Organic compound, light-emitting device, light-emitting device, electronic device, and lighting device
By introducing aryl or heteroaryl substituents into organic compounds and forming a ring structure, the Tg and carrier transportability are improved, the problem of insufficient crystallization and efficiency of light emitting devices at high temperatures is solved, and high heat resistance is achieved Glow efficiently and efficiently.
Patent Information
- Application Number
- CN202410896398.5
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-07-07
- Filing Date
- 2024-07-05
- Publication Date
- 2025-01-07
AI Technical Summary
The easy crystallization of existing organic compounds at high temperatures leads to deterioration of the brightness of the light-emitting device, and the carrier transportability and luminous efficiency are insufficient, making it difficult to meet the requirements of high heat resistance and high-efficiency luminescence.
Using organic compounds with specific structures, the molecular weight and the formation of a ring structure by introducing aryl or heteroaryl substituents, increase the glass transition temperature (Tg) and carrier transportability, and optimize the S1 and T1 energy levels to form high efficiency luminescent layer material.
It achieves high heat resistance, improves the brightness and reliability of the light emitting device, enhances carrier transmission and luminous efficiency, reduces power consumption, and is suitable for blue fluorescent or phosphorescent luminescent layers.
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Figure CN119264174A_ABST
Abstract
Description
Technical Field
[0001] One embodiment of the present invention relates to an organic compound, a light-emitting device, a light-emitting apparatus, a display device, an electronic device, a lighting device, and an electronic device. Note that one embodiment of the present invention is not limited to the above-mentioned technical field. The technical field of one embodiment of the invention disclosed in this specification, etc., relates to an object, a method, or a manufacturing method. In addition, one embodiment of the present invention relates to a process, a machine, a product, or a composition of matter. Therefore, more specifically, as an example of the technical field of one embodiment of the present invention disclosed in this specification, semiconductor devices, display devices, liquid crystal display devices, light-emitting devices, lighting devices, power storage devices, storage devices, camera devices, driving methods of these devices, or manufacturing methods of these devices can be cited. Background Art
[0002] The practical application of light-emitting devices (organic EL devices) using organic compounds and utilizing electroluminescence (EL) is very active. In the basic structure of these light-emitting devices, an organic compound layer (EL layer) containing a light-emitting material is sandwiched between a pair of electrodes. By applying voltage to the device, carriers are injected, and the recombination energy of the carriers is used to obtain light emission from the light-emitting material.
[0003] Because this light-emitting device is a self-luminous light-emitting device, it has advantages such as higher visibility and no need for backlight when used for pixels of a display compared to liquid crystals, so this light-emitting device is suitable for devices used in flat-panel displays. In addition, a display using this light-emitting device can be made thin and light, which is also a great advantage. Furthermore, very high-speed response is also one of the characteristics of this light-emitting device.
[0004] In addition, since the light-emitting layer of these light-emitting devices can be continuously formed in two dimensions, surface light emission can be obtained. Since this is a feature that is difficult to obtain in point light sources represented by incandescent lamps or LEDs or line light sources represented by fluorescent lamps, the above-mentioned light-emitting devices are also highly useful as surface light sources that can be applied to lighting, etc.
[0005] As described above, displays and lighting devices using light-emitting devices can be suitably used in various electronic devices, and research and development are being actively pursued in pursuit of light-emitting devices having better characteristics.
[0006] In order to improve the characteristics of light-emitting devices, there are many problems depending on the materials such as organic compounds, metals, and metal compounds that constitute the light-emitting devices. In order to solve these problems, material development and device structure improvement are being carried out. Patent document 1 discloses a hole transport material, which is an organic compound that can improve the luminous efficiency of the light-emitting device by being used in the light-emitting device.
[0007] In addition, regarding the heat resistance of the light-emitting device, the glass transition temperature (T g ) is not sufficiently high, there is a problem of degradation of the brightness of the light-emitting device due to crystallization or the like.
[0008] [Patent Document 1] Japanese Patent Application Publication No. 2009-298767
[0009] [Non-patent document 1] Nicholas J. Turro, V. Ramamurthy, and JC Scaiano, “MODERN MOLECULAR PHOTOCHEMISTRY OF ORGANIC MOLECULES,” UNIVERSITY SCIENCE BOOKS, published on February 10, 2010, pp. 204-208 [Non-patent document 2] Daisaku TANAKA et al., "Ultra High Efficiency Green Organic Light-Emitting Devices", Japanese Journal of Applied Physics, Vol. 46, No. 1, 2007, pp. L10-L12 Summary of the invention
[0010] As a method for improving the heat resistance of organic compounds, a method of increasing the molecular weight can be cited. Considering the influence on the carrier transport property of organic compounds, etc., it is possible to introduce a substituent such as an aryl group or a heteroaryl group to increase the molecular weight, but in this case, other problems such as the reduction of the S1 energy level and the T1 energy level occur.
[0011] Therefore, an object of one embodiment of the present invention is to provide an organic compound with high heat resistance. Another object of one embodiment of the present invention is to provide a T value which is one of the indicators of heat resistance of an organic compound. g An organic compound having high S1 level and T1 level. An organic compound having high carrier transport property is provided.
[0012] Another object of one embodiment of the present invention is to provide a light-emitting device having good characteristics. Another object of one embodiment of the present invention is to improve the reliability of the light-emitting device. Another object of one embodiment of the present invention is to improve the luminous efficiency of the light-emitting device.
[0013] Another object of one embodiment of the present invention is to provide a light emitting device with low power consumption. Another object of one embodiment of the present invention is to provide a display device with low power consumption. Another object of one embodiment of the present invention is to provide a lighting device with low power consumption.
[0014] Another object of one embodiment of the present invention is to provide a novel organic compound, a novel light-emitting device, a novel light-emitting apparatus, a novel display apparatus, or a novel lighting apparatus.
[0015] Note that the recording of these purposes does not prevent the existence of other purposes. One mode of the present invention does not need to achieve all of the above purposes. Purposes other than the above purposes can be clearly seen from the description of the specification, drawings, claims, etc., and can be extracted from these descriptions.
[0016] One embodiment of the present invention is an organic compound represented by the following general formula (G1).
[0017] [Chemical formula 1]
[0018] In the general formula (G1), Q represents carbon or silicon, R 1 and R 2 Each independently represents an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 8 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, n represents an integer of 1 to 3, α 1 To α 4 Each independently represents a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group, R 15 , R 25 , R 31 , R 45 , R 55 and R 61 At least one of R represents a single bond, and the other R 15 , R 25 , R 31 , R 45 , R 55 and R 61 Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, R 11 To R 14 , R21 To R 24 , R 32 To R 35 , R 41 To R 44 , R 51 To R 54 and R 62 To R 65 Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 8 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms. 15 When it is a single bond, R 15 With α 2 Bond to form a ring. 45 When it is a single bond, R 45 With α 4 In addition, in R 25 and R 31 When both are single bonds, R 25 and R 31 Bonded to each other to form a ring. 55 and R 61 When both are single bonds, R 55 and R 61 bonded to each other to form a ring. 25 and R 31 When one of is a single bond and the other is hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, α 2 is a substituted or unsubstituted biphenylene group, R 25 and R 31 One of the 2 Bond to form a ring. 55 and R 61 When one of is a single bond and the other is hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, α 4 is a substituted or unsubstituted biphenylene group, R 55 and R 61 One of the 4 bonded to form a ring.
[0019] In addition, one embodiment of the present invention is an α of the above structure 1 and α 3 Each of the following is independently an organic compound which is substituted or unsubstituted m-phenylene.
[0020] Another embodiment of the present invention is an organic compound represented by any one of the following general formulae (G2-1), (G1-2-2), and (G2-3).
[0021] [Chemical formula 2]
[0022] In the general formulas (G2-1), (G1-2-2) and (G2-3), Q represents carbon or silicon, and R 1 and R 2 Each independently represents an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 8 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, n represents an integer of 1 to 3, α 1 To α 4 Each independently represents a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group, R 11 To R 15 , R 21 To R 25 , R 31 To R 35 , R 41 To R 45 , R 51 To R 55 , R 61 To R 65 , R 71 To R 74 , R 81 To R 84 , R 91 To R 96 and R 101 To R 106 Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
[0023] In addition, one embodiment of the present invention is a T in the above structure g It is an organic compound above 100°C.
[0024] Another embodiment of the present invention is an organic compound represented by any one of the following structural formulas (100), (101), (102) and (114).
[0025] [Chemical formula 3]
[0026] In addition, one embodiment of the present invention is a light-emitting device comprising a first electrode, a second electrode and an organic compound layer (EL layer), wherein the organic compound layer is located between the first electrode and the second electrode, and the organic compound layer contains the organic compound of one embodiment of the present invention described above (an organic compound represented by the general formula (G1)).
[0027] In addition, one embodiment of the present invention is a light-emitting device, comprising a first electrode, a second electrode and an organic compound layer (EL layer), wherein the organic compound layer is located between the first electrode and the second electrode, the organic compound layer is composed of multiple layers containing organic compounds and includes more than one light-emitting layer, and any one of the multiple layers containing the organic compound, from the layer in contact with the first electrode to at least the light-emitting layer, contains the organic compound of one embodiment of the present invention described above (an organic compound represented by the general formula (G1)).
[0028] In addition, one embodiment of the present invention is a light-emitting device, comprising a first electrode, a second electrode and an organic compound layer (EL layer), wherein the organic compound layer is located between the first electrode and the second electrode, the organic compound layer is composed of multiple layers containing organic compounds and includes more than one light-emitting layer, the light-emitting layer contains the organic compound of one embodiment of the present invention mentioned above (an organic compound represented by the general formula (G1)) and a second organic compound, and the second organic compound has a π-electron-deficient heteroaromatic ring.
[0029] In addition, another embodiment of the present invention is a light-emitting device, wherein an organic compound layer (EL layer) formed between a pair of electrodes has a stacked structure composed of a plurality of layers including a light-emitting layer, the ends of the organic compound layer are consistent or approximately consistent, the organic compound layer has a first partial structure, a second partial structure, and a third partial structure, the first partial structure and the second partial structure are connected by the third partial structure, at least one of the first partial structure and the second partial structure has any one or more of a π-electron-rich heteroaromatic ring, an aromatic amine skeleton, and a π-electron-deficient heteroaromatic ring, and the third partial structure includes a first organic compound represented by the following general formula (L1). Note that the first organic compound includes the organic compound of one embodiment of the present invention described above (the organic compound represented by the general formula (G1)).
[0030] [Chemical formula 4]
[0031] In the general formula (L1), Q represents carbon or silicon, R 1 and R 2 Each independently represents an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 8 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and n represents an integer of 1 to 3.
[0032] In addition, one embodiment of the present invention is a light-emitting device having the above-described structures, wherein the first organic compound is contained in the light-emitting layer or a layer in contact with the light-emitting layer.
[0033] In addition, one embodiment of the present invention is a light-emitting device having the above-mentioned structures, wherein either the first partial structure or the second partial structure is represented by the following general formula (T1).
[0034] [Chemical formula 5]
[0035] In the general formula (T1), α 1 and α 2 Each independently represents a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, Ar 1 To Ar 3 Each independently represents a substituted or unsubstituted aryl group having 6 to 12 carbon atoms. 1 With α 2 They may be bonded to each other to form a ring or may not form a ring. 2 with Ar 2 They may be bonded to each other to form a ring or may not form a ring. 2 with Ar 3 They may or may not be bonded to each other to form a ring.
[0036] In addition, one embodiment of the present invention is a light-emitting device having the above-mentioned structures, wherein T of the first organic compound is g It is above 100°C.
[0037] In addition, one embodiment of the present invention is a light-emitting device including the light-emitting device of each structure described above and a transistor or a substrate.
[0038] In addition, one embodiment of the present invention is an electronic device including the light emitting device having the above structure, a detection unit, an input unit, or a communication unit.
[0039] In addition, one embodiment of the present invention is a lighting device including the light emitting device having the above structure and a housing.
[0040] According to one embodiment of the present invention, there is provided an organic compound with high heat resistance. g In addition, according to one embodiment of the present invention, an organic compound with high S1 energy level and T1 energy level can be provided. In addition, according to one embodiment of the present invention, an organic compound with carrier transport properties can be provided. In addition, an organic compound that can be used for a light-emitting layer and a layer in contact with the light-emitting layer in a light-emitting device exhibiting blue fluorescence or phosphorescence can be provided.
[0041] In addition, according to one embodiment of the present invention, a light-emitting device having good characteristics can be provided. In addition, according to one embodiment of the present invention, the reliability of the light-emitting device can be improved. In addition, according to one embodiment of the present invention, the luminous efficiency of the light-emitting device can be improved. In addition, a light-emitting device having heat resistance capable of withstanding heating during the manufacturing process, storage, or driving can be provided.
[0042] According to one embodiment of the present invention, a light emitting device with low power consumption can be provided. According to one embodiment of the present invention, a display device with low power consumption can be provided. According to one embodiment of the present invention, a lighting device with low power consumption can be provided.
[0043] In addition, according to one embodiment of the present invention, a novel organic compound, a novel light-emitting device, a novel light-emitting apparatus, a novel display apparatus, or a novel lighting apparatus can be provided.
[0044] Note that the description of these effects does not prevent the existence of other effects. One embodiment of the present invention does not necessarily have all of the above effects. Effects other than the above effects can be extracted from the description of the specification, drawings, and claims. BRIEF DESCRIPTION OF THE DRAWINGS
[0045] Figures 1A to 1F is a diagram illustrating a structure of a light emitting device according to an embodiment; Figure 2 is a diagram illustrating a structure of a light emitting device according to an embodiment; FIG. 3A to FIG. 3D is a diagram illustrating a light emitting device according to an embodiment; FIG. 4A to FIG. 4C is a diagram illustrating a method for manufacturing a light emitting device according to an embodiment; FIG. 5A to FIG. 5C is a diagram illustrating a method for manufacturing a light emitting device according to an embodiment; FIG. 6A to FIG. 6D is a diagram illustrating a method for manufacturing a light emitting device according to an embodiment; 7A to 7C is a diagram illustrating a light emitting device according to an embodiment; FIG. 8A to FIG. 8F is a diagram illustrating a device and a pixel arrangement according to an embodiment; 9A to 9C is a diagram illustrating a pixel circuit and a transistor according to an embodiment; Fig.10 is a diagram illustrating a light emitting device according to an embodiment; FIG. 11A to FIG. 11E is a diagram illustrating an electronic device according to an embodiment; FIG. 12A to FIG. 12E is a diagram illustrating an electronic device according to an embodiment; Fig.13A and Fig. 13B is a diagram illustrating an electronic device according to an embodiment; Fig.14A and Fig. 14B is a diagram illustrating a lighting device according to an embodiment; Fig.15 is a diagram illustrating a lighting device according to an embodiment; Fig.16 It's PSiYGA2 1 H NMR spectrum; Fig.17 is the MS spectrum of PSiYGA2; Fig.18 It's YGABmP 1 H NMR spectrum; Fig.19 is the MS spectrum of YGABmP; Fig. 20 is the emission spectra of PSiYGA2, YGABmP, YGA1BP and YGABP in toluene solution; Fig.21 It is PCCz2PSi 1 H NMR spectrum; Fig. 22 is the emission spectrum of PCCz2PSi and PCCP in toluene solution; Fig.23 It's mCzCz2PSi 1 H NMR spectrum; Fig.24 is the MS spectrum of mCzCz2PSi; Fig.25 are the absorption and emission spectra of mCzCz2PSi in toluene solution; Fig.26 are the absorption and emission spectra of the thin film of mCzCz2PSi; Fig. 27 is the emission spectrum of mCzCz2PSi and PSiCzCz in toluene solution; Fig.28 is the phosphorescence spectrum of the thin films of mCzCz2PSi and PSiCzCz; Fig.29 is a diagram showing the brightness-current density characteristics of the light emitting device 1 and the comparative light emitting device 2; Fig.30 Current efficiency-luminance characteristics of the light emitting device 1 and the comparative light emitting device 2 are shown. Fig.31 is a diagram showing power efficiency-luminance characteristics of the light emitting device 1 and the comparative light emitting device 2; Fig.32 The external quantum efficiency-brightness characteristics of the light emitting device 1 and the comparative light emitting device 2 are shown; Fig.33 1 and 2 are electroemission spectra of the light emitting device 1 and the comparative light emitting device 2. Fig.34 is a diagram showing the brightness-current density characteristics of the light emitting device 3 and the comparative light emitting device 4; Fig.35 is a diagram showing current efficiency-luminance characteristics of the light emitting device 3 and the comparative light emitting device 4; Fig.36 are the electroemission spectra of the light emitting device 3 and the comparative light emitting device 4; Fig.37 is a diagram showing the brightness-current density characteristics of the light emitting device 5 and the comparative light emitting device 6; Fig.38 is a diagram showing current efficiency-luminance characteristics of the light emitting device 5 and the comparative light emitting device 6; Fig.39 is a diagram showing external quantum efficiency-luminance characteristics of the light emitting device 5 and the comparative light emitting device 6; Fig.40 are the electroemission spectra of the light emitting device 5 and the comparative light emitting device 6; Fig.41 is a diagram showing the brightness-current density characteristics of the light emitting device 7 and the comparative light emitting device 8; Fig.42 The current efficiency-brightness characteristics of the light emitting device 7 and the comparative light emitting device 8 are shown; Fig.43 The external quantum efficiency-brightness characteristics of the light emitting device 7 and the comparative light emitting device 8 are shown; Fig.44 are the electroemission spectra of the light emitting device 7 and the comparative light emitting device 8; Fig.45 is a diagram showing changes in brightness of the light emitting device 7 and the comparative light emitting device 8 with respect to driving time; Fig.46 is a graph showing the brightness-current density characteristics of the light emitting device 9 and the comparative light emitting device 10; Fig.47 is a diagram showing current efficiency-luminance characteristics of the light emitting device 9 and the comparative light emitting device 10; Fig.48 is a diagram showing power efficiency-luminance characteristics of the light emitting device 9 and the comparative light emitting device 10; Fig.49 are electroemission spectra of light emitting device 9 and comparative light emitting device 10; Fig.50is a diagram showing the brightness-current density characteristics of the light emitting device 11 and the comparative light emitting device 12; Fig.51 is a diagram showing current efficiency-luminance characteristics of the light emitting device 11 and the comparative light emitting device 12; Fig.52 is a diagram showing the brightness-voltage characteristics of the light emitting device 11 and the comparative light emitting device 12; Fig.53 is a graph showing current density-voltage characteristics of the light emitting device 11 and the comparative light emitting device 12; Fig.54 is a diagram showing power efficiency-luminance characteristics of the light emitting device 11 and the comparative light emitting device 12; Fig.55 is a graph showing external quantum efficiency-luminance characteristics of the light emitting device 11 and the comparative light emitting device 12; Fig.56 1 is a diagram showing energy efficiency-luminance characteristics of the light emitting device 11 and the comparative light emitting device 12; Fig.57 are the electroemission spectra of the light emitting device 11 and the comparative light emitting device 12; Fig.58 The bond energy of the Q-R1 bond of each organic compound is shown. DETAILED DESCRIPTION
[0046] Hereinafter, the embodiments of the present invention will be described in detail with reference to the accompanying drawings. Note that the present invention is not limited to the contents described below, and its mode and details can be transformed into various forms without departing from the purpose and scope of the present invention. Therefore, the present invention should not be interpreted as being limited to the contents described in the embodiments shown below.
[0047] In addition, for ease of understanding, the position, size, range, etc. of each structure shown in the drawings and the like may not show its actual position, size, range, etc. Therefore, the disclosed invention is not necessarily limited to the position, size, range, etc. disclosed in the drawings and the like.
[0048] In addition, in this specification, for the sake of convenience, ordinal numbers such as first and second are added, but they sometimes do not indicate the order of processes or the order of stacking. Therefore, for example, "first" can be appropriately replaced with "second" or "third" for description. In addition, the ordinal numbers recorded in this specification and the like are sometimes inconsistent with the ordinal numbers used to specify one embodiment of the present invention.
[0049] In this specification and the like, when describing the configuration of the invention using drawings, the same reference numerals may be used in common in different drawings to indicate the same parts.
[0050] In this specification, "film" and "layer" may be interchanged. For example, "conductive layer" may be interchanged with "conductive film". Or, "insulating film" may be interchanged with "insulating layer".
[0051] In addition, in the present specification and the like, when a group is referred to as "substituted or unsubstituted", "substituted" means that the group has a substituent.
[0052] Note that in this specification, etc., hydrogen includes protium and deuterium. Therefore, unless otherwise specified, the case where "hydrogen" is simply described in a general formula or sentence, or the case where hydrogen is omitted in a chemical formula, also includes the case where the hydrogen is deuterium.
[0053] In this specification, the singlet excited state (S * ) refers to a singlet state with excitation energy. In addition, the S1 energy level is the lowest energy level of the singlet excitation energy level, which refers to the excitation energy level of the lowest singlet excitation state. In addition, the triplet excitation state (T * ) refers to a triplet state having excitation energy. In addition, the T1 level is the lowest energy level of the triplet excitation energy level, which refers to the excitation energy level of the lowest triplet excitation state.
[0054] In addition, in this specification, etc., fluorescent materials and fluorescent compounds refer to materials and compounds that emit light when returning from a singlet excited state to a ground state. On the other hand, phosphorescent materials and phosphorescent compounds refer to materials and compounds that emit light in the visible light region at room temperature when returning from a triplet excited state to a ground state. In other words, phosphorescent materials and phosphorescent compounds refer to one of materials and compounds that can convert triplet excitation energy into visible light.
[0055] Note that in this specification and the like, room temperature refers to any temperature from 0°C to 40°C.
[0056] Regarding the S1 energy level or T1 energy level of an organic compound, when the ν=0→ν=0 transition (0→0 band) between the vibrational energy levels of the ground state and the excited state is clearly observed in the fluorescence spectrum or the phosphorescence spectrum, it is preferably calculated using the 0→0 band (for example, refer to non-patent document 1). In addition, when the 0→0 band is unclear, a tangent line is drawn at the value of the maximum inclination on the short wavelength side of the peak in the fluorescence spectrum, and the wavelength energy of the intersection of the tangent line and the horizontal axis (wavelength) or the baseline is the S1 energy level, and a tangent line is drawn at the value of the maximum inclination on the short wavelength side of the peak in the phosphorescence spectrum, and the energy of the intersection of the tangent line and the horizontal axis (wavelength) or the baseline is the T1 energy level (for example, refer to non-patent document 2). In addition, when comparing energy levels, comparison is made between energy levels calculated using the same method.
[0057] In addition, in this specification, etc., the blue wavelength region refers to a wavelength region of more than 400nm and less than 490nm, and blue luminescence is luminescence having at least one emission spectrum peak in this region. In addition, the green wavelength region refers to a wavelength region of more than 490nm and less than 580nm, and green luminescence is luminescence having at least one emission spectrum peak in this region. In addition, the red wavelength region refers to a wavelength region of more than 580nm and less than 680nm, and red luminescence is luminescence having at least one emission spectrum peak in this region. In addition, the near-infrared wavelength region refers to a wavelength region of more than 700nm and less than 2500nm, and near-infrared luminescence is luminescence having at least one emission spectrum peak in this region.
[0058] In this specification, when describing an aromatic ring (including a heteroaromatic ring) A, unless otherwise noted, the description may be applied to a fused aromatic ring formed by fusing the aromatic ring A with another aromatic ring or heteroaromatic ring. For example, when describing an organic compound having a carbazole ring, unless otherwise noted, the description may be applied to an organic compound having a fused aromatic ring such as a benzocarbazole ring or a dibenzocarbazole ring formed by fusing a carbazole ring with a benzene ring.
[0059] The values of the HOMO level and the LUMO level used in this specification can be calculated by electrochemical measurement. Typical examples of electrochemical measurement include cyclic voltammetry (CV) measurement and differential pulse voltammetry (DPV) measurement.
[0060] In addition, T used in this specification can be obtained by differential scanning calorimetry (DSC). g When T g In the present specification, when the heating rate is set at about 40°C / min to 50°C / min, T g The measured value of the endothermic rise (onset) temperature is regarded as the read value.
[0061] Implementation Method 1 In this embodiment, an organic compound which is one embodiment of the present invention is described.
[0062] An organic compound of one embodiment of the present invention is an organic compound represented by the general formula (G1). Note that in the following general formula (G1), for the sake of explanation, a frame line representing the first partial structure (P1), a frame line representing the second partial structure (P2), and a frame line representing the third partial structure (L1) are added. The organic compound represented by the general formula (G1) has a structure in which the first partial structure (P1) and the second partial structure (P2) are connected via the third partial structure (L1). The main chain of the third partial structure (L1) connecting the first partial structure (P1) and the second partial structure (P2) is sp 3 Hybrid orbitals (σ bonds) are formed. By adopting this structure, the S1 energy level and T1 energy level of organic compounds can be increased.
[0063] [Chemical formula 6]
[0064] Note that in the general formula (G1), Q represents carbon or silicon, and R 1 and R 2 Each independently represents an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 8 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, n represents an integer of 1 to 3, α 1 To α 4 Each independently represents a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group, R 15 , R 25 , R 31 , R 45 , R 55 and R 61 At least one of R represents a single bond, and the other R 15 , R 25 , R 31 , R 45 , R 55 and R 61 Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, R 11 To R 14 , R 21 To R 24 , R 32 To R 35 , R 41 To R 44 , R 51 To R 54 and R 62 To R 65 Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 8 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.15 When it is a single bond, R 15 With α 2 Bond to form a ring. 45 When it is a single bond, R 45 With α 4 In addition, in R 25 and R 31 When both are single bonds, R 25 and R 31 Bonded to each other to form a ring. 55 and R 61 When both are single bonds, R 55 and R 61 bonded to each other to form a ring. 25 and R 31 When one of is a single bond and the other is hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, α 2 is a substituted or unsubstituted biphenylene group, R 25 and R 31 One of the 2 Bond to form a ring. 55 and R 61 When one of is a single bond and the other is hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, α 4 is a substituted or unsubstituted biphenylene group, R 55 and R 61 One of the 4 bonded to form a ring.
[0065] Note that even the simple introduction of a chain-like substituent into an organic compound can increase the T g . Note that the effect of chain substituents on improving heat resistance is not as high as that of aromatic groups such as aryl groups and heteroaryl groups. In addition, when multiple chain substituents are introduced into an organic compound, the carrier transport property of the organic compound may be damaged. In this regard, in an organic compound of one embodiment of the present invention, since the first partial structure (P1) having an aromatic amine skeleton with good hole transport properties and the second partial structure (P2) are linked by the third partial structure (L1) having a main chain formed by a σ bond, T can be achieved. g An organic compound with high S1 energy level and T1 energy level and good hole transport property.
[0066] Note that in the general formula (G1), R 15 When it is a single bond, as shown in the following general formula (G1-1-1), R 15 Can be used with α 2 Furthermore, in R 45When it is a single bond, as shown in the following general formula (G1-1-2), R 45 Can be used with α 4 By forming a ring in this way, an organic compound having a higher S1 level and T1 level than when no ring is formed can be provided.
[0067] [Chemical formula 7]
[0068] In the general formula (G1), R 25 and R 31 When all are single bonds, as shown in the following general formula (G1-2-1), R 25 and R 31 can be bonded to each other to form a ring. 55 and R 61 When all are single bonds, as shown in the following general formula (G1-2-2), R 55 and R 61 They can be bonded to each other to form a ring. By forming a ring in this way, an organic compound with high S1 energy level and T1 energy level can be provided compared with a case where no ring is formed. In addition, by forming a ring, a molecular structure having a carbazole skeleton is formed. Since the carbazole skeleton has good hole transport properties, an organic compound with high hole transport properties can be provided.
[0069] [Chemical formula 8]
[0070] In the general formula (G1), R 25 and R 31 When one of is a single bond and the other is hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, α 2 is a substituted or unsubstituted biphenylene group, R 25 and R 31 One of the 2 The following general formula (G1-3-1) shows R 25 is a single bond. Furthermore, in R 55 and R 61 When one of is a single bond and the other is hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, α 4 is a substituted or unsubstituted biphenylene group, R 55 and R 61 One of the 4 The following general formula (G1-3-2) shows that R 55is the chemical formula when it is a single bond. By adopting this structure, a T g Furthermore, by forming a ring, an organic compound having a higher S1 level and T1 level than when no ring is formed can be provided.
[0071] [Chemical formula 9]
[0072] In the general formulas (G1-3-1) and (G1-3-2), R 91 To R 96 and R 101 To R 106 Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
[0073] In addition, in the general formula (G1), in α 1 and α 3 When each of the two independently is a substituted or unsubstituted meta-phenylene, the sublimation temperature is low due to the bulky molecular structure of the organic compound, and thus an organic compound that is less likely to be thermally decomposed during sublimation can be provided.
[0074] Furthermore, one embodiment of the present invention is an organic compound represented by the following general formulae (G2-1), (G2-2), and (G2-3).
[0075] [Chemical formula 10]
[0076] In the following general formulas (G2-1), (G2-2) and (G2-3), Q represents carbon or silicon, and R 1 and R 2 Each independently represents an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 8 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, n represents an integer of 1 to 3, α 1 To α 4 Each independently represents a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group, R 11 To R 15 , R 21 To R 25 , R 31 To R 35 , R 41 To R 45 , R 51 To R 55 , R 61 To R 65 , R 71 To R 74, R 81 To R 84 , R 91 To R 96 and R 101 To R 106 Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
[0077] The general formula (G2-1) has the following structure: R in the general formula (G1) 15 , R 45 , R 25 , R 31 , R 55 and R 61 is a single bond, α 2 and α 4 is a substituted or unsubstituted phenylene group, R 15 With α 2 Bonded to form a ring, R 45 With α 4 Bonded to form a ring, R 25 and R 31 Bonded to each other to form a ring, R 55 and R 61 The carbazole rings are bonded to each other to form a ring. By forming a ring in this way, an organic compound having a high S1 energy level and a high T1 energy level can be provided compared to a case where no ring is formed. In addition, since the carbazole ring has a good hole transport property, an organic compound with a high hole transport property can be realized.
[0078] In addition to the above structure, the general formula (G2-1) has α 1 and α 3 The structure of each of the substituted or unsubstituted meta-phenylene groups is independent of each other. By adopting such a structure, since the organic compound can be made bulky, the interaction between molecules can be reduced. Therefore, the sublimation temperature is relatively low, and an organic compound that is not prone to thermal decomposition during sublimation can be provided.
[0079] The general formula (G2-2) has the following structure: R in the general formula (G1) 25 and R 31 are all single bonds, they are bonded to each other to form a ring, and R 55 With R 61 All are single bonds, and they are bonded to each other to form a ring. By forming a ring in this way, an organic compound with high S1 energy level and T1 energy level can be provided compared with the case where no ring is formed. In addition, since it has a carbazole ring with good hole transport properties, an organic compound with high hole transport properties can be provided.
[0080] The general formula (G2-3) has the following structure: R in the general formula (G1) 31is a single bond, α 2 is a substituted or unsubstituted phenylene group, R 31 With α 2 Bonded to form a ring, R 61 is a single bond, α 4 is a substituted or unsubstituted phenylene group, R 61 With α 4 By adopting this structure, the molecular weight increases, so T g In addition, by forming a ring, an organic compound having a high S1 energy level and a high T1 energy level can be provided compared to the case where no ring is formed. In addition, since two carbazole rings having good hole transport properties are bonded to each other at the 3-position, an organic compound having a higher hole transport property can be provided.
