 2-[3'-(triphenylen-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mTpBPTzn), 3-[9-(4,6-diphenyl-1,3,Examples of suitable organic compounds include organic compounds containing a heteroaromatic ring having a triazine skeleton, such as [(5-triazin-2-yl)-2-dibenzofuranyl]-9-phenyl-9H-carbazole (abbreviation: PCDBfTzn) and 2-(biphenyl-3-yl)-4-phenyl-6-{8-[(1,1':4',1''-terphenyl)-4-yl]-1-dibenzofuranyl}-1,3,5-triazine (abbreviation: mBP-TPDBfTzn). Among the above, organic compounds containing a heteroaromatic ring having a diazine skeleton, organic compounds containing a heteroaromatic ring having a pyridine skeleton, and organic compounds containing a heteroaromatic ring having a triazine skeleton are preferred because of their high reliability. In particular, organic compounds containing a heteroaromatic ring having a diazine (pyrimidine and pyrazine) skeleton and organic compounds containing a heteroaromatic ring having a triazine skeleton have high electron-transporting properties and contribute to reducing driving voltage. In addition, the organic compound of Embodiment 1 can be used as an electron-transporting material used as a host material. ,
[0176] The hole transport material (corresponding to the second organic compound in one embodiment of the present invention) used as the host material can also be an organic compound having an amine skeleton or a π-electron-rich heteroaromatic ring. Examples of the organic compound having an amine skeleton or a π-electron-rich heteroaromatic ring include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminobiphenyl (abbreviation: TPD), N,N'-bis(9,9'-spirobi[9H-fluoren]-2-yl)-N,N'-diphenyl-4,4'-diaminobiphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenyl 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H -carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi[9H- compounds with an aromatic amine skeleton such as [N-fluorene]-2-amine (abbreviation: PCBASF); compounds with a carbazole skeleton such as 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviation: CzTP), and 9,9'-diphenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCP);Examples of suitable compounds include compounds having a thiophene skeleton, such as 4,4′,4″-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), and 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), and compounds having a furan skeleton, such as 4,4′,4″-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II) and 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II). Among the above, compounds having an aromatic amine skeleton or a carbazole skeleton are preferred because of their excellent reliability, high hole transport properties, and contribution to reduced driving voltage. In addition, the organic compounds listed as examples of materials having hole transport properties in the hole transport layer 112 can also be used as the hole transport material of the host.
[0177] By mixing an electron transport material and a hole transport material, the transport property of the light-emitting layer 113 can be easily adjusted, and the recombination region can be easily controlled. Also, a TADF material can be used as an electron transport material or a hole transport material.
[0178] The TADF materials that can be used as host materials are the same as those listed above. When a TADF material is used as a host material, the triplet excitation energy generated in the TADF material is converted to singlet excitation energy through reverse intersystem crossing, and the energy is then transferred to the light-emitting material, thereby improving the luminous efficiency of the light-emitting device. In this case, the TADF material functions as an energy donor, and the light-emitting material functions as an energy acceptor.
[0179] This is very effective when the luminescent material is a fluorescent luminescent material. In this case, in order to obtain high luminous efficiency, the S1 level of the TADF material is preferably higher than the S1 level of the fluorescent luminescent material. In addition, the T1 level of the TADF material is preferably higher than the S1 level of the fluorescent luminescent material. Therefore, the T1 level of the TADF material is preferably higher than the T1 level of the fluorescent luminescent material.
[0180] It is also preferable to use a TADF material that emits light that overlaps with the wavelength of the lowest-energy absorption band of the fluorescent material, as this allows for smooth transfer of excitation energy from the TADF material to the fluorescent material, resulting in efficient light emission.
[0181] Furthermore, to efficiently generate singlet excitation energy from triplet excitation energy through reverse intersystem crossing, carrier recombination is preferred in the TADF material. It is also preferable that the triplet excitation energy generated in the TADF material does not transfer to triplet excitation energy in the fluorescent material. To achieve this, the fluorescent material preferably has a protecting group around the luminophore (the skeleton responsible for light emission) of the fluorescent material. The protecting group is preferably a substituent without a π bond, and is preferably a saturated hydrocarbon. Specific examples include alkyl groups with 3 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 10 carbon atoms, and trialkylsilyl groups with 3 to 10 carbon atoms. Multiple protecting groups are even more preferred. Substituents without a π bond have poor carrier transport properties, allowing for increased distance between the TADF material and the luminophore of the fluorescent material without significantly affecting carrier transport and carrier recombination. Here, the term "luminophore" refers to the atomic group (skeleton) responsible for light emission in the fluorescent material. The luminophore preferably has a skeleton having a π bond, preferably contains an aromatic ring, and preferably has a fused aromatic ring or a fused heteroaromatic ring. Examples of such luminophores include a phenanthrene skeleton, a stilbene skeleton, an acridone skeleton, a phenoxazine skeleton, a phenothiazine skeleton, a naphthalene skeleton, an anthracene skeleton, a fluorene skeleton, a chrysene skeleton, a triphenylene skeleton, a tetracene skeleton, a pyrene skeleton, a perylene skeleton, a coumarin skeleton, a quinacridone skeleton, and a naphthobisbenzofuran skeleton. In particular, fluorescent materials having a naphthalene skeleton, an anthracene skeleton, a fluorene skeleton, a chrysene skeleton, a triphenylene skeleton, a tetracene skeleton, a pyrene skeleton, a perylene skeleton, a coumarin skeleton, a quinacridone skeleton, or a naphthobisbenzofuran skeleton are preferred because of their high fluorescence quantum yield.
[0182] When a fluorescent emitting substance is used as the emitting substance, a material having an anthracene skeleton is suitable as the host material. Using a substance having an anthracene skeleton as a host material for a fluorescent emitting substance makes it possible to realize an emitting layer with both excellent luminous efficiency and durability. As a substance having an anthracene skeleton to be used as a host material, a diphenylanthracene skeleton, particularly a 9,10-diphenylanthracene skeleton, is preferred due to its chemical stability. Furthermore, host materials having a carbazole skeleton are preferred because of their enhanced hole injection and transport properties. However, host materials containing a benzocarbazole skeleton, in which a benzene ring is further condensed to the carbazole skeleton, are even more preferred because their HOMO level is approximately 0.1 eV higher than that of host materials having a carbazole skeleton, making it easier for holes to enter. In particular, host materials containing a dibenzocarbazole skeleton are preferred because their HOMO level is approximately 0.1 eV higher than that of host materials having a carbazole skeleton, making it easier for holes to enter, as well as providing excellent hole transport properties and high heat resistance. Therefore, a more preferable host material is a substance having both a 9,10-diphenylanthracene skeleton and a carbazole skeleton (or a benzocarbazole skeleton or a dibenzocarbazole skeleton). Note that, from the viewpoint of the hole injection / transport property, a benzofluorene skeleton or a dibenzofluorene skeleton may be used instead of the carbazole skeleton.Examples of such substances include 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviated as PCzPA), 3-[4-(1-naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviated as PCPN), 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviated as CzPA), 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated as cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl]benzo[b]naphtho[1,2-d]furan (abbreviated as 2mBnfPPA), 9-phenyl-10-[4'-(9-furan [phenyl-9H-fluoren-9-yl)biphenyl-4-yl]anthracene (abbreviation: FLPPA), 9-(1-naphthyl)-10-(2-naphthyl)anthracene (abbreviation: α,β-ADN), 2-(10-phenylanthracen-9-yl)dibenzofuran, 2-(10-phenyl-9-anthryl)benzo[b]naphtho[2,3-d]furan (abbreviation: Bnf(II)PhA), 9-(2-naphthyl)-10-[3-(2-naphthyl)phenyl]anthracene (abbreviation: βN-mβNPAnth), 1-{4-[10-(biphenyl-4-yl)-9-anthryl]phenyl}-2-ethyl-1H-benzimidazole (abbreviation: EtBImPBPhA), and the like. In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA are preferable choices because they exhibit very good properties.
[0183] A phosphorescent material can be used as part of the mixed material. The phosphorescent material can be used as an energy donor that provides excitation energy to a fluorescent material when the fluorescent material is used as a light-emitting material.
[0184] The mixed materials may also form an exciplex. The exciplex is preferably selected from a combination that forms an exciplex that emits light that overlaps with the wavelength of the lowest-energy absorption band of the light-emitting material, because this allows for smooth energy transfer and efficient light emission. Furthermore, this configuration is also preferable because it reduces the driving voltage.
[0185] At least one of the materials forming the exciplex may be a phosphorescent material, which allows efficient conversion of triplet excitation energy into singlet excitation energy through reverse intersystem crossing.
[0186] As a combination of materials that efficiently form an exciplex, it is preferable that the HOMO level of the hole-transporting material is equal to or higher than the HOMO level of the electron-transporting material. It is also preferable that the LUMO level of the hole-transporting material is equal to or higher than the LUMO level of the electron-transporting material. The LUMO and HOMO levels of the materials can be derived from the electrochemical properties (reduction potential and oxidation potential) of the materials measured by cyclic voltammetry (CV).
[0187] The formation of exciplexes can be confirmed by, for example, comparing the emission spectra of a hole-transporting material, an electron-transporting material, and a mixed film of these materials and observing the phenomenon that the emission spectrum of the mixed film is shifted to longer wavelengths than the emission spectra of each material (or has a new peak at longer wavelengths). 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 a mixed film of these materials and observing differences in transient response, such as the transient PL lifetime of the mixed film having a longer-lived component or a larger proportion of delayed components than the transient PL lifetimes of the individual materials. The above-mentioned transient PL can also be interpreted as transient electroluminescence (EL). In other words, the formation of exciplexes can also be confirmed by comparing the transient EL of a hole-transporting material, the transient EL of an electron-transporting material, and a mixed film of these materials and observing differences in transient response.
[0188] The light-emitting layer 113 can be formed by a vapor deposition method (including a vacuum deposition method), an inkjet method, a coating method, gravure printing, etc. In addition to the materials described above, the light-emitting layer 113 may contain inorganic compounds such as quantum dots or polymer compounds (oligomers, dendrimers, polymers, etc.).
[0189] <Hole injection layer> The hole injection layer (111, 111a, 111b) is a layer that injects holes from the first electrode 101, which is an anode, and the charge generation layer (106, 106a, 106b) into the organic compound layer (103, 103a, 103b), and is a layer that contains an organic acceptor material and a material with high hole injection properties.
[0190] For the hole injection layer (111, 111a, 111b), a compound having an electron-withdrawing group (a halogen group or a cyano group) can be used, and examples thereof include 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ), chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN), 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ), and 2-(7-dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyren-2-ylidene)malononitrile. In particular, compounds in which an electron-withdrawing group is bonded to a fused aromatic ring having multiple heteroatoms, such as HAT-CN, are preferred because of their thermal stability. Radialene derivatives having an electron-withdrawing group (especially a halogen group such as a fluoro group or a cyano group) are also preferred because of their extremely high electron-accepting properties. Specific examples include α,α',α''-1,2,3-cyclopropanetriylidenetris[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α',α''-1,2,3-cyclopropanetriylidenetris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], and α,α',α''-1,2,3-cyclopropanetriylidenetris[2,3,4,5,6-pentafluorobenzeneacetonitrile]. As the substance having acceptor properties, in addition to the organic compounds described above, molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide, etc. can be used.In addition, the hole injection layers (111, 111a, 111b) can also be formed using phthalocyanine compounds such as phthalocyanine (abbreviated as HPc), phthalocyanine complex compounds such as copper phthalocyanine (CuPc), aromatic amine compounds such as 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated as DPAB) and N,N'-bis[4-bis(3-methylphenyl)aminophenyl]-N,N'-diphenyl-4,4'-diaminobiphenyl (abbreviated as DNTPD), or polymers such as poly(3,4-ethylenedioxythiophene) / polystyrene sulfonic acid (abbreviated as PEDOT / PSS). Acceptor materials can extract electrons from the adjacent hole transport layer (or hole transport material) when an electric field is applied.
[0191] Among substances having acceptor properties, organic compounds having acceptor properties are easy to use because they can be easily vapor-deposited and formed into a film.
[0192] Furthermore, a composite material in which a material having hole transport properties contains the above-mentioned acceptor substance can also be used for the hole injection layers (111, 111a, 111b). Note that by using a composite material in which a material having hole transport properties contains an acceptor substance, a material for forming an electrode can be selected regardless of the work function. In other words, not only a material with a high work function but also a material with a low work function can be used for the anode (first electrode 101).
[0193] As a material having hole transport properties to be used in the composite material, various organic compounds such as aromatic amine compounds, carbazole derivatives, aromatic hydrocarbons, and polymer compounds (oligomers, dendrimers, polymers, etc.) can be used. Note that as a material having hole transport properties to be used in the composite material, -6 cm 2 A substance having a hole mobility of 1 / Vs or more is preferred. Specific examples of organic compounds that can be used as a material having a hole transport property in a composite material are listed below.
[0194] Examples of aromatic amine compounds that can be used in composite materials include N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), N,N'-bis[4-bis(3-methylphenyl)aminophenyl]-N,N'-diphenyl-4,4'-diaminobiphenyl (abbreviation: DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B). Specific examples of the carbazole derivative include 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenyl Carbazole (abbreviation: PCzPCN1), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), 1,4-bis[4-(N-carbazolyl)phenyl]-2,3,5,6-tetraphenylbenzene, etc. can be used.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), 2-tert- Examples of suitable anthracene include 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, and 2,5,8,11-tetra(tert-butyl)perylene. Pentacene and coronene may also be used. The aromatic hydrocarbon having a vinyl group may also have a vinyl skeleton. Examples of the aromatic hydrocarbon having a vinyl group include 4,4'-bis(2,2-diphenylvinyl)biphenyl (abbreviation: DPVBi) and 9,10-bis[4-(2,2-diphenylvinyl)phenyl]anthracene (abbreviation: DPVPA). Note that the organic compound of one embodiment of the present invention can also be used.
[0195] In addition, polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD) can also be used.
[0196] The hole-transporting material used in the composite material preferably has a carbazole skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton, or an anthracene skeleton. In particular, aromatic amines having a substituent containing 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 may be used. It is preferable that these organic compounds have an N,N-bis(4-biphenyl)amino group, since this allows the fabrication of light-emitting devices with long lifetimes. Specific examples of such organic compounds 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-i 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 Ran-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-03), 4,4'-Diphenyl-4''-(7-phenyl)naphthyl-2-yltriphenylamine (abbreviation: BBAPβNB-03), 4,4'-diphenyl-4''-(6;2'-binaphthyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B), 4,4'-diphenyl-4''-(7;2'-binaphthyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B-03), 4,4'-diphenyl-4''-(4;2'-binaphthyl-1-yl)triphenylamine (abbreviation: BBAβNαNB), 4,4'-diphenyl-4''-(5;2' -binaphthyl-1-yl)triphenylamine (abbreviation: BBAβNαNB-02), 4-(4-biphenylyl)-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: TPBiAβNB), 4-(3-biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: mTPBiAβNBi), 4-(4-biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: TPBiAβNBi), 4-phenyl-4'-(1-naphthyl)triphenylamine (abbreviation: TPBiAβNBi), Phenylamine (abbreviation: αNBA1BP), 4,4'-bis(1-naphthyl)triphenylamine (abbreviation: αNBB1BP), 4,4'-diphenyl-4''-[4'-(carbazol-9-yl)biphenyl-4-yl]triphenylamine (abbreviation: YGTBi1BP), 4'-[4-(3-phenyl-9H-carbazol-9-yl)phenyl]tris(biphenyl-4-yl)amine (abbreviation: YGTBi1BP-02), 4-[4'-(carbazol-9-yl)biphenyl-4-yl]-4'-(2-naphthyl)-4''-phenyltriphenylamine Phenylamine (abbreviation: YGTBiβNB), N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-N-[4-(1-naphthyl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: PCBNBSF), N,N-bis(biphenyl-4-yl)-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: BBASF), N,N-bis(biphenyl-4-yl)-9,9'-spirobi[9H-fluorene]-4-amine (abbreviation: BBASF(4)), N-(biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[9H-fluoren]-4-amine (abbreviation: oFBiSF), N-(biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzofuran-4-amine (abbreviation: FrBiF), N-[4-(1-naphthyl)phenyl]-N-[3-(6-phenyldibenzofuran-4-yl)phenyl]-1-naphthylamine (abbreviation: mPDBfBNBN), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-Phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated as mBPAFLP), 4-phenyl-4'-[4-(9-phenylfluoren-9-yl)phenyl]triphenylamine (abbreviated as BPAFLBi), 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9 N-(4-biphenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBASF), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi[9H-fluoren]-2-amine (abbreviation: PCBASF), N-(biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine Examples of suitable amines include PCBBiF (abbreviation: PCBBiF), N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-4-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-3-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-2-amine, and N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-1-amine.
[0197] Note that the material having hole-transporting properties used in the composite material is more preferably a substance having a relatively low HOMO level of -5.7 eV or more and -5.4 eV or less. When the material having hole-transporting properties used in the composite material has a relatively low HOMO level, injection of holes into the hole-transport layer 112 becomes easy, and a light-emitting device with a long lifetime can be easily obtained. Furthermore, when the material having hole-transporting properties used in the composite material has a relatively low HOMO level, hole induction is appropriately suppressed, and a light-emitting device with a long lifetime can be obtained.
[0198] The refractive index of the layer can be reduced by further mixing an alkali metal or alkaline earth metal fluoride into the composite material (preferably with an atomic ratio of fluorine atoms of 20% or more in the layer). This also makes it possible to form a layer with a low refractive index inside the organic compound layer 103, thereby improving the external quantum efficiency of the light-emitting device.
[0199] By forming the hole injection layers (111, 111a, 111b), the hole injection property is improved, and a light emitting device with a low driving voltage can be obtained.
[0200] <Hole transport layer> The hole transport layers (112, 112a, 112b) are layers containing a hole transport material, and the hole transport materials exemplified as the material for the hole injection layers (111, 111a, 111b) can be used. The hole transport layers (112, 112a, 112b) have the function of transporting holes injected into the hole injection layers (111, 111a, 111b) to the light-emitting layers (113, 113a, 113b), and therefore preferably have a HOMO level that is the same as or close to the HOMO level of the hole injection layers (111, 111a, 111b).
[0201] Also, 1×10 -6 cm 2It is preferable that the material has a hole mobility of 1 / Vs or more. However, other materials may be used as long as they have a higher hole transporting property than electron transporting property. Note that the layer containing the material with a high hole transporting property may be a single layer or may be a stack of two or more layers made of the above material.
[0202] Materials that can be used for the hole transport layer (112, 112a, 112b) include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminobiphenyl (abbreviation: TPD), N,N'-bis(9,9'-spirobi[9H-fluoren]-2-yl)-N,N'-diphenyl-4,4'-diaminobiphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPA), FLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated as mBPAFLP), 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviated as PCBANB), 4,4'-di(1-naphthyl)-4'' Compounds with an aromatic amine skeleton, such as N-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), and N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: PCBASF), 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-diphenyl- (N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviation: CzTP), 9,9'-diphenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCP), 9,9'-bis(biphenyl-4-yl)-3,3'-bi-9H-carbazole (abbreviation: BisBPCz), 9,9'-bis(biphenyl-3-yl)-3,3'-bi-9H-carbazole (abbreviation: BismBPCz), 9-(biphenyl-3-yl)-9'-(biphenyl-4-yl)-9H,9'H-3,Examples of compounds include compounds having a carbazole skeleton such as 3'-bicarbazole (abbreviation: mBPCCBP); compounds having a thiophene skeleton such as 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), and 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV); and compounds having a furan skeleton such as 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II) and 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II). Among the above, compounds having an aromatic amine skeleton or a carbazole skeleton are preferable because they have good reliability, high hole transport properties, and contribute to reducing driving voltage. Note that the substances listed as materials having hole transport properties used in the composite material of the hole injection layer 111 can also be suitably used as materials for forming the hole transport layer 112.
[0203] ≪Electron transport layer≫ The electron-transport layers (114, 114a, and 114b) have a function of transporting electrons injected from the other of the pair of electrodes (the first electrode 101 or the second electrode 102) through the electron-injection layers (115, 115a, and 115b) to the light-emitting layer 113. Note that the organic compound of one embodiment of the present invention described in Embodiment 1 can also be used for the electron-transport layer.
