Light-emitting device material and light-emitting device

Abstract

To provide an organic compound with high heat resistance, and a novel organic compound that can be used for a light-emitting device that emits red light or near-infrared light.SOLUTION: An organic compound is represented by General Formula (G0). In General Formula (G0), Q represents oxygen or sulfur, Ar1 represents a substituted or unsubstituted fused aromatic ring, R1 and R2 each independently represent hydrogen or a group with 1 to 100 carbon atoms in total, and at least one of R1 and R2 has a hole-transport skeleton or a fused ring.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] One embodiment of the present invention is a method for producing an organic compound, a material for a light-emitting device (also referred to as a material for a light-emitting element), a light-emitting element, and a light-emitting device. devices (also called light-emitting elements), light-emitting devices, light-emitting modules, electronic devices, and lighting devices Regarding.

[0002] Note that one embodiment of the present invention is not limited to the above technical field. Examples of the semiconductor device include a semiconductor device, a display device, a light-emitting device, a power storage device, a memory device, an electronic device, a lighting device, Input devices (e.g., touch sensors), input / output devices (e.g., touch panels), etc. These driving methods or manufacturing methods can be cited as examples. [Background technology]

[0003] Organic electroluminescence (EL) Research and development of light-emitting devices using electrons (also called organic EL devices or organic EL elements) is thriving. The basic structure of an organic EL device is a pair of electrodes with a light-emitting organic compound The organic EL device has a layer containing a compound (hereinafter referred to as the light-emitting layer) sandwiched between the layers. By applying pressure, light can be emitted from the light-emitting organic compound.

[0004] Examples of luminescent organic compounds include compounds that convert a singlet excited state into luminescence (fluorescent compounds, also called fluorescent materials), and compounds that convert the triplet excited state into luminescence (phosphorescent compounds In Patent Document 1, examples of phosphorescent compounds include iridium Organometallic complexes having the above as central metals have been disclosed.

[0005] When a phosphorescent compound is used to form an emitting layer of a light-emitting device, concentration quenching of the phosphorescent compound and To suppress triplet-triplet annihilation quenching, the compound is placed in a matrix of other compounds. It is often formed so that the phosphorescent compound is dispersed. The compound dispersed in the matrix, such as a phosphorescent compound, is called the guest material. Called.

[0006] When a phosphorescent compound is used as a guest material, the properties required for the host material are The triplet excited energy (energy difference between the ground state and the triplet excited state) is larger than that of It is to have.

[0007] In addition, the singlet excitation energy (energy difference between the ground state and the singlet excited state) is Since the triplet excitation energy is larger than the excitation energy, a material with a large triplet excitation energy has a large singlet excitation energy. Therefore, the large triplet excitation energy as described above is The material having the above structure is also useful in a light-emitting device using a fluorescent compound as a light-emitting material. do.

[0008] Organic EL devices are easy to make thin and lightweight, and can respond quickly to input signals. It has features such as the ability to be driven by a low-voltage DC power supply, making it suitable for use in display devices.

[0009] In addition, organic EL devices can be formed into a film, making it possible to obtain surface light emission. Therefore, a large-area light-emitting device can be easily formed. This is a characteristic that is difficult to obtain with point light sources such as ED (light emitting diodes) and linear light sources such as fluorescent lamps. Because the organic EL device is a color, it can also be used as a surface light source for lighting equipment, etc. expensive.

[0010] In addition, image sensors are used in a variety of applications, including personal authentication, defect analysis, medical diagnosis, and security-related applications. Image sensors use different wavelengths of light sources depending on the application. Image sensors detect light from a wide range of wavelengths, including visible light, short wavelength light such as X-rays, and near-infrared light. Light of various wavelengths is used, including light of long wavelengths.

[0011] Light-emitting devices are used as light sources for the image sensors mentioned above, as well as for display devices and lighting devices. Applications of this technology are also being considered. [Prior art documents] [Patent documents]

[0012] [Patent Document 1] Japanese Patent Application Laid-Open No. 2007-137872 Summary of the Invention [Problem to be solved by the invention]

[0013] An object of one embodiment of the present invention is to provide a novel organic compound. An object of one embodiment of the present invention is to provide an organic compound having high heat resistance. One aspect of the present invention is to provide a novel organic compound that can be used in a light-emitting device. Another embodiment of the present invention is a light-emitting device that emits red light or near-infrared light. Another object of the present invention is to provide a novel organic compound that can be used for the above-mentioned purposes. One advantageous embodiment is that the compound is used as a host material in a light-emitting device to disperse a light-emitting material. One of the objects of the present invention is to provide a novel organic compound that can be used in the above-described manner.

[0014] Another object of one embodiment of the present invention is to provide a light-emitting device with high emission efficiency. Another object of one embodiment of the present invention is to provide a light-emitting device with low driving voltage. Another object of one embodiment of the present invention is to provide a light-emitting device with a long lifetime. Another object of one embodiment of the present invention is to provide a light-emitting device with high heat resistance. Alternatively, one aspect of the present invention is a novel light-emitting device that emits red light or near-infrared light. One of our goals is to provide a

[0015] Note that the description of these problems does not preclude the existence of other problems. It is not necessary to solve all of these problems. From the description of the section, it is possible to extract other issues. [Means for solving the problem]

[0016] One embodiment of the present invention is an organic compound represented by General Formula (G0).

[0017] [ka]

[0018] In the general formula (G0), Q represents oxygen or sulfur, and Ar 1 is a substituted or unsubstituted condensed represents an aromatic ring, and R 1 and R 2 are each independently hydrogen or a group having a total of 1 to 100 carbon atoms. represents a group of R 1 and R 2 At least one of them has a skeleton with hole transport properties.

[0019] Another embodiment of the present invention is an organic compound represented by General Formula (G0).

[0020] [ka]

[0021] In the general formula (G0), Q represents oxygen or sulfur, and Ar 1 is a substituted or unsubstituted naphthyl group. A phenanthrene ring, a substituted or unsubstituted phenanthrene ring, and a substituted or unsubstituted chrysene represents one of the rings, and R 1 and R 2 are each independently hydrogen or a group having a total of 1 or more carbon atoms. represents a group of 100 or less, and R 1 and R 2 At least one of the above has a hole transporting skeleton. .

[0022] The hole transporting skeleton is a substituted or unsubstituted diarylamino group, a substituted or unsubstituted Any of fused aromatic hydrocarbon rings and substituted or unsubstituted π-excessive fused heteroaromatic rings It is preferable that it is one of them.

[0023] Another embodiment of the present invention is an organic compound represented by General Formula (G0).

[0024] [ka]

[0025] In the general formula (G0), Q represents oxygen or sulfur, and Ar 1 is a substituted or unsubstituted condensed represents an aromatic ring, and R 1 and R 2 are each independently hydrogen or a group having a total of 1 to 100 carbon atoms. represents a group of R 1 and R 2 At least one of the groups has a fused ring.

[0026] Another embodiment of the present invention is an organic compound represented by General Formula (G0).

[0027] [ka]

[0028] In the general formula (G0), Q represents oxygen or sulfur, and Ar 1 is a substituted or unsubstituted naphthyl group. A phenanthrene ring, a substituted or unsubstituted phenanthrene ring, and a substituted or unsubstituted chrysene represents one of the rings, and R 1 and R 2 are each independently hydrogen or a group having a total of 1 or more carbon atoms. represents a group of 100 or less, and R 1 and R 2 At least one of the groups has a fused ring.

[0029] The fused rings include substituted or unsubstituted fused aromatic hydrocarbon rings and substituted or unsubstituted π-perfluoroalkyl groups. Preferably, it is any one of the polycyclic condensed heteroaromatic rings.

[0030] The fused ring is a dibenzothiophene skeleton, a dibenzofuran skeleton, or a carbazole skeleton. It is preferably a substituted or unsubstituted fused heteroaromatic ring having any one of the above.

[0031] The fused rings include a naphthalene skeleton, a fluorene skeleton, a triphenylene skeleton, and a phenanthrene skeleton. A substituted or unsubstituted fused aromatic hydrocarbon ring having one of the following skeletons: is preferred.

[0032] Another embodiment of the present invention is an organic compound represented by General Formula (G0).

[0033] [ka]

[0034] In the general formula (G0), Q represents oxygen or sulfur, and Ar 1 is a substituted or unsubstituted condensed represents an aromatic ring, and R 1 and R 2 are each independently hydrogen or a group having a total of 1 to 100 carbon atoms. represents a group of R 1 and R 2 At least one of R has a hole transporting skeleton, 1 and R 2 At least one of the above represents a structure represented by general formula (u1). In general formula (u1), α represents represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, and n is 0 to 4 represents the integers, and A 1 represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and represents any one of substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms; , * represents a bond in general formula (G0).

[0035] Another embodiment of the present invention is an organic compound represented by General Formula (G0).

[0036] [ka]

[0037] In the general formula (G0), Q represents oxygen or sulfur, and Ar 1 is a substituted or unsubstituted naphthyl group. A phenanthrene ring, a substituted or unsubstituted phenanthrene ring, and a substituted or unsubstituted chrysene represents one of the rings, and R 1 and R 2 are each independently hydrogen or a group having a total of 1 or more carbon atoms. represents a group of 100 or less, and R 1 and R 2 at least one of the groups has a hole transporting skeleton, R1 and R 2 At least one of the above represents a structure represented by general formula (u1). In the formula (I), α represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, and n represents represents an integer between 0 and 4, and A 1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms. represents one of the above, and * represents a bonding site in general formula (G0).

[0038] In general formula (u1), A 1 is represented by the general formula (A 1 -1) to general formula (A 1 -17) It is preferred that

[0039] [ka]

[0040] General formula (A 1 -1) to general formula (A 1 -17) Medium, R A1 ~R A11 are each independently , hydrogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted Cycloalkyl groups having 3 to 7 carbon atoms, and substituted or unsubstituted cycloalkyl groups having 6 to 30 carbon atoms. represents any one of the aryl groups below.

[0041] In the general formula (u1), α represents any one of the general formulae (Ar-1) to (Ar-14). It is preferable to represent

[0042] [ka]

[0043] In general formula (Ar-1) to general formula (Ar-14), R B1 ~R B14 are each independently , hydrogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted Cycloalkyl groups having 3 to 7 carbon atoms, and substituted or unsubstituted cycloalkyl groups having 6 to 30 carbon atoms. represents any one of the aryl groups below.

[0044] In each of the organic compounds according to one embodiment of the present invention, in general formula (G0), Ar 1 is one It is preferable that the compound represents any one of general formulas (t1) to (t3).

[0045] [ka]

[0046] In general formula (t1) to general formula (t3), R 3 ~R 24 are each independently hydrogen, substituted or or unsubstituted alkyl groups having 1 to 6 carbon atoms; The following cycloalkyl groups and substituted or unsubstituted aryl groups having 6 to 30 carbon atoms: and * represents a bonding site in general formula (G0).

[0047] The organic compound of one embodiment of the present invention is preferably represented by general formula (G1).

[0048] [ka]

[0049] In the general formula (G1), Q represents oxygen or sulfur, and Ar 1 is a substituted or unsubstituted condensed Aromatic ring (or substituted or unsubstituted naphthalene ring, substituted or unsubstituted phenanthrene ring) R represents a substituted or unsubstituted chrysene ring; 1 and R 2 each independently represents hydrogen or a group having a total of 1 to 100 carbon atoms; R 1 and R 2 of At least one of them has a hole-transporting skeleton or fused ring.

[0050] The organic compound of one embodiment of the present invention is represented by any one of General Formulas (G1-1) to (G1-4). It is preferred that it is represented by unity.

[0051] [ka]

[0052] In the general formulae (G1-1) to (G1-4), Q represents oxygen or sulfur, and R 1 and R 2 each independently represents hydrogen or a group having a total of 1 to 100 carbon atoms; R 1 and R 2 At least one of R has a hole transporting skeleton or fused ring, 3 ~R 8 and R 17 ~ R 24 are each independently hydrogen or a substituted or unsubstituted alkyl having 1 to 6 carbon atoms. groups, substituted or unsubstituted cycloalkyl groups having 3 to 7 carbon atoms, and substituted or unsubstituted It represents any one of substituted aryl groups having 6 to 30 carbon atoms.

[0053] Alternatively, one embodiment of the present invention is a light-emitting compound having a furoquinoxaline skeleton to which a fused aromatic ring is fused. Alternatively, one aspect of the present invention is a material for a device. The light-emitting device material has a structure in which fused aromatic rings are fused. The device material is preferably a light-emitting device material that emits red or near-infrared light. The material for a light-emitting device according to one embodiment of the present invention is preferably a host material for a light-emitting device. The material for a light-emitting device according to one embodiment of the present invention is an electron transport material for a light-emitting device. It is preferable.

[0054] One embodiment of the present invention includes an organic compound or a material for a light-emitting device having any of the above structures. , a light-emitting device.

[0055] One embodiment of the present invention includes a layer containing an organic compound between a pair of electrodes, and the layer containing an organic compound is A light-emitting device having an organic compound or a material for a light-emitting device having any of the above structures. do.

[0056] One embodiment of the present invention includes a layer containing an organic compound between a pair of electrodes, and the layer containing an organic compound is The light-emitting layer has an organic compound or a material for a light-emitting device having any of the above structures. It is a light-emitting device having

[0057] One embodiment of the present invention includes a layer containing an organic compound between a pair of electrodes, and the layer containing an organic compound is The light-emitting layer and the electron transport layer are included, and at least one of the light-emitting layer and the electron transport layer is any one of the above. The organic compound or material for a light-emitting device may have any of the above structures.

[0058] One embodiment of the present invention is a light-emitting device having any of the above structures, and a light-emitting element including one of a transistor and a substrate. Alternatively, the light emitting device may have both of the above.

[0059] One embodiment of the present invention is a flexible printed circuit board (FPC) having the above-described light-emitting device. ble Printed Circuit (hereinafter referred to as FPC) or TCP (Ta Modules with connectors such as PE Carrier Package, or COG (Chip On Glass) or COF (Chip On Fi Light-emitting modules such as light-emitting modules that incorporate integrated circuits (ICs) using the lm method, etc. The light-emitting module according to one aspect of the present invention has only one of a connector and an IC. It may have either one or both.

[0060] One aspect of the present invention is a light-emitting device including the above-described light-emitting module, an antenna, a battery, a housing, a camera, a speaker, and the like. The electronic device has at least one of a speaker, a microphone, and an operation button.

[0061] One aspect of the present invention is a light-emitting device comprising at least one of a housing, a cover, and a support base. The lighting device has one and [Effects of the Invention]

[0062] According to one embodiment of the present invention, a novel organic compound can be provided. According to one embodiment of the present invention, an organic compound that can be used in a light-emitting device can be provided. According to one embodiment of the present invention, a novel organic compound capable of emitting red light or near-infrared light can be provided. The present invention provides a novel organic compound that can be used in a light-emitting device. In this way, they can be used as host materials to disperse luminescent materials in light-emitting devices. This provides a novel organic compound that can be used.

[0063] According to one embodiment of the present invention, a light-emitting device with high emission efficiency can be provided. According to one embodiment of the present invention, a light-emitting device with a low driving voltage can be provided. According to one embodiment of the present invention, a light-emitting device with high heat resistance can be provided. According to one aspect of the present invention, a novel light-emitting device that emits red or near-infrared light can be provided. We can provide it.

[0064] The description of these effects does not preclude the existence of other effects. However, it is not necessary to have all of these effects. , it is possible to extract effects other than these. [Brief explanation of the drawings]

[0065] [Figure 1] 1A, 1B, 1C, and 1D are cross-sectional views showing examples of light-emitting devices. [Figure 2] Fig. 2A is a top view showing an example of a light emitting device, and Fig. 2B and Fig. 2C are cross-sectional views showing an example of a light emitting device. [Figure 3] 3A and 3C are cross-sectional views showing an example of a light emitting apparatus, and Fig. 3B is a cross-sectional view showing an example of a light emitting device. [Figure 4] 4A and 4B are cross-sectional views showing an example of a light emitting device. [Figure 5] Fig. 5A is a top view showing an example of a light emitting device, Fig. 5B is a cross-sectional view showing an example of a light emitting device, Fig. 5C and Fig. 5D are cross-sectional views showing an example of a transistor. [Figure 6] 6A, 6B, 6C, and 6D are diagrams showing examples of electronic devices. [Figure 7] 7A, 7B, 7C, 7D, 7E, and 7F are diagrams showing examples of electronic devices. [Figure 8] Fig. 8A is a diagram showing an example of the exterior of a car, and Fig. 8B and Fig. 8C are diagrams showing an example of the interior of a car. [Figure 9] Figures 9A and 9C are diagrams showing an example of a biometric authentication device. Figure 9B is a diagram showing an example of a light source. Figure 9D is a diagram showing an example of a non-destructive testing device. Figure 9E is a diagram showing an example of a mobile phone. [Figure 10] FIG. 10 is a 1H-NMR chart of the organic compound represented by the structural formula (100). [Figure 11] 11A and 11B are the ultraviolet-visible absorption spectrum and the emission spectrum of the organic compound represented by the structural formula (100). [Figure 12] FIG. 12 is a cross-sectional view showing a light-emitting device according to an embodiment. [Figure 13] FIG. 13 is a graph showing the current density-luminance characteristics of the light-emitting device 1. As shown in FIG. [Figure 14] FIG. 14 is a graph showing the voltage-luminance characteristics of the light-emitting device 1. As shown in FIG. [Figure 15] FIG. 15 is a graph showing the luminance-current efficiency characteristics of the light-emitting device 1. [Figure 16] FIG. 16 is a diagram showing the voltage-current characteristics of the light-emitting device 1. As shown in FIG. [Figure 17] FIG. 17 is a graph showing the luminance-external quantum efficiency characteristics of the light-emitting device 1. As shown in FIG. [Figure 18] FIG. 18 is a diagram showing the emission spectrum of the light-emitting device 1. As shown in FIG. [Figure 19] FIG. 19 shows the results of a reliability test on the light-emitting device 1. As shown in FIG. [Figure 20] FIG. 20 is a graph showing the current density-luminance characteristics of light-emitting devices 2 and 3. [Figure 21] FIG. 21 is a diagram showing the voltage-luminance characteristics of the light-emitting devices 2 and 3. [Figure 22] FIG. 22 is a graph showing the luminance-current efficiency characteristics of light-emitting devices 2 and 3. [Figure 23] FIG. 23 is a diagram showing the voltage-current characteristics of the light-emitting devices 2 and 3. [Figure 24] FIG. 24 is a graph showing the luminance-external quantum efficiency characteristics of light-emitting devices 2 and 3. [Figure 25]FIG. 25 shows the emission spectra of light-emitting devices 2 and 3. [Figure 26] FIG. 26 shows the results of the reliability test of light-emitting devices 2 and 3. [Figure 27] FIG. 27 is a 1H-NMR chart of the organic compound represented by the structural formula (113). DETAILED DESCRIPTION OF THE INVENTION

[0066] The embodiments will be described in detail with reference to the drawings. However, the present invention is not limited to the following description. The present invention is not limited to the above embodiments, and various changes and modifications may be made in the form and details thereof without departing from the spirit and scope of the present invention. It will be readily understood by those skilled in the art that the present invention can be achieved by the following embodiments. It should not be construed as being limited to the contents described.

[0067] In the configuration of the invention described below, the same parts or parts having similar functions are The same reference numerals are used in common between different drawings, and repeated explanations thereof will be omitted. When referring to a function, the hatch pattern may be the same and no particular symbol may be assigned.

[0068] In addition, the position, size, range, etc. of each component shown in the drawings are not necessarily the same as in reality for ease of understanding. Therefore, the disclosed invention may not necessarily represent the position, size, range, etc. Furthermore, the present invention is not limited to the position, size, range, etc. disclosed in the drawings.

[0069] The words "film" and "layer" may be used interchangeably depending on the situation. For example, the term "conductive layer" can be replaced with "conductive film." Alternatively, for example, the term "insulating film" can be changed to The term can be changed to "insulating layer."

[0070] (Embodiment 1) In this embodiment, an organic compound of one embodiment of the present invention will be described.

[0071] [Structure of an organic compound according to one embodiment of the present invention] One aspect of the present invention is a compound having a fused aromatic ring in a furoquinoxaline skeleton or a thienoquinoxaline skeleton. The present invention also provides an organic compound having a condensed structure. Light-emitting device material having a structure in which a fused aromatic ring is fused to a thienoquinoxaline or thienoquinoxaline skeleton The material for a light-emitting device is particularly suitable for a light-emitting device that emits red or near-infrared light. The material for a light-emitting device is preferably a material for a light-emitting device. Preferably, the material is a resist material or an electron transporting material.

[0072] The quinoxaline skeleton is a structure in which a benzene ring is condensed with a pyrazine ring. By using a quinoxaline or thienoquinoxaline skeleton, it is possible to Compared with the case of using a thienopyrazine skeleton, the π-conjugated system is extended and the lowest unoccupied molecular orbital level (L The LUMO level can be deepened and made energetically stable. By deepening the electron density, the triplet excited level (T1 level) can be lowered. The quinoxaline or thienoquinoxaline skeleton is fused with a fused aromatic ring, Compared with the case where the condensed aromatic ring is not present or the case where a monocyclic aromatic ring is condensed, the π-conjugated system is It is possible to elongate the LUMO level, deepen it, and make it energetically stable. For these reasons, the organic compound of one embodiment of the present invention can be used to It can be suitably used in light-emitting devices with long wavelengths (for example, red to near-infrared).

[0073] Luminescent materials with long emission wavelengths tend to have low T1 levels and deep LUMO levels. Therefore, the organic compound of one embodiment of the present invention is preferably combined with a light-emitting substance that emits light at a long wavelength. It is preferable to use a light-emitting substance having a long wavelength as a guest material. By using the organic compound of one embodiment of the present invention as a host material, the emission efficiency of the light-emitting device can be improved. and the driving voltage can be reduced.

[0074] In addition, organic compounds having a pyrazine ring have a higher affinity for gas than organic compounds having a pyrimidine ring. The organic compound according to one embodiment of the present invention has a high glass transition temperature and high heat resistance. A quinoxaline skeleton or a thienoquinoxaline skeleton (i.e., a skeleton having a pyrazine ring) Because of the structure of fused aromatic rings, it has a furopyrimidine skeleton or a thienopyrimidine skeleton. In particular, compared to the structure in which the fused aromatic rings are fused, the heat resistance is high and the emission wavelength is long. It is an organic compound suitable for certain light-emitting devices.

[0075] Light-emitting devices used in high-temperature environments, such as those for automobiles, require high heat resistance. In addition, even when high temperatures are applied during the manufacturing process of the product, such as during the sealing process using glass frit, Light-emitting devices require high heat resistance. The material must have a glass transition temperature (Tg) of 100°C or higher, or even 120°C or higher. In one embodiment of the present invention, the Tg of the organic compound is 100° C. or higher, and Since the temperature can reach 120℃ or higher, it is suitable for light-emitting devices that require high heat resistance. Materials can be provided.

[0076] The organic compound according to one embodiment of the present invention can be used, for example, to disperse a light-emitting substance in a light-emitting device. It can be used as a host material.

[0077] Furthermore, the organic compound of one embodiment of the present invention has a high electron-transport property; therefore, in a light-emitting device, It can be used as an electron transporting material.

[0078] Specifically, one embodiment of the present invention is an organic compound represented by general formula (G0). Not only organic compounds having the structure represented by the following general formula, but also light-emitting device materials having the structure, Each of these is an aspect of the present invention.

[0079] [ka]

[0080] In the general formula (G0), Q represents oxygen or sulfur, and Ar 1 is a substituted or unsubstituted condensed represents an aromatic ring, and R 1 and R 2 are each independently hydrogen or a group having a total of 1 to 100 carbon atoms. represents a group of R 1 and R 2 At least one of them has a skeleton with hole transport properties.

[0081] Another embodiment of the present invention is an organic compound represented by General Formula (G0).

[0082] [ka]

[0083] In the general formula (G0), Q represents oxygen or sulfur, and Ar 1 is a substituted or unsubstituted naphthyl group. A phenanthrene ring, a substituted or unsubstituted phenanthrene ring, and a substituted or unsubstituted chrysene represents one of the rings, and R 1 and R 2 are each independently hydrogen or a group having a total of 1 or more carbon atoms. represents a group of 100 or less, and R 1 and R 2 At least one of the above has a hole transporting skeleton. .

[0084] R 1 and R 2 At least one of the hole transporting skeletons has a substituted or unsubstituted diamine. arylamino group, substituted or unsubstituted fused aromatic hydrocarbon ring, and substituted or unsubstituted Preferably, the aromatic ring is any one of the π-excess condensed heteroaromatic rings listed above.

[0085] The fused aromatic hydrocarbon ring includes a naphthalene skeleton, a fluorene skeleton, a triphenylene skeleton, and It is preferable that the compound has one of the phenanthrene skeletons.

[0086] The π-excessive fused heteroaromatic rings are dibenzothiophene skeletons, dibenzofuran skeletons, and carbazole skeletons. It is preferable that the aromatic ring is a condensed heteroaromatic ring having one of the dibenzobenzols. The thiophene skeleton provides a light-emitting device with a higher efficiency than the dibenzofuran or carbazole skeleton. The carbazole skeleton allows for the dibenzothiophene The luminous efficiency of light-emitting devices can be improved compared to that of the benzofuran or dibenzofuran skeletons. .

[0087] In this specification and the like, the fused heteroaromatic ring includes a carbazole ring, a dibenzothiophene ... Not only the benzofuran ring, but also the benzocarbazole ring, dibenzocarbazole ring, and indolocarbazole ring carbazole ring, benzoindolocarbazole ring, dibenzoindolocarbazole ring, benzoindolocarbazole ring, Zindolobenzocarbazole ring, benzonaphthothiophene ring, benzonaphthofuran ring As shown in the figure, the ring structure may contain a carbazole skeleton, a dibenzothiophene skeleton, or a dibenzofuran skeleton. fused rings having a skeleton (i.e., a carbazole skeleton, a dibenzothiophene skeleton, or a dibenzothiophene skeleton) This also includes fused rings in which a ring is further fused to the benzofuran skeleton.

[0088] Another embodiment of the present invention is an organic compound represented by General Formula (G0).

[0089] [ka]

[0090] In the general formula (G0), Q represents oxygen or sulfur, and Ar 1 is a substituted or unsubstituted condensed represents an aromatic ring, and R 1 and R 2 are each independently hydrogen or a group having a total of 1 to 100 carbon atoms. represents a group of R 1 and R 2 At least one of the groups has a fused ring.

[0091] Another embodiment of the present invention is an organic compound represented by General Formula (G0).

[0092] [ka]

[0093] In the general formula (G0), Q represents oxygen or sulfur, and Ar 1 is a substituted or unsubstituted naphthyl group. A phenanthrene ring, a substituted or unsubstituted phenanthrene ring, and a substituted or unsubstituted chrysene represents one of the rings, and R 1 and R2 are each independently hydrogen or a group having a total of 1 or more carbon atoms. represents a group of 100 or less, and R 1 and R 2 At least one of the groups has a fused ring.

[0094] R 1 and R 2 The fused rings possessed by at least one of the above are substituted or unsubstituted fused aromatic hydrocarbons. It is either a hydrogen ring or a substituted or unsubstituted π-excessive condensed heteroaromatic ring. It is preferable that:

[0095] The fused ring is a dibenzothiophene skeleton, a dibenzofuran skeleton, or a carbazole skeleton. It is preferably a substituted or unsubstituted fused heteroaromatic ring having any one of the above.

[0096] As mentioned above, in this specification and the like, the fused heteroaromatic ring includes a carbazole ring, a dibenzo Not only thiophene ring and dibenzofuran ring, but also carbazole skeleton and dibenzothiophene skeleton The term also includes fused rings in which a ring is further fused to the dibenzofuran skeleton.

[0097] The fused rings include a naphthalene skeleton, a fluorene skeleton, a triphenylene skeleton, and a phenanthrene skeleton. A substituted or unsubstituted fused aromatic hydrocarbon ring having one of the following skeletons: is preferred.

[0098] Another embodiment of the present invention is an organic compound represented by General Formula (G0).

[0099] [ka]

[0100] In the general formula (G0), Q represents oxygen or sulfur, and Ar 1is a substituted or unsubstituted condensed represents an aromatic ring, and R 1 and R 2 are each independently hydrogen or a group having a total of 1 to 100 carbon atoms. represents a group of R 1 and R 2 At least one of R has a hole transporting skeleton, 1 and R 2 At least one of the above represents a structure represented by general formula (u1). In general formula (u1), α represents represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, and n is 0 to 4 represents the integers, and A 1 represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and represents any one of substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms; , * represents a bond in general formula (G0).

[0101] Another embodiment of the present invention is an organic compound represented by General Formula (G0).

[0102] [ka]

[0103] In the general formula (G0), Q represents oxygen or sulfur, and Ar 1 is a substituted or unsubstituted naphthyl group. A phenanthrene ring, a substituted or unsubstituted phenanthrene ring, and a substituted or unsubstituted chrysene represents one of the rings, and R 1 and R 2 are each independently hydrogen or a group having a total of 1 or more carbon atoms. represents a group of 100 or less, and R 1 and R 2 at least one of the groups has a hole transporting skeleton, R 1 and R 2 At least one of the above represents a structure represented by general formula (u1). In the formula (I), α represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, and n represents represents an integer between 0 and 4, and A 1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms. represents one of the above, and * represents a bonding site in general formula (G0).

[0104] In general formula (u1), A 1 is represented by the general formula (A 1 -1) to general formula (A 1 -17) It is preferred that

[0105] [ka]

[0106] General formula (A 1 -1) to general formula (A 1 -17) Medium, R A1 ~R A11 are each independently , hydrogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted Cycloalkyl groups having 3 to 7 carbon atoms, and substituted or unsubstituted cycloalkyl groups having 6 to 30 carbon atoms. represents any one of the aryl groups below.

[0107] In the general formula (u1), the arylene group having 6 to 25 carbon atoms is a phenylene group. , naphthalenediyl group, biphenyldiyl group, anthracenediyl group, phenanthrene diyl group yl group, triphenylenediyl group, 9H-fluorenediyl group, 9,9-dimethylfluorenediyl group Examples include a diphenyl group and a 9,9'-spirobifluorenediyl group.

[0108] In the general formula (u1), α represents any one of the general formulae (Ar-1) to (Ar-14). It is preferable to represent

[0109] [ka]

[0110] In general formula (Ar-1) to general formula (Ar-14), R B1 ~R B14 are each independently , hydrogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted Cycloalkyl groups having 3 to 7 carbon atoms, and substituted or unsubstituted cycloalkyl groups having 6 to 30 carbon atoms. represents any one of the aryl groups below.

[0111] In each of the organic compounds according to one embodiment of the present invention, in general formula (G0), Ar 1 is one It is preferable that the compound represents any one of general formulas (t1) to (t3).

[0112] [ka]

[0113] In general formula (t1) to general formula (t3), R 3 ~R 24 are each independently hydrogen, substituted or or unsubstituted alkyl groups having 1 to 6 carbon atoms; The following cycloalkyl groups and substituted or unsubstituted aryl groups having 6 to 30 carbon atoms: and * represents a bonding site in general formula (G0).

[0114] Among the organic compounds represented by general formula (G0), the organic compounds represented by general formula (G1) are preferred. This is more preferable. The T1 level of the organic compound can be further lowered.

[0115] [ka]

[0116] In the general formula (G1), Q represents oxygen or sulfur, and Ar 1 is a substituted or unsubstituted condensed Aromatic ring (or substituted or unsubstituted naphthalene ring, substituted or unsubstituted phenanthrene ring) R represents a substituted or unsubstituted chrysene ring; 1 and R 2 each independently represents hydrogen or a group having a total of 1 to 100 carbon atoms; R 1 and R 2 of At least one of them has a hole-transporting skeleton or fused ring.

[0117] Among the organic compounds represented by the general formula (G0), the organic compounds represented by the general formulas (G1-1) to (G1-4) ) is particularly preferred.

[0118] [ka]

[0119] In the general formulae (G1-1) to (G1-4), Q represents oxygen or sulfur, and R 1 and R 2 each independently represents hydrogen or a group having a total of 1 to 100 carbon atoms; R 1 and R 2 At least one of R has a hole transporting skeleton or fused ring, 3 ~R 8 and R 17 ~ R 24are each independently hydrogen or a substituted or unsubstituted alkyl having 1 to 6 carbon atoms. groups, substituted or unsubstituted cycloalkyl groups having 3 to 7 carbon atoms, and substituted or unsubstituted It represents any one of substituted aryl groups having 6 to 30 carbon atoms.

[0120] In addition, the general formula (G0), the general formula (G1), and the general formulas (G1-1) to (G1-4) ) in R 1 and R 2 The group having a total of 1 to 100 carbon atoms in represents an unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted alkyl group having 3 to 7 carbon atoms. a cycloalkyl group represented by the formula (I), a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and Examples include substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms. and R 1 and R 2 At least one of the above has the above-mentioned hole transporting skeleton or fused ring. .

[0121] In addition, general formula (G0), general formula (G1), general formula (t1) to general formula (t3), general formula ( G1-1) to general formula (G1-4), general formula (u1), general formula (A 1 -1) to general formula ( A 1 -17), and the "substituted or unsubstituted" of general formulas (Ar-1) to (Ar-14). In the case of "substituted X" (X is a ring, skeleton, group, etc.), if X has a substituent, the substituent Examples of the group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and an isobutyl group. 1-carbon groups such as sec-butyl, tert-butyl, pentyl, and hexyl groups Alkyl groups with 7 or more and 7 or less, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cycloalkyl groups having 5 to 7 carbon atoms, such as 9,10-trinorbornanyl groups; and aryl groups having 6 to 12 carbon atoms, such as phenyl, naphthyl, and biphenyl groups. etc.

[0122] General formula (t1) to general formula (t3), general formula (G1-1) to general formula (G1-4), general Formula (A 1 -1) to general formula (A 1 -17), and general formula (Ar-1) to general formula (Ar In -14), examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propane group, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl ethyl group, pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, ne pentyl group, hexyl group, isohexyl group, 3-methylpentyl group, 2-methylpentyl group butyl group, 2-ethylbutyl group, 1,2-dimethylbutyl group, 2,3-dimethylbutyl group, n -heptyl group and the like.

[0123] General formula (t1) to general formula (t3), general formula (G1-1) to general formula (G1-4), general Formula (A 1 -1) to general formula (A 1 -17), and general formula (Ar-1) to general formula (Ar In -14), the cycloalkyl group having 3 to 7 carbon atoms is a cyclopropyl group. , cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-methylcyclohexyl group , 2,6-dimethylcyclohexyl group, cycloheptyl group, cyclooctyl group, etc. can be.

[0124] General formula (t1) to general formula (t3), general formula (G1-1) to general formula (G1-4), general Formula (u1), general formula (A1 -1) to general formula (A 1 -17), and general formula (Ar-1) In the general formula (Ar-14), the aryl group having 6 to 30 carbon atoms is phenyl. nyl group, o-tolyl group, m-tolyl group, p-tolyl group, mesityl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, 1-naphthyl group, 2-naphthyl group, fluorenyl group, 9,9-dimethylfluorenyl group, spirofluorenyl group, phenanthrenyl group, Examples thereof include anthracenyl group and fluoranthenyl group.

[0125] General formula (G0), general formula (G1), and general formulas (G1-1) to (G1-4) Hey, R 1 and R 2 In the group having a total carbon number of 1 to 100, the following alkyl groups, cycloalkyl groups having 3 to 7 carbon atoms, and alkyl groups having 6 to 30 carbon atoms: Specific examples of the aryl group include those described above. 00 or less, and a heteroaryl group having 3 to 30 carbon atoms in the general formula (u1). Examples of the alkyl group include a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an indolo group, and the like. Carbazolyl group, benzoindolocarbazolyl group, dibenzoindolocarbazolyl group, benzoindolobenzcarbazolyl group, dibenzothienyl group, benzonaphthothienyl group, dibenzothienyl group, Examples include monovalent groups such as a benzofuranyl group and a benzonaphthofuranyl group.

[0126] Specific examples of the organic compound according to one embodiment of the present invention include those represented by structural formulas (100) to (117). However, the present invention is not limited to these.

[0127] [ka]

[0128] [ka]

[0129] [Method for synthesizing an organic compound according to one embodiment of the present invention] Various reactions can be applied to synthesize the organic compound of one embodiment of the present invention. The synthesis method of the organic compound represented by the general formula (G0) is exemplified below. An example of a method for synthesizing an organic compound represented by the general formula (G0' The organic compound represented by the formula (1) is a furoquinoxaline derivative or a condensed aromatic compound having a condensed aromatic ring. An organic compound represented by the general formula (G0), which is a thienoquinoxaline derivative in which aromatic rings are condensed This is one aspect of the above.

[0130] [ka]

[0131] In the general formula (GO'), Q represents oxygen or sulfur, and Ar 1 is substituted or unsubstituted R represents a condensed aromatic ring 1 represents a group having 1 to 100 carbon atoms, and R 1 is a hole It has a transportable backbone or fused rings.

[0132] <Method for synthesizing organic compound represented by general formula (G0')> First, as shown in the synthetic scheme (A-1), The arylboronic acid (a1) and the quinoxaline derivative substituted with amino groups and halogens were After coupling with compound (a2) to obtain intermediate (a3), intermediate (a3) ​​and nitrous acid are reacted with By reacting with tert-butyl acetate and cyclizing, a fused aromatic ring is obtained. A thienoquinoxaline derivative (a4) having a condensed aromatic ring or a thienoquinoxaline derivative (a4) is obtained. In the synthesis scheme (A-1), Y 1 If is a halogen, aromatic compounds containing halogen Boronic acid (Y 3 -(α)nB 2 The intermediate (a5) obtained by coupling It can be used in the subsequent reaction in the same manner as the noxaline derivative (a4).

[0133] [ka]

[0134] In the synthetic scheme (A-1), Q represents oxygen or sulfur, and Ar 1 is a substitution or represents an unsubstituted fused aromatic ring, and Y 1 represents a halogen or an aromatic ring containing a halogen, and Y 1 teeth One or two, Y 2 represents a halogen, and Y 3 represents an aromatic ring containing a halogen, and Y 3 is one or two, and α is a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. represents an olefin group, n represents an integer of 0 or more and 4 or less, B 1 and B 2 are boronic acids, respectively. , boronic acid ester, or cyclic triol borate salt. As the borate salt, potassium salt and sodium salt may be used in addition to lithium salt.

[0135] In the synthesis scheme (A-1), organic compounds represented by general formula (a4) and general formula (a5) The compound is a raw material for an organic compound according to one embodiment of the present invention, as shown in Synthesis Scheme (A-2). .

[0136] Next, as shown in the synthesis scheme (A-2), the condensed amine obtained in the synthesis scheme (A-1) is reacted with the amine to form a condensed amine. Aromatic ring-fused furoquinoxaline derivatives or fused aromatic ring-fused thienoquinoxaline derivatives By coupling the boronic acid compound (b1) with the boronic acid derivative (a4), An organic compound represented by general formula (G0') can be obtained.

[0137] [ka]

[0138] In the synthetic scheme (A-2), Q represents oxygen or sulfur, and Ar 1 is a substitution or represents an unsubstituted fused aromatic ring, and R 1 represents a group having 1 to 10 carbon atoms, and R 1 teeth, It has a hole transporting skeleton, and Y 1 represents one or two halogens, B 3 is a boronic acid, It represents a boronic acid ester, a cyclic triol borate salt, or the like. As the phosphate salt, potassium salt and sodium salt may be used in addition to lithium salt.

[0139] The methyloxy group or methylthio group used in the synthesis schemes (A-1) and (A-2) Arylboronic acid (a1) substituted with a group, quinoxalic acid (a2) substituted with an amino group and a halogen Various types of boronic acid derivatives (a2) and boronic acid compounds (b1) are commercially available or can be purchased from other sources. Since it can be synthesized, the fused aromatic ring represented by the above general formula (G0') can be used as a fused aromatic ring. There are many thienoquinoxaline derivatives or thienoquinoxaline derivatives fused with condensed aromatic rings. Therefore, the organic compound according to one embodiment of the present invention can be synthesized in a variety of types. It is characterized by a wide range of options.

[0140] Although the synthesis method of an organic compound according to one embodiment of the present invention has been described above, the present invention is not limited thereto. It is not necessary to synthesize it by other synthesis methods.

[0141] As described above, the organic compound of one embodiment of the present invention has high heat resistance and emits red light to near-infrared light. The compound is suitable as a material for a light-emitting device (particularly as a host material or an electron transport material). By using the organic compound of one aspect of the present invention, light emission of a light-emitting device that emits red light to near-infrared light can be achieved. Furthermore, by using the organic compound of one embodiment of the present invention, it is possible to improve the efficiency of red light. The lifetime of a light-emitting device that emits infrared to near-infrared light can be extended. By using such organic compounds, we have been able to improve the heat resistance of light-emitting devices that emit red to near-infrared light. Furthermore, by using the organic compound of one embodiment of the present invention, red light to near-infrared light can be The reliability of the light-emitting device that emits external light can be improved.

[0142] This embodiment mode can be combined with other embodiment modes as appropriate. In the case where multiple configuration examples are shown in one embodiment, the configuration examples may be combined as appropriate. It is possible to do this.

[0143] (Embodiment 2) In this embodiment, a light-emitting device of one embodiment of the present invention will be described with reference to FIG. In the embodiment, a light emitting device having a function of emitting visible light or near infrared light will be described. do.

[0144] [Example of light-emitting device configuration] <Basic structure of light-emitting devices> 1A to 1D show an example of a light-emitting device having an EL layer between a pair of electrodes.

[0145] The light-emitting device shown in FIG. 1A includes an EL layer 10 between a first electrode 101 and a second electrode 102. The EL layer 103 has at least a light-emitting layer. do.

[0146] 1B shows an example of a stacked structure of the EL layer 103. In this embodiment, the first electrode 101 The case where the first electrode 101 functions as an anode and the second electrode 102 functions as a cathode will be described as an example. The EL layer 103 is formed by stacking a hole injection layer 111, a hole transport layer 112, and a light emitting layer 113 on the first electrode 101. The layer 113, the electron transport layer 114, and the electron injection layer 115 are stacked in this order. an electron injection layer 111, a hole transport layer 112, an emitting layer 113, an electron transport layer 114, and an electron injection layer 115; The first electrode 101 may have a single layer structure or a multilayer structure. If the first electrode 102 is the cathode and the second electrode 103 is the anode, the stacking order is reversed.

[0147] The light-emitting device may have multiple EL layers between a pair of electrodes. The substrate has n EL layers (n is an integer of 2 or more), and the (n-1)th EL layer and the nth EL layer It is preferable to have a charge generating layer 104 between the L layer and the charge generating layer 104 .

[0148] FIG. 1C shows a tandem type LED having two EL layers (EL layers 103a and 103b) between a pair of electrodes. FIG. 1D shows a light-emitting device having a three-layer EL layer (EL layers 103a, 103b, 103c, 103d, 103e, 103f, 103g, 103h, 103i, 103j ... 103b, 103c) and a light-emitting device having a tandem structure.

[0149] Each of the EL layers 103a, 103b, and 103c includes at least a light-emitting layer. Even in the case of a tandem structure having multiple EL layers as shown in FIG. 1D, each EL layer 1B. , 103b, and 103c are the hole injection layer 111, the hole transport layer 112, and the electron transport layer 113, respectively. The layer may have one or more of a layer 114 and an electron injection layer 115 .

[0150] The charge generating layer 104 shown in FIG. 1C is formed by applying a voltage between the first electrode 101 and the second electrode 102. When the electrons are injected into one of the EL layers 103a and 103b, holes are injected into the other. Therefore, in FIG. 1C, the first electrode 101 has a function of injecting electrons (holes). When a voltage is applied so that the potential becomes higher than that of the electrode 102, EL Electrons are injected into layer 103a and holes are injected into EL layer 103b.

[0151] From the viewpoint of light extraction efficiency, the charge generating layer 104 is preferably a layer that transmits visible light or near-infrared light. (Specifically, the transmittance of the charge generating layer 104 for visible light or near-infrared light is 40% or more.) In addition, the charge generation layer 104 is preferably formed on the first electrode 101 or the second electrode 102. It will function even at lower conductivities than

[0152] By providing the EL layers in contact with each other, the same structure as the charge generating layer 104 is formed between them. In this case, the EL layers can be provided in contact with each other without a charge generating layer therebetween. When a charge generating region is formed on one side of the EL layer, the EL layer is provided in contact with that surface. It is possible.

[0153] Tandem-structure light-emitting devices have higher current efficiency and The current required to emit light at a certain brightness is small. This results in a long life for the light-emitting device. The reliability of light-emitting devices and electronic devices can be improved.

[0154] The light-emitting layer 113 contains a light-emitting material or a combination of materials, and emits fluorescent light of a desired wavelength. The light-emitting layer 113 can have a structure that can emit light or phosphorescent light. In this case, the luminescent materials and the like used in each of the luminescent layers may be different. The other materials may be different materials. The layers 103a, 103b, and 103c may be configured to emit light of different wavelengths. In this case, the luminescent material and other materials used in each luminescent layer may be different. For example, in FIG. 1C, the EL layer 103a is configured to emit red and green light, and the EL layer 103 By configuring b to emit blue light, the light-emitting device as a whole emits white light. In addition, one light-emitting device can be made up of light-emitting layers or layers that exhibit the same color. For example, in FIG. 1D, the EL layer 103a is a first blue EL layer. The EL layer 103b emits yellow or yellow-green light and red light. The EL layer 103c is configured to emit the second blue light, thereby forming a light-emitting device. It is possible to obtain a light-emitting device that emits white light as a whole.

[0155] In the light-emitting device according to one embodiment of the present invention, light emitted from the EL layer is resonated between a pair of electrodes. For example, in FIG. 1B, The first electrode 101 is a reflective electrode, and the second electrode 102 is a semi-transparent and semi-reflective electrode. By forming a micro-optical resonator (microcavity) structure, the light emitted from the EL layer 103 can be This can intensify the emitted light.

[0156] By applying a microcavity structure to light-emitting devices, different EL layers can be obtained. Therefore, it is possible to obtain different emission colors by using a This eliminates the need to form different functional layers for each pixel (so-called separate coating). It is also possible to combine it with a colored layer (color filter). Furthermore, it is possible to increase the light emission intensity of a specific wavelength in the front direction, resulting in low power consumption. It is possible to electrify the system.

[0157] The first electrode 101 of the light-emitting device is reflective to visible light or near-infrared light. and a conductive film that transmits visible light or near-infrared light. In the case of a light-transmitting electrode, optical adjustment is performed by controlling the film thickness of the conductive film having light transmission properties. Specifically, the first voltage can be set to a value corresponding to the wavelength λ of the light obtained from the light emitting layer 113. The distance between the first electrode 101 and the second electrode 102 is approximately mλ / 2 (where m is a natural number). It is preferable to adjust it so that

[0158] In order to amplify the desired light (wavelength: λ) obtained from the light emitting layer 113, the first electrode the optical distance from 101 to the region (light-emitting region) of the light-emitting layer 113 where desired light is obtained, and the optical distance from the electrode 102 to the region (light-emitting region) of the light-emitting layer 113 where desired light is obtained, , and are adjusted to be close to (2m'+1)λ / 4 (where m' is a natural number). The light-emitting region here is preferably a region where holes and electrons are regenerated in the light-emitting layer 113. The binding regions are indicated.

[0159] By performing such optical adjustment, the spectrum of light obtained from the light emitting layer 113 can be narrowed. This allows light emission with good color purity to be obtained.

[0160] However, in the above case, strictly speaking, the optical distance between the first electrode 101 and the second electrode 102 is The total thickness from the reflective area of ​​the first electrode 101 to the reflective area of ​​the second electrode 102 is called However, it is difficult to precisely define the reflective areas of the first electrode 101 and the second electrode 102. Since it is difficult to determine the position of the first electrode 101 and the second electrode 102, The above effect can be obtained by assuming the first The optical distance between the electrode 101 and the light-emitting layer from which the desired light is obtained is, strictly speaking, 1 / 3 of the optical distance between the electrode 101 and the light-emitting layer from which the desired light is obtained. The optical distance is the distance between the reflection area in the light emitting layer and the light emitting area in the light emitting layer from which the desired light is obtained. However, it is possible to reduce the reflection area in the first electrode 101 and the emission area that can obtain the desired light. Since it is difficult to precisely determine the light-emitting region in the optical layer, the first electrode 101 may be arbitrarily selected. The position of the light emitting layer where the desired light is obtained is assumed to be the reflective region, and any position of the light emitting layer where the desired light is obtained is assumed to be the emitting region. It is assumed that the above-mentioned effects can be sufficiently obtained.

[0161] At least one of the first electrode 101 and the second electrode 102 is resistant to visible light or near-infrared light. The electrode is transparent to visible light or near-infrared light. The transmittance of external light must be 40% or more. In addition, the material must be transparent to visible light or near-infrared light. When the electrode is the semi-transmissive / semi-reflective electrode, the reflectance of the electrode for visible light or near-infrared light is , 20% or more and 80% or less, preferably 40% or more and 70% or less. The resistivity of is 1×10 -2 Ωcm or less is preferable.

[0162] The first electrode 101 or the second electrode 102 has reflectivity for visible light or near-infrared light. If the electrode is a reflective electrode, the reflectance of the reflective electrode for visible light or near-infrared light is 40%. The resistivity of the electrode is set to 70% or more and 100% or less, preferably 70% or more and 100% or less. is 1 x 10 -2 Ωcm or less is preferable.

[0163] <Specific structure of the light-emitting device> Next, a specific structure of the light-emitting device will be described. Here, the single-layer light-emitting device shown in FIG. The following description will be given using a light-emitting device having the structure.

[0164] <First electrode and second electrode> The materials for forming the first electrode 101 and the second electrode 102 are selected from those having the above-mentioned functions of both electrodes. If the above requirement is satisfied, the following materials can be used in appropriate combination. For example, , metals, alloys, electrically conductive compounds, and mixtures thereof can be used as appropriate. Specifically, In-Sn oxide (also called ITO), In-Si-Sn oxide (ITSO In-Zn oxide, In-W-Zn oxide, etc. Aluminum (Al), Titanium (Ti), Chromium (Cr), Manganese (Mn), Iron (Fe), Edge Copper (Co), Nickel (Ni), Copper (Cu), Gallium (Ga), Zinc (Zn), In Sium (In), Tin (Sn), Molybdenum (Mo), Tantalum (Ta), Tungsten (W), palladium (Pd), gold (Au), platinum (Pt), silver (Ag), yttrium ( Metals such as yttrium (Y), neodymium (Nd), and alloys containing these in appropriate combinations can be used. In addition, elements belonging to Group 1 or Group 2 of the periodic table that are not listed above (e.g. For example, lithium (Li), cesium (Cs), calcium (Ca), strontium (S r), europium (Eu), ytterbium (Yb), and other rare earth metals, An alloy containing an appropriate combination of these, graphene, etc. can be used.

[0165] When a light-emitting device having a microcavity structure is to be fabricated, the first electrode 10 The first electrode 101 is formed as a reflective electrode, and the second electrode 102 is formed as a semi-transmissive and semi-reflective electrode. Therefore, it is possible to form the conductive film by using one or more desired conductive materials in a single layer or in a laminated layer. The second electrode 102 can be formed by selecting a material in the same manner as above after forming the EL layer 103. These electrodes are formed by using sputtering or vacuum deposition. It is possible.

[0166] <Hole injection layer and hole transport layer> The hole injection layer 111 is a layer that injects holes from the first electrode 101, which is an anode, to the EL layer 103. and is a layer containing a material with high hole injection properties.

[0167] Materials with high hole injection properties include molybdenum oxide, vanadium oxide, and ruthenium oxide. transition metal oxides such as tungsten oxide and manganese oxide, phthalocyanine (abbreviation: Phthalocyanine compounds such as H2Pc and copper phthalocyanine (abbreviated as CuPc) are used. You can be there.

[0168] As a material with high hole injection properties, 4,4',4''-tris(N,N-diphenylamino) ) triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl) (N-phenylamino)triphenylamine (abbreviation: MTDATA), 4 ,4'-Bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl DPAB, 4,4'-bis(N-{4-[N'-(3-methylphenyl)- N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviated as DNTP D), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino] 3-[N-(9-phenylcarbazol-3-yl)benzene (abbreviation: DPA3B) )-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3, 6-Bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9- Phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-( 9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: P Aromatic amine compounds such as CzPCN1) can be used.

[0169] Materials with high hole injection properties include poly(N-vinylcarbazole) (abbreviated as PVK), poly(N-vinylcarbazole) and poly(vinylcarbazole). Poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'- [4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl ) methacrylamide] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl ether)] N,N'-bis(phenyl)benzidine (abbreviation: Poly-TPD) Alternatively, poly(3,4-ethylenedioxythiophene) / poly(styrene PEDOT / PSS), polyaniline / poly(styrene sulfonic acid) It is also possible to use a polymer compound to which an acid such as (PAni / PSS) has been added.

[0170] Materials with high hole injection properties include hole transport materials and acceptor materials (electron acceptor materials). In this case, a composite material containing an acceptor material can be used. Electrons are extracted from the conductive material, generating holes in the hole injection layer 111, which then pass through the hole transport layer 112. Holes are injected into the light-emitting layer 113 through the hole injection layer 111. The layer may be formed of a single layer of a composite material containing a hole transporting material and an acceptor material. The acceptor material may be laminated in separate layers.

[0171] The hole transport layer 112 transports holes injected from the first electrode 101 by the hole injection layer 111. The hole transport layer 112 is a layer that transports the electrons to the light emitting layer 113. The hole transport layer 112 is a layer that contains a hole transport material. The hole transporting material used for the hole transport layer 112 is particularly suitable for the highest occupied molecular orbital of the hole injection layer 111. It is preferable to use a compound having a HOMO level that is the same as or close to the HOMO level of the cation. It's nice.

[0172] Acceptor materials used in the hole injection layer 111 include those of Group 4 to 5 in the periodic table. Oxides of metals belonging to Group 8 can be used. Specifically, molybdenum oxide, Vanadium, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide Among them, molybdenum oxide is particularly stable in the atmosphere and is easily absorbed. It is preferred because it has low moisture resistance and is easy to handle. Other examples include quinodimethane derivatives and chloranil derivatives. Organic acceptors such as hexaazatriphenylene derivatives can be used. Compounds with withdrawing groups (halogen groups and cyano groups) include 7,7,8,8-tetracyano No-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ), chlorani 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexa- HAT-CN, 1,3,4,5,7,8-hexafluorotetrafluoroethylene Examples include thoracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ). In particular, electron-withdrawing groups are bonded to fused aromatic rings with multiple heteroatoms, such as HAT-CN. Compounds containing an electron-withdrawing group (especially a halogen group such as a fluoro group) are preferred because they are thermally stable. Radialene derivatives containing halogen or cyano groups have very high electron-accepting properties. Preferred is α,α',α''-1,2,3-cyclopropanetriylidenetri S[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α' ,α''-1,2,3-Cyclopropanetriylidenetris[2,6-dichloro-3,5 -difluoro-4-(trifluoromethyl)benzeneacetonitrile], α,α',α' '-1,2,3-Cyclopropanetriylidenetris[2,3,4,5,6-pentafluoro Orobenzeneacetonitrile] and the like.

[0173] The hole transporting material used in the hole injection layer 111 and the hole transport layer 112 is 10 -6 cm 2A material having a hole mobility of 1 / Vs or more is preferred. Any other suitable substance may be used.

[0174] As the hole transport material, π-electron-rich heteroaromatic compounds (e.g., carbazole derivatives, Thiophene derivatives, furan derivatives, etc.) and aromatic amines (compounds with an aromatic amine skeleton) Materials with high hole transport properties such as ZnO, ZnS, and ZnO are preferred.

[0175] Carbazole derivatives (compounds with a carbazole skeleton) include bicarbazole derivatives (e.g., 3,3'-bicarbazole derivatives), aromatic amines having a carbazolyl group etc.

[0176] Specific examples of bicarbazole derivatives (for example, 3,3'-bicarbazole derivatives) include: is 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 9,9 '-Bis(1,1'-biphenyl-4-yl)-3,3'-bi-9H-carbazole, 9 ,9'-Bis(1,1'-biphenyl-3-yl)-3,3'-bi-9H-carbazole , 9-(1,1'-biphenyl-3-yl)-9'-(1,1'-biphenyl-4-yl) )-9H,9'H-3,3'-bicarbazole (abbreviation: mBPCCBP), 9-(2-naphthalene butyl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: βNCC P) and others.

[0177] Specific examples of aromatic amines having a carbazolyl group include 4-phenyl-4'-(9 -phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1B P), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl )-9-phenyl-9H-carbazol-3-amine (abbreviation: PCBiF), N-(1, 1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3- [(phenyl)-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBB iF), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazole-3-yl) 1-naphthyl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-( 9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAN) B), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carbazole- 3-yl)triphenylamine (abbreviation: PCBNBB), 4-phenyldiphenyl-(9 -phenyl-9H-carbazol-3-yl)amine (abbreviation: PCA1BP), N,N' -bis(9-phenylcarbazol-3-yl)-N,N'-diphenylbenzene-1, 3-Diamine (abbreviation: PCA2B), N,N',N''-triphenyl-N,N',N' '-Tris(9-phenylcarbazol-3-yl)benzene-1,3,5-triamine (abbreviation: PCA3B), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl- 9H-carbazol-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF ), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl] [Il]spiro-9,9'-bifluoren-2-amine (abbreviation: PCBASF), PCzPC A1, PCzPCA2, PCzPCN1, 3-[N-(4-diphenylaminophenyl) -N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA1), 3,6 -Bis[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenyl Carbazole (abbreviation: PCzDPA2), 3,6-bis[N-(4-diphenylamino) [phenyl]-N-(1-naphthyl)amino]-9-phenylcarbazole (abbreviation: PCzT PN2), 2-[N-(9-phenylcarbazol-3-yl)-N-phenylamino] Spiro-9,9'-bifluorene (abbreviation: PCASF), N-[4-(9H-carbazol- [N-(4-phenyl)phenyl]-N-(4-phenyl)phenylaniline (abbreviation: YGA1B P), N,N'-bis[4-(carbazol-9-yl)phenyl]-N,N'-diphenyl Nyl-9,9-dimethylfluorene-2,7-diamine (abbreviation: YGA2F), 4,4' ,4''-tris(carbazol-9-yl)triphenylamine (abbreviation: TCTA) Examples include:

[0178] In addition to the above, the carbazole derivatives include 3-[4-(9-phenanthryl)-phenanthroline]- 3-[4-(1-naphthyl)]-9-phenyl-9H-carbazole (abbreviation: PCPPn), 1,3-Phenyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN) -bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl) Biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9- Phenylcarbazole (abbreviation: CzTP), 1,3,5-tris[4-(N-carbazolyl) 9-[4-(10-phenyl-9-anthracene]phenyl)benzene (abbreviation: TCPB), (racenyl)phenyl]-9H-carbazole (abbreviation: CzPA), and the like.

[0179] Thiophene derivatives (compounds with a thiophene skeleton) and furan derivatives (compounds with a furan skeleton) Specifically, the compound (which is a compound that yl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl- 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene DBTFLP-III, 4-[4-(9-phenyl-9H-fluorene-9 -yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV) Which compound has a thiophene skeleton, 4,4',4''-(benzene-1,3,5-trimethylsilyl) 4-[3-[3-(9-furanyl)tri(dibenzofuran)(abbreviation: DBF3P-II) (phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: m mDBFFLBi-II) and others.

[0180] Specific examples of aromatic amines include 4,4'-bis[N-(1-naphthyl)-N-phenyl]amine and 4,4'-bis[N-(1-naphthyl)-N-phenyl]amine. N,N'-bis(3-methylamino)biphenyl (abbreviation: NPB or α-NPD) (1,1'-biphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl )-N-phenylamino]biphenyl (abbreviation: BSPB), 4-phenyl-4'-(9- (phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl mBP AFLP), N-(9,9-dimethyl-9H-fluoren-2-yl)-N-{9,9- Dimethyl-2-[N'-phenyl-N'-(9,9-dimethyl-9H-fluorene-2- yl)amino]-9H-fluoren-7-yl}phenylamine (abbreviation: DFLADFL ), N-(9,9-dimethyl-2-diphenylamino-9H-fluoren-7-yl)di Phenylamine (abbreviation: DPNF), 2-[N-(4-diphenylaminophenyl)-N -phenylamino]spiro-9,9'-bifluorene (abbreviation: DPASF), 2,7-bi Spiro-9,9'-[N-(4-diphenylaminophenyl)-N-phenylamino] -bifluorene (abbreviation: DPA2SF), 4,4',4''-tris[N-(1-naphthyl) 1'-TNATA, TDAT A, m-MTDATA, N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenyl Examples include phenylenediamine (abbreviation: DTDPPA), DPAB, DNTPD, and DPA3B. can be.

[0181] Hole transport materials include PVK, PVTPA, PTPDMA, and Poly-TPD. Polymer compounds can also be used.

[0182] The hole transport material is not limited to the above, and may be one or a combination of various known materials. The hole injection layer 111 and the hole transport layer 112 can be formed in combination.

[0183] <Light-emitting layer> The light-emitting layer 113 is a layer containing a light-emitting material. The luminescent materials include blue, purple, blue-purple, green, yellow-green, yellow A material that emits light of a color such as red, orange, or near-infrared light is used as the light-emitting material. It is also possible to use different light-emitting materials for the multiple light-emitting layers. This allows for a configuration that exhibits different luminous colors (for example, a configuration that combines luminous colors that are complementary to each other). Furthermore, one emitting layer may have different luminescent materials. It may also have a laminated structure.

[0184] The light-emitting layer 113 contains one or more organic compounds (phosphatides) in addition to a light-emitting substance (guest material). The light-emitting device according to one embodiment of the present invention preferably includes a conductive material, a conductive layer ... The organic compound of one embodiment of the present invention described in Embodiment 1 may be used as one or more organic compounds. It is preferable that the compound is one or more organic compounds. One or both of the hole transporting material and the electron transporting material described in the embodiment can be used. Furthermore, a bipolar material may be used as one or more organic compounds.

[0185] The light-emitting material that can be used in the light-emitting layer 113 is not particularly limited, and may be any material having a high singlet excitation energy. luminescent material that converts energy into light in the visible or near-infrared region, or triplet excited energy A luminescent material can be used that converts the ghee into luminescence in the visible or near infrared range.

[0186] Luminescent materials that convert singlet excitation energy into light include fluorescent materials. Examples thereof include pyrene derivatives, anthracene derivatives, triphenylene derivatives, fluorene derivatives, and the like. Olene derivatives, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives , dibenzoquinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives Pyrene derivatives are particularly well known for their The photon yield is high, which is preferable. 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'-biphenyl N,N'-diphenylpyrene-1,6-diamine (abbreviation) Name: 1,6FrAPrn), N,N'-bis(dibenzothiophen-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]fura N,N'-(pyrene-1,6-diamine) (abbreviation: 1,6BnfAPrn), yl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-02), N,N'-(pyren-1,6-diyl)bis[ (6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation :1,6BnfAPrn-03).

[0187] In addition, 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2, 2'-Bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl- 9-anthryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2B Py), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N' -Diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-calcium (bazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (Abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-di N,9-diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA) Phenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazo PCAPA, 4-(10-phenyl-9-anthryl)-4 '-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PC BAPA), 4-[4-(10-phenyl-9-anthryl)phenyl]-4'-(9- Phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPBA ), perylene, 2,5,8,11-tetra(tert-butyl)perylene (abbreviation: TBP ), N,N''-(2-tert-butylanthracene-9,10-diyldi-4,1- phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine](abbreviation Name: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-a N-(2-phenyl-9H-carbazol-3-amine (abbreviation: 2PCAPPA), -[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-tri Phenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA) and the like can be used. do.

[0188] Furthermore, examples of luminescent materials that convert triplet excitation energy into luminescence include phosphorescent materials. and thermally activated delayed fluorescence (TDF) TADF (Tivated Delayed Fluorescence) materials are can be.

[0189] Phosphorescent materials include organometallic complexes, metal complexes (platinum complexes), and rare earth metal complexes. These emit different colors (emission peaks) depending on the substance, so they should be selected appropriately as needed. Select and use.

[0190] It has a blue or green color and the peak wavelength of the emission spectrum is between 450 nm and 570 nm. Some phosphorescent materials include the following:

[0191] For example, tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl )-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium (III) (abbreviation: [Ir(mpptz-dmp)3]), tris(5-methyl-3,4 -diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir (Mptz)3]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl [Ir(iPrp)] tz-3b)3]), tris[3-(5-biphenyl)-5-isopropyl-4-phenyl Ir(iPr) tz)3]), organometallic complexes with a 4H-triazole skeleton, such as tris[3-methyl ethyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato] Iridium(III) (abbreviation: [Ir(Mptz1-mp)3]), tris(1-methyl -5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) ) (abbreviation: [Ir(PrptZ1-Me)3]) The organometallic complex fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl] [Ir(iPrpmi)3] ), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]furan [Phenanthridineto]iridium(III) (abbreviation: [Ir(dmpimpt-Me)3] Organometallic complexes with imidazole skeletons such as bis[2-(4',6'-difluoromethyl) (triphenyl)pyridinato-N,C 2’ ]iridium(III) tetrakis(1-pyrazolyl) bis[2-(4',6'-difluorophenyl)pyridine]borate (abbreviation: FIr6) Ginat-N,C 2’ ]Iridium(III) picolinate (abbreviation: FIrpic), bis {2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N,C 2’} Iridium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]), Bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium( III) Acetylacetonate (abbreviation: FIr(acac)) and other compounds with electron-withdrawing groups Examples of suitable organometallic complexes include those having phenylpyridine derivatives as ligands.

[0192] It is green or yellow and the peak wavelength of the emission spectrum is between 495 nm and 590 nm. Some phosphorescent materials include the following:

[0193] For example, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation :[Ir(mppm)3]), tris(4-t-butyl-6-phenylpyrimidinato)i Lithium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonato)bis(trimethylsilyl) Bis(6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(m ppm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4 -phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2(a cac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenyl [Pyrimidinato]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]) , (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenyl [Ir(mpmppm)2(acac) ]), (acetylacetonato)bis{4,6-dimethyl-2-[6-(2,6-dimethyl phenyl)-4-pyrimidinyl-κN3]phenyl-κC}iridium(III) (abbreviation :[Ir(dmppm-dmp)2(acac)]), (acetylacetonato)bis(4 ,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)2( organometallic iridium complexes with pyrimidine skeletons, such as (acetyl acac)] cetonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III)( Abbreviation: [Ir(mppr-Me)2(acac)]), (acetylacetonato)bis(5 -isopropyl-3-methyl-2-phenylpyrazinato)iridium(III) (abbreviation: Organometallic pyrazine skeletons such as [Ir(mppr-iPr)2(acac)] Iridium complex, tris(2-phenylpyridinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(ppy)3]), bis(2-phenylpyridinato-N,C2’ ) Iriji Ir(III) acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), (benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: [I r(bzq)2(acac)]), tris(benzo[h]quinolinato)iridium(II I) (abbreviation: [Ir(bzq)3]), tris(2-phenylquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(pq)3]), bis(2-phenylquinolinato- N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(pq)2(a cac)]), [2-(4-phenyl-2-pyridinyl-κN)phenyl-κC]bis[ 2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir( ppy)2(4dppy)]), bis[2-(2-pyridinyl-κN)phenyl-κC] [2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC] Organometallic iridium complexes with pyridine skeletons, bis(2,4-diphenyl-1,3-o Xazolato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir( dpo)2(acac)]), bis{2-[4'-(perfluorophenyl)phenyl] Pyridinato-N,C 2’}Iridium(III) acetylacetonate (abbreviation: [Ir( p-PF-ph)2(acac)]), bis(2-phenylbenzothiazolato-N,C 2 ’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(bt)2(acac) ]), as well as organometallic complexes such as tris(acetylacetonato)(monophenanthroline) Rare earth metals such as terbium(III) (abbreviated as [Tb(acac)3(Phen)]) Examples include complexes of the aryl group.

[0194] