Organic compound and light-emitting device
By using novel organic compounds as intermediate layer materials and combining them with photolithography to fabricate light-emitting devices, the performance and reliability problems of organic EL devices in the prior art have been solved, and a high-efficiency, low-power light-emitting device has been realized.
Patent Information
- Application Number
- CN202610030575.0
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2025-01-24
- Filing Date
- 2026-01-12
- Publication Date
- 2026-07-24
AI Technical Summary
Existing organic EL devices still have room for improvement in terms of performance and cost, especially facing issues such as burn-in and efficiency decline due to material degradation, and the exposure of the EL layer to the atmosphere during the photolithography process affects reliability.
By employing novel organic compounds, high-efficiency and reliable light-emitting devices are fabricated using photolithography. The organic compounds fabricated through photolithography are used as the intermediate layer of the light-emitting device, which improves the stability and luminous efficiency of the material and reduces the driving voltage.
This has resulted in a highly efficient and reliable light-emitting device, which improves luminous efficiency and color purity, reduces power consumption, and enhances the durability and reliability of the device.
Smart Images

Figure CN122444761A_ABST
Abstract
Description
Technical Field
[0001] One aspect of this 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 this aspect of the invention is not limited to the aforementioned technical fields. The technical field of one aspect of the invention disclosed in this specification relates to an object, method, or manufacturing method. One aspect of the invention relates to a process, machine, manufacture, or composition of matter. Therefore, more specifically, as an example of the technical field of one aspect of the invention disclosed in this specification, examples include semiconductor devices, display devices, liquid crystal display devices, lighting devices, energy storage devices, memory devices, imaging devices, methods for driving these devices, or methods for manufacturing these devices. Background Technology
[0002] Because light-emitting devices (also known as organic EL elements) that contain an organic compound as the light-emitting material between a pair of electrodes have the characteristics of being thin and lightweight, having a high response speed, and being able to be driven with low voltage, development related to displays that use light-emitting devices is underway.
[0003] Furthermore, because the light-emitting layer of this type of light-emitting device can be continuously formed in two dimensions, surface light emission can be achieved. Since this characteristic is difficult to obtain in point light sources such as incandescent lamps or LEDs, or line light sources such as fluorescent lamps, the aforementioned light-emitting device is highly valuable as a surface light source applicable to lighting and other applications.
[0004] For example, it is known that the pixels in the display area include a functional panel that includes a light-emitting element (light-emitting device) and a photoelectric conversion element (light-receiving device) (Patent Document 1).
[0005] While displays or lighting devices using light-emitting devices in this way are suitable for a variety of electronic devices, there is still room for improvement in their performance or cost competitiveness. Therefore, there is a growing demand for materials with better properties and easier handling, as well as methods for easily synthesizing such materials.
[0006] While the characteristics of organic EL devices have been significantly improved, they are still insufficient to meet the high demands for various properties such as efficiency and durability. In particular, to address issues unique to EL, such as burn-in, the smaller the efficiency degradation caused by degradation, the better.
[0007] Since degradation is greatly affected by the luminescent center material and the surrounding materials, the development of organic compound materials with good properties is becoming increasingly active.
[0008] Furthermore, in order to obtain higher-resolution light-emitting devices using organic EL devices, and instead of the evaporation method using metal masks, a technique has been developed to pattern organic compound layers using photolithography with photoresist or similar methods. By using photolithography, high-resolution display devices with EL layer spacing of several μm can be obtained (see, for example, Patent Document 2).
[0009] [Patent Document 1] No. WO2020 / 152556
[0010] [Patent Document 2] Japanese PCT International Application Translation No. 2018-521459 Summary of the Invention
[0011] One aspect of this invention aims to provide a novel organic compound. Another aspect aims to provide a method for synthesizing a novel organic compound. Additionally, one aspect aims to provide an organic compound that can be used in a light-emitting device. Another aspect aims to provide a novel organic compound that can be used as an intermediate layer in a tandem light-emitting device. Furthermore, one aspect aims to provide a light-emitting device with high luminous efficiency. Another aspect aims to provide a light-emitting device with high color purity. Another aspect aims to provide a light-emitting device with good reliability. Another aspect aims to provide any one of a display device, electronic device, and lighting device with low power consumption. Another aspect aims to provide any one of a display device, electronic device, and lighting device with high reliability. Another aspect aims to provide any one of a display device, electronic device, and lighting device with high color purity.
[0012] In addition, during the photolithography process, the surface of the EL layer must be exposed to the atmosphere.
[0013] Therefore, another objective of the present invention is to provide a novel light-emitting device manufactured via a photolithography process. Furthermore, another objective of the present invention is to provide a light-emitting device manufactured via a photolithography process that exhibits good efficiency. Additionally, another objective of the present invention is to provide a light-emitting device manufactured via a photolithography process that exhibits high reliability. Finally, another objective of the present invention is to provide a light-emitting device manufactured via a photolithography process that exhibits both high efficiency and high reliability.
[0014] The present invention can achieve any of the above objectives.
[0015] One aspect of the present invention is an organic compound represented by the general formula (G1).
[0016] [Chemical Formula 1]
[0017]
[0018] In the general formula (G1), Ar 1 and Ar 2 Each of the following groups independently represents an arylene group having 6 to 12 substituted or unsubstituted carbon atoms, or a heteroarylene group having 1 to 12 substituted or unsubstituted carbon atoms. Furthermore, n and m independently represent integers from 0 to 4. When n or m is an integer greater than 2, multiple Ar groups... 1 or multiple Ar 2 They can also be different. Additionally, Bfpm 1 and Bfpm 2 Each is independently represented by the following general formula (g1-1). Additionally, A is represented by any one of the following general formulas (g2-1) to (g2-6), where adjacent carbon atoms in A and Ar... 1 and Ar 2 Bonding.
[0019] [Chemical Formula 2]
[0020]
[0021] In the general formula (g1-1), X 1 R represents oxygen or sulfur. 1 To R 6 Each of these groups independently represents hydrogen (including deuterium), an alkyl group with 1 to 6 carbon atoms, a cyclic alkyl group with 3 to 10 carbon atoms (substituted or unsubstituted), an aryl group with 6 to 12 carbon atoms (substituted or unsubstituted), or a heteroaryl group with 1 to 12 carbon atoms (substituted or unsubstituted). Note that R... 1 To R 6 Any one of the representations in Ar is bound to Ar 1 Or Ar 2 The key.
[0022] [Chemical Formula 3]
[0023]
[0024] In general formulas (g2-1) to (g2-6), R 10 To R 17 and R 20 To R 75 Each of the following can be independently represented as hydrogen (including deuterium), an alkyl group having 1 to 6 carbon atoms, a cyclic alkyl group having 3 to 10 carbon atoms (substituted or unsubstituted), an aryl group having 6 to 12 carbon atoms (substituted or unsubstituted), a heteroaryl group having 1 to 12 carbon atoms (substituted or unsubstituted), or a group bonded to Ar. 1 Or Ar 2 The bond. Note that the bond is to Ar. 1and Ar 2 The key is R 10 To R 17 Any two adjacent R 20 To R 29 Any two adjacent R 30 To R 39 Any two adjacent R 40 To R 51 Any two adjacent R 52 To R 63 any two adjacent ones or R 64 To R 75 Any two adjacent ones in the middle.
[0025] In the above invention, R in general formula (g1-1) 3 R 5 and R 6 Any one of the representations in Ar is bound to Ar 1 Or Ar 2 The key.
[0026] One aspect of the present invention is an organic compound represented by the general formula (G2).
[0027] [Chemical Formula 4]
[0028]
[0029] In the general formula (G2), Ar 1 and Ar 2 Each of the following groups independently represents an arylene group having 6 to 12 substituted or unsubstituted carbon atoms, or a heteroarylene group having 1 to 12 substituted or unsubstituted carbon atoms. Furthermore, n and m independently represent integers from 0 to 4. When n or m is an integer greater than 2, multiple Ar groups... 1 or multiple Ar 2 They can also be completely different. Additionally, X 1 and X 2 R represents oxygen or sulfur independently, respectively. 1 To R 5 and R 101 To R 105 Each of the following can be independently represented: hydrogen (including deuterium), an alkyl group having 1 to 6 carbon atoms, a cyclic alkyl group having 3 to 10 carbon atoms (substituted or unsubstituted), an aryl group having 6 to 12 carbon atoms (substituted or unsubstituted), or a heteroaryl group having 1 to 12 carbon atoms (substituted or unsubstituted). Additionally, A can be represented by any one of the following general formulas (g2-1) to (g2-6), where adjacent carbons in A are adjacent to Ar. 1 and Ar 2 Bonding.
[0030] [Chemical Formula 5]
[0031]
[0032] In general formulas (g2-1) to (g2-6), R 10 To R 17 and R 20 To R 75 Each of the following can be independently represented as hydrogen (including deuterium), an alkyl group having 1 to 6 carbon atoms, a cyclic alkyl group having 3 to 10 carbon atoms (substituted or unsubstituted), an aryl group having 6 to 12 carbon atoms (substituted or unsubstituted), a heteroaryl group having 1 to 12 carbon atoms (substituted or unsubstituted), or a group bonded to Ar. 1 Or Ar 2 The bond. Note that the bond is to Ar. 1 and Ar 2 The key is R 10 To R 17 Any two adjacent R 20 To R 29 Any two adjacent R 30 To R 39 Any two adjacent R 40 To R 51 Any two adjacent R 52 To R 63 any two adjacent ones or R 64 To R 75 Any two adjacent ones in the middle.
[0033] One aspect of the present invention is an organic compound represented by the following general formula (G3).
[0034] [Chemical Formula 6]
[0035]
[0036] In the general formula (G3), Ar 1 and Ar 2 Each of the following groups independently represents an arylene group having 6 to 12 substituted or unsubstituted carbon atoms, or a heteroarylene group having 1 to 12 substituted or unsubstituted carbon atoms. Furthermore, n and m independently represent integers from 0 to 4. When n or m is an integer greater than 2, multiple Ar groups... 1 or multiple Ar 2 They can also be completely different. Additionally, X 1 and X 2 R can be oxygen or sulfur, respectively. 1 To R 5 R 12 To R 17 and R 101 To R 105Each of the following can be independently represented: hydrogen (including deuterium), alkyl with 1 to 6 carbon atoms, cyclic alkyl with 3 to 10 carbon atoms (substituted or unsubstituted), aryl with 6 to 12 carbon atoms (substituted or unsubstituted), or heteroaryl with 1 to 12 carbon atoms (substituted or unsubstituted).
[0037] In the above invention, X in the organic compound 1 It is oxygen. Additionally, n and m in organic compounds are both 1. Furthermore, Ar in organic compounds... 1 and Ar 2 It can be a substituted or unsubstituted phenylene.
[0038] One aspect of the present invention is an organic compound represented by structural formula (100) or structural formula (101).
[0039] [Chemical Formula 7]
[0040]
[0041] Another aspect of the present invention is a light-emitting device comprising any of the aforementioned organic compounds. Additionally, another aspect of the present invention is a display device comprising the aforementioned light-emitting device.
[0042] Another aspect of the present invention is an electronic device, comprising: the aforementioned light-emitting device; and a sensor, an operation button, a speaker, or a microphone.
[0043] Another aspect of the present invention is a lighting device including the above-described light-emitting device and frame.
[0044] According to one aspect of the present invention, a novel organic compound can be provided. According to one aspect of the present invention, a method for synthesizing the novel organic compound can be provided. Furthermore, according to one aspect of the present invention, an organic compound that can be used in a light-emitting device can be provided. According to one aspect of the present invention, a novel organic compound that can be used as an intermediate layer in a tandem light-emitting device can be provided. Furthermore, according to one aspect of the present invention, a light-emitting device with high luminous efficiency can be provided. Furthermore, according to one aspect of the present invention, a light-emitting device with high color purity can be provided. Furthermore, according to one aspect of the present invention, a light-emitting device with good reliability can be provided. Furthermore, according to one aspect of the present invention, any one of a display device, electronic device, and lighting device with low power consumption can be provided. Furthermore, according to one aspect of the present invention, any one of a display device, electronic device, and lighting device with high reliability can be provided. Furthermore, according to one aspect of the present invention, any one of a display device, electronic device, and lighting device with high color purity can be provided.
[0045] Furthermore, according to another aspect of the present invention, a novel light-emitting device manufactured by a photolithography process can be provided. Furthermore, according to another aspect of the present invention, a light-emitting device manufactured by a photolithography process and exhibiting good efficiency can be provided. Furthermore, according to another aspect of the present invention, a light-emitting device manufactured by a photolithography process with good reliability can be provided. Furthermore, according to another aspect of the present invention, a light-emitting device manufactured by a photolithography process with both good efficiency and reliability can be provided.
[0046] Note that the description of these effects does not preclude the existence of other effects. Note that one embodiment of the invention does not necessarily require all of the above-described effects. Note that effects other than those described above can be understood and extracted from the description, drawings, claims, etc. Attached Figure Description
[0047] Figure 1A and Figure 1B This is a schematic diagram of a light-emitting device;
[0048] Figures 2A to 2E It is a diagram illustrating the structure of a light-emitting device;
[0049] Figure 3A and Figure 3B These are the top view and cross-sectional view of the light-emitting device;
[0050] Figures 4A to 4E This is a cross-sectional view illustrating an example of a method for manufacturing a display device;
[0051] Figure 5A and Figure 5B This is a cross-sectional view illustrating an example of a method for manufacturing a display device;
[0052] Figures 6A to 6D This is a cross-sectional view illustrating an example of a method for manufacturing a display device;
[0053] Figures 7A to 7C This is a cross-sectional view illustrating an example of a method for manufacturing a display device;
[0054] Figures 8A to 8C This is a cross-sectional view illustrating an example of a method for manufacturing a display device;
[0055] Figures 9A to 9C This is a cross-sectional view illustrating an example of a method for manufacturing a display device;
[0056] Figures 10A to 10G This is a top view showing an example of the structure of a pixel;
[0057] Figures 11A to 11I This is a top view showing an example of the structure of a pixel;
[0058] Figure 12A and Figure 12B This is a perspective view showing an example of the structure of a display module;
[0059] Figure 13A and Figure 13B This is a cross-sectional view showing an example of the structure of a display device;
[0060] Figure 14 This is a perspective view showing an example of the structure of a display device;
[0061] Figure 15 This is a cross-sectional view showing an example of the structure of a display device;
[0062] Figure 16 This is a cross-sectional view showing an example of the structure of a display device;
[0063] Figures 17A to 17C These are cross-sectional and top views illustrating an example of the structure of a display device;
[0064] Figure 18 This is a cross-sectional view showing an example of the structure of a display device;
[0065] Figures 19A to 19C These are cross-sectional and top views illustrating an example of the structure of a display device;
[0066] Figures 20A to 20D This is a diagram illustrating an example of an electronic device;
[0067] Figures 21A to 21F This is a diagram illustrating an example of an electronic device;
[0068] Figures 22A to 22G This is a diagram illustrating an example of an electronic device;
[0069] Figure 23 The organic compounds manufactured in the examples 1 H-NMR spectrum;
[0070] Figure 24 The organic compounds manufactured in the examples 1 H-NMR spectrum;
[0071] Figure 25 It is a diagram illustrating the structure of a light-emitting device;
[0072] Figure 26 It is a graph illustrating the brightness-current density characteristics of a light-emitting device;
[0073] Figure 27 It is a graph illustrating the brightness-voltage characteristics of a light-emitting device;
[0074] Figure 28 It is a graph illustrating the current efficiency-luminance characteristics of a light-emitting device;
[0075] Figure 29 It is a graph illustrating the current density-voltage characteristics of a light-emitting device;
[0076] Figure 30 This is a diagram illustrating the electroemission spectrum of a light-emitting device;
[0077] Figure 31 It is a graph illustrating the brightness change of a light-emitting device relative to the driving time;
[0078] Figure 32 It is a diagram illustrating the structure of a light-emitting device;
[0079] Figure 33 It is a graph illustrating the brightness-current density characteristics of a light-emitting device;
[0080] Figure 34 It is a graph illustrating the brightness-voltage characteristics of a light-emitting device;
[0081] Figure 35 It is a graph illustrating the current efficiency-luminance characteristics of a light-emitting device;
[0082] Figure 36 It is a graph illustrating the current density-voltage characteristics of a light-emitting device;
[0083] Figure 37 This is a diagram illustrating the electroemission spectrum of a light-emitting device;
[0084] Figure 38 It is a graph illustrating the brightness change of a light-emitting device relative to the driving time;
[0085] Figure 39 It is a graph illustrating the brightness-current density characteristics of a light-emitting device;
[0086] Figure 40 It is a graph illustrating the brightness-voltage characteristics of a light-emitting device;
[0087] Figure 41 It is a graph illustrating the current efficiency-luminance characteristics of a light-emitting device;
[0088] Figure 42 It is a graph illustrating the current density-voltage characteristics of a light-emitting device;
[0089] Figure 43 It is a diagram illustrating the electroemission spectrum of a light-emitting device;
[0090] Figure 44 It is a graph illustrating the change in brightness of a light-emitting device relative to the driving time. Detailed Implementation
[0091] The embodiments of the present invention will now be described in detail with reference to the accompanying drawings. It should be noted that the present invention is not limited to the following description, and those skilled in the art will readily understand that its methods and details can be varied in many ways without departing from the spirit and scope of the invention. Therefore, the present invention should not be construed as being limited only to the contents described in the embodiments shown below.
[0092] Note that in this specification, etc., devices manufactured using metal masks or FMMs (Fine Metal Masks) are sometimes referred to as devices with MM (Metal Mask) structures. Furthermore, in this specification, etc., devices manufactured without metal masks or FMMs are sometimes referred to as devices with MML (Metal Mask Less) structures.
[0093] Implementation Method 1
[0094] In this embodiment, an organic compound of one aspect of the present invention is described.
[0095] Furthermore, one embodiment of the organic compound of the present invention can be used in the functional layer of a light-emitting device. For example, one embodiment of the organic compound of the present invention is suitable for an n-type layer of an electron transport layer or intermediate layer.
[0096] In particular, when the organic compound of one aspect of the present invention is mixed with a metal or metal compound, the nitrogen atoms included in the organic compound of one aspect of the present invention can form coordination bonds with the metal or metal compound (forming chelate complexes). Thus, the organic compound of one aspect of the present invention can be stabilized using a metal or metal compound that acts as an electron donor when mixed with a metal or metal compound. That is, when the organic compound of one aspect of the present invention is used as the intermediate layer or electron transport layer of a tandem light-emitting device, a light-emitting device capable of being driven at low voltage can be manufactured.
[0097] <Examples of organic compounds>
[0098] An organic compound of one aspect of the present invention may be represented by the following general formulas (G1) to (G3).
[0099] <<Example 1 of Organic Compounds>>
[0100] One aspect of the present invention is an organic compound represented by the general formula (G1).
[0101] [Chemical Formula 8]
[0102]
[0103] Note that in the general formula (G1), Ar1 and Ar 2 Each group independently represents an arylene group with 6 to 12 substituted or unsubstituted carbon atoms, or a heteroarylene group with 1 to 12 substituted or unsubstituted carbon atoms, where n and m independently represent integers from 0 to 4. Furthermore, when n or m is an integer greater than 2, multiple Ar groups... 1 or multiple Ar 2 They can also be different. Additionally, Bfpm 1 and Bfpm 2 Each is independently represented by the following general formula (g1-1). Additionally, A is represented by any one of the following general formulas (g2-1) to (g2-6), where adjacent carbon atoms in A and Ar... 1 and Ar 2 Bonding.
[0104] [Chemical Formula 9]
[0105]
[0106] Note that in the general formula (g1-1), X 1 R represents oxygen or sulfur. 1 To R 6 Each of these groups independently represents hydrogen (including deuterium), an alkyl group with 1 to 6 carbon atoms, a cyclic alkyl group with 3 to 10 carbon atoms (substituted or unsubstituted), an aryl group with 6 to 12 carbon atoms (substituted or unsubstituted), or a heteroaryl group with 1 to 12 carbon atoms (substituted or unsubstituted). Note that R... 1 To R 6 Any one of the representations in Ar is bound to Ar 1 Or Ar 2 The key.
[0107] R in general formula (g1-1) 3 R 5 and R 6 Any of the preferred options in Ar 1 Or Ar 2 Bonding. Especially, R 6 The substitution site is highly reactive, so it reacts with Ar. 1 Or Ar 2 Bonding can improve chemical stability, and is therefore a preferred method.
[0108] [Chemical Formula 10]
[0109]
[0110] Note that in general formulas (g2-1) to (g2-6), R 10 To R 17 and R 20 To R 75Each of the following can be independently represented as hydrogen (including deuterium), an alkyl group having 1 to 6 carbon atoms, a cyclic alkyl group having 3 to 10 carbon atoms (substituted or unsubstituted), an aryl group having 6 to 12 carbon atoms (substituted or unsubstituted), a heteroaryl group having 1 to 12 carbon atoms (substituted or unsubstituted), or a group bonded to Ar. 1 Or Ar 2 The bond. Note that the bond is to Ar. 1 and Ar 2 The key is R 10 To R 17 Any two adjacent R 20 To R 29 Any two adjacent R 30 To R 39 Any two adjacent R 40 To R 51 Any two adjacent R 52 To R 63 any two adjacent ones or R 64 To R 75 Any two adjacent ones in the middle.
[0111] Note regarding Ar 1 and Ar 2 When n or m is 0, any one of the general formulas (g2-1) to (g2-6) is bonded to Bfpm. 1 or Bfpm 2 Furthermore, in general formulas (g2-1) to (g2-6), adjacent carbon atoms are respectively bonded to Bfpm. 1 and Bfpm 2 Therefore, Bfpm 1 and Bfpm 2 The distance between the nitrogen atoms in the pyrimidine ring is shortened, resulting in stable stereocoordination. Therefore, it can coordinate with metals or metal compounds (forming chelate complexes). In other words, the interaction between the organic compound represented by the general formula (G1) and the metal or metal compound becomes easier, and is therefore preferred.
[0112] <<Examples of Organic Compounds 2>>
[0113] One aspect of the present invention is an organic compound represented by the general formula (G2).
[0114] [Chemical Formula 11]
[0115]
[0116] Note that in the general formula (G2), Ar 1 and Ar 2Each of the following groups independently represents an arylene group having 6 to 12 substituted or unsubstituted carbon atoms, or a heteroarylene group having 1 to 12 substituted or unsubstituted carbon atoms. Furthermore, n and m independently represent integers from 0 to 4. When n or m is an integer greater than 2, multiple Ar groups... 1 or multiple Ar 2 They can also be completely different. Additionally, X 1 and X 2 R represents oxygen or sulfur independently, respectively. 1 To R 5 and R 101 To R 105 Each of the following can be independently represented: hydrogen (including deuterium), alkyl group with 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 10 carbon atoms, substituted or unsubstituted aryl group with 6 to 12 carbon atoms, or substituted or unsubstituted heteroaryl group with 1 to 12 carbon atoms. Additionally, A can be represented by any one of the above general formulas (g2-1) to (g2-6), where adjacent carbons in A are adjacent to Ar. 1 and Ar 2 Bonding.
[0117] Additionally, in the general formula (G2), since it is located at X 1 The carbon at position 4 between the nitrogen atom and Ar 1 Or Ar 2 (A) bonding when n or m is 0, so Bfpm 1 and Bfpm 2 The shortened inter-nitrogen distance of the pyrimidine ring results in stable stereocoagulation. Therefore, it can coordinate with metals or metal compounds (forming chelate complexes). In other words, the interaction between the organic compound represented by the general formula (G2) and the metal or metal compound becomes easier, thereby reducing the driving voltage, making it preferred.
[0118] <<Examples of Organic Compounds 3>>
[0119] In addition, one aspect of the present invention is an organic compound represented by the general formula (G3).
[0120] [Chemical Formula 12]
[0121]
[0122] Note that in the general formula (G3), Ar 1 and Ar 2 Each of the following groups independently represents an arylene group having 6 to 12 substituted or unsubstituted carbon atoms, or a heteroarylene group having 1 to 12 substituted or unsubstituted carbon atoms. Furthermore, n and m independently represent integers from 0 to 4. When n or m is an integer greater than 2, multiple Ar groups... 1 or multiple Ar2 They can also be completely different. Additionally, X 1 and X 2 R can be oxygen or sulfur, respectively. 1 To R 5 R 12 To R 17 and R 101 To R 105 Each of the following can be independently represented: hydrogen (including deuterium), alkyl with 1 to 6 carbon atoms, cyclic alkyl with 3 to 10 carbon atoms (substituted or unsubstituted), aryl with 6 to 12 carbon atoms (substituted or unsubstituted), or heteroaryl with 1 to 12 carbon atoms (substituted or unsubstituted).
[0123] The general formula (G3), by having substituted naphthalene rings at positions 1 and 2, reduces symmetry, thus exhibiting low crystallinity and a high glass transition temperature. Therefore, when using general formula (G3) in light-emitting devices, crystallization in the thin film can be suppressed even after processes involving exposure to oxygen, water, and pharmaceutical solutions, thereby maintaining a highly amorphous film, making it preferred. Furthermore, sublimation properties are improved. Therefore, it can be easily purified to high purity, thereby increasing the yield.
[0124] Furthermore, in general formulas (G1) to (G3), in X 1 When oxygen is used, the triplet state has a higher energy level and can be synthesized more easily than when sulfur is used, making it a better choice as the main material for luminescent materials with green and blue emission wavelengths.
[0125] Furthermore, in general formulas (G1) to (G3), considering sublimation, n and m are preferably 0 or 1. Additionally, Bfpm 1 and Bfpm 2 The closer the spatial distance between the nitrogen atoms in each ring, the lower the driving voltage and the potential decrease in power consumption, making it a preferred option. Furthermore, in general formulas (G1) to (G3), when n and m are 1, compared to when n and m are 0, the two Bfpm rings (Bfpm...) 1 and Bfpm 2 The nitrogen in this compound exhibits less spatial distortion, which improves the stability of the compound, making it a preferred choice.
[0126] Additionally, in Ar 1 and Ar 2 In the case of substituted or unsubstituted phenylene, Bfpm 1 and Bfpm 2 Structures located on the same plane become stable conformations. At this point, Bfpm 1 and Bfpm 2The distance between nitrogen atoms in the pyrimidine ring is shortened, thus resulting in a stable conformation. Therefore, it readily coordinates with metals or metal compounds (forming chelate complexes), making it a more preferred conformation.
[0127] Additionally, the following examples illustrate the use of R in general formulas (G1) to (G3), general formula (g1-1), and general formulas (g2-1) to (g2-6). m (m is any integer) represents a specific example of a substituent.
[0128] Examples of aryl groups with 6 to 12 carbon atoms include phenylene, naphthylene, and biphenyl dimethyl.
[0129] In addition, examples of heteroaryl groups with 1 to 12 carbon atoms include pyridine-diyl, pyrimidine-diyl, pyrazine-diyl, pyridazine-diyl, triazine-diyl, bipyridine-diyl, phenanthroline-diyl, quinoxaline-diyl, quinazoline-diyl, benzoquinazoline-diyl, imidazole-diyl, triazole-diyl, oxadiazole-diyl, benzimidazole-diyl, furandiazine-diyl, benzofuran-pyrimidine-diyl, thiophene-diyl, furan-diyl, benzothiophene-diyl, benzofuran-diyl, dibenzothiophene-diyl, and dibenzofuran-diyl.
[0130] In addition, examples of alkyl groups having 1 to 6 carbon atoms include propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, and hexyl.
[0131] Examples of cycloalkyl groups having 3 to 10 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
[0132] Examples of aryl groups with 6 to 12 carbon atoms include phenyl, biphenyl, and naphthyl.
[0133] In addition, examples of heteroaryl groups having 1 to 12 carbon atoms include those having pyridine rings, pyrazine rings, pyrimidine rings, pyridazine rings, triazine rings, quinoline rings, quinazoline rings, isoquinoline rings, pyrrole rings, naphthidine rings, phenanthroline rings, quinoxaline rings, imidazole rings, benzimidazole rings, oxazole rings, isoxazole rings, thiazole rings, isothiazole rings, and benzofuran rings.
[0134] Furthermore, when the aforementioned arylene, heteroarylene, cycloalkyl, aryl, and heteroaryl groups have substituents, the substituents may be alkyl groups having 1 to 6 carbon atoms, cycloalkyl groups having 3 to 6 carbon atoms, cyano groups, or hydroxyl groups.
[0135] Specifically, when the substituent bonded to the aromatic group is an alkyl group having 1 to 6 carbon atoms, examples include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, and n-hexyl. Furthermore, examples of cycloalkyl groups having 3 to 6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
[0136] In addition, in general formulas (G1-1) to (G1-3), (G2-1) to (G2-3), (G3) to (G5) and (g1) to (g3), hydrogen may be appropriately replaced with deuterium.
[0137] <Specific examples>
[0138] Next, specific examples of organic compounds of one aspect of the present invention having structures represented by any of the general formulas (G1) to (G3) are shown below.
[0139] [Chemical Formula 13]
[0140]
[0141] [Chemical Formula 14]
[0142]
[0143] [Chemical Formula 15]
[0144]
[0145] [Chemical Formula 16]
[0146]
[0147] [Chemical Formula 17]
[0148]
[0149] [Chemical Formula 18]
[0150]
[0151] [Chemical Formula 19]
[0152]
[0153] [Chemical Formula 20]
[0154]
[0155] The organic compounds represented by the above structural formulas (100) to (138) and structural formulas (200) to (238) are examples of organic compounds represented by any of the general formulas (G1) to (G3), but the organic compounds of one aspect of the present invention are not limited thereto.
[0156] <Methods for the Synthesis of Organic Compounds>
[0157] Next, as an example of an organic compound according to one aspect of the present invention, a method for synthesizing an organic compound represented by the following general formula (G1) will be described. Note that various reactions can be used as the synthesis method for general formula (G1), and it is not limited to the synthesis method described below.
[0158] [Chemical Formula 21]
[0159]
[0160] In the general formula (G1), Ar 1 and Ar 2 Each of the following groups independently represents an arylene group with 6 to 12 substituted or unsubstituted carbon atoms, or a heteroarylene group with 1 to 12 substituted or unsubstituted carbon atoms. n and m independently represent integers from 0 to 4. When n or m is an integer greater than 2, multiple Ar groups... 1 or multiple Ar 2 They can also be different, Bfpm 1 and Bfpm 2 Each of these can be independently represented by the following general formula (g1-1), and A can be represented by any one of the following general formulas (g2-1) to (g2-6), Ar 1 and Ar 2 Each is bonded to an adjacent carbon atom in A.
[0161] [Chemical Formula 22]
[0162]
[0163] In the general formula (g1-1), X 1 R represents oxygen or sulfur. 1 To R 6 Each of the following independently represents hydrogen (including deuterium), an alkyl group having 1 to 6 carbon atoms, a cyclic alkyl group having 3 to 10 carbon atoms (substituted or unsubstituted), an aryl group having 6 to 12 carbon atoms (substituted or unsubstituted), or a heteroaryl group having 1 to 12 carbon atoms (substituted or unsubstituted), R 1 To R 6 Any one of the representations in Ar is bound to Ar 1 Or Ar 2 The key.