[0204] The electron transporting material is an organic compound having electron transport properties, and the electron mobility at a square root of the electric field strength [V / cm] of 600 is 1×10 -6 cm 2A substance having an electron mobility of 1 / Vs or more is preferred. Note that other substances can be used as long as they have a higher electron transporting property than holes. Note that the organic compound is preferably an organic compound having a π-electron-deficient heteroaromatic ring. The organic compound having a π-electron-deficient heteroaromatic ring is preferably one or more of, for example, an organic compound having a heteroaromatic ring with an azole skeleton, an organic compound having a heteroaromatic ring with a pyridine skeleton, an organic compound having a heteroaromatic ring with a diazine skeleton, and an organic compound having a heteroaromatic ring with a triazine skeleton.
[0205] Specific examples of organic compounds having a π-electron-deficient heteroaromatic ring that can be used in the electron transport layer include 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 1,3-bis[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-8), 1,3-bis[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-9 ... Organic compounds with an azole skeleton, such as 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs), 3,5-bis[3-(9H-carbazol-9-yl)phenyl]- organic compounds containing heteroaromatic rings with a pyridine skeleton, such as 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), ... '-(Dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 2-[4'-(9-phenyl-9H-carbazol-3-yl)-3,1'-biphenyl-1-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mpPCBPDBq), 2-[4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPDBq-II), 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II), 9-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviation: 9mDBtBPNfpr), 9-[3'-(dibenzothiophen-4-yl)biphenyl- 4-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviation: 9pmDBtBPNfpr), 4,6-bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(dibenzothiophen-4-yl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazol-9-yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), 9,9'-[pyrimidine-4,6-diylbis(biphenyl-3,3'-diyl)]bis(9H -carbazole) (abbreviation: 4,6mCzBP2Pm), 8-(biphenyl-4-yl)-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8BP-4mDBtPBfpm), 3,8-bis[3-(dibenzothiophen-4-yl)phenyl]benzofuro[2,3-b]pyrazine (abbreviation: 3,8mDBtP2Bfpr), 8-[3'-(dibenzothiophen-4-yl)(biphenyl-3-yl)]naphtho[1',2':4,5]furo[3,2-d]pyrimidine (abbreviation: 8mDBtBPNf pm), 8-[(2,2'-binaphthalen)-6-yl]-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviated as 8(βN2)-4mDBtPBfpm), 2,2'-(pyridine-2,6-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviated as 2,6(P-Bqn)2Py), 2,2'-(pyridine-2,6-diyl)bis{4-[4-(2-naphthyl)phenyl]-6-phenylpyrimidine} (abbreviated as 2,6(NP-PPm)2Py), 6-(biphenyl-3-yl)-4-[3,5-Bis(9H-carbazol-9-yl)phenyl]-2-phenylpyrimidine (abbreviated as 6mBP-4Cz2PPm), 2,4-bis[4-(1-naphthyl)phenyl]-6-[4-(3-pyridyl)phenyl]pyrimidine (abbreviated as 2,4NP-6PyPPm), 4-[3,5-bis(9H-carbazol-9-yl)phenyl]-2-phenyl-6-(biphenyl-4-yl)pyrimidine (abbreviated as 6BP-4Cz2PPm), 7-[4-(9-phenyl-9H-carbazol-2-yl)quinazolin-2-yl]-7H-dibenzo[c,g]carbazol-2-yl Organic compounds with a diazine skeleton, such as benzo[b]naphtho[1,2-d]furan-8-ylphenyl]phenyl, 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (mFBPTzn), 2-(biphenyl-4-yl)-4-phenyl-6-(9,9'-spirobi[9H-fluoren]-2-yl)-1,3,5-triazine (BP-SFTzn), and 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-8-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (BP-SFTzn). ,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), 9-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-3,3'-bi-9H-carbazole (abbreviation: PCCzPTzn), 9-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-2,3'-bi-9H-carbazole mPCCzPTzn-02), 5-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-7,7-dimethyl-5H,7H-indeno[2,1-b]carbazole (mINc(II)PTzn), 2-{3-[3-(dibenzothiophen-4-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (mDBtBPTzn), 2,4,6-tris[3'-(pyridin-3-yl)biphenyl-3-yl]-1,3,5-triazine (TmPPPyTz), 2-[3-(2,6-dimethyl-3-pyridinyl)-5-(9-phenanthryl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mPn-mDMePyPTzn), 11-[4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazin-2-yl]-11,12-dihydro-12-phenylindolo[2,3-a]carbazole (abbreviation: BP-Icz(II)Tzn), 2-[3'-(triphenylen-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3 Examples of organic compounds having a triazine skeleton include 2-(biphenyl-3-yl)-4-phenyl-6-{8-[(1,1':4',1''-terphenyl)-4-yl]-1-dibenzofuranyl}-1,3,5-triazine (abbreviation: mBP-TPDBfTzn), 3-[9-(4,6-diphenyl-1,3,5-triazin-2-yl)-2-dibenzofuranyl]-9-phenyl-9H-carbazole (abbreviation: PCDBfTzn), and 2-(biphenyl-3-yl)-4-phenyl-6-{8-[(1,1':4',1''-terphenyl)-4-yl]-1-dibenzofuranyl}-1,3,5-triazine (abbreviation: mBP-TPDBfTzn). Among the above, organic compounds having a heteroaromatic ring with a diazine skeleton, organic compounds having a heteroaromatic ring with a pyridine skeleton, and organic compounds having a heteroaromatic ring with a triazine skeleton are preferred due to their high reliability. In particular, organic compounds containing heteroaromatic rings with a diazine (pyrimidine and pyrazine) skeleton and organic compounds containing heteroaromatic rings with a triazine skeleton have high electron transport properties and contribute to reducing driving voltages.
[0206] The electron transport layer (114, 114a, 114b) may be a single layer or may be a stack of two or more layers made of the above-mentioned materials.
[0207] Furthermore, a layer for controlling the movement of electron carriers may be provided between the electron transport layer (114, 114a, 114b) and the light-emitting layer (113, 113a, 113b). This layer is made by adding a small amount of a substance with high electron trapping properties to a material with high electron transport properties as described above, and by suppressing the movement of electron carriers, it becomes possible to adjust the carrier balance. Such a configuration is highly effective in suppressing problems (e.g., a reduction in device life) caused by electrons passing through the light-emitting layer.
[0208] ≪Electron injection layer≫ The electron-injection layers (115, 115a, and 115b) have a function of promoting electron injection by reducing the barrier to electron injection from the second electrode 102. Note that the organic compound represented by the general formula (G1) in Embodiment 1 can also be used for the electron-injection layer.
[0209] Furthermore, for example, Group 1 metals, Group 2 metals, or oxides, halides, carbonates, etc. thereof can be used. Furthermore, a composite material of the above-mentioned electron transporting material and a material that exhibits electron donating properties can also be used. Examples of materials that exhibit electron donating properties include Group 1 metals, Group 2 metals, or oxides thereof. Specifically, lithium fluoride (LiF), sodium fluoride (NaF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium oxide (LiO x Alkali metals, alkaline earth metals, or compounds thereof such as fluoride (ErF3) can be used. Rare earth metal compounds such as erbium fluoride (ErF3) can also be used. Electrides can also be used for the electron injection layer 115. Examples of such electrides include a substance in which a high concentration of electrons is added to a mixed oxide of calcium and aluminum. Substances that can be used for the electron transport layers (114, 114a, 114b) can also be used for the electron injection layers (115, 115a, 115b).
[0210] The electron injection layer (115, 115a, 115b) may also be made of a composite material containing an organic compound and an electron donor (donor). Such composite materials have excellent electron injection and transport properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material that is excellent at transporting the generated electrons. Specifically, the above-mentioned substances constituting the electron transport layer 114 (metal complexes, heteroaromatic compounds, etc.) can be used. The electron donor may be any substance that exhibits electron donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, or rare earth metals are preferred, such as lithium, sodium, cesium, magnesium, calcium, erbium, and ytterbium. Alkali metal oxides or alkaline earth metal oxides are preferred, such as lithium oxide, calcium oxide, and barium oxide. Lewis bases such as magnesium oxide can also be used. Organic compounds such as tetrathiafulvalene (TTF) can also be used.
[0211] The light-emitting layer, hole injection layer, hole transport layer, electron transport layer, and electron injection layer can be formed by vapor deposition (including vacuum deposition), inkjet printing, coating, gravure printing, etc. In addition to the materials described above, the light-emitting layer, hole injection layer, hole transport layer, electron transport layer, and electron injection layer may be made of inorganic compounds such as quantum dots or polymeric compounds (oligomers, dendrimers, polymers, etc.).
[0212] Quantum dots may be colloidal quantum dots, alloy quantum dots, core-shell quantum dots, core quantum dots, etc. Quantum dots containing elements from groups 2 and 16, 13 and 15, 13 and 17, 11 and 17, or 14 and 15 may also be used. Quantum dots containing elements such as cadmium (Cd), selenium (Se), zinc (Zn), sulfur (S), phosphorus (P), indium (In), tellurium (Te), lead (Pb), gallium (Ga), arsenic (As), and aluminum (Al) may also be used.
[0213] <Pair of electrodes> The first electrode 101 and the second electrode 102 function as an anode or a cathode of the light-emitting device. The first electrode 101 and the second electrode 102 can be formed using a metal, an alloy, a conductive compound, or a mixture or stack of these materials.
[0214] It is preferable that one of the first electrode 101 and the second electrode 102 is formed of a conductive material that has a light-reflecting function. Examples of the conductive material include aluminum (Al) and alloys containing Al. Examples of alloys containing Al include alloys containing Al and L (L represents one or more of titanium (Ti), neodymium (Nd), nickel (Ni), and lanthanum (La)), such as alloys containing Al and Ti, or Al, Ni, and La. Aluminum has low resistance and high light reflectivity. Furthermore, aluminum is abundant in the earth's crust and inexpensive, so the use of aluminum can reduce the production costs of light-emitting devices. Alternatively, silver (Ag) or an alloy containing Ag and N (N represents one or more of yttrium (Y), Nd, magnesium (Mg), ytterbium (Yb), Al, Ti, gallium (Ga), zinc (Zn), indium (In), tungsten (W), manganese (Mn), tin (Sn), iron (Fe), Ni, copper (Cu), palladium (Pd), iridium (Ir), or gold (Au)) may be used. Examples of alloys containing silver include alloys containing silver, palladium, and copper, alloys containing silver and copper, alloys containing silver and magnesium, alloys containing silver and nickel, alloys containing silver and gold, and alloys containing silver and ytterbium. Other transition metals that can be used include tungsten, chromium (Cr), molybdenum (Mo), copper, and titanium.
[0215] Furthermore, light emitted from the light-emitting layer is extracted through one or both of the first electrode 101 and the second electrode 102. Therefore, at least one of the first electrode 101 and the second electrode 102 is preferably formed from a conductive material that has a light-transmitting function. The conductive material has a visible light transmittance of 40% or more and 100% or less, preferably 60% or more and 100% or less, and a resistivity of 1×10 -2 Examples include conductive materials with a resistance of Ω·cm or less.
[0216] The first electrode 101 and the second electrode 102 may be formed of a conductive material that has both a light transmitting and a light reflecting function. The conductive material has a visible light reflectance of 20% to 80%, preferably 40% to 70%, and a resistivity of 1×10 -2 Examples of suitable materials include conductive materials with a resistivity of Ω·cm or less. For example, the film can be formed using one or more conductive metals, alloys, conductive compounds, etc. Specifically, metal oxides such as indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide (abbreviated as ITSO), indium zinc oxide, titanium-containing indium tin oxide, indium titanium oxide, and indium oxide containing tungsten oxide and zinc oxide can be used. Alternatively, a thin metal film that is light-transmitting (preferably, a thickness of 1 nm to 30 nm) can be used. Examples of suitable metals include Ag. Examples of suitable alloys include alloys of Ag and Al, Ag and Mg, Ag and Au, and Ag and Yb.
[0217] In this specification and the like, the material having the function of transmitting light may be any material that has the function of transmitting visible light and is conductive, and includes, for example, oxide conductors such as ITO as described above, as well as oxide semiconductors or organic conductors containing organic substances. Examples of organic conductors containing organic substances include composite materials obtained by mixing an organic compound with an electron donor (donor), and composite materials obtained by mixing an organic compound with an electron acceptor. In addition, inorganic carbon-based materials such as graphene may also be used. The resistivity of the material is preferably 1×10 5 Ω·cm or less, more preferably 1×10 4 Ω·cm or less.
[0218] Alternatively, one or both of the first electrode 101 and the second electrode 102 may be formed by stacking a plurality of the above materials.
[0219] Furthermore, in order to improve light extraction efficiency, a material having a higher refractive index than an electrode having a light-transmitting function may be formed in contact with the electrode. Such a material may be any material that transmits visible light, and may or may not be conductive. Examples of such a material include oxide semiconductors and organic materials, as well as the oxide conductors described above. Examples of organic materials include the materials exemplified for the light-emitting layer, hole injection layer, hole transport layer, electron transport layer, and electron injection layer. Inorganic carbon-based materials or thin metal films that transmit light may also be used, and multiple layers of several nanometers to several tens of nanometers thick may be stacked.
[0220] When the first electrode 101 or the second electrode 102 functions as a cathode, it is preferable that the electrode be made of a material with a small work function (3.8 eV or less). For example, elements belonging to Group 1 or 2 of the periodic table (alkali metals such as lithium, sodium, and cesium, alkaline earth metals such as calcium and strontium, magnesium, etc.), alloys containing these elements (e.g., Ag and Mg, Al and Li), rare earth metals such as europium (Eu) and Yb, alloys containing these rare earth metals, alloys containing aluminum and silver, etc. can be used.
[0221] When the first electrode 101 or the second electrode 102 is used as an anode, it is preferable to use a material with a large work function (4.0 eV or more).
[0222] The first electrode 101 and the second electrode 102 may be a laminate of a conductive material having a light-reflecting function and a conductive material having a light-transmitting function. In this case, the first electrode 101 and the second electrode 102 are preferable because they can adjust the optical path so that light of a desired wavelength from each light-emitting layer can be resonated and the light of that wavelength can be intensified.
[0223] The first electrode 101 and the second electrode 102 can be formed by any suitable method, such as sputtering, vapor deposition, printing, coating, MBE (Molecular Beam Epitaxy), CVD, pulsed laser deposition, or ALD (Atomic Layer Deposition).
[0224] <Charge generation layer (intermediate layer)> The charge generation layer 106 has a function of injecting electrons into the organic compound layer 103a and injecting holes into the organic compound layer 103b when a voltage is applied between the first electrode (anode) 101 and the second electrode (cathode) 102. The charge generation layer 106 may be a layer in which an electron acceptor is added to a hole transporting material (also referred to as a p-type layer) or an electron donor is added to an electron transporting material (also referred to as an electron injection buffer layer). Alternatively, both of these layers may be stacked. Furthermore, an electron relay layer may be provided between the p-type layer and the electron injection buffer layer. Forming the charge generation layer 106 using the above-described materials can suppress an increase in driving voltage when organic compound layers including a light-emitting layer are stacked.
[0225] When the charge generation layer 106 has a structure in which an electron acceptor is added to a hole-transporting material that is an organic compound (a p-type layer), the hole-transporting material described in this embodiment can be used as the hole-transporting material. Examples of the electron acceptor include 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ) and chloranil. Examples of the electron acceptor include oxides of metals that belong to Groups 4 to 8 of the periodic table. Specific examples include vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide. The acceptor materials described above may also be used. Materials for the p-type layer may be mixed together to form a mixed film, or single films containing each material may be stacked.
[0226] When the charge generation layer 106 has a structure in which an electron donor is added to an electron transporting material (electron injection buffer layer), the electron transporting material is preferably the organic compound described in Embodiment 1. Alternatively, the electron transporting material described in this embodiment may be used.
[0227] As the electron donor, alkali metals, alkaline earth metals, rare earth metals, or metals belonging to Groups 2 and 13 of the periodic table, as well as oxides and carbonates thereof, can be used. Specifically, lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), ytterbium (Yb), indium (In), lithium oxide (LiO), cesium carbonate, etc. can be preferably used. Alternatively, an organic compound such as tetrathianaphthacene can be used as the electron donor.
[0228] When an electron relay layer is provided between the p-type layer and the electron injection buffer layer in the charge generation layer 106, the electron relay layer contains at least a substance having electron transport properties and has the function of preventing interaction between the electron injection buffer layer and the p-type layer and smoothly transferring electrons. The LUMO level of the substance having electron transport properties contained in the electron relay layer is preferably between the LUMO level of the acceptor substance in the p-type layer and the LUMO level of the substance having electron transport properties contained in the electron transport layer in contact with the charge generation layer 106. The specific energy level of the LUMO level of the substance having electron transport properties used in the electron relay layer is −5.0 eV or higher, preferably −5.0 eV or higher and −3.0 eV or lower. Note that the substance having electron transport properties used in the electron relay layer is preferably a phthalocyanine-based material or a metal complex having a metal-oxygen bond and an aromatic ligand.
[0229] Although Figure 2(D) shows a structure in which two organic compound layers 103 are stacked, a stacked structure of organic compound layers including three or more light-emitting layers may be used by providing a charge generation layer between different light-emitting layers.
[0230] <Cap layer> Although not shown in FIGS. 2A to 2E, a capping layer may be provided on the second electrode 102 of the light-emitting device. For example, a material with a high refractive index can be used for the capping layer. By providing the capping layer on the second electrode 102, the extraction efficiency of light emitted from the second electrode 102 can be improved.
[0231] Specific examples of materials that can be used for the cap layer include 5,5'-diphenyl-2,2'-di-5H-[1]benzothieno[3,2-c]carbazole (abbreviation: BisBTc) and 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II).
[0232] <Substrate> Furthermore, the light-emitting device according to one embodiment of the present invention can be fabricated over a substrate made of glass, plastic, etc. The order of fabrication on the substrate may be from the first electrode 101 side or from the second electrode 102 side.
[0233] Note that, as a substrate on which a light-emitting device according to one embodiment of the present invention can be formed, for example, glass, quartz, or plastic can be used. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), and examples thereof include a plastic substrate made of polycarbonate or polyarylate. Films, inorganic vapor-deposited films, and the like can also be used. Note that other materials may be used as long as they function as a support in the manufacturing process of the light-emitting device and the optical element. Alternatively, any material may be used as long as it has a function of protecting the light-emitting device and the optical element.
[0234] For example, in this specification, a light-emitting device can be formed using various substrates. The type of substrate is not particularly limited. Examples of such substrates include semiconductor substrates (e.g., single-crystal substrates such as silicon substrates), SOI substrates, glass substrates, quartz substrates, plastic substrates, metal substrates, stainless steel substrates, substrates with stainless steel foil, tungsten substrates, substrates with tungsten foil, flexible substrates, laminated films, cellulose nanofibers (CNF) containing fibrous materials, paper, and base films. Examples of glass substrates include barium borosilicate glass, aluminoborosilicate glass, and soda-lime glass. Examples of flexible substrates, laminated films, and base films include the following: plastics such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), and polytetrafluoroethylene (PTFE). Another example is acrylic resin. Another example is polypropylene, polyester, polyvinyl fluoride, or polyvinyl chloride. Other examples include resins such as polyamide, polyimide, aramid, and epoxy, inorganic vapor-deposited films, and papers.
[0235] Alternatively, a flexible substrate may be used as the substrate, and the light-emitting device may be formed directly on the flexible substrate. Alternatively, a release layer may be provided between the substrate and the light-emitting device. The release layer can be used to separate the light-emitting device from the substrate after it has been partially or entirely completed and transfer it to another substrate. In this case, the light-emitting device can be transferred to a substrate with poor heat resistance or a flexible substrate. The release layer may be, for example, a laminated structure of inorganic films such as a tungsten film and a silicon oxide film, or a structure in which a resin film such as polyimide is formed on a substrate.
[0236] That is, a light-emitting device may be formed using a certain substrate, and then the light-emitting device may be transferred to another substrate, and the light-emitting device may be disposed on the other substrate. In addition to the substrates mentioned above, examples of the substrate onto which the light-emitting device may be transferred include a cellophane substrate, a stone substrate, a wood substrate, a cloth substrate (including natural fibers (silk, cotton, linen), synthetic fibers (nylon, polyurethane, polyester), or recycled fibers (acetate, cupra, rayon, recycled polyester)), a leather substrate, or a rubber substrate. By using these substrates, a light-emitting device that is durable, highly heat-resistant, lightweight, or thin can be obtained.
[0237] Alternatively, a field effect transistor (FET) may be formed on the substrate, and a light-emitting device may be fabricated on an electrode electrically connected to the FET, thereby producing an active matrix display device in which the FET controls the driving of the light-emitting device.
[0238] Note that one embodiment of the present invention has been described in this embodiment. Alternatively, another embodiment of the present invention will be described. However, one embodiment of the present invention is not limited thereto. That is, various embodiments of the present invention are described in this embodiment and the other embodiments, and therefore one embodiment of the present invention is not limited to a specific embodiment. For example, although an example in which the present invention is applied to a light-emitting device has been described as one embodiment of the present invention, one embodiment of the present invention is not limited thereto. For example, depending on the circumstances or the situation, one embodiment of the present invention does not need to be applied to a light-emitting device. Alternatively, for example, one embodiment of the present invention has a first organic compound, a second organic compound, and a guest material capable of converting triplet excitation energy into light emission, and the LUMO level of the first organic compound is lower than the LUMO level of the second organic compound, and the HOMO level of the first organic compound is lower than the HOMO level of the second organic compound. However, one embodiment of the present invention is not limited thereto. Depending on the circumstances or the situation, in one embodiment of the present invention, for example, the LUMO level of the first organic compound does not need to be lower than the LUMO level of the second organic compound. Alternatively, the HOMO level of the first organic compound does not have to be lower than the HOMO level of the second organic compound. Alternatively, for example, in one embodiment of the present invention, the first organic compound and the second organic compound form an exciplex. However, this embodiment is not limited to this example. Depending on the circumstances, or depending on the situation, in one embodiment of the present invention, the first organic compound and the second organic compound do not have to form an exciplex. Alternatively, for example, in one embodiment of the present invention, the LUMO level of the guest material is higher than the LUMO level of the first organic compound and lower than the HOMO level of the second organic compound. However, this embodiment is not limited to this example. Depending on the circumstances, or depending on the situation, in one embodiment of the present invention, the LUMO level of the guest material does not have to be higher than the LUMO level of the first organic compound. Alternatively, the HOMO level of the guest material does not have to be lower than the HOMO level of the second organic compound.
[0239] The structure described in this embodiment mode can be used in appropriate combination with structures described in other embodiments.
[0240] (Embodiment 3) 3A and 3B, a plurality of light-emitting devices 130 are formed over an insulating layer 175 to form a display device. In this embodiment, a display device according to one embodiment of the present invention will be described in detail.
[0241] The display device 100 has a pixel section 177 in which a plurality of pixels 178 are arranged in a matrix. The pixel 178 has a sub-pixel 110R, a sub-pixel 110G, and a sub-pixel 110B.
[0242] In this specification and the like, when describing matters common to, for example, the subpixels 110R, 110G, and 110B, they may be referred to as the subpixels 110. When describing matters common to other components distinguished by alphabets, they may also be described using symbols without the alphabets.
[0243] The sub-pixel 110R emits red light, the sub-pixel 110G emits green light, and the sub-pixel 110B emits blue light. This allows an image to be displayed in the pixel unit 177. In this embodiment, sub-pixels of three colors, red (R), green (G), and blue (B), are described as an example, but combinations of sub-pixels of other colors may also be used. The number of sub-pixels is not limited to three, and may be four or more. Examples of four sub-pixels include sub-pixels of four colors: R, G, B, and white (W); sub-pixels of four colors: R, G, B, and yellow (Y); and sub-pixels of R, G, B, and infrared (IR).
[0244] In this specification, the row direction may be referred to as the X direction, and the column direction may be referred to as the Y direction. The X direction and the Y direction intersect, for example, perpendicularly.
[0245] 3A shows an example in which sub-pixels of different colors are arranged side by side in the X direction, and sub-pixels of the same color are arranged side by side in the Y direction. Note that sub-pixels of different colors may also be arranged side by side in the Y direction, and sub-pixels of the same color may also be arranged side by side in the X direction.
[0246] A connection portion 140 may be provided outside the pixel portion 177, and a region 141 may be provided. The region 141 is provided between the pixel portion 177 and the connection portion 140. The region 141 is provided with an organic compound layer 103. Furthermore, the connection portion 140 is provided with a conductive layer 151C.
[0247] 3A shows an example in which the region 141 and the connection portion 140 are located on the right side of the pixel portion 177, but the positions of the region 141 and the connection portion 140 are not particularly limited. The region 141 and the connection portion 140 may be singular or plural.
[0248] Fig. 3(B) is an example of a cross-sectional view taken along dashed line A1-A2 in Fig. 3(A). As shown in Fig. 3(B), the display device 100 includes an insulating layer 171, a conductive layer 172 on the insulating layer 171, an insulating layer 173 on the insulating layer 171 and on the conductive layer 172, an insulating layer 174 on the insulating layer 173, and an insulating layer 175 on the insulating layer 174. The insulating layer 171 is provided on a substrate (not shown). The insulating layer 175, the insulating layer 174, and the insulating layer 173 have openings that reach the conductive layer 172, and a plug 176 is provided to fill the opening.
[0249] In the pixel section 177, the light-emitting device 130 is provided on the insulating layer 175 and the plug 176. A protective layer 131 is provided to cover the light-emitting device 130. The substrate 120 is bonded to the protective layer 131 by a resin layer 122. Preferably, an inorganic insulating layer 125 and an insulating layer 127 on the inorganic insulating layer 125 are provided between adjacent light-emitting devices 130.
[0250] 3B shows multiple cross sections of the inorganic insulating layer 125 and the insulating layer 127, it is preferable that the inorganic insulating layer 125 and the insulating layer 127 are connected to one another when the display device 100 is viewed from above. That is, it is preferable that the inorganic insulating layer 125 and the insulating layer 127 are insulating layers having openings above the first electrodes.
[0251] 3(B) shows light emitting device 130R, light emitting device 130G, and light emitting device 130B. Light emitting device 130R, light emitting device 130G, and light emitting device 130B emit light of different colors. For example, light emitting device 130R can emit red light, light emitting device 130G can emit green light, and light emitting device 130B can emit blue light. Furthermore, light emitting device 130R, light emitting device 130G, or light emitting device 130B may emit other visible light or infrared light.
[0252] The display device of one embodiment of the present invention can be, for example, a top-emission type that emits light in the direction opposite to the substrate on which the light-emitting device is formed. Note that the display device of one embodiment of the present invention may also be a bottom-emission type.
[0253] Examples of the light-emitting material contained in the light-emitting device 130 include organic compounds or organometallic complexes such as fluorescent materials, phosphorescent materials, and thermally activated delayed fluorescence (TADF) materials. Furthermore, the light-emitting material may also be an inorganic compound such as quantum dots.
[0254] The light-emitting device 130R has a configuration as shown in FIG. 1A. It includes a first electrode (pixel electrode) composed of a conductive layer 151R and a conductive layer 152R, an organic compound layer 103R on the first electrode, a common layer 104 on the organic compound layer 103R, and a second electrode (common electrode) 102 on the common layer 104. The common layer 104 may or may not be provided, but is preferably provided because it can reduce damage to the organic compound layer 103R during processing. When the common layer 104 is provided, it is preferably an electron injection layer. When the common layer 104 is provided, the stacked structure of the organic compound layer 103R and the common layer 104 corresponds to the organic compound layer 103 in the second embodiment.
[0255] The light-emitting device 130G has a configuration as shown in FIG. 1A. It includes a first electrode (pixel electrode) composed of a conductive layer 151G and a conductive layer 152G, an organic compound layer 103G on the first electrode, a common layer 104 on the organic compound layer 103G, and a second electrode (common electrode) 102 on the common layer 104. The common layer 104 may or may not be provided, but is preferably provided because it can reduce damage to the organic compound layer 103G during processing. When the common layer 104 is provided, it is preferably an electron injection layer. When the common layer 104 is provided, the stacked structure of the organic compound layer 103G and the common layer 104 corresponds to the organic compound layer 103 in Embodiment 2.
[0256] The light-emitting device 130B has a configuration as shown in FIG. 1A. It includes a first electrode (pixel electrode) composed of a conductive layer 151B and a conductive layer 152B, an organic compound layer 103B on the first electrode, a common layer 104 on the organic compound layer 103B, and a second electrode (common electrode) 102 on the common layer 104. The common layer 104 may or may not be provided, but is preferably provided because it can reduce damage to the organic compound layer 103B during processing. When the common layer 104 is provided, it is preferably an electron injection layer. When the common layer 104 is provided, the stacked structure of the organic compound layer 103B and the common layer 104 corresponds to the organic compound layer 103 in the second embodiment.
[0257] One of the pixel electrode and the common electrode of the light-emitting device functions as an anode and the other functions as a cathode. In the following description, unless otherwise specified, the pixel electrode functions as an anode and the common electrode functions as a cathode.
[0258] The organic compound layer 103R, the organic compound layer 103G, and the organic compound layer 103B are independent island-shaped layers for each light-emitting device or each emitted color. By providing the organic compound layer 103 in an island shape for each light-emitting device 130, leakage current between adjacent light-emitting devices 130 can be suppressed even in a high-resolution display device. This makes it possible to prevent crosstalk and realize a display device with extremely high contrast. In particular, a display device with high current efficiency at low brightness can be realized.
[0259] The island-shaped organic compound layer 103 is formed by depositing an EL film and processing the EL film using a lithography method.
[0260] In the display device of one embodiment of the present invention, the first electrode (pixel electrode) of the light-emitting device preferably has a stacked structure. For example, in the example shown in FIG. 3B, the first electrode of the light-emitting device 130 has a stacked structure of a conductive layer 151 and a conductive layer 152. For example, when the display device 100 is a top-emission type and the pixel electrode of the light-emitting device 130 functions as an anode, the conductive layer 151 preferably has high reflectivity for visible light, and the conductive layer 152 preferably has transparency to visible light and a high work function. When the display device 100 is a top-emission type, the higher the reflectivity of the pixel electrode for visible light, the higher the extraction efficiency of light emitted from the organic compound layer 103. When the pixel electrode functions as an anode, the higher the work function of the pixel electrode, the easier it is to inject holes into the organic compound layer 103. As described above, by forming the pixel electrode of the light-emitting device 130 into a laminated structure of the conductive layer 151 having a high reflectivity for visible light and the conductive layer 152 having a high work function, the light-emitting device 130 can be made into a light-emitting device with high light extraction efficiency and low driving voltage.
[0261] When the conductive layer 151 is a layer having high reflectivity to visible light, the reflectivity of the conductive layer 151 to visible light is, for example, preferably 40% to 100%, more preferably 70% to 100%. When the conductive layer 152 is an electrode having transparency to visible light, the transmittance to visible light is preferably, for example, 40% or more.
[0262] Here, when the pixel electrode has a laminated structure made up of multiple layers, the pixel electrode may be altered due to, for example, a reaction between the multiple layers. For example, when a film formed after forming the pixel electrode is removed by a wet etching method, galvanic corrosion may occur when a chemical solution comes into contact with the pixel electrode.
[0263] Therefore, in the display device 100 of this embodiment, an insulating layer 156 is formed on the side surfaces of the conductive layer 151 and the conductive layer 152. This prevents a chemical solution from coming into contact with the conductive layer 151, even when a film formed after forming a pixel electrode having the conductive layer 151 and the conductive layer 152 is removed by wet etching, for example. This prevents, for example, galvanic corrosion from occurring in the pixel electrode. Therefore, the display device 100 can be manufactured by a method with a high yield, and can be a low-cost display device. Furthermore, since defects in the display device 100 can be prevented, the display device 100 can be a highly reliable display device.
[0264] For example, a metal material can be used for the conductive layer 151. Specifically, metals such as aluminum (Al), titanium (Ti), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), gallium (Ga), zinc (Zn), indium (In), tin (Sn), molybdenum (Mo), tantalum (Ta), tungsten (W), palladium (Pd), gold (Au), platinum (Pt), silver (Ag), yttrium (Y), neodymium (Nd), etc., and alloys containing appropriate combinations of these metals can also be used.
[0265] The conductive layer 152 can be formed using an oxide containing one or more selected from indium, tin, zinc, gallium, titanium, aluminum, and silicon. For example, it is preferable to use a conductive oxide containing one or more of indium oxide, indium tin oxide, indium zinc oxide, zinc oxide, zinc oxide containing gallium, titanium oxide, indium zinc oxide containing gallium, indium zinc oxide containing aluminum, indium tin oxide containing silicon, and indium zinc oxide containing silicon. In particular, indium tin oxide containing silicon has a large work function, for example, a work function of 4.0 eV or more, and therefore can be suitably used for the conductive layer 152.
[0266] The conductive layer 151 may have a stacked structure of multiple layers containing different materials, and the conductive layer 152 may have a stacked structure of multiple layers containing different materials. In this case, the conductive layer 151 may include a layer containing a material that can be used for the conductive layer 152, such as a conductive oxide, or the conductive layer 152 may include a layer containing a material that can be used for the conductive layer 151, such as a metal material. For example, when the conductive layer 151 has a stacked structure of two or more layers, a layer in contact with the conductive layer 152 can be a layer containing a material that can be used for the conductive layer 152.
[0267] The insulating layer 156 may have a tapered end portion. Specifically, when the insulating layer 156 has a tapered end portion with a taper angle of less than 90°, coverage of structures provided along the side surfaces of the insulating layer 156 can be improved.
[0268] 3A will be described with reference to FIGS. 4 to 9. The light-emitting device of the display device 100 has an organic layer formed by a manufacturing process including a treatment using water. By using the organic compound of one embodiment of the present invention for the organic layer of the light-emitting device of the display device of one embodiment of the present invention, problems such as dissolution of the layer containing the organic compound and penetration of a chemical solution into the layer containing the organic compound can be prevented even when the light-emitting device is manufactured by a manufacturing method including a treatment using water, and a light-emitting device with excellent characteristics can be provided.
[0269] [Example of manufacturing method] Thin films (insulating films, semiconductor films, conductive films, etc.) that make up display devices can be formed using methods such as sputtering, chemical vapor deposition (CVD), vacuum evaporation, pulsed laser deposition (PLD), or ALD. CVD methods include plasma enhanced chemical vapor deposition (PECVD) and thermal CVD. One type of thermal CVD method is metal organic chemical vapor deposition (MOCVD).
[0270] Furthermore, thin films (insulating films, semiconductor films, conductive films, etc.) that constitute the display device can be formed by wet film formation methods such as spin coating, dipping, spray coating, inkjet, dispensing, screen printing, offset printing, doctor knife method, slit coating, roll coating, curtain coating, or knife coating.
[0271] In particular, vacuum processes such as vapor deposition and solution processes such as spin coating and inkjet printing can be used to fabricate light-emitting devices. Vapor deposition methods include physical vapor deposition (PVD) methods such as sputtering, ion plating, ion beam deposition, molecular beam deposition, and vacuum deposition, and chemical vapor deposition (CVD). In particular, functional layers included in the organic compound layer (e.g., hole injection layer, hole transport layer, hole blocking layer, light-emitting layer, electron blocking layer, electron transport layer, and electron injection layer) can be formed by vapor deposition (e.g., vacuum deposition), coating methods (e.g., dip coating, die coating, bar coating, spin coating, and spray coating), printing methods (e.g., inkjet printing, screen printing, offset printing, flexography, gravure printing, and microcontact printing).
[0272] Furthermore, when processing the thin film that constitutes the display device, it can be processed using, for example, a lithography method. Alternatively, the thin film may be processed using a nanoimprint method, a sandblasting method, a lift-off method, etc. Furthermore, the island-shaped thin film may be directly formed by a film formation method using a shielding mask such as a metal mask.
[0273] As a lithography method, for example, photolithography can be used. There are two typical photolithography methods: one is a method in which a resist mask is formed on a thin film to be processed, the thin film is processed by, for example, etching, and then the resist mask is removed; the other is a method in which a photosensitive thin film is formed, and then the thin film is exposed to light and developed to be processed into a desired shape.
[0274] In photolithography, the light used for exposure can be, for example, i-line (wavelength 365 nm), g-line (wavelength 436 nm), h-line (wavelength 405 nm), or a mixture of these. Other light sources that can be used include ultraviolet light, KrF laser light, and ArF laser light. Exposure can also be performed by immersion exposure technology. Extreme ultraviolet (EUV) light or X-rays can also be used as the light used for exposure. An electron beam can also be used instead of the light used for exposure. Extreme ultraviolet light, X-rays, or an electron beam are preferred because they enable extremely fine processing. When exposure is performed by scanning a beam such as an electron beam, a photomask is not required.
[0275] The thin film can be etched by dry etching, wet etching, sandblasting, or the like.
[0276] 4A, an insulating layer 171 is formed on a substrate (not shown). Subsequently, conductive layers 172 and 179 are formed on the insulating layer 171, and an insulating layer 173 is formed on the insulating layer 171 so as to cover the conductive layers 172 and 179. Subsequently, an insulating layer 174 is formed on the insulating layer 173, and an insulating layer 175 is formed on the insulating layer 174.
[0277] The substrate may be a substrate having heat resistance sufficient to withstand at least subsequent heat treatment. When an insulating substrate is used, a glass substrate, a quartz substrate, a sapphire substrate, a ceramic substrate, an organic resin substrate, or the like may be used. Also, a semiconductor substrate such as a single-crystal semiconductor substrate made of silicon or silicon carbide, a polycrystalline semiconductor substrate, a compound semiconductor substrate such as silicon germanium, or an SOI substrate may be used.
[0278] 4A, openings are formed in the insulating layers 175, 174, and 173, reaching the conductive layer 172. Then, plugs 176 are formed to fill the openings.
[0279] 4A, a conductive film 151f, which will later become the conductive layers 151R, 151G, 151B, and 151C, is formed on the plug 176 and the insulating layer 175. The conductive film 151f can be formed by, for example, sputtering or vacuum evaporation. The conductive film 151f can be made of, for example, a metal material.
[0280] 4A, a conductive film 152f, which will later become the conductive layers 152R, 152G, 152B, and 152C, is formed over the conductive film 151f. The conductive film 152f can be formed by, for example, a sputtering method or a vacuum evaporation method. The conductive film 152f can be formed using, for example, a conductive oxide. Alternatively, the conductive film 152f can have a stacked structure of a film using a metal material and a film using a conductive oxide thereon. For example, the conductive film 152f can have a stacked structure of a film using titanium, silver, or an alloy containing silver and a film using a conductive oxide thereon.
[0281] The conductive film 152f can be formed by an ALD method. In this case, the conductive film 152f can be made of an oxide containing one or more elements selected from indium, tin, zinc, gallium, titanium, aluminum, and silicon. The conductive film 152f can be formed by repeating a cycle consisting of introducing a precursor (which may be generally referred to as a precursor or metal precursor), purging the precursor, introducing an oxidizing agent (which may be generally referred to as a reactant, reactant, or non-metal precursor), and purging the oxidizing agent. When forming the conductive film 152f as an oxide film containing multiple metals, such as indium tin oxide, the metal composition can be controlled by varying the number of cycles for each type of precursor.
[0282] For example, when forming an indium tin oxide film as the conductive film 152f, an indium-containing precursor is introduced, the precursor is purged, an oxidizer is introduced, and an In—O film is formed. Next, a tin-containing precursor is introduced, the precursor is purged, and an oxidizer is introduced, and an Sn—O film is formed. Here, by increasing the number of cycles for forming the In—O film compared to the number of cycles for forming the Sn—O film, the number of In atoms contained in the conductive film 152f can be made larger than the number of Sn atoms.
[0283] Furthermore, for example, when a zinc oxide film is formed as the conductive film 152f, a Zn-O film is formed using the above procedure. For example, when an aluminum zinc oxide film is formed as the conductive film 152f, a Zn-O film and an Al-O film are formed using the above procedure. For example, when a titanium oxide film is formed as the conductive film 152f, a Ti-O film is formed using the above procedure. For example, when an indium tin oxide film containing silicon is formed as the conductive film 152f, an In-O film, an Sn-O film, and an Si-O film are formed using the above procedure. For example, when a zinc oxide film containing gallium is formed, a Ga-O film and a Zn-O film are formed using the above procedure.
[0284] Examples of precursors that can be used include indium-containing precursors such as triethylindium, trimethylindium, or [1,1,1-trimethyl-N-(trimethylsilyl)amido]-indium. Examples of precursors that can be used include tin chloride or tetrakis(dimethylamido)tin. Examples of precursors that can be used include zinc-containing precursors such as diethylzinc or dimethylzinc. Examples of precursors that can be used include gallium-containing precursors such as triethylgallium. Examples of precursors that can be used include titanium chloride, tetrakis(dimethylamido)titanium, or tetraisopropyl titanate. Examples of precursors that can be used include aluminum chloride or trimethylaluminum. Examples of precursors that can be used include silicon-containing precursors such as trisilylamine, bis(diethylamino)silane, tris(dimethylamino)silane, bis(tert-butylamino)silane, or bis(ethylmethylamino)silane. Examples of oxidizing agents include water vapor, oxygen plasma, or ozone gas.
[0285] 4A, a resist mask 191 is formed over the conductive film 151f and the conductive film 152f. The resist mask 191 can be formed by applying a photosensitive material (photoresist) and then performing exposure and development.
[0286] 4B, for example, the conductive films 151f and 152f in regions that do not overlap with the resist mask 191 are removed by, for example, etching, specifically, dry etching, to form a pixel electrode including the conductive layer 151 and the conductive layer 152. Note that if the conductive film 151f includes a layer using a conductive oxide such as indium tin oxide, the layer may be removed by wet etching. As a result, the conductive layer 151 and the conductive layer 152 are formed. Note that, for example, when part of the conductive film 151f is removed by dry etching, a recess may be formed in a region of the insulating layer 175 that does not overlap with the conductive layer 151.
[0287] Note that the conductive film 152f may be processed by lithography to form the conductive layers 152R, 152G, 152B, and 152C, and then the conductive film 151f may be processed using the conductive layers 152R, 152G, 152B, and 152C as masks. Specifically, for example, after forming a resist mask, part of the conductive film 152f is removed by etching. The conductive film 152f can be removed by, for example, wet etching. The conductive film 152f may also be removed by dry etching. After that, the conductive film 151f may be removed by wet etching.
[0288] Here, it is preferable to perform hydrophobic treatment on the conductive layer 152. The hydrophobic treatment can change the surface to be treated from hydrophilic to hydrophobic, or can increase the hydrophobicity of the surface to be treated. By performing the hydrophobic treatment on the conductive layer 152, adhesion between the conductive layer 152 and the organic compound layer 103 formed in a later step can be improved, and film peeling can be suppressed. Note that the hydrophobic treatment is not necessarily performed.
[0289] 4(C), the resist mask 191 is removed. The resist mask 191 can be removed by ashing using oxygen plasma, for example. Alternatively, oxygen gas and a Group 18 element such as CF4, C4F8, SF6, CHF3, Cl2, HO, BCl3, or He may be used. Alternatively, the resist mask 191 may be removed by wet etching.
[0290] 4(D), an insulating film 156f, which will later become the insulating layer 156R, the insulating layer 156G, the insulating layer 156B, and the insulating layer 156C, is formed on the conductive layer 151R and the conductive layer 152R, the conductive layer 151G and the conductive layer 152G, the conductive layer 151B and the conductive layer 152B, the conductive layer 151C and the conductive layer 152C, and the insulating layer 175. The insulating film 156f can be formed by, for example, a CVD method, an ALD method, a sputtering method, or a vacuum deposition method.
[0291] The insulating film 156f can be formed using an inorganic material. For example, the insulating film 156f can be formed using an inorganic insulating film such as an oxide insulating film, a nitride insulating film, an oxynitride insulating film, or a nitride oxide insulating film. For example, the insulating film 156f can be formed using an oxide insulating film containing silicon, a nitride insulating film, an oxynitride insulating film, or a nitride oxide insulating film. For example, the insulating film 156f can be formed using silicon oxynitride.
[0292] 4(E), the insulating film 156f is processed to form insulating layers 156R, 156G, 156B, and 156C. For example, the insulating layer 156 can be formed by uniformly etching the upper surface of the insulating film 156f. Such uniform etching and planarization is also called an etch-back process. The insulating layer 156 may also be formed using lithography.
[0293] Next, as shown in FIG. 5(A), an organic compound film 103Rf, which will later become the organic compound layer 103R, is formed on the conductive layer 152R, the conductive layer 152G, the conductive layer 152B, the insulating layer 156R, the insulating layer 156G, the insulating layer 156B, and the insulating layer 175.
[0294] 5A, the organic compound film 103Rf is not formed on the conductive layer 152C. For example, by using a mask for defining the film formation area (also called an area mask or a rough metal mask to distinguish it from a fine metal mask), the organic compound film 103Rf can be formed only in the desired region. By employing a film formation process using an area mask and a processing process using a resist mask, the light-emitting device can be manufactured through a relatively simple process.
[0295] The organic compound film 103Rf can be formed by, for example, a vapor deposition method, specifically a vacuum deposition method, or may be formed by a transfer method, a printing method, an inkjet method, a coating method, or the like.
[0296] Next, as shown in FIG. 5(A), a sacrificial film 158Rf, which will later become the sacrificial layer 158R, and a mask film 159Rf, which will later become the mask layer 159R, are formed in this order on the organic compound film 103Rf, the conductive layer 152C, and the insulating layer 175.
[0297] In this embodiment, an example is shown in which the mask film is formed with a two-layer structure of the sacrificial film 158Rf and the mask film 159Rf, but the mask film may have a single-layer structure or a laminated structure of three or more layers.
[0298] By providing a sacrificial layer on the organic compound film 103Rf, damage to the organic compound film 103Rf during the manufacturing process of the display device can be reduced, and the reliability of the light-emitting device can be improved.
[0299] The sacrificial film 158Rf is made of a film that is highly resistant to the processing conditions of the organic compound film 103Rf, specifically, a film that has a large etching selectivity with respect to the organic compound film 103Rf.The mask film 159Rf is made of a film that has a large etching selectivity with respect to the sacrificial film 158Rf.
[0300] The sacrificial film 158Rf and the mask film 159Rf are formed at a temperature lower than the heat-resistant temperature of the organic compound film 103Rf. The substrate temperatures when forming the sacrificial film 158Rf and the mask film 159Rf are typically 200° C. or lower, preferably 150° C. or lower, more preferably 120° C. or lower, more preferably 100° C. or lower, and even more preferably 80° C. or lower.
[0301] The sacrificial film 158Rf and the mask film 159Rf are preferably made of films that can be removed by wet etching, which can reduce damage to the organic compound film 103Rf when processing the sacrificial film 158Rf and the mask film 159Rf compared to when dry etching is used.
[0302] The sacrificial film 158Rf and the mask film 159Rf can be formed by, for example, sputtering, ALD (thermal ALD, PEALD), CVD, or vacuum deposition. Alternatively, they may be formed by the wet film formation method described above.
[0303] The sacrificial film 158Rf formed on and in contact with the organic compound film 103Rf is preferably formed using a formation method that causes less damage to the organic compound film 103Rf than the mask film 159Rf. For example, it is preferable to form the sacrificial film 158Rf using the ALD method or the vacuum deposition method rather than the sputtering method.
[0304] The sacrificial film 158Rf and the mask film 159Rf may each be made of one or more of a metal film, an alloy film, a metal oxide film, a semiconductor film, an organic insulating film, an inorganic insulating film, or the like.
[0305] The sacrificial film 158Rf and the mask film 159Rf can be made of metal materials such as gold, silver, platinum, magnesium, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, palladium, titanium, aluminum, yttrium, zirconium, and tantalum, or alloy materials containing such metal materials. It is particularly preferable to use a low-melting-point material such as aluminum or silver. Using a metal material capable of blocking ultraviolet rays for one or both of the sacrificial film 158Rf and the mask film 159Rf is preferable because it can prevent ultraviolet rays from being irradiated onto the organic compound film 103Rf and suppress deterioration of the organic compound film 103Rf.
[0306] Furthermore, for the sacrificial film 158Rf and the mask film 159Rf, metal oxides such as In-Ga-Zn oxide, indium oxide, In-Zn oxide, In-Sn oxide, indium titanium oxide (In-Ti oxide), indium tin zinc oxide (In-Sn-Zn oxide), indium titanium zinc oxide (In-Ti-Zn oxide), indium gallium tin zinc oxide (In-Ga-Sn-Zn oxide), and indium tin oxide containing silicon can be used, respectively.
[0307] In addition, instead of the above gallium, an element M (M is one or more elements selected from aluminum, silicon, boron, yttrium, copper, vanadium, beryllium, titanium, iron, nickel, germanium, zirconium, molybdenum, lanthanum, cerium, neodymium, hafnium, tantalum, tungsten, and magnesium) may be used.
[0308] Furthermore, it is preferable to use a film containing a material that has light-shielding properties against light, particularly ultraviolet light, as the sacrificial film and the mask film. As the light-shielding material, various materials such as metals, insulators, semiconductors, and semimetals that have light-shielding properties against ultraviolet light can be used, but since part or all of the sacrificial film and the mask film will be removed in a later step, it is preferable that the film be a film that can be processed by etching, and it is particularly preferable that the film have good processability.
[0309] For the sacrificial film and mask film, it is preferable to use semiconductor materials such as silicon or germanium because they have high compatibility with semiconductor manufacturing processes. Alternatively, oxides or nitrides of the above semiconductor materials can be used. Alternatively, non-metallic materials such as carbon or their compounds can be used. Alternatively, metals such as titanium, tantalum, tungsten, chromium, and aluminum, or alloys containing one or more of these, can be used. Alternatively, oxides containing the above metals such as titanium oxide or chromium oxide, or nitrides such as titanium nitride, chromium nitride, or tantalum nitride can be used.
[0310] By using a film containing a material that blocks ultraviolet light for the sacrificial film and the mask film, it is possible to prevent the organic compound layer from being irradiated with ultraviolet light during, for example, an exposure process, and by preventing the organic compound layer from being damaged by ultraviolet light, the reliability of the light-emitting device can be improved.
[0311] It should be noted that a film containing a material that has a light-shielding property against ultraviolet rays can also achieve the same effect when used as the material for the inorganic insulating film 125f, which will be described later.
[0312] Moreover, various inorganic insulating films can be used for the sacrificial film 158Rf and the mask film 159Rf. In particular, oxide insulating films are preferable because they have higher adhesion to the organic compound film 103Rf than nitride insulating films. For example, inorganic insulating materials such as aluminum oxide, hafnium oxide, and silicon oxide can be used for the sacrificial film 158Rf and the mask film 159Rf. For example, aluminum oxide films can be formed as the sacrificial film 158Rf and the mask film 159Rf using the ALD method. Using the ALD method is preferable because it can reduce damage to the underlying layer (especially the organic compound layer).
[0313] For example, the sacrificial film 158Rf can be an inorganic insulating film (e.g., an aluminum oxide film) formed using the ALD method, and the mask film 159Rf can be an inorganic film (e.g., an In-Ga-Zn oxide film, an aluminum film, or a tungsten film) formed using the sputtering method.
[0314] The same inorganic insulating film can be used for both the sacrificial film 158Rf and the inorganic insulating layer 125 to be formed later. For example, an aluminum oxide film formed using the ALD method can be used for both the sacrificial film 158Rf and the inorganic insulating layer 125. The sacrificial film 158Rf and the inorganic insulating layer 125 may be formed under the same or different film-forming conditions. For example, by forming the sacrificial film 158Rf under the same conditions as the inorganic insulating layer 125, the sacrificial film 158Rf can be an insulating layer with high barrier properties against at least one of water and oxygen. On the other hand, since the sacrificial film 158Rf is a layer that will be mostly or completely removed in a later process, it is preferable that it be easily processed. For this reason, the sacrificial film 158Rf is preferably formed under conditions where the substrate temperature during film formation is lower than that of the inorganic insulating layer 125.
[0315] An organic material may be used for one or both of the sacrificial film 158Rf and the mask film 159Rf. For example, the organic material may be a material that is soluble in a solvent that is chemically stable with respect to at least the film located at the top of the organic compound film 103Rf. In particular, a material that dissolves in water or alcohol is preferably used. When forming a film of such a material, it is preferable to apply the material dissolved in a solvent such as water or alcohol by a wet film formation method, and then perform a heat treatment to evaporate the solvent. In this case, performing the heat treatment under a reduced pressure atmosphere is preferable because it allows the solvent to be removed at a low temperature and in a short time, thereby reducing thermal damage to the organic compound film 103Rf.
[0316] The sacrificial film 158Rf and the mask film 159Rf may each be made of an organic resin such as polyvinyl alcohol (PVA), polyvinyl butyral, polyvinylpyrrolidone, polyethylene glycol, polyglycerin, pullulan, water-soluble cellulose, alcohol-soluble polyamide resin, or a fluororesin such as a perfluoropolymer.
[0317] For example, the sacrificial film 158Rf may be an organic film (e.g., a PVA film) formed using either a vapor deposition method or the above-mentioned wet film formation method, and the mask film 159Rf may be an inorganic film (e.g., a silicon nitride film) formed using a sputtering method.
[0318] 5(A), a resist mask 190R is formed on the mask film 159Rf. The resist mask 190R can be formed by applying a photosensitive material (photoresist) and then performing exposure and development.
[0319] The resist mask 190R may be made of either a positive resist material or a negative resist material.
[0320] The resist mask 190R is provided in a position overlapping with the conductive layer 152R. The resist mask 190R is preferably also provided in a position overlapping with the conductive layer 152C. This can prevent the conductive layer 152C from being damaged during the manufacturing process of the display device. Note that the resist mask 190R does not necessarily have to be provided on the conductive layer 152C. Furthermore, as shown in the cross-sectional view between B1 and B2 in FIG. 5A, the resist mask 190R is preferably provided so as to cover from the end of the organic compound film 103Rf to the end of the conductive layer 152C (the end on the organic compound film 103Rf side).
[0321] 5(B), a resist mask 190R is used to remove a portion of the mask film 159Rf to form a mask layer 159R. The mask layer 159R remains on the conductive layer 152R and the conductive layer 152C. The resist mask 190R is then removed. The mask layer 159R is used as a mask (also referred to as a hard mask) to remove a portion of the sacrificial film 158Rf to form a sacrificial layer 158R.
[0322] The sacrificial film 158Rf and the mask film 159Rf can be processed by wet etching or dry etching, respectively. The sacrificial film 158Rf and the mask film 159Rf are preferably processed by isotropic etching.
[0323] By using the wet etching method, damage to the organic compound film 103Rf during processing of the sacrificial film 158Rf and the mask film 159Rf can be reduced compared to when using the dry etching method. When using the wet etching method, it is preferable to use a chemical solution such as a developer, a tetramethylammonium hydroxide (TMAH) aqueous solution, diluted hydrofluoric acid, oxalic acid, phosphoric acid, acetic acid, nitric acid, or a mixture thereof.
[0324] In processing the mask film 159Rf, the organic compound film 103Rf is not exposed, so the range of processing methods to be selected is wider than in processing the sacrificial film 158Rf. Specifically, even when a gas containing oxygen is used as an etching gas in processing the mask film 159Rf, deterioration of the organic compound film 103Rf can be further suppressed.
[0325] Furthermore, when dry etching is used to process the sacrificial film 158Rf, deterioration of the organic compound film 103Rf can be suppressed by not using a gas containing oxygen as the etching gas. When dry etching is used, it is preferable to use a gas containing a Group 18 element such as CF4, C4F8, SF6, CHF3, Cl2, HO, BCl3, or He as the etching gas.
[0326] For example, when an aluminum oxide film formed by ALD is used as the sacrificial film 158Rf, a portion of the sacrificial film 158Rf can be removed by dry etching using CHF3 and He, or CHF3, He, and CH4. When an In-Ga-Zn oxide film formed by sputtering is used as the mask film 159Rf, a portion of the mask film 159Rf can be removed by wet etching using diluted phosphoric acid. Alternatively, a portion of the mask film 159Rf may be removed by dry etching using CH4 and Ar. Alternatively, a portion of the mask film 159Rf can be removed by wet etching using diluted phosphoric acid. When a tungsten film formed by sputtering is used as the mask film 159Rf, a portion of the mask film 159Rf can be removed by dry etching using SF6, CF4 and O2, or CF4, Cl2, and O2.
[0327] The resist mask 190R can be removed by the same method as the resist mask 191. For example, it can be removed by ashing using oxygen plasma. Alternatively, oxygen gas and a Group 18 element such as CF4, C4F8, SF6, CHF3, Cl2, H2O, BCl3, or He may be used. Alternatively, the resist mask 190R may be removed by wet etching. At this time, since the sacrificial film 158Rf is located on the outermost surface and the organic compound film 103Rf is not exposed, damage to the organic compound film 103Rf can be suppressed in the process of removing the resist mask 190R. Furthermore, the range of options for removing the resist mask 190R can be expanded.
[0328] 5(B), the organic compound film 103Rf is processed to form the organic compound layer 103R. For example, the mask layer 159R and the sacrificial layer 158R are used as a hard mask to remove a part of the organic compound film 103Rf, thereby forming the organic compound layer 103R.
[0329] 5B, a stacked structure of the organic compound layer 103R, the sacrificial layer 158R, and the mask layer 159R remains on the conductive layer 152R. Also, the conductive layers 152G and 152B are exposed.
[0330] 5B shows an example in which the edge of the organic compound layer 103R is located inside the edge of the conductive layer 152R. This structure enables miniaturization of pixels, enabling the creation of a high-resolution display. Although not shown in FIG. 5B, the etching process may result in the formation of a recess in a region of the insulating layer 175 that does not overlap with the organic compound layer 103R.
[0331] As described above, the resist mask 190R is preferably provided to cover the area between the dashed-dotted lines B1-B2 from the end of the organic compound layer 103R to the end of the conductive layer 152C (the end on the organic compound layer 103R side). As a result, as shown in FIG. 5B, the sacrificial layer 158R and the mask layer 159R are provided to cover the area between the dashed-dotted lines B1-B2 from the end of the organic compound layer 103R to the end of the conductive layer 152C (the end on the organic compound layer 103R side). This prevents the insulating layer 175 from being exposed between the dashed-dotted lines B1-B2, for example. This prevents the conductive layer 179 from being exposed when parts of the insulating layers 175, 174, and 173 are removed by etching or the like. This prevents the conductive layer 179 from being unintentionally electrically connected to other conductive layers. For example, this prevents a short circuit between the conductive layer 179 and the common electrode 155, which will be formed in a later step.
[0332] The organic compound film 103Rf is preferably processed by anisotropic etching, particularly anisotropic dry etching, or wet etching may be used.
[0333] When dry etching is used, deterioration of the organic compound film 103Rf can be suppressed by not using an oxygen-containing gas as the etching gas.
[0334] Alternatively, an etching gas containing oxygen may be used. The etching rate can be increased by using an etching gas containing oxygen. Therefore, etching can be performed under low power conditions while maintaining a sufficiently high etching rate. This can reduce damage to the organic compound film 103Rf. Furthermore, problems such as adhesion of reaction products generated during etching can be reduced.
[0335] When dry etching is used, it is preferable to use a gas containing one or more of H2, CF4, C4F8, SF6, CHF3, Cl2, H2O, BCl3, or Group 18 elements such as He and Ar as the etching gas. Alternatively, it is preferable to use a gas containing one or more of these elements and oxygen as the etching gas. Alternatively, oxygen gas may be used as the etching gas. Specifically, for example, a gas containing H2 and Ar, or a gas containing CF4 and He can be used as the etching gas. Alternatively, for example, a gas containing CF4, He, and oxygen can be used as the etching gas. Alternatively, for example, a gas containing H2 and Ar, or a gas containing oxygen can be used as the etching gas.
[0336] As described above, in one embodiment of the present invention, the resist mask 190R is formed over the mask film 159Rf, and part of the mask film 159Rf is removed using the resist mask 190R to form the mask layer 159R. Then, part of the organic compound film 103Rf is removed using the mask layer 159R as a hard mask to form the organic compound layer 103R. Therefore, it can be said that the organic compound layer 103R is formed by processing the organic compound film 103Rf using a lithography method. Note that part of the organic compound film 103Rf may be removed using the resist mask 190R. Then, the resist mask 190R may be removed.
[0337] Next, it is preferable to perform, for example, a hydrophobic treatment on the conductive layer 152G. When processing the organic compound film 103Rf, for example, the surface state of the conductive layer 152G may change to a hydrophilic state. For example, by performing a hydrophobic treatment on the conductive layer 152G, it is possible to improve the adhesion between the conductive layer 152G and a layer (here, the organic compound layer 103G) formed in a later step, and to suppress film peeling. Note that the hydrophobic treatment is not necessarily required.
[0338] Next, as shown in FIG. 6(A), an organic compound film 103Gf, which will later become the organic compound layer 103G, is formed on the conductive layer 152G, the conductive layer 152B, the insulating layer 156R, the insulating layer 156G, the insulating layer 156B, the mask layer 159R, and the insulating layer 175.
[0339] The organic compound film 103Gf can be formed by the same method as that used to form the organic compound film 103Rf, and can have the same structure as the organic compound film 103Rf.
[0340] 6A, a sacrificial film 158Gf, which will later become the sacrificial layer 158G, and a mask film 159Gf, which will later become the mask layer 159G, are sequentially formed on the organic compound film 103Gf and the mask layer 159R. A resist mask 190G is then formed. The materials and formation methods for the sacrificial film 158Gf and the mask film 159Gf are the same as those applicable to the sacrificial film 158Rf and the mask film 159Rf. The materials and formation methods for the resist mask 190G are the same as those applicable to the resist mask 190R.
[0341] The resist mask 190G is provided in a position overlapping with the conductive layer 152G.
[0342] 6(B), a resist mask 190G is used to remove a portion of the mask film 159Gf to form a mask layer 159G. The mask layer 159G remains on the conductive layer 152G. The resist mask 190G is then removed. The mask layer 159G is then used as a mask to remove a portion of the sacrificial film 158Gf to form a sacrificial layer 158G. The organic compound film 103Gf is then processed to form an organic compound layer 103G. For example, the mask layer 159G and the sacrificial layer 158G are used as hard masks to remove a portion of the organic compound film 103Gf to form the organic compound layer 103G.
[0343] 6B, a stacked structure of the organic compound layer 103G, the sacrificial layer 158G, and the mask layer 159G remains on the conductive layer 152G, and the mask layer 159R and the conductive layer 152B are exposed.
[0344] Next, it is preferable to perform, for example, a hydrophobic treatment on the conductive layer 152B. When processing the organic compound film 103Gf, for example, the surface state of the conductive layer 152B may change to a hydrophilic state. For example, by performing a hydrophobic treatment on the conductive layer 152B, it is possible to improve the adhesion between the conductive layer 152B and a layer (here, the organic compound layer 103B) formed in a later step, and to suppress film peeling. Note that the hydrophobic treatment is not necessarily required.
[0345] Next, as shown in FIG. 6(C), an organic compound film 103Bf, which will later become the organic compound layer 103B, is formed on the conductive layer 152B, the mask layer 159R, the insulating layer 156R, the insulating layer 156G, the insulating layer 156B, the mask layer 159G, and the insulating layer 175.
[0346] The organic compound film 103Bf can be formed by the same method as that used to form the organic compound film 103Rf, and can have the same structure as the organic compound film 103Rf.
[0347] 6(C), a sacrificial film 158Bf, which will later become the sacrificial layer 158B, and a mask film 159Bf, which will later become the mask layer 159B, are sequentially formed on the organic compound film 103Bf and the mask layer 159R. A resist mask 190B is then formed. The materials and formation methods for the sacrificial film 158Bf and the mask film 159Bf are the same as those applicable to the sacrificial film 158Rf and the mask film 159Rf. The materials and formation methods for the resist mask 190B are the same as those applicable to the resist mask 190R.
[0348] The resist mask 190B is provided in a position overlapping with the conductive layer 152B.
[0349] 6(D), a resist mask 190B is used to remove a portion of the mask film 159Bf to form a mask layer 159B. The mask layer 159B remains on the conductive layer 152B. The resist mask 190B is then removed. The mask layer 159B is then used as a mask to remove a portion of the sacrificial film 158Bf to form a sacrificial layer 158B. The organic compound film 103Bf is then processed to form the organic compound layer 103B. For example, the mask layer 159B and the sacrificial layer 158B are used as hard masks to remove a portion of the organic compound film 103Bf to form the organic compound layer 103B.
[0350] 6(D), a stacked structure of the organic compound layer 103B, the sacrificial layer 158B, and the mask layer 159B remains on the conductive layer 152B, and the mask layers 159R and 159G are exposed.
[0351] It is preferable that the side surfaces of the organic compound layer 103R, the organic compound layer 103G, and the organic compound layer 103B are perpendicular or approximately perpendicular to the surface on which they are formed. For example, it is preferable that the angle formed between the surface on which they are formed and these side surfaces is 60 degrees or more and 90 degrees or less.
[0352] As described above, the distance between adjacent pairs of the organic compound layers 103R, 103G, and 103B formed using lithography can be narrowed to 8 μm or less, 5 μm or less, 3 μm or less, 2 μm or less, or 1 μm or less. Here, the distance can be defined, for example, as the distance between the opposing ends of adjacent pairs of the organic compound layers 103R, 103G, and 103B. By narrowing the distance between the island-shaped organic compound layers in this manner, a display device with high definition and a large aperture ratio can be provided. Furthermore, the distance between the first electrodes of adjacent light-emitting devices can also be narrowed, for example, to 10 μm or less, 8 μm or less, 5 μm or less, 3 μm or less, or 2 μm or less. It is preferable that the distance between the first electrodes of adjacent light-emitting devices be 2 μm or more and 5 μm or less.
[0353] 7A, it is preferable to remove the mask layers 159R, 159G, and 159B. Depending on the subsequent process, the sacrificial layers 158R, 158G, and 158B, and the mask layers 159R, 159G, and 159B may remain in the display device. By removing the mask layers 159R, 159G, and 159B at this stage, it is possible to prevent the mask layers 159R, 159G, and 159B from remaining in the display device. For example, if a conductive material is used for the mask layers 159R, 159G, and 159B, removing the mask layers 159R, 159G, and 159B in advance can prevent leakage current and capacitance from being generated by the remaining mask layers 159R, 159G, and 159B.
[0354] Although the present embodiment will be described taking as an example a case where the mask layers 159R, 159G, and 159B are removed, it is not necessary to remove the mask layers 159R, 159G, and 159B. For example, if the mask layers 159R, 159G, and 159B contain the aforementioned material that has a light-blocking property against ultraviolet light, it is preferable to proceed to the next step without removing them, because this protects the organic compound layer from ultraviolet light.
[0355] The mask layer removal process can be performed using the same method as the mask film processing process. In particular, wet etching can reduce damage to the organic compound layers 103R, 103G, and 103B when removing the mask layer compared to dry etching.
[0356] The mask layer may also be removed by dissolving it in a solvent such as water or alcohol, such as ethyl alcohol, methyl alcohol, isopropyl alcohol (IPA), or glycerin.
[0357] After removing the mask layer, a drying treatment may be performed to remove water contained in the organic compound layer 103R, the organic compound layer 103G, and the organic compound layer 103B, as well as water adsorbed on the surfaces of the organic compound layer 103R, the organic compound layer 103G, and the organic compound layer 103B. For example, a heat treatment can be performed in an inert gas atmosphere or a reduced-pressure atmosphere. The heat treatment can be performed at a substrate temperature of 50°C or higher and 200°C or lower, preferably 60°C or higher and 150°C or lower, and more preferably 70°C or higher and 120°C or lower. A reduced-pressure atmosphere is preferred because it enables drying at a lower temperature.
[0358] Next, as shown in FIG. 7(B), an inorganic insulating film 125f, which will later become the inorganic insulating layer 125, is formed to cover the organic compound layer 103R, the organic compound layer 103G, the organic compound layer 103B, the sacrificial layer 158R, the sacrificial layer 158G, and the sacrificial layer 158B.
[0359] As will be described later, an insulating film 127f, which will later become the insulating layer 127, is formed in contact with the upper surface of the inorganic insulating film 125f. For this reason, it is preferable that the upper surface of the inorganic insulating film 125f has a high affinity with the material used for the insulating film (e.g., a photosensitive resin composition containing an acrylic resin). To improve this affinity, it is preferable to hydrophobize (or increase the hydrophobicity of) the upper surface of the inorganic insulating film 125f by performing a surface treatment. For example, it is preferable to perform the treatment using a silylating agent such as hexamethyldisilazane (HMDS). By hydrophobizing the upper surface of the inorganic insulating film 125f in this way, the insulating film 127f can be formed with good adhesion. Note that the surface treatment may be the hydrophobization treatment described above.
[0360] Subsequently, as shown in FIG. 7(C), an insulating film 127f, which will later become the insulating layer 127, is formed on the inorganic insulating film 125f.
[0361] The inorganic insulating film 125f and the insulating film 127f are preferably formed by a formation method that causes less damage to the organic compound layer 103R, the organic compound layer 103G, and the organic compound layer 103B. In particular, since the inorganic insulating film 125f is formed in contact with the side surfaces of the organic compound layer 103R, the organic compound layer 103G, and the organic compound layer 103B, it is preferably formed by a formation method that causes less damage to the organic compound layer 103R, the organic compound layer 103G, and the organic compound layer 103B than the insulating film 127f.
[0362] The inorganic insulating film 125f and the insulating film 127f are formed at a temperature lower than the heat-resistant temperatures of the organic compound layer 103R, the organic compound layer 103G, and the organic compound layer 103B, respectively. By increasing the substrate temperature during film formation, the inorganic insulating film 125f can be formed into a film with a low impurity concentration and a high barrier property against at least one of water and oxygen, even if it is thin.
[0363] The substrate temperature when forming the inorganic insulating film 125f and the insulating film 127f is preferably 60°C or higher, 80°C or higher, 100°C or higher, or 120°C or higher, and 200°C or lower, 180°C or lower, 160°C or lower, 150°C or lower, or 140°C or lower, respectively.
[0364] As the inorganic insulating film 125f, it is preferable to form an insulating film having a thickness of 3 nm or more, 5 nm or more, or 10 nm or more, and 200 nm or less, 150 nm or less, 100 nm or less, or 50 nm or less within the above substrate temperature range.
[0365] The inorganic insulating film 125f is preferably formed by, for example, the ALD method. The ALD method is preferable because it can reduce film formation damage and also allows for the formation of a film with high coverage. The inorganic insulating film 125f is preferably formed as an aluminum oxide film by, for example, the ALD method.
[0366] Alternatively, the inorganic insulating film 125f may be formed by sputtering, CVD, or PECVD, which have a faster film formation rate than ALD, thereby enabling a highly reliable display device to be manufactured with high productivity.
[0367] The insulating film 127f is preferably formed by the wet film formation method described above. The insulating film 127f is preferably formed by, for example, spin coating using a photosensitive material, more specifically, using a photosensitive resin composition containing an acrylic resin.
[0368] The insulating film 127f is preferably formed using a resin composition containing, for example, a polymer, an acid generator, and a solvent. The polymer is formed using one or more types of monomers and has a structure in which one or more types of structural units (also referred to as constituent units) are regularly or irregularly repeated. As the acid generator, one or both of a compound that generates an acid when irradiated with light and a compound that generates an acid when heated can be used. The resin composition may further contain one or more of a photosensitizer, a sensitizer, a catalyst, an adhesion aid, a surfactant, and an antioxidant.
[0369] Furthermore, heat treatment (also referred to as pre-baking) is preferably performed after the insulating film 127f is formed. The heat treatment is performed at a temperature lower than the heat resistance temperature of the organic compound layer 103R, the organic compound layer 103G, and the organic compound layer 103B. The substrate temperature during the heat treatment is preferably 50° C. to 200° C., more preferably 60° C. to 150° C., and still more preferably 70° C. to 120° C. This allows the solvent contained in the insulating film 127f to be removed.
[0370] Next, exposure is performed to expose a portion of the insulating film 127f to visible light or ultraviolet light. If a positive-type photosensitive resin composition containing an acrylic resin is used for the insulating film 127f, visible light or ultraviolet light is irradiated onto the region where the insulating layer 127 will not be formed in a later process. The insulating layer 127 is formed in the region sandwiched between any two of the conductive layers 152R, 152G, and 152B, and around the conductive layer 152C. Therefore, visible light or ultraviolet light is irradiated onto the conductive layers 152R, 152G, 152B, and 152C. If a negative-type photosensitive material is used for the insulating film 127f, visible light or ultraviolet light is irradiated onto the region where the insulating layer 127 will be formed.
[0371] The exposed region of the insulating film 127f can control the width of the insulating layer 127 to be formed later. In this embodiment, the insulating layer 127 is processed so as to have a portion overlapping the upper surface of the conductive layer 151.
[0372] The light used for exposure preferably contains i-line (wavelength 365 nm), and may contain at least one of g-line (wavelength 436 nm) and h-line (wavelength 405 nm).
[0373] Here, by providing an oxygen barrier insulating layer (e.g., an aluminum oxide film) as one or both of the sacrificial layer 158 (the sacrificial layer 158R, the sacrificial layer 158G, and the sacrificial layer 158B) and the inorganic insulating film 125f, it is possible to reduce the diffusion of oxygen into the organic compound layer 103R, the organic compound layer 103G, and the organic compound layer 103B. When the organic compound layer is irradiated with light (visible light or ultraviolet light), the organic compound contained in the organic compound layer becomes excited, which may promote a reaction with oxygen contained in the atmosphere. More specifically, when light (visible light or ultraviolet light) is irradiated to the organic compound layer in an oxygen-containing atmosphere, oxygen may bond to the organic compound contained in the organic compound layer. By providing the sacrificial layer 158 and the inorganic insulating film 125f on the island-shaped organic compound layer, it is possible to reduce the bonding of oxygen in the atmosphere to the organic compound contained in the organic compound layer.
[0374] 8(A), development is performed to remove the exposed region of the insulating film 127f, thereby forming the insulating layer 127a. The insulating layer 127a is formed in a region sandwiched between any two of the conductive layers 152R, 152G, and 152B, and in a region surrounding the conductive layer 152C. When an acrylic resin is used for the insulating film 127f, an alkaline solution, such as TMAH, can be used as the developer.
[0375] Subsequently, residues (so-called scum) remaining after development may be removed, for example, by ashing using oxygen plasma.
[0376] Etching may be performed to adjust the height of the surface of the insulating layer 127a. The insulating layer 127a may be processed by ashing using oxygen plasma, for example. Even when a non-photosensitive material is used as the insulating film 127f, the height of the surface of the insulating film 127f can be adjusted by ashing, for example.
[0377] 8(B), an etching process is performed using the insulating layer 127a as a mask to remove a portion of the inorganic insulating film 125f and reduce the thickness of a portion of the sacrificial layers 158R, 158G, and 158B. As a result, the inorganic insulating layer 125 is formed below the insulating layer 127a. Furthermore, the surfaces of the thin portions of the sacrificial layers 158R, 158G, and 158B are exposed. Note that, hereinafter, the etching process using the insulating layer 127a as a mask may be referred to as the first etching process.
[0378] The first etching process can be performed by dry etching or wet etching. Note that, when the inorganic insulating film 125f is formed using the same material as the sacrificial layers 158R, 158G, and 158B, the first etching process can be performed all at once, which is preferable.
[0379] By performing etching using insulating layer 127a, which has tapered side surfaces, as a mask, the side surfaces of inorganic insulating layer 125 and the upper end portions of the side surfaces of sacrificial layers 158R, 158G, and 158B can be tapered relatively easily.
[0380] When dry etching is performed, it is preferable to use a chlorine-based gas. Examples of chlorine-based gases that can be used include Cl2, BCl3, SiCl4, and CCl4, either singly or in combination. Furthermore, oxygen gas, hydrogen gas, helium gas, and argon gas can be added to the chlorine-based gas, either singly or in combination. By using dry etching, thin-film regions of the sacrificial layers 158R, 158G, and 158B can be formed with good in-plane uniformity.
[0381] The dry etching apparatus may be a dry etching apparatus having a high-density plasma source. The dry etching apparatus having a high-density plasma source may be, for example, an inductively coupled plasma (ICP) etching apparatus. Alternatively, a capacitively coupled plasma (CCP) etching apparatus having parallel-plate electrodes may be used. The capacitively coupled plasma etching apparatus having parallel-plate electrodes may be configured to apply a high-frequency voltage to one of the parallel-plate electrodes, or to apply a plurality of different high-frequency voltages to one of the parallel-plate electrodes, or to apply a high-frequency voltage of the same frequency to each of the parallel-plate electrodes, or to apply high-frequency voltages of different frequencies to each of the parallel-plate electrodes.
[0382] Furthermore, when dry etching is performed, by-products and the like produced by the dry etching may be deposited on the upper surface and side surfaces of insulating layer 127a, etc. Therefore, components contained in the etching gas, components contained in inorganic insulating film 125f, and components contained in sacrificial layers 158R, 158G, and 158B may be contained in insulating layer 127 after the display device is completed.
[0383] Furthermore, it is preferable to perform the first etching process by wet etching. Using wet etching can reduce damage to the organic compound layer 103R, the organic compound layer 103G, and the organic compound layer 103B compared to using dry etching. For example, wet etching can be performed using an alkaline solution. For example, TMAH, an alkaline solution, can be used for wet etching of an aluminum oxide film. In this case, wet etching can be performed by a puddle method. Note that, if the inorganic insulating film 125f is formed using the same material as the sacrificial layers 158R, 158G, and 158B, the above-mentioned etching process can be performed all at once, which is preferable.
[0384] In the first etching process, the sacrificial layers 158R, 158G, and 158B are not completely removed, and the etching process is stopped when the film thicknesses of the sacrificial layers 158R, 158G, and 158B are reduced. In this manner, by leaving the sacrificial layers 158R, 158G, and 158B on the organic compound layers 103R, 103G, and 103B, respectively, it is possible to prevent the organic compound layers 103R, 103G, and 103B from being damaged in subsequent processes.
[0385] Next, the entire substrate is exposed to visible light or ultraviolet light, and the insulating layer 127a is preferably irradiated with the energy density of 0 mJ / cm. 2 Larger, 800mJ / cm 2 It is preferable that the dose is 0 mJ / cm or less, and 2 Larger, 500mJ / cm 2 It is more preferable to perform the following. By performing such exposure after development, the transparency of the insulating layer 127a can be improved in some cases. Furthermore, the substrate temperature required for heat treatment to transform the insulating layer 127a into a tapered shape in a later step can be reduced in some cases.
[0386] Here, the presence of an oxygen barrier insulating layer (e.g., an aluminum oxide film) as the sacrificial layers 158R, 158G, and 158B can reduce oxygen diffusion into the organic compound layers 103R, 103G, and 103B. When the organic compound layers are irradiated with light (visible light or ultraviolet light), the organic compounds contained in the organic compound layers become excited, which may promote a reaction with oxygen contained in the atmosphere. More specifically, when light (visible light or ultraviolet light) is irradiated onto an organic compound layer in an oxygen-containing atmosphere, oxygen may bond to the organic compounds contained in the organic compound layer. By providing the sacrificial layers 158R, 158G, and 158B on the island-shaped organic compound layers, it is possible to reduce oxygen from the atmosphere bonding to the organic compounds contained in the organic compound layers.
[0387] Next, heat treatment (also referred to as post-baking) is performed. By performing the heat treatment, the insulating layer 127a can be transformed into the insulating layer 127 having tapered side surfaces (FIG. 8C). The heat treatment is performed at a temperature lower than the upper temperature limit of the organic compound layer. The heat treatment can be performed at a substrate temperature of 50° C. to 200° C., preferably 60° C. to 150° C., more preferably 70° C. to 130° C. The heating atmosphere may be an air atmosphere or an inert gas atmosphere. The heating atmosphere may be an atmospheric pressure atmosphere or a reduced-pressure atmosphere. The substrate temperature in this heat treatment is preferably higher than that in the heat treatment (pre-baking) performed after the formation of the insulating film 127f. This can improve adhesion between the insulating layer 127 and the inorganic insulating layer 125 and also improve the corrosion resistance of the insulating layer 127.
[0388] By not completely removing the sacrificial layers 158R, 158G, and 158B in the first etching process and leaving the sacrificial layers 158R, 158G, and 158B in a thinner state, the organic compound layers 103R, 103G, and 103B can be prevented from being damaged and deteriorated in the heat treatment, thereby improving the reliability of the light-emitting device.
[0389] Depending on the material of the insulating layer 127 and the temperature, time, and atmosphere of post-baking, a concave curved shape may be formed on the side surface of the insulating layer 127. For example, the higher the temperature or the longer the post-baking time, the more likely the shape of the insulating layer 127 is to change, and a concave curved shape may be formed.
[0390] 9(A), an etching process is performed using the insulating layer 127 as a mask to remove portions of the sacrificial layer 158R, the sacrificial layer 158G, and the sacrificial layer 158B. Note that a portion of the inorganic insulating layer 125 may also be removed. As a result, openings are formed in the sacrificial layer 158R, the sacrificial layer 158G, and the sacrificial layer 158B, respectively, and the upper surfaces of the organic compound layer 103R, the organic compound layer 103G, the organic compound layer 103B, and the conductive layer 152C are exposed. Note that, hereinafter, the etching process using the insulating layer 127 as a mask may be referred to as a second etching process.
[0391] The end of the inorganic insulating layer 125 is covered with the insulating layer 127. Also, Fig. 9(A) shows an example in which a part of the end of the sacrificial layer 158G (specifically, the tapered portion formed by the first etching process) is covered with the insulating layer 127, and the tapered portion formed by the second etching process is exposed.
[0392] If the inorganic insulating layer 125 and the mask layer are etched together after post-baking without the first etching process, side etching may cause the inorganic insulating layer 125 and the mask layer below the edge of the insulating layer 127 to disappear, forming a cavity. Such a cavity may cause unevenness on the surface on which the common electrode 155 is formed, making the common electrode 155 prone to step discontinuities. Even if the inorganic insulating layer 125 and the mask layer are side-etched in the first etching process, post-baking can subsequently fill the cavity with the insulating layer 127. The second etching process then etches the thinner mask layer, reducing the amount of side etching and making it less likely for a cavity to form. Even if a cavity does form, it can be extremely small. This allows for a flatter surface on which the common electrode 155 is formed.
[0393] The insulating layer 127 may cover the entire end of the sacrificial layer 158G. For example, the end of the insulating layer 127 may droop and cover the end of the sacrificial layer 158G. Furthermore, for example, the end of the insulating layer 127 may contact the upper surface of at least one of the organic compound layer 103R, the organic compound layer 103G, and the organic compound layer 103B. As described above, if the developed insulating layer 127a is not exposed to light, the shape of the insulating layer 127 may be easily deformed.
[0394] The second etching process is performed by wet etching. By using the wet etching method, damage to the organic compound layer 103R, the organic compound layer 103G, and the organic compound layer 103B can be reduced compared to when using the dry etching method. The wet etching can be performed using an alkaline solution such as TMAH.
[0395] On the other hand, when the second etching process is performed using a wet etching method, if gaps are present between the organic compound layer 103 and the sacrificial layer 158, between the organic compound layer 103 and the inorganic insulating layer 125, or at the interface between the organic compound layer 103 and the insulating layer 175 due to, for example, adhesion issues between the organic compound layer 103 and other layers, the chemical solution used in the second etching process may penetrate into these gaps and come into contact with the pixel electrodes. If the chemical solution comes into contact with both the conductive layer 151 and the conductive layer 152, the conductive layer with the lower natural potential may corrode due to galvanic corrosion. For example, if aluminum is used for the conductive layer 151 and indium tin oxide is used for the conductive layer 152, the conductive layer 152 may corrode. As a result, the yield of the display device may decrease. Furthermore, the reliability of the display device may also decrease.
[0396] As described above, by forming the insulating layer 156 so as to have an area overlapping with the side surface of the conductive layer 151 and by forming the insulating layer 156 so as to cover the conductive layer 151 and the conductive layer 152, it is possible to prevent the inorganic insulating layer 125 from being broken, and therefore it is possible to prevent the chemical solution from coming into contact with the underlying structure such as the conductive layer 151 during the second etching process, for example. This makes it possible to prevent corrosion of the pixel electrode.
[0397] As described above, by providing the insulating layer 127, the inorganic insulating layer 125, the sacrificial layer 158R, the sacrificial layer 158G, and the sacrificial layer 158B, it is possible to prevent connection defects caused by disconnected portions of the common electrode 155 between the light-emitting devices and an increase in electrical resistance caused by locally thin portions of the common electrode 155. As a result, the display quality of the display device of one embodiment of the present invention can be improved.
[0398] Furthermore, after exposing portions of the organic compound layer 103R, the organic compound layer 103G, and the organic compound layer 103B, a further heat treatment is performed. This heat treatment can remove water contained in each organic compound layer, water adsorbed to the surface of each organic compound layer, and the like. This heat treatment may also change the shape of the insulating layer 127. Specifically, the insulating layer 127 may extend to cover at least one of the ends of the inorganic insulating layer 125, the ends of the sacrificial layer 158R, the sacrificial layer 158G, and the sacrificial layer 158B, and the top surfaces of the organic compound layer 103R, the organic compound layer 103G, and the organic compound layer 103B.
[0399] If the heat treatment temperature is too low, water contained in each organic compound layer and water adsorbed on the surface of each organic compound layer cannot be sufficiently removed. Furthermore, if the heat treatment temperature is too high, the organic compound layer 103 may be deteriorated and the shape of the insulating layer 127 may be excessively changed. Therefore, the heat treatment is preferably performed at a temperature higher than the temperature at which water desorbs from the organic compound layer 103 but lower than the glass transition temperature of the organic compound contained in the organic compound layer 103, and more preferably lower than the glass transition temperature of the organic compound contained on the upper surface of the organic compound layer 103. Specifically, the heat treatment is preferably performed at a substrate temperature of 80°C to 130°C, preferably 90°C to 120°C, more preferably 100°C to 120°C, and even more preferably 100°C to 110°C. The heating atmosphere may be an air atmosphere or an inert gas atmosphere. The heating atmosphere may be an atmospheric pressure atmosphere or a reduced pressure atmosphere. However, a reduced pressure atmosphere is preferred to prevent re-adsorption of water desorbed from the organic compound layer 103.
[0400] This heat treatment can sufficiently remove water contained in each organic compound layer and water adsorbed on the surface of each organic compound layer without causing deterioration of the organic compound layer 103R, the organic compound layer 103G, and the organic compound layer 103B, or excessive change in the shape of the insulating layer 127. This can prevent deterioration in the characteristics of the light-emitting device.
[0401] 9(B), the common layer 104 and the common electrode 155 are formed on the organic compound layer 103R, the organic compound layer 103G, the organic compound layer 103B, the conductive layer 152C, and the insulating layer 127. The common layer 104 and the common electrode 155 can be formed by a method such as sputtering or vacuum deposition. The common layer 104 may be formed by deposition, and the common electrode 155 may be formed by sputtering.
[0402] 9(C), a protective layer 131 is formed on the common electrode 155. The protective layer 131 can be formed by a method such as a vacuum deposition method, a sputtering method, a CVD method, or an ALD method.
[0403] Subsequently, the substrate 120 is attached over the protective layer 131 using the resin layer 122, whereby a display device can be manufactured. As described above, in the method for manufacturing a display device of one embodiment of the present invention, the insulating layer 156 is provided on the side surfaces of the conductive layer 151 and the conductive layer 152. This can increase the yield of the display device and suppress the occurrence of defects.
[0404] As described above, in the manufacturing method of a display device according to one embodiment of the present invention, the island-shaped organic compound layers 103R, 103G, and 103B are formed by forming films over the entire surface and then processing them, rather than using a fine metal mask. This allows the island-shaped layers to be formed with uniform thicknesses. This allows a high-resolution display device or a display device with a high aperture ratio to be realized. Furthermore, even when the resolution or aperture ratio is high and the distance between subpixels is extremely short, the organic compound layers 103R, 103G, and 103B can be prevented from contacting each other in adjacent subpixels. Therefore, leakage current between subpixels can be suppressed. This prevents crosstalk and realizes a display device with extremely high contrast. Furthermore, a display device with excellent characteristics can be provided, even in a display device including tandem light-emitting devices fabricated by lithography.
[0405] The structure of this embodiment can be used in appropriate combination with structures of other embodiments.
[0406] (Fourth embodiment) In this embodiment, a light-emitting device of one embodiment of the present invention will be described with reference to FIGS. 10A to 10G and 11A to 11I.
[0407] [Pixel layout] In this embodiment, pixel layouts different from that shown in Fig. 3(A) will be mainly described. There are no particular limitations on the arrangement of sub-pixels, and various methods can be applied. Examples of sub-pixel arrangements include a stripe arrangement, an S-stripe arrangement, a matrix arrangement, a delta arrangement, a Bayer arrangement, and a pentile arrangement.
[0408] The top shape of the sub-pixels shown in the drawings in this embodiment mode corresponds to the top shape of the light-emitting region.
[0409] The top surface shape of the subpixel may be, for example, a triangle, a quadrangle (including a rectangle and a square), a polygon such as a pentagon, a polygon with rounded corners, an ellipse, or a circle.
[0410] Furthermore, the layout of the circuits constituting the sub-pixels is not limited to the range of the sub-pixels shown in the drawings, and may be arranged outside of the range.
[0411] An S-stripe arrangement is applied to the pixel 178 shown in Fig. 10(A). The pixel 178 shown in Fig. 10(A) is composed of three subpixels: a subpixel 110R, a subpixel 110G, and a subpixel 110B.
[0412] The pixel 178 shown in FIG. 10B includes a subpixel 110R having a generally trapezoidal or triangular top surface shape with rounded corners, a subpixel 110G having a generally trapezoidal or triangular top surface shape with rounded corners, and a subpixel 110B having a generally rectangular or hexagonal top surface shape with rounded corners. The subpixel 110R has a larger light-emitting area than the subpixel 110G. Thus, the shape and size of each subpixel can be determined independently. For example, the more reliable the light-emitting device, the smaller the size of the subpixel.
[0413] The Pentile arrangement is applied to the pixels 124a and 124b shown in Fig. 10(C). Fig. 10(C) shows an example in which the pixel 124a having the subpixel 110R and the subpixel 110G and the pixel 124b having the subpixel 110G and the subpixel 110B are arranged alternately.
[0414] 10(D) to 10(F) are arranged in a delta configuration. Pixel 124a has two subpixels (subpixel 110R and subpixel 110G) in the top row (first row) and one subpixel (subpixel 110B) in the bottom row (second row). Pixel 124b has one subpixel (subpixel 110B) in the top row (first row) and two subpixels (subpixel 110R and subpixel 110G) in the bottom row (second row).
[0415] Figure 10(D) is an example in which each sub-pixel has an approximately rectangular top surface shape with rounded corners, Figure 10(E) is an example in which each sub-pixel has a circular top surface shape, and Figure 10(F) is an example in which each sub-pixel has an approximately hexagonal top surface shape with rounded corners.
[0416] In Fig. 10(F), each subpixel is arranged inside a densely arranged hexagonal region. Each subpixel is arranged so that it is surrounded by six other subpixels when focusing on one subpixel. Furthermore, subpixels that emit light of the same color are arranged so that they are not adjacent to each other. For example, when focusing on subpixel 110R, three subpixels 110G and three subpixels 110B are arranged alternately to surround it.
[0417] 10G shows an example in which subpixels of each color are arranged in a zigzag pattern. Specifically, when viewed from above, the positions of the upper sides of two subpixels aligned in the row direction (for example, subpixels 110R and 110G, or subpixels 110G and 110B) are misaligned.
[0418] 10(A) to 10(G), it is preferable that the subpixel 110R be the subpixel R that emits red light, the subpixel 110G be the subpixel G that emits green light, and the subpixel 110B be the subpixel B that emits blue light. Note that the configuration of the subpixels is not limited to this, and the colors that the subpixels emit and their arrangement order can be determined appropriately. For example, the subpixel 110G may be the subpixel R that emits red light, and the subpixel 110R may be the subpixel G that emits green light.
[0419] In photolithography, the finer the pattern to be processed, the more significant the effect of light diffraction becomes. This impairs the fidelity of the photomask pattern when it is transferred by exposure, making it difficult to process the resist mask into the desired shape. Therefore, even if the photomask pattern is rectangular, a pattern with rounded corners is likely to be formed. As a result, the top surface shape of the subpixel may become a polygon with rounded corners, an ellipse, a circle, or the like.
[0420] Furthermore, in a method for manufacturing a light-emitting device according to one embodiment of the present invention, an organic compound layer is processed into an island shape using a resist mask. The resist film formed on the organic compound layer needs to be cured at a temperature lower than the heat resistance temperature of the organic compound layer. Therefore, depending on the heat resistance temperature of the material for the organic compound layer and the curing temperature of the resist material, the resist film may not be cured sufficiently. A resist film that is not cured sufficiently may have a shape that is different from the desired shape during processing. As a result, the top surface shape of the organic compound layer may be a polygon with rounded corners, an ellipse, a circle, or the like. For example, when a resist mask with a square top surface shape is formed, a resist mask with a circular top surface shape may be formed, resulting in a circular top surface shape of the organic compound layer.
[0421] In order to form the top surface of the organic compound layer into a desired shape, a technique for correcting the mask pattern in advance (OPC (Optical Proximity Correction) technique) may be used so that the design pattern and the transfer pattern coincide with each other. Specifically, in the OPC technique, a correction pattern is added to, for example, the corners of the figure on the mask pattern.
[0422] As shown in FIGS. 11A to 11I, a pixel can have four types of subpixels.
[0423] The pixels 178 shown in FIGS. 11(A) to 11(C) are arranged in a stripe pattern.
[0424] Figure 11(A) is an example in which each subpixel has a rectangular top surface shape, Figure 11(B) is an example in which each subpixel has a top surface shape that is a combination of two semicircles and a rectangle, and Figure 11(C) is an example in which each subpixel has an elliptical top surface shape.
[0425] The pixels 178 shown in FIGS. 11(D) to 11(F) are arranged in a matrix.
[0426] Figure 11(D) is an example in which each sub-pixel has a square top surface shape, Figure 11(E) is an example in which each sub-pixel has an approximately square top surface shape with rounded corners, and Figure 11(F) is an example in which each sub-pixel has a circular top surface shape.
[0427] 11(G) and 11(H) show an example in which one pixel 178 is configured in two rows and three columns.
[0428] 11(G) has three subpixels (subpixel 110R, subpixel 110G, and subpixel 110B) in the top row (first row) and one subpixel (subpixel 110W) in the bottom row (second row). In other words, pixel 178 has subpixel 110R in the left column (first column), subpixel 110G in the center column (second column), subpixel 110B in the right column (third column), and subpixel 110W across these three columns.
[0429] The pixel 178 shown in FIG. 11(H) has three subpixels (subpixels 110R, 110G, and 110B) in the top row (first row) and three subpixels 110W in the bottom row (second row). In other words, the pixel 178 has subpixels 110R and 110W in the left column (first column), subpixels 110G and 110W in the center column (second column), and subpixels 110B and 110W in the right column (third column). By aligning the subpixels in the top and bottom rows as shown in FIG. 11(H), it becomes possible to efficiently remove dust that may occur during the manufacturing process, for example. Therefore, a light-emitting device with high display quality can be provided.
[0430] In the pixel 178 shown in FIGS. 11(G) and 11(H), the subpixels 110R, 110G, and 110B are laid out in a stripe arrangement, which can improve the display quality.
[0431] FIG. 11(I) shows an example in which one pixel 178 is configured in three rows and two columns.
[0432] 11(I) has subpixel 110R in the top row (first row), subpixel 110G in the middle row (second row), subpixel 110B across the first and second rows, and one subpixel (subpixel 110W) in the bottom row (third row). In other words, pixel 178 has subpixel 110R and subpixel 110G in the left column (first column), subpixel 110B in the right column (second column), and subpixel 110W across these two columns.
[0433] In the pixel 178 shown in FIG. 11(I), the layout of the subpixels 110R, 110G, and 110B is a so-called S-stripe arrangement, which can improve the display quality.
[0434] 11A to 11I, the pixel 178 is composed of four subpixels: subpixel 110R, subpixel 110G, subpixel 110B, and subpixel 110W. For example, the subpixel 110R may be a subpixel that emits red light, the subpixel 110G may be a subpixel that emits green light, the subpixel 110B may be a subpixel that emits blue light, and the subpixel 110W may be a subpixel that emits white light. Note that at least one of the subpixels 110R, 110G, 110B, and 110W may be a subpixel that emits cyan light, a subpixel that emits magenta light, a subpixel that emits yellow light, or a subpixel that emits near-infrared light.
[0435] As described above, in the light-emitting device of one embodiment of the present invention, various layouts can be applied to pixels each including a subpixel having a light-emitting device.
[0436] This embodiment mode can be combined with other embodiment modes or examples as appropriate. In addition, in this specification, when multiple configuration examples are shown in one embodiment mode, the configuration examples can be combined as appropriate.
[0437] (Embodiment 5) In this embodiment, a display device according to one embodiment of the present invention will be described.
[0438] The display device of the present embodiment can be a high-definition display device, and can therefore be used as a display unit for information terminals (wearable devices) such as wristwatches and bracelets, as well as for wearable devices that can be worn on the head, such as VR devices such as head-mounted displays (HMDs) and AR devices such as glasses.
[0439] The display device of the present embodiment can be a high-resolution display device or a large-sized display device. Therefore, the display device of the present embodiment can be used in electronic devices with relatively large screens, such as television devices, desktop or notebook personal computers, computer monitors, digital signage, and large game machines such as pachinko machines, as well as in the display units of digital cameras, digital video cameras, digital photo frames, mobile phones, portable game machines, personal digital assistants, and sound reproduction devices.
[0440] [Display module] 12A shows a perspective view of a display module 280. The display module 280 includes a display device 100A and an FPC 290. Note that the display device included in the display module 280 is not limited to the display device 100A, and may be any of the display devices 100B to 100E2 described below.
[0441] The display module 280 has a substrate 291 and a substrate 292. The display module 280 has a display unit 281. The display unit 281 is an area that displays an image in the display module 280, and is an area where light from each pixel provided in a pixel unit 284 (described later) can be viewed.
[0442] 12(B) is a perspective view schematically showing the configuration on the substrate 291 side. A circuit portion 282, a pixel circuit portion 283 on the circuit portion 282, and a pixel portion 284 on the pixel circuit portion 283 are stacked on the substrate 291. A terminal portion 285 for connecting to an FPC 290 is provided in a portion of the substrate 291 that does not overlap with the pixel portion 284. The terminal portion 285 and the circuit portion 282 are electrically connected by a wiring portion 286 composed of a plurality of wirings.
[0443] The pixel section 284 has a plurality of periodically arranged pixels 284a. An enlarged view of one pixel 284a is shown on the right side of Fig. 12(B). The various configurations described in the previous embodiments can be applied to the pixel 284a.
[0444] The pixel circuit section 283 has a plurality of pixel circuits 283a arranged periodically.
[0445] One pixel circuit 283a is a circuit that controls the driving of a plurality of elements included in one pixel 284a.
[0446] The circuit portion 282 includes a circuit for driving each pixel circuit 283a of the pixel circuit portion 283. For example, it is preferable that the circuit portion 282 includes one or both of a gate line driver circuit and a source line driver circuit. In addition, the circuit portion 282 may include at least one of an arithmetic circuit, a memory circuit, a power supply circuit, etc.
[0447] The FPC 290 functions as wiring for supplying a video signal, a power supply potential, or the like from the outside to the circuit section 282. An IC may be mounted on the FPC 290.
[0448] The display module 280 can be configured such that one or both of the pixel circuit unit 283 and the circuit unit 282 are stacked below the pixel unit 284, thereby making it possible to extremely increase the aperture ratio (effective display area ratio) of the display unit 281.
[0449] Such a display module 280 has extremely high resolution and can therefore be suitably used in VR devices such as HMDs or glasses-type AR devices. For example, even in a configuration in which the display unit of the display module 280 is viewed through lenses, the display module 280 has an extremely high-resolution display unit 281, so that even if the display unit is enlarged with the lenses, the pixels are not visible, allowing for a highly immersive display. Furthermore, the display module 280 is not limited to this and can be suitably used in electronic devices having relatively small display units.
[0450] [Display device 100A] The display device 100A shown in FIG. 13A includes a substrate 301, a light emitting device 130R, a light emitting device 130G, a light emitting device 130B, a capacitor 240, and a transistor 310.
[0451] The substrate 301 corresponds to the substrate 291 in FIGS. 12A and 12B. The transistor 310 has a channel formation region in the substrate 301. The substrate 301 can be, for example, a semiconductor substrate such as a single crystal silicon substrate. The transistor 310 includes a part of the substrate 301, a conductive layer 311, a low-resistance region 312, an insulating layer 313, and an insulating layer 314. The conductive layer 311 functions as a gate electrode. The insulating layer 313 is located between the substrate 301 and the conductive layer 311 and functions as a gate insulating layer. The low-resistance region 312 is a region in which the substrate 301 is doped with impurities and functions as a source or drain. The insulating layer 314 is provided to cover a side surface of the conductive layer 311.
[0452] Furthermore, an element isolation layer 315 is provided between two adjacent transistors 310 so as to be embedded in the substrate 301 .
[0453] In addition, an insulating layer 261 is provided to cover the transistor 310 , and a capacitor 240 is provided on the insulating layer 261 .
[0454] Capacitor 240 has conductive layer 241, conductive layer 245, and insulating layer 243 located therebetween. Conductive layer 241 functions as one electrode of capacitor 240, conductive layer 245 functions as the other electrode of capacitor 240, and insulating layer 243 functions as a dielectric of capacitor 240.
[0455] The conductive layer 241 is provided over the insulating layer 261 and is buried in the insulating layer 254. The conductive layer 241 is electrically connected to one of the source and drain of the transistor 310 by a plug 271 buried in the insulating layer 261. The insulating layer 243 is provided to cover the conductive layer 241. The conductive layer 245 is provided in a region overlapping with the conductive layer 241 with the insulating layer 243 interposed therebetween.
[0456] An insulating layer 255 is provided covering the capacitor 240, an insulating layer 174 is provided on the insulating layer 255, and an insulating layer 175 is provided on the insulating layer 174. Light-emitting device 130R, light-emitting device 130G, and light-emitting device 130B are provided on the insulating layer 175. An insulator is provided in the region between adjacent light-emitting devices.
[0457] An insulating layer 156R is provided to have a region overlapping with a side surface of the conductive layer 151R, an insulating layer 156G is provided to have a region overlapping with a side surface of the conductive layer 151G, and an insulating layer 156B is provided to have a region overlapping with a side surface of the conductive layer 151B. Further, a conductive layer 152R is provided to cover the conductive layer 151R and the insulating layer 156R, a conductive layer 152G is provided to cover the conductive layer 151G and the insulating layer 156G, and a conductive layer 152B is provided to cover the conductive layer 151B and the insulating layer 156B. A sacrificial layer 158R is located on the organic compound layer 103R, a sacrificial layer 158G is located on the organic compound layer 103G, and a sacrificial layer 158B is located on the organic compound layer 103B.
[0458] The conductive layer 151R, the conductive layer 151G, and the conductive layer 151B are electrically connected to one of the source and drain of the transistor 310 via an insulating layer 243, an insulating layer 255, an insulating layer 174, a plug 256 embedded in the insulating layer 175, a conductive layer 241 embedded in the insulating layer 254, and a plug 271 embedded in the insulating layer 261. Various conductive materials can be used for the plug.
[0459] Furthermore, a protective layer 131 is provided on the light-emitting devices 130R, 130G, and 130B. A substrate 120 is bonded to the protective layer 131 with a resin layer 122. For details of the components from the light-emitting devices 130 to the substrate 120, refer to Embodiment 2. The substrate 120 corresponds to the substrate 292 in FIG. 12(A).
[0460] Fig. 13(B) is a modified example of the display device 100A shown in Fig. 13(A). The display device shown in Fig. 13(B) has a colored layer 132R, a colored layer 132G, and a colored layer 132B, and the light-emitting device 130 has an area where it overlaps with one of the colored layer 132R, the colored layer 132G, and the colored layer 132B. In the display device shown in Fig. 13(B), the light-emitting device 130 can emit, for example, white light. Furthermore, for example, the colored layer 132R can transmit red light, the colored layer 132G can transmit green light, and the colored layer 132B can transmit blue light.
[0461] [Display device 100B] FIG. 14 shows a perspective view of the display device 100B.
[0462] The display device 100B has a configuration in which a substrate 352 and a substrate 351 are bonded together. In Fig. 14, the substrate 352 is indicated by a dashed line.
[0463] The display device 100B has a pixel unit 177, a connection unit 140, a circuit 356, wiring 355, etc. Fig. 14 shows an example in which an IC 354 and an FPC 353 are mounted on the display device 100B. Therefore, the configuration shown in Fig. 14 can also be called a display module having the display device 100B, an IC (integrated circuit), and an FPC. Here, a display device having a connector such as an FPC attached to a substrate, or a display device having an IC mounted on the substrate, is called a display module.
[0464] The connection section 140 is provided outside the pixel section 177. There may be one or more connection sections 140. The connection section 140 electrically connects the common electrode of the light-emitting device and the conductive layer, and can supply a potential to the common electrode.
[0465] The circuit 356 can be, for example, a scanning line driver circuit.
[0466] The wiring 355 has a function of supplying signals and power to the pixel portion 177 and the circuit 356. The signals and power are input to the wiring 355 from the outside via the FPC 353 or from the IC 354.
[0467] 14 shows an example in which an IC 354 is provided on a substrate 351 by a COG (Chip On Glass) method or a COF (Chip on Film) method. The IC 354 may be, for example, an IC having a scanning line driver circuit or a signal line driver circuit. The display device 100B and the display module may not include an IC. Alternatively, the IC may be mounted on an FPC by a COF method, for example.
[0468] Figure 15 shows an example of a cross section of display device 100B in Figure 14, where part of the area including FPC 353, part of circuit 356, part of pixel section 177, part of connection section 140, and part of the area including the end portion are cut away, as display device 100C.
[0469] [Display device 100C] The display device 100C shown in Figure 15 has, between substrate 351 and substrate 352, transistor 201, transistor 205, light-emitting device 130R that emits red light, light-emitting device 130G that emits green light, and light-emitting device 130B that emits blue light, etc.
[0470] For details of the light emitting devices 130R, 130G, and 130B, refer to the third embodiment.
[0471] Light-emitting device 130R has conductive layer 224R, conductive layer 151R on conductive layer 224R, and conductive layer 152R on conductive layer 151R. Light-emitting device 130G has conductive layer 224G, conductive layer 151G on conductive layer 224G, and conductive layer 152G on conductive layer 151G. Light-emitting device 130B has conductive layer 224B, conductive layer 151B on conductive layer 224B, and conductive layer 152B on conductive layer 151B.
[0472] The conductive layer 224R is connected to the conductive layer 222b of the transistor 205 through an opening provided in the insulating layer 214. An end of the conductive layer 151R is located outside an end of the conductive layer 224R. An insulating layer 156R is provided to have a region in contact with a side surface of the conductive layer 151R, and a conductive layer 152R is provided to cover the conductive layer 151R and the insulating layer 156R.
[0473] Conductive layer 224G, conductive layer 151G, conductive layer 152G, and insulating layer 156G in light-emitting device 130G, and conductive layer 224B, conductive layer 151B, conductive layer 152B, and insulating layer 156B in light-emitting device 130B are similar to conductive layer 224R, conductive layer 151R, conductive layer 152R, and insulating layer 156R in light-emitting device 130R, and therefore detailed description thereof will be omitted.
[0474] Recesses are formed in conductive layers 224R, 224G, and 224B so as to cover the openings provided in insulating layer 214. Layer 128 is buried in the recesses.
[0475] Layer 128 has the function of filling in recesses in conductive layer 224R, conductive layer 224G, and conductive layer 224B and flattening the surface. Conductive layers 151R, 151G, and 151B, which are electrically connected to conductive layer 224R, conductive layer 224G, and conductive layer 224B, are provided on conductive layer 224R, conductive layer 224G, and conductive layer 224B and layer 128. Therefore, the regions overlapping with the recesses in conductive layer 224R, conductive layer 224G, and conductive layer 224B can also be used as light-emitting regions, thereby increasing the aperture ratio of the pixel.
[0476] The layer 128 may be an insulating layer or a conductive layer. Various inorganic insulating materials, organic insulating materials, and conductive materials can be used for the layer 128 as appropriate. In particular, the layer 128 is preferably formed using an insulating material, and is particularly preferably formed using an organic insulating material. For example, the organic insulating materials that can be used for the insulating layer 127 described above can be used for the layer 128.
[0477] A protective layer 131 is provided on the light-emitting device 130R, the light-emitting device 130G, and the light-emitting device 130B. The protective layer 131 and the substrate 352 are bonded via an adhesive layer 142. A light-shielding layer 157 is provided on the substrate 352. A solid sealing structure, a hollow sealing structure, or the like can be applied to seal the light-emitting device 130. In FIG. 15, the space between the substrate 352 and the substrate 351 is filled with the adhesive layer 142, and a solid sealing structure is applied. Alternatively, the space may be filled with an inert gas (nitrogen, argon, etc.), and a hollow sealing structure may be applied. In this case, the adhesive layer 142 may be provided so as not to overlap with the light-emitting device. Alternatively, the space may be filled with a resin different from the frame-shaped adhesive layer 142.
[0478] 15 shows an example in which connecting portion 140 has conductive layer 224C obtained by processing the same conductive film as conductive layers 224R, 224G, and 224B, conductive layer 151C obtained by processing the same conductive film as conductive layers 151R, 151G, and 151B, and conductive layer 152C obtained by processing the same conductive film as conductive layers 152R, 152G, and 152B. Also shown in FIG. 15 is an example in which insulating layer 156C is provided so as to have a region overlapping with a side surface of conductive layer 151C.
[0479] The display device 100C is a top-emission type. Light emitted by the light-emitting device is emitted toward the substrate 352. The substrate 352 is preferably made of a material that is highly transparent to visible light. The pixel electrodes contain a material that reflects visible light, and the counter electrode (common electrode 155) contains a material that transmits visible light.
[0480] An insulating layer 211, an insulating layer 213, an insulating layer 215, and an insulating layer 214 are provided in this order over the substrate 351. A part of the insulating layer 211 functions as a gate insulating layer for each transistor. A part of the insulating layer 213 functions as a gate insulating layer for each transistor. The insulating layer 215 is provided to cover the transistor. The insulating layer 214 is provided to cover the transistor and functions as a planarization layer. Note that the number of gate insulating layers and the number of insulating layers covering the transistors are not limited, and each may be a single layer or two or more layers.
[0481] The insulating layers 211, 213, and 215 are each preferably made of an inorganic insulating film.
[0482] The insulating layer 214, which functions as a planarizing layer, is preferably an organic insulating layer.
[0483] The transistor 201 and the transistor 205 each include a conductive layer 221 functioning as a gate, an insulating layer 211 functioning as a gate insulating layer, a conductive layer 222a and a conductive layer 222b functioning as a source and a drain, a semiconductor layer 231, an insulating layer 213 functioning as a gate insulating layer, and a conductive layer 223 functioning as a gate.
[0484] A connection portion 204 is provided in a region of the substrate 351 where the substrate 352 does not overlap. In the connection portion 204, the source electrode or drain electrode of the transistor 201 is electrically connected to the FPC 353 via a conductive layer 166 and a connection layer 242. The conductive layer 166 has an example of a laminated structure including a conductive film obtained by processing the same conductive film as the conductive layers 224R, 224G, and 224B, a conductive film obtained by processing the same conductive film as the conductive layers 151R, 151G, and 151B, and a conductive film obtained by processing the same conductive film as the conductive layers 152R, 152G, and 152B. The conductive layer 166 is exposed on the top surface of the connection portion 204. This allows the connection portion 204 and the FPC 353 to be electrically connected via the connection layer 242.
[0485] It is preferable to provide a light-shielding layer 157 on the surface of substrate 352 facing substrate 351. Light-shielding layer 157 can be provided between adjacent light-emitting devices, on connecting portions 140, on circuits 356, etc. Various optical members can be arranged on the outside of substrate 352.
[0486] The materials that can be used for the substrate 120 can be used for the substrate 351 and the substrate 352, respectively.
[0487] The adhesive layer 142 can be made of a material that can be used for the resin layer 122 .
[0488] The connection layer 242 may be an anisotropic conductive film (ACF), an anisotropic conductive paste (ACP), or the like.
[0489] [Display device 100D] The display device 100D shown in FIG. 16 differs from the display device 100C shown in FIG. 15 mainly in that it is a bottom-emission display device.
[0490] Light emitted from the light emitting device is emitted toward the substrate 351. It is preferable that a material with high transparency to visible light is used for the substrate 351. On the other hand, the light transparency of the material used for the substrate 352 is not an issue.
[0491] A light-shielding layer 317 is preferably formed between the substrate 351 and the transistor 201 and between the substrate 351 and the transistor 205. Figure 16 shows an example in which the light-shielding layer 317 is provided over the substrate 351, the insulating layer 153 is provided over the light-shielding layer 317, and the transistors 201, 205, etc. are provided over the insulating layer 153.
[0492] Light emitting device 130R includes conductive layer 112R, conductive layer 126R on conductive layer 112R, and conductive layer 129R on conductive layer 126R.
[0493] Light emitting device 130B includes conductive layer 112B, conductive layer 126B on conductive layer 112B, and conductive layer 129B on conductive layer 126B.
[0494] The conductive layers 112R, 112B, 126R, 126B, 129R, and 129B are each made of a material that is highly transparent to visible light. The second electrode 102 is preferably made of a material that reflects visible light.
[0495] Although the light emitting device 130G is not shown in FIG. 16, the light emitting device 130G is also provided.
[0496] In addition, although FIG. 16 and other figures show an example in which the top surface of the layer 128 has a flat portion, the shape of the layer 128 is not particularly limited.
[0497] [Display device 100D2] The display device 100D2 shown in Fig. 17(A) is an example of a bottom-emission type display device that differs from the display device 100D shown in Fig. 16. The display device 100D2 differs from the display device 100D in that it has an organic resin layer 180. Note that in the drawing, the reference numerals of the same components as those in Fig. 16 may be omitted, and the description in Fig. 16 can be referred to for details.
[0498] 17(B) shows a top view layout of pixel 178 (pixel 178a and pixel 178b) having subpixels 110 (subpixels 110R, 110G, 110B, and 110W), and FIG. 17(C) shows a top view of organic resin layer 180 in a region where subpixels 110R and 110G of pixel 178 are formed. The width between light-shielding layers 317 is width 110Rw in the light-emitting region of subpixel 110R.
[0499] As shown in FIG. 17(A), the organic resin layer 180 is provided on the insulating layer 214. As shown in the region surrounded by the dashed line in FIG. 17(A) and in FIG. 17(C), the organic resin layer 180 has curved recesses 181 (recesses 181a and 181b) at least in the region where the subpixels are formed. The recesses 181 may be provided outside the light-emitting region, such as recess 181c. By providing recess 181c, light emitted in the region overlapping with the light-shielding layer 317 or light traveling to the region overlapping with the light-shielding layer 317 is refracted and can be extracted from the light-emitting region, thereby improving the light-emitting efficiency.
[0500] A plurality of recesses 181 may be formed in a matrix. Recesses 181a and 181b may be provided in contact with each other, or may have a flat surface between them.
[0501] 17, the recess has a hexagonal top surface shape (FIG. 17(C)) and a semicircular cross-sectional shape (FIG. 17(A)), but other shapes may be used as needed. For example, the recess may have a polygonal top surface shape such as a triangle, a quadrangle (including a rectangle and a square), a pentagon, or any of these polygons with rounded corners, an ellipse, or a circle.
[0502] An insulating layer containing an organic material can be used as the organic resin layer 180. For example, acrylic resin, polyimide resin, epoxy resin, imide resin, polyamide resin, polyimideamide resin, silicone resin, siloxane resin, benzocyclobutene resin, phenol resin, precursors of these resins, etc. can be used as the organic resin layer 180. Alternatively, organic materials such as polyvinyl alcohol (PVA), polyvinyl butyral, polyvinylpyrrolidone, polyethylene glycol, polyglycerin, pullulan, water-soluble cellulose, or alcohol-soluble polyamide resin can be used as the organic resin layer 180.
[0503] Furthermore, a photosensitive resin can be used as the organic resin layer 180. A photoresist can be used as the photosensitive resin. The photosensitive resin can be a positive type material or a negative type material.
[0504] The organic resin layer 180 may contain a material that absorbs visible light. For example, the organic resin layer 180 itself may be made of a material that absorbs visible light, or the organic resin layer 180 may contain a pigment that absorbs visible light. For example, the organic resin layer 180 may be made of a resin that can be used as a color filter that transmits red, blue, or green light and absorbs other light, or a resin that contains carbon black as a pigment and functions as a black matrix.
[0505] In addition, a first electrode 101 (a first electrode 101R and a first electrode 101W) is provided on the organic resin layer 180, and an organic compound layer 103 is provided on the first electrode 101. Ends of the first electrode 101 and the organic compound layer 103 may be covered with an insulating layer 127.
[0506] Furthermore, the first electrode 101 formed on the organic resin layer 180 has a recess similar to the recess of the organic resin layer 180. Furthermore, the organic compound layer 103 formed on the first electrode 101 has a recess similar to the recess of the first electrode 101. Furthermore, the common layer 104 formed on the organic compound layer 103 has a recess similar to the recess of the organic compound layer 103. Furthermore, the second electrode 102 formed on the common layer 104 has a recess similar to the recess of the common layer 104. That is, the recesses of the organic resin layer 180, the first electrode 101, the organic compound layer 103, the common layer 104, and the second electrode 102 have a structure in which they overlap one another.
[0507] In addition, a common layer 104 is provided over the organic compound layer 103 and the insulating layer 127, and a second electrode 102 is provided over the common layer 104. A protective layer 131 is provided over the second electrode 102, and the second electrode 102 is bonded to a substrate 352 via an adhesive layer 142.
[0508] Although the light emitting device 130G and the light emitting device 130B are not shown in FIG. 17(A), the light emitting device 130G and the light emitting device 130B are also provided.
[0509] [Display device 100E] The display device 100E shown in FIG. 18 is a modification of the display device 100C shown in FIG. 15, and differs from the display device 100C mainly in that it has colored layers 132R, 132G, and 132B.
[0510] In the display device 100E, the light-emitting device 130 has an area that overlaps one of the colored layer 132R, the colored layer 132G, and the colored layer 132B. The colored layer 132R, the colored layer 132G, and the colored layer 132B can be provided on the surface of the substrate 352 facing the substrate 351. An end of the colored layer 132R, an end of the colored layer 132G, and an end of the colored layer 132B can overlap the light-shielding layer 157.
[0511] In the display device 100E, the light-emitting device 130 can emit, for example, white light. Furthermore, for example, the colored layer 132R can transmit red light, the colored layer 132G can transmit green light, and the colored layer 132B can transmit blue light. The display device 100E may be configured such that the colored layers 132R, 132G, and 132B are provided between the protective layer 131 and the adhesive layer 142.
[0512] [Display device 100E2] The display device 100E2 shown in Fig. 19(A) is a modified example of the display device 100E shown in Fig. 18, and has microlenses 182 on the colored layers 132R, 132G, and 132B. Note that in the figure, the reference numerals of the same components as those in Fig. 18 may be omitted, and the description in Fig. 18 can be referred to for details.
[0513] 19(B) shows a top view layout of a pixel 178 (pixel 178a and pixel 178b) having subpixels 110 (subpixels 110R, 110G, and 110B), and FIG. 19(C) shows a top view of a microlens 182 in a region where the subpixels 110R and 110G of the pixel 178 are formed. The width of the region where the common electrode 155 and the organic compound layer 103 are in contact is width 110Gw in the light-emitting region of the subpixel 110G.
[0514] 19(A) has a planarization film 143 provided on a protective layer 131, and colored layers 132R, 132G, and 132B provided on the planarization film 143. A planarization film 144 is provided so as to cover the colored layers 132R, 132G, and 132B. A microlens 182 is provided on the planarization film 144.
[0515] As shown in FIG. 19C, the microlens 182 may be provided for each sub-pixel in a region where the sub-pixel is formed.
[0516] 19(C), the top surface shape of the microlens 182 is shown as a hexagon, but other shapes may be used as needed. For example, the top surface shape of the microlens 182 may be a polygon such as a triangle, a quadrangle (including a rectangle and a square), a pentagon, or any other polygon with rounded corners, an ellipse, or a circle.
[0517] The microlenses 182 can be formed using the same material as the organic resin layer 180 .
[0518] This embodiment mode can be combined with other embodiment modes or examples as appropriate. In addition, in this specification, when multiple configuration examples are shown in one embodiment mode, the configuration examples can be combined as appropriate.
[0519] (Embodiment 6) In this embodiment, an electronic device according to one embodiment of the present invention will be described.
[0520] The electronic devices of this embodiment include the light-emitting device of one embodiment of the present invention in their display portions. The light-emitting device of one embodiment of the present invention is highly reliable and can easily achieve high definition and high resolution. Therefore, the light-emitting device can be used in the display portions of various electronic devices.
[0521] Examples of electronic devices include electronic devices with relatively large screens such as television sets, desktop or notebook personal computers, computer monitors, digital signage, large game machines such as pachinko machines, as well as digital cameras, digital video cameras, digital photo frames, mobile phones, portable game machines, personal digital assistants, and sound playback devices.
[0522] In particular, the light-emitting device of one embodiment of the present invention can have high resolution and can therefore be suitably used in electronic devices having a relatively small display portion. Examples of such electronic devices include wristwatch-type and bracelet-type information terminals (wearable devices), and head-mounted wearable devices such as VR devices such as head-mounted displays, AR glasses-type devices, and MR (Mixed Reality) devices.
[0523] The light-emitting device of one embodiment of the present invention preferably has an extremely high resolution such as HD (1280 × 720 pixels), FHD (1920 × 1080 pixels), WQHD (2560 × 1440 pixels), WQXGA (2560 × 1600 pixels), 4K (3840 × 2160 pixels), or 8K (7680 × 4320 pixels). A resolution of 4K, 8K, or higher is particularly preferable. Furthermore, the pixel density (resolution) of the light-emitting device of one embodiment of the present invention is preferably 100 ppi or higher, more preferably 300 ppi or higher, more preferably 500 ppi or higher, more preferably 1000 ppi or higher, more preferably 2000 ppi or higher, more preferably 3000 ppi or higher, more preferably 5000 ppi or higher, and even more preferably 7000 ppi or higher. By using a light-emitting device having either or both of high resolution and high definition, it is possible to further enhance the sense of realism and depth. Furthermore, the screen ratio (aspect ratio) of the light-emitting device according to one embodiment of the present invention is not particularly limited. For example, the light-emitting device can accommodate various screen ratios such as 1:1 (square), 4:3, 16:9, and 16:10.
[0524] The electronic device of this embodiment may have a sensor (including a function to measure force, displacement, position, velocity, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays).
[0525] The electronic device of the present embodiment can have various functions, such as a function to display various information (still images, videos, text images, etc.) on a display unit, a touch panel function, a function to display a calendar, date, time, etc., a function to execute various software (programs), a wireless communication function, a function to read out programs or data recorded on a recording medium, etc.
[0526] 20(A) to 20(D), an example of a wearable device that can be worn on the head will be described. These wearable devices have at least one of the following functions: a function to display AR content, a function to display VR content, a function to display SR (Substitutional Reality) content, and a function to display MR content. By having an electronic device have the function to display at least one of AR, VR, SR, and MR content, it is possible to enhance the user's sense of immersion.
[0527] The electronic device 700A shown in Figure 20(A) and the electronic device 700B shown in Figure 20(B) each have a pair of display panels 751, a pair of housings 721, a communication unit (not shown), a pair of mounting units 723, a control unit (not shown), an imaging unit (not shown), a pair of optical members 753, a frame 757, and a pair of nose pads 758.
[0528] The light-emitting device of one embodiment of the present invention can be applied to the display panel 751. Therefore, the electronic device can be highly reliable.
[0529] Electronic device 700A and electronic device 700B can each project an image displayed on display panel 751 onto display area 756 of optical member 753. Because optical member 753 is translucent, the user can see the image displayed in the display area superimposed on a transmitted image visually recognized through optical member 753. Therefore, electronic device 700A and electronic device 700B are each electronic devices capable of AR display.
[0530] Electronic device 700A and electronic device 700B may be provided with a camera capable of capturing an image in front of them as an imaging unit. Furthermore, electronic device 700A and electronic device 700B may each be provided with an acceleration sensor such as a gyro sensor, thereby detecting the orientation of the user's head and displaying an image corresponding to that orientation in display area 756.
[0531] The communication unit has a wireless communication device, and can supply, for example, a video signal via the wireless communication device. Note that instead of or in addition to the wireless communication device, a connector to which a cable through which a video signal and a power supply potential can be connected may be provided.
[0532] Furthermore, the electronic device 700A and the electronic device 700B are provided with batteries, which can be charged wirelessly and / or by wire.
[0533] The housing 721 may be provided with a touch sensor module. The touch sensor module has a function of detecting a touch on the outer surface of the housing 721. The touch sensor module detects a tap operation, a slide operation, or the like by the user, and can execute various processes. For example, a tap operation can execute processes such as pausing or resuming a video, and a slide operation can execute processes such as fast-forwarding or fast-rewinding. Furthermore, providing a touch sensor module on each of the two housings 721 can broaden the range of operations.
[0534] Various touch sensors can be used as the touch sensor module. For example, various types of touch sensors can be used, such as a capacitance type, a resistive film type, an infrared type, an electromagnetic induction type, a surface acoustic wave type, or an optical type. In particular, it is preferable to use a capacitance type or an optical type sensor in the touch sensor module.
[0535] When an optical touch sensor is used, a photoelectric conversion device (also called a photoelectric conversion element) can be used as the light receiving element. The active layer of the photoelectric conversion device can be made of either or both of an inorganic semiconductor and an organic semiconductor.
[0536] The electronic device 800A shown in Figure 20(C) and the electronic device 800B shown in Figure 20(D) each have a pair of display units 820, a housing 821, a communication unit 822, a pair of mounting units 823, a control unit 824, a pair of imaging units 825, and a pair of lenses 832.
[0537] The light-emitting device of one embodiment of the present invention can be applied to the display portion 820. Therefore, the electronic device can be highly reliable.
[0538] Display unit 820 is provided inside housing 821 at a position that can be viewed through lens 832. Also, by displaying different images on the pair of display units 820, it is possible to perform a three-dimensional display using parallax.
[0539] Electronic device 800A and electronic device 800B can each be said to be electronic devices for VR. A user wearing electronic device 800A or electronic device 800B can view an image displayed on display unit 820 through lens 832.
[0540] It is preferable that electronic device 800A and electronic device 800B each have a mechanism that can adjust the left and right positions of lens 832 and display unit 820 so that they are optimally positioned according to the position of the user's eyes. It is also preferable that electronic device 800A and electronic device 800B each have a mechanism that can adjust the focus by changing the distance between lens 832 and display unit 820.
[0541] The user can wear the electronic device 800A or the electronic device 800B on the head by using the wearing unit 823. Note that, for example, in Fig. 20(C), the wearing unit 823 is shaped like the temples of glasses (also called temples, etc.), but is not limited to this. The wearing unit 823 may be shaped like a helmet or a band, for example, as long as it can be worn by the user.
[0542] The imaging unit 825 has a function of acquiring external information. Data acquired by the imaging unit 825 can be output to the display unit 820. An image sensor can be used for the imaging unit 825. Furthermore, multiple cameras may be provided to support multiple angles of view, such as telephoto and wide angle.
[0543] Although an example having the imaging unit 825 has been shown here, a distance measuring sensor (hereinafter also referred to as a detection unit) capable of measuring the distance to an object may be provided. That is, the imaging unit 825 is one aspect of the detection unit. As the detection unit, for example, an image sensor or a range image sensor such as a LiDAR (Light Detection and Ranging) can be used. By using an image obtained by the camera and an image obtained by the range image sensor, more information can be obtained, enabling more accurate gesture operations.
[0544] Electronic device 800A may have a vibration mechanism that functions as a bone conduction earphone. For example, a configuration having such a vibration mechanism can be applied to one or more of display unit 820, housing 821, and wearing unit 823. This allows a user to enjoy video and audio simply by wearing electronic device 800A, without the need for separate audio equipment such as headphones, earphones, or speakers.
[0545] The electronic device 800A and the electronic device 800B may each have an input terminal to which a cable can be connected for supplying a video signal from a video output device or the like and power for charging a battery provided in the electronic device.
[0546] The electronic device of one embodiment of the present invention may have a function of wireless communication with an earphone 750. The earphone 750 has a communication unit (not shown) and has a wireless communication function. The earphone 750 can receive information (e.g., audio data) from the electronic device through the wireless communication function. For example, the electronic device 700A shown in FIG. 20A has a function of transmitting information to the earphone 750 through the wireless communication function. Furthermore, for example, the electronic device 800A shown in FIG. 20C has a function of transmitting information to the earphone 750 through the wireless communication function.
[0547] The electronic device may also have an earphone unit. Electronic device 700B shown in Fig. 20(B) has earphone unit 727. For example, earphone unit 727 and a control unit may be configured to be connected to each other by wire. Part of the wiring connecting earphone unit 727 and the control unit may be disposed inside housing 721 or wearing unit 723.
[0548] Similarly, electronic device 800B shown in Fig. 20(D) has earphone unit 827. For example, earphone unit 827 and control unit 824 can be configured to be connected to each other by wire. Part of the wiring connecting earphone unit 827 and control unit 824 may be disposed inside housing 821 or wearing unit 823. Furthermore, earphone unit 827 and wearing unit 823 may have magnets. This allows earphone unit 827 to be fixed to wearing unit 823 by magnetic force, which is preferable as it makes storage easier.
[0549] The electronic device may have an audio output terminal to which earphones or headphones can be connected. The electronic device may also have one or both of an audio input terminal and an audio input mechanism. For example, a sound collection device such as a microphone can be used as the audio input mechanism. By having the audio input mechanism, the electronic device may be endowed with the functionality of a so-called headset.
[0550] As described above, the electronic devices of one embodiment of the present invention are preferably either glasses-type devices (such as the electronic devices 700A and 700B) or goggle-type devices (such as the electronic devices 800A and 800B).
[0551] Furthermore, the electronic device according to one embodiment of the present invention can transmit information to the earphone via a wired or wireless connection.
[0552] An electronic device 6500 shown in FIG. 21A is a portable information terminal that can be used as a smartphone.
[0553] The electronic device 6500 includes a housing 6501, a display portion 6502, a power button 6503, a button 6504, a speaker 6505, a microphone 6506, a camera 6507, and a light source 6508. The display portion 6502 has a touch panel function.
[0554] The light-emitting device of one embodiment of the present invention can be applied to the display portion 6502. Therefore, the electronic device can be highly reliable.
[0555] FIG. 21B is a schematic cross-sectional view including the end portion of the housing 6501 on the microphone 6506 side.
[0556] A light-transmitting protective member 6510 is provided on the display surface side of the housing 6501, and a display panel 6511, optical members 6512, a touch sensor panel 6513, a printed circuit board 6517, a battery 6518, etc. are arranged in the space surrounded by the housing 6501 and the protective member 6510.
[0557] A display panel 6511, an optical member 6512, and a touch sensor panel 6513 are fixed to the protective member 6510 by adhesive layers (not shown).
[0558] In an area outside the display unit 6502, a part of the display panel 6511 is folded back, and an FPC 6515 is connected to the folded back part. An IC 6516 is mounted on the FPC 6515. The FPC 6515 is connected to a terminal provided on a printed circuit board 6517.
[0559] The light-emitting device of one embodiment of the present invention can be applied to the display panel 6511. Therefore, an extremely lightweight electronic device can be realized. Furthermore, since the display panel 6511 is extremely thin, a large-capacity battery 6518 can be mounted thereon while keeping the thickness of the electronic device small. Furthermore, by folding back a part of the display panel 6511 and arranging a connection portion with the FPC 6515 on the back side of the pixel portion, an electronic device with a narrow frame can be realized.
[0560] 21C shows an example of a television set. A television set 7100 includes a display portion 7000 built in a housing 7171. Here, the housing 7171 is supported by a stand 7173.
[0561] The light-emitting device of one embodiment of the present invention can be applied to the display portion 7000. Therefore, the electronic device can have high reliability.
[0562] 21C can be operated using operation switches provided on the housing 7171 and a separate remote control 7151. Alternatively, the display portion 7000 may be provided with a touch sensor, and the television set 7100 may be operated by touching the display portion 7000 with a finger or the like. The remote control 7151 may have a display portion that displays information output from the remote control 7151. Channels and volume can be controlled by operation keys or a touch panel provided on the remote control 7151, and an image displayed on the display portion 7000 can be controlled.
[0563] The television device 7100 is configured to include a receiver, a modem, and the like. The receiver can receive general television broadcasts. In addition, by connecting to a wired or wireless communication network via the modem, it is possible to perform one-way (from sender to receiver) or two-way (between sender and receiver, or between receivers, etc.) information communication.
[0564] 21D shows an example of a laptop personal computer 7200. The laptop personal computer 7200 includes a housing 7211, a keyboard 7212, a pointing device 7213, and an external connection port 7214. A display portion 7000 is incorporated in the housing 7211.
[0565] The light-emitting device of one embodiment of the present invention can be applied to the display portion 7000. Therefore, the electronic device can have high reliability.
[0566] 21(E) and 21(F) show an example of digital signage.
[0567] 21E includes a housing 7301, a display portion 7000, and a speaker 7303. The digital signage 7300 may further include an LED lamp, operation keys (including a power switch or an operation switch), a connection terminal, various sensors, a microphone, and the like.
[0568] 21F shows a digital signage 7400 attached to a cylindrical pillar 7401. The digital signage 7400 has a display unit 7000 provided along the curved surface of the pillar 7401.
[0569] 21E and 21F, the light-emitting device of one embodiment of the present invention can be applied to the display portion 7000. Therefore, the electronic device can have high reliability.
[0570] The larger the display unit 7000, the more information can be provided at one time. Also, the larger the display unit 7000, the more easily it will attract people's attention, which can increase the advertising effectiveness of, for example, advertisements.
[0571] Applying a touch panel to the display unit 7000 is preferable because it not only displays images or videos on the display unit 7000 but also allows the user to intuitively operate it. Furthermore, when used to provide information such as route information or traffic information, usability can be improved through intuitive operation.
[0572] 21(E) and 21(F), the digital signage 7300 or the digital signage 7400 is preferably capable of wirelessly linking with an information terminal 7311 or an information terminal 7411 such as a smartphone carried by a user. For example, advertising information displayed on the display unit 7000 can be displayed on the screen of the information terminal 7311 or the information terminal 7411. By operating the information terminal 7311 or the information terminal 7411, the display on the display unit 7000 can be switched.
[0573] Furthermore, the digital signage 7300 or the digital signage 7400 can be made to run a game using the screen of the information terminal 7311 or the information terminal 7411 as an operation means (controller), thereby allowing an unspecified number of users to simultaneously participate in and enjoy the game.
[0574] The electronic devices shown in Figures 22(A) to 22(G) have a housing 9000, a display portion 9001, a speaker 9003, operation keys 9005 (including a power switch or an operation switch), a connection terminal 9006, a sensor 9007 (including a function to measure force, displacement, position, speed, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, odor or infrared rays), a microphone 9008, etc.
[0575] 22(A) to 22(G) have various functions. For example, they may have a function of displaying various information (still images, videos, text images, etc.) on a display unit, a touch panel function, a function of displaying a calendar, date, time, etc., a function of controlling processing using various software (programs), a wireless communication function, a function of reading and processing programs or data recorded on a recording medium, etc. Note that the functions of the electronic devices are not limited to these, and they may have various other functions. The electronic devices may have multiple display units. Furthermore, the electronic devices may have a function of providing a camera or the like to capture still images or videos and store them in a recording medium (external or built-in to the camera), a function of displaying the captured images on the display unit, etc.
[0576] The electronic devices shown in FIGS. 22A to 22G will be described in detail below.
[0577] FIG. 22A is a perspective view showing a mobile information terminal 9171. The mobile information terminal 9171 can be used as, for example, a smartphone. Note that the mobile information terminal 9171 may be provided with a speaker 9003, a connection terminal 9006, a sensor 9007, or the like. The mobile information terminal 9171 can display text and image information on multiple surfaces thereof. FIG. 22A shows an example in which three icons 9050 are displayed. Information 9051 indicated by a dashed rectangle can also be displayed on another surface of the display unit 9001. Examples of the information 9051 include notification of an incoming email, SNS, phone call, etc., the title of the email or SNS, the sender's name, the date and time, the remaining battery level, and radio wave intensity. Alternatively, the icon 9050 or the like may be displayed in the position where the information 9051 is displayed.
[0578] 22B is a perspective view showing a mobile information terminal 9172. The mobile information terminal 9172 has a function of displaying information on three or more surfaces of the display portion 9001. Here, an example is shown in which information 9052, information 9053, and information 9054 are displayed on different surfaces. For example, a user can check information 9053 displayed in a position that can be observed from above the mobile information terminal 9172 while storing the mobile information terminal 9172 in a breast pocket of clothes. The user can check the display without taking the mobile information terminal 9172 out of the pocket and decide, for example, whether to answer a call.
[0579] 22C is a perspective view of a tablet terminal 9173. The tablet terminal 9173 is capable of executing various applications such as mobile phone calls, e-mails, document browsing and creation, music playback, internet communication, and computer games. The tablet terminal 9173 has a display portion 9001, a camera 9002, a microphone 9008, and a speaker 9003 on the front side of a housing 9000, operation keys 9005 as operation buttons on the left side of the housing 9000, and a connection terminal 9006 on the bottom.
[0580] 22D is a perspective view showing a wristwatch-type mobile information terminal 9200. The mobile information terminal 9200 can be used as, for example, a smart watch (registered trademark). The display surface of the display portion 9001 is curved, and display can be performed along the curved display surface. The m...
Claims
1. having a first heteroaromatic ring, a second heteroaromatic ring, and a pyridine ring; the first heteroaromatic ring is a benzo[h]quinazoline skeleton, the second heteroaromatic ring is a substituted or unsubstituted heteroaromatic ring having 8 to 40 carbon atoms, and is different from the first heteroaromatic ring in that the 2-position of the benzo[h]quinazoline skeleton is bonded to the 2-position of the pyridine ring; an organic compound in which the second heteroaromatic ring is bonded to any one of the 3- to 6-positions of the pyridine ring;
2. having a first heteroaromatic ring, a second heteroaromatic ring, and a pyridine ring; the first heteroaromatic ring is a benzo[h]quinazoline skeleton, the second heteroaromatic ring is a substituted or unsubstituted heteroaromatic ring having 8 to 40 carbon atoms, and is different from the first heteroaromatic ring in that the 2-position of the benzo[h]quinazoline skeleton is bonded to the 2-position of the pyridine ring; an organic compound in which the second heteroaromatic ring is bonded to any one of the 3- to 6-positions of the pyridine ring via an arylene group;
3. An organic compound represented by general formula (G1-1) (excluding organic compounds represented by general formula (N1)). 【Chemistry 1】 (In general formula (G1-1), Ar 1 represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, n1 represents an integer of 1 to 3, R 1 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, the heteroaromatic ring being bonded to the arylene group or the pyridine ring via a carbon-carbon bond, and R 2 ~R 11 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. 【Chemistry 2】 In the general formula (N1), A represents a substituent having 3 to 30 carbon atoms and containing an aromatic ring or a heteroaromatic ring. 21 ~R 27 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and n is 2 or 3.
4. An organic compound represented by general formula (G1-2) (excluding organic compounds represented by general formula (N1)). 【Transformation 3】 In the general formula (G1-2), n2 and n3 represent integers of 0 to 3. When n2 is 0, n3 represents an integer of 1 to 3. 3 represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; R 3 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, the heteroaromatic ring being bonded to the arylene group via a carbon-carbon bond; R 2 and R 5 ~R 11 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. When n3 is 0, n2 represents an integer of 1 to 3, and Ar 2 represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; R 2 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, the heteroaromatic ring being bonded to the arylene group via a carbon-carbon bond; R 3 and R 5 ~R 11 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. 【Chemistry 4】 In the general formula (N1), A represents a substituent having 3 to 30 carbon atoms and containing an aromatic ring or a heteroaromatic ring. 21 ~R 27 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and n is 2 or 3.
5. An organic compound represented by general formula (G1-3) (excluding organic compounds represented by general formula (N1)). 【Transformation 5】 In the general formula (G1-3), n2 and n3 represent an integer of 0 to 3. When n2 is 0, n3 represents an integer of 1 to 3. 3 represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; R 3 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, the heteroaromatic ring being bonded to the arylene group via a carbon-carbon bond; R 2 and R 6 ~R 16 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. When n3 is 0, n2 represents an integer of 1 to 3, and Ar 2 represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; R 2 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, the heteroaromatic ring being bonded to the arylene group via a carbon-carbon bond; R 3 and R 6 ~R 16 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. 【Transformation 6】 In the general formula (N1), A represents a substituent having 3 to 30 carbon atoms and containing an aromatic ring or a heteroaromatic ring. 21 ~R 27 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and n is 2 or 3.
6. An organic compound represented by general formula (G2-1) (excluding organic compounds represented by general formula (N1)). 【Transformation 7】 (In general formula (G2-1), R 1 ~R 4 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms. 1 ~R 4 At least one of R represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, and the heteroaromatic ring is bonded to the pyridine ring via a carbon-carbon bond. 5 ~R 11 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. 【Transformation 8】 In the general formula (N1), A represents a substituent having 3 to 30 carbon atoms and containing an aromatic ring or a heteroaromatic ring. 21 ~R 27 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and n is 2 or 3.
7. An organic compound represented by general formula (G2-2) (excluding organic compounds represented by general formula (N1)). 【Chemistry 9】 (In general formula (G2-2), R 2 and R 3 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms. 2 and R 3 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, and the heteroaromatic ring is bonded to the pyridine ring via a carbon-carbon bond. 5 ~R 11 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. 【Chemistry 10】 In the general formula (N1), A represents a substituent having 3 to 30 carbon atoms and containing an aromatic ring or a heteroaromatic ring. 21 ~R 27 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and n is 2 or 3.
8. An organic compound represented by general formula (G2-3) (excluding organic compounds represented by general formula (N1)). 【Chemistry 11】 (In general formula (G2-3), R 2 and R 3 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms. 2 and R 3 represents a substituted or unsubstituted heteroaromatic ring having 3 to 40 carbon atoms, and the heteroaromatic ring is bonded to the pyridine ring via a carbon-carbon bond. 6 ~R 16 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. 【Chemistry 12】 In the general formula (N1), A represents a substituent having 3 to 30 carbon atoms and containing an aromatic ring or a heteroaromatic ring. 21 ~R 27 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and n is 2 or 3.
9. An organic compound represented by general formula (G1-1): 【Chemistry 13】 (In general formula (G1-1), n1 represents an integer of 0 to 3, and Ar 1 represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; R 1 represents any one of a pyridine ring, a pyrimidine ring, a triazine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, and a spiro[9H-fluorene-9,9'-[9H]xanthene ring]; R 2 ~R 11 each independently represents hydrogen (including deuterium), a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
10. An organic compound represented by structural formula (100), structural formula (106), structural formula (204), or structural formula (210). 【Chemistry 14】
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