[0081] Furthermore, one embodiment of the present invention is an organic compound represented by the following general formula (G3-1) and (G3-2).
[0082] [Chemical formula 11]
[0083] In the following general formulas (G3-1) and (G3-2), Q represents carbon or silicon, and R 1 and R 2 Each independently represents an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 8 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, n represents an integer of 1 to 3, α 1 To α 4 Each independently represents a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group, R 11 To R 15 , R 21 To R 25 , R 31 To R 35 , R 41 To R 45 , R 51 To R 55 , R 61 To R 65 , R 71 To R 74 , R 81 To R 84 , R 91 To R 96 and R 101 To R 106 Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
[0084] The general formula (G3-1) has α in the general formula (G2-2) 1 and α 3 The general formula (G3-2) has the structure of α in the general formula (G2-3). 1 and α 3 It is a substituted or unsubstituted p-phenylene structure.
[0085] Note that in each of the above general formulas, when Q is silicon, since the radius of the silicon atom is larger than that of the carbon atom, the steric hindrance of the substituent bonded to Q can be suppressed compared to when Q is carbon. As a result, the stability to the excitation of the organic compound can be improved. By using such an organic compound in a light-emitting device, a light-emitting device characteristic with a long life can be expected.
[0086] In the above general formulas, when Q is silicon, carrier transport properties can be improved. By using such an organic compound in a light-emitting device, a reduction in driving voltage can be expected.
[0087] In the above general formulas, when Q is carbon, R 1 and R 2 Compared with bulky substituents, the group bonded to Q (i.e., R 1 , R 2 Therefore, when Q is carbon, it is more preferred that, for example, R 1 and R 2 Each independently is a chain group such as an alkyl group having 1 to 6 carbon atoms or a cyclic group such as a cycloalkyl group.
[0088] In addition, in the above general formulas, when increasing R 1 and R 2 When the total molecular weight of the organic compound is too large, the total molecular weight of the organic compound increases. However, when the total molecular weight of the organic compound is too large, the sublimation temperature (or evaporation temperature) is too high, so it may become a material that is easily thermally decomposed during vapor deposition. 1 and R 2 When R is an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 8 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, the sublimation temperature (or evaporation temperature) of the organic compound can be suppressed from being too high. 1 and R 2 When each is independently a methyl group or a phenyl group, these stabilities are improved.
[0089] As described above, by increasing the molecular weight of the organic compound of one embodiment of the present invention, T gOn the other hand, when the molecular weight of the organic compound of one embodiment of the present invention is too large, the sublimation temperature (or evaporation temperature) may be too high, and the material may be easily thermally decomposed during vapor deposition. Therefore, the molecular weight of the organic compound of one embodiment of the present invention is preferably 600 or more and 1500 or less, and more preferably 700 or more and 1300 or less. Therefore, T g , and can provide an organic compound that is not easily thermally decomposed.
[0090] In the above general formulas, when n is 2 or 3, multiple Qs may be the same or different, and multiple R 1 Can be the same or different, multiple R 2 They may be the same or different.
[0091] Next, alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 6 to 8 carbon atoms, and aryl groups having 6 to 12 carbon atoms, which can be used as substituents in the above general formulae, are described and specific examples are given. Note that substituents that can be used in the above general formulae are not limited to the specific examples given below.
[0092] <<Alkyl group having 1 to 6 carbon atoms>> In the present specification, an alkyl group having 1 to 6 carbon atoms refers to a linear or branched alkane having 1 to 6 carbon atoms (C n H 2n+2 (n=1 to 6)) is a monovalent group in which one hydrogen atom is removed. Specific examples of the alkyl group having 1 to 6 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, neohexyl, 3-methylpentyl, and 2-methylpentyl.
[0093] <<Cycloalkyl group having 6 to 8 carbon atoms>> In the present specification, a cycloalkyl group having 6 to 8 carbon atoms refers to a cycloalkane (C n H 2n (n=6 to 8)) is a monovalent group obtained by removing one hydrogen atom from one of the ring-forming carbon atoms. Specific examples of the cycloalkyl group having 6 to 8 carbon atoms include cyclohexyl, cyclooctyl, cycloheptyl, etc. When the cycloalkyl group having 6 to 8 carbon atoms has a substituent, specific examples of the substituent include an alkyl group having 1 to 6 carbon atoms.
[0094] <<Aryl group having 6 to 12 carbon atoms>> In this specification, etc., an aryl group having 6 to 12 carbon atoms refers to a monovalent group obtained by removing a hydrogen atom from one of the ring-forming carbon atoms of a monocyclic or polycyclic aromatic compound having 6 to 12 carbon atoms forming a ring. Note that in this specification, etc., a polycyclic aromatic compound refers to an aromatic compound having two or more cyclic structures in a molecule, including both a structure in which multiple rings are bonded by a single bond, such as biphenyl, and a structure in which multiple rings are condensed, such as naphthalene. Specific examples of aryl groups having 6 to 12 carbon atoms include phenyl, naphthyl, fluorenyl, biphenyl, etc. When a cyclic aromatic group having 6 to 12 carbon atoms has a substituent, a specific example of the substituent is an alkyl group having 1 to 6 carbon atoms.
[0095] The above are examples of substituents that can be used in the above general formula.
[0096] Specific examples of the organic compound of one embodiment of the present invention represented by the above general formula include organic compounds represented by the following structural formulas (100) to (129).
[0097] [Chemical formula 12]
[0098] [Chemical formula 13]
[0099] [Chemical formula 14]
[0100] [Chemical formula 15]
[0101] The organic compounds represented by the above structural formulae (100) to (129) are examples of the organic compounds of one embodiment of the present invention, but one embodiment of the present invention is not limited thereto.
[0102] Note that when an alkyl group such as a tert-butyl group or a methyl group is introduced into an aromatic ring or a heteroaromatic ring contained in an organic compound of one embodiment of the present invention, since the organic compound becomes bulky, the sublimation temperature can be lowered, and an organic compound that is not easily thermally decomposed can be provided. As an example of introducing an alkyl group such as a tert-butyl group or a methyl group into an aromatic ring or a heteroaromatic ring, structural formulas (104), (105), (107), (109) to (111), (118), (119), (123), (124), and (125) can be cited.
[0103] In addition, as in structural formulas (109) to (111), (114) to (128), and (130) to (135), the molecular weight can be adjusted by bonding an alkyl group such as a tert-butyl group or a methyl group to carbon or silicon having the third partial structure (L1), thereby adjusting the sublimation temperature.
[0104] Next, as an example of an organic compound of one embodiment of the present invention, a method for synthesizing an organic compound represented by general formula (G1) is described. Note that various reactions can be used as a method for synthesizing general formula (G1) and it is not limited to the following synthesis method.
[0105] [Chemical formula 16]
[0106] In the general formula (G1), Q represents carbon or silicon, R 1 and R 2 Each independently represents an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 8 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, n represents an integer of 1 to 3, α 1 To α 4 Each independently represents a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group, R 15 , R 25 , R 31 , R 45 , R 55 and R 61 At least one of R represents a single bond, and the other R 15 , R 25 , R 31 , R 45 , R 55 and R 61 Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, R 11 To R 14 , R 21 To R 24 , R 32 To R 35 , R 41 To R 44 , R 51 To R 54 and R 62 To R 65 Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 8 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms. 15 When it is a single bond, R 15 With α 2 Bond to form a ring.45 When it is a single bond, R 45 With α 4 In addition, in R 25 and R 31 When both are single bonds, R 25 and R 31 Bonded to each other to form a ring. 55 and R 61 When both are single bonds, R 55 and R 61 bonded to each other to form a ring. 25 and R 31 When one of is a single bond and the other is hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, α 2 is a substituted or unsubstituted biphenylene group, R 25 and R 31 One of the 2 Bond to form a ring. 55 and R 61 When one of is a single bond and the other is hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, α 4 is a substituted or unsubstituted biphenylene group, R 55 and R 61 One of the 4 bonded to form a ring.
[0107] By subjecting the halogen compound (a1) to a cross-coupling reaction with the amine compound (a2) and the amine compound (a3), an organic compound represented by the general formula (G1) can be obtained. The following is a synthesis scheme (A-1).
[0108] [Chemical formula 17]
[0109] In the synthesis scheme (A-1), Q, R 1 , R 2 , α 1 To α 4 , R 15 , R 25 , R 31 , R 45 , R 55 , R 61 , R 11 To R 14 , R 21 To R 24 , R 32 To R 35 , R 41 To R 45 , R51 To R 55 , R 61 To R 65 The same as the above atoms or groups. 1 and X 2 Represents halogen.
[0110] In the synthesis scheme (A-1), specific examples of halogen include chlorine, bromine, iodine, etc. Due to high reactivity, X 1 and X 2 Preferably bromine or iodine, more preferably iodine. The reaction can be carried out under various conditions. For example, a synthesis method using a metal catalyst in the presence of a base can be used. Specifically, Ullmann coupling or Buchwald-Hartwig reaction can be used.
[0111] Note that when the amine compound (a2) and the amine compound (a3) have different molecular structures, it is preferred to react the halogen compound (a1) with the amine compound (a2) and the amine compound (a3) in sequence because the synthesis can be performed with high purity and high yield. On the other hand, when the amine compound (a2) and the amine compound (a3) have the same molecular structure, it is preferred to react the halogen compound (a1) with 2 equivalents of the amine compound (a2) because the number of steps can be reduced and the synthesis cost can be suppressed.
[0112] The structure described in this embodiment can be used in combination with the structure described in other embodiment modes as appropriate.
[0113] Implementation Method 2 In this embodiment, refer to Figures 1A to 1F and Figure 2 The structure of a light-emitting device according to one embodiment of the present invention will be described.
[0114] The light-emitting device of one embodiment of the present invention can use the organic compound described below (referred to as a first organic compound). Note that the first organic compound includes the organic compound represented by the general formula (G1) described in Embodiment 1.
[0115] The first organic compound has a first partial structure, a second partial structure, and a third partial structure. The first partial structure and the second partial structure are connected through the third partial structure. At least one of the first partial structure and the second partial structure includes a skeleton with carrier transport properties (hole transport properties or electron transport properties or both). The third partial structure is an organic compound represented by the general formula (L1).
[0116] [Chemical formula 18]
[0117] In the general formula (L1), Q represents carbon or silicon, R 1 and R 2 Each independently represents an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 8 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; and n represents 1 to 3.
[0118] As the skeleton with hole transport properties, π-electron-rich heteroaromatic rings and aromatic amine skeletons can be cited, and as the skeleton with electron transport properties, π-electron-deficient heteroaromatic rings can be cited. That is, at least one of the first partial structure and the second partial structure preferably has one or more of the π-electron-rich heteroaromatic ring, the aromatic amine skeleton, and the π-electron-deficient heteroaromatic ring. Therefore, the first organic compound can be used as a carrier transport material.
[0119] As the π-electron-rich heteroaromatic ring, for example, a fused aromatic ring containing at least one of a pyrrole ring, a furan ring, and a thiophene ring is preferred. More specifically, a fused aromatic ring having a carbazole ring, a dibenzofuran ring, or a dibenzothiophene ring, or these rings are further fused with an aromatic ring or a heteroaromatic ring, is preferred because of its chemical stability. In particular, a carbazole group substituted at the 9-position can increase the S1 energy level and the T1 energy level, so it is preferred.
[0120] As the aromatic amine skeleton, a tertiary amine without an NH bond is preferred, and in particular, the triarylamine skeleton preferably has excellent chemical stability and high hole transport properties in an excited state. As the aryl group of the triarylamine skeleton, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring is preferred, for example, phenyl, naphthyl, fluorenyl, etc. can be cited. In particular, phenyl can improve the S1 energy level and T1 energy level, so it is preferred.
[0121] At least one of the first partial structure and the second partial structure is more preferably a structure having both a π-electron-rich heteroaromatic ring and an aromatic amine skeleton. By adopting this structure, an organic compound having excellent hole transport properties and stable high reliability can be obtained.
[0122] Examples of π-electron-deficient heteroaromatic rings include oxadiazole rings, triazole rings, benzimidazole rings, quinoxaline rings, dibenzoquinoxaline rings, quinazoline rings, phenanthroline rings, pyridine rings, diazine rings (including pyrimidine rings, pyrazine rings, pyridazine rings), triazine rings, furanodiazine rings, etc. Among them, a skeleton containing a triazine ring or a diazine ring has excellent electron transport properties and is chemically stable in an excited state, so it is preferred.
[0123] Note that both the first partial structure and the second partial structure may use a skeleton having a carrier transport property, or one of the first partial structure and the second partial structure may not use a skeleton having a carrier transport property.
[0124] Note that the first organic compound may also be bipolar. That is, the first partial structure may have at least one of a π-electron-rich heteroaromatic ring and an aromatic amine skeleton, and the second partial structure may have a π-electron-deficient heteroaromatic ring.
[0125] When a skeleton having carrier transport properties is used in both the first and second partial structures, the carrier transport properties of the organic compound can be improved. In addition, the molecular weight is increased, so that T g In addition, when the first partial structure and the second partial structure are skeletons having the same structure and carrier transport properties, it is preferred because the organic compound can be easily synthesized.
[0126] When any of the first partial structure and the second partial structure does not use a skeleton having carrier transport properties, it is preferred that the partial structure be a structure that can increase the molecular weight of the first organic compound. For example, as a structure that increases the molecular weight of the first organic compound, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms can be cited, preferably a phenyl group. Thus, the heat resistance of the first organic compound can be improved.
[0127] In this way, by connecting the first partial structure and the second partial structure via the third partial structure represented by the general formula (L1) described in Embodiment 1, an organic compound having high heat resistance and high S1 level and T1 level can be provided.
[0128] In addition, by using the first organic compound having high S1 energy level and T1 energy level in the carrier transport layer of the light-emitting device, the characteristics of the light-emitting device can be improved.
[0129] As a specific structure of the skeleton having a carrier transport property preferably used for at least one of the first partial structure and the second partial structure, a partial structure represented by the general formula (T1) can be mentioned.
[0130] [Chemical formula 19]
[0131] In the general formula (T1), α 1 and α 2 Each independently represents a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, Ar 1 To Ar 3 Each independently represents a substituted or unsubstituted aryl group having 6 to 12 carbon atoms. 1 With α 2 They may be bonded to each other to form a ring or may not form a ring. 2 with Ar 2 They may be bonded to each other to form a ring or may not form a ring. 2 with Ar3 They may or may not be bonded to each other to form a ring.
[0132] The partial structure represented by the general formula (T1) has at least one of a π-electron-rich heteroaromatic ring and an aromatic amine skeleton. Therefore, by using the partial structure represented by the general formula (T1), the first organic compound can be a material having a hole transport property.
[0133] Note that when a skeleton having carrier transport properties is used for both the first partial structure and the second partial structure, the heat resistance of the first organic compound can be improved, and the carrier transport properties of the first organic compound can be further improved. Therefore, as a specific example of the first organic compound, an organic compound represented by the general formula (G0) can be cited.
[0134] [Chemical formula 20]
[0135] In the general formula (G0), Q represents carbon or silicon, R 1 and R 2 Each independently represents an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 8 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and n represents 1 to 3. 1 and α 4 Each independently represents a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, Ar 1 To Ar 6 Each independently represents a substituted or unsubstituted aryl group having 6 to 12 carbon atoms. 1 With α 2 , α 2 with Ar 2 ,Ar 2 with Ar 3 One or more of Ar may be bonded to each other to form a ring, or may not form a ring. 4 With α 4 , α 4 with Ar 5 ,Ar 5 with Ar 6 One or more of the may be bonded to each other to form a ring, or may not form a ring.
[0136] The organic compound represented by the general formula (G0) uses a skeleton having carrier transport properties for both the first partial structure and the second partial structure, which are bonded via the partial structure represented by the general formula (L1). Therefore, the heat resistance of the first organic compound can be improved, and the carrier transport properties of the first organic compound can be further improved.
[0137] Note that in the general formula (T1) and the general formula (G0), it is more preferable that α 1 and α 4 are independently substituted or unsubstituted phenylene or substituted or unsubstituted biphenylene. In the general formula (T1), more preferably, Ar 1 To Ar 6 Each of the above is independently a substituted or unsubstituted phenyl group. Thus, an organic compound having a low sublimation temperature and not easily thermally decomposed during sublimation can be provided.
[0138] In general formula (T1) and general formula (G0), more preferably, Ar 1 With α 2 , α 2 with Ar 2 ,Ar 2 with Ar 3 More preferably, Ar 4 With α 4 , α 4 with Ar 5 ,Ar 5 with Ar 6 One or more of the are bonded to each other to form a ring. Therefore, in the general formula (T1), since a π-electron-rich heteroaromatic ring such as a carbazole ring is formed, the hole transport property of the first organic compound can be improved, which is preferred.
[0139] Next, the arylene group having 6 to 12 carbon atoms that can be used in the general formula (T1) and the general formula (G0) is described and specific examples are given. The alkyl group having 1 to 6 carbon atoms, the substituted or unsubstituted cycloalkyl group having 6 to 8 carbon atoms, and the aryl group having 6 to 12 carbon atoms that can be used as the substituents in the general formula (T1) and the general formula (G0) are the same as those described in Embodiment 1. Note that the substituents that can be used in the above general formulas are not limited to the specific examples given below.
[0140] <<Aryl group having 6 to 12 carbon atoms>> In this specification, etc., an arylene group having 6 to 12 carbon atoms means a divalent group obtained by removing one hydrogen atom from one of the ring-forming carbon atoms of an aryl group having 6 to 12 carbon atoms. Specific examples of the arylene group having 6 to 12 carbon atoms include 1,4-phenylene, 1,3-phenylene, 4,4'-biphenylene, etc. When the arylene group having 6 to 12 carbon atoms has a substituent, a specific example of the substituent includes an alkyl group having 1 to 6 carbon atoms.
[0141] The first organic compound (including the organic compound represented by the general formula (G1) described in Embodiment 1) has a carrier transport property. Therefore, by using the first organic compound in any one or more of the layers (hole injection layer, hole transport layer, light-emitting layer, electron transport layer, and electron injection layer) of the light-emitting device described later, the characteristics of the light-emitting device can be improved.
[0142] When the first organic compound has a hole transport property, the hole transport in the EL layer 103 becomes smooth by using the first organic compound in any one or more of the hole injection layer, hole transport layer and light-emitting layer described later, thereby improving the light-emitting efficiency of the light-emitting device 100.
[0143] When the first organic compound has electron transport properties, electron transport in the EL layer becomes smooth by using the first organic compound in any one or more of the light-emitting layer, electron transport layer and electron injection layer described later, thereby improving the light-emitting efficiency of the light-emitting device.
[0144] Note that the first organic compound may be a bipolar substance (a substance having high electron-transport properties and hole-transport properties).
[0145] Furthermore, the first organic compound preferably has high heat resistance. When a problem such as crystallization of the EL layer occurs, by adopting such a structure, crystallization of the EL layer can be prevented, thereby improving the brightness and reliability of the light-emitting device.
[0146] The first organic compound can have both high heat resistance and high S1 energy level and T1 energy level, so it can be said to be an effective material when the light-emitting material contained in the light-emitting layer has a short light-emitting wavelength (for example, blue light-emitting). Since the first organic compound can supply high energy to the light-emitting material with a short light-emitting wavelength, the light-emitting efficiency of the light-emitting device can be improved.
[0147] <<Basic structure of light emitting device>> The basic structure of a light emitting device is described. Figure 1A The light-emitting device includes an organic compound layer (EL layer) having a light-emitting layer between a pair of electrodes. Specifically, the EL layer 103 is included between the first electrode 101 and the second electrode 102.
[0148] Figure 1B It is shown that a pair of electrodes includes multiple (in Figure 1B A light-emitting device having a stacked structure (tandem structure) including two EL layers (103a, 103b) and a charge generation layer 106 between the EL layers. A light-emitting device having a tandem structure can realize a highly efficient light-emitting device without changing the amount of current.
[0149] The charge generation layer 106 has a function of injecting electrons into one EL layer (103a or 103b) and injecting holes into the other EL layer (103b or 103a) when a potential difference is generated between the first electrode 101 and the second electrode 102. Figure 1B In the embodiment, when a voltage is applied so that the potential of the first electrode 101 is higher than that of the second electrode 102, the charge generation layer 106 injects electrons into the EL layer 103a and injects holes into the EL layer 103b.
[0150] In terms of light extraction efficiency, the charge generation layer 106 preferably has a light transmittance to visible light (specifically, the charge generation layer 106 has a visible light transmittance of 40% or more). The charge generation layer 106 can function even if its conductivity is lower than that of the first electrode 101 and the second electrode 102 .
[0151] Figure 1C The stacked structure of the EL layer 103 of the light-emitting device of one embodiment of the present invention is shown. Note that in this case, the first electrode 101 is used as an anode and the second electrode 102 is used as a cathode. The EL 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 stacked in sequence on the first electrode 101. Note that the light-emitting layer 113 may also be a stack of multiple light-emitting layers with different luminescent colors. For example, a light-emitting layer containing a light-emitting substance that emits red light, a light-emitting layer containing a light-emitting substance that emits green light, and a light-emitting layer containing a light-emitting substance that emits blue light may be stacked with or without a layer containing a carrier transport material. Alternatively, a light-emitting layer containing a light-emitting substance that emits yellow light and a light-emitting layer containing a light-emitting substance that emits blue light may be combined. Note that the stacked structure of the light-emitting layer 113 is not limited to the above structure. For example, the light-emitting layer 113 may also be a stack of multiple light-emitting layers with the same luminescent color. For example, a first light-emitting layer containing a light-emitting substance that emits blue light and a second light-emitting layer containing a light-emitting substance that emits blue light may be stacked with or without a layer containing a carrier transporting material. When multiple light-emitting layers having the same light-emitting color are stacked, reliability may be improved compared to a single layer. Figure 1B When the tandem structure shown includes a plurality of EL layers, the EL layers are stacked in order from the anode side as described above. In addition, when the first electrode 101 is a cathode and the second electrode 102 is an anode, the stacking order of the EL layer 103 is reversed. Specifically, 111 on the first electrode 101 of the cathode is an electron injection layer, 112 is an electron transport layer, 113 is a light-emitting layer, 114 is a hole transport layer, and 115 is a hole injection layer.
[0152] Each light-emitting layer 113 in the EL layer (103, 103a, 103b) contains a light-emitting substance or a plurality of substances in appropriate combination. Figure 1B The plurality of EL layers (103a and 103b) shown in the figure have a structure in which different luminescent colors are obtained. In this case, different materials may be used as the luminescent substance and other substances used in the respective luminescent layers.
[0153] In addition, in a light-emitting device according to one embodiment of the present invention, for example, Figure 1C The first electrode 101 shown is a reflective electrode, the second electrode 102 is a semi-transmissive-semi-reflective electrode and an optical microcavity resonator (microcavity) structure is adopted, so that the light obtained from the light-emitting layer 113 in the EL layer 103 can resonate between the above-mentioned electrodes, thereby enhancing the light emitted from the second electrode 102.
[0154] In the case where the first electrode 101 of the light-emitting device is a reflective electrode composed of a laminated structure of a reflective conductive material and a light-transmitting conductive material (transparent conductive film), optical adjustment can be performed by controlling the thickness of the transparent conductive film. Specifically, it is preferably adjusted in the following manner: when the wavelength of light obtained from the light-emitting layer 113 is λ, the optical distance (the 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 1) or a value close thereto.
[0155] In order to amplify the desired light (wavelength: λ) obtained from the light-emitting layer 113, it is preferable to adjust the optical distance from the first electrode 101 to the region (light-emitting region) in the light-emitting layer 113 where the desired light can be obtained and the optical distance from the second electrode 102 to the region (light-emitting region) in the light-emitting layer 113 where the desired light can be obtained to (2m'+1)λ / 4 (note that m' is an integer greater than 0) or a value in the vicinity thereof. Note that the "light-emitting region" described here refers to the region where holes and electrons in the light-emitting layer 113 recombine.
[0156] By performing the above optical adjustment, 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.
[0157] In addition, in the above case, strictly speaking, the optical distance between the first electrode 101 and the second electrode 102 can be said to be 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 above effect can be fully obtained by assuming that any position in the first electrode 101 and the second electrode 102 is a reflective region. In addition, strictly speaking, the optical distance between the first electrode 101 and the light-emitting layer that can obtain the desired light can be said to be the optical distance between the reflective region in the first electrode 101 and the light-emitting region in the light-emitting layer that can obtain the desired light. However, since it is difficult to accurately determine the positions of the reflective region in the first electrode 101 and the light-emitting region in the light-emitting layer that can obtain the desired light, the above effect can be fully obtained by assuming that any position in the first electrode 101 is a reflective region and any position in the light-emitting layer that can obtain the desired light is a light-emitting region.
[0158] Figure 1D Show Figure 1C A modified example of the stacked structure shown. In this case, the first electrode 101 is used as an anode and the second electrode 102 is used as a cathode. In this modified example, the hole transport layer 112 and the electron transport layer 114 both have a two-layer stacked structure. In other words, the EL layer 103 has a structure in which a hole injection layer 111, a first hole transport layer 112-1, a second hole transport layer 112-2, a light-emitting layer 113, a second electron transport layer 114-2, a first electron transport layer 114-1 and an electron injection layer 115 are sequentially stacked on the first electrode 101. Note that the light-emitting layer 113 is located between the first electrode 101 and the second electrode 102. In addition, the first hole transport layer 112-1 is located between the first electrode 101 and the light-emitting layer 113. In addition, the first electron transport layer 114-1 is located between the light-emitting layer 113 and the second electrode 102. In addition, the hole injection layer 111 is located between the first electrode 101 and the hole transport layer 112. In addition, the electron injection layer 115 is located between the electron transport layer 114 and the second electrode 102. In addition, the second hole transport layer 112-2 is located between the first hole transport layer 112-1 and the light-emitting layer 113. In addition, it can also be said that the second electron transport layer 114-2 is located between the light-emitting layer 113 and the first electron transport layer 114-1. When the EL layer 103 has the above-mentioned stacked structure, any one or more of the hole injection layer 111, the hole transport layer 112 and the light-emitting layer 113 preferably contains the first organic compound.
[0159] The second hole transport layer 112-2 is provided, for example, to prevent electrons from passing through the first electrode 101 from the light-emitting layer 113. Therefore, the second hole transport layer 112-2 may also be referred to as an electron blocking layer. In addition, the second electron transport layer 114-2 is provided, for example, to prevent holes from passing through the second electrode 102 from the light-emitting layer 113. Therefore, the second electron transport layer 114-2 may also be referred to as a hole blocking layer.
[0160] Figure 1E The light-emitting device shown is a light-emitting device having a series structure and a microcavity structure, so light of different wavelengths (monochromatic light) can be extracted from each EL layer (103a, 103b). Therefore, in order to obtain different luminous colors, it is not necessary to apply them separately (for example, apply them as R, G, and B). As a result, high resolution can be easily achieved. In addition, it can be combined with a coloring layer (color filter). In addition, the luminous intensity in the front direction with a specific wavelength can be enhanced, thereby achieving low power consumption.
[0161] Figure 1F The light emitting device shown is Figure 1B An example of a tandem structure light-emitting device shown in the figure has a structure in which three EL layers (103a, 103b, 103c) are stacked with charge generation layers (106a, 106b) sandwiched therebetween. The three EL layers (103a, 103b, 103c) respectively include light-emitting layers (113a, 113b, 113c), and the light-emitting colors of each light-emitting layer can be freely combined. For example, the light-emitting layer 113a and the light-emitting layer 113c can exhibit blue, and the light-emitting layer 113b can exhibit any one of red, green, and yellow. In addition, the light-emitting layer 113a and the light-emitting layer 113c can exhibit red, and the light-emitting layer 113b can exhibit any one of blue, green, and yellow.
[0162] Figure 2 A schematic diagram showing a light-emitting device including a light-emitting device 100A and a light-emitting device 100B according to one embodiment of the present invention. Both the light-emitting device 100A and the light-emitting device 100B are light-emitting devices in which a part of an organic compound layer (EL layer) is processed using a lithography technique.
[0163] The light-emitting device 100A is located on the insulating layer 175 and includes a first electrode 101A having an anode, a second electrode 102 having a cathode, and an EL layer 103A. The EL layer 103A is located between the first electrode 101A and the second electrode 102. The EL layer 103A includes at least a light-emitting layer 113A. In addition, the light-emitting layer 113A contains at least a light-emitting substance. Figure 2An example is shown in which the EL layer 103A includes a hole injection layer 111A, a hole transport layer 112A, an electron transport layer 108A, and an electron injection layer 109 in addition to the light-emitting layer 113A. That is, Figure 2 The EL layer 103A shown includes a hole injection layer 111A, a hole transport layer 112A, a light-emitting layer 113A, an electron transport layer 108A, and an electron injection layer 109 in this order.
[0164] The light-emitting device 100B is located on the insulating layer 175 and includes a first electrode 101B having an anode, a second electrode 102 having a cathode, and an EL layer 103B. The EL layer 103B is located between the first electrode 101B and the second electrode 102. The EL layer 103B includes at least a light-emitting layer 113B. In addition, the light-emitting layer 113B contains at least a light-emitting substance. Figure 2 An example is shown in which the EL layer 103B includes a hole injection layer 111B, a hole transport layer 112B, an electron transport layer 108B, and an electron injection layer 109 in addition to the light-emitting layer 113B. That is, Figure 2 The EL layer 103B shown includes a hole injection layer 111B, a hole transport layer 112B, a light-emitting layer 113B, an electron transport layer 108B, and an electron injection layer 109 in this order.
[0165] By using the first organic compound in either or both of the EL layer 103A of the light-emitting device 100A and the EL layer 103B of the light-emitting device 100B, it is possible to obtain the same structure as when the first organic compound is used in the EL layer 103A. Figure 1A The same effect is achieved as in the case of the EL layer 103 of the light-emitting device 100 shown.
[0166] In the light-emitting device 100A, each layer other than the electron injection layer 109 in the EL layer 103A is processed using a lithography technique. Therefore, each layer other than the electron injection layer 109 in the EL layer 103A is separated from the light-emitting device 100B, which is an adjacent light-emitting device. In addition, the ends (contours) of each layer other than the electron injection layer 109 in the EL layer 103A are aligned or approximately aligned in a direction perpendicular to the substrate. That is, the ends of the hole injection layer 111A, the hole transport layer 112A, the light-emitting layer 113A, and the electron transport layer 108A are separated from the hole transport layer 111B, the hole transport layer 112B, the light-emitting layer 113B, and the electron transport layer 108B. In addition, the ends (contours) of the hole injection layer 111A, the hole transport layer 112A, the light-emitting layer 113A, and the electron transport layer 108A are aligned or approximately aligned in a direction perpendicular to the substrate.
[0167] In the light-emitting device 100B, each layer other than the electron injection layer 109 in the EL layer 103B is processed using a lithography technique. Therefore, each layer other than the electron injection layer 109 in the EL layer 103B is separated from the light-emitting device 100A, which is an adjacent light-emitting device. In addition, the ends (contours) of each layer other than the electron injection layer 109 in the EL layer 103B are aligned or approximately aligned in a direction perpendicular to the substrate. That is, the ends of the hole injection layer 111B, the hole transport layer 112B, the light-emitting layer 113B, and the electron transport layer 108B are separated from the hole injection layer 111A, the hole transport layer 112A, the light-emitting layer 113A, and the electron transport layer 108A. In addition, the ends (contours) of the hole injection layer 111A, the hole transport layer 112A, the light-emitting layer 113A, and the electron transport layer 108A are aligned or approximately aligned in a direction perpendicular to the substrate.
[0168] The electron injection layer 109 and the second electrode 102 are preferably formed after processing each layer other than the electron injection layer 109 in the EL layer 103A and each layer other than the electron injection layer 109 in the EL layer 103B by using a lithography technique. That is, the electron injection layer 109 and the second electrode 102 are preferably continuous layers used in common by the light-emitting device 100A and the light-emitting device 100B.
[0169] The voltage of the light-emitting device can be reduced by using a donor substance (also called an electron donor) in the electron injection layer 109. Specific examples of the donor substance include alkali metals such as lithium (Li) having a small work function or compounds of the alkali metals.
[0170] When the electron injection layer containing such a donor substance is processed as the top surface (or interface) of the EL layer by lithography, the driving voltage of the light-emitting device may increase significantly or the current efficiency may decrease significantly due to the influence of oxygen or water in the atmosphere or the chemical solution or water in the process. However, in one embodiment of the present invention, the electron injection layer 109 is formed after each layer other than the electron injection layer 109 is processed by lithography, thereby avoiding the degradation of the characteristics of the light-emitting device even if a donor substance is used as the electron injection layer 109.
[0171] Note that by processing the EL layer using lithography, the distance d between each layer other than the electron injection layer 109 of the EL layer 103a and each layer other than the electron injection layer 109 of the EL layer 103b can be reduced compared to the case of performing mask evaporation. Specifically, the distance d can be reduced to less than 10 μm, 8 μm or less, 5 μm or less, 3 μm or less, 2 μm or less, 1.5 μm or less, 1 μm or less, or 0.5 μm or less. In addition, by using an exposure apparatus for LSI, for example, in a process on a silicon wafer, the distance d can be reduced to, for example, 500 nm or less, 200 nm or less, 100 nm or less, or even 50 nm or less.
[0172] In addition, it is preferable that a partition wall 128 is provided in the gap between the layers other than the electron injection layer 109 of the EL layer 103a and the layers other than the electron injection layer 109 of the EL layer 103b. The layers other than the electron injection layer 109 of the EL layer 103A can be separated from the layers other than the electron injection layer 109 of the EL layer 103B. In this case, it can be said that the partition wall 128 is provided in a region surrounded by the insulating layer 175, the ends of the layers other than the electron injection layer 109 of the EL layer 103A, and the ends of the electron injection layer 109 and the ends of the layers other than the electron injection layer 109 of the EL layer 103B. In this case, it can be said that there is a region in which the partition wall 128 is in contact with the electron injection layer 109 or the second electrode 102. Note that in Figure 2 In the embodiment, the partition wall 128 is in contact with the end of each layer other than the electron injection layer 109 of the EL layer 103A and the end of each layer other than the electron injection layer 109 of the EL layer 103B, but the present invention is not limited to this structure. For example, the following structure may be adopted: the end of each layer other than the electron injection layer 109 of the EL layer 103A and the end of each layer other than the electron injection layer 109 of the EL layer 103B are respectively provided with an insulating layer, and the partition wall 128 is located at the end of each layer other than the electron injection layer 109 of the EL layer 103A and the end of each layer other than the electron injection layer 109 of the EL layer 103B via the insulating layer.
[0173] When the EL layer is processed by lithography as in the light-emitting device 100A and the light-emitting device 100B, the processed surface of the EL layer other than the electron injection layer 109 is also exposed to oxygen or water in the atmosphere, chemical solution or water in the process, heat treatment, etc. Therefore, problems such as crystallization of the EL layer may occur, and the reliability and brightness of the light-emitting device may decrease. This tendency is observed when the heat resistance of the organic compound used for the light-emitting device is low, so it is preferable to use T for the EL layer when processing by lithography. g By using T gThe high first organic compound can prevent the thickness change and film quality change such as crystallization of the EL layer due to heating and heat generation, so the brightness and reliability of the light-emitting device 100A and the light-emitting device 100B can be improved.
[0174] T of the first organic compound g The temperature is preferably 100° C. or higher, more preferably 110° C. or higher, 120° C. or higher, 130° C. or higher, or 140° C. or higher. Thus, when the processed surface of the EL layer is exposed to oxygen or water in the atmosphere, a chemical solution or water in the process, or heat treatment, the film quality change can be suppressed. Thus, the reliability of the light-emitting device 100 can be improved.
[0175] In addition, in the light-emitting device of one embodiment of the present invention, at least one of the first electrode 101 and the second electrode 102 is a light-transmitting electrode (transparent electrode, semi-transmitting-semi-reflecting electrode, etc.). In the case where the light-transmitting electrode is a transparent electrode, the visible light transmittance of the transparent electrode is 40% or more. In addition, in the case where the electrode is a semi-transmitting-semi-reflecting electrode, the visible light reflectance of the semi-transmitting-semi-reflecting electrode is 20% or more and 80% or less, preferably 40% or more and 70% or less. In addition, the resistivity of these electrodes is preferably 1×10 -2 Ωcm or less.
[0176] In the light-emitting device of one embodiment of the present invention, when one of the first electrode 101 and the second electrode 102 is a reflective electrode (reflective electrode), the reflective electrode has a visible light reflectivity of 40% to 100%, preferably 70% to 100%. In addition, the resistivity of the electrode is preferably 1×10- 2 Ωcm or less.
[0177] <<Specific structure of the light emitting device>> Next, the specific structure of the light emitting device of one embodiment of the present invention is described. Figure 1E Note: Figure 1A and Figure 1C The light emitting device having a single structure shown also has the same structure of the EL layer. Figure 1E In the case where the light-emitting device shown has 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 desired electrode material alone or using a plurality of electrode materials in a single layer or a stacked layer. In addition, the second electrode 102 is formed by appropriately selecting a material after forming the EL layer 103b.
[0178] <First Electrode and Second Electrode> As the material forming the first electrode 101 and the second electrode 102, if the functions of the above two electrodes can be satisfied, the following materials can be appropriately combined. For example, metals, alloys, conductive compounds and mixtures thereof can be appropriately used. Specifically, In-Sn oxide (also called ITO), In-Si-Sn oxide (also called ITSO), In-Zn oxide, In-W-Zn oxide can be cited. In addition to the above, 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 other metals and alloys appropriately combined therewith can also be cited. In addition to the above, elements belonging to Group 1 or Group 2 of the periodic table (for example, lithium (Li), cesium (Cs), calcium (Ca), strontium (Sr)), rare earth metals such as europium (Eu), ytterbium (Yb), alloys appropriately combined therefrom, and graphene, etc. can be used.
[0179] exist Figure 1E In the light-emitting device shown, when the first electrode 101 is an anode, the hole injection layer 111a and the hole transport layer 112a of the EL layer 103a are sequentially stacked on the first electrode 101 by vacuum evaporation. After the EL layer 103a and the charge generation layer 106 are formed, the hole injection layer 111b and the hole transport layer 112b of the EL layer 103b are sequentially stacked on the charge generation layer 106 in the same manner as described above.
[0180] In addition, Figure 1E In the light-emitting device shown, by making the first electrode 101 a reflective electrode, making the second electrode 102 a semi-transmissive-semi-reflective electrode and adopting an optical microcavity resonator (microcavity) structure, the light obtained from the light-emitting layer 113 in the EL layer 103 can resonate between the above-mentioned electrodes, thereby enhancing the light emitted from the second electrode 102.
[0181] In the case where the first electrode 101 of the light-emitting device is a reflective electrode composed of a laminated structure of a reflective conductive material and a light-transmitting conductive material (transparent conductive film), optical adjustment can be performed by controlling the thickness of the transparent conductive film. Specifically, it is preferably adjusted in the following manner: when the wavelength of light obtained from the light-emitting layer 113 is λ, the optical distance (the 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 1) or a value close thereto.
[0182] In order to amplify the desired light (wavelength: λ) obtained from the light-emitting layer 113, it is preferable to adjust the optical distance from the first electrode 101 to the region (light-emitting region) in the light-emitting layer 113 where the desired light can be obtained and the optical distance from the second electrode 102 to the region (light-emitting region) in the light-emitting layer 113 where the desired light can be obtained to (2m'+1)λ / 4 (note that m' is an integer greater than 1) or a value in the vicinity thereof. Note that the "light-emitting region" described here refers to the region where holes and electrons in the light-emitting layer 113 recombine.
[0183] By performing the above optical adjustment, 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.
[0184] In addition, in the above case, strictly speaking, the optical distance between the first electrode 101 and the second electrode 102 can be said to be 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 above effect can be fully obtained by assuming that any position in the first electrode 101 and the second electrode 102 is a reflective region. In addition, strictly speaking, the optical distance between the first electrode 101 and the light-emitting layer that can obtain the desired light can be said to be the optical distance between the reflective region in the first electrode 101 and the light-emitting region in the light-emitting layer that can obtain the desired light. However, since it is difficult to accurately determine the positions of the reflective region in the first electrode 101 and the light-emitting region in the light-emitting layer that can obtain the desired light, the above effect can be fully obtained by assuming that any position in the first electrode 101 is a reflective region and any position in the light-emitting layer that can obtain the desired light is a light-emitting region.
[0185] In addition, in the light-emitting device of one embodiment of the present invention, at least one of the first electrode 101 and the second electrode 102 is a light-transmitting electrode (transparent electrode, semi-transmitting-semi-reflecting electrode, etc.). In the case where the light-transmitting electrode is a transparent electrode, the visible light transmittance of the transparent electrode is 40% or more. In addition, in the case where the electrode is a semi-transmitting-semi-reflecting electrode, the visible light reflectance of the semi-transmitting-semi-reflecting electrode is 20% or more and 80% or less, preferably 40% or more and 70% or less. In addition, the resistivity of these electrodes is preferably 1×10 -2 Ωcm or less.
[0186] In the light-emitting device of one embodiment of the present invention, when one of the first electrode 101 and the second electrode 102 is a reflective electrode (reflective electrode), the reflective electrode has a visible light reflectivity of 40% to 100%, preferably 70% to 100%. In addition, the resistivity of the electrode is preferably 1×10 -2 Ωcm or less.
[0187] <Hole Injection Layer> The hole injection layer (111, 111a, 111b) is a layer for injecting holes from the anode first electrode 101 and the charge generation layer (106, 106a, 106b) into the EL layer (103, 103a, 103b), and contains an organic acceptor material and a material with high hole injection properties.
[0188] The organic acceptor material can generate holes in the organic compound by charge separation with other organic compounds whose HOMO energy level is close to the LUMO energy level. Therefore, compounds having an electron-withdrawing group (halogen or cyano) such as quinone dimethane derivatives, tetrachlorobenzoquinone derivatives, and hexaazatriphenylene derivatives can be used as organic acceptor materials. For example, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ), 3,6-difluoro-2,5,7,7,8,8-hexacyanoquinodimethane, chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN), 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ), 2-(7-dicyanomethylidene-1,3,4,5,6,8,9,10-octafluoro-7H-pyrene-2-ylidene)malononitrile, etc. can be used. Among organic acceptor materials, compounds such as HAT-CN, etc., in which electron-withdrawing groups are bonded to fused aromatic rings having multiple heteroatoms, have high acceptability and the film quality has thermal stability, so they are particularly preferred. In addition, [3] axial ene derivatives including electron-withdrawing groups (especially halogen groups such as fluorine groups or cyano groups) have very high electron acceptability and are therefore preferred. Specifically, α, α', α"-1,2,3-cyclopropane trimethylene tris[4-cyano-2,3,5,6-tetrafluorophenylacetonitrile], α, α', α"-1,2,3-cyclopropane trimethylene tris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)phenylacetonitrile], α, α', α"-1,2,3-cyclopropane trimethylene tris[2,3,4,5,6-pentafluorophenylacetonitrile], etc. can be used.
[0189] As a material with high hole injection property, oxides of metals belonging to Groups 4 to 8 in the periodic table (transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide, etc.) can be used. Specifically, molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide, and rhenium oxide can be cited. Among them, molybdenum oxide is particularly stable in the atmosphere, has low hygroscopicity, and is easy to handle, so it is preferred. In addition, perylenetetracarboxylic acid derivatives such as diquinoxalino[2,3-a:2',3'-c]phenazine (abbreviation: HATNA), 2,3,8,9,14,15-hexafluorodiquinoxalino[2,3-a:2',3'-c]phenazine (abbreviation: HATNA-F6), 3,4,9,10-perylenetetracarboxylic acid diimide (abbreviation: PTCDI), 3,4,9,10-perylenetetracarboxylic acid-bis-benzimidazole (abbreviation: PTCBI), (C 60 -Ih)[5,6]fullerene (abbreviation: C 60 )、(C 70 -D5h)[5,6]fullerene (abbreviation: C 70 ), organic compounds such as phthalocyanine (abbreviation: H2Pc), copper phthalocyanine (abbreviation: CuPc), zinc phthalocyanine (abbreviation: ZnPc), cobalt phthalocyanine (abbreviation: CoPc), iron phthalocyanine (abbreviation: FePc), tin phthalocyanine (abbreviation: SnPc), tin phthalocyanine oxide (abbreviation: SnOPc), titanium phthalocyanine oxide (abbreviation: TiOPc), vanadium phthalocyanine oxide (abbreviation: VOPc), etc., metal phthalocyanines containing copper, zinc, cobalt, iron, chromium, nickel, etc. and their derivatives, or metal complexes containing metal-oxygen bonds and aromatic ligands. In addition, phthalocyanine metal complexes such as CuPc or ZnPc or 2,3,8,9,14,15-hexafluorobisquinoxalino[2,3-a:2',3'-c]phenazine are particularly preferably used. In particular, CuPc and ZnPc are inexpensive and have good properties, so they are preferred. Furthermore, ZnPc has a small diffusion coefficient with respect to silicon, and the possibility of the metal diffusing into the semiconductor and affecting the semiconductor characteristics is reduced. Therefore, ZnPc is particularly suitable for use in display devices using silicon semiconductors.
[0190] In addition to the above materials, the following low molecular weight aromatic amine compounds can be used, such as 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviated as TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated as MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated as DPAB), N,N'-bis-[4-bis(3-methylphenyl)aminophenyl]-N,N'-diphenyl-4,4'-diaminobiphenyl benzene (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), etc.
[0191] In addition, a polymer compound (oligomer, dendrimer or polymer, etc.) can be used, such as poly(N-vinylcarbazole) (abbreviated as PVK), poly(4-vinyltriphenylamine) (abbreviated as PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated as PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated as Poly-TPD), etc. Alternatively, a polymer compound to which an acid is added, such as poly(3,4-ethylenedioxythiophene) / polystyrene sulfonic acid (abbreviated as PEDOT / PSS), polyaniline / polystyrene sulfonic acid (abbreviated as PAni / PSS), etc. can also be used.
[0192] As a material with high hole injection property, a mixed material containing a hole transport material and the above-mentioned organic acceptor material (electron acceptor material) can also be used. In this case, the organic acceptor material extracts electrons from the hole transport material to generate holes in the hole injection layer 111, and the holes are injected into the light-emitting layer 113 through the hole transport layer 112. In addition, the hole injection layer 111 can be a single layer composed of a mixed material containing a hole transport material and an organic acceptor material (electron acceptor material), or a stack of layers formed using a hole transport material and an organic acceptor material (electron acceptor material) respectively.
[0193] As a hole transport material, it is preferable to use a hole transport material having a hole mobility of 1×10 -6 cm2 / Vs or more. In addition, any substance other than the above may be used as long as it has a higher hole-transporting property than an electron-transporting property.
[0194] As hole transport materials, it is preferred to use materials with high hole transport properties such as compounds having π-electron-rich heteroaromatic rings (e.g., carbazole derivatives, furan derivatives, or thiophene derivatives) and aromatic amines (organic compounds containing aromatic amine skeletons). When the first organic compound has hole transport properties, it can be used as a hole transport material.
[0195] Examples of the carbazole derivative (organic compound having a carbazole ring) include bicarbazole derivatives (eg, 3,3′-bicarbazole derivatives) and aromatic amines having a carbazole group.
[0196] As the above-mentioned bicarbazole derivatives (for example, 3,3'-bicarbazole derivatives), specifically, there can be mentioned 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(1,1'-biphenyl-3-yl)-3,3'-bi-9H-carbazole (abbreviated as: BismBPCz), 9-(biphenyl-3-yl)-9'-(biphenyl-4-yl)-9H,9'H-3,3'-bicarbazole (abbreviated as: mBPCCBP), 9-(2-naphthyl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviated as: βNCCP), etc.
[0197] In addition, as the aromatic amine having the above-mentioned carbazole group, specifically, 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBA1BP), N-(biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9-phenyl-9H-carbazole-3-amine (abbreviation: PCBiF), N-(biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H-fluorene-2-amine (abbreviation: PCBBiF), N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-bis(9,9-dimethyl-9H-fluorene-2-yl)amine (abbreviation: PCBiF), PCBFF), N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-diphenyl-9H-fluorene-4-amine, N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-(9,9-diphenyl-9H-fluorene-2-yl)-9,9-diphenyl-9H-fluorene-4-amine, N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-diphenyl-9H-fluorene-2-amine, N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-diphenyl-9H-fluorene -4-amine, N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9'-spirobi(9H-fluorene)-2-amine, N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9'-spirobi(9H-fluorene)-4-amine, N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-N-(1,1':3',1"-terphenyl-4-yl)-9,9-dimethylbenzene-9H-fluorene-2-amine, N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-N-(1,1':4',1"-terphenyl-4-yl)- 9,9-Dimethylbenzene-9H-fluoren-2-amine, N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-N-(1,1':3',1"-terphenyl-4-yl)-9,9-dimethylbenzene-9H-fluoren-4-amine, N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-N-(1,1':4',1"-terphenyl-4-yl)-9,9-dimethylbenzene-9H-fluoren-4-amine, 4,4'-diphenyl-4"-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as: PCBANB), 4,4'-di(1-naphthyl)-4"-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as: PCBNBB), 4-phenyldiphenyl-(9-phenyl-9H-carbazole-3-yl)amine (abbreviated as: PCA1BP), N,N'-bis(9-phenylcarbazole-3-yl)-N,N'-diphenylbenzene-1,3-diamine (abbreviated as: PCA2B), N,N',N"-triphenyl-N,N',N"-tri(9-phenylcarbazole-3-yl)benzene-1,3,5-triamine (abbreviated as: PCA3B), 9,9- dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9'-spirobi[9H-fluoren]-2-amine (abbreviation: PCBASF), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenyl Carbazole (abbreviated as PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviated as PCzPCN1), 3-[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzDPA1), 3,6-bis[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzDPA2), 3,6-bis[N-(4-diphenylaminophenyl)-N-(1-naphthyl)amino] -9-phenylcarbazole (abbreviated as PCzTPN2), N-(9,9-spirobi[9H-fluorene]-2-yl)-N,9-diphenylcarbazole-3-amine (abbreviated as PCASF), N-(4-biphenyl)-4-(carbazole-9-yl)phenylaniline (abbreviated as YGA1BP), N,N'-bis[4-(carbazole-9-yl)phenyl]-N,N'-diphenyl-9,9-dimethylfluorene-2,7-diamine (abbreviated as YGA2F), 4,4',4"-tris(carbazole-9-yl)triphenylamine (abbreviated as TCTA), etc.
[0198] Note that as carbazole derivatives, in addition to the above, 9-[4-(9-phenyl-9H-carbazol-3-yl)-phenyl]phenanthrene (abbreviation: PCPPn), 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-bis(N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviation: CzTP), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), etc. can also be mentioned.
[0199] Specific examples of the above-mentioned furan derivatives (organic compounds having a furan ring) include 4,4',4"-(benzene-1,3,5-triyl)tris(dibenzofuran) (abbreviation: DBF3P-II), 4-{3-[3-(9-phenyl-9H-fluorene-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II), and the like.
[0200] Specific examples of the above-mentioned thiophene derivatives (organic compounds having a thiophene ring) include 4,4',4"-(benzene-1,3,5-triyl)tris(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluorene-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), and 4-[4-(9-phenyl-9H-fluorene-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV).
[0201] Specific examples of the aromatic amines include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminobiphenyl (abbreviation: TPD), N,N'-bis(9,9'-spirobi[9H-fluorene]-2-yl)-N,N'-diphenyl-4,4'-diaminobiphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluorene-9-yl)triphenylamine (abbreviation: mBPAFLP), N-(9,9-dimethyl-9H-fluorene-2-yl)triphenylamine (abbreviation: mBPAFLP), and N-(9,9-dimethyl-9H-fluorene-2-yl)triphenylamine. -N-{9,9-dimethyl-2-[N'-phenyl-N'-(9,9-dimethyl-9H-fluoren-2-yl)amino]-9H-fluoren-7-yl}phenylamine (abbreviation: DFLADFL), N-(9,9-dimethyl-2-diphenylamino-9H-fluoren-7-yl)diphenylamine (abbreviation: DPNF), N-(9,9-spirobi[9H-fluoren]-2-yl)-N,N,'N'-triphenyl-1,4-phenylenediamine (abbreviation: DPASF), N,N'-diphenyl-N,N'-bis(4-diphenylaminophenyl)spirobi[9H-fluoren]-2,7-diamine (abbreviation: DPA2SF), 4,4',4"-tri[N-(1-naphthyl)-N-phenylamino]tri Aniline (abbreviation: 1'-TNATA), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: m-MTDATA), N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), DNTPD, 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), N-(4-biphenyl)-6,N-diphenylbenzo[b]naphtho [1,2-d]furan-8-amine (abbreviation: BnfABP), N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf), 4,4'-bis(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)-4"-phenyltriphenylamine (abbreviation: BnfBB1BP), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-6-amine (abbreviation: BBABnf(6)), N,N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: BBABnf(8)), N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d] furan-4-amine (abbreviation: BBABnf(II)(4)), N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP), N-[4-(dibenzothiophen-4-yl)phenyl]-N-phenyl-4-benzidine (abbreviation: ThBA1BP), 4-(2-naphthyl)-4',4"-diphenyltriphenylamine (abbreviation: BBAβNB), 4-[4-(2-naphthyl)phenyl]-4',4"-diphenyltriphenylamine (abbreviation: BBAβNBi), 4,4'-diphenyl-4"-(6;1'-binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβNB), 4,4'-diphenyl- 4"-(7;1'-binaphthyl-2-yl)triphenylamine (abbreviated as: BBAαNβNB-03), 4,4'-diphenyl-4"-(7-phenyl)naphthyl-2-yltriphenylamine (abbreviated as: BBAPβNB-03), 4,4'-diphenyl-4"-(6;2'-binaphthyl-2-yl)triphenylamine (abbreviated as: BBA(βN2)B), 4,4'-diphenyl-4"-(7;2'-binaphthyl-2-yl)triphenylamine (abbreviated as: BBA(βN2)B-03), 4,4'-diphenyl-4"-(4;2'-binaphthyl-1-yl)triphenylamine (abbreviated as: BBAβNαNB), 4,4'-diphenyl-4"-(5;2'-binaphthyl-1-yl)triphenylamine amine (abbreviated as: BBAβNαNB-02), 4-(4-biphenyl)-4'-(2-naphthyl)-4"-phenyltriphenylamine (abbreviated as: TPBiAβNB), 4-(3-biphenyl)-4'-[4-(2-naphthyl)phenyl]-4"-phenyltriphenylamine (abbreviated as: mTPBiAβNBi), 4-(4-biphenyl)-4'-[4-(2-naphthyl)phenyl]-4"-phenyltriphenylamine (abbreviated as: TPBiAβNBi), 4-phenyl-4'-(1-naphthyl)triphenylamine (abbreviated as: αNBA1BP), 4,4'-bis(1-naphthyl)triphenylamine (abbreviated as: αNBB1BP), 4,4'-diphenyl-4"-[4'-(carbazol-9-yl)biphenyl 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'-spirobi[9H-fluorene]-2-amine (abbreviation: PCBNBSF), N,N-bis(biphenyl-4-yl)-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: BBASF), N,N-bis(biphenyl-4-yl)-9,9'-spirobi[9H-fluorene]-4-amine (abbreviation: BBASF(4)), N-(biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobi[9H-fluorene]-4-amine (abbreviation: oFBiSF), N-(biphenyl-4-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl)dibenzofuran-4-amine (abbreviation: FrBiF), N-[4-(1-naphthyl)phenyl]-N-[3-(6-phenyldibenzofuran-4-yl)phenyl]-1-naphthylamine (abbreviation: mPDBfB NBN), 4-phenyl-4'-[4-(9-phenylfluorene-9-yl)phenyl]triphenylamine (abbreviated as: BPAFLBi), N,N-bis(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobi-9H-fluorene-4-amine, N,N-bis(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobi-9H-fluorene-3-amine, N,N-bis(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobi-9H-fluorene-2-amine, N,N-bis(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobi-9H-fluorene-1-amine, etc. ,
[0202] In addition, as hole transport materials, polymer compounds (oligomers, dendrimers, polymers, etc.) can be used, such as poly (N-vinyl carbazole) (abbreviated as: PVK), poly (4-vinyl triphenylamine) (abbreviated as: PVTPA), poly [N- (4-{N'-[4-(4-diphenylamino) phenyl] phenyl-N'-phenylamino} phenyl) methacrylamide] (abbreviated as: PTPDMA), poly [N, N'-bis (4-butylphenyl) -N, N'-bis (phenyl) benzidine] (abbreviated as: Poly-TPD), etc. Alternatively, polymer compounds to which an acid is added can be used, such as poly (3, 4-ethylenedioxythiophene) / polystyrene sulfonic acid (abbreviated as: PEDOT / PSS), polyaniline / polystyrene sulfonic acid (abbreviated as: PAni / PSS), etc.
[0203] Note that the hole-transporting material is not limited to the above materials, and a combination of one or more known various materials can be used as the hole-transporting material.
[0204] Note that the hole injection layer (111, 111a, 111b) can be formed by various known film-forming methods, for example, by vacuum evaporation.
[0205] <Hole Transport Layer> The hole transport layer (112, 112a, 112b) is a layer that transports holes injected from the hole injection layer (111, 111a, 111b) from the first electrode 101 to the light-emitting layer (113, 113a, 113b). In addition, the hole transport layer (112, 112a, 112b) is a layer containing a hole transport material. Therefore, as the hole transport layer (112, 112a, 112b), a hole transport material that can be used for the hole injection layer (111, 111a, 111b) can be used.
[0206] Note that in a light-emitting device of one embodiment of the present invention, the same organic compound as that of the hole transport layer (112, 112a, 112b) can be used for the light-emitting layer (113, 113a, 113b). When the same organic compound is used for the hole transport layer (112, 112a, 112b) and the light-emitting layer (113, 113a, 113b), holes can be efficiently transported from the hole transport layer (112, 112a, 112b) to the light-emitting layer (113, 113a, 113b), which is preferred.
[0207] <Luminous Layer> The light-emitting layer (113, 113a, 113b) is a layer containing a light-emitting substance. For the light-emitting substance that can be used for the light-emitting layer (113, 113a, 113b), substances that emit light in blue, purple, blue-purple, green, yellow-green, yellow, orange, red, etc. can be appropriately used. In addition, when a plurality of light-emitting layers are included, by using different light-emitting substances in each light-emitting layer, a structure that emits different light-emitting colors can be obtained (for example, light-emitting colors that are in a complementary color relationship can be combined to obtain white light). In addition, when a plurality of light-emitting layers are included, each light-emitting layer can also exhibit the same color. When multiple light-emitting layers with the same light-emitting color are stacked, reliability can sometimes be improved compared to a single layer. Furthermore, a stacked structure in which one light-emitting layer contains different light-emitting substances can also be adopted.
[0208] In addition, the light-emitting layer (113, 113a, 113b) may contain one or more organic compounds (host material, etc.) in addition to the light-emitting substance (guest material).
[0209] Note that when multiple host materials are used in the light-emitting layer (113, 113a, 113b), as the newly added second host material, it is preferred to use a substance having an energy gap larger than the energy gaps of the existing guest material and the first host material. In addition, it is preferred that the lowest singlet excitation energy level (S1 energy level) of the second host material is higher than the S1 energy level of the first host material, and the lowest triplet excitation energy level (T1 energy level) of the second host material is higher than the T1 energy level of the guest material. In addition, it is preferred that the lowest triplet excitation energy level (T1 energy level) of the second host material is higher than the T1 energy level of the first host material. By adopting the above structure, an excimer complex can be formed by two host materials. Note that in order to efficiently form an excimer complex, it is particularly preferred to combine a compound that easily receives holes (hole transport material) and a compound that easily receives electrons (electron transport material). In addition, by adopting the above structure, high efficiency, low voltage and long life can be achieved at the same time.
[0210] Note that as the organic compound used as the above-mentioned host material (including the first host material and the second host material), as long as the conditions for the host material used for the light-emitting layer are met, an organic compound such as a hole transport material that can be used for the above-mentioned hole transport layer (112, 112a, 112b) or an electron transport material that can be used for the electron transport layer (114, 114a, 114b) described later can be used, and an exciplex formed by multiple organic compounds (the above-mentioned first host material and the second host material) can also be used. In addition, the exciplex (Exciplex) formed by multiple organic compounds in an excited state has the function of a thermally activated delayed fluorescence (TADF) material that can convert triplet excitation energy into singlet excitation energy because the difference between the S1 energy level and the T1 energy level is extremely small. As a combination of multiple organic compounds that form an exciplex, for example, it is preferred that one has a π-electron-deficient heteroaromatic ring and the other has a π-electron-rich heteroaromatic ring. In addition, as one of the combinations forming an exciplex, a phosphorescent light-emitting substance such as an iridium, rhodium or platinum type organic metal complex or metal complex may be used. The first organic compound may also be used as a host material.
[0211] Note that when a first organic compound having a hole-transporting property is used as the first host material, an organic compound having a π-electron-deficient heteroaromatic ring (second organic compound) is used as the second host material, and in this case, it is preferable as a combination that forms an exciplex.
[0212] There is no particular limitation on the luminescent material that can be used in the luminescent layer (113, 113a, 113b), and a luminescent material that converts singlet excitation energy into light in the visible light region or a luminescent material that converts triplet excitation energy into light in the visible light region can be used.
[0213] <<Luminescent material that converts singlet excitation energy into luminescence>> As the luminescent material that can be used for the luminescent layer (113, 113a, 113b) and converts the singlet excitation energy into luminescence, the following fluorescent emitting materials (fluorescent luminescent materials) can be cited. For example, pyrene derivatives, anthracene derivatives, triphenylene derivatives, fluorene derivatives, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, dibenzoquinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives, phenanthrene derivatives, naphthalene derivatives, etc. can be cited. In particular, pyrene derivatives are preferred because of their high luminescence quantum yield. Specific examples of pyrene derivatives include N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N,N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-bis(dibenzofuran-2-yl)-N,N'-diphenylpyrene-1,6-diamine (abbreviation: 1,6FrAPrn), N,N'-bis(dibenzothiophene-2-yl)-N,N' -diphenylpyrene-1,6-diamine (abbreviation: 1,6ThAPrn), N,N'-(pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-6-amine] (abbreviation: 1,6BnfAPrn), N,N'-(pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-02), N,N'-(pyrene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03), etc.
[0214] In addition, 5,6-bis[4-(10-phenyl-9-anthracenyl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl-9-anthracenyl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylethylene-4,4'-ethylenediamine (abbreviation: PAP2BPy), triphenylamine (abbreviated as: 2YGAPPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole-3-amine (abbreviated as: PCAPA), 4-(9H-carbazole-9-yl)-4'-(10-phenyl-9-anthracenyl)triphenylamine (abbreviated as: YGA2S), 4-(9H-carbazole-9-yl)-4'-(10-phenyl-9-anthracenyl)triphenylamine (abbreviated as: YGAPA), 4-(9H-carbazole-9-yl)-4'-(9,10-diphenyl-2-anthracenyl)triphenylamine (abbreviated as: 2YGAPPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole-3-amine (abbreviated as: PCAPA), 4-(10 -phenyl-9-anthracenyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as: PCBAPA), 4-[4-(10-phenyl-9-anthracenyl)phenyl]-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as: PCBAPBA), dinaphthylene, 2,5,8,11-tetra-(tert-butyl) dinaphthylene (abbreviated as: TBP), N,N"-(2-tert-butylanthracene-9,10-diyl) di-4,1-phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine] (abbreviation: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: 2PCAPPA), N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA), etc.
[0215] In addition, N-[9,10-bis(biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), 9,10-bis(biphenyl-2-yl)-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N, 9-Triphenylanthracen-9-amine (abbreviated as DPhAPhA), coumarin 545T, N,N'-diphenylquinacridone (abbreviated as DPQd), rubrene, 5,12-bis(biphenyl-4-yl)-6,11-diphenylnaphthacene (abbreviated as BPT), 2-(2-{2-[4-(dimethylamino)phenyl]vinyl}-6-methyl-4H-pyran-4-ylidene)malononitrile (abbreviated as DCM1), 2-{2-methyl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)vinyl]-4H-pyran-4-ylidene}malononitrile (abbreviated as DCM2), N,N,N',N'-tetra(4- methylphenyl)tetracene-5,11-diamine (abbreviated as p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviated as p-mPhAFD), 2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)vinyl]-4H-pyran-4-ylidene}malononitrile (abbreviated as DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)vinyl]-4H-pyran-4-ylidene}malononitrile (abbreviated as DCJTI), )vinyl]-4H-pyran-4-ylidene}malononitrile (abbreviated as: DCJTB), 2-(2,6-bis{2-[4-(dimethylamino)phenyl]vinyl}-4H-pyran-4-ylidene)malononitrile (abbreviated as: BisDCM), 2-{2,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)vinyl]-4H-pyran-4-ylidene}malononitrile (abbreviated as: BisDCJTM), 1,6BnfAPrn-03, 3,10-bis[N-(9-phenyl-9H-carbazole-2-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nbf(IV)-02), 3,10-bis[N-(dibenzofuran-3-yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10FrA2Nbf(IV)-02), etc. In particular, pyrene diamine compounds such as 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6BnfAPrn-03 can be used. ;
[0216] <<Luminescent material that converts triplet excitation energy into luminescence>> Next, as a light-emitting substance that converts triplet excitation energy into light emission and can be used for the light-emitting layer 113, for example, a substance that emits phosphorescence (phosphorescent substance) or a TADF material can be mentioned.
[0217] Phosphorescent materials refer to compounds that exhibit phosphorescence but no fluorescence at any temperature in the temperature range (i.e., 77K or more and 313K or less) above low temperature (e.g., 77K or more and 313K or less) below room temperature. The phosphorescent material preferably contains a metal element with a large spin-orbit interaction, and an organic metal complex, a metal complex (platinum complex), a rare earth metal complex, etc. can be used. Specifically, it is preferred to contain a transition metal element, and it is particularly preferred to contain a platinum group element (ruthenium (Ru), rhodium (Rh), palladium (Pd), osmium (Os), iridium (Ir) or platinum (Pt)), and it is particularly preferred to contain iridium. Iridium can increase the probability of direct transition between the singlet ground state and the triplet excited state, so it is preferred.
[0218] <<Phosphorescent substances (450nm and above and 570nm and below: blue or green)>> Examples of phosphorescent substances that emit blue or green light and have an emission spectrum with a peak wavelength of 450 nm to 570 nm include the following substances.
[0219] For example, tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium(III) (abbreviated as [Ir(mpptz-dmp)3]), tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazole)iridium(III) (abbreviated as [Ir(Mptz)3]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazole]iridium(III) (abbreviated as [Ir(iPrptz-3b)3]), tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazole)iridium(III) (abbreviated as [Ir(Mptz)3]), tris(4-(3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazole)iridium(III) (abbreviated as [Ir(iPrptz-3b)3]), tris(5-methyl-3,4-di ... [3-(5-biphenyl)-5-isopropyl-4-phenyl-4H-1,2,4-triazole]iridium (III) (abbreviated as [Ir(iPr5btz)3]) and other organic metal complexes having a 4H-triazole ring; tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazole]iridium (III) (abbreviated as [Ir(Mptz1-mp)3]), tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazole)iridium (III) (abbreviated as [Ir(Prptz1-Me)3]) and other organic metal complexes having a 1H-triazole ring Organic metal complexes; organic metal complexes having an imidazole ring, such as fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviated as [Ir(iPrpim)3]), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviated as [Ir(dmpimpt-Me)3]); and bis[2-(4',6'-difluorophenyl)pyridinium-N,C2']iridium(III)tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridinium-N,C2']iridium(III)picolinate (abbreviation: FIrpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinium-N,C2'}iridium(III)picolinate (abbreviation: [Ir(CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyridinium-N,C2']iridium(III)acetylacetonate (abbreviation: FIr(acac)), etc., which have phenylpyridine derivatives having electron-withdrawing groups as ligands.
[0220] <<Phosphorescent substances (495nm and above and 590nm and below: green or yellow)>> Examples of phosphorescent substances that emit green or yellow light and have an emission spectrum with a peak wavelength of 495 nm to 590 nm include the following substances.
[0221] For example, tris(4-methyl-6-phenylpyrimidinyl)iridium(III) (abbreviation: [Ir(mppm)3]), tris(4-tert-butyl-6-phenylpyrimidinyl)iridium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonate)bis(6-methyl-4-phenylpyrimidinyl)iridium(III) (abbreviation: [Ir(mppm)2(acac)]), (acetylacetonate)bis(6-tert-butyl-4-phenylpyrimidinyl)iridium(III) (abbreviation: [Ir(tBuppm)2(acac)]), (acetylacetonate)bis(6-tert-butyl-4-phenylpyrimidinyl)iridium(III) (abbreviation: [Ir(tBuppm)2(acac)]), (acetylacetonate)bis[6-(2-norbornyl)-4-phenylpyrimidinyl]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]), (acetylacetonate)bis[5-methyl-6-(2-methylphenyl)-4-phenylpyrimidinyl]iridium(III) (abbreviation: [Ir(mpmppm)2( acac)]), (acetylacetonato)bis{4,6-dimethyl-2-[6-(2,6-dimethylphenyl)-4-pyrimidinyl-κN3]phenyl-κC}iridium(III) (abbreviated as [Ir(dmppm-dmp)2(acac)]), (acetylacetonato)bis(4,6-diphenylpyrimidinyl)iridium(III) (abbreviated as [Ir(dppm)2(acac)]), etc.; (acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazine)iridium(III) (abbreviated as [Ir(mppr-Me)2(acac)]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazine)iridium(III) (abbreviated as [Ir(mppr-iPr)2(acac)]), etc.; tri(2-phenylpyridinium-N,C 2’ )iridium(III) (abbreviation: [Ir(ppy)3]), bis(2-phenylpyridinium-N,C 2’ )iridium(III)acetylacetonate (abbreviated as [Ir(ppy)2(acac)]), bis(benzo[h]quinoline)iridium(III)acetylacetonate (abbreviated as [Ir(bzq)2(acac)]), tris(benzo[h]quinoline)iridium(III) (abbreviated as [Ir(bzq)3]), tris(2-phenylquinoline-N,C 2’ )iridium(III) (abbreviation: [Ir(pq)3]), bis(2-phenylquinoline-N,C 2’)iridium(III) acetylacetonate (abbreviation: [Ir(pq)2(acac)]), bis[2-(2-pyridyl-κN)phenyl-κC][2-(4-phenyl-2-pyridyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(ppy)2(4dppy)]), bis[2-(2-pyridyl-κN)phenyl-κC][2-(4-methyl-5-phenyl-2-pyridyl-κN)phenyl-κC], [2-d3-methyl-8-(2-pyridyl-κN)benzofuran[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridyl-κN 2 )phenyl-κC]iridium(III) (abbreviation: 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) (abbreviation: Ir(5mtpy-d6)2(mbfpypy-iPr-d4)), [2-d3-methyl Organometallic iridium complexes having a pyridine ring, such as [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)), ... 2’ ) iridium (III) acetylacetonate (abbreviated as [Ir(dpo)2(acac)]), bis{2-[4'-(perfluorophenyl)phenyl]pyridine-N,C 2’ Iridium(III) acetylacetonate (abbreviated as [Ir(p-PF-ph)2(acac)]), bis(2-phenylbenzothiazole-N,C 2’ ) organic metal complexes such as iridium (III) acetylacetonate (abbreviated as [Ir(bt)2(acac)]), and rare earth metal complexes such as tris(acetylacetonate)(monophenanthroline)terbium (III) (abbreviated as [Tb(acac)3(Phen)]).
[0222] <<Phosphorescent substances (570nm and above and 750nm and below: yellow or red)>> Examples of phosphorescent substances that exhibit yellow or red light and have an emission spectrum with a peak wavelength of 570 nm to 750 nm include the following substances.
[0223] For example, (diisobutyrylmethane)bis[4,6-bis(3-methylphenyl)pyrimidinyl]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinyl](dipivaloylmethane)iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)]), (dipivaloylmethane)bis[4,6-di(naphthalene-1-yl)pyrimidinyl]iridium(III) (abbreviation: [Ir(d1npm)2(dpm)]), etc. can be mentioned. Organic metal complexes with pyrimidine rings; (acetylacetonato)bis(2,3,5-triphenylpyrazine)iridium(III) (abbreviated as [Ir(tppr)2(acac)]), bis(2,3,5-triphenylpyrazine)(dipivaloylmethane)iridium(III) (abbreviated as [Ir(tppr)2(dpm)]), bis{4,6-dimethyl-2-[3-(3,5-dimethylphenyl)-5-phenyl-2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl-3,5-heptanedione-κ 2 O, O') iridium (III) (abbreviated as [Ir(dmdppr-P)2(dibm)]), bis{4,6-dimethyl-2-[5-(4-cyano-2,6-dimethylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,2,6,6-tetramethyl-3,5-heptanedione-κ 2 O, O') iridium (III) (abbreviation: [Ir(dmdppr-dmCP)2(dpm)]), bis{2-[5-(2,6-dimethylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN]-4,6-dimethylphenyl-κC}(2,2',6,6'-tetramethyl-3,5-heptanedione-κ2O, O') iridium (III) (abbreviation: [Ir(dmdppr-dmp)2(dpm)]), (acetylacetonato)bis(2-methyl-3-phenylquinoxalinato]-N,C 2’ )iridium(III) (abbreviation: [Ir(mpq)2(acac)]), (acetylacetonato)bis(2,3-diphenylquinoxalinato)-N,C 2’ ]iridium (III) (abbreviated as [Ir(dpq)2(acac)]), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium (III) (abbreviated as [Ir(Fdpq)2(acac)]) and other organic metal complexes having a pyrazine ring; tris(1-phenylisoquinoline-N,C 2’ )iridium(III) (abbreviated as [Ir(piq)3]), bis(1-phenylisoquinoline-N,C 2’)Iridium(III) acetylacetonate (abbreviation: [Ir(piq)2(acac)]) and bis[4,6-dimethyl-2-(quinolin-2-yl-κN)phenyl-κC](2,4-pentanedionato-κ 2 O,O’)iridium(III) (abbreviation: [Ir(dmpqn)2(acac)]) and other organometallic complexes having a pyridine ring; platinum complexes such as platinum(II) 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin (abbreviation: [PtOEP]); or rare earth metal complexes such as tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: [Eu(DBM)3(Phen)]) and tris[1-(2-thienoyl)-3,3,3-trifluoroacetone](monophenanthroline)europium(III) (abbreviation: [Eu(TTA)3(Phen)]).
[0224] <<TADF material>> In addition, as the TADF material, the following materials can be used. The TADF material refers to a material in which the energy difference between the S1 energy level and the T1 energy level is small (preferably 0.20 eV or less) and can convert the triplet excited state into the singlet excited state (reverse intersystem crossing) by using minute thermal energy and emit light (fluorescence) from the singlet excited state with high efficiency. The conditions for obtaining thermally activated delayed fluorescence with high efficiency are as follows: the energy difference between the triplet excited energy level and the singlet excited energy level is 0.00 eV or more and 0.20 eV or less, preferably 0.00 eV or more and 0.10 eV or less. The delayed fluorescence emitted by the TADF material refers to light emission having the same spectrum as ordinary fluorescence but a very long lifetime. Its lifetime is 1×10 -6 seconds or more or 1×10 -3 seconds or more.
[0225] In addition, the TADF material can be used as an electron transporting material, a hole transporting material, or a host material.
[0226] Examples of TADF materials include fullerene and its derivatives, acridine derivatives such as prussicin, eosin, etc. In addition, metal-containing porphyrins including magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd) can be cited. As metal-containing porphyrins, for example, protoporphyrin-tin fluoride complex (abbreviated as: SnF2(Proto IX)), mesoporphyrin-tin fluoride complex (abbreviated as: SnF2(Meso IX)), hematoporphyrin-tin fluoride complex (abbreviated as: SnF2(HematoIX)), coproporphyrin tetramethyl ester-tin fluoride complex (abbreviated as: SnF2(Copro III-4Me)), octaethylporphyrin-tin fluoride complex (abbreviated as: SnF2(OEP)), protoporphyrin-tin fluoride complex (abbreviated as: SnF2(Etio I)) and octaethylporphyrin-platinum chloride complex (abbreviated as: PtCl2OEP) can be mentioned.
[0227] [Chemical formula 21]
[0228] In addition to the above, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[2,3-a]carbazole-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ), 2-{4-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 2-[4-(1 0H-phenoxazine-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviated as PXZ-TRZ), 3-[4-(5-phenyl-5,10-dihydrophenazine-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (abbreviated as PPZ-3TPT), 3-(9,9-dimethyl-9H-acridin-10-yl)-9H-xanthene-9-one (abbreviated as ACRXTN), dimethoxybenzylamine [4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10'H-spiro[acridine-9,9'-anthracen]-10'-one (abbreviation: ACRSA), 4-(9'-phenyl-3,3'-bi-9H-carbazol-9-yl)benzofurano[3,2-d]pyrimidine (abbreviation: 4PCCzBfpm), 4-[4-(9'-phenyl -3,3'-biphenyl-9H-carbazole-9-yl)phenyl]benzofurano[3,2-d]pyrimidine (abbreviated as: 4PCCzPBfpm), 9-[3-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl]-9'-phenyl-2,3'-biphenyl-9H-carbazole (abbreviated as: mPCCzPTzn-02), and other heteroaromatic compounds having π-electron-rich heteroaromatic compounds and π-electron-deficient heteroaromatic compounds.
[0229] In addition, in the substance in which the π-electron-rich heteroaromatic compound and the π-electron-deficient heteroaromatic compound are directly bonded, the donor property of the π-electron-rich heteroaromatic compound and the acceptor property of the π-electron-deficient heteroaromatic compound are both strong, and the energy difference between the singlet excited state and the triplet excited state becomes small, so it is particularly preferred. In addition, as a TADF material, a TADF material (TADF100) in which the singlet excited state and the triplet excited state are in thermal equilibrium can also be used. This TADF material has a short luminescence lifetime (excitation lifetime), so it can suppress the efficiency reduction in the high brightness area of the light-emitting device.
[0230] [Chemical formula 22]
[0231] In addition to the above, as a material having the function of converting triplet excitation energy into luminescence, a nanostructure of a transition metal compound having a perovskite structure can be cited. Metal halide perovskite nanostructures are particularly preferred. As the nanostructure, nanoparticles and nanorods are preferred.
[0232] In the light-emitting layer (113, 113a, 113b), as an organic compound (host material, etc.) used in combination with the above-mentioned light-emitting substance (guest material), one or more substances having a larger energy gap than the light-emitting substance (guest material) can be used.
[0233] <<Fluorescent host material>> When the light-emitting material used for the light-emitting layer (113, 113a, 113b) is a fluorescent light-emitting material, as an organic compound (host material) used in combination with the light-emitting material, it is preferred to use an organic compound whose singlet excited state energy level is large and whose triplet excited state energy level is small or an organic compound with a high fluorescence quantum yield. Therefore, as long as the organic compound satisfies the above conditions, the hole transport material (described above) and the electron transport material (described later) shown in this embodiment can be used. In addition, the first organic compound can be used.
[0234] Although part of the content is repeated in the above specific examples, from the viewpoint of preferably using in combination with a light-emitting substance (fluorescent light-emitting substance), examples of the organic compound (host material) include anthracene derivatives, tetracene derivatives, phenanthrene derivatives, pyrene derivatives, (chrysene) derivatives, dibenzo[g,p] Derivatives and other fused polycyclic aromatic compounds.
[0235] Specific examples of organic compounds (host materials) preferably used in combination with fluorescent substances include 9-phenyl-3-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as PCzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as DPCzPA), 3-[4-(1-naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviated as PCPN), 9,10-diphenylanthracene (abbreviated as DPAnth), N,N-diphenyl-9-[4-( 10-phenyl-9-anthracenyl)phenyl]-9H-carbazole-3-amine (abbreviated as: CzA1PA), 4-(10-phenyl-9-anthracenyl)triphenylamine (abbreviated as: DPhPA), YGAPA, PCAPA, N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthracenyl)phenyl]phenyl}-9H-carbazole-3-amine (abbreviated as: PCAPBA), N-(9,10-diphenyl-2-anthracenyl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as: 2PCAPA), 6,12-dimethoxy-5,11-diphenyl N,N,N',N',N",N",N"',N"'-octaphenyldibenzo[g,p] -2,7,10,15-tetramine (abbreviation: DBC1), 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-[4-(9-phenyl-9H-fluoren-9-yl)biphenyl-4'-yl]anthracene (abbreviation: FLPPA), 9,10-bis(3,5-diphenylphenyl) anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9-(1-naphthyl)-10-(2-naphthyl)anthracene (abbreviation: α, β-ADN), 2-(10-phenylanthracen-9-yl)dibenzofuran, 2-(10-phenyl-9-anthracen-yl)-benzo[b]naphtho[2,3-d]furan (abbreviation: Bnf(II)PhA), 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth), 2,9-di(1-naphthyl)-10-phenylanthracene (abbreviation: α, β-ADN), 2-(10-phenylanthracen-9-yl)dibenzofuran, 2-(10-phenyl-9-anthracen-yl)-benzo[b]naphtho[2,3-d]furan (abbreviation: Bnf(II)PhA), 9-(2-naphthyl)-10-[4-(1-naphthyl)phenyl]anthracene (abbreviation: αN-αNPhA), 9-(1-naphthyl)-10-[3-(1-naphthyl)phenyl]anthracene (abbreviation: αN-mαNPAnth), 9-(2-naphthyl)-10-[3-(1-naphthyl)phenyl]anthracene (abbreviation: βN-mαNPAnth), 9-(1-naphthyl)-10-[4-(1-naphthyl)phenyl]anthracene (abbreviation: αN-αNPAnth), 9-(2-naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: βN-βNPAnth), 2-(1-naphthyl)-9-(2-naphthyl)-10-phenylanthracene (abbreviation: 2αN-βNPhA), 9-(2-naphthyl)-10-[3-(1-naphthyl)phenyl]anthracene (abbreviation: βN-mαNPAnth), )-10-[3-(2-naphthyl)phenyl]anthracene (abbreviation: βN-mβNPAnth), 1-{4-[10-(biphenyl-4-yl)-9-anthryl]phenyl}-2-ethyl-1H-benzimidazole (abbreviation: EtBImPBPhA), 9,9'-bianthracene (abbreviation: BANT), 9,9'-(stilbene-3,3'-diyl)phenanthrene (abbreviation: DPNS), 9,9'-(stilbene-4,4'-diyl)phenanthrene (abbreviation: DPNS2), 1,3,5-tri(1-pyrene)benzene (abbreviation: TPB3), 5,12-diphenyl tetracene, 5,12-bis(biphenyl-2-yl) tetracene, etc.
[0236] <<Phosphorescent host material>> When the light-emitting material used for the light-emitting layer (113, 113a, 113b) is a phosphorescent light-emitting material, as the organic compound (host material) used in combination with the light-emitting material, an organic compound whose triplet excitation energy (energy difference between the ground state and the triplet excited state) is greater than the triplet excitation energy of the light-emitting material can be selected. Note that when a plurality of organic compounds (for example, a first host material and a second host material (or an auxiliary material)) are used in combination with the light-emitting material in order to form an exciplex, it is preferable to use these plurality of organic compounds mixed with the phosphorescent light-emitting material. Alternatively, the first organic compound may be used.
[0237] By adopting such a structure, light emission by ExTET (Exciplex-Triplet Energy Transfer) utilizing energy transfer from an exciplex to a luminescent substance can be efficiently obtained. As a combination of multiple organic compounds, a combination that easily forms an exciplex is preferably used, and a combination of a compound that easily receives holes (hole transport material) and a compound that easily receives electrons (electron transport material) is particularly preferred.
[0238] Although part of the content is repeated in the above specific examples, from the viewpoint of the preferred combination with the light-emitting substance (phosphorescent light-emitting substance), examples of the organic compound (host material, auxiliary material) include aromatic amines (organic compounds having an aromatic amine skeleton), carbazole derivatives (organic compounds having a carbazole ring), dibenzothiophene derivatives (organic compounds having a dibenzothiophene ring), dibenzofuran derivatives (organic compounds having a dibenzofuran ring), oxadiazole derivatives (organic compounds having an oxadiazole ring), triazole derivatives (organic compounds having a triazole ring), benzimidazole derivatives (organic compounds having a dibenzofuran ring), and the like. Organisms (organic compounds having a benzimidazole ring), quinoxaline derivatives (organic compounds having a quinoxaline ring), dibenzoquinoxaline derivatives (organic compounds having a dibenzoquinoxaline ring), pyrimidine derivatives (organic compounds having a pyrimidine ring), triazine derivatives (organic compounds having a triazine ring), pyridine derivatives (organic compounds having a pyridine ring), bipyridine derivatives (organic compounds having a bipyridine ring), phenanthroline derivatives (organic compounds having a phenanthroline ring), furanodiazine derivatives (organic compounds having a furanodiazine ring), zinc and aluminum metal complexes, etc.
[0239] Note that among the above organic compounds, specific examples of aromatic amines and carbazole derivatives as organic compounds having a high hole-transporting property include the same materials as the specific examples of the hole-transporting materials described above, and these materials are preferably used as the host material.
[0240] Specific examples of dibenzothiophene derivatives and dibenzofuran derivatives as organic compounds having high hole transport properties among the above organic compounds include 4-{3-[3-(9-phenyl-9H-fluorene-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II), 4,4',4"-(benzene-1,3,5-triyl)tris(dibenzofuran) (abbreviation: DBF3P-II), DBT3P-II, and II, 2,8-diphenyl-4-[4-(9-phenyl-9H-fluorene-9-yl)phenyl]dibenzothiophene (abbreviated as: DBTFLP-III), 4-[4-(9-phenyl-9H-fluorene-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviated as: DBTFLP-IV), 4-[3-(triphenyl-2-yl)phenyl]dibenzothiophene (abbreviated as: mDBTPTp-II), etc. These materials are preferably used as the main materials.
[0241] In addition, preferred host materials include metal complexes having oxazolyl ligands and thiazole ligands, such as bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviated as ZnPBO) and bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviated as ZnBTZ).
[0242] In addition, among the above-mentioned organic compounds, specific examples of oxadiazole derivatives, triazole derivatives, benzimidazole derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, quinazoline derivatives, phenanthroline derivatives, etc., which are organic compounds with high electron transport properties, include 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), oxadiazole-2-yl)phenyl]-9H-carbazole (abbreviated as CO11), 3-(4-biphenyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviated as TAZ), 2,2',2"-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviated as TPBI), 2-[3-(dibenzothiophene-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviated as mDBTBIm-II), 4,4'-bis(5-methylbenzothiophene-2-yl)phenylethylene (abbreviated as BzO S) and the like, organic compounds containing heteroaromatic rings having azole rings, bathophenanthroline (abbreviation: Bphen), bathocuproine (abbreviation: BCP), 2,9-di(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen), 2,2'-(1,3-phenylene)bis(9-phenyl-1,10-phenanthroline) (abbreviation: mPPhen2P) and the like, 2-[3-(dibenzothiophene-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviated as: 2mDBTPDBq-II), 2-[3'-(dibenzothiophene-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviated as: 2mDBTBPDBq-II), 2-[3'-(9H-carbazole-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviated as: 2mCzBPDB q), 2-[4-(3,6-diphenyl-9H-carbazole-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviated as: 2CzPDBq-III), 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviated as: 7mDBTPDBq-II) and 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviated as: 6mDBTPDBq-I I), 2-{4-[9,10-di(2-naphthyl)-2-anthracenyl]phenyl}-1-phenyl-1H-benzimidazole (abbreviation: ZADN), 2-[4'-(9-phenyl-9H-carbazole-3-yl)-3,1'-biphenyl-1-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mpPCBPDBq) organic compounds containing heteroaromatic rings having dibenzoquinoxaline rings, etc., these materials are preferably used as the main material.
[0243] Among the above-mentioned organic compounds, specific examples of pyridine derivatives, diazine derivatives (including pyrimidine derivatives, pyrazine derivatives, and pyridazine derivatives), triazine derivatives, and furanodiazine derivatives as organic compounds with high electron transport properties include 4,6-bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazole-9-yl)phenyl]pyrimidine) (abbreviation: 4,6mCzP2Pm), 2-{4-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-9-yl]phenyl} -4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 9-[3-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl]-9'-phenyl-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn-02), 3,5-bis[3-(9H-carbazole-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tris[3-(3-pyridine)phenyl]benzene (abbreviation: TmPyPB), 9,9'-[pyrimidine-4,6-diylbis(biphenyl-3,3'-diyl)]bis(9H-carbazole) (abbreviation: 4,6mCzBP2Pm), 2-[3'-(9,9-dimethyl-9H 1-[(3'-(dibenzothiophene-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated as 9mDBtBPNfpr), 9-[(3'-(dibenzothiophene-4-yl)biphenyl-4-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated as 9pm ... PNfpr), 11-[(3'-(dibenzothiophene-4-yl)biphenyl-3-yl]phenanthro[9',10':4,5]furo[2,3-b]pyrazine (abbreviated as: 11mDBtBPPnfpr), 11-[3'-(dibenzothiophene-4-yl)biphenyl-4-yl]phenanthro[9',10':4,5]furo[2,3-b]pyrazine, 11-[3'-(9H-carbazole-9-yl)biphenyl-3-yl]phenanthro[9',10':4,5]furo[2,3-b]pyrazine, 12-(9'-phenyl-3,3'-bi-9H-carbazole-9-yl)phenanthro[9',10':4,5]furo[2,3-b]pyrazine (abbreviated as: 12PCCzPnfpr), 9-[(3'-9-phenyl-9H-carbazole-3-yl)biphenyl-4-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated as: 9pmPCBPNfpr), 9-(9'-phenyl-3,3'-bi-9H-carbazole-9-yl)naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated as: 9PCCzNfpr), 10-(9'-phenyl-3,3'-bi-9H-carbazole-9-yl)naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviated as: 10PCCzNfpr), 9-[3'-(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl) [1', 2': 4, 5] furano[2, 3-b] pyrazine (abbreviation: 9mBnfBPNfpr), 9-{3-[6-(9,9-dimethylfluoren-2-yl)dibenzothiophen-4-yl]phenyl}naphtho[1', 2': 4, 5] furano[2, 3-b] pyrazine (abbreviation: 9mFDBtPNfpr), 9-[3'-(6-phenyldibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1', 2': 4, 5] furano[2, 3-b] pyrazine (abbreviation: 9mDBtBPNfpr-02), 9-[3-(9'-phenyl-3, 3'-bi-9H-carbazole-9-yl)phenyl]naphtho[1', 2': 4, 5] furano[2, 3-b]pyrazine (abbreviated as 9mPCCzPNfpr), 9-[3'-(2,8-diphenyldibenzothiophene-4-yl)biphenyl-3-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine, 11-{(3'-[2,8-diphenyldibenzothiophene-4-yl]biphenyl-3-yl}phenanthro[9',10':4,5]furo[2,3-b]pyrazine, 5-[3-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl]-7,7-dimethyl-5H,7H-indeno[2,1-b]carbazole (abbreviated as mINc(II)PTzn), 2-[3'-(triphenylene-2-yl)biphenyl-3-yl]-4,6-diphenyl-1,3,5 -triazine (abbreviation: mTpBPTzn), 2-(biphenyl-4-yl)-4-phenyl-6-(9,9'-spirobi[9H-fluorene]-2-yl)-1,3,5-triazine (abbreviation: BP-SFTzn), 2,6-bis(4-naphth-1-ylphenyl)-4-[4-(3-pyridyl)phenyl]pyrimidine (abbreviation: 2,4NP-6PyPPm), 3-[9-(4,6-diphenyl-1,3,5-triazine-2-yl)-2-dibenzofuranyl]-9-phenyl-9H-carbazole (abbreviation: PCDBfTzn), 2-(biphenyl-3-yl)-4-phenyl-6-{8-[(1,1':4',1"-terphenyl)-4-yl]-1-dibenzofuranyl}-1,3,Organic compounds containing heteroaromatic rings having diazine rings, such as 5-triazine (abbreviation: mBP-TPDBfTzn), 6-(biphenyl-3-yl)-4-[3,5-bis(9H-carbazole-9-yl)phenyl]-2-phenylpyrimidine (abbreviation: 6mBP-4Cz2PPm), and 4-[3,5-bis(9H-carbazole-9-yl)phenyl]-2-phenyl-6-(biphenyl-4-yl)pyrimidine (abbreviation: 6BP-4Cz2PPm), are preferably used as the host material.
[0244] Among the above-mentioned organic compounds, specific examples of metal complexes of organic compounds with high electron transport properties include: zinc or aluminum metal complexes of tris(8-hydroxyquinoline)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-hydroxyquinoline)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviation: BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviation: Znq); metal complexes having a quinoline ring or a benzoquinoline ring, etc. These materials are preferably used as the main material.
[0245] In addition, as preferred main materials, polymer compounds such as poly(2,5-pyridinediyl) (abbreviated as PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py), and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy) can also be used.
[0246] Furthermore, bipolar 9-phenyl-9'-(4-phenyl-2-quinazolinyl)-3,3'-bi-9H-carbazole (abbreviation: PCCzQz), 2-[4'-(9-phenyl-9H-carbazole-3-yl)-3,1'-biphenyl-1-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mpPCBPDBq), 5-[3-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl]-7,7-dimethyl-5H,7H-indole, which are organic compounds with high hole transport properties and high electron transport properties, Organic compounds having a dioxazine ring, such as indole[2,1-b]carbazole (abbreviation: mINc(II)PTzn), 11-[4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine-2-yl]-11,12-dihydro-12-phenyl-indole[2,3-a]carbazole (abbreviation: BP-Icz(II)Tzn), and 7-[4-(9-phenyl-9H-carbazole-2-yl)quinazoline-2-yl]-7H-dibenzo[c,g]carbazole (abbreviation: PC-cgDBCzQz), can also be used as the main material.
[0247] <Electron Transport Layer> The electron transport layer (114, 114a, 114b) is a layer that transports electrons injected from the second electrode 102 and the charge generation layer (106, 106a, 106b) by the electron injection layer (115, 115a, 115b) described later to the light-emitting layer (113, 113a, 113b). In addition, the light-emitting device of one embodiment of the present invention has improved heat resistance because the electron transport layer has a stacked structure. The electron transport material used for the electron transport layer (114, 114a, 114b) preferably has a 1×10 -6 cm 2 / Vs or more. In addition, as long as the electron transport property is higher than the hole transport property, substances other than the above can be used. In addition, the electron transport layer (114, 114a, 114b) works even if it is a single layer, but a stacked structure of more than two layers can also be used. Note that since the above-mentioned mixed material is heat-resistant, by performing a photolithography process on the electron transport layer using the mixed material, the influence of the thermal process on the device characteristics can be suppressed.
[0248] <<Electron Transport Materials>> As an electron transport material that can be used for the electron transport layer (114, 114a, 114b), an organic compound with high electron transport properties can be used, for example, a heteroaromatic compound can be used. Note that a heteroaromatic compound refers to a cyclic compound containing at least two different elements in the ring. Note that as a ring structure, a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, etc. are included, and a five-membered ring or a six-membered ring is particularly preferred. As the element contained in the heteroaromatic compound, in addition to carbon, it is preferably any one or more of nitrogen, oxygen and sulfur. Particularly preferred is a heteroaromatic compound containing nitrogen (nitrogen-containing heteroaromatic compound), and it is preferred to use a nitrogen-containing heteroaromatic compound or a π-electron-deficient heteroaromatic compound containing the nitrogen-containing heteroaromatic compound. High electron transport materials (electron transport materials) such as π-electron-deficient heteroaromatic compounds are preferably used.
[0249] Note that the electron transport material may use a material different from the material used for the light-emitting layer. Not all excitons generated by the recombination of carriers in the light-emitting layer may contribute to luminescence, and sometimes diffuse to the layer in contact with the light-emitting layer or in the vicinity thereof. In order to avoid this phenomenon, the energy level (lowest singlet excitation level or lowest triplet excitation level) of the material used for the layer in contact with the light-emitting layer or in the vicinity thereof is preferably higher than that of the material used for the light-emitting layer. Thus, when a material different from the material used for the light-emitting layer is used for the electron transport material, a highly efficient device can be obtained.
[0250] Heteroaromatic compounds are organic compounds having at least one heteroaromatic ring.
[0251] Note that the heteroaromatic ring has any one of a pyridine ring, a diazine ring, a triazine ring, a polyazole ring, an oxazole ring, a thiazole ring, etc. Further, the heteroaromatic ring having a diazine ring includes a heteroaromatic ring having a pyrimidine ring, a pyrazine ring, or a pyridazine ring, etc. Further, the heteroaromatic ring having a polyazole ring includes a heteroaromatic ring having an imidazole ring, a triazole ring, or an oxadiazole ring.
[0252] The heteroaromatic ring includes a condensed heteroaromatic ring having a condensed ring structure. Note that examples of the condensed heteroaromatic ring include a quinoline ring, a benzoquinoline ring, a quinoxaline ring, a dibenzoquinoxaline ring, a quinazoline ring, a benzoquinazoline ring, a dibenzoquinazoline ring, a phenanthroline ring, a furadiazine ring, and a benzimidazole ring.
[0253] Note that, for example, among heteroaromatic compounds containing any one or more of nitrogen, oxygen, sulfur, etc. in addition to carbon, as heteroaromatic compounds having a five-membered ring structure, there can be mentioned heteroaromatic compounds having an imidazole ring, heteroaromatic compounds having a triazole ring, heteroaromatic compounds having an oxazole ring, heteroaromatic compounds having an oxadiazole ring, heteroaromatic compounds having a thiazole ring, heteroaromatic compounds having a benzimidazole ring, and the like.
[0254] For example, among heteroaromatic compounds containing any one or more of nitrogen, oxygen, sulfur, etc. in addition to carbon, as heteroaromatic compounds having a six-membered ring structure, there can be mentioned heteroaromatic compounds having heteroaromatic rings such as pyridine rings, diazine rings (including pyrimidine rings, pyrazine rings, pyridazine rings, etc.), triazine rings, and azole rings. Note that heteroaromatic compounds having a bipyridine structure, heteroaromatic compounds having a terpyridine structure, etc. can be mentioned, and they are included in the examples of heteroaromatic compounds connected to a pyridine ring.
[0255] Furthermore, examples of heteroaromatic compounds having a fused ring structure in which a portion of the six-membered ring structure is included include heteroaromatic compounds having fused heteroaromatic rings such as a quinoline ring, a benzoquinoline ring, a quinoxaline ring, a dibenzoquinoxaline ring, a phenanthroline ring, a furanodiazine ring (including a structure in which a furan ring of a furanodiazine ring is fused with an aromatic ring), and a benzimidazole ring.
[0256] Specific examples of heteroaromatic compounds having the above-mentioned five-membered ring structure (azole ring (including imidazole ring, triazole ring, oxadiazole ring), oxazole ring, thiazole ring, benzimidazole ring, etc.) include 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazole-2-yl)phenyl]-9H-carbazole (abbreviation: CO11), 3-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazole-2-yl)phenyl]-9H-carbazole (abbreviation: CO11), (4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (abbreviation: p-EtTAZ), 2,2',2"-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophene-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs), etc.
[0257] Specific examples of heteroaromatic compounds having the above-mentioned six-membered ring structure (including heteroaromatic rings having pyridine rings, diazine rings, triazine rings, etc.) include 3,5-bis[3-(9H-carbazole-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tris[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), and the like, which are heteroaromatic compounds containing heteroaromatic rings having pyridine rings; 2-{4-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-9-yl]phenyl}-4,6-diphenyl -1,3,5-triazine (abbreviation: PCCzPTzn), 9-[3-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl]-9'-phenyl-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn-02), 5-[3-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl]-7,7-dimethyl-5H,7H-indeno[2,1-b]carbazole (abbreviation: mINc(II)PTzn), 2-[3'-(triphenylene-2-yl)biphenyl-3-yl] ]-4,6-diphenyl-1,3,5-triazine (abbreviated as mTpBPTzn), 2-(biphenyl-4-yl)-4-phenyl-6-(9,9'-spirobi[9H-fluorene]-2-yl)-1,3,5-triazine (abbreviated as BP-SFTzn), 2,6-bis(4-naphthylphenyl)-4-[4-(3-pyridyl)phenyl]pyrimidine (abbreviated as 2,4NP-6PyPPm), 3-[9-(4,6-diphenyl-1,3,5-triazine-2-yl)-2-dibenzofuranyl]-9-phenyl Heteroaromatic compounds containing a heteroaromatic ring having a triazine ring, such as 2-(biphenyl-3-yl)-4-phenyl-6-{8-[(1,1':4',1"-terphenyl)-4-yl]-1-dibenzofuranyl}-1,3,5-triazine (abbreviated as mBP-TPDBfTzn), 2-{3-[3-(dibenzothiophen-4-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviated as mDBtBPTzn), and mFBPTzn;4,6-bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazole-9-yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), 4,6mCzBP2Pm, 6-(biphenyl-3-yl)-4-[3,5-bis(9H-carbazole-9 -yl)phenyl]-2-phenylpyrimidine (abbreviation: 6mBP-4Cz2PPm), 4-[3,5-bis(9H-carbazol-9-yl)phenyl]-2-phenyl-6-(biphenyl-4-yl)pyrimidine (abbreviation: 6BP-4Cz2PPm), 4-[3-(dibenzothiophen-4-yl)phenyl]-8-(naphthalen-2-yl)-[1]benzofurano[3,2-d]pyrimidine (abbreviation: 8βN-4mDBtPBfpm), 8BP- 4mDBtPBfpm, 9mDBtBPNfpr, 9pmDBtBPNfpr, 3,8-bis[3-(dibenzothiophen-4-yl)phenyl]benzofurano[2,3-b]pyrazine (abbreviated as 3,8mDBtP2Bfpr), 4,8-bis[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofurano[3,2-d]pyrimidine (abbreviated as 4,8mDBtP2Bfpm), 8-[3'-(dibenzothiophen-4-yl)phenyl]-[1]benzofurano[3,2-d]pyrimidine Heteroaromatic compounds containing a heteroaromatic ring having a diazine (pyrimidine) ring, such as 8-[(2,2'-binaphthyl)-6-yl]-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofurano[3,2-d]pyrimidine (abbreviation: 8(βN2)-4mDBtPBfpm). ;
[0258] In addition, 2,2'-(pyridine-2,6-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviation: 2,6(P-Bqn)2Py), 2,2'-(2,2'-bipyridine-6,6'-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviation: 6,6'(P-Bqn)2BPy), 2,2'-(pyridine-2,6-diyl)bis{4-[4-(2-naphthyl)phenyl]-6-phenylpyrimidine} (abbreviation: 2,6(NP-PPm)2Py), 6-(biphenyl-3-yl)-4-[3,5-bis(9H-carbazole-9-yl)phenyl]-2-phenyl Heteroaromatic compounds containing heteroaromatic rings having diazine (pyrimidine) rings, such as pyrimidine (abbreviation: 6mBP-4Cz2PPm); heteroaromatic compounds containing heteroaromatic rings having triazine rings, such as 2,4,6-tris[3'-(pyridin-3-yl)biphenyl-3-yl]-1,3,5-triazine (abbreviation: TmPPPyTz), 2,4,6-tris(2-pyridinyl)-1,3,5-triazine (abbreviation: 2Py3Tz), 2-[3-(2,6-dimethyl-3-pyridinyl)-5-(9-phenanthrenyl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mPn-mDMePyPTzn), etc.
[0259] Specific examples of heteroaromatic compounds having a fused ring structure in which a part of the heteroaromatic compounds includes the above-mentioned six-membered ring structure (heteroaromatic compounds having a fused ring structure) include bathophenanthroline (abbreviation: Bphen), bathocuproin (abbreviation: BCP), 2,9-di(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen), 2,2'-(1,3-phenylene)bis(9-phenyl-1,10-phenanthroline) (abbreviation: mPPhen2P), 2,2'-(pyridine-2,6-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviation: 2,6(P-Bqn)2Py), 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(diphenylene)bis(4-phenylene)bis(f,h]quinazoline) (abbreviation: 2mDBTPDBq-II), heteroaromatic compounds having a quinoxaline ring, such as 2-[3-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 2-[4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPDBq-II), 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II), and 2mpPCBPDBq.
[0260] In addition to the above-mentioned heteroaromatic compounds, the following metal complexes can be used for the electron transport layer (114, 114a, 114b). Examples of the metal complexes include tris(8-hydroxyquinoline)aluminum(III) (abbreviated as Alq3), Almq3, 8-hydroxyquinoline lithium (abbreviated as Liq), BeBq2, bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviated as BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviated as Znq), and metal complexes having a quinoline ring or a benzoquinoline ring, and bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviated as ZnPBO), bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviated as ZnBTZ), and the like.
[0261] In addition, as electron transport materials, polymer compounds such as poly(2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy) can also be used.
[0262] In addition, the electron transport layer (114, 114a, 114b) may be a single layer or a stack of two or more layers containing the above-mentioned substances.
[0263] <Electron Injection Layer> The electron injection layer (115, 115a, 115b) is a layer containing a substance with high electron injection property. The electron injection layer (115, 115a, 115b) is a layer used to improve the efficiency of injecting electrons from the second electrode 102. It is preferred to use a material with a small difference (less than 0.50 eV) between the work function value of the material used for the second electrode 102 and the LUMO energy level value of the material used for the electron injection layer (115, 115a, 115b). Therefore, as the electron injection layer 115, lithium, cesium, lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), 8-hydroxyquinoline-lithium (abbreviated as: Liq), 2-(2-pyridyl) phenol lithium (abbreviated as: LiPP), 2-(2-pyridyl)-3-hydroxypyridine (pyridinolato) lithium (abbreviated as: LiPPy), 4-phenyl-2-(2-pyridyl) phenol lithium (abbreviated as: LiPPP), lithium oxide (LiO x), alkali metals such as cesium carbonate, alkaline earth metals or their compounds. In addition, rare earth metals such as erbium fluoride (ErF3) and ytterbium (Yb) or rare earth metal compounds can be used. In addition, compounds having a 1,3,4,6,7,8-tetrahydro-2H-pyrimido[1,2-a]pyrimidine skeleton, such as 1-(9,9'-spirobi[9H-fluorene]-2-yl)-1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (abbreviation: 2hppSF), 1,1'-(9,9'-spirobi[9H-fluorene]-2,7-diyl)bis(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine) (abbreviation: 2,7hpp2SF), and 1,1'-pyridine-2,6-diyl-bis(1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine) (abbreviation: hpp2Py), can also be used. Note that the electron injection layer (115, 115a, 115b) may be formed by mixing multiple materials mentioned above or by stacking multiple materials mentioned above. In addition, an electron compound may be used for the electron injection layer (115, 115a, 115b). As an example of the electron compound, a substance in which electrons are added to a mixed oxide of calcium and aluminum at a high concentration may be cited. In addition, the substance constituting the electron transport layer (114, 114a, 114b) as described above may also be used.
[0264] In addition, a mixed material formed by mixing an organic compound with an electron donor (donor) can also be used for the electron injection layer (115, 115a, 115b). This mixed material has excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material with excellent performance in transporting the generated electrons. Specifically, for example, an electron transport material (metal complex and heteroaromatic compound, etc.) used for the electron transport layer (114, 114a, 114b) as described above can be used. As an electron donor, a substance that exhibits electron donating properties to the organic compound can be used. Specifically, alkali metals, alkaline earth metals and rare earth metals are preferably used, and lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. can be mentioned. In addition, alkali metal oxides and alkaline earth metal oxides are preferably used, and lithium oxide, calcium oxide, barium oxide, etc. can be mentioned. In addition, Lewis bases such as magnesium oxide can also be used. In addition, organic compounds such as tetrathiafulvalene (abbreviated as: TTF) can also be used. Alternatively, multiple of these materials can be stacked and used.
[0265] In addition, a mixed material of an organic compound and a metal may be used for the electron injection layer (115, 115a, 115b). Note that the organic compound used here preferably has a LUMO level of -3.60 eV or more and -2.30 eV or less. In addition, a material having a non-shared electron pair is preferably used.
[0266] Therefore, as an organic compound for the above-mentioned mixed material, a mixed material formed by mixing the above-mentioned heteroaromatic compounds and metals that can be used for the electron transport layer can also be used. The heteroaromatic compound is preferably a heteroaromatic compound having a five-membered ring structure (imidazole ring, triazole ring, oxazole ring, oxadiazole ring, thiazole ring, benzimidazole ring, etc.), a heteroaromatic compound having a six-membered ring structure (pyridine ring, diazine ring (including pyrimidine ring, pyrazine ring, pyridazine ring, etc.), a triazine ring, a bipyridine ring, a terpyridine ring, etc.), a heteroaromatic compound having a condensed ring structure (quinoline ring, benzoxaline ring, quinoxaline ring, dibenzoquinoxaline ring, phenanthroline ring, etc.) having a six-membered ring structure, and the like. Materials with non-shared electron pairs. The specific materials have been described above, so their description is omitted here.
[0267] As the metal used for the mixed material, it is preferred to use transition metals belonging to Group 5, Group 7, Group 9 or Group 11 in the periodic table and materials belonging to Group 13, for example, Ag, Cu, Al or In. In addition, at this time, a single occupied orbital (SOMO) is formed between the organic compound and the transition metal.
[0268] In addition, for example, in the case of amplifying the light obtained from the light-emitting layer 113b, it is preferable to form the second electrode 102 and the light-emitting layer 113b in such a manner that the optical distance between the second electrode 102 and the light-emitting layer 113b is less than 1 / 4 of the wavelength λ of the light presented by the light-emitting layer 113b. In this case, the optical distance can be adjusted by changing the thickness of the electron transport layer 114b or the electron injection layer 115b.
[0269] In addition, if Figure 1E As in the light-emitting device shown in the figure, by providing two EL layers (103a, 103b) and providing the charge generation layer 106 between the two EL layers, a structure (also called a tandem structure) in which a plurality of EL layers are stacked between a pair of electrodes can be provided.
[0270] <Charge Generation Layer> The charge generation layer 106 has the following function: when a voltage is applied between the first electrode 101 (anode) and the second electrode 102 (cathode), electrons are injected into the EL layer 103a and holes are injected into the EL layer 103b. The charge generation layer 106 can have a structure in which an electron acceptor (acceptor) is added to a hole transport material (also called a P-type layer), and can also have a structure in which an electron donor (donor) is added to an electron transport material (also called an electron injection buffer layer). Alternatively, these two structures can be stacked. Furthermore, an electron relay layer can be provided between the P-type layer and the electron injection buffer layer. Note that by using the above-mentioned materials to form the charge generation layer 106, the increase in driving voltage caused by stacking EL layers can be suppressed.
[0271] In the case where the charge generation layer 106 has a structure in which an electron acceptor is added to a hole transport material of an organic compound (P-type layer), the material shown in this embodiment can be used as a hole transport material. In addition, as an electron acceptor, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviated as: F4-TCNQ), chloranil, etc. can be cited. In addition, oxides of metals belonging to Groups 4 to 8 in the periodic table can be cited. Specifically, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, rhenium oxide, etc. can be cited. In addition, the above-mentioned acceptor materials can also be used. In addition, a mixed film in which the materials constituting the P-type layer are mixed can be used, or a single film containing each material can be stacked.
[0272] In the case where the charge generation layer 106 has a structure in which an electron donor is added to an electron transport material (electron injection buffer layer), the material shown in this embodiment can be used as an electron transport material. In addition, as an electron donor, an alkali metal, an alkaline earth metal, a rare earth metal, or a metal belonging to Group 2 or Group 13 in the periodic table and their oxides or carbonates can be used. Specifically, lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), ytterbium (Yb), indium (In), lithium oxide (Li2O), cesium carbonate, etc. are preferably used. In addition, compounds of alkali metals such as Liq can also be used. In addition, organic compounds such as tetrathianaphthacene can also be used as electron donors. In addition, organic compounds having a 1,3,4,6,7,8-tetrahydro-2H-pyrimido[1,2-a]pyrimidine skeleton such as 2hppSF, 2,7hpp2SF, hpp2Py, etc. can also be used as electron donors. When these organic compounds are used as electron donors, when organic compounds containing heteroaromatic rings having phenanthroline rings such as bathophenanthroline (abbreviation: Bphen), bathocuproine (abbreviation: BCP), 2,9-di(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen), 2,2'-(1,3-phenylene)bis(9-phenyl-1,10-phenanthroline) (abbreviation: mPPhen2P) are used as combined electron transport materials, the driving voltage of the light-emitting device can be reduced, so it is preferred.
[0273] 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 contains at least a substance having electron transport properties, and has the function of preventing the interaction between the electron injection buffer layer and the P-type layer and smoothly transferring electrons. The LUMO energy level of the substance having electron transport properties contained in the electron relay layer is preferably located between the LUMO energy level of the acceptor substance in the P-type layer and the LUMO energy level of the substance having electron transport properties contained in the electron transport layer in contact with the charge generation layer 106. The specific value of the LUMO energy level of the substance having electron transport properties in the electron relay layer is preferably above -5.00 eV, more preferably above -5.00 eV and below -3.00 eV. In addition, as the substance having electron transport properties in the electron relay layer, it is preferred to use a phthalocyanine material or a metal complex having a metal-oxygen bond and an aromatic ligand.
[0274] In terms of light extraction efficiency, the charge generation layer 106 preferably has a light transmittance to visible light (specifically, the charge generation layer 106 has a visible light transmittance of 40% or more). The charge generation layer 106 can function even if its conductivity is lower than that of the first electrode 101 and the second electrode 102 .
[0275] Although Figure 1E Although a structure in which two EL layers 103 are stacked is shown, a structure in which three or more EL layers are stacked can be employed by providing a charge generating layer between different EL layers.
[0276] <Cap layer> Note that although Figures 1A to 1F Although not shown in the figure, a cap layer may be provided on the second electrode 102 of the light emitting device. For example, a material with a high refractive index may be used for the cap layer. By providing the cap layer on the second electrode 102, the extraction efficiency of light emitted from the second electrode 102 may be improved.
[0277] Specific examples of materials that can be used for the cap layer include 5,5'-diphenyl-2,2'-di-5H-[1]benzothieno[3,2-c]carbazole (abbreviated as BisBTc), 4,4',4"-(benzene-1,3,5-triyl)tris(dibenzothiophene) (abbreviated as DBT3P-II), and the like.
[0278] <Substrate> The light-emitting device shown in this embodiment can be formed on various substrates. Note that there is no particular limitation on the type of substrate. Examples of the substrate include a semiconductor substrate (e.g., a single crystal substrate or a silicon substrate), an SOI substrate, a glass substrate, a quartz substrate, a plastic substrate, a metal substrate, a stainless steel substrate, a substrate including a stainless steel foil, a tungsten substrate, a substrate including a tungsten foil, a flexible substrate, a laminated film, a paper including a fibrous material, or a substrate film.
[0279] Examples of glass substrates include barium borosilicate glass, aluminoborosilicate glass, and soda-lime glass. Examples of flexible substrates, laminated films, and base films include plastics represented by polyethylene terephthalate (PET), polyethylene naphthalate (PEN), and polyethersulfone (PES), synthetic resins such as acrylic resins, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyamide, polyimide, aramid, epoxy resins, inorganic vapor-deposited films, and paper.
[0280] In addition, when manufacturing the light-emitting device shown in this embodiment, a vapor phase method such as evaporation, a liquid phase method such as spin coating and inkjet can be used. As an evaporation method, a physical evaporation method (PVD method) such as sputtering, ion plating, ion beam evaporation, molecular beam evaporation, vacuum evaporation or chemical vapor deposition evaporation (CVD method) can be used. In particular, a layer with various functions (hole injection layer 111, hole transport layer 112, light-emitting layer 113, electron transport layer 114, electron injection layer 115) included in the EL layer of the light-emitting device can be formed by evaporation (vacuum evaporation), coating (dip coating, dye coating, rod coating, spin coating, spray coating, etc.), printing (inkjet, screen printing (porcelain printing), offset printing (lithography), flexographic printing (letterpress printing), gravure printing, micro-contact printing, etc.) and the like.
[0281] Note that when using the above-mentioned coating method, printing method or other film forming method, high molecular weight compounds (oligomers, dendrimers, polymers, etc.), medium molecular weight compounds (compounds between low molecular weight and high molecular weight: molecular weight of 400 to 4000), inorganic compounds (quantum dot materials, etc.) can be used. Note that as quantum dot materials, colloidal quantum dot materials, alloy quantum dot materials, core-shell quantum dot materials, core-type quantum dot materials, etc. can be used.
[0282] The materials of each layer (hole injection layer 111, hole transport layer 112, light-emitting layer 113, electron transport layer 114, electron injection layer 115) constituting the EL layer 103 of the light-emitting device shown in this embodiment are not limited to the materials shown in this embodiment, and any material that can satisfy the functions of each layer can be used in combination.
[0283] The structure described in this embodiment can be used in combination with the structure described in other embodiment modes as appropriate.
[0284] Implementation 3 In this embodiment, in order to explain a specific structural example of a light-emitting device as one embodiment of the present invention and an example of a manufacturing method thereof, a light-receiving and light-emitting device 700 is described. The light-receiving and light-emitting device 700 is a device including both a light-emitting device and a light-receiving device and can be called a light-emitting device including a light-receiving device or a light-receiving device including a light-emitting device. In addition, since the light-receiving and light-emitting device 700 can be applied to a display unit of an electronic device, etc., it can be called a display panel or a display device.
[0285] <Configuration Example of Light Receiving and Light Emitting Device 700> Figure 3A The light-emitting device 700 shown includes a light-emitting device 550B, a light-emitting device 550G, a light-emitting device 550R, and a light-receiving device 550PS formed on a functional layer 520 provided on a first substrate 510. The functional layer 520 includes not only a driving circuit such as a gate driver and a source driver composed of a plurality of transistors, but also wiring that electrically connects them. These driving circuits are electrically connected to the light-emitting device 550B, the light-emitting device 550G, the light-emitting device 550R, and the light-receiving device 550PS, respectively, and can drive these devices. In addition, the light-emitting device 700 includes an insulating layer 705 on the functional layer 520 and each device (the light-emitting device and the light-receiving device), and the insulating layer 705 has the function of bonding the second substrate 770 and the functional layer 520.
[0286] At least one of the light-emitting device 550B, the light-emitting device 550G, and the light-emitting device 550R has the device structure described in the above embodiment. Figure 1A ) differs between light-emitting devices. For example, the light-emitting layer 105B included in the EL layer 103B may emit blue light, the light-emitting layer 105G included in the EL layer 103G may emit green light, and the light-emitting layer 105R included in the EL layer 103R may emit red light. For example, the light-emitting layer 105B may have the structure of the light-emitting layer described in the above embodiment, and known materials may be used as the light-emitting layer 105G and the light-emitting layer 105R.
[0287] Note that this embodiment shows a case where each device (a plurality of light-emitting devices and a plurality of light-receiving devices) is formed separately, but in the manufacturing process, the same material can also be used to simultaneously form a portion of the EL layer of the light-emitting device (a hole injection layer, a hole transport layer, and an electron transport layer) and a portion of the active layer of the light-receiving device (a hole injection layer, a hole transport layer, and an electron transport layer).
[0288] In this specification, etc., a structure in which the light-emitting layer of each color light-emitting device (e.g., blue (B), green (G), and red (R)) and the light-receiving layer of the light-receiving device are formed or coated separately is sometimes referred to as an SBS (Side By Side) structure. Figure 3A In the light receiving and emitting device 700 shown, the light emitting device 550B, the light emitting device 550G, the light emitting device 550R, and the light receiving device 550PS are arranged in this order, but one embodiment of the present invention is not limited to this structure.
[0289] exist Figure 3A In the embodiment, the light emitting device 550B includes an electrode 551B, an electrode 552, and an EL layer 103B sandwiched between the electrode 551B and the electrode 552. In addition, the light emitting device 550G includes an electrode 551G, an electrode 552, and an EL layer 103G sandwiched between the electrode 551G and the electrode 552. In addition, the light emitting device 550R includes an electrode 551R, an electrode 552, and an EL layer 103R sandwiched between the electrode 551R and the electrode 552. In addition, the EL layer (103B, 103G, 103R) has a stacked structure composed of a plurality of layers having different functions including the light emitting layer (105B, 105G, 105R). The specific structure of each layer of the light emitting device is as shown in the above embodiment, but is not limited thereto.
[0290] In addition, Figure 3A In the embodiment, the light receiving device 550PS includes an electrode 551PS, an electrode 552, and a light receiving layer 103PS sandwiched between the electrode 551PS and the electrode 552. The light receiving layer 103PS has a stacked structure consisting of a plurality of layers having different functions including an active layer 105PS. The active layer 105PS includes a semiconductor. Examples of the semiconductor include inorganic semiconductors such as silicon and organic semiconductors including organic compounds. The specific structure of the other layers of the light receiving device can adopt the same structure as the light emitting device.
[0291] Figure 3A The following cases are shown: the EL layer 103B includes a hole injection / transport layer 104B, a light-emitting layer 105B, an electron transport layer 108B, and an electron injection layer 109; the EL layer 103G includes a hole injection / transport layer 104G, a light-emitting layer 105G, an electron transport layer 108G, and an electron injection layer 109; the EL layer 103R includes a hole injection / transport layer 104R, a light-emitting layer 105R, an electron transport layer 108R, and an electron injection layer 109; and the light-receiving layer 103PS includes a hole injection / transport layer 104PS, an active layer 105PS, an electron transport layer 108PS, and an electron injection layer 109. However, the present invention is not limited to this.
[0292] exist Figure 3AIn the embodiment, the electron injection layer 109 and the electrode 552 are layers (common layers) shared by the various devices (the light-emitting device 550B, the light-emitting device 550G, the light-emitting device 550R, and the light-receiving device 550PS).
[0293] In the following, for the sake of simplicity, the light-emitting device 550B, the light-emitting device 550G and the light-emitting device 550R are sometimes collectively referred to as the light-emitting device 550, the electrode 551B, the electrode 551G and the electrode 551R are collectively referred to as the electrode 551, the EL layer 103B, the EL layer 103G and the EL layer 103R are collectively referred to as the EL layer 103, the hole injection / transport layer 104B, the hole injection / transport layer 104G and the hole injection / transport layer 104R are collectively referred to as the hole injection / transport layer 104, the light-emitting layer 105B, the light-emitting layer 105G and the light-emitting layer 105R are collectively referred to as the light-emitting layer 105, and the electron transport layer 108B, the electron transport layer 108G and the electron transport layer 108R are collectively referred to as the electron transport layer 108.
[0294] like Figure 3A As shown, an insulating layer 107 is formed on the side (or end) of the hole injection / transport layer 104, the light-emitting layer 105, and the electron transport layer 108 in the layers of the EL layer 103, and on the side (or end) of the hole injection / transport layer 104PS, the active layer 105PS, and the electron transport layer 108PS in the layers of the light-receiving layer 103PS. The insulating layer 107 is in contact with the side (or end) of the EL layer 103 and the light-receiving layer 103PS. Thus, it is possible to suppress the entry of oxygen, moisture, or their constituent elements into the inside from the side of the EL layer 103 and the light-receiving layer 103PS. In addition, the insulating layer 107 continuously covers the side (or end) of a portion of the EL layer 103 of the adjacent light-emitting device or a portion of the light-receiving layer 103PS of the light-receiving device. For example, in Figure 3A In the embodiment, the side surfaces of a portion of the EL layer 103B of the light-emitting device 550B and a portion of the EL layer 103G of the light-emitting device 550G are covered by the continuous insulating layer 107 .
[0295] In addition, if Figure 3A As shown, a partition wall 528 is provided between each device. Note that the electron injection layer 109 and the electrode 552, which are common layers of each device, are not separated by the partition wall 528 but are continuously provided. Therefore, it can be said that the partition wall 528 is provided in the region surrounded by the electron injection layer 109 and the insulating layer 107. In addition, the partition wall 528 is located on the side (or end) of the electrode 551, a part of the EL layer 103 (hole injection / transport layer 104, light-emitting layer 105 and electron transport layer 108) and a part of the light-receiving layer 103PS (hole injection / transport layer 104PS, active layer 105PS and electron transport layer 108PS) across the insulating layer 107.
[0296] In the EL layer 103 and the light-receiving layer 103PS, the hole injection layer included in the hole transport region located between the anode and the light-emitting layer and between the anode and the active layer has a high conductivity in many cases, so if it is formed as a layer shared by adjacent devices, this sometimes causes crosstalk. Therefore, by separating a part of the EL layer 103 (hole injection / transport layer 104, light-emitting layer 105, and electron transport layer 108) and a part of the light-receiving layer 103PS (hole injection / transport layer 104PS, active layer 105PS, and electron transport layer 108PS) as shown in this structural example and providing an insulating layer 107 and a partition wall 528 therebetween, crosstalk between adjacent devices can be suppressed.
[0297] A recessed portion formed between adjacent devices can also be planarized by providing the partition wall 528. By planarizing the recessed portion, disconnection of the electron injection layer 109 and the electrode 552 formed on the EL layer 103 and the light-receiving layer 103PS can be suppressed.
[0298] The insulating layer 107 may be formed by, for example, aluminum oxide, magnesium oxide, hafnium oxide, gallium oxide, indium gallium zinc oxide, silicon nitride, or silicon oxynitride. In addition, the insulating layer 107 may be formed by stacking the above materials. In addition, the insulating layer 107 may be formed by sputtering, CVD, molecular beam epitaxy (MBE), pulsed laser deposition (PLD), atomic layer deposition (ALD), etc., preferably by using an ALD method with good coverage.
[0299] In addition, as an insulating material for forming the partition wall 528, for example, an organic material such as acrylic resin, polyimide resin, epoxy resin, imide resin, polyamide resin, polyimide amide resin, silicone resin, siloxane resin, benzocyclobutene resin, phenolic resin and precursors of these resins can be used. In addition, organic materials such as polyvinyl alcohol (PVA), polyvinyl butyral, polyvinyl pyrrolidone, polyethylene glycol, polyglycerol, pullulan, water-soluble cellulose or polyamide resin soluble in alcohol can also be used. In addition, photosensitive resins such as photoresists can be used. Note that the photosensitive resin can use positive materials or negative materials.
[0300] By using a photosensitive resin, the partition wall 528 can be manufactured only by the process of exposure and development. In addition, the partition wall 528 can also be formed using a negative photosensitive resin (such as a resist material). In addition, when an insulating layer containing an organic material is used as the partition wall 528, it is preferable to use a material that absorbs visible light. By using a material that absorbs visible light for the partition wall 528, the light emitted from the EL layer can be absorbed by the partition wall 528, thereby suppressing the light (stray light) that may leak to the adjacent EL layer and the light-receiving layer. Therefore, a light-receiving and light-emitting device with high display quality can be provided.
[0301] The difference between the height of the top surface of the partition wall 528 and the height of the top surface of any layer of the EL layer 103 and the light-receiving layer 103PS is preferably, for example, 0.5 times or less, and more preferably 0.3 times or less, the thickness of the partition wall 528. For example, the partition wall 528 may be provided so that the top surface of any layer of the EL layer 103 and the light-receiving layer 103PS is higher than the top surface of the partition wall 528. For example, the partition wall 528 may be provided so that the top surface of the partition wall 528 is higher than the top surfaces of the light-emitting layers included in the EL layer 103B, the EL layer 103G, and the EL layer 103R, and the active layer included in the light-receiving layer 103PS.
[0302] In a high-definition light-receiving and light-emitting device exceeding 1000 ppi, when crosstalk occurs between the devices, the color gamut that can be displayed by the light-receiving and light-emitting device becomes narrow. In a high-definition or ultra-high-definition light-receiving and light-emitting device exceeding 1000 ppi, preferably exceeding 2000 ppi, and more preferably exceeding 5000 ppi, an insulating layer 107 and a partition wall 528 are provided between a part of the EL layer 103 (hole injection / transport layer 104, light-emitting layer 105B, and electron transport layer 108) and a part of the light-receiving layer 103PS (hole injection / transport layer 104, active layer 105PS, and electron transport layer 108), thereby providing a light-receiving and light-emitting device capable of displaying vivid colors.
[0303] Figure 3B and Figure 3C is corresponding to Figure 3A The schematic top view of the light-emitting device 700 along the dotted line Ya-Yb in the cross-sectional view of FIG. That is, each device is arranged in a matrix. Note that Figure 3B The so-called stripe arrangement in which light emitting devices or light receiving devices of the same color are arranged in the X direction is shown. Figure 3C The structure in which light emitting devices or light receiving devices of the same color are arranged in the X direction and patterned for each pixel is shown. Note that the arrangement method of the light emitting devices is not limited to this, and an arrangement method such as a delta arrangement, a zigzag arrangement, a pentile arrangement, a diamond arrangement, etc. can be used.
[0304] Note that since patterning is performed using photolithography in the separation process of a portion of the EL layer 103 (hole injection / transport layer 104, light-emitting layer 105B, and electron transport layer 108) and a portion of the light-receiving layer 103PS (hole injection / transport layer 104, active layer 105PS, and electron transport layer 108), a high-definition light-receiving device (display panel) can be manufactured. In addition, the ends (sides) of each layer of a portion of the EL layer 103 processed by patterning using photolithography and each layer of a portion of the light-receiving layer 103PS are shaped to have approximately the same surface (or, located on approximately the same plane). At this time, the width (SE) of the gap 580 provided between each EL layer and the light-receiving layer is preferably less than 5 μm, and more preferably less than 1 μm.
[0305] Figure 3D is corresponding to Figure 3B and Figure 3C Schematic cross-sectional view of the dot-dash line C1-C2 in FIG. Figure 3D The connecting portion 560C is shown to electrically connect the connecting electrode 551C and the electrode 552. In the connecting portion 560C, the electrode 552 is provided on the connecting electrode 551C so as to be in contact therewith. In addition, the partition wall 528 is provided so as to cover the end of the connecting electrode 551C.
[0306] <Example of a method for manufacturing a light-receiving and light-emitting device> like Figure 4A As shown in FIG. 5 , an electrode 551B, an electrode 551G, an electrode 551R, and an electrode 551PS are formed. For example, a conductive film is formed on the functional layer 520 formed on the first substrate 510, and the conductive film is processed into a predetermined shape by photolithography.
[0307] Note that the conductive film can be formed by sputtering, CVD, MBE, vacuum evaporation, PLD, ALD, etc. As the CVD method, a plasma enhanced chemical vapor deposition (PECVD: Plasma Enhanced CVD) method or a thermal CVD method can be cited. In addition, as one of the thermal CVD methods, an organic metal chemical vapor deposition (MOCVD: Metal OrganicCVD) method can be cited.
[0308] When processing the conductive film, in addition to the above-mentioned photolithography, the thin film can also be processed by nanoimprinting, sandblasting, lift-off, etc. In addition, an island-shaped thin film can be directly formed by a film forming method using a shadow mask such as a metal mask.
[0309] There are two typical photolithography methods. One is a method of forming a resist mask on a thin film to be processed, processing the thin film by etching or the like, and removing the resist mask. The other is a method of forming a photosensitive thin film and then exposing and developing the thin film to a desired shape. Note that when using the former method, there are heat treatment steps such as heating after resist coating (PAB: Pre Applied Bake) and heating after exposure (PEB: Post Exposure Bake). In one embodiment of the present invention, in addition to the processing of a conductive film, a lithography technique is used in the processing of a thin film (a film formed of an organic compound or a film in which a portion thereof contains an organic compound) used to form an EL layer.
[0310] In the photolithography method, as the light used for exposure, for example, i-line (wavelength 365nm), g-line (wavelength 436nm), h-line (wavelength 405nm) or light mixed with these rays can be used. In addition, ultraviolet light, KrF laser or ArF laser, etc. can also be used. In addition, liquid immersion exposure technology can also be used for exposure. In addition, as the light used for exposure, extreme ultraviolet (EUV: Extreme Ultra-violet) light or X-rays can also be used. In addition, an electron beam can also be used instead of the light used for exposure. When extreme ultraviolet light, X-rays or electron beams are used, extremely fine processing can be performed, so it is preferred. Note that when exposure is performed by scanning with a light beam such as an electron beam, a photomask is not required.
[0311] As thin film etching using a resist mask, dry etching, wet etching, sand blasting, or the like can be used.
[0312] Then, if Figure 4B As shown, a hole injection / transport layer 104B, a light-emitting layer 105B, and an electron transport layer 108B are formed on the electrode 551B, the electrode 551G, the electrode 551R, and the electrode 551PS. For example, the hole injection / transport layer 104B, the light-emitting layer 105B, and the electron transport layer 108B can be formed using a vacuum evaporation method. Furthermore, a sacrificial layer 110B is formed on the electron transport layer 108B. When forming the hole injection / transport layer 104B, the light-emitting layer 105B, and the electron transport layer 108B, for example, the materials described in the above embodiment can be used.
[0313] The sacrificial layer 110B preferably uses a film with high resistance to etching treatment of the hole injection / transport layer 104B, the light-emitting layer 105B, and the electron transport layer 108B, that is, a film with a relatively large etching selectivity. In addition, the sacrificial layer 110B preferably adopts a stacked structure of a first sacrificial layer and a second sacrificial layer having different etching selectivities. In addition, the sacrificial layer 110B can use a film that can be removed by a wet etching method that causes less damage to the EL layer 103B. Oxalic acid or the like can be used as an etching material for wet etching. Note that in this specification, etc., the sacrificial layer may also be referred to as a mask layer.
[0314] The sacrificial layer 110B may be an inorganic film such as a metal film, an alloy film, a metal oxide film, a semiconductor film, or an inorganic insulating film. The sacrificial layer 110B may be formed by various film forming methods such as sputtering, vapor deposition, CVD, or ALD.
[0315] As the sacrificial layer 110B, for example, metal materials such as gold, silver, platinum, magnesium, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, palladium, titanium, aluminum, yttrium, zirconium, and tantalum, or alloy materials containing the metal materials can be used. In particular, low melting point materials such as aluminum and silver are preferably used.
[0316] In addition, as the sacrificial layer 110B, a metal oxide such as indium gallium zinc oxide (In-Ga-Zn oxide, also referred to as IGZO) can be used. In addition, indium oxide, indium zinc oxide (In-Zn oxide), indium tin 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), etc. can be used. Alternatively, indium tin oxide containing silicon can also be used.
[0317] Note that an element M (M is one or more selected from aluminum, silicon, boron, yttrium, copper, vanadium, beryllium, titanium, iron, nickel, germanium, zirconium, molybdenum, lanthanum, cerium, neodymium, hafnium, tantalum, tungsten and magnesium) may be used instead of the above gallium. In particular, M is preferably one or more selected from gallium, aluminum and yttrium.
[0318] Alternatively, an inorganic insulating material such as aluminum oxide, hafnium oxide, or silicon oxide may be used as the sacrificial layer 110B.
[0319] As the sacrificial layer 110B, it is preferred to use a material that is soluble in a solvent that is chemically stable to at least the electron transport layer 108B located at the top. In particular, a material that is soluble in water or alcohol can be appropriately used as the sacrificial layer 110B. When depositing the sacrificial layer 110B, it is preferred that the material is applied by a wet deposition method in a state dissolved in a solvent such as water or alcohol, and then a heating treatment is performed to evaporate the solvent. At this time, by performing a heat treatment under a reduced pressure atmosphere, the solvent can be removed at a low temperature and in a short time, so the thermal damage to the hole injection / transport layer 104B, the light-emitting layer 105B, and the electron transport layer 108B can be reduced, and therefore it is preferred.
[0320] Note that when a stacked-layer structure is adopted as the sacrificial layer 110B, a layer formed of the above-mentioned material may be used as a first sacrificial layer, and a second sacrificial layer may be formed thereon to form a stacked-layer structure.
[0321] At this time, the second sacrificial layer is a film used as a hard mask when etching the first sacrificial layer. In addition, the first sacrificial layer is exposed when processing the second sacrificial layer. Therefore, as the first sacrificial layer and the second sacrificial layer, a combination of films with a relatively large etching selectivity is selected. Therefore, a film that can be used for the second sacrificial layer can be selected according to the etching conditions of the first sacrificial layer and the etching conditions of the second sacrificial layer.
[0322] For example, when dry etching using a gas containing fluorine (also referred to as a fluorine-based gas) is used as the etching of the second sacrificial layer, silicon, silicon nitride, silicon oxide, tungsten, titanium, molybdenum, tantalum, tantalum nitride, an alloy containing molybdenum and niobium, or an alloy containing molybdenum and tungsten can be used for the second sacrificial layer. Here, as a film having a relatively large etching selectivity (i.e., a slow etching rate) for the above-mentioned dry etching using a fluorine-based gas, there are metal oxide films such as IGZO and ITO, and the above-mentioned films can be used for the first sacrificial layer.
[0323] In addition, the second sacrificial layer is not limited thereto, and can be selected from various materials according to the etching conditions of the first sacrificial layer and the etching conditions of the second sacrificial layer. For example, it can also be selected from the films that can be used for the first sacrificial layer.
[0324] In addition, as the second sacrificial layer, for example, a nitride film can be used, and specifically, nitrides such as silicon nitride, aluminum nitride, hafnium nitride, titanium nitride, tantalum nitride, tungsten nitride, gallium nitride, and germanium nitride can be used.
[0325] Alternatively, an oxide film may be used as the second sacrificial layer. Typically, an oxide film or an oxynitride film such as silicon oxide, silicon oxynitride, aluminum oxide, aluminum oxynitride, hafnium oxide, or hafnium oxynitride may be used.
[0326] Then, if Figure 4CAs shown, a resist is applied on the sacrificial layer 110B, and the resist is formed into a desired shape (resist mask: RES) by photolithography. In addition, when this method is adopted, there are heat treatment processes such as heating after resist coating (PAB: PreApplied Bake) and heating after exposure (PEB: Post Exposure Bake). For example, the PAB temperature is about 100°C and the PEB temperature is about 120°C. Therefore, the light-emitting device needs to be able to withstand these processing temperatures.
[0327] Next, a portion of the sacrificial layer 110B not covered by the resist mask RES is etched away using the obtained resist mask RES, the resist mask RES is removed, and then the hole injection / transport layer 104B, the light-emitting layer 105B, and the electron transport layer 108B not covered by the sacrificial layer are removed by etching, and the hole injection / transport layer 104B, the light-emitting layer 105B, and the electron transport layer 108B are processed into a shape having a side (or an exposed side) on the electrode 551B or a strip shape extending in a direction intersecting the page. In addition, dry etching can be used as the above-mentioned etching. In the case where the sacrificial layer 110B has a stacked structure of the above-mentioned first sacrificial layer and the above-mentioned second sacrificial layer, the resist mask RES can be removed after a portion of the second sacrificial layer is etched using the resist mask RES, and a portion of the first sacrificial layer is etched using the second sacrificial layer as a mask to process the hole injection / transport layer 104B, the light-emitting layer 105B, and the electron transport layer 108B into a specified shape. By performing these etching treatments, a Figure 5A shape.
[0328] Then, if Figure 5B As shown, a hole injection / transport layer 104G, a light-emitting layer 105G, and an electron transport layer 108G are formed on the sacrificial layer 110B, the electrode 551G, the electrode 551R, and the electrode 551PS. When forming the hole injection / transport layer 104G, the light-emitting layer 105G, and the electron transport layer 108G, for example, the materials described in the above embodiment can be used. In addition, for example, the hole injection / transport layer 104G, the light-emitting layer 105G, and the electron transport layer 108G can be formed using a vacuum evaporation method.
[0329] Subsequently, in the same manner as the hole injection / transport layer 104B, the light emitting layer 105B, the electron transport layer 108B, and the sacrificial layer 110B are formed, the hole injection / transport layer 104G, the light emitting layer 105G, the electron transport layer 108G, and the sacrificial layer 110G are formed on the electrode 551G, the hole injection / transport layer 104R, the light emitting layer 105R, the electron transport layer 108R, and the sacrificial layer 110R are formed on the electrode 551R, and the hole injection / transport layer 104PS, the active layer 105PS, the electron transport layer 108PS, and the sacrificial layer 110PS are formed on the electrode 551PS, thereby obtaining Figure 5C shape.
[0330] Then, if Fig. 6A As shown, an insulating layer 107 is formed on the sacrificial layer 110B, the sacrificial layer 110G, the sacrificial layer 110R, and the sacrificial layer 110PS.
[0331] In addition, the insulating layer 107 can be formed by using an ALD method, for example. Fig. 6A As shown, the insulating layer 107 is formed in a manner to contact the side surfaces (ends) of the hole injection / transport layer (104B, 104G, 104R, 104PS), the light-emitting layer (105R, 105G, 105R), the active layer 105PS, and the electron transport layer (108B, 108G, 108R, 108PS) of each device. Thus, it is possible to suppress the entry of oxygen, moisture, or their constituent elements into the interior from the side surfaces.
[0332] Then, if Figure 6B As shown in FIG. 1 , a resin film 528a is formed on the insulating layer 107. As the resin film 528a, for example, a negative photosensitive resin or a positive photosensitive resin can be used.
[0333] Then, if Figure 6C As shown, part of the resin film 528a, part of the insulating layer 107, and the sacrificial layers (110B, 110G, 110R, 110PS) are removed, thereby exposing the top surfaces of the electron transport layers (108B, 108G, 108R, 108PS).
[0334] Then, if Fig.6D As shown in FIG. 5 , the partition wall 528 is formed by performing a heat treatment so that the upper end of the resin film 528a has a curved surface shape. By making the upper end of the partition wall 528 have a curved surface shape, it is possible to achieve good coverage of the electron injection layer 109 to be formed later. For example, when a positive photosensitive acrylic resin is used as the resin film 528a, it is preferable to make the upper end of the partition wall 528 have a curved surface having a curvature radius (0.2 μm or more and 3 μm or less).
[0335] Next, an electron injection layer 109 is formed over the insulating layer 107, the electron transport layers (108B, 108G, 108R, and 108PS), and the partition wall 528. The materials described in the above embodiment modes can be used to form the electron injection layer 109. For example, the electron injection layer 109 is formed by vacuum deposition.
[0336] Then, if Fig. 7A As shown in FIG. 1 , an electrode 552 is formed on the electron injection layer 109. For example, the electrode 552 is formed by vacuum evaporation.
[0337] Through the above steps, the EL layer 103B, the EL layer 103G, the EL layer 103R, and the light-receiving layer 103PS in the light-emitting device 550B, the light-emitting device 550G, the light-emitting device 550R, and the light-receiving device 550PS can be separated and processed.
[0338] As described above, by performing patterning using photolithography in the separation process of the EL layer 103 and the light-receiving layer 103PS, a high-definition light-receiving device (display panel) can be manufactured. In addition, the ends (sides) of each layer of the EL layer and the light-receiving layer processed by patterning using photolithography become shapes having approximately the same surface (or, located on approximately the same plane). In addition, by performing patterning using photolithography, crosstalk between adjacent light-emitting devices and light-receiving devices can be suppressed. In addition, each end (side) processed by patterning using photolithography has a gap 580 between it and the adjacent device. Figure 7C In the figure, when the gap 580 is recorded as the distance SE between the EL layers or photoelectric conversion layers of adjacent light-emitting devices, the smaller the distance SE, the higher the aperture ratio and the higher the definition. On the other hand, since the larger the distance SE, the more the influence of the uneven manufacturing process between adjacent light-emitting devices can be allowed, the manufacturing yield can be improved. Since it is suitable for the miniaturization process of light-emitting devices manufactured by this specification, the distance SE between the EL layers of adjacent light-emitting devices can be greater than 0.5 μm and less than 5 μm, preferably greater than 1 μm and less than 3 μm, more preferably greater than 1 μm and less than 2.5 μm, and further preferably greater than 1 μm and less than 2 μm. Note that the distance SE is typically preferably greater than 1 μm and less than 2 μm (for example, 1.5 μm or thereabouts).
[0339] In this specification, etc., a device manufactured using a metal mask or FMM (Fine Metal Mask) is sometimes referred to as a device of MM (Metal Mask) structure. In addition, in this specification, etc., a device manufactured without using a metal mask or FMM is sometimes referred to as a device of MML (Metal Mask Less) structure. Since the light-emitting device of MML structure is manufactured without using a metal mask, its pixel configuration and pixel shape have a higher degree of freedom in design than the light-emitting device of FMM structure or MM structure.
[0340] The island-shaped EL layer of the light-receiving and light-emitting device of the MML structure is formed by processing the EL layer after the EL layer is formed, without using the pattern of the metal mask. Therefore, a light-receiving and light-emitting device with a higher definition or aperture ratio than the existing light-receiving and light-emitting device can be realized. Furthermore, since the EL layers of each color can be formed separately, a light-receiving and light-emitting device with extremely clear, extremely high contrast and extremely high display quality can be realized. In addition, by providing a sacrificial layer on the EL layer, the damage to the EL layer during the manufacturing process can be reduced, and the reliability of the light-emitting device can be improved.
[0341] In addition, Figure 3A and Fig. 7A In the light-emitting device 550 shown, the width of the EL layer 103 is substantially equal to the width of the electrode 551, and in the light-receiving device 550PS, the width of the light-receiving layer 103PS is substantially equal to the width of the electrode 551PS, but one embodiment of the present invention is not limited to this.
[0342] In the light-emitting device 550, the width of the EL layer 103 may be smaller than the width of the electrode 551. In addition, in the light-receiving device 550PS, the width of the light-receiving layer 103PS may be smaller than the width of the electrode 551PS. Figure 7B An example is shown in which the width of the EL layer 103B in the light-emitting device 550B is smaller than the width of the electrode 551B.
[0343] In the light-emitting device 550, the width of the EL layer 103 may be larger than the width of the electrode 551. In the light-receiving device 550PS, the width of the light-receiving layer 103PS may be larger than the width of the electrode 551PS. Figure 7C An example is shown in which the width of the EL layer 103B in the light-emitting device 550B is larger than the width of the electrode 551R.
[0344] The structure described in this embodiment can be used in combination with the structure described in other embodiment modes as appropriate.
[0345] Implementation 4 In this embodiment, refer to FIG. 8A to FIG. 10 Description device 720. Note that FIG. 8A to FIG. 10The device 720 shown in the figure can be said to be a light-emitting device because it includes the light-emitting device shown in the above embodiment. However, the device 720 described in this embodiment can be applied to the display unit of an electronic device, etc., and thus can also be said to be a display panel or a display device. In addition, when the above-mentioned light-emitting device is used as a light source and includes a light-receiving device that can receive light from the light-emitting device, it can also be said to be a light-receiving device. In addition, these light-emitting devices, display panels, display devices, and light-receiving devices include at least a light-emitting device.
[0346] In addition, the light-emitting device, display panel, display device, and light-receiving device of the present embodiment can be a high-resolution or large-scale light-emitting device, display panel, display device, and light-receiving device. Therefore, for example, the light-emitting device, display panel, display device, and light-receiving device of the present embodiment can be used not only for electronic devices with large screens such as television devices, desktop or notebook personal computers, displays for computers, etc., digital signage, large-scale game machines such as pinball machines, etc., but also for digital cameras, digital video cameras, digital photo frames, mobile phones, portable game consoles, smart phones, watch-type terminals, tablet terminals, portable information terminals, and sound reproduction devices.
[0347] Fig. 8A It is a top view of these devices (including a light-emitting device, a display panel, a display device, and a light-receiving device) 720.
[0348] exist Fig. 8A In the embodiment, the device 720 has a structure in which a substrate 710 and a substrate 711 are bonded. In addition, the device 720 includes a display region 701, a circuit 704, and a wiring 706. In addition, the display region 701 includes a plurality of pixels. Fig. 8A The pixel 703(i,j) shown includes Figure 8B The pixel 703(i+1,j) adjacent to the pixel 703(i,j) is shown.
[0349] In addition, if Fig. 8A As shown, the device 720 has an IC (integrated circuit) 712 disposed on a substrate 710 by a COG (Chip On Glass) method or a COF (Chip On Film) method. As the IC 712, for example, an IC including a scan line driver circuit or a signal line driver circuit can be applied. Fig. 8A A structure in which an IC including a signal line driver circuit is used as the IC 712 and a scan line driver circuit is included as the circuit 704 is shown.
[0350] The wiring 706 has a function of supplying signals and power to the display area 701 and the circuit 704. The signals and power are input to the wiring 706 from the outside through the FPC (Flexible Printed Circuit) 713 or from the IC 712. In addition, the IC may not be provided in the device 720. In addition, the IC may be mounted on the FPC by a COF method or the like.
[0351] Figure 8B Pixel 703 (i, j) and pixel 703 (i+1, j) of display area 701 are shown. That is, pixel 703 (i, j) may include a plurality of sub-pixels, each of which includes a light-emitting device that emits a different color. In addition, in addition to this, pixel 703 (i, j) may also include a plurality of sub-pixels, each of which includes a light-emitting device that emits the same color. The sub-pixels of a pixel may be, for example, three types of sub-pixels. As the three types of sub-pixels, sub-pixels of the three colors of red (R), green (G) and blue (B), sub-pixels of the three colors of yellow (Y), cyan (C) and magenta (M), etc. may be cited. Alternatively, a pixel may include four types of sub-pixels. As the four types of sub-pixels, sub-pixels of the four colors of R, G, B, and white (W), sub-pixels of the four colors of R, G, B, and Y, etc. may be cited. Specifically, the pixel 703 (i, j) can be formed using a pixel 702B (i, j) that displays blue, a pixel 702G (i, j) that displays green, and a pixel 702R (i, j) that displays red.
[0352] In addition, the sub-pixel may include a light-receiving device in addition to the light-emitting device. In the case where the sub-pixel includes a light-receiving device, the device 720 may also be referred to as a light-receiving device.
[0353] FIG. 8C to FIG. 8F An example of various layouts when a pixel 703 (i, j) includes a sub-pixel 702PS (i, j) having a light receiving device is shown. Figure 8C The arrangement of the pixels shown is a stripe arrangement. Fig.8D The arrangement of the pixels shown is a matrix arrangement. Fig. 8E The pixel shown has a structure in which three sub-pixels (sub-pixel R, sub-pixel G, and sub-pixel PS) are arranged vertically adjacent to one sub-pixel (sub-pixel B). Fig.8FIn the pixel shown, three sub-pixels G, B, and R that are longer in the vertical direction are arranged horizontally, and sub-pixels PS and IR that are longer in the horizontal direction are arranged horizontally below them. In addition, there is no particular limitation on the wavelength of light detected by sub-pixel 702PS (i, j), but the light-receiving device of sub-pixel 702PS (i, j) is preferably sensitive to light emitted by the light-emitting device of sub-pixel 702R (i, j), sub-pixel 702G (i, j), sub-pixel 702B (i, j), or sub-pixel 702IR (i, j). For example, it is preferred to detect one or more of light in wavelength regions such as blue, purple, blue-purple, green, yellow-green, yellow, orange, and red, and light in the infrared wavelength region.
[0354] In addition, if Fig.8F As shown, a sub-pixel 702IR(i, j) emitting infrared light may be added to the above group to form pixel 703(i, j). Specifically, a sub-pixel emitting light including light with a wavelength of more than 650 nm and less than 1000 nm may be used for pixel 703(i, j).
[0355] The arrangement of sub-pixels is not limited to FIG. 8A to FIG. 8F The structure shown in FIG. 1 can be replaced by various arrangements. Examples of the arrangement of sub-pixels include a stripe arrangement, an S-stripe arrangement, a matrix arrangement, a Delta arrangement, a Bayer arrangement, and a Pentile arrangement.
[0356] In addition, as the top surface shape of the sub-pixel, for example, there can be cited a triangle, a quadrangle (including a rectangle, a square), a polygon such as a pentagon, the above polygonal shapes with rounded corners, an ellipse or a circle, etc. Here, the top surface shape of the sub-pixel is equivalent to the top surface shape of the light-emitting region of the light-emitting device.
[0357] When the pixel includes a light emitting device and a light receiving device, the pixel has a light receiving function, so that the contact or approach of an object can be detected while displaying an image. For example, not only all sub-pixels included in the light emitting device display an image, but also some sub-pixels can present light used as a light source and other sub-pixels can display an image.
[0358] In addition, the light receiving area of sub-pixel 702PS(i, j) is preferably smaller than the light emitting area of other sub-pixels. The smaller the light receiving area, the narrower the imaging range, which can suppress blurring of the imaging result and improve the resolution. Therefore, by using sub-pixel 702PS(i, j), imaging can be performed with high definition or high resolution. For example, sub-pixel 702PS(i, j) can be used for imaging for personal identification using fingerprints, palm prints, irises, vein shapes (including vein shapes, artery shapes) or faces.
[0359] In addition, the sub-pixel 702PS(i, j) can be used for a touch sensor (also called a direct touch sensor) or an air touch sensor (also called a suspended sensor, a suspended touch sensor, a non-contact sensor, or a contactless sensor). For example, the sub-pixel 702PS(i, j) preferably detects infrared light. Thus, a touch can be detected even in a dark place.
[0360] Here, the touch sensor or the mid-air touch sensor can detect the approach or contact of an object (finger, hand, pen, etc.). The touch sensor can detect the object when the light-receiving device is in direct contact with the object. In addition, the mid-air touch sensor can detect the object even if the object does not contact the light-receiving device. For example, preferably, the light-receiving device can detect the object within a range of 0.1 mm to 300 mm, preferably 3 mm to 50 mm, between the light-receiving device and the object. By adopting this structure, the operation can be performed without the object directly contacting the light-receiving device. In other words, the light-receiving device can be operated in a non-contact (contactless) manner. By adopting the above structure, the risk of the light-receiving device being soiled or damaged can be reduced, or the light-receiving device can be operated without the object directly contacting the stain (for example, garbage, bacteria or viruses, etc.) attached to the light-receiving device.
[0361] Because high-definition video is performed, sub-pixels 702PS(i, j) are preferably set in all pixels included in the light-receiving and light-emitting device. On the other hand, sub-pixels 702PS(i, j) used for touch sensors or air touch sensors do not require high detection accuracy compared to the case of photographing fingerprints, etc., so sub-pixels 702PS(i, j) can be set in some pixels included in the light-receiving and light-emitting device. By making the number of sub-pixels 702PS(i, j) included in the light-receiving and light-emitting device less than the number of sub-pixels 702R(i, j), etc., the detection speed can be increased.
[0362] Next, refer to Fig.9A An example of a pixel circuit including a sub-pixel of a light-emitting device is described. Fig.9A The pixel circuit 530 shown includes a light emitting device (EL) 550, a transistor M15, a transistor M16, a transistor M17, and a capacitor C3. A light emitting diode can be used as the light emitting device (EL) 550. In particular, the light emitting device described in the above embodiment is preferably used as the light emitting device (EL) 550.
[0363] exist Fig.9AIn the embodiment, the gate of the transistor M15 is electrically connected to the wiring VG, one of the source and the drain is electrically connected to the wiring VS, and the other of the source and the drain is electrically connected to one electrode of the capacitor C3 and the gate of the transistor M16. One of the source and the drain of the transistor M16 is electrically connected to the wiring V4, and the other of the source and the drain is electrically connected to the anode of the light emitting device (EL) 550 and one of the source and the drain of the transistor M17. The gate of the transistor M17 is electrically connected to the wiring MS, and the other of the source and the drain is electrically connected to the wiring OUT2. The cathode of the light emitting device (EL) 550 is electrically connected to the wiring V5.
[0364] Wiring V4 and wiring V5 are each supplied with a constant potential. The anode side and cathode side of the light emitting device (EL) 550 can be set to a high potential and a potential lower than the anode side, respectively. Transistor M15 is controlled by a signal supplied to wiring VG and is used as a selection transistor for controlling the selection state of pixel circuit 530. In addition, transistor M16 is used as a driving transistor for controlling the current flowing through the light emitting device (EL) 550 according to the potential supplied to the gate. When transistor M15 is in the on state, the potential supplied to wiring VS is supplied to the gate of transistor M16, and the luminous brightness of the light emitting device (EL) 550 can be controlled according to the potential. Transistor M17 is controlled by a signal supplied to wiring MS, and the potential between transistor M16 and the light emitting device (EL) 550 is output to the outside through wiring OUT2.
[0365] Fig.9A and Fig. 9B The transistors M11, M12, M13 and M14 included in the pixel circuit 531 and the transistors M15, M16 and M17 included in the pixel circuit 530 are preferably transistors whose channels are formed by semiconductor layers containing metal oxide (oxide semiconductor).
[0366] A transistor using a metal oxide having a wider band gap than silicon and a low carrier density can achieve an extremely low off-state current. Thus, because its off-state current is low, the charge stored in the capacitor connected in series with the transistor can be maintained for a long period of time. Therefore, in particular, transistors M11, M12, and M15 connected in series with capacitor C2 or capacitor C3 preferably use transistors containing oxide semiconductors. In addition, by using transistors that also apply oxide semiconductors for other transistors, manufacturing costs can be reduced.
[0367] Alternatively, transistors M11 to M17 may be transistors whose channels are formed of a semiconductor including silicon. In particular, it is preferred to use highly crystalline silicon such as single crystal silicon or polycrystalline silicon because high field effect mobility and higher speed operation can be achieved.
[0368] Note that at least one of the transistors M11 to M17 may be a transistor including an oxide semiconductor, and the other transistors may be a transistor including silicon.
[0369] Next, refer to Fig. 9B An example of a pixel circuit of a sub-pixel having a light-receiving device will be described. Fig. 9B The pixel circuit 531 shown includes a light receiving device (PD) 560, a transistor M11, a transistor M12, a transistor M13, a transistor M14, and a capacitor C2. Here, an example in which a photodiode is used as the light receiving device (PD) 560 is shown.
[0370] exist Fig. 9B In the embodiment, the anode of the light receiving device (PD) 560 is electrically connected to the wiring V1, and the cathode is electrically connected to one of the source and drain of the transistor M11. The gate of the transistor M11 is electrically connected to the wiring TX, and the other of the source and drain is electrically connected to one electrode of the capacitor C2, one of the source and drain of the transistor M12, and the gate of the transistor M13. The gate of the transistor M12 is electrically connected to the wiring RE1, and the other of the source and drain is electrically connected to the wiring V2. One of the source and drain of the transistor M13 is electrically connected to the wiring V3, and the other of the source and drain is electrically connected to one of the source and drain of the transistor M14. The gate of the transistor M14 is electrically connected to the wiring SE1, and the other of the source and drain is electrically connected to the wiring OUT1.
[0371] Wiring V1, wiring V2, and wiring V3 are each supplied with a constant potential. When the light receiving device (PD) 560 is driven with a reverse bias, a potential higher than that of wiring V1 is supplied to wiring V2. Transistor M12 is controlled by a signal supplied to wiring RE1, so that the potential of the node connected to the gate of transistor M13 is reset to the potential supplied to wiring V2. Transistor M11 is controlled by a signal supplied to wiring TX, and the timing of the potential change of the above-mentioned node is controlled according to the current flowing through the light receiving device (PD) 560. Transistor M13 is used as an amplifying transistor according to the potential output of the above-mentioned node. Transistor M14 is controlled by a signal supplied to wiring SE1 and is used as a selection transistor, which is used to read out the output according to the potential of the above-mentioned node using an external circuit connected to wiring OUT1.
[0372] exist Fig.9A and Fig. 9B In the embodiment, an n-channel transistor is used as the transistor, but a p-channel transistor may also be used.
[0373] The transistors included in the pixel circuit 530 and the transistors included in the pixel circuit 531 are preferably arranged on the same substrate. In particular, it is preferred that the transistors included in the pixel circuit 530 and the transistors included in the pixel circuit 531 are mixed and formed in one region and are arranged periodically.
[0374] In addition, one or more layers including one or both of a transistor and a capacitor are preferably provided at a position overlapping with the light receiving device (PD) 560 or the light emitting device (EL) 550. Thus, the effective occupied area of each pixel circuit can be reduced, thereby realizing a high-definition light receiving unit or display unit.
[0375] then, Fig. 9C Shown can be applied to reference Fig.9A and Fig. 9B An example of a specific structure of a transistor in a pixel circuit is described. Note that as the transistor, a bottom-gate transistor, a top-gate transistor, or the like can be used as appropriate.
[0376] Fig. 9C The transistor shown includes a semiconductor film 508, a conductive film 504, an insulating film 506, a conductive film 512A, and a conductive film 512B. The transistor is formed on the insulating film 501C, for example. In addition, the transistor includes an insulating film 516 (insulating film 516A and insulating film 516B) and an insulating film 518.
[0377] The semiconductor film 508 includes a region 508A electrically connected to the conductive film 512A and a region 508B electrically connected to the conductive film 512B. The semiconductor film 508 includes a region 508C between the region 508A and the region 508B.
[0378] The conductive film 504 includes a region overlapping with the region 508C, and the conductive film 504 functions as a gate electrode.
[0379] The insulating film 506 includes a region sandwiched between the semiconductor film 508 and the conductive film 504. The insulating film 506 has a function as a first gate insulating film.
[0380] The conductive film 512A has one of the function of a source electrode and the function of a drain electrode, and the conductive film 512B has the other of the function of a source electrode and the function of a drain electrode.
[0381] In addition, the conductive film 524 can be used for the transistor. The conductive film 524 includes a region in which the semiconductor film 508 is sandwiched between the conductive film 504. The conductive film 524 has a function of a second gate electrode. The insulating film 501D is sandwiched between the semiconductor film 508 and the conductive film 524 and has a function of a second gate insulating film.
[0382] The insulating film 516 is used, for example, as a protective film that covers the semiconductor film 508. Specifically, for example, a film containing a silicon oxide film, a silicon oxynitride film, a silicon nitride oxide film, a silicon nitride film, an aluminum oxide film, a hafnium oxide film, a yttrium oxide film, a zirconium oxide film, a gallium oxide film, a tantalum oxide film, a magnesium oxide film, a lanthanum oxide film, a cerium oxide film, or a neodymium oxide film can be used as the insulating film 516.
[0383] For example, a material that can suppress diffusion of oxygen, hydrogen, water, alkali metals, alkaline earth metals, and the like is preferably used for the insulating film 518. Specifically, for example, silicon nitride, silicon oxynitride, aluminum nitride, aluminum oxynitride, and the like can be used as the insulating film 518. In addition, as for the number of oxygen atoms and the number of nitrogen atoms contained in silicon oxynitride and aluminum oxynitride, respectively, it is preferable that the number of nitrogen atoms is larger.
[0384] In the process of forming a semiconductor film for a transistor of a pixel circuit, a semiconductor film for a transistor of a driver circuit may be formed. For example, a semiconductor film having the same composition as that of a semiconductor film in a transistor of a pixel circuit may be used for the driver circuit.
[0385] As the semiconductor film 508, for example, indium, M (M is one or more selected from gallium, aluminum, silicon, boron, yttrium, tin, copper, vanadium, beryllium, titanium, iron, nickel, germanium, zirconium, molybdenum, lanthanum, cerium, neodymium, hafnium, tantalum, tungsten and magnesium) and zinc are preferably contained. In particular, M is preferably one or more selected from aluminum, gallium, yttrium and tin.
[0386] In particular, as the semiconductor film 508, an oxide containing In, Ga, and Zn (also referred to as IGZO) is preferably used. Alternatively, an oxide containing In, Sn, and Zn is preferably used. Alternatively, an oxide containing In, Ga, Sn, and Zn is preferably used. Alternatively, an oxide containing In, Al, and Zn (also referred to as IAZO) is preferably used. Alternatively, an oxide containing In, Al, Ga, and Zn (also referred to as IAGZO) is preferably used.
[0387] When the semiconductor film is an In-M-Zn oxide, it is preferred that the atomic ratio of In in the In-M-Zn oxide is greater than or equal to the atomic ratio of M. Examples of the atomic ratio of the metal elements in the In-M-Zn oxide include a composition of In:M:Zn=1:1:1 or in the vicinity thereof, a composition of In:M:Zn=1:1:1.2 or in the vicinity thereof, a composition of In:M:Zn=1:3:2 or in the vicinity thereof, a composition of In:M:Zn=1:3:4 or in the vicinity thereof, a composition of In:M:Zn=2:1:3 or in the vicinity thereof, a composition of In:M:Zn=3:1:2 or in the vicinity thereof, and a composition of In:M:Zn=1:3:4 or in the vicinity thereof. =4:2:3 or a composition in the vicinity thereof, In:M:Zn=4:2:4.1 or a composition in the vicinity thereof, In:M:Zn=5:1:3 or a composition in the vicinity thereof, In:M:Zn=5:1:6 or a composition in the vicinity thereof, In:M:Zn=5:1:7 or a composition in the vicinity thereof, In:M:Zn=5:1:8 or a composition in the vicinity thereof, In:M:Zn=6:1:6 or a composition in the vicinity thereof, In:M:Zn=5:2:5 or a composition in the vicinity thereof, etc. Note that the nearby compositions include a range of ±30% of the desired atomic number ratio.
[0388] For example, when the atomic ratio of metal elements is described as In:Ga:Zn=4:2:3 or a composition in the vicinity thereof, the content ratio of each element includes the following cases: when In is 4, Ga is 1 or more and 3 or less, and Zn is 2 or more and 4 or less. In addition, when the atomic ratio of metal elements is described as In:Ga:Zn=5:1:6 or a composition in the vicinity thereof, the content ratio of each element includes the following cases: when In is 5, Ga is greater than 0.1 and 2 or less, and Zn is 5 or more and 7 or less. In addition, when the atomic ratio of metal elements is described as In:Ga:Zn=1:1:1 or a composition in the vicinity thereof, the content ratio of each element includes the following cases: when In is 1, Ga is greater than 0.1 and 2 or less, and Zn is greater than 0.1 and 2 or less.
[0389] There is no particular restriction on the crystallinity of the semiconductor material used for the transistor, and an amorphous semiconductor or a crystalline semiconductor (a microcrystalline semiconductor, a polycrystalline semiconductor, a single crystal semiconductor, or a semiconductor having a crystalline region in part thereof) can be used. When a crystalline semiconductor is used, it is preferred because it can suppress the degradation of the characteristics of the transistor.
[0390] In the case where metal oxide is used for the semiconductor film 508, the device 720 has a structure in which metal oxide is used for the semiconductor film and includes a light-emitting device having an MML (no fine metal mask) structure. By adopting this structure, the leakage current that can flow through the transistor and the leakage current that can flow between adjacent light-emitting devices (also called lateral leakage current, side leakage current, etc.) can be made extremely low. In addition, by adopting the above structure, when the image is displayed on the display device, the viewer can observe any one or more of the sharpness of the image, the sharpness of the image, the high color saturation and the high contrast. In addition, by adopting a structure in which the leakage current that can flow through the transistor and the lateral leakage current between the light-emitting devices are extremely low, a display (also called a pure black display) with extremely little light leakage (so-called blackening) that can occur when displaying black can be performed.
[0391] In addition, silicon can also be used as the semiconductor film 508. Examples of silicon include single crystal silicon, polycrystalline silicon, and amorphous silicon. In particular, it is preferable to use a transistor containing low temperature polycrystalline silicon (LTPS (Low Temperature PolySilicon)) in the semiconductor layer (hereinafter also referred to as an LTPS transistor). LTPS transistors have high field effect mobility and good frequency characteristics.
[0392] By using silicon transistors such as LTPS transistors, a circuit that needs to be driven at a high frequency (e.g., a source driver circuit) and a display unit can be formed on the same substrate. Therefore, the external circuit mounted on the light-emitting device can be simplified, and the component cost and mounting cost can be reduced.
[0393] In addition, the structure of the transistor used for the display panel can be appropriately selected according to the screen size of the display panel. For example, when a single-crystal Si transistor is used as a transistor of the display panel, it can be applied to a display panel with a screen size of 0.1 inches or more and 3 inches or less. In addition, when an LTPS transistor is used as a transistor of the display panel, it can be applied to a display panel with a screen size of 0.1 inches or more and 30 inches or less, and preferably applied to a display panel with a screen size of 1 inch or more and 30 inches or less. In addition, when the display panel adopts LTPO (a structure combining LTPS transistors and OS transistors), it can be applied to a display panel with a screen size of 0.1 inches or more and 50 inches or less, and preferably applied to a display panel with a screen size of 1 inch or more and 50 inches or less. In addition, when an OS transistor (a transistor containing a metal oxide in a semiconductor that forms a channel) is used as a transistor for a display panel, it can be used for a display panel with a screen size of 0.1 inches or more and 200 inches or less in diagonal size, and is preferably used for a display panel with a screen size of 50 inches or more and 100 inches or less.
[0394] Note that due to the size of the single-crystal Si substrate, it is difficult to enlarge the display panel using single-crystal Si transistors. In addition, LTPS transistors use laser crystallization devices in the manufacturing process, and it is difficult to apply them to large-scale (typically, screen sizes with a diagonal size of more than 30 inches). On the other hand, OS transistors do not have restrictions such as the use of laser crystallization devices in the manufacturing process, and can be manufactured at a lower process temperature (typically below 450°C), so they can be applied to display panels with larger areas (typically, diagonal sizes of 50 inches or more and 100 inches or less). In addition, when LTPO is used, it can be applied to display panel sizes between the sizes when using LTPS transistors and the sizes when using OS transistors (typically, diagonal sizes of 1 inch or more and 50 inches or less).
[0395] Next, a cross-sectional view of the light receiving and emitting device is shown. Fig.10 yes Fig. 8A A cross-sectional view of the device shown.
[0396] Fig.10 These are cross-sectional views showing a portion of a region including the FPC 713 and the wiring 706 and a portion of a display region 701 including the pixel 703 (i, j) cut out.
[0397] exist Fig.10 In the embodiment, the device 720 includes a functional layer 520 between a first substrate 510 and a second substrate 770. The functional layer 520 includes a first substrate 510 and a second substrate 770. 9A to 9C In addition to the transistors (M11, M12, M13, M14, M15, M16, M17) and capacitors (C2, C3), etc. described in the description, it also includes wiring (VS, VG, V1, V2, V3, V4, V5) that electrically connects them. Fig.10 The functional layer 520 is shown to include a pixel circuit 530X(i, j), a pixel circuit 530S(i, j), and a circuit GD, but the present invention is not limited to this structure.
[0398] The pixel circuit (eg, Fig.10 The pixel circuit 530X (i, j) and the pixel circuit 530S (i, j) shown in FIG. 5 are connected to the light emitting device and the light receiving device (eg, Fig.10The light emitting device 550X(i, j) and the light receiving device 550S(i, j) shown are electrically connected. Specifically, the light emitting device 550X(i, j) is electrically connected to the pixel circuit 530X(i, j) through the wiring 591X, and the light receiving device 550S(i, j) is electrically connected to the pixel circuit 530S(i, j) through the wiring 591S. In addition, an insulating layer 705 is provided on the functional layer 520, the light emitting device, and the light receiving device, and the insulating layer 705 has the function of bonding the second substrate 770 to the functional layer 520.
[0399] Note that a substrate including touch sensors in a matrix can be used as the second substrate 770. For example, a substrate including a capacitive touch sensor or an optical touch sensor can be used for the second substrate 770. Thus, the light receiving and light emitting device of one embodiment of the present invention can be used as a touch panel.
[0400] The structure described in this embodiment can be used in combination with the structure described in other embodiment modes as appropriate.
[0401] Implementation method 5 In this embodiment, refer to FIG. 11A to FIG. 13B The structure of an electronic device according to one embodiment of the present invention will be described.
[0402] FIG. 11A to FIG. 13B It is a diagram for explaining the structure of an electronic device according to one embodiment of the present invention. Fig.11A is a block diagram of an electronic device, FIG. 11B to FIG. 11E It is a perspective view illustrating the structure of an electronic device. FIG. 12A to FIG. 12E It is a perspective view illustrating the structure of an electronic device. Fig.13A and Fig. 13B It is a perspective view illustrating the structure of an electronic device.
[0403] The electronic device 5200B described in this embodiment includes a computing device 5210 and an input / output device 5220 (see Fig.11A ).
[0404] The computing device 5210 has a function of being supplied with operation data, and has a function of supplying image data based on the operation data.
[0405] The input / output device 5220 includes a display unit 5230, an input unit 5240, a detection unit 5250, and a communication unit 5290, and has a function of supplying operation data and a function of being supplied with image data. In addition, the input / output device 5220 has a function of supplying detection data, a function of supplying communication data, and a function of being supplied with communication data.
[0406] The input unit 5240 has a function of supplying operation data. For example, the input unit 5240 supplies operation data according to an operation of a user of the electronic device 5200B.
[0407] Specifically, a keyboard, a hardware button, a pointing device, a touch sensor, an illumination sensor, a camera device, an audio input device, a line of sight input device, a posture detection device, or the like can be used for the input unit 5240 .
[0408] The display portion 5230 includes a display panel and has a function of displaying image data. For example, the display panel described in Embodiment 3 can be used for the display portion 5230 .
[0409] The detection unit 5250 has a function of supplying detection data. For example, it has a function of detecting the surrounding environment where the electronic device is used and supplying the detection data.
[0410] Specifically, an illumination sensor, a camera device, a posture detection device, a pressure sensor, a human body sensing sensor, or the like can be used for the detection unit 5250 .
[0411] The communication unit 5290 has the function of being supplied with communication data and the function of supplying communication data. For example, it has the function of connecting with other electronic devices or communication networks by wireless communication or wired communication. Specifically, it has the functions of wireless LAN communication, telephone communication, short-range wireless communication, etc.
[0412] Fig. 11B An electronic device having an outer shape along a cylindrical pillar or the like is shown. As an example, a digital sign or the like can be cited. A display panel of one embodiment of the present invention can be used for the display unit 5230. Note that it can also have a function of changing the display method according to the illumination of the use environment. In addition, it has a function of changing the display content by sensing the presence of a human body. Therefore, for example, it can be set on a pillar of a building. Alternatively, it can display advertisements or guides.
[0413] Fig. 11C An electronic device having a function of generating image data according to the trajectory of a hand indicator used by a user is shown. An electronic blackboard, an electronic message board, a digital sign, etc. can be cited as an example. Specifically, a display panel with a diagonal length of 20 inches or more, preferably 40 inches or more, and more preferably 55 inches or more can be used. Alternatively, a plurality of display panels can be arranged and used as a display area. Alternatively, a plurality of display panels can be arranged and used as a multi-screen display panel.
[0414] Fig.11DAn electronic device that can receive data from other devices and display it on the display unit 5230 is shown. As an example, a wearable electronic device can be cited. Specifically, several options can be displayed or the user can select several items from the options and reply them to the sender of the data. In addition, for example, there is a function of changing the display method according to the illumination of the use environment. Thereby, for example, the power consumption of the wearable electronic device can be reduced. In addition, for example, the image is displayed on the wearable electronic device in a manner that the wearable electronic device can be appropriately used even in an environment with strong external light, such as outdoors on a sunny day.
[0415] Fig.11E An electronic device including a display unit 5230 having a curved surface gently curved along the side of a housing is shown. As an example, a mobile phone or the like can be cited. In addition, the display unit 5230 includes a display panel, and the display panel has, for example, a function of displaying on its front, side, top, and back. Thus, for example, data can be displayed not only on the front of the mobile phone, but also on the side, top, and back of the mobile phone.
[0416] Fig. 12A An electronic device that can receive data from the Internet and display it on the display unit 5230 is shown. As an example, a smartphone can be cited. For example, the notification made can be confirmed on the display unit 5230. In addition, the notification made can be sent to other devices. In addition, for example, there is a function of changing the display method according to the illumination of the use environment. Thereby, the power consumption of the smartphone can be reduced. In addition, for example, the image is displayed on the smartphone in a manner that allows the smartphone to be appropriately used even in an environment with strong external light, such as outdoors on a sunny day.
[0417] Fig. 12B An electronic device that can use a remote controller as an input unit 5240 is shown. As an example, a television system or the like can be cited. In addition, for example, data can be received from a broadcasting station or the Internet and displayed on the display unit 5230. In addition, the user can be photographed using the detection unit 5250. In addition, the user's image can be sent. In addition, the user's viewing history can be obtained and provided to a cloud service. In addition, recommended data can be obtained from the cloud service and displayed on the display unit 5230. In addition, programs or dynamic images can be displayed based on the recommended data. In addition, for example, there is a function of changing the display method according to the illumination of the use environment. Thus, images can be displayed on the television system in a manner that allows the television system to be appropriately used even in an environment where strong external light is incident on a sunny day.
[0418] Fig. 12CThe electronic device that can receive teaching materials from the Internet and display them on the display unit 5230 is shown. As an example, a tablet computer can be cited. In addition, a report can be input using the input unit 5240 and sent to the Internet. In addition, the correction results or evaluations of the report can be obtained from the cloud service and displayed on the display unit 5230. In addition, appropriate teaching materials can be selected based on the evaluation and displayed on the display unit 5230.
[0419] For example, an image signal can be received from another electronic device and displayed on the display portion 5230. In addition, the display portion 5230 can be placed on a stand or the like and used as a sub-display. For example, an image can be displayed on a tablet computer in such a manner that the electronic device can be appropriately used even in an environment with strong external light, such as outdoors on a sunny day.
[0420] Fig.12D An electronic device including a plurality of display units 5230 is shown. As an example, a digital camera or the like can be cited. For example, an image captured using the detection unit 5250 can be displayed on the display unit 5230. In addition, the captured image can be displayed on the detection unit. In addition, the captured image can be modified using the input unit 5240. In addition, text can be added to the captured image. In addition, it can be sent to the Internet. In addition, there is a function of changing the shooting conditions according to the illumination of the use environment. Thus, for example, the subject can be displayed on the digital camera in a manner that the image can be appropriately seen even in an environment with strong external light, such as outdoors on a sunny day.
[0421] Fig.12E An electronic device that can control other electronic devices by using other electronic devices as slaves and using the electronic device of this embodiment as a master is shown. As an example, a portable personal computer or the like can be cited. For example, a part of the image data can be displayed on the display unit 5230 and another part of the image data can be displayed on the display unit of the other electronic device. In addition, an image signal can be supplied. In addition, the communication unit 5290 can be used to obtain data written from the input unit of the other electronic device. Thus, for example, a larger display area can be utilized using a portable personal computer.
[0422] Fig.13AAn electronic device including a detection unit 5250 for detecting acceleration or orientation is shown. As an example, a goggles-type electronic device can be cited. In addition, the detection unit 5250 can supply data on the position of the user or the direction in which the user is facing. In addition, the electronic device can generate image data for the right eye and image data for the left eye based on the position of the user or the direction in which the user is facing. In addition, the display unit 5230 includes a display area for the right eye and a display area for the left eye. Thus, for example, a virtual reality space image that can obtain a realistic feeling can be displayed on a goggles-type electronic device.
[0423] Fig. 13B An electronic device including a camera device and a detection unit 5250 for detecting acceleration or orientation is shown. As an example, a glasses-type electronic device can be cited. In addition, the detection unit 5250 can provide data on the user's position or the direction the user is facing. In addition, the electronic device can generate image data based on the user's position or the direction the user is facing. Thus, for example, data can be added to a real scene and displayed. In addition, an image of an augmented reality space can be displayed on a glasses-type electronic device.
[0424] Note that this embodiment mode can be combined with other embodiment modes described in this specification as appropriate.
[0425] Implementation 6 In this embodiment, refer to Fig.14A and Fig. 14B A structure in which the light-emitting device described in the above embodiment is used in a lighting device will be described. Note that Fig.14A It is along Fig. 14B A cross-sectional view of line segment ef in a top view of the lighting device shown.
[0426] In the lighting device of this embodiment, the first electrode 401 is formed on a light-transmitting substrate 400 serving as a support. Reference numeral 401 corresponds to the first electrode 101 in the above embodiment. When light is extracted from the first electrode 401 side, the first electrode 401 is formed using a light-transmitting material.
[0427] A pad 412 for supplying a voltage to the second electrode 404 is formed on the substrate 400 .
[0428] An EL layer 403 is formed over the first electrode 401. The EL layer 403 has a structure corresponding to the EL layer 103 in Embodiment 2. Note that for these structures, refer to the respective descriptions.
[0429] The second electrode 404 is formed to cover the EL layer 403. The second electrode 404 corresponds to the second electrode 102 in the above embodiment. When light is extracted from the first electrode 401 side, the second electrode 404 is formed using a material with high reflectivity. By connecting the second electrode 404 to the pad 412, a voltage is supplied to the second electrode 404.
[0430] As described above, the lighting device described in this embodiment includes a light-emitting device including the first electrode 401, the EL layer 403, and the second electrode 404. Since the light-emitting device has high light emission efficiency, the lighting device of this embodiment can be a low-power lighting device.
[0431] The substrate 400 on which the light emitting device having the above structure is formed and the sealing substrate 407 are fixed and sealed using the sealing materials (405, 406), thereby manufacturing a lighting device. In addition, only one of the sealing materials 405 and 406 may be used. In addition, the inner sealing material 406 (at Fig. 14B The semiconductor device (not shown) is mixed with a desiccant, thereby absorbing moisture and improving reliability.
[0432] Furthermore, the pad 412 and part of the first electrode 401 can be used as an external input terminal by extending outside the sealing materials 405 and 406. Alternatively, an IC chip 420 or the like on which a converter or the like is mounted may be provided on the external input terminal.
[0433] Implementation 7 In this embodiment, refer to Fig.15 An application example of a lighting device manufactured by applying the light-emitting device of one embodiment of the present invention or a light-emitting device which is a part thereof will be described.
[0434] As an indoor lighting device, a ceiling spotlight 8001 can be used. As a ceiling spotlight 8001, there are direct installation types and embedded types. This lighting device is manufactured by combining a light-emitting device with a housing or a cover. In addition, it can also be applied to a lighting device of a chandelier (suspended from the ceiling with wires).
[0435] In addition, the foot lamp 8002 illuminates the ground, which can improve the safety of the foot. For example, it is very effective to use it in bedrooms, stairs, and passages. In this case, the size and shape of the foot lamp can be appropriately changed according to the size or structure of the room. In addition, the foot lamp 8002 can also be a mounting type lighting device formed by combining a light emitting device and a bracket.
[0436] In addition, the sheet lighting 8003 is a thin film lighting device. Because it is attached to the wall and used, it does not take up space and can be applied to various purposes. In addition, it is easy to achieve a large area. In addition, it can also be attached to a wall with a curved surface, a shell, etc.
[0437] Alternatively, a lighting device 8004 may be used in which light from a light source is controlled so as to be emitted only in a desired direction.
[0438] The desk lamp 8005 includes a light source 8006 . As the light source 8006 , a light-emitting device according to one embodiment of the present invention or a light-emitting device which is a part thereof can be used.
[0439] By using the light-emitting device of one embodiment of the present invention or a light-emitting device which is a part of the light-emitting device, other than the above, in a part of indoor furniture, a lighting device having the function of furniture can be provided.
[0440] As described above, various lighting devices to which the light emitting device is applied can be obtained. In addition, such lighting devices are included in one embodiment of the present invention.
[0441] The structure described in this embodiment mode can be used in combination with the structures described in other embodiment modes as appropriate. Example 1
[0442] (Synthesis Example 1) In this example, the results of various measurements are shown for synthesizing 4,4'-(diphenylsilanediyl)bis{N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylaniline (abbreviated as PSiYGA2) (structural formula (100)), an organic compound of one embodiment of the present invention. The structure of PSiYGA2 is shown below.
[0443] [Chemical formula 23]
[0444] 1.5 g (3.0 mmol) of bis(4-bromophenyl)diphenylsilane, 2.0 g (6.0 mmol) of N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylaniline, 1.0 g (10 mmol) of sodium tert-butoxide (abbreviated as tBuONa) and 0.1 mg (0.1 mmol) of bis(dibenzylideneacetone)palladium(0) (abbreviated as Pd(dba)2) were placed in a 300 mL three-necked flask, and the atmosphere in the flask was replaced with nitrogen. 100 mL of dehydrated xylene was added to the mixture. After the mixture was stirred and degassed under reduced pressure, 0.8 mL (0.4 mmol) of tri(tert-butyl)phosphine (abbreviated as (tBu)3P) (10 wt% hexane solution) was added to the mixture. The mixture was heated and stirred at 120°C for 6 hours under a nitrogen stream to cause a reaction. After the reaction, 150 mL of toluene was added to the reaction mixture, and the suspension was filtered through magnesium silicate and diatomaceous earth. The obtained filtrate was concentrated, and the solid was purified by silica gel column chromatography (developing solvent was a mixture of toluene and hexane) and then recrystallized to obtain the target white powder with a yield of 70% and an output of 2.1 g. In addition, the following (a-1) shows the reaction scheme of the above synthesis method.
[0445] [Chemical formula 24]
[0446] The Rf values in silica gel thin layer chromatography (TLC) (developing solvent: ethyl acetate:hexane=1:5) were as follows: 0.49 for the target product and 0.41 for bis(4-bromophenyl)diphenylsilane.
[0447] Fig.16 The sublimation purification of PSiYGA2 is shown in Figure 2. 1 H NMR spectrum. 1 H NMR measurement results. From these results, it was confirmed that PSiYGA2 was obtained.
[0448] 1 H NMR (CDCl3, 300MHz): δ (ppm) = 7.11 (t, J = 7.2Hz, 2H), 7.17 (d, J = 8.4, 4H), 7.2 5-7.44 (m, 34H), 7.51 (d, J=8.4, 4H), 7.61-7.65 (m, 4H), 8.13 (d, J=7.8, 4H).
[0449] Next, PSiYGA2 obtained in this example was analyzed by liquid chromatography-mass spectrometry (LC / MS analysis).
[0450] In the LC / MS analysis, LC (liquid chromatography) separation was performed using UltiMate 3000 manufactured by Thermo Fisher Scientific, and MS analysis (mass spectrometry) was performed using QExactive manufactured by Thermo Fisher Scientific.
[0451] In LC separation, an arbitrary column was used, the column temperature was 40°C, and the injection conditions were as follows: a solvent (acetonitrile aqueous solution) was appropriately selected, PSiYGA2 of an arbitrary concentration was dissolved in an organic solvent for sample adjustment, and the injection volume was 5.0 μL.
[0452] The MS / MS measurement of the exact mass of PSiYGA2 at m / z 1000.40 was performed using the Parallel Reaction Monitoring (PRM) method. The PRM settings were: the mass range of the target ion was m / z 1000.40 ± 2.0 (isolation window = 4); detection was performed in positive mode. The energy NCE (Normalized Collision Energy) for accelerating the target ion in the collision cell was set to 40 for measurement. Fig.17 Shown is an MS mass spectrum obtained by MS / MS measurement.
[0453] Depend on Fig.17 The results show that product ions of PSiYGA2 are mainly detected near m / z=243, 334, 410, 486, 514, 609, 758, 776, 835, 924, and 941.
[0454] m / z = 243 corresponds to the product ion C derived from carbazole phenyl group 18 H 13 N ·+ m / z = 334 corresponds to the product ion C derived from the diphenylamino group of carbazole 24 H 18 N2 ·+ m / z = 410 corresponds to the product ion C derived from the triphenylamino group of carbazole 30 H 22 N2 ·+ m / z = 486 corresponds to the product ion C derived from the triphenylamino group of carbazole to which a phenyl group is added 36 H 26 N2 ·+ m / z = 514 corresponds to the product ion C of the carbazole triphenylamino group and phenyl group separated from PSiYGA2 36 H 26 N2Si ···+m / z = 609 corresponds to the product ion C of the carbazole triphenylamine group being separated from PSiYGA2 and adding water. 42 H 33 N2OS + m / z = 758 corresponds to the product ion C of the carbazole group and the phenyl group separated from PSiYGA2 54 H 40 N3Si ··+ m / z = 776 corresponds to the product ion C when the carbazole group and the phenyl group are separated from PSiYGA2 and water is added 54 H 42 N3S + m / z = 835 corresponds to the product ion C of the 9H-carbazole group separated from PSiYGA2 60 H 45 N3Si ·+ m / z = 924 corresponds to the product ion C of the phenyl group separated from PSiYGA2 66 H 48 N4Si ·+ m / z = 941 corresponds to the product ion C when the phenyl group is separated from PSiYGA2 and water is added 66 H 49 N4S + .
[0455] The above results mean that PSiYGA2 has a carbazole skeleton and a benzene skeleton. Note that it is possible to detect ±1 of the product ion as a proton addition or desorption product.
[0456] As described above, when Q in the general formula (G1) is silicon, one of its characteristics is that water is added to the ions released from the first partial structure or the second partial structure (aryl group) bonded to silicon, thereby detecting the m / z of the product ions corresponding to the formation of a silanol group (SiOH). Example 2
[0457] (Synthesis Example 2) In this example, the results of various measurements of synthesized 4,4'(propane-2,2-diyl)bis{N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylaniline} (abbreviation: YGABmP) (structural formula (114)) are shown.
[0458] [Chemical formula 25]
[0459] (Synthesis Method of YGABmP) 2.2 g (5.0 mmol) of 4,4'(propane-2,2-diyl)bis(iodobenzene), 3.5 g (11 mmol) of N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylaniline, 4.0 g (40 mmol) of sodium tert-butoxide (abbreviated as tBuONa) and 0.2 mg (0.4 mmol) of bis(dibenzylideneacetone)palladium(0) (abbreviated as Pd(dba)2) were placed in a 100 mL three-necked flask, and the air in the flask was replaced with nitrogen. 20 mL of dehydrated xylene was added to the mixture. After the mixture was degassed while being stirred under reduced pressure, 0.8 mL (0.4 mmol) of tri(tert-butyl)phosphine (abbreviated as (tBu)3P) (10 wt% hexane solution) was added to the mixture. The mixture was heated and stirred at 120°C for 6 hours under a nitrogen stream to induce a reaction. After the reaction, 150 mL of toluene was added to the reaction mixture, and the suspension was filtered through magnesium silicate and diatomaceous earth. The filtrate obtained was concentrated, and the solid was purified by silica gel column chromatography (developing solvent was a mixture of toluene and hexane) and recrystallized to obtain a white powder of the target product with a yield of 70% and an output of 2.1 g. The following (b-1) shows the reaction scheme.
[0460] [Chemical formula 26]
[0461] The Rf values in silica gel thin layer chromatography (TLC) (developing solvent: ethyl acetate: hexane = 1:10) were as follows: the target product was 0.24, 4,4'-(propane-2,2-diyl)bis(iodobenzene) was 0.73, and N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylaniline was 0.20.
[0462] Fig.18 The obtained organic compound 1 H NMR spectrum. 1 H NMR measurement results: From these results, it was confirmed that the target YGABmP was obtained.
[0463] 1 H NMR (CDCl3, 300MHz): δ (ppm) = 2.81 (s, 6H), 7.04-7.44 (m, 38H), 8.13 (d, J = 7.8Hz, 4H).
[0464] Next, the YGABmP obtained in this example was subjected to LC / MS analysis.
[0465] Similar to Example 1, the MS / MS measurement of the exact mass (Exact Mass) of YGABmP at m / z 860.39 was performed using the PRM method. The PRM settings were: the mass range of the target ion was m / z 860.39±2.0 (isolation window=4); detection was performed in positive mode. The energy NCE (Normalized Collision Energy) for accelerating the target ion in the collision cell was set to 30 for measurement. Fig.19 Shown is an MS mass spectrum obtained by MS / MS measurement.
[0466] Depend on Fig.19 The results show that the product ions of YGABmP are mainly detected near m / z=451, 618, 680, 695, and 845.
[0467] m / z = 451 corresponds to the product ion C of carbazole diphenylamino group and phenyl group separated from YGABmP 33 H 27 N2 ··+ m / z = 618 corresponds to the product ion C of the carbazole group and the phenyl group separated from YGABmP 45 H 36 N3 ··+ m / z = 680 corresponds to the product ion C of the carbazole group and methyl group separated from YGABmP 50 H 38 N3 ··+ m / z = 695 corresponds to the product ion C of the carbazole group released from YGABmP 51 H 41 N3 ·+ m / z = 845 corresponds to the product ion C of the methyl group separated from YGABmP 62 H 45 N4 + .
[0468] The above results mean that YGABmP has a carbazole skeleton and a benzene skeleton. Note that it is possible to detect ±1 of the product ion as a proton addition or detachment. As described above, when Q in the general formula (G1) is carbon, one of its characteristics is to detect the m / z of the product ion corresponding to the detachment of the first partial structure or the second partial structure (aryl group) bonded to the carbon.
[0469] Next, the T values of PSiYGA2, the synthesis method of which was described in Example 1, YGABmP, the synthesis method of which was described in this example, and the comparative compound are shown. gand the measurement results of the emission spectrum. As comparative compounds, N-(4-biphenyl)-4-(carbazole-9-yl)phenylaniline (abbreviated as YGA1BP) and N,N'-bis[4-(carbazole-9-yl)phenyl]-N,N'-diphenylbiphenyl-4,4'-diamine (abbreviated as YGABP), which are compounds without σ bonds, are used as units used in common with PSiYGA2 and YGABmP. The chemical formulas of PSiYGA2, YGABmP, YGA1BP, and YGABP and unit A, which is a unit common to the above compounds, are shown below.
[0470] [Chemical formula 27]
[0471] Furthermore, the emission spectrum in a benzene solution of each compound was measured using a fluorescence spectrophotometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd., Japan). Fig. 20 The emission spectra of PSiYGA2, YGABmP, YGA1BP and YGABP in toluene solution are shown. In addition, a tangent line is drawn at the maximum value of the slope on the short wavelength side of the peak in each emission spectrum, and the energy of the wavelength (light-emitting end) of the intersection of the tangent line and the horizontal axis (wavelength) or the baseline is set as the S1 energy level.
[0472] In addition, the T g The measurement was performed using a differential scanning calorimeter (DSC, Pyris 1DSC or DSC8500 manufactured by PerkinElmer, Inc.). For PSiYGA2, the sample powder was first heated to 370°C (above the melting point) and then cooled to below -5°C at a rate of 50°C / min or more. T was then read from the DSC spectrum obtained by heating to 370°C at a rate of 40°C / min. g . T for other compounds g Measure in the same way.
[0473] The following table shows the peak wavelength read from the emission spectrum, the emission end on the short wavelength side, the S1 level calculated from the emission end, and the T g The measurement results.
[0474] [Table 1] Peak wavelength(nm) Light emitting end (nm) <![CDATA[Energy level of S1 (eV)]]> <![CDATA[T g (℃)]]> PSiYGA2 373 350 3.54 144 YGAB 375 350 3.54 140 YGA1BP 388 362 3.43 82 YGAB 400,420 382 3.25 144
[0475] according to Fig. 20 As can be seen from the above table, the peak wavelength and the wavelength of the light-emitting end on the short wavelength side of PSiYGA2 and YGABmP are shorter than those of YGA1BP.
[0476] As can be seen from the above table, compared with YGA1BP and YGABP, the S1 energy level of PSiYGA2 and YGABmP is higher. This is because they have the following structures: PSiYGA2 and YGABmP have a structure in which two units A are bonded through a σ bond; while YGA1BP has a structure in which a phenyl group is directly bonded to unit A; YGABP has a structure in which two units A are directly bonded.
[0477] In addition, as can be seen from the above table, the T of PSiYGA2 and YGABmP g is very high, above 140 °C, equivalent to YGABP and significantly higher than the value of YGA1BP. It can be said that this is because, like YGABP, PSiYGA2 and YGABmP have two units A, and thus the molecular weight is sufficiently high.
[0478] From the above results, it can be seen that PSiYGA2 and YGABmP of one embodiment of the present invention are materials having a high S1 energy level and a high T g . Example 3
[0479] (Synthesis Example 3) In this embodiment, the results of various measurements are shown for the synthesis of diphenyl-bis{4-[3-(9-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}silane (abbreviation: PCCz2PSi), an organic compound of one embodiment of the present invention (structural formula (101)). The structure of PCCz2PSi is shown below.
[0480] [Chemical formula 28]
[0481] <Synthesis of PCCz2PSi> 0.44 g (0.89 mmol) of bis(4-bromophenyl)-diphenylsilane, 0.73 g (1.8 mmol) of 3-(9-phenyl-9H-carbazole-3-yl)-9H-carbazole, and 0.74 g (5.4 mmol) of potassium carbonate (abbreviated as K2CO3) were placed in a 50 mL three-necked flask. 9.0 mL of dehydrated xylene was added to the mixture, and the mixture was stirred under reduced pressure for degassing. 4.0 mg (18 μmol) of palladium acetate (abbreviated as Pd(OAc)2) and 18 mg (89 μmol) of tri-tert-butylphosphine (abbreviated as P(tBu)3) were added to the above mixture, and the mixture was stirred at 140°C for 10 hours under a nitrogen stream. After stirring, the mixture was cooled to room temperature. The mixture was extracted with toluene. Then, the extracted solution was concentrated to obtain an oily substance. The oily substance was purified by silica gel column chromatography (developing solvent: hexane, followed by toluene:hexane=1:2). The obtained fractions were concentrated to obtain an oil. The oil was purified by high performance liquid chromatography (developing solvent: chloroform). The obtained fractions were concentrated to obtain an oil. Hexane was added to the oil and ultrasonic waves were irradiated. The precipitated solid was filtered out by suction to obtain the target white solid (0.66 g, yield 65%). The following formula (b-1) shows the synthesis scheme of PCCz2PSi.
[0482] [Chemical formula 29]
[0483] 0.66 g of the obtained white solid was purified by sublimation using a gradient sublimation method. The sublimation purification was carried out under the conditions of an argon flow rate of 5 mL / min, a pressure of 3.2 Pa, and a heating temperature of 455° C. for 17 hours. As a result, a white solid of the target substance (0.38 g, a recovery rate of 58%) was obtained.
[0484] Fig.21 The organic compounds obtained by sublimation purification are shown 1 H NMR spectrum. 1 HNMR measurement results: From these results, it was confirmed that PCCz2PSi was obtained.
[0485] 1 H NMR (CDCl3, 300MHz): δ=8.46 (s, 4H), 8.24 (d, J=6.3Hz, 4H), 7.94 (d, J=7.8Hz, 4H), 7.81-7.72 (m, 12H), 7.66-7.40 (m, 28H), 7.36-7.29 (m, 4H).
[0486] Next, the T values of PCCz2PSi and comparative compounds whose synthesis methods are shown in this example are shown. gAnd the measurement results of the emission spectrum. As a comparative compound, 9,9'-diphenyl-9H,9'H-3,3'-bicarbazole (abbreviated as: PCCP) including a compound having a unit used in common with PCCz2PSi but without a σ bond was prepared. The chemical formula of unit B which is a unit common to PCCz2PSi and PCCP and the above compounds is shown below.
[0487] [Chemical formula 30]
[0488] Furthermore, the emission spectrum in a benzene solution of each compound was measured using a fluorescence spectrophotometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd., Japan). Fig. 22 The emission spectrum is shown. The S1 level of each compound was calculated in the same manner as in Example 2. In addition, the T g The following table shows the peak wavelength read from the emission spectrum, the emission end on the short wavelength side, the S1 level calculated from the emission end, and the T of each compound. g The measurement results.
[0489] [Table 2] Peak wavelength(nm) Light emitting end (nm) <![CDATA[Energy level of S1 (eV)]]> <![CDATA[T g (℃)]]> PZT 390,407 369 3.36 193 PCCP 390,407 369 3.36 101
[0490] according to Fig. 22 From the above table, it can be seen that the emission spectra of PCCz2PSi and PCCP overlap, and the peak wavelength, the luminescent end on the short wavelength side and the degree of S1 energy level are almost the same.
[0491] In addition, according to the above table, the T of PCCz2PSi g The value of is high, being 190° C. or higher, and is significantly higher than that of PCCP. This is probably because the molecular weight becomes sufficiently high due to the structure in which two units B are bonded via a σ bond.
[0492] From the above results, it can be seen that PCCz2PSi of one embodiment of the present invention has a high S1 level and a high T g materials. Example 4
[0493] (Synthesis Example 4) In this example, the results of various measurements performed on 9,9"-[3,3'-(phenylsilyl)diphenyl]bis(3,9'-bi-9H-carbazole (abbreviated as mCzCz2PSi) (structural formula (102)), which is an organic compound of one embodiment of the present invention, are shown. The structure of mCzCz2PSi is shown below.
[0494] [Chemical formula 31]
[0495] 1.5 g (3.0 mmol) of bis(4-bromophenyl)diphenylsilane, 2.4 g (7.2 mmol) of 9H-3,9'-bicarbazole, 1.7 g (18 mmol) of sodium tert-butoxide, and 0.15 g (0.36 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (abbreviated as: SPhos) were placed in a 200 mL three-necked flask. 20 mL of xylene was added to the mixture, and the mixture was degassed by stirring under reduced pressure. 0.17 g (0.18 mmol) of tris(dibenzylideneacetone)dipalladium(0) was added to the mixture, and heated and stirred at 140°C for 7 hours under a nitrogen flow. After stirring, toluene was added to the mixture, and the mixture was filtered through magnesium silicate, diatomaceous earth, and alumina to obtain a filtrate. The obtained filtrate was concentrated to obtain a solid. The solid was purified by silica gel column chromatography (developing solvent: hexane: ethyl acetate = 9:1). The obtained solid was reprecipitated with ethyl acetate / ethanol to obtain 2.6 g of a white solid with a yield of 86%.
[0496] [Chemical formula 32]
[0497] 2.5 g of the obtained solid was sublimated and purified by gradient sublimation. The sublimation purification was performed under the conditions of a pressure of 3.8 Pa and an argon flow rate of 15 mL / min with heating at 380° C. After the sublimation purification, 2.2 g of a white solid was obtained at a recovery rate of 89%.
[0498] Fig.23 The organic compound obtained by sublimation purification is shown 1 H NMR spectrum. 1 HNMR measurement results: From the results, it was confirmed that mCzCz2PSi was obtained.
[0499] 1 H NMR (DMSO-d6, 300MHz): δ=7.19-7.41 (m, 18H), 7.55 (dd, J1=8.4Hz, J2=1.8Hz, 2H), 7. 51-7.58 (m, 8H), 7.70-7.95 (m, 12H), 8.26 (d, J1=7.5Hz, 6H), 8.48 (d, J1=2.4Hz, 2H).
[0500] Next, the mCzCz2PSi obtained in this example was subjected to LC / MS analysis.
[0501] Similar to Example 1, the MS / MS measurement of the exact mass (Exact Mass) of mCzCz2PSi at m / z 996.36 was performed using the PRM method. The PRM settings were: the mass range of the target ion was m / z 996.36±2.0 (isolation window=4); detection was performed in positive mode. The energy NCE (Normalized Collision Energy) for accelerating the target ion in the collision cell was set to 50 for measurement. Fig.24 Shown is an MS mass spectrum obtained by MS / MS measurement.
[0502] Depend on Fig.24 The results show that the product ions of mCzCz2PSi are mainly detected near m / z=364, 529, 607, 772, 831, 859, and 937.
[0503] m / z = 364 corresponds to the product ion C of carbazole, phenyl-bicarbazole and phenyl groups separated from mCzCz2PSi and added with water. 22 H 16 N4S ··+ m / z = 529 corresponds to the product ion C of the phenyl-bicarbazolyl group and the phenyl group being separated from mCzCz2PSi and adding water. 36 H 25 N2OS ··+ m / z = 607 corresponds to the product ion C of the phenyl-bicarbazolyl group being separated from mCzCz2PSi and adding water 42 H 31 N2OS ··+ m / z = 772 corresponds to the product ion C of the carbazole group and phenyl group being separated from mCzCz2PSi and adding water 42 H 31 N2OS + m / z = 831 corresponds to the product ion C of the carbazole group being separated from mCzCz2PSi and adding water 60 H 41 N3Si ·+ m / z = 859 corresponds to the product ion C of two phenyl groups separated from mCzCz2PSi and added with water 60 H 39 N4S + m / z = 937 corresponds to the product ion C when the phenyl group is separated from mCzCz2PSi and water is added 66 H 45 N4S + .
[0504] The above results mean that mCzCz2PSi has a carbazole skeleton and a benzene skeleton. Note that it is possible to detect ±1 of the product ion as a proton addition or desorption product.
[0505] As described above, when Q in the general formula (G1) is silicon, one of its characteristics is that water is added to the ions released from the first partial structure or the second partial structure (aryl group) bonded to silicon, thereby detecting the m / z of the product ions corresponding to the formation of a silanol group (SiOH).
[0506] then, Fig.25 The absorption spectrum and emission spectrum of mCzCz2PSi in toluene solution are shown. The absorption spectrum in toluene solution was measured using an ultraviolet-visible spectrophotometer (V-770DS manufactured by JASCO Corporation), and its absorption spectrum shows the spectrum obtained by subtracting the spectrum measured by placing only toluene in a quartz dish. Fig.26 The absorption spectrum and emission spectrum of the film are shown. The solid film was manufactured on a quartz substrate by vacuum evaporation. In addition, the absorption spectrum of the film was measured using a spectrophotometer (spectrophotometer U4100 manufactured by Hitachi High-Technologies Corporation). In addition, the emission spectrum was measured using a fluorescence spectrophotometer (FP-8600 manufactured by JASCO Corporation).
[0507] exist Fig.25 The toluene solution of mCzCz2PSi has absorption peaks at 342nm, 330nm, 305nm, and 294nm and has emission wavelength peaks at 372nm and 387nm (excitation wavelength 330nm). Fig.26 In the film, absorption peaks were observed at 343nm and 294nm, and emission wavelength peaks were observed at 382nm and 392nm (excitation wavelength 300nm).
[0508] The T values of mCzCz2PSi, the synthesis method of which is shown in this example, and 9-[3-(triphenylsilyl)phenyl]-3,9'-bi-9H-carbazole (abbreviated as PSiCzCz) including a unit used in conjunction with mCzCz2PSi are shown. g The chemical formulas of mCzCz2PSi and PSiCzCz and the unit C which is a unit common to the above compounds are shown below.
[0509] [Chemical formula 33]
[0510] Fig. 27The emission spectrum of each compound in a benzene solution measured using a fluorescence photometer (FP-8600 manufactured by JASCO Corporation) is shown. Note that a tangent line is drawn at the value where the inclination on the short wavelength side of the peak in each emission spectrum is the largest, and the energy of the wavelength (light-emitting end) of the intersection of the tangent line and the horizontal axis (wavelength) or the baseline is set as the S1 level.
[0511] Furthermore, the emission spectrum of the thin film of each compound was measured at 10 K. Specifically, the phosphorescence spectrum was measured by irradiating excitation light (325 nm) and then detecting the light emission after 0.02 seconds. Fig.28 The emission spectrum (phosphorescence spectrum) is shown. Note that a tangent line is drawn at the value where the slope on the short wavelength side of the peak in each emission spectrum (phosphorescence spectrum) is the largest, and the energy of the wavelength (light-emitting end) of the intersection of the tangent line and the horizontal axis (wavelength) or the baseline is set as the T1 energy level.
[0512] In addition, the T of each compound was measured in the same manner as in Example 2. g The following table shows the compounds, Fig. 27 The peak wavelength read from the emission spectrum, the emission end on the short wavelength side, the S1 level calculated from the emission end, and the Fig.28 The emission spectrum (phosphorescence spectrum) is read from the T1 energy level and T g The measurement results.
[0513] [Table 3] Peak wavelength (nm) Light emitting end (nm) <![CDATA[Energy level of S1 (eV)]]> <![CDATA[Energy level of T1 (eV)]]> <![CDATA[T g (℃)]]> mxDV 372 356 3.48 3.0 166 PcqI 371 356 3.48 3.0 115
[0514] according to Fig. 27 From the above table, it can be seen that the fluorescence emission spectra of mCzCz2PSi and PSiCzCz overlap, and the peak wavelength, the emission end on the short wavelength side and the degree of S1 energy level are almost the same.
[0515] In addition, according to the above table, we can know that the T of mCzCz2PSi g The value of is high, being 160°C or higher, and is significantly higher than that of PSiCzCz. This is probably because the molecular weight is sufficiently higher than that of PSiCzCz having only one C unit, due to the structure in which two C units are bonded via a σ bond.
[0516] In addition, by Fig.28 As can be seen from the table above, the rising (starting) energy on the short wavelength side of the emission spectra (phosphorescence spectra) of mCzCz2PSi and PSiCzCz is 3.0 eV. In addition, the emission spectra also roughly overlap. It can be said that the T1 energy levels of mCzCz2PSi and PSiCzCz are almost the same. Note that the spectrum observed around 370nm to 420nm is derived from fluorescence.
[0517] From the above results, it can be seen that mCzCz2PSi of one embodiment of the present invention has high S1 level and T1 level and high T g In addition, from the results of Examples 2 to 4, it can be seen that the organic compound of one embodiment of the present invention has high S1 level and T1 level and high T g materials.
[0518] Since the organic compound of one embodiment of the present invention has g The temperature is very high, 100°C, so the light-emitting device containing the organic compound can show good characteristics even when stored or driven at high temperatures. In addition, even if the layer containing the organic compound is subjected to high-temperature treatment in the processing step when manufacturing the light-emitting device, good film quality can be maintained, so a light-emitting device with good characteristics can be manufactured. Example 5
[0519] In this embodiment, the light emitting device 1 and the comparative light emitting device 2, which are blue fluorescent light emitting devices made of PSiYGA2, an organic compound of one embodiment of the present invention, are manufactured and various measurements are performed on these light emitting devices. The structural formulas of the organic compounds used for the light emitting device 1 and the comparative light emitting device 2 are shown below. In addition, the device structures of the light emitting device 1 and the comparative light emitting device 2 are shown in the table below.
[0520] [Chemical formula 34]
[0521] [Table 4]
[0522] <<Manufacturing of Light Emitting Device 1>> The light-emitting device 1 shown in this embodiment has the following structure: a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer (a first electron transport layer and a second electron transport layer) and an electron injection layer are stacked in sequence on a first electrode formed on a substrate, and a second electrode is stacked on the electron injection layer.
[0523] First, the first electrode is formed on the substrate. The electrode area is 4mm 2 (2 mm×2 mm). In addition, a glass substrate was used as the substrate. In addition, indium tin oxide containing silicon oxide (ITSO) was deposited by a sputtering method to a thickness of 110 nm to form a first electrode. Note that in this embodiment, the first electrode is used as an anode.
[0524] Here, as a pretreatment, the surface of the substrate was washed with water, baked at 200°C for 1 hour, and then subjected to UV ozone treatment for 370 seconds. Then, the substrate was placed inside the chamber and the pressure was reduced to 1×10 -4Pa in a vacuum deposition apparatus and in a heating chamber in the vacuum deposition apparatus, vacuum baking is performed at 170° C. for 30 minutes, and then the substrate is cooled for about 30 minutes.
[0525] Next, a hole injection layer was formed on the first electrode by co-evaporating 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as: NPB) and molybdenum oxide (MoO3) to a thickness of 50 nm and a weight ratio of 4:1 (=NPB:MoO3).
[0526] Next, a hole transport layer was formed on the hole injection layer by evaporating PSiYGA2 to a thickness of 10 nm.
[0527] Next, a light-emitting layer was formed on the hole transport layer. 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as CzPA) and N,N'-bis[4-(9H-carbazole-9-yl)phenyl]-N,N'-diphenyl-4,4'-styrene diamine (abbreviated as YGA2S) were co-evaporated at a weight ratio of 1:0.05 (=CzPA:YGA2S) to form a light-emitting layer with a thickness of 30 nm.
[0528] Next, an electron transport layer was formed on the light emitting layer. As the first electron transport layer, tris(8-hydroxyquinoline)aluminum(III) (abbreviated as Alq3) was formed to a thickness of 10 nm, and as the second electron transport layer, bathophenanthroline (abbreviated as Bphen) was formed to a thickness of 20 nm.
[0529] Next, an electron injection layer was formed on the electron transport layer. The electron injection layer was formed by evaporating lithium fluoride (LiF) to a thickness of 1 nm.
[0530] Next, a second electrode was formed on the electron injection layer. Aluminum (Al) was deposited to a thickness of 200 nm to form the second electrode. In this embodiment, the second electrode was used as a cathode.
[0531] The light emitting device 1 is manufactured through the above-mentioned steps. Next, a method for manufacturing the comparative light emitting device 2 will be described.
[0532] <<Manufacturing of Comparative Light Emitting Device 2>> The comparative light-emitting device 2 is a light-emitting device manufactured in the same manner as the light-emitting device 1 except that PSiYGA2 used for the hole transport layer in the light-emitting device 1 is replaced with YGABP.
[0533] In a glove box with a nitrogen atmosphere, the light-emitting device 1 and the comparative light-emitting device 2 were sealed using a glass substrate in a manner that did not expose them to the atmosphere (a sealant was applied around the device, UV treatment was performed during sealing, and heat treatment was performed at 80°C for 1 hour), and then the initial characteristics of each light-emitting device were measured.
[0534] Fig.29 The luminance-current density characteristics of the light emitting device 1 and the comparative light emitting device 2 are shown. Fig.30 The current efficiency-brightness characteristics are shown. Fig.31 The power efficiency-brightness characteristics are shown. Fig.32 The external quantum efficiency-brightness characteristics are shown. Fig.33 Shown at 2.5 mA / cm 2 Electroemission spectroscopy measured at current densities of 200 Å.
[0535] In addition, the following table shows the brightness of the light emitting device 1 and the co...
Claims
1. An organic compound represented by the general formula (G1): in, Q represents carbon or silicon, R 1 and R 2 each independently represents an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 8 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, n represents an integer greater than or equal to 1 and less than or equal to 3, α 1 To α 4 each independently represents a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group, R 15 , R 25 , R 31 , R 45 , R 55 and R 61 At least one of represents a single bond, Other R 15 , R 25 , R 31 , R 45 , R 55 and R 61 Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, R 11 To R 14 , R 21 To R 24 , R 32 To R 35 , R 41 To R 44 , R 51 To R 54 and R 62 To R 65 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 8 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, In R 15 When it is a single bond, R 15 With α 2 Bonded to form a ring, In R 45 When it is a single bond, R 45 With α 4 bonded to form a ring, In R 25 and R 31 When both are single bonds, R 25 and R 31 bonded to each other to form a ring, In R 55 and R 61 When both are single bonds, R 55 and R 61 bonded to each other to form a ring, In R 25 and R 31 is a single bond and R 25 and R 31 When the other of is hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, α 2 is a substituted or unsubstituted biphenylene group and is combined with R 25 and R 31 One of them is bonded to form a ring, And, in R 55 and R 61 is a single bond and R 55 and R 61 When the other of is hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, α 4 is a substituted or unsubstituted biphenylene group and is combined with R 55 and R 61 One of them is bonded to form a ring.
2. The organic compound according to claim 1, where α 1 and α 3 Each independently represents a substituted or unsubstituted meta-phenylene.
3. The organic compound according to claim 1, The organic compound is represented by the general formula (G2-1): Q represents carbon or silicon, R 1 and R 2 each independently represents an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 8 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, n represents an integer greater than or equal to 1 and less than or equal to 3, And R 11 To R 14 , R 21 To R 24 , R 32 To R 35 , R 41 To R 44 , R 51 To R 54 , R 62 To R 65 , R 71 To R 74 , R 81 To R 84 , R 91 To R 93 and R 101 To R 103 Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
4. The organic compound according to claim 1, The organic compound is represented by the general formula (G1-2-2): Q represents carbon or silicon, R 1 and R 2 each independently represents an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 8 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, n represents an integer greater than or equal to 1 and less than or equal to 3, α 1 To α 4 each independently represents a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group, And R 11 To R 15 , R 21 To R 24 , R 32 To R 35 , R 41 To R 45 , R 51 To R 54 and R 62 To R 65 Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
5. The organic compound according to claim 1, The organic compound is represented by the general formula (G2-3): Q represents carbon or silicon, R 1 and R 2 each independently represents an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 8 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, n represents an integer greater than or equal to 1 and less than or equal to 3, α 1 and α 3 each independently represents a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group, And R 11 To R 14 , R 21 To R 25 , R 32 To R 35 , R 41 To R 44 , R 51 To R 55 , R 62 To R 65 , R 91 To R 96 and R 101 To R 106 Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
6. The organic compound according to claim 1, The glass transition temperature of the organic compound is above 100°C.
7. The organic compound according to claim 1, The organic compound is represented by any one of structural formula (100), structural formula (101), structural formula (102), and structural formula (114):
8. A light emitting device, comprising: a first electrode; a second electrode; as well as Organic compound layer, The organic compound layer is located between the first electrode and the second electrode, and the organic compound layer includes the organic compound according to claim 1 .
9. A light emitting device, comprising: a first electrode; a second electrode; as well as Organic compound layer, wherein the organic compound layer is located between the first electrode and the second electrode, The organic compound layer includes a plurality of layers containing organic compounds and includes at least one light-emitting layer, Furthermore, among the plurality of layers containing the organic compound, any one of the layer in contact with the first electrode to at least the light-emitting layer contains the organic compound according to claim 1 .
10. A light emitting device, comprising: a first electrode; a second electrode; as well as Organic compound layer, wherein the organic compound layer is located between the first electrode and the second electrode, The organic compound layer includes a plurality of layers containing organic compounds and includes at least one light-emitting layer, The light-emitting layer comprises the organic compound according to claim 1 and a second organic compound, wherein the second organic compound has a π-electron-deficient heteroaromatic ring.
11. A light emitting device, comprising: The light emitting device according to claim 8; as well as transistor or substrate.
12. An electronic device comprising: The light emitting device according to claim 11; as well as Detection unit, input unit or communication unit.
13. A lighting device, comprising: The light emitting device according to claim 11; as well as shell.
Citation Information
Patent Citations
Carbazole derivative, and light-emitting element, light-emitting device and electronic equipment using the same
JP2009298767A