[0164] [Chemical Formula 23]
[0165]
[0166] In general formulas (g2-1) to (g2-6), R 10 To R 17 and R 20 To R 75 Each of the following can be independently represented as hydrogen (including deuterium), an alkyl group having 1 to 6 carbon atoms, a cyclic alkyl group having 3 to 10 carbon atoms (substituted or unsubstituted), an aryl group having 6 to 12 carbon atoms (substituted or unsubstituted), a heteroaryl group having 1 to 12 carbon atoms (substituted or unsubstituted), or a group bonded to Ar. 1 Or Ar 2 The bond. Note that the bond is to Ar. 1 and Ar 2 The key is R 10 To R 17 Any two adjacent R 20 To R 29 Any two adjacent R 30 To R 39 Any two adjacent R 40 To R 51 Any two adjacent R 52 To R 63 any two adjacent ones or R 64 To R 75 Any two adjacent ones in the middle.
[0167] Organic compounds represented by the general formula (G1) can be synthesized by the following synthetic scheme (S-1).
[0168] [Chemical Formula 24]
[0169]
[0170] In synthetic scheme (S-1), an organic compound represented by general formula (G1) can be obtained by coupling compounds (a1), (a2), and (a3) in a suitable solvent. Based on X... 1 and X 2 Or Y 1 and Y 2 The types of halogens indicated can be chosen arbitrarily in the order in which they react with boric acid, or the reactions can be carried out simultaneously. As a coupling reaction, the Suzuki-Miyaura reaction using a palladium catalyst is preferred.
[0171] In the above compound (a1), A is the same as in the general formula (G1). X 1 and X 2These can be independently represented as halogen, trifluoromethanesulfonyl, boric acid, borate ester, or cyclic triol borate, etc. In addition to lithium salts, cyclic triol borates can also be represented by potassium or sodium salts.
[0172] In compounds (a2) and (a3) above, Bfpm 1 and Bfpm 2 Ar 1 and Ar 2 The values of , n, and m are the same as in general formula (G1). 1 and Y 2 These can be independently represented as halogen, trifluoromethanesulfonyl, boric acid, borate ester, or cyclic triol borate, etc. In addition to lithium salts, cyclic triol borates can also be represented by potassium or sodium salts.
[0173] Examples of palladium catalysts that can be used for the coupling reaction shown in the above synthesis scheme include palladium(II) acetate, tetra(triphenylphosphine)palladium(O), bis(triphenylphosphine)palladium(II) dichloride, and allylpalladium(II) chloride dimer.
[0174] Examples of ligands for the aforementioned palladium catalysts include di(1-adamantyl)-n-butylphosphine, (±)-2,2'-bis(diphenylphosphine)-1,1'-binaphthyl, tri(o-tolyl)phosphine, triphenylphosphine, tricyclohexylphosphine, and di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine.
[0175] Examples of bases that can be used in the coupling reaction represented by the above synthetic scheme include organic bases such as potassium tert-butoxide, and inorganic bases such as potassium carbonate, sodium carbonate, and tripotassium phosphate.
[0176] Examples of solvents that can be used for the coupling reaction represented by the above synthetic scheme include toluene, xylene, mesitylene, benzene, tetrahydrofuran, dioxane, and diethylene glycol dimethyl ether. Note that the solvents that can be used are not limited to these.
[0177] Furthermore, the coupling reactions in the above synthetic schemes are not limited to the Suzuki-Miyaura reaction; they can also be achieved through the Yuda-Kosugi-Stille coupling reaction using organotin compounds, nucleophilic substitution reactions using Grignard reagents, and so on.
[0178] In addition, many of the above-mentioned compounds (a1), (a2) and (a3) are commercially available or can be synthesized.
[0179] The organic compound of one embodiment of the present invention can be synthesized as described above, but the present invention is not limited thereto and can also be synthesized by other synthetic methods.
[0180] This implementation method can be used in any combination with other implementation methods and examples.
[0181] Implementation Method 2
[0182] In this embodiment, the structure of a light-emitting device using the organic compound shown in Embodiment 1 will be described.
[0183] Displays that use organic EL elements (hereinafter also called light-emitting devices) as display elements (organic EL displays) have been in practical use for a long time. In order to achieve full-color display, the display typically includes pixels that emit light in at least the three colors of red, green and blue.
[0184] Each pixel contains a light-emitting device for each color of light emission. In a display that uses a side-by-side method (so-called separate coating method), each light-emitting device includes a different light-emitting material according to the light emission color of the corresponding pixel.
[0185] By using the organic compound described in Embodiment 1 as the charge-generating layer (intermediate layer) in a series-type light-emitting device, a display device with good display quality can be easily provided. The charge-generating layer will be described in detail in the following description of the light-emitting device. Therefore, one aspect of the present invention provides a light-emitting device in which the material used as the intermediate layer of a series-type light-emitting device is the organic compound described in Embodiment 1.
[0186] In addition, the organic compound described in Embodiment 1 has good carrier transport properties, especially excellent electron transport properties, so it is suitable for use as a carrier transport layer in light-emitting devices, and is particularly suitable for use as an electron transport layer, an electron injection layer or a host material.
[0187] One aspect of the present invention provides a light-emitting device that uses the organic compound described in Embodiment 1 as a charge-generating layer (intermediate layer). Additionally, a light-emitting device is provided that uses the organic compound described in Embodiment 1 as an electron transport material.
[0188] <Examples of light-emitting device structures>
[0189] Figure 1A This is a cross-sectional schematic diagram of a light-emitting device 10 according to 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 disposed between the pair of electrodes. The organic compound layer 103 includes at least a light-emitting layer 113.
[0190] In addition to the light-emitting layer 113 Figure 1A The organic compound layer 103 shown also 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.
[0191] Note that although this embodiment describes the first electrode 101 as the anode and the second electrode 102 as the cathode, the structure of the light-emitting device 10 is not limited to this. That is, the first electrode 101 can also be used as the cathode and the second electrode 102 as the anode, such that the stacking order of the layers between the electrodes is reversed. In other words, 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 can be stacked sequentially from the anode side.
[0192] Note that the structure of organic compound layer 103 is not limited to Figure 1A The structure shown may include at least one selected from hole injection layer 111, hole transport layer 112, electron transport layer 114, and electron injection layer 115. Alternatively, the organic compound layer 103 may also include a functional layer that can reduce the injection barrier of holes or electrons; improve the transport of holes or electrons; hinder the transport of holes or electrons; or suppress quenching caused by electrodes, etc. Note that the functional layer may be a single layer or a structure consisting of multiple layers stacked together.
[0193] Figure 1B It is shown Figure 1A A cross-sectional schematic diagram of an example of the light-emitting layer 113 shown. Figure 1B The luminescent layer 113 shown includes a host material 118 (organic compound 118_1 and organic compound 118_2) and a guest material 119 (luminescent substance).
[0194] Furthermore, as the guest material 119, a luminescent organic compound may be used, and the preferred luminescent organic compound is a substance capable of emitting phosphorescence (hereinafter also referred to as a phosphorescent compound).
[0195] Furthermore, in the light-emitting layer 113, the host material 118 exists in the manner with the largest weight ratio, and the guest material 119 is dispersed in the host material 118. In addition, 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.
[0196] Furthermore, the host material 118 (organic compound 118_1 and organic compound 118_2) in the light-emitting layer 113 preferably forms an exciplex. An exciplex is an excited state formed by two or more substances. In the case of photoexcitation, the exciplex is formed by the interaction of one substance in the excited state with another substance in the ground state.
[0197] <Basic Structure of Light-Emitting Devices>
[0198] The following is for reference Figures 2A to 2E A more detailed explanation of the basic structure of light-emitting devices will be provided. Figure 2A This illustrates a light-emitting device with a structure (monolayer structure) comprising an organic compound layer (also known as an EL layer) having a light-emitting layer between a pair of electrodes. Specifically, an organic compound layer 103 is included between the first electrode 101 and the second electrode 102.
[0199] also, Figure 2B This shows that multiple ( ) are included between a pair of electrodes. Figure 2B A light-emitting device comprising two organic compound layers (103a, 103b) and a charge-generating layer 106 between the organic compound layers, forming a stacked structure (tandem structure). A tandem structure light-emitting device can achieve high efficiency without changing the current.
[0200] The charge generation layer 106 functions as follows: when a potential difference is generated between the first electrode 101 and the second electrode 102, it injects electrons into one organic compound layer (103a or 103b) and holes into the other organic compound layer (103b or 103a). Thus, in Figure 2B When a voltage is applied in such a way that the potential of the first electrode 101 is higher than the potential 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.
[0201] Furthermore, from the viewpoint of light extraction efficiency, the charge generation layer 106 preferably has light transmittance to visible light (specifically, the visible light transmittance of the charge generation layer 106 is 40% or more). Moreover, it functions even if the electrical conductivity of the charge generation layer 106 is lower than that of the first electrode 101 and the second electrode 102.
[0202] also, Figure 2CThe diagram illustrates a stacked structure of an organic compound layer 103 in a light-emitting device according to one embodiment of the present invention. Note that in this case, the first electrode 101 is used as the anode, and the second electrode 102 is used as the 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 on the first electrode 101. Note that multiple light-emitting layers with different emitting colors can also be stacked as the light-emitting layer 113. For example, light-emitting layers containing red emitting materials, green emitting materials, and blue emitting materials can be stacked with or without separation from layers containing carrier transport materials. Alternatively, a light-emitting layer containing yellow emitting materials and a light-emitting layer containing blue emitting materials can be combined. Note that the stacked structure of the light-emitting layer 113 is not limited to the above structures. For example, multiple light-emitting layers with the same emitting color can also be stacked as the light-emitting layer 113. For example, a first light-emitting layer containing a blue luminescent material and a second light-emitting layer containing a blue luminescent material can be stacked, with or without separation of layers containing charge carrier transport materials. Stacking multiple light-emitting layers with the same luminescent color can sometimes improve reliability compared to a single layer. Furthermore, in cases such as... Figure 2B In the case of a series structure with multiple light-emitting layers, each light-emitting layer also has a structure in which they are stacked sequentially from the anode side as described above. Furthermore, when the first electrode 101 is the cathode and the second electrode 102 is the anode, the stacking order of the organic compound layers 103 is reversed. Specifically, on the first electrode 101 of the cathode, 111 is the electron injection layer, 112 is the electron transport layer, 113 is the light-emitting layer, 114 is the hole transport layer, and 115 is the hole injection layer.
[0203] By appropriately combining luminescent layers 113 within the organic compound layers (103, 103a, 103b) containing luminescent materials and multiple substances, fluorescent or phosphorescent emission exhibiting the desired emission color can be obtained. Furthermore, the luminescent layers 113 can also be a stacked structure with different emission colors. In this case, different materials can be used as the luminescent materials and other substances for each luminescent layer used in the stacking. Alternatively, materials from... Figure 2B The structure shown has multiple organic compound layers (103a, 103b) that produce different luminescent colors. In this case, different materials can be used as luminescent substances for each luminescent layer and other substances.
[0204] Furthermore, in one embodiment of the light-emitting device of the present invention, for example, by making Figure 2CThe first electrode 101 shown is a reflective electrode, and the second electrode 102 is a semi-transmissive-semi-reflective electrode with an optical microcavity resonator (microcavity) structure. This allows the light emitted from the light-emitting layer 113 in the organic compound layer 103 to resonate between the two electrodes, thereby enhancing the light emitted from the second electrode 102. This facilitates high-definition imaging. Furthermore, because the light emission intensity in the frontal direction at a specific wavelength can be enhanced, low power consumption can be achieved.
[0205] When the first electrode 101 of the light-emitting device is a reflective electrode composed of a stacked structure of a reflective conductive material and a light-transmitting conductive material (transparent conductive film), optical adjustment can be performed by adjusting the thickness of the transparent conductive film. Specifically, it is preferable to adjust the thickness of the transparent conductive film so that when the wavelength of the light obtained from the light-emitting layer 113 is λ, the optical distance (product of thickness and refractive index) between the first electrode 101 and the second electrode 102 is mλ / 2 (note that m is an integer greater than or equal to 1) or a value close to it.
[0206] Furthermore, in order to amplify the light of the desired wavelength (wavelength: λ) obtained from the light-emitting layer 113, it is preferable to adjust the optical distances from the first electrode 101 to the region in the light-emitting layer 113 where light emission is possible (light-emitting region) and from the second electrode 102 to the region in the light-emitting layer 113 where light emission is possible (light-emitting region) are both (2m'+1)λ / 4 (note that m' is an integer greater than or equal to 1) or close to it. Note that the "light-emitting region" described here refers to the recombination region of holes and electrons in the light-emitting layer 113.
[0207] By making the above optical adjustments, the spectrum of specific monochromatic light that can be obtained from the light-emitting layer 113 can be narrowed, thereby obtaining light emission with good color purity.
[0208] Furthermore, in the above-described case, strictly speaking, the optical distance between the first electrode 101 and the second electrode 102 can be considered as the total thickness from the reflective region in the first electrode 101 to the reflective region in the second electrode 102. However, since it is difficult to accurately determine the positions of the reflective regions in the first electrode 101 and the second electrode 102, the aforementioned effect can be sufficiently obtained by assuming any position in the first electrode 101 and the second electrode 102 as a reflective region. Additionally, strictly speaking, the optical distance between the first electrode 101 and the light-emitting layer capable of obtaining light of the desired wavelength can be considered as the optical distance between the reflective region in the first electrode 101 and the light-emitting region in the light-emitting layer capable of obtaining light of the desired wavelength. However, since it is difficult to accurately determine the reflective region in the first electrode 101 and the light-emitting region in the light-emitting layer capable of obtaining light of the desired wavelength, the aforementioned effect can be sufficiently obtained by assuming any position in the first electrode 101 as a reflective region and any position in the light-emitting layer capable of obtaining light of the desired wavelength as a light-emitting region.
[0209] Figure 2D The light-emitting device shown is a series-connected device. By employing a series structure, a light-emitting device capable of high brightness can be achieved. Furthermore, the series structure improves reliability because it reduces the current required to achieve the same brightness compared to a single structure. Additionally, power consumption can be reduced.
[0210] Figure 2E The light-emitting device shown is Figure 2B An example of a series-connected light-emitting device, as shown in the attached figure, has a structure in which three organic compound layers (103a, 103b, 103c) sandwich a charge-generating layer (106a, 106b) in a stacked configuration. Each of the three organic compound layers (103a, 103b, 103c) includes a light-emitting layer (113a, 113b, 113c), and the emission colors of each light-emitting layer can be freely combined. For example, a structure can be used where light-emitting layer 113a emits blue, light-emitting layer 113b emits any one of red, green, and yellow, and light-emitting layer 113c emits blue; alternatively, a structure can be used where light-emitting layer 113a emits red, light-emitting layer 113b emits any one of blue, green, and yellow, and light-emitting layer 113c emits red.
[0211] Furthermore, in the light-emitting device according to one aspect of the present invention described above, at least one of the first electrode 101 and the second electrode 102 is a light-transmitting electrode (transparent electrode, semi-transmissive-semi-reflective electrode, etc.). When the light-transmitting electrode is a transparent electrode, the transmittance of visible light by the transparent electrode is 40% or more. Furthermore, when the electrode is a semi-transmissive-semi-reflective electrode, the reflectance of visible light by the semi-transmissive-semi-reflective electrode is 20% or more and 80% or less, preferably 40% or more and 70% or less. Moreover, the resistivity of these electrodes is preferably 1×10⁻⁶. -2 Below Ωcm.
[0212] Furthermore, in the light-emitting device according to one embodiment of the present invention described above, when one of the first electrode 101 and the second electrode 102 is a reflective electrode (reflective electrode), the visible light reflectance of the reflective electrode is 40% or more and 100% or less, preferably 70% or more and 100% or less. Furthermore, the resistivity of this electrode is preferably 1×10⁻⁶. -2 Below Ωcm.
[0213] <Specific Structure of Light-Emitting Devices>
[0214] Next, a specific structure of a light-emitting device according to one aspect of the present invention will be described. Furthermore, reference is made here to a device having a series structure. Figure 2D Please explain. Note that... Figure 2A and Figure 2C The light-emitting device with a single structure shown also employs the same organic compound layer structure. Furthermore, in Figure 2D In the case of the light-emitting device having a microcavity structure, a reflective electrode is formed as the first electrode 101, and a semi-transmissive-semi-reflective electrode is formed as the second electrode 102. Thus, the electrodes can be formed using a single desired electrode material or multiple electrode materials in a single layer or stacked layers. Furthermore, the second electrode 102 is formed by appropriately selecting a material after forming the organic compound layer 103b.
[0215] Materials for Light-Emitting Devices
[0216] <<Emitting Layer>>
[0217] The luminescent layers (113, 113a, 113b, 113c) are layers containing luminescent materials. Note that materials exhibiting luminescent colors such as blue, purple, blue-violet, green, yellow-green, yellow, orange, and red can be appropriately used as luminescent materials for the luminescent layers (113, 113a, 113b, 113c). Furthermore, when multiple luminescent layers are included, by using different luminescent materials in each luminescent layer, structures exhibiting different luminescent colors can be obtained (e.g., white light obtained by combining luminescent colors that are complementary colors). Alternatively, a stacked structure in which a single luminescent layer contains different luminescent materials can also be used.
[0218] In addition, the luminescent layers (113, 113a, 113b, 113c) may contain one or more organic compounds (host materials, etc.) in addition to the luminescent material (guest material).
[0219] Specifically, the light-emitting layer 113 can be a reference. Figure 1B The structure is described below. In the luminescent layer 113, the host material 118 has the largest weight ratio, and the guest material 119 (phosphorescent compound) is dispersed in the host material 118. Preferably, the T1 energy level of the host material 118 (organic compound 118_1 and organic compound 118_2) of the luminescent layer 113 is higher than the T1 energy level of the guest material (guest material 119) of the luminescent layer 113.
[0220] The lowest triplet excitation level (T1 level) can be calculated from the luminescent end obtained by measuring the emission spectrum (phosphorescence spectrum) of a thin film using a deposited sample at a low measurement temperature (e.g., 10 K). Furthermore, the sample state when measuring the emission spectrum of the luminescent center can be a thin film or a solution; from the viewpoint of verifying the state of isolated molecules, a solution is preferred. As the solvent for this solution, solvents with low polarity, such as toluene or chloroform, are preferred. Additionally, if the luminescent center is a phosphorescent compound, the temperature for measuring the lowest triplet excitation level (T1 level) can be low (e.g., 10 K) or room temperature (e.g., 298 K), and can be calculated from the luminescent end obtained by measuring the emission spectrum (phosphorescence spectrum). Note that the luminescent end can be calculated by drawing a tangent at the maximum slope of the shortest wavelength side of the peak (or shoulder) observed at the shortest wavelength of the emission spectrum (phosphorescence spectrum) and using the intersection of this tangent with the horizontal axis (wavelength) or the baseline.
[0221] As luminescent materials that can be used as guest materials, there are, for example, substances that exhibit red luminescence. Furthermore, substances exhibiting red luminescence are preferably substances exhibiting phosphorescence, and organometallic complexes are particularly preferred. Examples of such luminescent materials include: (diisobutyrylmethane)bis[4,6-bis(3-methylphenyl)pyrimidinyl]iridium(III) (abbreviated as: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinyl](dineopentaylmethane)iridium(III) (abbreviated as: [Ir(5mdppm)2(dpm)]), bis[4,6-di(naphthyl-1-yl)pyrimidinyl](dineopentaylmethane)iridium(III) (abbreviated as: [Ir(d1npm)2(dpm)]), etc., which have a pyrimidine skeleton. Organometallic iridium complexes; bis(2,3,5-triphenylpyrazine)iridium(III) (abbreviated as [Ir(tppr)2(acac)]), bis(2,3,5-triphenylpyrazine)(dinepentylmethane)iridium(III) (abbreviated as [Ir(tppr)2(dpm)]), bis(acetyrazine)bis[2,3-bis(4-fluorophenyl)quinoxaloline]iridium(III) (abbreviated as [Ir(Fdpq)2(acac)]), etc., organometallic iridium complexes with a pyrazine skeleton; tris(1-phenylisoquinoline-N,C 2’ Iridium (III) (abbreviated as: [Ir(piq)3]), bis(1-phenylisoquinoline-N,C) 2’ ) Iridium(III) acetylacetone (abbreviated as: [Ir(piq)2(acac)]), (3,7-diethyl-4,6-nonanedione-κO) 4 ,κO 6 ) bis[2,4-dimethyl-6-[7-(1-methylethyl)-1-isoquinolinyl-κN]phenyl-κC]iridium(III), (3,7-diethyl-4,6-nonanedione-κO) 4 ,κO 6Organometallic iridium complexes with a pyridine skeleton, such as bis[2,4-dimethyl-6-[5-(1-methylethyl)-2-quinolinyl-κN]phenyl-κC]iridium(III); platinum complexes such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviated as PtOEP); and rare earth metal complexes such as tris(1,3-diphenyl-1,3-propanedionato) (monopraninolite) europium(III) (abbreviated as [Eu(DBM)3(Phen)]) and tris[1-(2-thiophenecarboxyl)-3,3,3-trifluoroacetone] (monopraninolite) europium(III) (abbreviated as [Eu(TTA)3(Phen)]). All of these substances exhibit emission peaks in the wavelength region of 600 nm to 700 nm. Furthermore, organometallic iridium complexes with a pyrazine framework can provide red luminescence with good colorimetric properties. Additionally, other known substances that exhibit red phosphorescence can also be used.
[0222] In the absence of using a red luminescent material as the luminescent material or having luminescent devices with different structures within a luminescent device, the luminescent material can also be a fluorescent luminescent material, a phosphorescent luminescent material, a material exhibiting thermally activated delayed fluorescence (TADF), or other luminescent materials.
[0223] In the luminescent layer 113, materials that can be used to emit fluorescent light can be, for example, the following substances. In addition, other fluorescent light-emitting materials can also be used.
[0224] Examples include 5,6-bis[4-(10-phenyl-9-anthrayl)phenyl]-2,2'-bipyridine (abbreviated as PAP2BPy), 5,6-bis[4'-(10-phenyl-9-anthrayl)biphenyl-4-yl]-2,2'-bipyridine (abbreviated as PAPP2BPy), N,N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluorene-9-yl)phenyl]pyrene-1,6-diamine (abbreviated as 1,6FLPAPrn), N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluorene-9-yl)phenyl]pyrene-1,6-diamine (abbreviated as 1,6mMemFLPAPrn), and N,N'-bis[4-(9H-9H-fluorene-9-yl)phenyl]pyrene-1,6-diamine (abbreviated as 1,6mMemFLPAPrn). [-carbazole-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazole-9-yl)-4'-(10-phenyl-9-anthrayl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazole-9-yl)-4'-(9,10-diphenyl-2-anthrayl)triphenylamine (abbreviation: 2YGAPPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), dinaphthalene, 2,5,8,11-tetra-tert-butyl dinaphthalene (abbreviation: TBP), 4-(10-phenyl-9-anthrayl)-4'-(9-phenyl-9H-carbazole-9- ... N,N''-(2-tert-butylanthracene-9,10-diyl-4,1-phenylene)bis(N,N',N'-triphenyl-1,4-phenylenediamine) (DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-anthrayl)phenyl]-9H-carbazole-3-amine (2PCAPPA), N-[4-(9,10-diphenyl-2-anthrayl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (2DPAPPA), N,N,N',N',N',N'',N'',N''',N'''-octaphenyldibenzo[g,p](chrys) N-(9,10-diphenyl-2-anthrayl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as: DBC1), coumarin 30, N-(9,10-diphenyl-2-anthrayl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as: 2PCAPA), N-[9,10-bis(biphenyl-2-yl)-2-anthrayl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as: 2PCABPhA), N-(9,10-diphenyl-2-anthrayl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as: 2DPAPA), N-[9,10-bis(biphenyl-2-yl)-2-anthrayl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as: 2DPABPhA), 9,10-Bis(biphenyl-2-yl)-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracene-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracene-9-amine (abbreviation: DPhAPhA), coumarin 545T, N,N'-diphenylquinacridone (abbreviation: DPQd), rubrene, 5,12-bis(biphenyl-4-yl)-6,11-diphenyltetraphenyl (abbreviation: BPT), 2-(2-{2-[4-(dimethylamino)phenyl]vinyl}-6-methyl-4H-pyran-4-yl)malonitrile (abbreviation: DCM1), 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H, 5H-benzo[ij]quinazine-9-yl)vinyl]-4H-pyran-4-ylidene}malonium (abbreviation: DCM2), N,N,N',N'-tetra(4-methylphenyl)tetraphenyl-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetra(4-methylphenyl)acenaphthene[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinazine-9-yl)vinyl]-4H-pyran-4-ylidene}malonium (abbreviation: DCJT) I) 2-{2-tert-butyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinazin-9-yl)vinyl]-4H-pyran-4-ylidene}malonium (abbreviation: DCJTB), 2-(2,6-bis{2-[4-(dimethylamino)phenyl]vinyl}-4H-pyran-4-ylidene)malonium (abbreviation: BisDCM), 2-{2,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinazin-9-yl)vinyl]-4H-pyran-4-ylidene}malonium (abbreviation: BisDCJ) TM), N,N'-diphenyl-N,N'-(1,6-pyrene-diyl)bis[(6-phenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03), N,N'-diphenyl-N,N'-bis(9-phenyl-9H-carbazole-2-yl)naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviation: 3,10PCA2Nbf(IV)-02), 3,10-bis[N-(dibenzofuran-3-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10FrA2Nbf(IV)-02), etc. In particular, 1,6FLPAPrn, 1,6mMemFLPAPrn, 1,Fused aromatic diamine compounds, such as pyrene diamine compounds like 6BnfAPrn-03, possess high hole-trapping ability, high luminescence efficiency, and high reliability, making them a preferred choice.
[0225] In addition, 5,9-diphenyl-5H,9H-[1,4]benzozaborane[2,3,4-kl]phenazaborane (abbreviated as DABNA-1), 9-(biphenyl-3-yl)-N,N,5,11-tetraphenyl-5H,9H-[1,4]benzozaborane[2,3,4-kl]phenazaborane-3-amine (abbreviated as DABNA-2), and 2,12-bis(tert-butyl)-5,9-bis(4-tert-butylphenyl)-N,N-diphenyl-5H,9H-[1,4]benzozaborane[2,3,4-kl]phenazaborane can be used appropriately. Azabor-7-amine (abbreviation: DPhA-tBu4DABNA), 2,12-di(tert-butyl)-N,N,5,9-tetra(4-tert-butylphenyl)-5H,9H-[1,4]benzozaborane[2,3,4-kl]phenazabor-7-amine (abbreviation: tBuDPhA-tBu4DABNA), 2,12-di(tert-butyl)-5,9-di(4-tert-butylphenyl)-7-methyl-5H,9H-[1,4]benzozaborane[2,3,4-kl]phenazaborane (abbreviation: Me-tBu4DABNA), N 7 N 7 N 13 N 13 Nitrogen- and boron-containing fused heteroaromatic compounds, especially those with a diaza-boron-naphtho-anthracene skeleton, can produce blue luminescence with good color purity due to their narrow emission spectra.
[0226] In addition, compounds with an indole skeleton, such as 9,10,11-tris[3,6-bis(1,1-dimethylethyl)-9H-carbazole-9-yl]-2,5,15,18-tetra(1,1-dimethylethyl)indolo[3,2,1-de]indolo[3',2',1':8,1][1,4]benzozaborane[2,3,4-kl]phenazaborane (abbreviated as: BBCz-G) and 9,11-bis[3,6-bis(1,1-dimethylethyl)-9H-carbazole-9-yl]-2,5,15,18-tetra(1,1-dimethylethyl)indolo[3,2,1-de]indolo[3',2',1':8,1][1,4]benzozaborane[2,3,4-kl]phenazaborane (abbreviated as: BBCz-Y), can be appropriately used.
[0227] When a phosphorescent material is used as a luminescent material in the luminescent layer 113, the following materials can be used as examples.
[0228] Examples include: tri{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN} 2 Organometallic iridium complexes with a 4H-triazole skeleton, such as iridium(III)[Ir(mpptz-dmp)3] and tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazole (triazolato))iridium(III)[Ir(Mptz)3]; tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazole]iridium(III)[Ir(Mptz1-mp)3] and tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazole)iridium(III) Abbreviations: [Ir(Prptz1-Me)3], etc., organometallic iridium complexes with a 1H-triazole skeleton; fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazolium]iridium(III) (abbreviation: [Ir(iPrpim)3]), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmpimpt-Me)3]), tris(2-{1-[2,6-bis(1-methylethyl)phenyl]-1H-imidazolium-2-yl-κN 3 Organometallic iridium complexes with an imidazole skeleton, such as}-4-cyanophenyl-κC)iridium(III) (abbreviated as CNImIr); tris[(6-tert-butyl-3-phenyl-2H-imidazo[4,5-b]pyrazin-1-yl-κC] 2Organometallic iridium complexes with a benzimidazole skeleton, such as phenyl-κC]iridium(III) (abbreviated as [Ir(cb)3]); and bis[2-(4',6'-difluorophenyl)pyridinium-N,C 2’ Iridium(III) tetra(1-pyrazolyl)borate (abbreviated as: FIr6), bis[2-(4',6'-difluorophenyl)pyridinium-N,C 2’ Iridium(III) pyridine carboxylate (abbreviated as FIRPIC), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinium-N,C 2’} Iridium(III)pyridinecarboxylate (abbreviated as: [Ir(CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyridin-N,C 2’ Organometallic iridium complexes such as iridium(III) acetylacetone (abbreviated as FIr(acac)) with phenylpyridine derivatives having electron-withdrawing groups as ligands. These substances are compounds that emit blue phosphorescence and have emission peaks in the wavelength region of 440 nm to 520 nm.
[0229] In addition, examples include: tris(4-methyl-6-phenylpyrimidine)iridium(III) (abbreviated as [Ir(mppm)3]), tris(4-tert-butyl-6-phenylpyrimidine)iridium(III) (abbreviated as [Ir(tBuppm)3]), (acetylacetonate)bis(6-methyl-4-phenylpyrimidine)iridium(III) (abbreviated as [Ir(mppm)2(acac)]), (acetylacetonate)bis(6-tert-butyl-4-phenylpyrimidine)iridium(III) (abbreviated as [Ir(tBuppm)2(acac)]), (acetylacetonate)bis[6-(2-norborneol)-4-phenylpyrimidine]iridium(III) (abbreviated as [Ir(nbppm)2(acac)]), (acetylacetonate)bis[5-methyl Organometallic iridium complexes with a pyrimidine skeleton, such as [Ir(mpmppm)2(acac)]((acetylacetonate)bis(4,6-diphenylpyrimidine)iridium(III)]([Ir(dppm)2(acac)]); organometallic iridium complexes with a pyrazine skeleton, such as [Ir(mppr-Me)2(acac)]((acetylacetonate)bis(5-isopropyl-3-methyl-2-phenylpyrazine)iridium(III)]([Ir(mppr-iPr)2(acac)]); and tris(2-phenylpyridinium-N,C 2’ Iridium (III) (abbreviated as: [Ir(ppy)3]), bis(2-phenylpyridinium-N,C) 2’Iridium (III) acetylacetone (abbreviated as: [Ir(ppy)2(acac)]), bis(benzo[h]quinoline)iridium (III) acetylacetone (abbreviated as: [Ir(bzq)2(acac)]), tri(benzo[h]quinoline)iridium (III) (abbreviated as: [Ir(bzq)3]), tri(2-phenylquinoline-N,C 2’ Iridium (III) (abbreviated as: [Ir(pq)3]), bis(2-phenylquinoline-N,C) 2’ Iridium(III)acetylacetone (abbreviated as: [Ir(pq)2(acac)]), [2-d3-methyl-8-(2-pyridyl-κN)benzofurano[2,3-b]pyridyl-κC]bis[2-(5-d3-methyl-2-pyridyl-κN) 2 )Phenylen-κC]iridium(III) (abbreviated as: Ir(5mppy-d3)2(mbfpypy-d3)), {2-(methyl-d3)-8-[4-(1-methylethyl-1-d)-2-pyridyl-κN]benzofurano[2,3-b]pyridin-7-yl-κC}bis{5-(methyl-d3)-2-[5-(methyl-d3)-2-pyridyl-κN]phenyl-κC}iridium(III) ( Abbreviations: Ir(5mtpy-d6)2(mbfpypy-iPr-d4)), [2-(methyl-d3)-8-(2-pyridyl-κN)benzofurano[2,3-b]pyridine-κC]bis[2-(2-pyridyl-κN)phenyl-κC]iridium(III) (abbreviations: Ir(ppy)2(mbfpypy-d3)), [2-(4-d3-methyl-5-phenyl-2-pyridyl-κN) 2 [Phenyl-κC]bis[2-(5-d3-methyl-2-pyridyl-κN] 2Organometallic iridium complexes with a pyridine skeleton, such as [Ir(5mppy-d3)2(mdppy-d3)], [2-methyl-8-(2-pyridyl-κN)benzofurano[2,3-b]pyridine-κC]bis[2-(2-pyridyl-κN)phenyl-κC]iridium(III) (abbreviated as Ir(ppy)2(mbfpypy)), and [2-(4-methyl-5-phenyl-2-pyridyl-κN)phenyl-κC]bis[2-(2-pyridyl-κN)phenyl-κC]iridium(III) (abbreviated as Ir(ppy)2(mdppy)); and rare earth metal complexes such as tri(acetylacetonate)(monophenanthroline)terbium(III) (abbreviated as [Tb(acac)3(Phen)]). The aforementioned substances are primarily compounds that exhibit green phosphorescence and have emission peaks in the wavelength region of 500 nm to 600 nm. Furthermore, organometallic iridium complexes with a pyrimidine framework are particularly preferred due to their exceptionally high reliability or luminescent efficiency.
[0230] In addition, the aforementioned red phosphorescent material can also be used. Furthermore, in addition to the phosphorescent compounds mentioned above, known phosphorescent compounds can also be selected and used.
[0231] Fullerenes and their derivatives, acridines and their derivatives, and eosin derivatives can be used as TADF materials. In addition, metal porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd) can also be used. Examples of metalloporphyrins include protoporphyrin-tin fluoride complexes (SnF2(Proto IX)), mesoporphyrin-tin fluoride complexes (SnF2(Meso IX)), hematoporphyrin-tin fluoride complexes (SnF2(Hemato IX)), tetramethyl coprophyrin-tin fluoride complexes (SnF2(Copro III-4Me)), octaethylporphyrin-tin fluoride complexes (SnF2(OEP)), protoporphyrin-tin fluoride complexes (SnF2(Etio I)), and octaethylporphyrin-platinum chloride complexes (PtCl2OEP), all represented by the following structural formulas.
[0232] [Chemical Formula 25]
[0233]
[0234] In addition, the following structural formulas can also be used: 2-(biphenyl-4-yl)-4,6-bis(12-phenylindol[2,3-a]carbazole-11-yl)-1,3,5-triazine (abbreviated as: PIC-TRZ), 9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviated as: PCCzTzn), 9-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-3,3'-bi-9H-carbazole (abbreviated as: PCCzPTzn), 2-[4-(10H-phenoxazine-10-yl)phenyl]-4,6-diphenyl-1,3,5- Triazine (PXZ-TRZ), 3-[4-(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (PPZ-3TPT), 3-(9,9-dimethyl-9H-acridin-10-yl)-9H-oxazanthracene-9-one (ACRXTN), bis[4-(9,9-dimethyl-9,10-dihydroacridin)phenyl]sulfone (DMAC-DPS), 10-phenyl-10H,10'H-spiro[acridin-9,9'-anthracene]-10'-one (ACRSA), and other heterocyclic compounds possessing one or both π-electron-rich and π-electron-deficient heterocyclic rings. These heterocyclic compounds, possessing both π-electron-rich and π-electron-deficient heterocyclic rings, exhibit high electron and hole transport capabilities and are therefore preferred. Among the skeletons with π-electron-deficient heteroaromatic rings, pyridine, diazine (pyrimidine, pyrazine, pyridazine), and triazine skeletons are stable and reliable, and are therefore preferred. In particular, benzofuran-pyrimidine, benzothiophene-pyrimidine, benzofuran-pyrazine, and benzothiophene-pyrazine skeletons have high acceptor activity and good reliability, and are therefore preferred. Furthermore, among the skeletons with π-electron-rich heteroaromatic rings, acridine, phenoxazine, phenothiazine, furan, thiophene, and pyrrole skeletons are stable and reliable, and are therefore preferred to have at least one of these skeletons. Moreover, dibenzofuran skeletons are preferred as furan skeletons, and dibenzothiophene skeletons are preferred as thiophene skeletons. As pyrrole skeletons, indole, carbazole, indolecarbazole, bicarbazole, and 3-(9-phenyl-9H-carbazole-3-yl)-9H-carbazole skeletons are particularly preferred. In substances where π-electron-rich and π-electron-deficient heteroaromatic rings are directly bonded, the π-electron-rich heteroaromatic ring exhibits high electron-donating and electron-accepting properties, while the energy difference between the S1 and T1 energy levels decreases, resulting in highly efficient thermally activated delayed fluorescence. Therefore, it is particularly preferred. Note that aromatic rings bonded with electron-withdrawing groups such as cyano groups can also be used instead of π-electron-deficient heteroaromatic rings. Furthermore, aromatic amine skeletons, phenazine skeletons, etc., can be used as π-electron-rich skeletons.Furthermore, as π-electron-deficient skeletons, the following can be used: oxanthracene skeleton, thioxanthene dioxide skeleton, oxadiazole skeleton, triazole skeleton, imidazole skeleton, anthraquinone skeleton, boron-containing skeletons such as phenylborane or boranthrene, aromatic rings or heteroaromatic rings with nitrile or cyanobenzene, carbonyl skeletons such as benzophenone, phosphine oxide skeleton, sulfone skeleton, etc. Thus, π-electron-deficient and π-electron-rich skeletons can be used to replace at least one of the π-electron-deficient and π-electron-rich heteroaromatic rings.
[0235] [Chemical Formula 26]
[0236]
[0237] Alternatively, TADF materials capable of very high-speed reversible intersystem crossing and emitting light according to a thermal equilibrium model between singlet and triplet excited states can also be used. Because such TADF materials have extremely short luminescence lifetimes (excitation lifetimes), efficiency degradation in the high-brightness regions of the light-emitting element can be suppressed. Specifically, materials with the following molecular structures can be cited.
[0238] [Chemical Formula 27]
[0239]
[0240] TADF materials refer to materials with a small energy difference between the S1 and T1 levels and the ability to convert triple excitation energy into single excitation energy through antisystem crossing. Therefore, they can upconvert triple excitation energy into single excitation energy (antisystem crossing) with minimal thermal energy, efficiently generating singlet excited states. Furthermore, triple excitation energy can be converted into luminescence.
[0241] Exciplexes formed by two substances in an excited state have the function of converting triple excitation energy into single excitation energy due to the extremely small difference between the S1 and T1 energy levels.
[0242] Note that the phosphorescence spectrum observed at low temperatures (e.g., 77K to 10K) can be used as an indicator of the T1 energy level. Preferably, for the TADF material, the energy of light with the extrapolated wavelength obtained by tangenting at the tail of the short-wavelength side of the fluorescence spectrum is the S1 energy level, and the energy of light with the extrapolated wavelength obtained by tangenting at the tail of the short-wavelength side of the phosphorescence spectrum is the T1 energy level, where the difference between S1 and T1 is 0.3 eV or less, more preferably 0.2 eV or less.
[0243] Furthermore, when using TADF material as the luminescent material, the S1 energy level of the host material is preferably higher than that of the TADF material. Additionally, the T1 energy level of the host material is preferably higher than that of the TADF material.
[0244] In addition, as electron transport materials for the host material, metal complexes such as bis(10-hydroxybenzo[h]quinoline) beryllium(II) (abbreviated: BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol) aluminum(III) (abbreviated: BAlq), bis(8-hydroxyquinoline) zinc(II) (abbreviated: Znq), bis[2-(2-benzoxazolyl)phenol] zinc(II) (abbreviated: ZnPBO), and bis[2-(2-benzothiazolyl)phenol] zinc(II) (abbreviated: ZnBTZ) and organic compounds with π-electron-deficient heteroaromatic rings can be used. Examples of organic compounds with π-electron-deficient heteroaromatic rings include: 2-(4-biphenyl)-5-(4-tert-butyl-phenyl)-1,3,4-oxadiazolazole (abbreviated as PBD), 3-(4-biphenyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviated as TAZ), 1,3-bis[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviated as OXD-7), and 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviated as CO11). Organic compounds containing heteroaromatic rings with an azole skeleton, such as 2,2',2''-(1,3,5-phenyltriyl)tris(1-phenyl-1H-benzimidazole) (abbreviated as: TPBI), 2-[3-(dibenzothiophene-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviated as: mDBTBIm-II); 2-[3-(dibenzothiophene-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviated as: 2mDBTPDBq-II), 2-[3'-(dibenzothiophene-4-yl)biphenyl-3-yl ... Abbreviations: 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-(dibenzothiophene-4-yl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 2,4-bis[4-(1-naphthyl)phenyl]-6-[4-(3-pyridyl)phenyl]pyrimidine (abbreviation: 2,4NP-6PyPPm) Organic compounds containing heteroaromatic rings with a diazine skeleton, such as 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)pyrimidine (abbreviated as: 6BP-4Cz2PPm), and 7-[4-(9-phenyl-9H-carbazol-2-yl)quinazolin-2-yl]-7H-dibenzo[c,g]carbazole (abbreviated as: PC-cgDBCzQz);3,5-Bis[3-(9H-carbazole-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tris[(3-pyridine)-phenyl-3-yl]benzene (abbreviation: TmPyPB), and other organic compounds containing heteroaromatic rings with a pyridine skeleton; 2-[3'-(9,9-dimethyl-9H-fluorene-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn), 2-(biphenyl-4-yl-4-phenyl-6-(9,9'-spirobis[9H-fluorene]-2-yl)-1,3,5- Triazine (abbreviation: BP-SFTzn), 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-8-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mBnfBPTzn), 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-6-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mBnfBPTzn-02), 5-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-7,7-dimethyl-5H, 7H-Indo[2,1-b]carbazole (abbreviation: mINc(II)PTzn), 2-[3'-(triphenyl-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mTpBPTzn), 3-9-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-2-dibenzofuranyl]-9-phenyl-9H-carbazole (abbreviation: PCDBfTzn), 2-(biphenyl-3-yl)-4-phenyl-6-[8-([1,1':4',1''-triphenyl]-4-yl)- Organic compounds containing a heteroaromatic ring with a triazine skeleton, such as [1-dibenzofuranyl]-1,3,5-triazine (abbreviated as mBP-TPDBfTzn). Among these, organic compounds containing a heteroaromatic ring with a diazine skeleton, a heteroaromatic ring with a pyridine skeleton, or a heteroaromatic ring with a triazine skeleton are preferred due to their good reliability. In particular, organic compounds containing a heteroaromatic ring with a diazine (pyrimidine and pyrazine) skeleton or a heteroaromatic ring with a triazine skeleton exhibit high electron transport properties, which helps to reduce the driving voltage.
[0245] As hole transport materials for use as host materials, organic compounds having an amine backbone or a π-electron-rich heteroaromatic ring can also be used. Examples of such organic compounds with an amine backbone or a π-electron-rich heteroaromatic ring include: 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminobiphenyl (TPD), N,N'-bis(9,9'-spirobis[9H-fluorene]-2-yl)-N,N'-diphenyl-4,4'-diaminobiphenyl (BSPB), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BPAFLP), and 4-phenyl-3'-(9-phenylfluorene-9-yl)triphenylamine (mBPAFL). P), 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCCNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]fluorene-2-amine (abbreviation: PCBA) F), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobis[9H-fluorene]-2-amine (abbreviated as: PCBASF), etc., compounds with aromatic amine skeletons; 1,3-bis(N-carbazolyl)benzene (abbreviated as: mCP), 4,4'-bis(N-carbazolyl)biphenyl (abbreviated as: CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviated as: CzTP), 9,9'-diphenyl-9H,9'H-3,3'-bicarbazole (abbreviated as: PCCP), etc., compounds with carbazole skeletons; 4,4',4''-(benzene-1,3,5-triyl)tris(dibenzothiophene) (abbreviated as: Compounds with a thiophene skeleton, such as DBT3P-II, 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviated as DBTFLP-III), and 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviated as DBTFLP-IV); and compounds with a furan skeleton, such as 4,4',4''-(benzene-1,3,5-triyl)tris(dibenzofuran) (abbreviated as DBF3P-II) and 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviated as mmDBFFLBi-II).Compounds with an aromatic amine backbone or a carbazole backbone are preferred due to their high reliability, excellent hole transport properties, and ability to reduce driving voltage. Alternatively, organic compounds with hole transport properties, exemplified as materials for hole transport layer 112, can also be used as the host hole transport material.
[0246] By mixing electron transport materials and hole transport materials, it is easier to adjust the transport properties of the light-emitting layer 113 and to control the recombination region more easily. Furthermore, TADF materials can also be used as either electron transport materials or hole transport materials.
[0247] As a TADF material that can be used as the host material, the same materials mentioned above as TADF materials can be used. When a TADF material is used as the host material, the triple excitation energy generated by the TADF material is converted into a single excitation energy through antisystem crossing and further transferred to the luminescent material, thereby improving the luminous efficiency of the light-emitting device. In this case, the TADF material is used as an energy donor, and the luminescent material is used as an energy acceptor.
[0248] This is highly effective when the luminescent material is a fluorescent luminescent material. Furthermore, to obtain high luminescent efficiency, the S1 energy level of the TADF material is preferably higher than the S1 energy level of the fluorescent luminescent material. Additionally, the T1 energy level of the TADF material is preferably higher than the S1 energy level of the fluorescent luminescent material. Therefore, the T1 energy level of the TADF material is preferably higher than the T1 energy level of the fluorescent luminescent material.
[0249] Furthermore, it is preferable to use a TADF material that exhibits luminescence with a wavelength overlapping the absorption band on the lowest energy side of the fluorescent luminescent material. This allows for efficient transfer of excitation energy from the TADF material to the fluorescent luminescent material, resulting in highly efficient luminescence, and is therefore preferred.
[0250] To efficiently generate a singlet excitation energy from a triplet excitation energy via antisystem crossing, it is preferable to induce carrier recombination within the TADF material. Furthermore, it is preferable that the triplet excitation energy generated in the TADF material does not transfer to the triplet excitation energy of the fluorescent luminescent material. For this purpose, the fluorescent luminescent material preferably has a protecting group surrounding the luminescent body (the backbone that causes luminescence) of the fluorescent luminescent material. This protecting group is preferably a substituent without π bonds, preferably a saturated hydrocarbon; specifically, examples include alkyl groups with 3 or more but less than 10 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 or more but less than 10 carbon atoms, and trialkylsilyl groups with 3 or more but less than 10 carbon atoms; more preferably, multiple protecting groups are preferred. Substituents without π bonds have almost no function in transporting charge carriers, thus having little effect on charge carrier transport and recombination, allowing the TADF material and the luminescent body of the fluorescent luminescent material to be kept apart. Here, the luminescent body refers to the atomic group (backbone) in the fluorescent luminescent material that causes luminescence. The luminescent material preferably has a π-bonded framework, preferably including an aromatic ring, and even more preferably including a fused aromatic ring or a fused heteroaromatic ring. Examples of such luminescent materials include phenanthrene, stilbene, acridinone, phenoxazine, phenothiazine, naphthalene, anthracene, fluorene, β-carbamate, triphenylene, tetraphenylene, pyrene, perylene, coumarin, quinacridone, and naphthobisbenzofuran frameworks. In particular, fluorescent luminescent materials having naphthalene, anthracene, fluorene, β-carbamate, triphenylene, tetraphenylene, pyrene, perylene, coumarin, quinacridone, and naphthobisbenzofuran frameworks exhibit high fluorescence quantum yields and are therefore preferred.
[0251] When using a fluorescent luminescent material as the luminescent material, a material with an anthracene framework is preferably used as the host material. By using a material with an anthracene framework as the host material of the fluorescent luminescent material, a luminescent layer with both high luminous efficiency and durability can be achieved. Among the anthracene framework materials used as host materials, those with a diphenylanthracene framework, especially a 9,10-diphenylanthracene framework, are chemically stable and therefore preferred. Furthermore, when the host material has a carbazole framework, hole injection / transport is improved, which is also preferred. However, when the host material has a benzo[a]carbazole framework with a benzene ring also fused to the carbazole framework, the HOMO is about 0.1 eV shallower than that of a host material with a carbazole framework, making hole injection easier and therefore more preferable. In particular, when the host material has a dibenzo[a]carbazole framework, its HOMO is about 0.1 eV shallower than that of a host material with a carbazole framework, which not only facilitates hole injection but also improves hole transport and heat resistance, making it preferred. Therefore, a further preferred material for use as the host material is one having a 9,10-diphenylanthracene skeleton and a carbazole skeleton (or a benzo[a]carbazole skeleton or a dibenzo[a]carbazole skeleton). Note that from the viewpoint of hole injection / transportation described above, a benzo[a]fluorene skeleton or a dibenzo[a]fluorene skeleton can also be used instead of a carbazole skeleton. Examples of such substances include 9-phenyl-3-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (abbreviated: PCzPA), 3-[4-(1-naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviated: PCPN), 9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (abbreviated: CzPA), 7-[4-(10-phenyl-9-anthrayl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviated: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthrayl)phenyl]benzo[b]naphtho[1,2-d]furan (abbreviated: 2mBnfPPA), 9-phenyl-1 0-[4'-(9-phenyl-9H-fluorene-9-yl)biphenyl-4-yl]anthracene (abbreviation: FLPPA), 9-(1-naphthyl)-10-(2-naphthyl)anthracene (abbreviation: α,βADN), 2-(10-phenylanthracene-9-yl)dibenzofuran, 2-(10-phenyl-9-anthrayl)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-anthrayl]phenyl}-2-ethyl-1H-benzimidazole (abbreviation: EtBImPBPhA), etc. In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA exhibit very good properties and are therefore preferred.
[0252] Note that phosphorescent materials can be used as part of the above-described mixture. When phosphorescent materials are used as fluorescent materials, they can be used as energy donors to supply excitation energy to the fluorescent materials.
[0253] Alternatively, the aforementioned mixed materials can be used to form an excimer complex. By selecting a combination of excimer complexes that emit light with wavelengths overlapping the absorption band on the lowest energy side of the luminescent material, energy transfer can be facilitated, resulting in efficient luminescence, which is therefore preferred. Furthermore, this structure reduces the driving voltage, making it also preferred.
[0254] Note that at least one of the materials forming the excitocomplex can be a phosphorescent material. This allows for the efficient conversion of triple excitation energy into single excitation energy via antisystem crossing.
[0255] Regarding the combination of materials for efficiently forming excitocomplexes, the HOMO energy level of the material with hole transport is preferably above the HOMO energy level of the material with electron transport. Furthermore, the LUMO energy level of the material with hole transport is preferably above the LUMO energy level of the material with electron transport. Note that the LUMO and HOMO energy levels of the material can be determined from the electrochemical properties (reduction potential and oxidation potential) of the material measured by cyclic voltammetry (CV).
[0256] Note that the formation of excitocomplexes can be confirmed, for example, by comparing the emission spectra of a hole-transporting material, the emission spectra of an electron-transporting material, and the emission spectra of a hybrid film formed by mixing these materials. When the emission spectrum of the hybrid film is observed to shift towards a longer wavelength (or to have a new peak on the longer wavelength side) compared to the emission spectra of each material, it indicates the formation of an excitocomplex. Alternatively, by comparing the transient photoluminescence (PL) of a hole-transporting material, the transient PL of an electron-transporting material, and the transient PL of a hybrid film formed by mixing these materials, when a difference in transient response is observed, such as a longer lifetime component or a larger proportion of delayed components compared to the transient PL lifetimes of each material, it indicates the formation of an excitocomplex. Furthermore, the aforementioned transient PL can be referred to as transient electroluminescence (EL). In other words, by comparing the transient EL of a hole-transporting material, the transient EL of an electron-transporting material, and the transient EL of a hybrid film of these materials, and observing the differences in transient responses, the formation of an excitocomplex can be confirmed.
[0257] Furthermore, the light-emitting layer 113 can be formed using methods such as vapor deposition (including vacuum vapor deposition), inkjet printing, coating, and gravure printing. In addition to the materials mentioned above, it may also contain inorganic compounds such as quantum dots or polymeric compounds (oligomers, dendritic polymers, polymers, etc.).
[0258] <<Hollow Injection Layer>>
[0259] The hole injection layer (111, 111a, 111b) is a layer in which holes are injected from the first electrode 101 of the anode and the charge generation layer (106, 106a, 106b) into the organic compound layer (103, 103a, 103b), and is a layer containing organic acceptor material and material with high hole injection capability.
[0260] Compounds with electron-withdrawing groups (halogen or cyano groups) can be used as hole injection layers (111, 111a, 111b). Examples include 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinone dimethyl ether (F4-TCNQ), chloroquinone, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN), 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (F6-TCNNQ), and 2-(7-dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyrene-2-yl)malononitrile. In particular, compounds such as HAT-CN, which have electron-withdrawing groups bonded to fused aromatic rings with multiple heteroatoms, are thermally stable and therefore preferred. Furthermore, [3] axylene derivatives including electron-withdrawing groups (especially halogen groups such as fluorine groups or cyano groups) are particularly preferred due to their high electron acceptability. Specifically, examples include: α,α',α''-1,2,3-cyclopropanetrimethylenetri(4-cyano-2,3,5,6-tetrafluorophenylacetonitrile) (abbreviated as Rad), α,α',α''-1,2,3-cyclopropanetrimethylenetri[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)phenylacetonitrile], α,α',α''-1,2,3-cyclopropanetrimethylenetri[2,3,4,5,6-pentafluorophenylacetonitrile], etc. In addition to the aforementioned organic compounds, molybdenum oxides, vanadium oxides, ruthenium oxides, tungsten oxides, manganese oxides, etc., can be used as acceptor substances. In addition, phthalocyanine complexes such as phthalocyanine (H2Pc) and copper phthalocyanine (CuPc) can be used; aromatic amine compounds such as 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB) and N,N'-bis[4-bis(3-methylphenyl)aminophenyl]-N,N'-diphenyl-4,4'-diaminobiphenyl (DNTPD); or polymers such as poly(3,4-ethylenedioxythiophene) / polystyrene sulfonic acid (PEDOT / PSS) can be used to form hole injection layers (111, 111a, 111b). Substances with acceptor properties can extract electrons from adjacent hole transport layers (or hole transport materials) by means of an applied electric field.
[0261] Furthermore, in substances with receptors, organic compounds with receptors can be easily deposited using vapor deposition, making them easy-to-use materials.
[0262] Furthermore, as the hole injection layer (111, 111a, 111b), a composite material containing the aforementioned acceptor substance in a material with hole transport properties can be used. Note that by using a composite material containing an acceptor substance in a material with hole transport properties, the work function does not need to be considered when selecting the material to form the electrode. In other words, as the anode (first electrode 101), not only materials with high work functions but also materials with low work functions can be used.
[0263] Various organic compounds, such as aromatic amine compounds, carbazole derivatives, aromatic hydrocarbons, and polymers (oligomers, dendritic polymers, polymers, etc.), can be used as hole-transporting materials for composite materials. Preferably, a hole mobility of 1×10⁻⁶ is used. -6 cm 2 Substances with a density of / Vs or higher. Below, specific examples of organic compounds with hole transport properties that can be used in composite materials are listed.
[0264] Examples of aromatic amine compounds that can be used in composite materials include N,N'-bis(p-tolyl)-N,N'-diphenyl-p-phenylene diamine (DTDPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), N,N'-bis-[4-bis(3-methylphenyl)aminophenyl]-N,N'-diphenyl-4,4'-diaminobiphenyl (DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (DPA3B). Specific examples of carbazole derivatives include 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviated as PCzPCN1), 4,4'-bis(N-carbazole)biphenyl (abbreviated as CBP), 1,3,5-tris[4-(N-carbazole)phenyl]benzene (abbreviated as TCPB), 9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (abbreviated as CzPA), and 1,4-bis[4-(N-carbazole)phenyl]-2,3,5,6-tetraphenylbenzene, etc. Examples of aromatic hydrocarbons include 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (t-BuDNA), 2-tert-butyl-9,10-bis(1-naphthyl)anthracene, 9,10-bis(3,5-diphenylphenyl)anthracene (DPPA), 2-tert-butyl-9,10-bis(4-phenylphenyl)anthracene (t-BuDBA), 9,10-bis(2-naphthyl)anthracene (DNA), 9,10-diphenylanthracene (DPAnth), 2-tert-butylanthracene (t-BuAnth), and 9,10-bis(4-methyl-1-naphthyl)anthracene (DMNA). Examples of anthracene compounds include 2-tert-butyl-9,10-bis[2-(1-naphthyl)phenyl]anthracene, 9,10-bis[2-(1-naphthyl)phenyl]anthracene, 2,3,6,7-tetramethyl-9,10-bis(1-naphthyl)anthracene, 2,3,6,7-tetramethyl-9,10-bis(2-naphthyl)anthracene, 9,9'-bianthracene, 10,10'-diphenyl-9,9'-bianthracene, 10,10'-bis(2-phenylphenyl)-9,9'-bianthracene, 10,10'-bis[(2,3,4,5,6-pentaphenyl)phenyl]-9,9'-bianthracene, anthracene, tetraphenylene, rubrogene, perylene, and 2,5,8,11-tetra(tert-butyl)perylene. Additionally, pentaphenylene and phenazine can also be used. Furthermore, a vinyl backbone can also be present.Examples of aromatic hydrocarbons containing vinyl groups include 4,4'-bis(2,2-diphenylvinyl)biphenyl (abbreviated as DVBBi) and 9,10-bis[4-(2,2-diphenylvinyl)phenyl]anthracene (abbreviated as DPVPA). Furthermore, organic compounds of one aspect of the present invention may also be used.
[0265] In addition, polymers such as poly(N-vinylcarbazole) (PVK), poly(4-vinyltriphenylamine) (PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (Poly-TPD) can also be used.
[0266] As a hole-transporting material for use in composite materials, it is more preferable to have at least one of a carbazole backbone, a dibenzofuran backbone, a dibenzothiophene backbone, and an anthracene backbone. In particular, it can be an aromatic amine having substituents including a dibenzofuran ring or a dibenzothiophene ring, an aromatic monoamine including a naphthyl ring, or an aromatic monoamine in which a 9-fluorene group is bonded to the nitrogen of the amine via an arylene group. Note that when these organic compounds are substances including N,N-bis(4-biphenyl)amino groups, long-lifetime light-emitting devices can be manufactured, and therefore are preferred. Specifically, examples of the aforementioned organic compounds include N-(4-biphenyl)-6,N-diphenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviated as: BnfABP), N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviated as: BBABnf), 4,4'-bis(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)-4''-phenyltriphenylamine (abbreviated as: BnfBB1BP), and N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-8-amine (abbreviated as: BBABnf), -d]furan-6-amine (abbreviation: BBABnf(6)), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf(8)), N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviation: BBABnf(II)(4)), N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP), N-[4-(dibenzothiophen-4-yl)phenyl]-N-phenyl-4- Biphenylamine (abbreviated as: ThBA1BP), 4-(2-naphthyl)-4',4''-diphenyltriphenylamine (abbreviated as: BBAβNB), 4-[4-(2-naphthyl)phenyl]-4',4''-diphenyltriphenylamine (abbreviated as: BBAβNBi), 4,4'-diphenyl-4''-([2,1'-binathyl]-6-yl)triphenylamine (abbreviated as: BBAαNβNB), 4,4'-diphenyl-4''-([2,1'-binathyl]-7-yl)triphenylamine (abbreviated as: BBAαNβNB-03), 4,4'-diphenyl -4''-(7-phenyl)naphthyl-2-yltriphenylamine (abbreviation: BBAPβNB-03), 4,4'-diphenyl-4''-([2,2'-binaphthyl]-6-yl)triphenylamine (abbreviation: BBA(βN2)B), 4,4'-diphenyl-4''-([2,2'-binaphthyl]-7-yl)triphenylamine (abbreviation: BBA(βN2)B-03), 4,4'-diphenyl-4''-([1,2'-binaphthyl]-4-yl)triphenylamine (abbreviation: BBAβNαNB ...([1,2'-binaphthyl]-4-yl)triphenylamine (abbreviation: BBAβNαNB), 4,4'-diphenyl-4''-([1,2'-binaphthyl]-([1,2'-Binaphthyl]-5-yl)triphenylamine (abbreviation: BBAβNαNB-02), 4-(4-biphenyl)-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: TPBiAβNB), 4-(3-biphenyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: mTPBiAβNBi), 4-(4-biphenyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: TPBiAβNBi), 4-phenyl-4'-(1-naphthyl)triphenylamine (abbreviation: αNBA1BP), 4,4'-bis(1-naphthyl)triphenylamine (abbreviation: αNBB1BP), 4,4'-diphenyl 4''-[4'-(carbazole-9-yl)biphenyl-4-yl]triphenylamine (abbreviation: YGTBi1BP), 4'-[4-(3-phenyl-9H-carbazole-9-yl)phenyl]tri(biphenyl-4-yl)amine (abbreviation: YGTBi1BP-02), 4-[4'-(carbazole-9-yl)biphenyl-4-yl]-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: YGTBiβNB), N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-N-[4-(1-naphthyl)phenyl]-9,9'-spirodi[9H-fluorene]-2-amine (abbreviation: PCBNBSF), N,N-bis(biphenyl-4-yl)-9,9'- Spirodi[9H-fluorene]-2-amine (abbreviated as BBASF), N,N-bis(biphenyl-4-yl)-9,9'-spirodi[9H-fluorene]-4-amine (abbreviated as BBASF(4)), N-(biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirodi[9H-fluorene]-4-amine (abbreviated as oFBiSF), N-(biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl)dibenzofuran-4-amine (abbreviated as FrBiF), N-[4-(1-naphthyl)phenyl]-N-[3-(6-phenyldibenzofuran-4-yl)phenyl]-1-naphthylamine (abbreviated as mPDBfBNBN) 4-Phenylacetyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviation: BPAFLP), 4-Phenylacetyl-3'-(9-phenylfluorene-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-Phenylacetyl-4'-[4-(9-phenylfluorene-9-yl)phenyl]triphenylamine (abbreviation: BPAFLBi), 4-Phenylacetyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-Di(1-naphthyl)-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as: PCCNBB), N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9'-spirodi[9H-fluorene]-2-amine (abbreviated as: PCBASF), N-(biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H-fluorene-2-amine (abbreviated as: PCBBi) F), N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirodi-9H-fluoren-4-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirodi-9H-fluoren-3-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirodi-9H-fluoren-2-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirodi-9H-fluoren-1-amine, etc.
[0267] Note that the hole-transporting material used in the composite material is more preferably a material with a deep HOMO energy level, having a HOMO energy level of -5.7 eV or higher and -5.4 eV or lower. When the hole-transporting material used in the composite material has a deep HOMO energy level, holes are easily injected into the hole transport layer 112, and a long-lifetime light-emitting device can be easily obtained. Furthermore, when the hole-transporting material used in the composite material is a material with a deep HOMO energy level, hole induction is appropriately suppressed, thus enabling a light-emitting device with an even longer lifetime.
[0268] Note that by further mixing alkali metal or alkaline earth metal fluorides into the above-mentioned composite material (preferably, the atomic ratio of fluorine atoms in the layer is 20% or more), the refractive index of the layer can be reduced. Therefore, a layer with a low refractive index can be formed inside the organic compound layer 103, and the external quantum efficiency of the light-emitting device can be improved.
[0269] By forming hole injection layers (111, 111a, 111b), hole injection capability can be improved, thereby obtaining light-emitting devices with low driving voltage.
[0270] <<Hole Transport Layer>>
[0271] The hole transport layers (112, 112a, 112b) are layers containing hole transport materials, and hole transport materials exemplified as those used in 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 emitting layers (113, 113a, 113b), so it is preferable that they have HOMO energy levels that are the same as or close to the HOMO energy levels of the hole injection layers (111, 111a, 111b).
[0272] Furthermore, the aforementioned hole transport material is preferably 1×10 -6 cm 2 Materials with a hole mobility of / Vs or higher. However, any material other than those described above can be used as long as its hole transport capacity is higher than its electron transport capacity. Furthermore, the layer including the material with high hole transport capacity is not limited to a single layer, but can also be a layer composed of two or more layers of the above-mentioned materials.
[0273] Examples of materials that can be used in hole transport layers (112, 112a, 112b) include: 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminobiphenyl (TPD), N,N'-bis(9,9'-spirobis[9H-fluorene]-2-yl)-N,N'-diphenyl-4,4'-diaminobiphenyl (BSPB), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BPAFLP), 4-phenyl-3'-(9-phenylfluorene-9-yl)triphenylamine (mBPAFLP), 4- Phenylacetyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCCNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]fluorene-2-amine (abbreviation: PCBAF), N-phenyl-N-[4- Compounds with aromatic amine skeletons, such as [9-phenyl-9H-carbazole-3-yl]phenyl-9,9'-spirodi[9H-fluorene]-2-amine (abbreviated as: PCBASF); 1,3-bis(N-carbazole)benzene (abbreviated as: mCP), 4,4'-bis(N-carbazole)biphenyl (abbreviated as: CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviated as: CzTP), 9,9'-diphenyl-9H,9'H-3,3'-bicarbazole (abbreviated as: PCCP), 9,9'-bis(biphenyl-4-yl)-3,3'-bi-9H-carbazole (abbreviated as: BisBPCz), 9,9'-bis(biphenyl-3-yl)-3,3'-bi Compounds with a carbazole skeleton, such as -9H-carbazole (abbreviated as: BismBPCz), 9-(biphenyl-3-yl)-9'-(biphenyl-4-yl)-9H,9'H-3,3'-bicarbazole (abbreviated as: mBPCCBP); and compounds with a thiophene skeleton, such as 4,4',4''-(benzyl-1,3,5-triyl)tris(dibenzothiophene) (abbreviated as: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluorene-9-yl)phenyl]dibenzothiophene (abbreviated as: DBTFLP-III), and 4-[4-(9-phenyl-9H-fluorene-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviated as: DBTFLP-IV);Compounds with a furan skeleton, such as 4,4',4''-(benzyl-1,3,5-triyl)tris(dibenzofuran) (abbreviated as DBF3P-II) and 4-{3-[3-(9-phenyl-9H-fluorene-9-yl)phenyl]phenyl}dibenzofuran (abbreviated as mmDBFFLBi-II), are preferred. Compounds with an aromatic amine skeleton or a carbazole skeleton are preferred due to their high reliability, excellent hole transport properties, and ability to reduce driving voltage. Note that materials with hole transport properties, such as those used in the composite material for the hole injection layer 111, can also be appropriately used as materials constituting the hole transport layer 112.
[0274] <<Electron Transport Layer>>
[0275] The electron transport layers (114, 114a, 114b) have the function of transporting electrons injected from the other of the pair of electrodes (first electrode 101 or second electrode 102) through the electron injection layers (115, 115a, 115b) to the light-emitting layer 113. Alternatively, the organic compound described in Embodiment 1 can also be used as the electron transport layer.
[0276] The preferred electron transport material is an organic compound with electron transport properties, wherein the electron mobility is 1×10⁻⁶ when the square root of the electric field strength [V / cm] is 600. -6 cm 2 / Vs or higher. Furthermore, any substance other than those described above can be used, as long as its electron transport capability is higher than its hole transport capability. As the aforementioned organic compound, an organic compound comprising a π-electron-deficient heteroaromatic ring is preferred. For example, one or more of the following are preferred: organic compounds comprising a heteroaromatic ring with an azole skeleton, organic compounds comprising a heteroaromatic ring with a pyridine skeleton, organic compounds comprising a heteroaromatic ring with a diazine skeleton, and organic compounds comprising a heteroaromatic ring with a triazine skeleton.
[0277] Organic compounds with π-electron-deficient heteroaromatic rings that can be used in the aforementioned electron transport layers include, specifically, 2-(4-biphenyl)-5-(4-tert-butyl-phenyl)-1,3,4-oxadiazole (abbreviated as PBD), 3-(4-biphenyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviated as TAZ), 1,3-bis[5-(4-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]phenyl (abbreviated as OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazole-2-yl)phenyl]-9H-carbazole (abbreviated as CO11), and 2,2',2''-(1,3,5-phenyltriyl)tris(1-phenyl-1H-benzimidazole). Organic compounds with an azole skeleton, such as TPBI, 2-[3-(dibenzothiophene-4-yl)phenyl]-1-phenyl-1H-benzimidazole (mDBTBIm-II), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (BzOs); and 3,5-bis[3-(9H-carbazole-9-yl)phenyl]pyridine (35DCzPPy), 1,3,5-tris[(3-pyridyl)phenyl-3-yl]benzene (TmPyPB), phenanthroline (Bphen), copper hydroxide (BCP), and 2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), etc. Organic compounds with heteroaromatic rings and pyridine skeletons; 2-[3-(dibenzothiophene-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothiophene-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-carbazole-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPDBq-II), 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II), 9-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]furano[2,3-b]pyrazine (abbreviation: 9mDBtBPNfpr), 9-[3'-(dibenzothiophen-4-yl)biphenyl-4-yl]naphtho[1',2':4,5]furano[2,3-b]pyrazine (abbreviation: 9pmDBtBPNfpr), 4,6-bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(dibenzothiophene-4-yl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazole-9-yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), 9,9'-[pyrimidine-4,6-diylbis(biphenyl-3,3'-diyl)]bis(9H-carbazole) (abbreviation: 4,6mCzBP2Pm), 8-(biphenyl-4-yl)-4-[3-(dibenzothiophene-4-yl)phenyl]-[1]benzofuran[3,2-d]pyrimidine (Abbreviation: 8BP-4mDBtPBfpm), 3,8-bis[3-(dibenzothiophen-4-yl)phenyl]benzofurano[2,3-b]pyrazine (Abbreviation: 3,8mDBtP2Bfpr), 8-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]furano[3,2-d]pyrimidine (Abbreviation: 8mDBtBPNfpm), 8-([2,2'-binaphthyl]-6-yl)-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofurano[3,2-d]pyrimidine (Abbreviation: 8(βN2)-4mDBtPBfpm), 2,2'-(pyridin-2,6-diyl)bis(4-phenylbenzo[h]quinoline) 2,6(P-Bqn)2Py (abbreviated as: 2,6(P-Bqn)2Py), 2,2'-(pyridin-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-carbazole-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-carbazole-9-yl)phenyl]-2-phenyl-6-(biphenyl-4-yl)pyrimidine (abbreviated as: 6BP-4Cz2P) Organic compounds with a diazine skeleton, such as Pm), 7-[4-(9-phenyl-9H-carbazol-2-yl)quinazolin-2-yl]-7H-dibenzo[c,g]carbazole (abbreviation: PC-cgDBCzQz); 2-[3'-(9,9-dimethyl-9H-fluorene-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn), 2-(biphenyl-4-yl)-4-phenyl-6-(9,9'-spirobis[9H-fluorene]-2-yl)-1,3,5-triazine (abbreviation: BP-SFTzn), 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-8-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-Triazine (abbreviation: mBnfBPTzn), 2-{3-[3-(benzo[b]naphtho[1,2-d]furan-6-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mBnfBPTzn-02), 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 (abbreviation: mPCCzPTzn-02), 5-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-7,7-dimethyl-5H,7H-indo[2,1-b]carbazole (abbreviation: mINc(II)PTzn), 2-{3-[3-(dibenzothiophene-4-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mDBtBPTzn), 2,4,6-tris[3'-(pyridin-3-yl)biphenyl-3-yl]-1, 3,5-Triazine (abbreviation: TmPPPyTz), 2-[3-(2,6-dimethyl-3-pyridyl)-5-(9-phenanthyl)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'-(triphenyl-2-yl)biphenyl-3- Organic compounds with a triazine skeleton, such as [9-(4,6-diphenyl-1,3,5-triazine-2-yl)-2-dibenzofuranyl]-9-phenyl-9H-carbazole (abbreviated as PCDBfTzn), and 2-(biphenyl-3-yl)-4-phenyl-6-[8-([1,1':4',1''-triphenyl]-4-yl)-1-dibenzofuranyl]-1,3,5-triazine (abbreviated as mBP-TPDBfTzn), are preferred. Among these, organic compounds containing a heteroaromatic ring with a diazine skeleton, organic compounds containing a heteroaromatic ring with a pyridine skeleton, or organic compounds containing a heteroaromatic ring with a triazine skeleton exhibit good reliability and are therefore preferred. In particular, organic compounds containing heteroaromatic rings with diazine (pyrimidine and pyrazine) skeletons and organic compounds containing heteroaromatic rings with triazine skeletons exhibit high electron transport properties, which helps to reduce the driving voltage.
[0278] Furthermore, the electron transport layers (114, 114a, 114b) are not limited to a single layer, but can also be two or more layers composed of the above-mentioned materials.
[0279] Furthermore, a layer for controlling the movement of electron carriers can be placed between the electron transport layer (114, 114a, 114b) and the light-emitting layer (113, 113a, 113b). This layer is formed by adding a small amount of a substance with high electron trapping properties to the aforementioned material with high electron transport properties. By suppressing the movement of electron carriers, the balance of carriers can be adjusted. This structure is very effective in suppressing problems caused by electrons passing through the light-emitting layer (such as a decrease in device lifetime).
[0280] <<Electron Injection Layer>>
[0281] The electron injection layers (115, 115a, 115b) have the function of lowering the injection barrier of electrons from the second electrode 102 and promoting electron injection. Alternatively, the organic compound described in Embodiment 1 can also be used as the electron injection layer.
[0282] For example, Group 1 metals, Group 2 metals, or their oxides, halides, carbonates, etc., can be used. Furthermore, composite materials of the aforementioned electron transport materials and materials possessing electron-donating properties can also be used. Examples of materials possessing electron-donating properties include Group 1 metals, Group 2 metals, or their oxides. Specifically, lithium fluoride (LiF), sodium fluoride (NaF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium oxide (LiO) can be used. x Alkali metals, alkaline earth metals, or compounds of these metals can be used. Additionally, rare earth metal compounds such as erbium fluoride (ErF3) can be used. Furthermore, electron salts can be used in the electron injection layer 115. Examples of such electron salts include substances that add electrons at high concentrations to a mixed oxide of calcium and aluminum. Additionally, substances suitable for electron transport layers (114, 114a, 114b) can be used in the electron injection layers (115, 115a, 115b).
[0283] Alternatively, composite materials formed by mixing organic compounds with electron donors can be used for electron injection layers (115, 115a, 115b). These composite materials exhibit good electron injection and electron transport properties because electrons are generated in the organic compound through electron donors. In this case, the organic compound is preferably a material with good performance in transporting the generated electrons; specifically, for example, the substances constituting the electron transport layer 114 as described above (metal complexes or heteroaromatic compounds, etc.) can be used. As the electron donor, any substance that provides electrons to the organic compound is acceptable. Specifically, alkali metals, alkaline earth metals, or rare earth metals are preferred, such as lithium, sodium, cesium, magnesium, calcium, erbium, and ytterbium. Furthermore, alkali metal oxides or alkaline earth metal oxides are preferred, such as lithium oxides, calcium oxides, and barium oxides. Additionally, Lewis bases such as magnesium oxide can also be used. Furthermore, organic compounds such as tetrathiofulvalene (TTF) can also be used.
[0284] Furthermore, the aforementioned light-emitting layer, hole injection layer, hole transport layer, electron transport layer, and electron injection layer can all be formed by methods such as vapor deposition (including vacuum vapor deposition), inkjet printing, coating, and gravure printing. In addition to the materials mentioned above, inorganic compounds such as quantum dots or polymeric compounds (oligomers, dendritic polymers, polymers, etc.) can also be used as the aforementioned light-emitting layer, hole injection layer, hole transport layer, electron transport layer, and electron injection layer.
[0285] As quantum dots, various types can be used, including colloidal quantum dots, alloy quantum dots, core-shell quantum dots, and nucleated quantum dots. Additionally, quantum dots containing elements from Groups 2 and 16, 13 and 15, 13 and 17, 11 and 17, or 14 and 15 can also be used. Alternatively, 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) can be used.
[0286] <>
[0287] The first electrode 101 and the second electrode 102 are used as the anode or cathode of the light-emitting device. The first electrode 101 and the second electrode 102 can be formed using metals, alloys, conductive compounds, mixtures thereof, or laminates thereof.
[0288] One of the first electrode 101 and the second electrode 102 is preferably formed of a conductive material that has the function of reflecting light. Examples of such conductive material include aluminum (Al) or 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 alloys containing Al, Ni, and La. Aluminum has low resistivity and high light reflectivity. In addition, since aluminum is abundant in the earth's crust and inexpensive, using aluminum can reduce the manufacturing cost of the light-emitting device. Alternatively, silver (Ag) or alloys 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), and gold (Au)) can also be used. Examples of silver-containing alloys 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. In addition to the above materials, transition metals such as tungsten, chromium (Cr), molybdenum (Mo), copper, and titanium can be used.
[0289] Furthermore, light obtained 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 of a conductive material that allows light to pass through. Examples of such conductive material include 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 × 10⁻⁶. -2 Ω Conductive materials with a diameter of less than 1 cm.
[0290] Furthermore, the first electrode 101 and the second electrode 102 may also be formed of a conductive material that has the function of allowing light to pass through and reflecting light. Examples of such conductive materials include those with a visible light reflectance of 20% or more and 80% or less, preferably 40% or more and 70% or less, and a resistivity of 1×10⁻⁶. -2 Ω Conductive materials with a thickness of less than 1 cm can be used. For example, one or more of conductive metals, alloys, and conductive compounds can be used. Specifically, indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide (ITSO), indium zinc oxide, indium tin oxide containing titanium, indium titanium oxide, and indium oxide containing tungsten oxide and zinc oxide are examples of such metal oxides. Furthermore, metal films with a thickness of at least 1 nm and less than 30 nm that allows light to pass through can be used. Ag can be used as a metal, for example. Alloys such as those of Ag and Al, Ag and Mg, Ag and Au, and Ag and Yb can also be used.
[0291] Note that in this specification, materials that are transparent to light can be made of materials that are both conductive and allow visible light to pass through. Examples include oxide conductors such as ITO (Indium Tin Oxide), oxide semiconductors, or organic conductors containing organic matter. Examples of organic conductors containing organic matter include composite materials comprising a mixture of organic compounds and an electron donor, and composite materials comprising a mixture of organic compounds and an electron acceptor. Inorganic carbon materials such as graphene can also be used. Furthermore, the resistivity of this material is preferably 1 × 10⁻⁶. 5 Ω Below cm, preferably 1×10 4 Ω Less than cm.
[0292] Furthermore, one or both of the first electrode 101 and the second electrode 102 can be formed by stacking multiple of the above-mentioned materials.
[0293] To improve light extraction efficiency, a material with a higher refractive index than an electrode that allows light to pass through can be formed in contact with the electrode. This material can be either conductive or non-conductive, as long as it allows visible light to pass through. Examples include oxide semiconductors and organic materials, in addition to the aforementioned oxide conductors. Examples of organic materials include those exemplified as light-emitting layers, hole injection layers, hole transport layers, electron transport layers, or electron injection layers. Furthermore, inorganic carbon materials or metal thin films with a thickness sufficient to allow light to pass through can also be used, and multiple layers with thicknesses ranging from several nm to tens of nm can be stacked.
[0294] When the first electrode 101 or the second electrode 102 is used as a cathode, a material with a low work function (below 3.8 eV) is preferably used. For example, elements belonging to Group 1 or Group 2 of the periodic table (e.g., alkali metals such as lithium, sodium, and cesium, alkaline earth metals such as calcium or strontium, magnesium, etc.), alloys containing the above elements (e.g., Ag and Mg or Al and Li), rare earth metals such as europium (Eu) or Yb, alloys containing the above rare earth metals, alloys containing aluminum, silver, etc., can be used.
[0295] When the first electrode 101 or the second electrode 102 is used as the anode, a material with a large work function (above 4.0 eV) is preferably used.
[0296] The first electrode 101 and the second electrode 102 can also be a laminate of conductive materials that reflect light and conductive materials that allow light to pass through. In this case, the first electrode 101 and the second electrode 102 have the function of adjusting the optical distance so that the light of the desired wavelength from each light-emitting layer resonates and enhances its wavelength, which is preferred.
[0297] As for the film formation methods of the first electrode 101 and the second electrode 102, sputtering, vapor deposition, printing, coating, MBE (Molecular Beam Epitaxy), CVD, pulsed laser deposition, ALD (Atomic Layer Deposition), etc. can be appropriately used.
[0298] <<Charge Generation Layer (Intermediate Layer)>>
[0299] The charge generation layer 106 functions to inject electrons into the organic compound layer 103a and holes into the organic compound layer 103b when a voltage is applied between the first electrode 101 (anode) and the second electrode 102 (cathode). The charge generation layer 106 can have a structure that adds electron acceptors to the hole-carrying material (also called a p-type layer) or a structure that adds electron donors to the electron-carrying material (also called an electron injection buffer layer). Alternatively, both structures can be stacked. Furthermore, an electron relay layer can be provided between the p-type layer and the electron injection buffer layer.
[0300] When the charge generation layer 106 has a structure (p-type layer) that adds an electron acceptor to the hole transport material of the organic compound, the hole transport material shown in this embodiment can be used as the hole transport material. Furthermore, examples of electron acceptors include 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinone dimethane (abbreviated as F4-TCNQ) and chloroquinone. Additionally, oxides of metals belonging to Groups 4 to 8 of the periodic table can be used. Specifically, examples include vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide. The aforementioned acceptor materials can also be used. Furthermore, a hybrid film formed by mixing the materials constituting the p-type layer can be used, or a single film containing each material can be stacked.
[0301] When the charge generation layer 106 has a structure that adds an electron donor to the electron transport material (electron injection buffer layer), the organic compound described in Embodiment 1 is preferably used as the electron transport material. Alternatively, the electron transport material shown in this embodiment may also be used.
[0302] Furthermore, by using an organic compound of one aspect of the present invention to form an electron injection buffer layer, the rise in driving voltage that occurs when stacking organic compound layers including a light-emitting layer can be suppressed. For example, when a layer formed by mixing a metal or metal compound with an organic compound of one aspect of the present invention is used as an electron injection buffer layer, the nitrogen atoms included in the organic compound of one aspect of the present invention can form coordination bonds with the metal or metal compound (forming a chelate complex). Thus, when the organic compound of one aspect of the present invention is mixed with a metal or metal compound, it can be stabilized using a metal or metal compound that acts as an electron donor. In other words, when the organic compound of one aspect of the present invention is used as an intermediate layer or electron transport layer in a tandem light-emitting device, a light-emitting device capable of being driven at a low voltage can be provided.
[0303] Furthermore, alkali metals, alkaline earth metals, rare earth metals, or metals belonging to Groups 2 and 13 of the periodic table, as well as their oxides or carbonates, can be used as electron donors. Specifically, lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), ytterbium (Yb), indium (In), lithium oxide (Li₂O), and cesium carbonate are preferred. Additionally, organic compounds such as tetrathianaphthacene can also be used as electron donors.
[0304] In the charge generation layer 106, when an electron relay layer is provided between the p-type layer and the electron injection buffer layer, the electron relay layer at least contains a material with electron transport properties and has the function of smoothly transferring electrons while preventing the interaction between the electron injection buffer layer and the p-type layer. The LUMO energy level of the electron transport material contained in the electron relay layer is preferably located between the LUMO energy level of the acceptor material in the p-type layer and the LUMO energy level of the electron transport material contained in the electron transport layer that is in contact with the charge generation layer 106. Specifically, the LUMO energy level of the electron transport material in the electron relay layer is preferably -5.0 eV or higher, more preferably -5.0 eV or higher and -3.0 eV or lower. Furthermore, phthalocyanine materials or metal complexes having metal-oxygen bonds and aromatic ligands are preferably used as the electron transport material in the electron relay layer.
[0305] Note that, although Figure 2D The diagram shows a structure with two layers of organic compound 103 stacked together, but a stacked structure with three or more layers of organic compound can also be used by setting a charge generation layer between different light-emitting layers.
[0306] <<Overlay>>
[0307] Note that, although in Figures 2A to 2E Although not shown in the diagram, a capping layer can also 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 a capping layer on the second electrode 102, the extraction efficiency of light emitted from the second electrode 102 can be improved.
[0308] Specific examples of materials that can be used for the coating include 5,5'-diphenyl-2,2'-di-5H-[1]benzothiopheno[3,2-c]carbazole (abbreviated as BisBTc) and 4,4',4''-(benzene-1,3,5-triyl)tris(dibenzothiophene) (abbreviated as DBT3P-II).
[0309] <<Substrate>>
[0310] Furthermore, the light-emitting device according to one aspect of the present invention can be manufactured on a substrate made of glass, plastic, or the like. As for the stacking order on the substrate, it can be stacked sequentially from either the first electrode 101 side or the second electrode 102 side.
[0311] Furthermore, as a substrate for forming the light-emitting device according to one embodiment of the present invention, materials such as glass, quartz, or plastic can be used. Alternatively, a flexible substrate can also be used. A flexible substrate is a bendable substrate, such as a plastic substrate made of polycarbonate or polyarylate. Additionally, thin films, inorganic thin films formed by vapor deposition, etc., can be used. Note that other materials can be used as long as they function as a support in the manufacturing process of the light-emitting device and optical elements. Alternatively, any material that functions to protect the light-emitting device and optical elements is acceptable.
[0312] For example, various substrates can be used to form light-emitting devices in this specification. There are no particular limitations on the type of substrate. Examples of 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, or substrate films. Examples of glass substrates include barium borosilicate glass, aluminoborosilicate glass, and soda-lime glass. Examples of flexible substrates, laminated films, and substrate films include plastics such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), and polytetrafluoroethylene (PTFE). Alternatively, acrylic resins can be used as examples. Polypropylene, polyester, ethylene fluoride, or polyvinyl chloride can also be used as examples. Alternatively, examples could include resins such as polyamide, polyimide, aromatic polyamide or epoxy, inorganic vapor-deposited films, and paper.
[0313] Alternatively, a flexible substrate can be used as the substrate, and the light-emitting device can be directly formed on the flexible substrate. Alternatively, a release layer can be provided between the substrate and the light-emitting device. A release layer can be used when part or all of the light-emitting device is fabricated on the release layer, and then it is separated from the substrate and transferred to another substrate. In this case, the light-emitting device can also be transferred to a substrate with low heat resistance or a flexible substrate. Furthermore, as the aforementioned release layer, for example, a stacked structure of inorganic films such as tungsten films and silicon oxide films, or a structure in which a resin film such as polyimide is formed on the substrate, can be used.
[0314] In other words, a light-emitting device can be formed on one substrate and then transferred to another substrate. Examples of substrates for transferring the light-emitting device, besides those mentioned above, include cellophane substrates, stone substrates, wood substrates, cloth substrates (including natural fibers (silk, cotton, linen), synthetic fibers (nylon, polyurethane, polyester), or recycled fibers (acetate fiber, cupro fiber, rayon, recycled polyester), leather substrates, and rubber substrates. By using these substrates, it is possible to manufacture light-emitting devices that are not easily damaged, have high heat resistance, are lightweight, or are thin.
[0315] Alternatively, a field-effect transistor (FET) can be formed on the aforementioned substrate, and a light-emitting device can be fabricated on an electrode electrically connected to the FET. This allows for the fabrication of an active matrix display device in which the driving of the light-emitting device is controlled by the FET.
[0316] In this embodiment, one aspect of the present invention will be described. Furthermore, another aspect of the present invention will be described in other embodiments. However, the present invention is not limited to this. That is, various inventive methods are described in this and other embodiments, thus the present invention is not limited to a specific method. For example, although an example of applying one aspect of the present invention to a light-emitting device is shown, the present invention is not limited to this. For example, depending on the circumstances, one aspect of the present invention may not be applied to a light-emitting device. Furthermore, although an example is shown in one aspect of the present invention comprising a first organic compound, a second organic compound, and a guest material having the function of converting a triple excitation energy into light emission, wherein the LUMO energy level of the first organic compound is lower than the LUMO energy level of the second organic compound, and the HOMO energy level of the first organic compound is lower than the HOMO energy level of the second organic compound, the present invention is not limited to this. In one aspect of the present invention, depending on the circumstances, for example, the LUMO energy level of the first organic compound may not be lower than the LUMO energy level of the second organic compound. Furthermore, the HOMO energy level of the first organic compound may not be lower than the HOMO energy level of the second organic compound. Furthermore, for example, one embodiment of the invention illustrates an example of the first organic compound forming an excimer complex with the second compound, but one embodiment of the invention is not limited thereto. In one embodiment of the invention, depending on the circumstances, for example, the first organic compound and the second organic compound may not form an excimer complex. Furthermore, although one embodiment of the invention illustrates an example in which the LUMO energy level of the guest material is higher than the LUMO energy level of the first organic compound, and the HOMO energy level of the guest material is lower than the HOMO energy level of the second organic compound, one embodiment of the invention is not limited thereto. In one embodiment of the invention, depending on the circumstances, for example, the LUMO energy level of the guest material may not be higher than the LUMO energy level of the first organic compound. Furthermore, the HOMO energy level of the guest material may not be lower than the HOMO energy level of the second organic compound.
[0317] The structure shown in this embodiment can be used in appropriate combinations with the structures shown in other embodiments.
[0318] Implementation Method 3
[0319] like Figure 3A and Figure 3B As shown, a plurality of light-emitting devices 130 are formed on an insulating layer 175 to constitute a display device. In this embodiment, a display device according to one aspect of the present invention will be described in detail.
[0320] The display device 100 includes a pixel section 177 in which a plurality of pixels 178 are arranged in a matrix. The pixels 178 include sub-pixels 110R, 110G, and 110B.
[0321] In this specification, etc., the term "subpixel 110" is sometimes used to describe the common features among subpixels 110R, 110G, and 110B. Furthermore, regarding other constituent elements distinguished by letters, reference numerals with omitted letters are sometimes used to describe the common features among these constituent elements.
[0322] Subpixel 110R emits red light, subpixel 110G emits green light, and subpixel 110B emits blue light. Thus, an image can be displayed on pixel unit 177. Note that in this embodiment, only subpixels of three colors—red (R), green (G), and blue (B)—are used as an example for explanation; other colors of subpixels can also be combined. Furthermore, the number of subpixels is not limited to three; it can be four or more. Examples of four subpixels include: a subpixel of four colors—R, G, B, and white (W); a subpixel of four colors—R, G, B, and yellow (Y); and a subpixel of four colors—R, G, B, and infrared (IR); etc.
[0323] In this specification, the row direction is sometimes referred to as the X direction and the column direction as the Y direction. The X direction and the Y direction intersect, for example, perpendicularly.
[0324] exist Figure 3A In the example shown, subpixels of different colors are arranged in the X direction, and subpixels of the same color are arranged in the Y direction. Note that it is also possible to arrange subpixels of different colors in the Y direction and subpixels of the same color in the X direction.
[0325] A connecting portion 140 may be provided on the outer side of the pixel portion 177, and a region 141 may also be provided. For example, the region 141 may be provided between the pixel portion 177 and the connecting portion 140. An organic compound layer 103 may be provided in the region 141. In addition, a conductive layer 151C may be provided in the connecting portion 140.
[0326] exist Figure 3A and Figure 3B In the example shown, region 141 and connecting portion 140 are located to the right of pixel portion 177, but there are no particular restrictions on the position of region 141 and connecting portion 140. Furthermore, region 141 and connecting portion 140 may be one or more.
[0327] Figure 3B It is along Figure 3A An example of a cross-sectional view of the dashed-dot line A1-A2 in the diagram. For example... Figure 3AAs shown, 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 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 disposed on a substrate (not shown). The insulating layers 175, 174, and 173 are provided with openings leading to the conductive layer 172, and a plug 176 is disposed such that it is inserted into the openings.
[0328] In the pixel section 177, a light-emitting device 130 is disposed on the insulating layer 175 and the plug 176. A protective layer 131 is disposed to cover the light-emitting device 130. The substrate 120 is attached to the protective layer 131 by a resin layer 122. In addition, it is preferable to provide an inorganic insulating layer 125 and an insulating layer 127 on the inorganic insulating layer 125 between adjacent light-emitting devices 130.
[0329] Figure 3B Cross-sections of multiple inorganic insulating layers 125 and multiple insulating layers 127 are shown, but when viewed from above the display device 100, the inorganic insulating layers 125 and insulating layers 127 are preferably formed as continuous layers. In other words, the insulating layer 127 is preferably an insulating layer having an opening on the first electrode.
[0330] Figure 3B Light-emitting devices 130R, 130G, and 130B are shown as light-emitting device 130. The light-emitting devices 130R, 130G, and 130B emit different colors. For example, light-emitting device 130R may emit red light, light-emitting device 130G may emit green light, and light-emitting device 130B may emit blue light. Alternatively, light-emitting devices 130R, 130G, or 130B may also emit other visible or infrared light.
[0331] One aspect of the display device of the present invention may have a top emission structure that emits light in a direction opposite to that of the substrate on which the light-emitting device is formed. Alternatively, another aspect of the display device of the present invention may have a bottom emission structure.
[0332] Examples of luminescent materials contained in the light-emitting device 130 include organic compounds or organometallic complexes that emit fluorescence (fluorescent materials), emit phosphorescence (phosphorescent materials), and exhibit thermally activated delayed fluorescence (TADF) materials. Alternatively, inorganic compounds such as quantum dots may also be used.
[0333] The light-emitting device 130R has the following characteristics: Figure 1A The structure shown is as follows. The light-emitting device 130R includes a first electrode (pixel electrode) composed of conductive layers 151R and 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. The common layer 104 may or may not be provided, but its presence reduces damage to the organic compound layer 103R during processing, making it preferred. When the common layer 104 is provided, it is preferably an electron injection layer. Furthermore, 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 Embodiment 2.
[0334] The 130G light-emitting device has such Figure 1A The structure shown is as follows. The light-emitting device 130G includes a first electrode (pixel electrode) composed of conductive layers 151G and 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. The common layer 104 may or may not be provided, but it is preferred to provide a common layer 104 to reduce damage to the organic compound layer 103G during processing. When the common layer 104 is provided, it is preferably an electron injection layer. In addition, when the common layer 104 is provided, the stacked structure of the organic compound layer 103G and the common layer 104 is equivalent to the organic compound layer 103 in Embodiment 2.
[0335] The light-emitting device 130B has the following characteristics: Figure 1A The structure shown is as follows. The light-emitting device 130B includes a first electrode (pixel electrode) composed of conductive layers 151B and 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. The common layer 104 may or may not be provided, but its presence reduces damage to the organic compound layer 103B during processing, making it preferred. When the common layer 104 is provided, it is preferably an electron injection layer. Furthermore, 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 Embodiment 2.
[0336] In a light-emitting device, one of the pixel electrode and the common electrode is used as the anode, and the other is used as the cathode. Unless otherwise specified, the following description assumes that the pixel electrode is used as the anode and the common electrode is used as the cathode.
[0337] Organic compound layers 103R, 103G, and 103B are arranged in an island shape according to each light-emitting device or each light-emitting color. By setting the organic compound layers 103 in an island shape according to each light-emitting device 130, leakage current between adjacent light-emitting devices 130 can be suppressed in high-definition display devices. As a result, crosstalk can be suppressed, and a display device with extremely high contrast can be realized. In particular, a display device with high current efficiency at low brightness can be realized.
[0338] An island-like organic compound layer 103 is formed by depositing an EL film and processing it using photolithography.
[0339] Furthermore, in one embodiment of the display device of the present invention, the first electrode (pixel electrode) of the light-emitting device preferably has a stacked structure. For example, in Figure 3B In the example shown, the first electrode of the light-emitting device 130 has a stacked structure of conductive layer 151 and conductive layer 152. For example, when the display device 100 has a top-emitting structure and the pixel electrode of the light-emitting device 130 is used as the anode, it is preferable that the conductive layer 151 is a layer with high visible light reflectivity, and the conductive layer 152 is, for example, a layer with visible light transmittance and a large work function. When the display device 100 has a top-emitting structure, the higher the visible light reflectivity of the pixel electrode, the more efficient the light extraction of the organic compound layer 103 can be. In addition, when the pixel electrode is used as the anode, the larger the work function of the pixel electrode, the easier it is to inject holes into the organic compound layer 103. Thus, by having a stacked structure of conductive layer 151 with high visible light reflectivity and conductive layer 152 with a large work function in the pixel electrode of the light-emitting device 130, the light-emitting device 130 can be a light-emitting device with high light extraction efficiency and low driving voltage.
[0340] When the conductive layer 151 is a layer with high visible light reflectivity, the visible light reflectivity of the conductive layer 151 is preferably, for example, 40% or more and 100% or less, or 70% or more and 100% or less. Furthermore, when the conductive layer 152 is an electrode with visible light transmittance, the visible light transmittance is preferably, for example, 40% or more.
[0341] In cases where the pixel electrode has a multi-layered stacked structure, the pixel electrode may deteriorate due to reactions between these layers. For example, when the film formed after the pixel electrode is formed is removed by wet etching, galvanic corrosion occurs due to the contact of the chemical solution with the pixel electrode.
[0342] Therefore, in the display device 100 of this embodiment, an insulating layer 156 is formed on the sides of the conductive layers 151 and 152. Thus, for example, when removing the film formed after the formation of the pixel electrode including the conductive layers 151 and 152 using a wet etching method, contact between the chemical solution and the conductive layer 151 can be suppressed. Therefore, for example, galvanic corrosion in the pixel electrode can be suppressed. Therefore, the display device 100 can be manufactured using a high-yield method, thus enabling the realization of an inexpensive display device. Furthermore, defects in the display device 100 can be suppressed, thus making the display device 100 a highly reliable display device.
[0343] As the conductive layer 151, a metallic material can be used, for example. Specifically, metals such as aluminum (Al), titanium (Ti), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), gallium (Ga), zinc (Zn), indium (In), tin (Sn), molybdenum (Mo), tantalum (Ta), tungsten (W), palladium (Pd), gold (Au), platinum (Pt), silver (Ag), yttrium (Y), neodymium (Nd), and alloys thereof can also be used.
[0344] As the conductive layer 152, an oxide containing one or more of indium, tin, zinc, gallium, titanium, aluminum, and silicon can be used. For example, conductive oxides containing one or more of indium oxide, indium tin oxide, indium zinc oxide, zinc oxide, gallium-containing zinc oxide, titanium oxide, gallium-containing indium zinc oxide, aluminum-containing indium zinc oxide, silicon-containing indium tin oxide, and silicon-containing indium zinc oxide are preferred. In particular, silicon-containing indium tin oxide has a large work function, for example, 4.0 eV or more, so it is suitable for use as the conductive layer 152.
[0345] Conductive layer 151 and conductive layer 152 may each have a stacked structure containing multiple layers of different materials. In this case, conductive layer 151 may also include a layer using a material that can be used in conductive layer 152, such as a conductive oxide, and conductive layer 152 may also include a layer using a material that can be used in conductive layer 151, such as a metallic material. For example, when conductive layer 151 has a stacked structure of two or more layers, the layer in contact with conductive layer 152 may be a layer using a material that can be used in conductive layer 152.
[0346] Note that the end of the insulating layer 156 may also have a tapered shape. Specifically, when the end of the insulating layer 156 has a tapered shape with a taper angle of less than 90°, the coverage of structures disposed along the side of the insulating layer 156 can be improved.
[0347] Next, refer to Figures 4A to 9C The description has Figure 3AAn example of a manufacturing method for the display device 100 with the shown structure. In the light-emitting device included in the display device 100, the organic compound layer is formed through a manufacturing process including water treatment. By using the organic compound of one aspect of the present invention in the organic compound layer of the light-emitting device included in one aspect of the display device of the present invention, even if manufactured by a manufacturing process including water treatment, problems such as dissolution of the layer containing the organic compound and penetration of the solution into the layer using the organic compound can be prevented, thereby providing a light-emitting device with excellent properties.
[0348] [Example of manufacturing method]
[0349] Thin films (insulating films, semiconductor films, conductive films, etc.) constituting display devices can be formed using methods such as sputtering, chemical vapor deposition (CVD), vacuum evaporation, pulsed laser deposition (PLD), or alumina deposition (ALD). CVD methods include plasma-enhanced chemical vapor deposition (PECVD) and thermal CVD. Furthermore, metal-organic chemical vapor deposition (MOCVD) is one type of thermal CVD method.
[0350] In addition, the thin films (insulating films, semiconductor films, conductive films, etc.) constituting the display device can be formed using wet deposition methods such as spin coating, dip coating, spray coating, inkjet coating, dispenser coating, screen printing, offset printing, doctor knife coating, slot coating, roller coating, curtain coating, or doctor knife coating.
[0351] In particular, when manufacturing light-emitting devices, vacuum processes such as vapor deposition and solution processes such as spin coating and inkjet printing can be utilized. Examples of vapor deposition methods include physical vapor deposition (PVD) methods such as sputtering, ion plating, ion beam vapor deposition, molecular beam vapor deposition, and vacuum vapor deposition, as well as chemical vapor deposition (CVD). Specifically, functional layers (hole injection layer, hole transport layer, hole blocking layer, light-emitting layer, electron blocking layer, electron transport layer, and electron injection layer, etc.) comprising an organic compound layer can be formed using methods such as vapor deposition (vacuum vapor deposition, etc.), coating methods (dip coating, dye coating, rod coating, spin coating, spray coating), and printing methods (inkjet printing, screen printing, offset printing, flexographic printing, photogravure printing, or microcontact printing, etc.).
[0352] Furthermore, when processing the thin film constituting the display device, it can be processed using techniques such as photolithography. Alternatively, it can be processed using nanoimprinting, sandblasting, or stripping methods. Additionally, island-shaped thin films can be directly formed using deposition methods that utilize metal masks or similar masking techniques.
[0353] As a lithography technique, photolithography can be used, for example. Photolithography typically involves two methods. One is to form a resist mask on the thin film to be processed, for example, by etching the film, and then removing the resist mask. The other is to form a photosensitive thin film, expose and develop it, and then process the film into the desired shape.
[0354] In photolithography, the light used for exposure can be, for example, i-line (wavelength 365nm), g-line (wavelength 436nm), h-line (wavelength 405nm), or a mixture of these. Additionally, ultraviolet light, KrF lasers, or ArF lasers can also be used. Furthermore, immersion lithography can also be used. Extreme ultraviolet (EUV) light or X-rays can also be used as the light for exposure. Alternatively, an electron beam can be used instead of the light for exposure. Extreme ultraviolet light, X-rays, or electron beams allow for extremely fine processing and are therefore preferred. Furthermore, when exposure is performed by scanning with a beam such as an electron beam, a photomask is not required.
[0355] In the etching of thin films, dry etching, wet etching, or sandblasting methods can be used.
[0356] First, such as Figure 4A An insulating layer 171 is formed on a substrate (not shown). Next, a conductive layer 172 and a conductive layer 179 are formed on the insulating layer 171, and an insulating layer 173 is formed on the insulating layer 171 to cover the conductive layers 172 and 179. Next, an insulating layer 174 is formed on the insulating layer 173, and an insulating layer 175 is formed on the insulating layer 174.
[0357] As a substrate, a substrate with heat resistance sufficient to withstand subsequent heat treatment can be used. When using an insulating substrate, glass substrates, quartz substrates, sapphire substrates, ceramic substrates, or organic resin substrates can be used. In addition, single-crystal semiconductor substrates or polycrystalline semiconductor substrates made of materials such as silicon or silicon carbide, compound semiconductor substrates made of materials such as silicon-germanium, SOI substrates, and other semiconductor substrates can also be used.
[0358] Next, as Figure 4AAs shown, openings leading to the conductive layer 172 are formed in insulating layers 175, 174, and 173. Then, a plug 176 is formed by embedding it into these openings.
[0359] Next, as Figure 4A As shown, a conductive film 151f, which will later become conductive layers 151R, 151G, 151B, and 151C, is formed on the plug 176 and the insulating layer 175. The conductive film 151f can be formed, for example, by sputtering or vacuum evaporation. Alternatively, a metallic material can be used as the conductive film 151f.
[0360] Next, as Figure 4A As shown, a conductive film 152f, which will later become conductive layers 152R, 152G, 152B, and 152C, is formed on a conductive film 151f. The conductive film 152f can be formed, for example, by sputtering or vacuum evaporation. Alternatively, a conductive oxide can be used as the conductive film 152f. Or, the conductive film 152f can be a laminated structure of a film using a metallic material and a film using a conductive oxide on that film. For example, the conductive film 152f can be a laminated structure of a film using titanium, silver, or a silver-containing alloy and a film using a conductive oxide on that film.
[0361] Furthermore, the conductive film 152f can be formed using the ALD method. Here, as the conductive film 152f, an oxide containing one or more metals selected from indium, tin, zinc, gallium, titanium, aluminum, and silicon can be used. The conductive film 152f can be formed by repeatedly performing a cycle of introducing a precursor (sometimes referred to as a precursor or metal precursor, etc.), purging the precursor, introducing an oxidant (sometimes referred to as a reactant, reactant, or non-metal precursor, etc.), and purging the oxidant. When forming a conductive film 152f from an oxide film containing multiple metals, such as indium tin oxide, the metal composition can be controlled by changing the number of cycles according to the type of precursor.
[0362] For example, in the case of depositing an indium tin oxide film as a conductive film 152f, after introducing an indium-containing precursor, the precursor is purged and an oxidant is introduced to form an In-O film. Next, after introducing a tin-containing precursor, the precursor is purged and an oxidant is introduced to form a Sn-O film. Here, by making the number of cycles for forming the In-O film greater than the number of cycles for forming the Sn-O film, the number of In atoms contained in the conductive film 152f can be greater than the number of Sn atoms.
[0363] Furthermore, for example, when depositing a zinc oxide film as the conductive film 152f, a Zn-O film is formed through the above process. Furthermore, for example, when depositing an aluminum-zinc oxide film as the conductive film 152f, both a Zn-O film and an Al-O film are formed through the above process. Furthermore, for example, when depositing a titanium oxide film as the conductive film 152f, a Ti-O film is formed through the above process. Furthermore, for example, when depositing an indium tin oxide film containing silicon as the conductive film 152f, an In-O film, a Sn-O film, and a Si-O film are formed through the above process. Furthermore, for example, when depositing a zinc oxide film containing gallium, both a Ga-O film and a Zn-O film are formed through the above process.
[0364] As indium-containing precursors, for example, triethylindium, trimethylindium, or [1,1,1-trimethyl-N-(trimethylsilyl)amide]-indium can be used. As tin-containing precursors, for example, tin chloride or tetra(dimethylamide)tin can be used. As zinc-containing precursors, for example, diethylzinc or dimethylzinc can be used. As gallium-containing precursors, for example, triethylgallium can be used. As titanium-containing precursors, for example, titanium chloride, tetra(dimethylamide)titanium, or tetraisopropyl titanate can be used. As aluminum-containing precursors, for example, aluminum chloride or trimethylaluminum can be used. As silicon-containing precursors, for example, trisilylamine, bis(diethylamino)silane, tri(dimethylamino)silane, or bis(tert-butylamino)silane or bis(ethylmethylamino)silane can be used. Additionally, water vapor, oxygen plasma, or ozone gas can be used as oxidants.
[0365] Next, as Figure 4A As shown, a photoresist mask 191 is formed on conductive films 151f and 152f. The photoresist mask 191 can be formed by coating a photosensitive material (photoresist) and then exposing and developing it.
[0366] Next, as Figure 4B As shown, conductive films 151f and 152f, for example, are removed using an etching method, specifically a dry etching method, to remove areas of the conductive film 151f and 152f that do not overlap with the resist mask 191, thereby forming a pixel electrode including conductive layers 151 and 152. Note that if conductive film 151f includes a layer of conductive oxide such as indium tin oxide, this layer can also be removed using a wet etching method. Thus, conductive layers 151 and 152 are formed. Note that, for example, when a portion of conductive film 151f is removed using a dry etching method, a recess may sometimes be formed on an area of the insulating layer 175 that does not overlap with conductive layer 151.
[0367] Note that, after forming conductive layers 152R, 152G, 152B, and 152C by processing conductive film 152f using lithography, conductive film 151f can be processed using conductive layers 152R, 152G, 152B, and 152C as masks. Specifically, for example, after forming a resist mask, a portion of conductive film 152f can be removed using an etching method. For example, wet etching can be used to remove conductive film 152f. Note that dry etching can also be used to remove conductive film 152f. Then, wet etching is preferably used to remove conductive film 151f.
[0368] Here, it is preferable to perform a hydrophobic treatment on the conductive layer 152. This hydrophobic treatment can change the surface state of the object being treated from hydrophilic to hydrophobic, or it can increase the hydrophobicity of the surface. By performing a hydrophobic treatment on the conductive layer 152, the adhesion between the conductive layer 152 and the organic compound layer 103 to be formed in subsequent processes can be improved, thereby suppressing film peeling. Note that a hydrophobic treatment may not be performed.
[0369] Next, as Figure 4C As shown, the resist mask 191 is removed. The resist mask 191 can be removed, for example, by ashing using oxygen plasma. Alternatively, oxygen gas and Group 18 elements such as CF4, C4F8, SF6, CHF3, Cl2, H2O, BCl3, or He can be used. Alternatively, the resist mask 191 can also be removed by wet etching.
[0370] Next, as Figure 4D As shown, an insulating film 156f, which will later become insulating layers 156R, 156G, 156B, and 156C, is formed on conductive layers 151R and 152R, conductive layers 151G and 152G, conductive layers 151B and 152B, conductive layers 151C and 152C, and insulating layer 175. The insulating film 156f can be formed, for example, using CVD, ALD, sputtering, or vacuum evaporation.
[0371] Inorganic materials can be used for the insulating film 156f. For example, inorganic insulating films such as oxide insulating films, nitride insulating films, oxynitride insulating films, or oxynitride insulating films can be used as the insulating film 156f. For instance, silicon-containing insulating films such as oxide insulating films, nitride insulating films, oxynitride insulating films, or oxynitride insulating films can be used as the insulating film 156f. For example, silicon oxynitride can be used as the insulating film 156f.
[0372] Next, as Figure 4EAs shown, insulating film 156f is processed to form insulating layers 156R, 156G, 156B, and 156C. For example, insulating layer 156 can be formed by etching the top surface of insulating film 156f in a substantially uniform manner. This planarization process through uniform etching is also known as etch-back. Alternatively, insulating layer 156 can also be formed using photolithography.
[0373] Next, as Figure 5A As shown, an organic compound film 103Rf, which will later become an organic compound layer 103R, is formed on conductive layer 152R, conductive layer 152G, conductive layer 152B, insulating layer 156R, insulating layer 156G, insulating layer 156B and insulating layer 175.
[0374] like Figure 5A As shown, no organic compound film 103Rf is formed on the conductive layer 152C. For example, by using a mask that defines the deposition area (also called a zone mask or coarse metal mask, etc., to distinguish it from a high-precision metal mask), the organic compound film 103Rf can be deposited only in the desired area. By employing a deposition process using a zone mask and a processing process using a resist mask, the light-emitting device can be manufactured with a simpler process.
[0375] The organic compound film 103Rf can be formed, for example, by vapor deposition, specifically by vacuum vapor deposition. Alternatively, the organic compound film 103Rf can also be formed by methods such as transfer printing, printing, inkjet printing, and coating.
[0376] Next, as Figure 5A As shown, a sacrificial film 158Rf, which will later become a sacrificial layer 158R, and a mask film 159Rf, which will later become a mask layer 159R, are sequentially formed on an organic compound film 103Rf, a conductive layer 152C, and an insulating layer 175.
[0377] Note that in this embodiment, an example is shown where the mask film is composed of a two-layer structure of sacrificial film 158Rf and mask film 159Rf, but the mask film may have a single-layer structure or a stacked structure of three or more layers.
[0378] By providing a sacrificial layer on the organic compound film 103Rf, the damage to the organic compound film 103Rf during the manufacturing process of the display device can be reduced, thereby improving the reliability of the light-emitting device.
[0379] The sacrificial film 158Rf is a film with high tolerance to the processing conditions of the organic compound film 103Rf, specifically a film with a greater etch selectivity than the organic compound film 103Rf. The mask film 159Rf is a film with a greater etch selectivity than the sacrificial film 158Rf.
[0380] Furthermore, the sacrificial film 158Rf and the mask film 159Rf are formed at a temperature lower than the heat resistance temperature of the organic compound film 103Rf. The substrate temperature during the formation of the sacrificial film 158Rf and the sacrificial film 159Rf is typically below 200°C, preferably below 150°C, more preferably below 120°C, further preferably below 100°C, and even more preferably below 80°C.
[0381] The sacrificial film 158Rf and the mask film 159Rf are preferably films that can be removed by wet etching. By using wet etching, the damage to the organic compound film 103Rf during the processing of the sacrificial film 158Rf and the mask film 159Rf can be reduced compared to using dry etching.
[0382] The sacrificial film 158Rf and the mask film 159Rf can be formed, for example, by sputtering, ALD (thermal ALD, PEALD), CVD, or vacuum evaporation. Alternatively, they can also be formed using the aforementioned wet deposition methods.
[0383] The sacrificial film 158Rf formed on the organic compound film 103Rf is preferably formed by a method that causes less damage to the organic compound film 103Rf compared to the formation of the mask film 159Rf. For example, the sacrificial film 158Rf is more preferably formed by ALD or vacuum evaporation than by sputtering.
[0384] As the sacrificial film 158Rf and the mask film 159Rf, one or more of the following can be used: metal film, alloy film, metal oxide film, semiconductor film, organic insulating film and inorganic insulating film.
[0385] The sacrificial film 158Rf and the mask film 159Rf can each be made of metallic materials such as gold, silver, platinum, magnesium, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, palladium, titanium, aluminum, yttrium, zirconium, and tantalum, or alloys containing such metallic materials. Low-melting-point materials such as aluminum or silver are particularly preferred. By using a metallic material capable of blocking ultraviolet light as one or both of the sacrificial film 158Rf and the mask film 159Rf, ultraviolet radiation can be suppressed from reaching the organic compound film 103Rf, thus suppressing the degradation of the organic compound film 103Rf, which is therefore preferred.
[0386] In addition, the sacrificial film 158Rf and the mask film 159Rf can each be 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), or indium tin oxide containing silicon.
[0387] Note that element M (which is one or more of aluminum, silicon, boron, yttrium, copper, vanadium, beryllium, titanium, iron, nickel, germanium, zirconium, molybdenum, lanthanum, cerium, neodymium, hafnium, tantalum, tungsten, and magnesium) can also be used to replace gallium.
[0388] Furthermore, the sacrificial film and mask film preferably use films containing materials that have light-blocking properties, especially ultraviolet light-blocking properties. As the light-blocking material, various materials such as metals, insulators, semiconductors, and semi-metals with ultraviolet light-blocking properties can be used. Since part or all of the sacrificial film and mask film will be removed in subsequent processes, the sacrificial film and mask film are preferably films that can be processed by etching, and especially preferably films with good processability.
[0389] When using semiconductor materials such as silicon or germanium as sacrificial films and mask films, these materials have high affinity with the semiconductor manufacturing process and are therefore preferred. Alternatively, oxides or nitrides of the aforementioned semiconductor materials can be used. Alternatively, non-metallic materials such as carbon or their compounds can be used. Furthermore, metals such as titanium, tantalum, tungsten, chromium, and aluminum, or alloys containing one or more of these can be used. Additionally, oxides containing the aforementioned metals, such as titanium oxide or chromium oxide, or nitrides such as titanium nitride, chromium nitride, or tantalum nitride can be used.
[0390] Furthermore, by using a film made of a material with UV-blocking properties as a sacrificial film or mask film, it is possible to suppress UV radiation from reaching the organic compound layer, for example, during the exposure process. By suppressing UV damage to the organic compound layer, the reliability of the light-emitting device can be improved.
[0391] Note that films containing materials with UV-blocking properties also produce the same effect when used as materials for the inorganic insulating film 125f described later.
[0392] Furthermore, various inorganic insulating films can be used as both the sacrificial film 158Rf and the mask film 159Rf. In particular, oxide insulating films exhibit higher adhesion to the organic compound film 103Rf compared to nitrided insulating films, and are therefore preferred. For example, inorganic insulating materials such as alumina, hafnium oxide, or silicon oxide can be used for both the sacrificial film 158Rf and the mask film 159Rf. For example, alumina films can be formed using the ALD method for both the sacrificial film 158Rf and the mask film 159Rf. Using the ALD method can reduce damage to the substrate (especially the organic compound layer), and is therefore preferred.
[0393] For example, an inorganic insulating film (e.g., an alumina film) formed using the ALD method can be used as the sacrificial film 158Rf, and an inorganic film (e.g., an In-Ga-Zn oxide film, an aluminum film, or a tungsten film) formed using the sputtering method can be used as the mask film 159Rf.
[0394] Furthermore, the same inorganic insulating film can be used for both the sacrificial layer 158Rf and the inorganic insulating layer 125 to be formed later. For example, an alumina film formed using the ALD method can be used for both the sacrificial layer 158Rf and the inorganic insulating layer 125. Here, the sacrificial layer 158Rf and the inorganic insulating layer 125 can be deposited under the same or different conditions. For example, by depositing the sacrificial film 158Rf under the same conditions as the inorganic insulating layer 125, the sacrificial film 158Rf can be formed as an insulating layer with high barrier properties against at least one of water and oxygen. On the other hand, the sacrificial film 158Rf is a layer that will be mostly or entirely removed in a later process, so it is preferably easy to process. Therefore, the sacrificial layer 158Rf is preferably deposited under conditions with a lower substrate temperature than that of the inorganic insulating layer 125.
[0395] Organic materials can also be used as one or both of the sacrificial film 158Rf and the mask film 159Rf. For example, materials that are chemically stable in solvents that are soluble in at least the uppermost layer of the organic compound film 103Rf can also be used as organic materials. In particular, materials soluble in water or alcohol can be used appropriately. When depositing the above-mentioned materials, it is preferable to apply the materials by a wet deposition method while the materials are dissolved in a solvent such as water or alcohol, and then perform a heat treatment to evaporate the solvent. At this time, it is preferable to perform the heat treatment under a reduced pressure atmosphere, thereby removing the solvent at a low temperature and for a short time, and reducing the thermal damage to the organic compound film 103Rf.
[0396] Sacrificial membrane 158Rf and mask membrane 159Rf can each be made of organic resins such as polyvinyl alcohol (PVA), polyvinyl butyral, polyvinylpyrrolidone, polyethylene glycol, polyglycerol, pullulan, water-soluble cellulose, alcohol-soluble polyamide resin or perfluoropolymer, etc.
[0397] For example, an organic film (e.g., a PVA film) formed using any one of the above-described wet deposition methods can be used as the sacrificial film 158Rf, and an inorganic film (e.g., a silicon nitride film) formed using sputtering can be used as the mask film 159Rf.
[0398] Next, as Figure 5A As shown, a photoresist mask 190R is formed on a photomask film 159Rf. The photoresist mask 190R can be formed by applying a photosensitive material (photoresist) and then exposing and developing it.
[0399] The 190R resist mask can be manufactured using either positive or negative resist materials.
[0400] The resist mask 190R is provided at the position overlapping with the conductive layer 152R. Preferably, the resist mask 190R is also provided at the position overlapping with the conductive layer 152C. This can suppress damage to the conductive layer 152C during the manufacturing process of the display device. Note that the resist mask 190R may also be omitted from the conductive layer 152C. Furthermore, as... Figure 5A As shown in the cross-sectional view along B1-B2, the resist mask 190R is preferably provided in such a way that it covers the end of the organic compound film 103Rf to the end of the conductive layer 152C (the end on the side of the organic compound film 103Rf).
[0401] Next, as Figure 5B As shown, a portion of the mask film 159Rf is removed using a resist mask 190R to form a mask layer 159R. The mask layer 159R remains on the conductive layers 152R and 152C. Then, the resist mask 190R is removed. Next, the mask layer 159R is used as a mask (also called a hard mask) to remove a portion of the sacrificial film 158Rf to form a sacrificial layer 158R.
[0402] The sacrificial film 158Rf and the mask film 159Rf can be processed using either wet etching or dry etching. The processing of the sacrificial film 158Rf and the mask film 159Rf is preferably performed using isotropic etching.
[0403] By using wet etching, damage to the organic compound film 103Rf can be reduced during the processing of the sacrificial film 158Rf and the mask film 159Rf compared to using dry etching. When using wet etching, solutions such as developer, aqueous tetramethylammonium hydroxide (TMAH) solution, dilute hydrofluoric acid, oxalic acid, phosphoric acid, acetic acid, nitric acid, or mixtures thereof are preferably used.
[0404] Since the organic compound film 103Rf is not exposed during the processing of the mask film 159Rf, the range of processing methods is wider compared to the case of processing the sacrificial film 158Rf. Specifically, when processing the mask film 159Rf, even when using an oxygen-containing gas as the etching gas, the degradation of the organic compound film 103Rf can be suppressed.
[0405] Furthermore, when dry etching is used in the processing of the sacrificial film 158Rf, the degradation of the organic compound film 103Rf can be suppressed by not using an oxygen-containing gas as the etching gas. In the case of using dry etching, for example, a gas containing CF4, C4F8, SF6, CHF3, Cl2, H2O, BCl3, or Group 18 elements such as He is preferably used as the etching gas.
[0406] For example, when using an alumina film formed by the ALD method as the sacrificial film 158Rf, a portion of the sacrificial film 158Rf can be removed using CHF3 and He, or CHF3, He, and CH4, via dry etching. Similarly, when using an In-Ga-Zn oxide film formed by sputtering as the mask film 159Rf, a portion of the mask film 159Rf can be removed using dilute phosphoric acid via wet etching. Alternatively, a portion of the mask film 159Rf can be removed using CH4 and Ar via dry etching. Or, a portion of the mask film 159Rf can be removed using dilute phosphoric acid via wet etching. Furthermore, when using a tungsten film formed by sputtering as the mask film 159Rf, a portion of the mask film 159Rf can be removed using SF6, CF4, and O2, or CF4, Cl2, and O2 via dry etching.
[0407] The resist mask 190R can be removed using the same method as the resist mask 191. The resist mask 190R can be removed, for example, by ashing using oxygen plasma. Alternatively, oxygen gas and Group 18 elements such as CF4, C4F8, SF6, CHF3, Cl2, H2O, BCl3, or He can be used. Alternatively, the resist mask 190R can be removed by wet etching. In this case, the sacrificial film 158Rf is on the outermost surface and the organic compound film 103Rf is not exposed, so damage to the organic compound film 103Rf can be suppressed during the removal process of the resist mask 190R. Furthermore, the range of removal methods for the resist mask 190R can be expanded.
[0408] Next, as Figure 5B As shown, an organic compound film 103Rf is processed to form an organic compound layer 103R. For example, a mask layer 159R and a sacrificial layer 158R are used as a hard mask to remove part of the organic compound film 103Rf to form the organic compound layer 103R.
[0409] Therefore, as Figure 5B As shown, the conductive layer 152R has a stacked structure of organic compound layer 103R, sacrificial layer 158R, and mask layer 159R remaining on it. In addition, conductive layers 152G and 152B are exposed.
[0410] Figure 5B An example is shown where the end of the organic compound layer 103R is located inside the end of the conductive layer 152R. By employing this structure, pixel miniaturization can be achieved, enabling the fabrication of high-definition displays. Note that although in Figure 5B Not shown in the figure, but sometimes the above-described etching process forms recesses in the region of the insulating layer 175 that does not overlap with the organic compound layer 103R.
[0411] As described above, the resist mask 190R is preferably arranged such that it covers the end of the organic compound layer 103R between B1 and B2 to the end of the conductive layer 152C (the end on the side of the organic compound layer 103R). Thus, as Figure 5B As shown, the sacrificial layer 158R and the mask layer 159R are disposed between the dashed lines B1-B2 in such a way that they cover the end of the organic compound layer 103R to the end of the conductive layer 152C (the end on the side of the organic compound layer 103R). Therefore, exposure of the insulating layer 175, for example, between B1-B2 can be suppressed. This also prevents the conductive layer 179 from being exposed due to etching or other removal of portions of the insulating layers 175, 174, and 173. Therefore, unintentional electrical connections of the conductive layer 179 to other conductive layers can be suppressed. For example, short circuits between the conductive layer 179 and the common electrode 155 to be formed in subsequent processes can be suppressed.
[0412] The organic compound film 103Rf is preferably processed using anisotropic etching. Anisotropic dry etching is particularly preferred. Alternatively, wet etching may also be used.
[0413] When using dry etching, the degradation of the organic compound film 103Rf can be suppressed by not using an oxygen-containing gas as the etching gas.
[0414] Alternatively, oxygen-containing gases can be used as etching gases. When the etching gas contains oxygen, the etching rate can be increased. Therefore, etching can be performed at low power conditions while maintaining a sufficient etching rate. This suppresses damage to the organic compound film 103Rf. Furthermore, it suppresses defects such as the adhesion of reaction products generated during etching.
[0415] When using dry etching, it is preferable to use a gas containing one or more Group 18 elements such as H2, CF4, C4F8, SF6, CHF3, Cl2, H2O, BCl3, and He or Ar as the etching gas. Alternatively, it is preferable to use a gas containing one or more of the above-mentioned gases and oxygen as the etching gas. Oxygen gas may also 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. Furthermore, for example, a gas containing CF4, He, and oxygen can be used as the etching gas. Additionally, for example, a gas containing H2 and Ar and an oxygen-containing gas can be used as the etching gas.
[0416] As described above, in one aspect of the present invention, a mask layer 159R is formed by forming a resist mask 190R on a mask film 159Rf and removing a portion of the mask film 159Rf using the resist mask 190R. Then, an organic compound layer 103R is formed by using the mask layer 159R as a mask to remove a portion of the organic compound film 103Rf. Therefore, it can be said that the organic compound layer 103R is formed by processing the organic compound film 103Rf using lithography. Alternatively, a portion of the organic compound film 103Rf can be removed using the resist mask 190R. Then, the resist mask 190R can also be removed.
[0417] Next, for example, it is preferable to perform a hydrophobic treatment on the conductive layer 152G. During the processing of the organic compound film 103Rf, the surface state of, for example, the conductive layer 152G sometimes becomes hydrophilic. By performing a hydrophobic treatment on the conductive layer 152G, for example, the adhesion between the conductive layer 152G and the layer to be formed in a later process (here, the organic compound layer 103G) can be improved, thereby suppressing film peeling. Note that a hydrophobic treatment may also be omitted.
[0418] Next, as Figure 6A As shown, an organic compound film 103Gf, which will later become an organic compound layer 103G, is formed on conductive layer 152G, conductive layer 152B, insulating layer 156R, insulating layer 156G, insulating layer 156B, mask layer 159R, and insulating layer 175.
[0419] The organic compound membrane 103Gf can be formed using the same method as that used in forming the organic compound membrane 103Rf. Furthermore, the organic compound membrane 103Gf can have the same structure as the organic compound membrane 103Rf.
[0420] Next, as Figure 6A As shown, a sacrificial film 158Gf, which will later become a sacrificial layer 158G, and a mask film 159Gf, which will later become a mask layer 159G, are sequentially formed on an organic compound film 103Gf and a mask layer 159R. Then, a photoresist mask 190G is formed. The materials and formation methods of the sacrificial film 158Gf and the mask film 159Gf are the same as those used for the sacrificial film 158Rf and the mask film 159Rf. The materials and formation methods of the photoresist mask 190G are the same as those used for the photoresist mask 190R.
[0421] The resist mask 190G is positioned at the location where it overlaps with the conductive layer 152G.
[0422] Next, as Figure 6B As shown, a portion of the mask film 159Gf is removed using a resist mask 190G to form a mask layer 159G. The mask layer 159G remains on the conductive layer 152G. Then, the resist mask 190G is removed. Next, the mask layer 159G is used as part of the mask removal sacrificial film 158Gf to form a sacrificial layer 158G. Next, an organic compound film 103Gf is processed to form an organic compound layer 103G. For example, the mask layer 159G and the sacrificial layer 158G are used as part of the hard mask removal organic compound film 103Gf to form the organic compound layer 103G.
[0423] Therefore, as Figure 6B As shown, the conductive layer 152G has a stacked structure of organic compound layer 103G, sacrificial layer 158G, and mask layer 159G remaining on it. In addition, mask layer 159R and conductive layer 152B are exposed.
[0424] Next, for example, it is preferable to perform a hydrophobic treatment on the conductive layer 152B. During the processing of the organic compound film 103Gf, the surface state of, for example, the conductive layer 152B sometimes becomes hydrophilic. By performing a hydrophobic treatment on the conductive layer 152B, for example, the adhesion between the conductive layer 152B and the layer to be formed in a later process (here, the organic compound layer 103B) can be improved, thereby suppressing film peeling. Note that a hydrophobic treatment may also be omitted.
[0425] Next, as Figure 6CAs shown, an organic compound film 103Bf, which will later become an organic compound layer 103B, is formed on conductive layer 152B, mask layer 159R, insulating layer 156R, insulating layer 156G, insulating layer 156B, mask layer 159G, and insulating layer 175.
[0426] The organic compound membrane 103Bf can be formed using the same method as that used in forming the organic compound membrane 103Rf. Furthermore, the organic compound membrane 103Bf can have the same structure as the organic compound membrane 103Rf.
[0427] Next, as Figure 6C As shown, a sacrificial film 158Bf, which will later become a sacrificial layer 158B, and a mask film 159Bf, which will later become a mask layer 159B, are sequentially formed on an organic compound film 103Bf and a mask layer 159R. Then, a photoresist mask 190B is formed. The materials and formation methods of the sacrificial film 158Bf and the mask film 159Bf are the same as those used for the sacrificial film 158Rf and the mask film 159Rf. The materials and formation methods of the photoresist mask 190B are the same as those used for the photoresist mask 190R.
[0428] The resist mask 190B is disposed at a position overlapping the conductive layer 152B.
[0429] Next, as Figure 6D As shown, a portion of the mask film 159Bf is removed using a photoresist mask 190B to form a mask layer 159B. The mask layer 159B remains on the conductive layer 152B. Then, the photoresist mask 190B is removed. Next, the mask layer 159B is used as part of the mask removal sacrificial film 158Bf to form a sacrificial layer 158B. Next, an organic compound film 103Bf is processed to form an organic compound layer 103B. For example, the mask layer 159B and the sacrificial layer 158B are used as part of the hard mask removal organic compound film 103Bf to form the organic compound layer 103B.
[0430] Therefore, as Figure 6D As shown, the conductive layer 152B has a stacked structure of organic compound layer 103B, sacrificial layer 158B, and mask layer 159B remaining on it. In addition, mask layer 159R and mask layer 159G are exposed.
[0431] Note that the side surfaces of organic compound layers 103R, 103G, and 103B are preferably perpendicular to or substantially perpendicular to the surface to which they are formed. For example, the angle formed between the surface to which they are formed and these side surfaces is preferably 60 degrees or more and 90 degrees or less.
[0432] As described above, the distance between two adjacent organic compound layers in the organic compound layers 103R, 103G, and 103B formed using photolithography can be reduced to 8 μm or less, 5 μm or less, 3 μm or less, 2 μm or less, or 1 μm or less. This distance can be specified, for example, based on the distance between the opposite ends of two adjacent organic compound layers in the organic compound layers 103R, 103G, and 103B. Thus, by reducing the distance between the island-shaped organic compound layers, a display device with high resolution and a large aperture ratio can be provided. Furthermore, the distance between the first electrodes of adjacent light-emitting devices can also be reduced, for example, to 10 μm or less, 8 μm or less, 5 μm or less, 3 μm or less, or 2 μm or less. Moreover, the distance between the first electrodes of adjacent light-emitting devices is preferably 2 μm or more and 5 μm or less.
[0433] Next, as Figure 7A As shown, it is preferable to remove mask layers 159R, 159G, and 159B. Depending on subsequent processes, sacrificial layers 158R, 158G, 158B, mask layers 159R, 159G, and 159B may sometimes remain in the display device. By removing mask layers 159R, 159G, and 159B at this stage, it is possible to prevent them from remaining in the display device. For example, when conductive materials are used in mask layers 159R, 159G, and 159B, by removing them beforehand, leakage current and capacitance formation due to the remaining mask layers 159R, 159G, and 159B can be suppressed.
[0434] Note that although this embodiment uses the case where mask layers 159R, 159G, and 159B are removed as an example, it is also possible to proceed with the next process without removing mask layers 159R, 159G, and 159B. For example, when mask layers 159R, 159G, and 159B contain the aforementioned material with UV-blocking properties, proceeding to the next process without removing these mask layers can protect the organic compound layer from UV radiation, which is therefore preferred.
[0435] The mask layer removal process can use the same method as the mask film processing process. By using wet etching, compared with the case of using dry etching, the damage to the organic compound layers 103R, 103G, and 103B during mask layer removal can be reduced.
[0436] Alternatively, the mask layer can be removed by dissolving it in a solvent such as water or alcohol. Examples of alcohols include ethanol, methanol, isopropanol (IPA), or glycerol.
[0437] After removing the mask layer, a drying process can be performed to remove water contained in organic compound layers 103R, 103G, and 103B, as well as water adsorbed on the surfaces of organic compound layers 103R, 103G, and 103B. For example, a heating process can be performed under an inert gas atmosphere or a reduced pressure atmosphere. The heating process 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. Using a reduced pressure atmosphere allows for drying at lower temperatures, which is therefore preferred.
[0438] Next, as Figure 7B As shown, an inorganic insulating film 125f, which will later become an inorganic insulating layer 125, is formed by covering organic compound layer 103R, organic compound layer 103G, organic compound layer 103B, sacrificial layer 158R, sacrificial layer 158G, and sacrificial layer 158B.
[0439] As described later, the insulating film, which will later become the insulating layer 127, is formed by contacting the top surface of the inorganic insulating film 125f. Therefore, the top surface of the inorganic insulating film 125f preferably has high affinity with the material used for the insulating film (e.g., a photosensitive resin composition containing acrylic resin). To improve this affinity, a surface treatment can be performed to hydrophobize (or improve) the top surface of the inorganic insulating film 125f. For example, a silanizing agent such as hexamethyldisilazane (HMDS) is preferably used for treatment. By hydrophobizing the top surface of the inorganic insulating film 125f in this way, the insulating film 127f can be formed with high adhesion. In addition, the above-described hydrophobic treatment can also be performed as a surface treatment.
[0440] Next, as Figure 7C As shown, an insulating film 127f, which will later become an insulating layer 127, is formed on an inorganic insulating film 125f.
[0441] The inorganic insulating film 125f and the insulating film 127f are preferably deposited by a formation method that causes less damage to the organic compound layers 103R, 103G, and 103B. In particular, the inorganic insulating film 125f is formed in contact with the sides of the organic compound layers 103R, 103G, and 103B, so the inorganic insulating film 125f is preferably deposited by a formation method that causes less damage to the organic compound layers 103R, 103G, and 103B than when the insulating film 127f is deposited.
[0442] Furthermore, the inorganic insulating film 125f and the insulating film 127f are each formed 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. By increasing the substrate temperature during deposition, an inorganic insulating film 125f with low impurity concentration and high barrier properties against at least one of water and oxygen can be formed even with a thin thickness.
[0443] The substrate temperature for 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.
[0444] As the inorganic insulating film 125f, it is preferable to form an insulating film with a thickness of 3 nm or more, 5 nm or more, or 10 nm or more and a thickness of 200 nm or less, 150 nm or less, 100 nm or less, or 50 nm or less within the above-mentioned substrate temperature range.
[0445] The inorganic insulating film 125f is preferably formed using the ALD method, for example. The ALD method reduces deposition damage and allows for the deposition of films with high coverage, making it preferred. For example, an alumina film is preferably formed using the ALD method as the inorganic insulating film 125f.
[0446] In addition, the inorganic insulating film 125f can also be formed using sputtering, CVD, or PECVD methods, which have higher deposition rates than ALD. This allows for the production of highly reliable display devices with high productivity.
[0447] The insulating film 127f is preferably formed using the wet deposition method described above. The insulating film 127f is preferably formed, for example, by spin coating using a photosensitive material, and more specifically, preferably by using a photosensitive resin composition containing acrylic resin.
[0448] For example, it is preferable to use a resin composition containing a polymer, an acid-generating agent, and a solvent to form the insulating film 127f. The polymer is formed using one or more monomers and has a structure in which one or more structural units (also called constituent units) are repeated regularly or irregularly. As the acid-generating agent, one or both of a compound that generates acid by irradiation and a compound that generates acid by heating can be used. The resin composition may also contain one or more of a photosensitizer, sensitizer, catalyst, adhesive aid, surfactant, and antioxidant.
[0449] Furthermore, it is preferable to perform a heat treatment (also known as pre-baking) after forming the insulating film 127f. This heat treatment is performed at a temperature lower than the heat resistance temperature of the organic compound layers 103R, 103G, and 103B. The substrate temperature during the heat treatment is preferably 50°C or higher and 200°C or lower, more preferably 60°C or higher and 150°C or lower, and even more preferably 70°C or higher and 120°C or lower. This removes the solvent from the insulating film 127f.
[0450] Next, exposure is performed to expose a portion of the insulating film 127f to visible light or ultraviolet light. Here, when a positive photosensitive resin composition containing acrylic resin is used for the insulating film 127f, visible light or ultraviolet light is irradiated onto the area where the insulating layer 127 will not be formed in a later process. The insulating layer 127 is formed in the area sandwiched by 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. Note that when a negative photosensitive material is used for the insulating film 127f, visible light or ultraviolet light is irradiated onto the area where the insulating layer 127 will be formed.
[0451] By utilizing the area exposed to the insulating film 127f, the width of the insulating layer 127 to be formed later can be controlled. In this embodiment, the insulating layer 127 is processed such that it has a portion overlapping the top surface of the conductive layer 151.
[0452] The light used for exposure preferably has an i-line (wavelength 365 nm). Alternatively, the light used for exposure may also have at least one of a g-line (wavelength 436 nm) and an h-line (wavelength 405 nm).
[0453] Here, by providing an oxygen-blocking insulating layer (such as an alumina film) as one or both of the sacrificial layer 158 (sacrificial layer 158R, sacrificial layer 158G, and sacrificial layer 158B) and the inorganic insulating film 125f, oxygen diffusion to the organic compound layers 103R, 103G, and 103B can be suppressed. When light (visible light or ultraviolet light) is irradiated onto the organic compound layers, the organic compounds contained in these layers may become excited and promote reaction with oxygen in the atmosphere. Specifically, when light (visible light or ultraviolet light) is irradiated onto the organic compound layers in an oxygen-containing atmosphere, oxygen may bond to the organic compounds contained in these layers. By providing the sacrificial layer 158 and the inorganic insulating film 125f on the island-like organic compound layers, the bonding of oxygen in the atmosphere to the organic compounds contained in these layers can be suppressed.
[0454] Next, as Figure 8AAs shown, the exposed areas in the insulating film 127f are removed by development to form the insulating layer 127a. The insulating layer 127a is formed in the area sandwiched by any two of the conductive layers 152R, 152G, and 152B, and in the area surrounding the conductive layer 152C. Here, when acrylic resin is used for the insulating film 127f, an alkaline solution, such as TMAH, can be used as the developing solution.
[0455] Next, residues from the development process (so-called scum) can also be removed. For example, residues can be removed by ashing using oxygen plasma.
[0456] Alternatively, etching can be performed to adjust the surface height of the insulating layer 127a. The insulating layer 127a can also be processed, for example, by ashing using oxygen plasma. Furthermore, when a non-photosensitive material is used as the insulating film 127f, the surface height of the insulating film 127f can also be adjusted, for example, by this ashing process.
[0457] Next, as Figure 8B As shown, an etching process is performed using insulating layer 127a as a mask to remove a portion of the inorganic insulating film 125f. Furthermore, this etching process can also reduce the thickness of a portion of sacrificial layers 158R, 158G, and 158B. Thus, an inorganic insulating layer 125 is formed beneath insulating layer 127a. Additionally, portions of the surfaces of sacrificial layers 158R, 158G, and 158B are exposed. The etching process using insulating layer 127a as a mask is sometimes referred to as the first etching process.
[0458] The first etching process can be performed by dry etching or wet etching. When the inorganic insulating film 125f is deposited using the same material as the sacrificial layers 158R, 158G and 158B, the first etching process can be performed in one step, which is preferred.
[0459] By using the insulating layer 127a with a tapered side as a mask for etching, the side surfaces of the inorganic insulating layer 125 and the upper ends of the side surfaces of the sacrificial layers 158R, 158G and 158B can be more easily made into a tapered shape.
[0460] When performing dry etching, chlorine-based gases are preferred. One or more of the following chlorine-based gases can be used: Cl2, BCl3, SiCl4, and CCl4. Alternatively, one or more of the following gases can be appropriately added to the chlorine-based gas: oxygen, hydrogen, helium, and argon. By utilizing dry etching, the exposed areas of sacrificial layers 158R, 158G, and 158B can be formed with good in-plane uniformity.
[0461] As a dry etching apparatus, a dry etching apparatus with a high-density plasma source can be used. For example, an inductively coupled plasma (ICP) etching apparatus can be used as a dry etching apparatus with a high-density plasma source. Alternatively, a capacitively coupled plasma (CCP) etching apparatus including parallel plate-shaped electrodes can be used. The capacitively coupled plasma etching apparatus including parallel plate-shaped electrodes can also employ a structure in which a high-frequency voltage is applied to one of the parallel plate-shaped electrodes. Alternatively, a structure in which multiple different high-frequency voltages are applied to one of the parallel plate-shaped electrodes can be used. Alternatively, a structure in which high-frequency voltages of the same frequency are applied to each of the parallel plate-shaped electrodes can be used. Alternatively, a structure in which high-frequency voltages of different frequencies are applied to each of the parallel plate-shaped electrodes can be used.
[0462] Furthermore, during dry etching, byproducts generated during the process may sometimes be deposited on the top and sides of the insulating layer 127a. As a result, components of the etching gas, the inorganic insulating film 125f, and the sacrificial layers 158R, 158G, and 158B may sometimes be included in the insulating layer 127 after the display device is completed.
[0463] Furthermore, wet etching is preferred for the first etching process. Compared to dry etching, wet etching further reduces damage to the organic compound layers 103R, 103G, and 103B. For example, wet etching can be performed using an alkaline solution. For instance, TMAH of an alkaline solution can be used in the wet etching of the alumina film. In this case, wet etching can be performed by coating. When the inorganic insulating film 125f is deposited using the same material as the sacrificial layers 158R, 158G, and 158B, the above etching process can be performed in a single step, which is therefore preferred.
[0464] In the first etching process, the sacrificial layers 158R, 158G, and 158B are not completely removed, and the etching process is stopped while they are exposed. In this way, by leaving the corresponding sacrificial layers 158R, 158G, and 158B on the organic compound layers 103R, 103G, and 103B, damage to the organic compound layers 103R, 103G, and 103B can be prevented in subsequent processing steps.
[0465] Next, the entire substrate is preferably exposed to visible or ultraviolet light onto the insulating layer 127a. The energy density of this exposure is preferably higher than 0 mJ / cm². 2And it is 800mJ / cm 2 Below, a value higher than 0 mJ / cm is preferred. 2 And it is 500mJ / cm 2 The following applies. By performing this exposure after development, the transparency of the insulating layer 127a can sometimes be improved. Additionally, the substrate temperature required for the subsequent heat treatment to deform the insulating layer 127a into a conical shape can sometimes be reduced.
[0466] Here, by providing oxygen-barrier insulating layers (such as an alumina film) as sacrificial layers 158R, 158G, and 158B, oxygen diffusion to the organic compound layers 103R, 103G, and 103B can be suppressed. When light (visible light or ultraviolet light) is irradiated onto the organic compound layers, the organic compounds contained in these layers may become excited and promote reaction with oxygen in the atmosphere. Specifically, when light (visible light or ultraviolet light) is irradiated onto the organic compound layers in an oxygen-containing atmosphere, oxygen may bond to the organic compounds contained in these layers. By providing sacrificial layers 158R, 158G, and 158B on the island-like organic compound layers, the bonding of oxygen in the atmosphere to the organic compounds contained in these layers can be suppressed.
[0467] Next, a heat treatment (also known as post-baking) is performed. This heat treatment deforms the insulating layer 127a into an insulating layer 127 with a tapered shape on its sides. Figure 8C The heat treatment is performed at a temperature lower than the heat resistance temperature of the organic compound layer. The heat treatment can be performed at a substrate temperature of 50°C 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 130°C or lower. The heating atmosphere can be either atmospheric or an inert gas. Alternatively, the heating atmosphere can be either atmospheric or a reduced pressure atmosphere. In this heat treatment process, it is preferable to increase the substrate temperature compared to the heat treatment (pre-baking) after the formation of the insulating film 127f. This improves the adhesion between the insulating layer 127 and the inorganic insulating layer 125, and also improves the corrosion resistance of the insulating layer 127.
[0468] By leaving sacrificial layers 158R, 158G, and 158B exposed in the first etching process, damage and deterioration of the organic compound layers 103R, 103G, and 103B during the heat treatment can be prevented. This improves the reliability of the light-emitting device.
[0469] Note that, depending on the material of the insulating layer 127 and the temperature, time, and atmosphere of the post-baking process, the side surface of the insulating layer 127 may sometimes form a concave curved shape. For example, the higher the temperature or the longer the time in the post-baking conditions, the more easily the shape of the insulating layer 127 changes, thus sometimes forming a concave curved shape.
[0470] Next, as Figure 9A As shown, the insulating layer 127 is used as a mask for etching, removing a portion of the sacrificial layers 158R, 158G, and 158B. Note that a portion of the inorganic insulating layer 125 is sometimes also removed. This creates openings in the sacrificial layers 158R, 158G, and 158B, exposing the top surfaces of the organic compound layers 103R, 103G, 103B, and the conductive layer 152C. Hereinafter, the etching process using the insulating layer 127 as a mask is sometimes referred to as the second etching process.
[0471] The ends of the inorganic insulating layer 125 are covered by the insulating layer 127. Additionally, Figure 9A An example is shown where a portion of the end of the sacrificial layer 158G (specifically, the tapered portion formed by the first etching process) is covered by the insulating layer 127 and the tapered portion formed by the second etching process is exposed.
[0472] When the inorganic insulating layer 125 and the mask layer are etched in a single process after post-baking without a first etching process, voids may sometimes form as the inorganic insulating layer 125 and the mask layer below the end of the insulating layer 127 disappear due to lateral etching. These voids create unevenness on the surface where the common electrode 155 is formed, making it prone to breakage. Even if voids are formed due to lateral etching of the inorganic insulating layer 125 and the mask layer after the first etching process, these voids can be filled by the insulating layer 127 during subsequent post-baking. Furthermore, since the mask layer is etched in the second etching process, the amount etched laterally is small, making voids less likely to form, and even if voids do form, they are extremely small. Therefore, the surface where the common electrode 155 is formed can be made flatter.
[0473] The insulating layer 127 may also cover the entire end of the sacrificial layer 158G. For example, the end of the insulating layer 127 may sometimes droop down and cover the end of the sacrificial layer 158G. Additionally, for example, the end of the insulating layer 127 may sometimes contact the top surface of at least one of the organic compound layers 103R, 103G, and 103B. As described above, the shape of the insulating layer 127 can sometimes be easily varied when the insulating layer 127a is not exposed after development.
[0474] The second etching process is performed using wet etching. Compared to dry etching, wet etching further reduces damage to the organic compound layers 103R, 103G, and 103B. Wet etching can be performed using an alkaline solution such as TMAH.
[0475] On the other hand, during the second etching process using wet etching, if gaps exist at the interfaces between the organic compound layer 103 and the sacrificial layer 158, between the organic compound layer 103 and the inorganic insulating layer 125, and between the organic compound layer 103 and the insulating layer 175 due to issues such as the adhesion between the organic compound layer 103 and other layers, the chemical solution used in the second etching process may sometimes enter these gaps and contact the pixel electrode. Here, when the chemical solution contacts both conductive layers 151 and 152, the conductive layer with the lower natural potential may sometimes corrode due to galvanic corrosion. For example, when aluminum is used as conductive layer 151 and indium tin oxide is used as conductive layer 152, conductive layer 152 may sometimes corrode. This may reduce the yield of the display device. Furthermore, it may reduce the reliability of the display device.
[0476] As described above, by forming an insulating layer 156 that covers the side surface of the conductive layer 151 and also covers the conductive layers 151 and 152, the inorganic insulating layer 125 can be prevented from breaking. Therefore, for example, it can prevent the solution from contacting the underlying structure such as the conductive layer 151 during the second etching process. As a result, corrosion of the pixel electrode can be prevented.
[0477] As described above, by providing insulating layer 127, inorganic insulating layer 125, sacrificial layer 158R, sacrificial layer 158G, and sacrificial layer 158B, poor connection due to disconnection at the common electrode 155 and increased resistance due to locally thinner sections can be suppressed between the light-emitting devices. Therefore, the display device according to one aspect of the present invention can improve display quality.
[0478] Alternatively, a heat treatment may be performed after a portion of the organic compound layers 103R, 103G, and 103B has been exposed. This heat treatment removes water contained in each organic compound layer and water adsorbed on the surface of each organic compound layer. Furthermore, the shape of the insulating layer 127 may sometimes change due to this heat treatment. Specifically, the insulating layer 127 may sometimes be expanded to cover at least one of the ends of the inorganic insulating layer 125, the ends of the sacrificial layers 158R, 158G, and 158B, and the top surface of the organic compound layers 103R, 103G, and 103B.
[0479] 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 removed. Furthermore, if the heat treatment temperature is too high, deterioration of the organic compound layer 103 and excessive deformation of the insulating layer 127 may occur. Therefore, the heat treatment temperature is preferably higher than the temperature at which water detaches from the organic compound layer 103 and lower than the glass transition temperature of the organic compounds contained in the organic compound layer 103, more preferably lower than the glass transition temperature of the organic compounds contained in the top surface of the organic compound layer 103. Specifically, the substrate temperature is preferably 80°C or higher and 130°C or lower, more preferably 90°C or higher and 120°C or lower, further preferably 100°C or higher and 120°C or lower, and even more preferably 100°C or higher and 110°C or lower. The heating atmosphere can be either atmospheric or an inert gas. Note that the heating atmosphere can be atmospheric or depressurized; a depressurized atmosphere is preferred to prevent the re-adsorption of water detached from the organic compound layer 103.
[0480] This heat treatment can effectively remove water contained in each organic compound layer and water adsorbed on the surface of each organic compound layer without causing degradation of the organic compound layers 103R, 103G, and 103B or excessive changes in the shape of the insulating layer 127. This prevents a decline in the performance of the light-emitting device.
[0481] Next, as Figure 9B As shown, a common layer 104 and a common electrode 155 are formed on organic compound layers 103R, 103G, 103B, conductive layer 152C, and insulating layer 127. The common layer 104 and the common electrode 155 can be formed using methods such as sputtering or vacuum evaporation. Alternatively, the common layer 104 can be formed using evaporation and the common electrode 155 can be formed using sputtering.
[0482] Next, as Figure 9C As shown, a protective layer 131 is formed on the common electrode 155. The protective layer 131 can be formed using methods such as vacuum evaporation, sputtering, CVD, or ALD.
[0483] Next, the substrate 120 is bonded to the protective layer 131 using the resin layer 122, thereby manufacturing a display device. As described above, in one embodiment of the manufacturing method of the display device according to the present invention, an insulating layer 156 is provided on the sides of the conductive layer 151 and the conductive layer 152. This improves the yield of the display device and suppresses defects.
[0484] As described above, in one embodiment of the manufacturing method of the display device of the present invention, the island-shaped organic compound layer 103R, island-shaped organic compound layer 103G, and island-shaped organic compound layer 103B are not formed using a high-precision metal mask, but are formed by depositing a film on one surface and then processing it, thus allowing the island-shaped layers to be formed with a uniform thickness. Furthermore, a high-resolution display device or a display device with a high aperture ratio can be achieved. Moreover, even with high resolution or aperture ratio and extremely short distances between sub-pixels, contact between organic compound layers 103R, organic compound layer 103G, and organic compound layer 103B in adjacent sub-pixels can be suppressed. Therefore, leakage current between sub-pixels can be suppressed. Thus, crosstalk can be suppressed, and a display device with extremely high contrast can be achieved. Additionally, a display device that exhibits good characteristics even when including tandem light-emitting devices manufactured using lithography technology can be provided.
[0485] The structure of this embodiment can be appropriately combined with the structures of other embodiments.
[0486] Implementation Method 4
[0487] In this embodiment, refer to Figures 10A to 10G as well as Figures 11A to 11I This invention describes a light-emitting device according to one aspect of the present invention.
[0488] [Pixel layout]
[0489] In this embodiment, the main description is related to Figure 3A Different pixel layouts. There are no particular restrictions on the arrangement of subpixels; various arrangement methods can be used. Examples of subpixel arrangements include stripe arrangements, S-stripes, matrix arrangements, Delta arrangements, Bayer arrangements, and Pentile arrangements.
[0490] In this embodiment, the top surface shape of the sub-pixel shown in the accompanying drawings corresponds to the top surface shape of the light-emitting region.
[0491] In addition, the top surface shape of a sub-pixel can be, for example, a triangle, a quadrilateral (including a rectangle and a square), a pentagon or other polygons, the aforementioned polygonal shapes with rounded corners, an ellipse or a circle, etc.
[0492] Furthermore, the circuit layout constituting the sub-pixel is not limited to the range of the sub-pixel shown in the attached figure, and can also be arranged outside of it.
[0493] Figure 10A The pixel 178 shown is arranged in an S-stripes pattern. Figure 10A The pixel 178 shown is composed of three sub-pixels: sub-pixel 110R, sub-pixel 110G, and sub-pixel 110B.
[0494] Figure 10B The pixel 178 shown includes sub-pixels 110R (approximately trapezoidal or triangular with rounded corners), 110G (approximately trapezoidal or triangular with rounded corners), and 110B (approximately quadrilateral or hexagonal with rounded corners). Furthermore, the light-emitting area of sub-pixel 110R is larger than that of sub-pixel 110G. Thus, the shape and size of each sub-pixel can be determined independently. For example, the size of sub-pixels including highly reliable light-emitting devices can be smaller.
[0495] Figure 10C Pixels 124a and 124b shown are arranged in a Pentile pattern. Figure 10C In the example shown, pixel 124a, which includes sub-pixels 110R and 110G, and pixel 124b, which includes sub-pixels 110G and 110B, are alternately configured.
[0496] Figures 10D to 10F Pixels 124a and 124b are arranged in a Delta pattern. Pixel 124a includes two sub-pixels (sub-pixels 110R and 110G) in the top row (first row) and one sub-pixel (sub-pixel 110B) in the bottom row (second row). Pixel 124b includes one sub-pixel (sub-pixel 110B) in the top row (first row) and two sub-pixels (sub-pixels 110R and 110G) in the bottom row (second row).
[0497] Figure 10D This shows an example where each sub-pixel has an approximately quadrilateral top surface shape with rounded corners. Figure 10E This shows an example where each sub-pixel has a circular top surface shape. Figure 10F This example shows an example where each sub-pixel has an approximately hexagonal top surface shape with rounded corners.
[0498] exist Figure 10F In this configuration, each subpixel is positioned inside a tightly packed hexagonal region. Each subpixel is arranged such that it is surrounded by six other subpixels when viewed from within. Furthermore, subpixels that emit the same color of light are arranged so that they are not adjacent to each other. For example, each subpixel is arranged such that three subpixels 110G and three subpixels 110B are alternately arranged around subpixel 110R when viewed from within.
[0499] Figure 10G An example is shown where the subpixels of each color are configured in a zigzag shape. Specifically, when viewed from above, the upper positions of two subpixels arranged in the row direction (e.g., subpixel 110R and subpixel 110G or subpixel 110G and subpixel 110B) are offset.
[0500] exist Figures 10A to 10GOf the pixels shown, for example, it is preferable to set subpixel 110R as subpixel R that emits red light, subpixel 110G as subpixel G that emits green light, and subpixel 110B as subpixel B that emits blue light. Note that the structure of the subpixels is not limited to this, and the color emitted by the subpixels and their arrangement order can be appropriately determined. For example, subpixel 110G can also be set as subpixel R that emits red light, and subpixel 110R can be set as subpixel G that emits green light.
[0501] In photolithography, the finer the pattern being processed, the more significant the effect of light diffraction becomes. Therefore, the fidelity of the photomask pattern deteriorates during exposure transfer, making it difficult to process the resist mask into the desired shape. Consequently, even if the photomask pattern is rectangular, it is easy to form a pattern with rounded corners. Thus, the top surface shape of a subpixel sometimes has rounded polygonal, elliptical, or circular shapes, etc.
[0502] Furthermore, in one embodiment of the manufacturing method of the light-emitting device of the present invention, an organic compound layer is processed into an island shape using a photoresist mask. The photoresist 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 organic compound layer material and the curing temperature of the photoresist material, the curing of the photoresist film is sometimes insufficient. The insufficiently cured photoresist film sometimes takes on a shape far from the desired shape during processing. As a result, the top surface shape of the organic compound layer sometimes has a polygonal shape with rounded corners, an ellipse, or a circle, etc. For example, when a photoresist mask with a square top surface shape is to be formed, sometimes a photoresist mask with a circular top surface shape is formed, and the top surface shape of the organic compound layer is circular.
[0503] To ensure the top surface of the organic compound layer has the desired shape, a technique called OPC (Optical Proximity Correction) can be used to pre-correct the mask pattern in a manner that aligns the design pattern with the transfer pattern. Specifically, in OPC, for example, correction patterns are added to the corners of the pattern on the mask pattern.
[0504] like Figures 11A to 11I As shown, a pixel can include four types of sub-pixels.
[0505] Figures 11A to 11C The pixel 178 shown is arranged in stripes.
[0506] Figure 11A This shows an example where each sub-pixel has a rectangular top surface shape. Figure 11B This shows an example where each sub-pixel has a top surface shape that connects two semicircles and a rectangle. Figure 11C This shows an example where each sub-pixel has an elliptical top surface shape.
[0507] Figures 11D to 11F The 178 pixels shown are arranged in a matrix.
[0508] Figure 11D This shows an example where each sub-pixel has a square top surface shape. Figure 11E This example shows an instance where each sub-pixel has an approximately square top surface shape with rounded corners. Figure 11F This shows an example where each sub-pixel has a circular top surface shape.
[0509] Figure 11G and Figure 11H This shows an example of a pixel 178 arranged in two rows and three columns.
[0510] Figure 11G The pixel 178 shown includes 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 includes subpixel 110R in the left column (first column), subpixel 110G in the middle column (second column), subpixel 110B in the right column (third column), and subpixel 110W across these three columns.
[0511] Figure 11H The pixel 178 shown includes three sub-pixels (sub-pixels 110R, 110G, and 110B) in the top row (first row) and three sub-pixels 110W in the bottom row (second row). In other words, pixel 178 includes sub-pixels 110R and 110W in the left column (first column), sub-pixels 110G and 110W in the middle column (second column), and sub-pixels 110B and 110W in the right column (third column). Figure 11H As shown, by aligning the configuration of the up and down sub-pixels, dust that may be generated during the manufacturing process can be efficiently removed, for example. This provides a light-emitting device with high display quality.
[0512] exist Figure 11G and Figure 11H In the pixel 178 shown, the sub-pixels 110R, 110G, and 110B are arranged in a striped pattern, which can improve the display quality.
[0513] Figure 11I This shows an example of a pixel 178 arranged in three rows and two columns.
[0514] Figure 11IThe pixel 178 shown includes 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 subpixel 110W in the bottom row (third row). In other words, pixel 178 includes subpixels 110R and 110G in the left column (first column), subpixel 110B in the right column (second column), and subpixel 110W across both columns.
[0515] exist Figure 11I In the pixel 178 shown, the layout of sub-pixels 110R, 110G, and 110B is a so-called S-striped arrangement, which can improve the display quality.
[0516] Figures 11A to 11I Pixel 178 shown is composed of four sub-pixels: sub-pixel 110R, sub-pixel 110G, sub-pixel 110B, and sub-pixel 110W. For example, sub-pixel 110R can be set to emit red light, sub-pixel 110G can be set to emit green light, sub-pixel 110B can be set to emit blue light, and sub-pixel 110W can be set to emit white light. Alternatively, at least one of sub-pixels 110R, 110G, 110B, and 110W can be set to emit cyan light, magenta light, yellow light, or near-infrared light.
[0517] As described above, in one aspect of the light-emitting device of the present invention, various layouts can be adopted for pixels composed of sub-pixels including light-emitting devices.
[0518] This embodiment can be appropriately combined with other embodiments or examples. Furthermore, where multiple structural examples are shown in one embodiment in this specification, these structural examples can be appropriately combined.
[0519] Implementation Method 5
[0520] In this embodiment, a display device according to one aspect of the present invention will be described.
[0521] The display device in this embodiment can be a high-definition display device. Therefore, for example, the display device in this embodiment can be used as the display unit of information terminal devices (wearable devices) such as watch-type and bracelet-type devices, as well as the display unit of wearable devices that can be worn on the head, such as head-mounted displays (HMDs) for VR devices and glasses-type AR devices.
[0522] Furthermore, the display device in this embodiment can be a high-resolution display device or a large-screen display device. Therefore, the display device in this embodiment can be used, for example, as a display unit for devices such as: electronic devices with large screens, such as television sets, desktop or laptop personal computers, monitors for computers, digital signage, and large game machines such as pinball machines; digital cameras; digital video cameras; digital photo frames; mobile phones; portable game consoles; portable information terminals; and sound reproduction devices.
[0523] [Display Module]
[0524] Figure 12A A perspective view of display module 280 is shown. Display module 280 includes display device 100A and FPC 290. Note that the display device included in display module 280 is not limited to display device 100A, but may be any of display devices 100B to 100E, which will be described later.
[0525] The display module 280 includes a substrate 291 and a substrate 292. The display module 280 includes a display section 281. The display section 281 is the image display area in the display module 280, and can display light from each pixel disposed in the pixel section 284.
[0526] Figure 12B This is a three-dimensional schematic diagram of the structure on one side of the substrate 291. A circuit section 282, a pixel circuit section 283 on the circuit section 282, and a pixel section 284 on the pixel circuit section 283 are stacked on the substrate 291. Furthermore, a terminal section 285 for connecting to the FPC 290 is provided on a portion of the substrate 291 that does not overlap with the pixel section 284. The terminal section 285 is electrically connected to the circuit section 282 via a wiring section 286 composed of multiple wirings.
[0527] The pixel unit 284 includes a plurality of pixels 284a arranged periodically. Figure 12B The right side shows an enlarged view of pixel 284a. Pixel 284a can adopt various structures described in the above embodiments.
[0528] The pixel circuit section 283 includes a plurality of pixel circuits 283a arranged periodically.
[0529] A pixel circuit 283a controls the driving of multiple elements included in a pixel 284a.
[0530] The circuit section 282 includes circuitry for driving each pixel circuit 283a of the pixel circuit section 283. For example, it preferably includes one or both of a gate line driving circuit and a source line driving circuit. Furthermore, it may include at least one of an arithmetic circuit, a storage circuit, and a power supply circuit.
[0531] The FPC290 is used for wiring to supply video signals or power potentials to the circuit section 282 from the outside. Additionally, ICs can be mounted on the FPC290.
[0532] The display module 280 can adopt a structure in which one or both of the pixel circuit section 283 and the circuit section 282 are stacked on the lower side of the pixel section 284, so that the display section 281 can have an extremely high aperture ratio (effective display area ratio).
[0533] This high-definition display module 280 is suitable for use in VR devices such as HMDs or glasses-type AR devices. For example, because the display module 280 has an extremely high-definition display section 281, even when the user views the display section of the display module 280 through a lens and magnifies the display section with the lens, the pixels are not visible, thereby achieving a highly immersive display. Furthermore, the display module 280 can also be applied to electronic devices with relatively small display sections.
[0534] [Display Device 100A]
[0535] Figure 13A The display device 100A shown includes a substrate 301, light-emitting devices 130R, 130G, 130B, a capacitor 240, and a transistor 310.
[0536] Substrate 301 is equivalent to Figure 12A and Figure 12B The substrate 291 is used in the transistor 310. The transistor 310 is a transistor having 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 portion of the substrate 301, a conductive layer 311, a low-resistance region 312, an insulating layer 313, and an insulating layer 314. The conductive layer 311 serves as the gate electrode. The insulating layer 313 is located between the substrate 301 and the conductive layer 311 and serves as the gate insulating layer. The low-resistance region 312 is a region in the substrate 301 doped with impurities and serves as the source or drain. The insulating layer 314 covers the sides of the conductive layer 311.
[0537] In addition, a component separation layer 315 is provided between two adjacent transistors 310 in a manner embedded in the substrate 301.
[0538] In addition, an insulating layer 261 is provided to cover the transistor 310, and a capacitor 240 is provided on the insulating layer 261.
[0539] The capacitor 240 includes a conductive layer 241, a conductive layer 245, and an insulating layer 243 located therebetween. The conductive layer 241 serves as one electrode in the capacitor 240, the conductive layer 245 serves as the other electrode in the capacitor 240, and the insulating layer 243 serves as the dielectric of the capacitor 240.
[0540] A conductive layer 241 is disposed on an insulating layer 261 and embedded within an insulating layer 254. The conductive layer 241 is electrically connected to one of the source and drain terminals of the transistor 310 via a connector 271 embedded in the insulating layer 261. An insulating layer 243 is disposed to cover the conductive layer 241. A conductive layer 245 is disposed in the region where it overlaps with the conductive layer 241, separated by the insulating layer 243.
[0541] An insulating layer 255 is provided to cover the capacitor 240, and an insulating layer 174 is provided on the insulating layer 255. Light-emitting devices 130R, 130G, and 130B are provided on the insulating layer 175. Insulators are provided in the areas between adjacent light-emitting devices.
[0542] An insulating layer 156R is provided to cover the side surface of conductive layer 151R, an insulating layer 156G is provided to cover the side surface of conductive layer 151G, and an insulating layer 156B is provided to cover the side surface of conductive layer 151B. Furthermore, a conductive layer 152R is provided to cover conductive layer 151R and insulating layer 156R, a conductive layer 152G is provided to cover conductive layer 151G and insulating layer 156G, and a conductive layer 152B is provided to cover conductive layer 151B and insulating layer 156B. A sacrificial layer 158R is located on organic compound layer 103R, a sacrificial layer 158G is located on organic compound layer 103G, and a sacrificial layer 158B is located on organic compound layer 103B.
[0543] Conductive layers 151R, 151G, and 151B are electrically connected to one of the source and drain terminals of transistor 310 via plugs 256 embedded in insulating layers 243, 255, 174, and 175, conductive layer 241 embedded in insulating layer 254, and plug 271 embedded in insulating layer 261. The plugs can be made of various conductive materials.
[0544] Furthermore, a protective layer 131 is provided on the light-emitting devices 130R, 130G, and 130B. The substrate 120 is attached to the protective layer 131 by a resin layer 122. Detailed descriptions of the constituent elements of the light-emitting devices 130 and 120 can be found in Embodiment 4. The substrate 120 corresponds to... Figure 12A Substrate 292.
[0545] Figure 13B Show Figure 13A A modified example of the display device 100A shown. Figure 13B The display device shown includes a color layer 132R, a color layer 132G, and a color layer 132B, and a light-emitting device 130 has a region overlapping one of the color layers 132R, 132G, and 132B. Figure 13B In the display device shown, the light-emitting device 130 can emit white light, for example. In addition, for example, the color layer 132R, color layer 132G and color layer 132B can transmit red light, green light and blue light, respectively.
[0546] [Display device 100B]
[0547] Figure 14 A perspective view of the display device 100B is shown. Figure 15 A cross-sectional view of the display device 100C is shown.
[0548] The display device 100B has a structure that bonds substrate 352 and substrate 351. Figure 14 In the image, substrate 352 is represented by a dashed line.
[0549] The display device 100B includes a pixel unit 177, a connection unit 140, a circuit 356, and wiring 355, etc. Figure 14 An example is shown where display device 100B is equipped with IC354 and FPC353. Therefore, it is also possible to... Figure 14 The structure shown is referred to as a display module including a display device 100B, an IC (integrated circuit), and an FPC. Here, the substrate of the display device on which connectors such as the FPC are mounted, or the substrate on which the IC is mounted, is referred to as the display module.
[0550] The connecting portion 140 is disposed on the outer side of the pixel portion 177. There may be one or more connecting portions 140. In the connecting portion 140, the common electrode of the light-emitting device is electrically connected to the conductive layer, and power can be supplied to the common electrode.
[0551] For example, a scan line drive circuit can be used as circuit 356.
[0552] Wiring 355 has the function of supplying signals and power to pixel unit 177 and circuit 356. The signals and power are input to wiring 355 from the outside via FPC 353 or from IC 354.
[0553] Figure 14An example is shown where IC 354 is mounted on substrate 351 using methods such as COG (Chip On Glass) or COF (Chip On Film). IC 354 can be, for example, an IC including scan line drive circuitry or signal line drive circuitry. Note that the display device 100B and display module do not necessarily need to have an IC mounted on them. Alternatively, the IC can be mounted on an FPC using a COF method, for example.
[0554] Figure 15 As shown in display device 100C Figure 14 An example of a cross-section of a display device 100B including a portion of an area of FPC 353, a portion of circuitry 356, a portion of pixel portion 177, a portion of connection portion 140, and a portion of an area including an end portion.
[0555] [Display Device 100C]
[0556] Figure 15 The display device 100C shown includes transistors 201 and 205, a light-emitting device 130R that emits red light, a light-emitting device 130G that emits green light, and a light-emitting device 130B that emits blue light, etc., between substrates 351 and 352.
[0557] For details on light-emitting devices 130R, 130G, and 130B, please refer to Embodiment 4.
[0558] Light-emitting device 130R includes a conductive layer 224R, a conductive layer 151R on the conductive layer 224R, and a conductive layer 152R on the conductive layer 151R. Light-emitting device 130G includes a conductive layer 224G, a conductive layer 151G on the conductive layer 224G, and a conductive layer 152G on the conductive layer 151G. Light-emitting device 130B includes a conductive layer 224B, a conductive layer 151B on the conductive layer 224B, and a conductive layer 152B on the conductive layer 151B.
[0559] The conductive layer 224R is connected to the conductive layer 222b included in the transistor 205 through an opening provided in the insulating layer 214. The end of the conductive layer 151R is located outside the end of the conductive layer 224R. The insulating layer 156R is provided in such a way that it includes a region that contacts the side of the conductive layer 151R, and the conductive layer 152R is provided in such a way that it covers the conductive layer 151R and the insulating layer 156R.
[0560] The conductive layers 224G, 151G, 152G, and 156G in the light-emitting device 130G, and the conductive layers 224B, 151B, 152B, and 156B in the light-emitting device 130B, are the same as the conductive layers 224R, 151R, 152R, and 156R in the light-emitting device 130R, so detailed descriptions are omitted.
[0561] The conductive layers 224R, 224G, and 224B have recesses formed in a manner that cover the openings provided in the insulating layer 214. These recesses are filled with layer 128.
[0562] Layer 128 has the function of filling the recesses of conductive layers 224R, 224G, and 224B to planarize them. Conductive layers 151R, 151G, and 151B, which are electrically connected to conductive layers 224R, 224G, and 224B, are disposed on conductive layers 224R, 224G, and 224B. Therefore, the area overlapping the recesses of conductive layers 224R, 224G, and 224B can also be used as a light-emitting area, which can improve the pixel aperture ratio.
[0563] Layer 128 can also be an insulating layer or a conductive layer. Various inorganic insulating materials, organic insulating materials, and conductive materials can be suitably used for layer 128. In particular, layer 128 is preferably formed using an insulating material, and more preferably using an organic insulating material. Layer 128 can, for example, use the organic insulating material described above that can be used in insulating layer 127.
[0564] A protective layer 131 is provided on light-emitting devices 130R, 130G, and 130B. The protective layer 131 and the substrate 352 are bonded together by an adhesive layer 142. A light-shielding layer 157 is provided on the substrate 352. The light-emitting device 130 can be sealed using a solid sealing structure or a hollow sealing structure, etc. Figure 15 In this configuration, the space between substrates 352 and 351 is filled with adhesive layer 142, thus employing a solid sealing structure. Alternatively, an inert gas (such as nitrogen or argon) can be used to fill the space, resulting in a hollow sealing structure. In this case, adhesive layer 142 can also be configured in a frame shape to avoid overlapping with the light-emitting device. Alternatively, a resin different from the frame-shaped adhesive layer 142 can be used to fill the space.
[0565] Figure 15An example is shown below: the connecting portion 140 includes a conductive layer 224C formed by processing a conductive film identical to that of conductive layers 224R, 224G, and 224B; a conductive layer 151C formed by processing a conductive film identical to that of conductive layers 151R, 151G, and 151B; and a conductive layer 152C formed by processing a conductive film identical to that of conductive layers 152R, 152G, and 152B. Additionally, Figure 15 An example is shown in which the insulating layer 156C is disposed in such a way that it covers the side of the conductive layer 151C.
[0566] Display device 100C is a top-emitting display device. The light-emitting device emits light onto one side of substrate 352. Substrate 352 is preferably made of a material with high transmittance to visible light. Pixel electrodes contain a material that reflects visible light, and counter electrodes (common electrodes 155) contain a material that transmits visible light.
[0567] Insulating layers 211, 213, 215, and 214 are sequentially disposed on substrate 351. A portion of insulating layer 211 serves as the gate insulating layer for each transistor. A portion of insulating layer 213 serves as the gate insulating layer for each transistor. Insulating layer 215 is disposed to cover the transistor. Insulating layer 214 is disposed to cover the transistor and serves as a planarization layer. Furthermore, there is no particular limitation on the number of gate insulating layers and the number of insulating layers covering the transistor; there can be one or more.
[0568] Inorganic insulating films are preferably used as insulating layers 211, 213 and 215.
[0569] The insulating layer 214 used as the planarization layer is preferably an organic insulating layer.
[0570] Transistor 201 and transistor 205 include: a conductive layer 221 serving as a gate; an insulating layer 211 serving as a gate insulating layer; conductive layers 222a and 222b serving as source and drain; a semiconductor layer 231; an insulating layer 213 serving as a gate insulating layer; and a conductive layer 223 serving as a gate.
[0571] A connection portion 204 is provided in a region of substrate 351 that is not overlapped with substrate 352. In the connection portion 204, the source or drain electrode of transistor 201 is electrically connected to FPC 353 via conductive layer 166 and connection layer 242. An example is shown where conductive layer 166 has a stacked structure comprising a conductive film formed by processing conductive films identical to conductive layers 224R, 224G, and 224B; a conductive film formed by processing conductive films identical to conductive layers 151R, 151G, and 151B; and a conductive film formed by processing conductive films identical to conductive layers 152R, 152G, and 152B. Conductive layer 166 is exposed on the top surface of connection portion 204. Therefore, connection portion 204 can be electrically connected to FPC 353 via connection layer 242.
[0572] Preferably, a light-shielding layer 157 is provided on the surface of the substrate 352 on the substrate 351 side. The light-shielding layer 157 can be provided between adjacent light-emitting devices, in the connection portion 140, and in the circuit 356, etc. In addition, various optical components can be arranged on the outer side of the substrate 352.
[0573] Substrate 351 and substrate 352 may each be made of a material that can be used in substrate 120.
[0574] As the adhesive layer 142, a material suitable for the resin layer 122 can be used.
[0575] As the connecting layer 242, anisotropic conductive film (ACF) or anisotropic conductive paste (ACP) can be used.
[0576] [Display Device 100D]
[0577] Figure 16 The display device 100D shown is Figure 15 The main difference between the display device 100C and the display device 100D is that the display device 100D is a bottom-emitting type display device.
[0578] The light emitted by the light-emitting device is directed onto one side of the substrate 351. The substrate 351 is preferably made of a material with high transmittance to visible light. On the other hand, there are no restrictions on the transmittance of the material used for the substrate 352.
[0579] Preferably, a light-shielding layer 317 is formed between the substrate 351 and the transistor 201 and between the substrate 351 and the transistor 205. Figure 16 An example is shown where a light-shielding layer 317 is disposed on a substrate 351, an insulating layer 153 is disposed on the light-shielding layer 317, and transistors 201, 205, etc. are disposed on the insulating layer 153.
[0580] The light-emitting device 130R includes a conductive layer 112R, a conductive layer 126R on the conductive layer 112R, and a conductive layer 129R on the conductive layer 126R.
[0581] The light-emitting device 130B includes a conductive layer 112B, a conductive layer 126B on the conductive layer 112B, and a conductive layer 129B on the conductive layer 126B.
[0582] The conductive layers 112R, 112B, 126R, 126B, 129R, and 129B are all made of materials with high transmittance to visible light. The second electrode 102 is preferably made of a material that reflects visible light.
[0583] Note that, although Figure 16 The light-emitting device 130G is not shown in the figure, but it is also provided.
[0584] in addition, Figure 16 Examples are shown where the top surface of layer 128 has a flat portion, but there are no particular restrictions on the shape of layer 128.
[0585] [Display Device 100D2]
[0586] Figures 17A to 17C The display device 100D2 shown is related to Figure 16 This is an example of a bottom-emitting display device different from the display device 100D shown. The display device 100D2 differs from the display device 100D in that it includes an organic resin layer 180. Note that in the accompanying drawings, details are sometimes omitted. Figure 16 For symbols representing the same constituent elements, please refer to [link / reference]. Figure 16 The records.
[0587] also, Figure 17B The diagram shows a top view layout of pixels 178 (pixels 178a and 178b) including sub-pixels 110 (sub-pixels 110R, 110G, 110B, and 110W). Figure 17C A top view of the organic resin layer 180 in the region where sub-pixels 110R and 110W, including pixel 178, are formed is shown. Note that the width 110Rw in the light-emitting region of sub-pixel 110R is between the light-shielding layers 317 and 317.
[0588] like Figure 17A As shown, the organic resin layer 180 is disposed on the insulating layer 214. (As indicated...) Figure 17A The area enclosed by the dotted line and Figure 17CAs shown, the organic resin layer 180 includes, at least in the region where the sub-pixel is formed, a recess 181 (recess 181a, recess 181b) with a curved surface. Note that the recess 181 may also be disposed outside the light-emitting region, as in the case of recess 181c. By providing this recess 181c, light emitted in the region overlapping with the light-shielding layer 317 or light traveling toward the region overlapping with the light-shielding layer 317 can be refracted and extracted from the light-emitting region to the outside, thereby improving luminous efficiency.
[0589] Alternatively, multiple recesses 181 can be formed in a matrix. Recesses 181a and 181b can be arranged in contact with each other or in a way that creates a plane between them.
[0590] In addition, although Figures 17A to 17C The top surface of the recess is shown to be hexagonal. Figure 17C The cross-sectional shape is semi-circular. Figure 17A However, it can also have other shapes as needed. For example, the top surface shape of the concave part can be a triangle, a quadrilateral (including a rectangle and a square), a pentagon, or other polygons, with the corners of the aforementioned polygons rounded, an ellipse, or a circle.
[0591] As the organic resin layer 180, an insulating layer containing organic materials can be used. For example, acrylic resin, polyimide resin, epoxy resin, imide resin, polyamide resin, polyimide amide resin, silicone resin, siloxane resin, benzocyclobutene resin, phenolic resin, and precursors of the above resins can be used as the organic resin layer 180. Furthermore, as the organic resin layer 180, organic materials such as polyvinyl alcohol (PVA), polyvinyl butyral, polyvinylpyrrolidone, polyethylene glycol, polyglycerol, pullulan, water-soluble cellulose, or alcohol-soluble polyamide resin can also be used.
[0592] Furthermore, a photosensitive resin can also be used as the organic resin layer 180. A photoresist can also be used as the photosensitive resin. The photosensitive resin can be either a positive or negative material.
[0593] The organic resin layer 180 may also contain materials that absorb visible light. For example, the organic resin layer 180 itself may be composed of materials that absorb visible light, and the organic resin layer 180 may also contain pigments that absorb visible light. As the organic resin layer 180, for example, resins that can be used as color filters that transmit red, blue, or green light and absorb other light; or resins that contain carbon black as pigments and are used as black matrices; etc.
[0594] Furthermore, the organic resin layer 180 includes a first electrode 101 (first electrode 101R and first electrode 101W), and the first electrode 101 includes an organic compound layer 103. The ends of the first electrode 101 and the organic compound layer 103 may be covered by an insulating layer 127.
[0595] Furthermore, the first electrode 101 formed on the organic resin layer 180 has a recess along the recess of the organic resin layer 180. Additionally, the organic compound layer 103 formed on the first electrode 101 has a recess along the recess of the first electrode 101. Furthermore, the common layer 104 formed on the organic compound layer 103 has a recess along the recess of the organic compound layer 103. Additionally, the second electrode 102 formed on the common layer 104 has a recess along 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 an overlapping structure.
[0596] Furthermore, a common layer 104 is included on the organic compound layer 103 and the insulating layer 127, and a second electrode 102 is included on the common layer 104. A protective layer 131 is provided on the second electrode 102, which is bonded to the substrate 352 through an adhesive layer 142.
[0597] In addition, although Figures 17A to 17C Light-emitting devices 130G and 130B are not shown, but they are provided.
[0598] [Display Device 100E]
[0599] Figure 18 The display device 100E shown is Figure 15 The main difference between the display device 100E and the display device 100C is that the display device 100E includes color layer 132R, color layer 132G and color layer 132B.
[0600] In the display device 100E, the light-emitting device 130 has a region overlapping one of the coloring layers 132R, 132G, and 132B. The coloring layers 132R, 132G, and 132B can be disposed on a surface of the substrate 352 on one side of the substrate 351. The ends of the coloring layers 132R, 132G, and 132B can overlap the light-shielding layer 157.
[0601] In the display device 100E, the light-emitting device 130 can emit white light, for example. Additionally, for example, the color layers 132R, 132G, and 132B can transmit red light, green light, and blue light, respectively. Alternatively, the display device 100E may also employ a structure in which the color layers 132R, 132G, and 132B are disposed between the protective layer 131 and the adhesive layer 142.
[0602] [Display Device 100E2]
[0603] Figures 19A to 19C The display device 100E2 shown is Figure 18 The illustrated modified example of the display device 100E includes microlenses 182 on color layers 132R, 132G, and 132B. Note that in the drawings, details related to microlenses 182 are sometimes omitted. Figure 18 For symbols representing the same constituent elements, please refer to [link / reference]. Figure 18 The records.
[0604] in addition, Figure 19B The diagram shows a top view layout of pixels 178 (pixels 178a and 178b) including sub-pixels 110 (sub-pixels 110R, 110G, and 110B). Figure 19C A top view is shown of the microlens 182 formed in the region comprising sub-pixels 110R, 110G, and 110B, which are included in pixel 178. Note that the area where the common electrode 155 contacts the organic compound layer 103 is the width 110Gw in the light-emitting region of sub-pixel 110G.
[0605] Figure 19A The display device 100E2 shown has a planarization film 143 on a protective layer 131, and color layers 132R, 132G, and 132B on the planarization film 143. A planarization film 144 is provided to cover the color layers 132R, 132G, and 132B. A microlens 182 is provided on the planarization film 144.
[0606] In addition, such as Figure 19C As shown, microlenses 182 can be set in each sub-pixel of the region where sub-pixels are formed.
[0607] Note that, although Figure 19C The top surface of the microlens 182 is shown to be hexagonal, but it can also have other shapes as needed. For example, the top surface shape of the concave portion can be a triangle, a quadrilateral (including a rectangle and a square), a pentagon or other polygonal shape, the above-mentioned polygonal shapes with rounded corners, an ellipse or a circle, etc.
[0608] The microlens 182 can be formed using the same material as the organic resin layer 180.
[0609] This embodiment can be appropriately combined with other embodiments or examples. Furthermore, where multiple structural examples are shown in one embodiment in this specification, these structural examples can be appropriately combined.
[0610] Implementation Method 6
[0611] In this embodiment, an electronic device according to one aspect of the present invention will be described.
[0612] The electronic device of this embodiment includes a light-emitting device according to one aspect of the present invention in its display unit. The light-emitting device according to one aspect of the present invention has high reliability and is easily implemented with high definition and high resolution. Therefore, it can be used in the display units of various electronic devices.
[0613] As electronic devices, in addition to large-screen electronic devices such as television sets, desktop or laptop personal computers, monitors for computers, digital signage, and large game machines such as pinball machines, other examples include digital cameras, digital video cameras, digital photo frames, mobile phones, portable game consoles, portable information terminals, and sound reproduction devices.
[0614] In particular, because the light-emitting device of one aspect of the present invention can improve clarity, it can be suitably used in electronic devices that include a small display section. Examples of such electronic devices include watch-type and bracelet-type information terminal devices (wearable devices), wearable devices that can be worn on the head, VR devices such as head-mounted displays, AR devices such as glasses, and MR (Mixed Reality) devices.
[0615] The light-emitting device of one aspect of the present invention preferably has 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), 8K (7680×4320 pixels), etc. In particular, it is preferred to set the resolution to 4K, 8K or higher. In addition, the pixel density (clarity) of the light-emitting device of one aspect of the present invention is preferably 100ppi or higher, preferably 300ppi or higher, more preferably 500ppi or higher, further preferably 1000ppi or higher, even more preferably 2000ppi or higher, even more preferably 3000ppi or higher, even more preferably 5000ppi or higher, and even more preferably 7000ppi or higher. By using the aforementioned light-emitting device that possesses one or both of the high resolution and high definition, the sense of realism and depth can be further enhanced. Furthermore, there are no particular limitations on the screen ratio (aspect ratio) of the light-emitting device according to one aspect of the present invention. For example, the light-emitting device can adapt to various screen ratios such as 1:1 (square), 4:3, 16:9, and 16:10.
[0616] The electronic device in this embodiment may also include a sensor (which has the function of measuring factors such as force, displacement, position, velocity, acceleration, angular velocity, rotational speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, tilt, vibration, odor, or infrared radiation).
[0617] The electronic device of this embodiment can have various functions. For example, it can have the following functions: displaying various information (static images, dynamic images, text images, etc.) on the display unit; touch panel function; displaying calendar, date, or time, etc.; executing various software (programs); wireless communication function; reading programs or data stored in the storage medium; etc.
[0618] use Figures 20A to 20D This section describes an example of a wearable device that can be worn on the head. These wearable devices have at least one of the following capabilities: the ability to display AR content, VR content, SR (Substitutional Reality) content, and MR content. When an electronic device has the capability to display at least one of AR, VR, SR, and MR content, it can enhance the user's sense of immersion.
[0619] Figure 20A The electronic device 700A shown and Figure 20BThe electronic devices 700B shown include a pair of display panels 751, a pair of frames 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 components 753, a frame 757, and a pair of nose pads 758.
[0620] The display panel 751 can utilize a light-emitting device according to one aspect of the present invention. This enables the realization of a highly reliable electronic device.
[0621] Both electronic devices 700A and 700B can project images displayed on the display panel 751 onto the display area 756 in the optical component 753. Because the optical component 753 is transparent, the user can see the image displayed on the display area by superimposing it with the image seen through the optical component 753. Therefore, both electronic devices 700A and 700B are capable of AR display.
[0622] Both electronic devices 700A and 700B can be equipped with cameras capable of capturing images of the front as imaging units. Furthermore, by incorporating accelerometers such as gyroscopes into both electronic devices 700A and 700B, the orientation of the user's head can be detected, and an image corresponding to that orientation can be displayed on the display area 756.
[0623] The communications unit includes a wireless communication device through which video signals can be supplied, for example. Additionally, a connector capable of connecting cables supplying video signals and power potential may be included, either in place of the wireless communication device or in addition to the wireless communication device.
[0624] In addition, electronic devices 700A and 700B are equipped with batteries that can be charged wirelessly or via wired means, or both.
[0625] The frame 721 may also be equipped with a touch sensor module. The touch sensor module has the function of detecting whether the outer surface of the frame 721 is touched. Through the touch sensor module, various processes can be performed based on user tap or swipe operations. For example, a tap operation can perform processing such as temporarily pausing or replaying a moving image, while a swipe operation can perform processing such as fast forward or rewind. Furthermore, by providing a touch sensor module in each of the two frames 721, the operating range can be expanded.
[0626] Various touch sensors can be used as touch sensor modules. For example, capacitive, resistive, infrared, electromagnetic induction, surface acoustic wave, and optical sensors can be employed. In particular, capacitive or optical sensors are preferred for use in touch sensor modules.
[0627] When using optical touch sensors, photoelectric conversion devices (also known as photoelectric conversion elements) can be used as the light-receiving element. The active layer of the photoelectric conversion device can use one or both of inorganic and organic semiconductors.
[0628] Figure 20C The electronic device 800A shown and Figure 20D The electronic devices 800B shown include a pair of display units 820, a frame 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.
[0629] The display unit 820 can utilize a light-emitting device according to one aspect of the present invention. This allows for the realization of a highly reliable electronic device.
[0630] The display unit 820 is located inside the housing 821 in a position visible through the lens 832. Furthermore, by displaying different images on each of the pair of display units 820, three-dimensional display utilizing parallax can be achieved.
[0631] Both electronic devices 800A and 800B can be referred to as VR-oriented electronic devices. Users who have installed electronic devices 800A or 800B can see the image displayed on the display unit 820 through the lens 832.
[0632] Electronic devices 800A and 800B preferably have a mechanism in which the left and right positions of the lens 832 and the display unit 820 can be adjusted so that the lens 832 and the display unit 820 are in the most suitable position according to the position of the user's eyes. Furthermore, it is preferable to have a mechanism in which the focus is adjusted by changing the distance between the lens 832 and the display unit 820.
[0633] The user can use the mounting unit 823 to attach electronic device 800A or electronic device 800B to their head. For example, in Figure 20C In this case, the mounting part 823 has a shape similar to the temple of an eyeglass (or also called a temple thread, etc.), but is not limited to this. As long as the user can attach it, the mounting part 823 can have a helmet-shaped or strap-shaped shape, for example.
[0634] The imaging unit 825 has the function of acquiring external information. The data acquired by the imaging unit 825 can be output to the display unit 820. An image sensor can be used in the imaging unit 825. In addition, multiple cameras can be set to support various viewing angles such as telephoto and wide-angle.
[0635] Note that the example shown here includes an imaging unit 825, which can be a ranging sensor (hereinafter also referred to as a detection unit) capable of measuring the distance to an object. In other words, the imaging unit 825 is one type of detection unit. For example, an image sensor or a distance image sensor such as LiDAR (Light Detection and Ranging) can be used as the detection unit. By using images acquired by a camera and images acquired by a distance image sensor, more information can be obtained, enabling more precise attitude control.
[0636] The electronic device 800A may also include a vibration mechanism used as a bone conduction headphone. For example, one or more of the display unit 820, the frame 821, and the mounting unit 823 may adopt a structure including this vibration mechanism. Thus, there is no need to separately install audio equipment such as headphones, earphones, or speakers; one can enjoy images and sound simply by installing the electronic device 800A.
[0637] Electronic devices 800A and 800B may also include input terminals. For example, cables supplying image signals from image output devices and power for charging batteries installed in the electronic devices can be connected to the input terminals.
[0638] An electronic device according to one aspect of the present invention may also have the function of wirelessly communicating with the headset 750. The headset 750 includes a communication unit (not shown) and has wireless communication functionality. The headset 750 can receive information (e.g., voice data) from the electronic device via the wireless communication function. For example, Figure 20A The illustrated electronic device 700A has the function of transmitting information to the headset 750 via wireless communication. Additionally, for example... Figure 20C The electronic device 800A shown has the function of sending information to the headset 750 via wireless communication.
[0639] In addition, electronic devices may also include an earphone unit. Figure 20B The illustrated electronic device 700B includes an earphone unit 727. For example, a structure in which the earphone unit 727 and the control unit are connected by a wire can be adopted. A portion of the wiring connecting the earphone unit 727 and the control unit can also be configured inside the housing 721 or the mounting portion 723.
[0640] same, Figure 20DThe illustrated electronic device 800B includes an earphone unit 827. For example, a structure can be adopted in which the earphone unit 827 and the control unit 824 are connected by a wire. A portion of the wiring connecting the earphone unit 827 and the control unit 824 can also be disposed inside the housing 821 or the mounting portion 823. Furthermore, the earphone unit 827 and the mounting portion 823 can also include magnets. Thus, the earphone unit 827 can be magnetically secured to the mounting portion 823, making storage easy, which is preferable.
[0641] Electronic devices may also include an audio output terminal capable of connecting to headphones or headsets. Additionally, electronic devices may include one or both of an audio input terminal and an audio input mechanism. For example, a microphone or other sound-receiving device can be used as an audio input mechanism. By incorporating an audio input mechanism into the electronic device, it can be given a so-called headset function.
[0642] Thus, as an embodiment of the present invention, both eyeglass type (electronic device 700A and electronic device 700B, etc.) and goggle type (electronic device 800A and electronic device 800B, etc.) are preferred electronic devices.
[0643] In addition, one aspect of the present invention allows the electronic device to transmit information to headphones in a wired or wireless manner.
[0644] Figure 21A The electronic device 6500 shown is a portable information terminal device that can be used as a smartphone.
[0645] Electronic device 6500 includes a frame 6501, a display unit 6502, a power button 6503, a button 6504, a speaker 6505, a microphone 6506, a camera 6507, and a light source 6508, etc. The display unit 6502 has a touch panel function.
[0646] The display unit 6502 can use a light-emitting device according to one aspect of the present invention. This allows for the realization of a highly reliable electronic device.
[0647] Figure 21B It is a cross-sectional schematic diagram of one end of the microphone 6506, including the frame 6501.
[0648] A light-transmitting protective component 6510 is provided on one side of the display surface of the frame 6501. The space surrounded by the frame 6501 and the protective component 6510 contains a display panel 6511, an optical component 6512, a touch sensor panel 6513, a printed circuit board 6517, a battery 6518, etc.
[0649] The display panel 6511, optical component 6512, and touch sensor panel 6513 are fixed to the protective component 6510 using an adhesive layer (not shown).
[0650] In the area outside the display unit 6502, a portion of the display panel 6511 is folded back, and this folded portion is connected to an FPC 6515. An IC 6516 is mounted on the FPC 6515. The FPC 6515 is connected to terminals disposed on a printed circuit board 6517.
[0651] The display panel 6511 can use a light-emitting device according to one aspect of the present invention. This allows for the realization of an extremely lightweight electronic device. Furthermore, since the display panel 6511 is extremely thin, a large-capacity battery 6518 can be installed while minimizing the thickness of the electronic device. Additionally, by folding a portion of the display panel 6511 to provide a connection portion with the FPC 6515 on the back of the pixel section, a narrow-bezel electronic device can be achieved.
[0652] Figure 21C An example of a television device is shown. In the television device 7100, a display unit 7000 is assembled in a frame 7171. The structure in which the frame 7171 is supported by a bracket 7173 is shown here.
[0653] The display unit 7000 can use a light-emitting device according to one aspect of the present invention. This allows for the realization of a highly reliable electronic device.
[0654] It can be operated using the operating switch provided in the housing 7171 and the separately provided remote control 7151. Figure 21C The operation of the television device 7100 shown is illustrated. Alternatively, a touch sensor may be provided in the display unit 7000, allowing operation of the television device 7100 by touching the display unit 7000 with a finger or the like. Furthermore, a display unit for displaying data output from the remote control 7151 may be provided in the remote control 7151. Channel and volume adjustments can be made using the operation keys or touch panel provided in the remote control 7151, and the images displayed on the display unit 7000 can also be manipulated.
[0655] In addition, the television device 7100 includes a receiver and a modem. It can receive general television broadcasts using the receiver. Furthermore, it can connect to a wired or wireless communication network via the modem to conduct one-way (from sender to receiver) or two-way (between sender and receiver, or between receivers, etc.) information communication.
[0656] Figure 21D An example of a notebook computer is shown. The notebook computer 7200 includes a chassis 7211, a keyboard 7212, a pointing device 7213, and an external connection port 7214, etc. A display unit 7000 is assembled in the chassis 7211.
[0657] The display unit 7000 can use a light-emitting device according to one aspect of the present invention. This allows for the realization of a highly reliable electronic device.
[0658] Figure 21E and Figure 21F Here is an example of digital signage.
[0659] Figure 21E The digital sign 7300 shown includes a frame 7301, a display unit 7000, and a speaker 7303. It may also include LEDs, operation keys (including a power switch or operation switch), connection terminals, various sensors, a microphone, etc.
[0660] Figure 21F A digital sign 7400 is shown mounted on a cylindrical column 7401. The digital sign 7400 includes a display section 7000 disposed along the curved surface of the column 7401.
[0661] exist Figure 21E and Figure 21F In this embodiment, the light-emitting device according to one aspect of the present invention can be used in the display unit 7000. This allows for the realization of a highly reliable electronic device.
[0662] The larger the display unit (7000), the more information it can provide at once. A larger display unit (7000) is also more likely to attract attention, which can improve the effectiveness of advertising.
[0663] By using a touch panel in the display unit 7000, not only can static or dynamic images be displayed on the display unit 7000, but users can also operate it intuitively, making it preferable. Furthermore, when used to provide information such as route information or traffic information, intuitive operation enhances ease of use.
[0664] like Figure 21E and Figure 21F As shown, digital signage 7300 or digital signage 7400 preferably connects wirelessly with information terminal devices 7311 or 7411, such as smartphones carried by the user. For example, advertising information displayed on display unit 7000 can be displayed on the screen of information terminal device 7311 or information terminal device 7411. Furthermore, the display on display unit 7000 can be switched by operating information terminal device 7311 or information terminal device 7411.
[0665] Furthermore, the game can be executed on the digital signage 7300 or 7400 using the screen of information terminal device 7311 or 7411 as the operating unit (controller). Thus, multiple users can participate in the game simultaneously and enjoy the experience.
[0666] Figures 22A to 22G The electronic device shown includes a frame 9000, a display unit 9001, a speaker 9003, operation keys 9005 (including a power switch or operation switch), a connection terminal 9006, a sensor 9007 (which has the function of measuring the following factors: force, displacement, position, velocity, acceleration, angular velocity, rotational speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, tilt, vibration, odor, or infrared radiation), a microphone 9008, etc.
[0667] Figures 22A to 22G The electronic device shown has various functions. For example, it may have the following functions: displaying various information (still images, moving images, text images, etc.) on a display unit; a touch panel function; displaying a calendar, date, or time; controlling processing using various software (programs); wireless communication function; reading and processing programs or data stored in a storage medium; etc. Note that the functions of the electronic device are not limited to the above functions, but can have various functions. The electronic device may include multiple display units. In addition, a camera or the like may be installed in the electronic device to give it the following functions: capturing still or moving images and storing the captured images in a storage medium (external storage medium or storage medium built into the camera); displaying the captured images on a display unit; etc.
[0668] The following is a detailed explanation. Figures 22A to 22G The electronic device shown.
[0669] Figure 22A This is a perspective view showing a portable information terminal 9171. The portable information terminal 9171 can be used, for example, as a smartphone. Note that a speaker 9003, a connection terminal 9006, a sensor 9007, etc., may also be included in the portable information terminal 9171. Furthermore, as a portable information terminal 9171, text or image information can be displayed on multiple surfaces. Figure 22A The image shows an example displaying three icons 9050. Alternatively, information 9051, shown as a dashed rectangle, can be displayed on other surfaces of the display unit 9001. Examples of information 9051 include notifications of received emails, SNS messages, phone calls, etc.; the subject of the email or SNS message; the sender's name; the date; the time; remaining battery level; and radio wave strength. Alternatively, icons 9050 can be displayed in the same location where information 9051 is displayed.
[0670] Figure 22BThis is a perspective view showing a portable information terminal 9172. The portable information terminal 9172 has the function of displaying information on three or more surfaces of the display unit 9001. Here, examples are shown where information 9052, information 9053, and information 9054 are displayed on different surfaces. For example, when the portable information terminal 9172 is placed in a jacket pocket, the user can check information 9053 displayed in a position visible from above the portable information terminal 9172. For example, the user can check this display without taking the portable information terminal 9172 out of their pocket, thereby determining whether to answer a phone call.
[0671] Figure 22C This is a perspective view of a tablet terminal 9173. The tablet terminal 9173 can, for example, execute various application software such as mobile phone, email, and article reading and editing, music playback, network communication, and computer games. The tablet terminal 9173 includes a display unit 9001, a camera 9002, a microphone 9008, and a speaker 9003 on the front of its housing 9000; operation keys 9005 serving as operating buttons on the left side of the housing 9000; and a connection terminal 9006 on the bottom surface.
[0672] Figure 22D This is a perspective view showing a watch-type portable information terminal 9200. The portable information terminal 9200 can be used, for example, as a smartwatch (registered trademark). Furthermore, the display surface of the display unit 9001 is curved, allowing display along its curved surface. In addition, the portable information terminal 9200 can perform hands-free calls, for example, by communicating with a headset capable of wireless communication. Furthermore, by utilizing the connection terminal 9006, the portable information terminal 9200 can transmit data or charge with other information terminals. Charging can also be performed wirelessly.
[0673] Figures 22E to 22G This is a perspective view showing the foldable portable information terminal 9201. Additionally, Figure 22E This is a 3D view of the portable information terminal 9201 in its unfolded state. Figure 22G It is a 3D image of the folded state. Figure 22F From Figure 22E status and Figure 22G The portable information terminal 9201 is a three-dimensional representation of the state transitioning between different states. In its folded state, it is highly portable, while in its unfolded state, it offers excellent browsing capabilities due to its large, seamlessly integrated display area. The display unit 9001 included in the portable information terminal 9201 is supported by three frames 9000 connected by hinges 9055. The display unit 9001 can be bent, for example, within a radius of curvature of 0.1 mm or more and 150 mm or less.
[0674] This embodiment can be appropriately combined with other embodiments or examples. Furthermore, where multiple structural examples are shown in one embodiment in this specification, these structural examples can be appropriately combined.
[0675] Example 1
[0676] <<Synthesis example 1>>
[0677] In this embodiment, the synthesis method of compound 4,4'-[(1,2-naphthyl)bis(4,1-phenylene)]bis[1]benzofurano[3,2-d]pyrimidine (abbreviated as BfpmP2N), represented by structural formula (100) in Embodiment 1, is specifically described. The structure of BfpmP2N is shown below.
[0678] [Chemical Formula 28]
[0679]
[0680] <Step 1: Synthesis of 4-(4-chlorophenyl)[1]benzofurano[3,2-d]pyrimidine>
[0681] 10 g (50 mmol) of 4-chlorobenzofuran[3,2-d]pyrimidine, 12 g (76 mmol) of 4-chlorophenylboronic acid, 31 g (227 mmol) of potassium carbonate (K₂CO₃), 75 mL of tetrahydrofuran (THF), and 25 mL of water were placed in a 200 mL three-necked flask and degassed by stirring under reduced pressure. The flask was then heated to 60 °C under a nitrogen stream, and 4.4 g (4 mmol) of tetrakis(triphenylphosphine)palladium(O) (abbreviated as Pd(PPh₃)₄) was added. The temperature was then raised to 80 °C and stirred for 10 hours. After the specified time, the mixture was filtered, and the residue was washed with water and ethanol. The residue was purified by silica gel column chromatography with the developing solvent changed from toluene to toluene:ethyl acetate = 15:1. The solid was recrystallized from toluene to give 7.1 g of a yellow solid in 51% yield. The following shows the synthesis scheme (a-1).
[0682] [Chemical Formula 29]
[0683]
[0684] <Step 2: Synthesis of 4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxoboron-2-yl)phenyl][1]benzofurano[3,2-d]pyrimidine>
[0685] 6.4 g (23 mmol) of 4-(4-chlorophenyl)[1]benzofurano[3,2-d]pyrimidine, 8.7 g (34 mmol) of bis(pinacol)diboron, 6.7 g (69 mmol) of potassium acetate (CH3COOK), and 120 mL of xylene were placed in a three-necked flask, and the air in the flask was replaced with nitrogen. Then, the flask was heated to 60 °C under a nitrogen flow, and 1.9 g (2.3 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (abbreviated as: Pd(dppf)2Cl2) was added. CH2Cl2), stirred at 120°C for 5 hours. After stirring, the mixture was filtered to remove impurities. The filtrate was concentrated and purified by silica gel column chromatography with the developing solvent changed from toluene to toluene:ethyl acetate = 5:1, yielding 5.0 g of the target pale yellow solid in 59% yield. The synthetic scheme (a-2) is shown below.
[0686] [Chemical Formula 30]
[0687]
[0688] <Step 3: Synthesis of 4,4'-[(1,2-naphthyl)bis(4,1-phenylene)]bis[1]benzofurano[3,2-d]pyrimidine (abbreviation: BfpmP2N)>
[0689] 1.5 g (5.3 mmol) of 1,2-dibromonaphthalene, 5.0 g (13 mmol) of 4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxoboronyl-2-yl)phenyl][1]benzofurano[3,2-d]pyrimidine obtained in step 2, 4.5 g (32 mmol) of potassium carbonate (K2CO3), 22 mL of toluene, 6 mL of ethanol, and 16 mL of water were placed in a 200 mL three-necked flask. The mixture was stirred under reduced pressure to degas the contents. Then, the flask was heated to 60 °C under a nitrogen stream, and 2.8 g (2.3 mmol) of tetrakis(triphenylphosphine)palladium(0) (abbreviated as Pd(PPh3)4) was added. The temperature was then raised to 90 °C and stirred for 22 hours. After the reaction, the mixture was filtered, and the residue was washed with water and ethanol. The resulting residue was dissolved in toluene by heating to remove insoluble impurities. The concentrated filtrate was purified by silica gel column chromatography with the developing solvent changed from toluene to toluene:ethyl acetate = 4:1. The solid was recrystallized from toluene to give 2.4 g of the target pale yellow solid in 73% yield. The 2.4 g of the obtained solid was purified by sublimation using a gradient sublimation method. The purification was carried out at a pressure of 5.3 × 10⁻⁶. -3Under the conditions of Pa, the mixture was heated at 290 °C for 21 hours. After sublimation purification, 1.9 g of a pale yellow solid of the target compound was obtained with a recovery of 79%. The synthetic scheme (a-3) is shown below.
[0690] [Chemical Formula 31]
[0691]
[0692] In addition, nuclear magnetic resonance (NMR) was used to analyze the protons of the brown solid obtained through the above method. 1 H) was measured. The values obtained are shown below. Figure 23 yes 1 H-NMR spectrum. It can be seen that in this synthetic example 1, a BfpmP2N (abbreviated) of one aspect of the present invention represented by the above structural formula (100) was obtained.
[0693] 1 H-NMR.δ (CDCl3, 500MHz): 9.24 (s, 1H), 9.19 (s, 1H), 8.64 (d, J=8.3Hz, 2H), 8.50 (d, J=8.3Hz, 2H), 8.28-8.24 (m, 2H), 8.0 4 (d, J=8.4Hz, 1H), 7.99 (d, J=8.2Hz, 1H), 7.78 (d, J=8.3Hz, 1H), 7.71-7.66 (m, 5H), 7.58-7.54 (m, 3H), 7.53-7.46 (m, 5H).
[0694] The glass transition temperature (Tg) of BfpmP2N (abbreviated) was measured. The Tg was measured by placing the powder on an aluminum element using a differential scanning calorimeter (DSC8500 manufactured by PerkinElmer Japan Co., Ltd.). The result showed that the Tg of BfpmP2N (abbreviated) was 141℃, indicating that BfpmP2N is an organic compound with good heat resistance and low crystallinity suitable for use in light-emitting devices.
[0695] Example 2
[0696] <<Synthesis example 2>>
[0697] In this embodiment, the synthesis method of compound 4,4'-(1,2-naphthyl)bis[1]benzofurano[3,2-d]pyrimidine (abbreviated as Bfpm2N), represented by structural formula (101) in Embodiment 1, is specifically described. The structure of Bfpm2N is shown below.
[0698] [Chemical Formula 32]
[0699]
[0700] <Step 1: Synthesis of 4,4,5,5-Tetramethyl-2-[1-(4,4,5,5-Tetramethyl-1,3,2-dioxoboropentan-2-yl)-2-naphthyl]-1,3,2-dioxoboropentan>
[0701] 5 g (17 mmol) of 1,2-dibromonaphthalene, 1.3 g (52 mmol) of bis(pinacol)diboron, 10.4 g (105 mmol) of potassium acetate (CH3COOK), and 90 mL of N,N-dimethylformamide (DMF) were placed in a 200 mL three-necked flask. The mixture was stirred under reduced pressure to degas the contents. Then, the flask was heated to 60 °C under a nitrogen stream, and 1.4 g (1.8 mmol) of [1,1'-bis(diphenylphosphine)ferrocene]palladium(II) dichloromethane adduct (Pd(dppf)2Cl2) was added. CH2Cl2), then heated to 100°C and stirred for 6 hours. After the specified time, extraction was performed with toluene, the resulting organic layer was washed with a saturated sodium chloride aqueous solution, and then dried with magnesium sulfate. The mixture was separated by gravity filtration, and the filtrate was concentrated to give a brown oil. The oil was purified by silica gel column chromatography with the developing solvent changed from toluene to toluene:ethyl acetate = 1:1, yielding 5.6 g of a brown solid in 84% yield. The synthetic scheme (b-1) is shown below.
[0702] [Chemical Formula 33]
[0703]
[0704] <Step 2: Synthesis of 4,4'-(1,2-naphthyl)bis[1]benzofurano[3,2-d]pyrimidine (abbreviation: Bfpm2N)>
[0705] 2.9 g (6 mmol) of 4,4,5,5-tetramethyl-2-[1-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-2-naphthyl]-1,3,2-dioxoboronyl, 5.2 g (21 mmol) of 4-chlorobenzofurano[3,2-d]pyrimidine, 7.1 g (52 mmol) of potassium carbonate, 34 mL of toluene, 9 mL of ethanol, and 26 mL of water were placed in a 200 mL three-necked flask and degassed by stirring under reduced pressure. Then, the flask was heated to 60 °C under a nitrogen stream, and 1.2 g (1 mmol) of tetrakis(triphenylphosphine)palladium(O) (abbreviated as Pd(PPh3)4) was added. The temperature was then raised to 90 °C and stirred for 12 hours. After the specified time, the reaction solution was extracted with toluene. After washing the obtained organic layer with water and a saturated sodium chloride aqueous solution, it was dried with magnesium sulfate. The mixture was separated by gravity filtration, and the filtrate was concentrated to give a brown oil. The oil was purified by silica gel column chromatography with the developing solvent changed from toluene to toluene:ethyl acetate = 5:1. The solid was recrystallized from the obtained solid using toluene / ethanol to give 1.2 g of a pale yellow solid in 34% yield. 0.7 g of the obtained solid was purified by sublimation using a gradient sublimation method. The solution was then purified at a pressure of 8.1 × 10⁻⁶. -3 Under the conditions of Pa, the sample was heated at 195°C for 18 hours and then at 205°C for 2 hours. After sublimation purification, 0.6 g of the target compound was obtained as a white solid with a recovery of 76%. The synthetic scheme (b-3) is shown below.
[0706] [Chemical Formula 34]
[0707]
[0708] In addition, nuclear magnetic resonance (NMR) was used to analyze the protons of the brown solid obtained through the above method. 1 H) was measured. The values obtained are shown below. Figure 24 yes 1 H-NMR spectrum. It can be seen that in this synthetic example 2, a Bfpm2N (abbreviated) of one aspect of the present invention represented by the above structural formula (101) was obtained.
[0709] 1 H-NMR.δ (CDCl3, 300MHz): 9.12 (s, 1H), 8.89 (s, 1H), 8.31-8.21 (m, 3H), 8.14- 8.08 (m, 2H), 7.75 (d, J=8.1Hz, 1H), 7.69-7.38 (m, 7H), 7.21 (d, J=8.4Hz, 1H).
[0710] The glass transition temperature (Tg) of Bfpm2N (abbreviated) was measured. The Tg was measured by placing the powder on an aluminum element using a differential scanning calorimeter (DSC8500 manufactured by PerkinElmer Japan Co., Ltd.). The result showed that the Tg of Bfpm2N (abbreviated) was 103℃, indicating that Bfpm2N is an organic compound with good heat resistance and low crystallinity suitable for use in light-emitting devices.
[0711] Example 3
[0712] In this embodiment, a light-emitting device 1A according to one aspect of the present invention is manufactured. Additionally, a comparative light-emitting device 1B is manufactured for characteristic comparison.
[0713] The following shows the structural formulas of the organic compounds used in light-emitting devices 1A and 1B.
[0714] [Chemical Formula 35]
[0715]
[0716] like Figure 25 As shown, each device has the following structure: a hole injection layer 811, a hole transport layer 812, a light-emitting layer 813 and an electron transport layer 814 are sequentially stacked on a first electrode 801 formed on a glass substrate 800, and a second electrode 802 is stacked on the electron transport layer 814.
[0717] <Manufacturing Method of Light Emitting Device 1A>
[0718] The first electrode 801 is formed by depositing indium tin oxide (ITSO) containing silicon oxide to a thickness of 110 nm on a glass substrate 800 using a sputtering method. Note that the electrode area is 4 mm². 2 (2mm×2mm).
[0719] Next, as a pretreatment for forming the light-emitting device on the substrate, the substrate surface was washed with water and baked at 200°C for 1 hour. Then, the substrate was placed inside and the pressure was reduced to 1×10⁻⁶. -4 In a vacuum evaporation apparatus with a pressure of approximately Pa, the sample is vacuum-baked at 170°C for 30 minutes in the heating chamber. Then, it undergoes self-cooling for 45 minutes.
[0720] Next, the substrate on which the first electrode 801 is formed is fixed on a substrate support provided in a vacuum evaporation apparatus with the surface on which the first electrode 801 is formed facing downwards. N-(biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H-fluorene-2-amine (abbreviated as: PCBBiF) and an electron acceptor material (OCHD-003) with a molecular weight of 672 containing fluorine are co-evaporated on the first electrode with a thickness of 10 nm, wherein PCBBiF:OCHD-003 = 1:0.03 (weight ratio), thereby forming a hole injection layer 811.
[0721] Next, PCBBiF is deposited on the hole injection layer 811 with a thickness of 90 nm using a resistance heating evaporation method as the hole transport layer 812_2. Then, N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviated as: DBfBB1TP) is deposited on the hole transport layer 812_1 with a thickness of 10 nm, thereby forming the hole transport layer 812.
[0722] Next, 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviated as αN-βNPAnth) and N,N'-diphenyl-N,N'-bis[(9-phenyl-9H-carbazole-2-yl)]naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviated as 3,10PCA2Nbf(IV)-02) are co-deposited on the hole transport layer 812 using a resistance heating evaporation method to a thickness of 25 nm, wherein αN-βNPAnth:3,10PCA2Nbf(IV)-02=1:0.015 (weight ratio), thereby forming the light-emitting layer 813.
[0723] Next, 4-(biphenyl-4-yl)-6-[3'-(9,9-dimethyl-9H-fluorene-2-yl)biphenyl-4-yl]-2-phenylpyrimidine (abbreviated as: 2Ph-4BP-6pmFBPPm) with a thickness of 10 nm is deposited on the light-emitting layer 813 to form an electron transport layer 814_1. Then, 4,4'-[(1,2-naphthyl)bis(4,1-phenylene)]bis[1]benzofurano[3,2-d]pyrimidine (abbreviated as: BfpmP2N) and 8-hydroxyquinoline-lithium (abbreviated as: Liq) are co-deposited with a thickness of 15 nm to form an electron transport layer 814_2, wherein BfpmP2N:Liq=1:0.5 (weight ratio), thereby forming an electron transport layer 814.
[0724] Next, aluminum (Al) is vapor-deposited on the electron transport layer 814 with a thickness of 100 nm, thereby for...
Claims
1. An organic compound represented by the general formula (G1): , in, Ar 1 and Ar 2 Each can be independently represented as an arylene with 6 to 12 substituted or unsubstituted carbon atoms, or a heteroarylene with 1 to 12 substituted or unsubstituted carbon atoms. n and m represent integers greater than 0 and less than 4, respectively. Bfpm 1 and Bfpm 2 Each can be independently represented by the general formula (g1-1). A can be represented by any one of the general formulas (g2-1) to (g2-6). , X 1 Indicates oxygen or sulfur. R 1 To R 6 Each of the following can be independently represented: hydrogen, alkyl group having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or substituted or unsubstituted heteroaryl group having 1 to 12 carbon atoms. R 1 To R 6 Any one of the representations in Ar is bound to Ar 1 Or Ar 2 The key, , R 10 To R 17 and R 20 To R 75 Each of the following independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 12 carbon atoms, or a group bonded to Ar. 1 Or Ar 2 The key, Furthermore, bonded to Ar 1 and Ar 2 The key is R 10 To R 17 Any two adjacent R 20 To R 29 Any two adjacent R 30 To R 39 Any two adjacent R 40 To R 51 Any two adjacent R 52 To R 63 any two adjacent ones or R 64 To R 75 Any two adjacent ones in the middle.
2. The organic compound according to claim 1, Where R 3 R 5 and R 6 Any one of the representations in Ar is bound to Ar 1 Or Ar 2 The key.
3. An organic compound represented by the general formula (G2): , in, Ar 1 and Ar 2 Each can be independently represented as an arylene with 6 to 12 substituted or unsubstituted carbon atoms, or a heteroarylene with 1 to 12 substituted or unsubstituted carbon atoms. n and m represent integers greater than 0 and less than 4, respectively. X 1 and X 2 Each can be used independently to represent oxygen or sulfur. R 1 To R 5 and R 101 To R 105 Each of the following can be independently represented: hydrogen, alkyl group having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or substituted or unsubstituted heteroaryl group having 1 to 12 carbon atoms. A can be represented by any one of the general formulas (g2-1) to (g2-6). , R 10 To R 17 and R 20 To R 75 Each of the following independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 12 carbon atoms, or a group bonded to Ar. 1 Or Ar 2 The key, Furthermore, bonded to Ar 1 and Ar 2 The key is R 10 To R 17 Any two adjacent R 20 To R 29 Any two adjacent R 30 To R 39 Any two adjacent R 40 To R 51 Any two adjacent R 52 To R 63 any two adjacent ones or R 64 To R 75 Any two adjacent ones in the middle.
4. An organic compound represented by the general formula (G3): , in, Ar 1 and Ar 2 Each can be independently represented as an arylene with 6 to 12 substituted or unsubstituted carbon atoms, or a heteroarylene with 1 to 12 substituted or unsubstituted carbon atoms. n and m represent integers greater than 0 and less than 4, respectively. X 1 and X 2 Each can be used independently to represent oxygen or sulfur. Furthermore, R 1 To R 5 R 12 To R 17 and R 101 To R 105 Each of the following can be independently represented: hydrogen, alkyl group having 1 to 6 carbon atoms, cyclic alkyl group having 3 to 10 carbon atoms (substituted or unsubstituted), aryl group having 6 to 12 carbon atoms (substituted or unsubstituted), or heteroaryl group having 1 to 12 carbon atoms (substituted or unsubstituted).
5. The organic compound according to claim 1, wherein X 1 It is oxygen.
6. The organic compound according to claim 1, wherein both n and m are 1.
7. The organic compound according to claim 1, Where both n and m are 1. And Ar 1 and Ar 2 All are substituted or unsubstituted phenylene compounds.
8. The organic compound according to claim 4, wherein the organic compound is represented by structural formula (100) or structural formula (101): 。 9. A light-emitting device comprising the organic compound of claim 1.
10. The organic compound according to claim 3, wherein X 1 It is oxygen.
11. The organic compound according to claim 3, wherein both n and m are 1.
12. The organic compound according to claim 3, Where both n and m are 1. And Ar 1 and Ar 2 All are substituted or unsubstituted phenylene compounds.
13. A light-emitting device comprising the organic compound of claim 3.
14. The organic compound according to claim 4, wherein X 1 It is oxygen.
15. The organic compound according to claim 4, wherein both n and m are 1.
16. The organic compound according to claim 4, Where both n and m are 1. And Ar 1 and Ar 2 All are substituted or unsubstituted phenylene compounds.
17. A light-emitting device comprising the organic compound of claim 4.
Citation Information
Patent Citations
Function panel, display device, I / O device, information processing device, and method for driving information processing device
WO2020152556A1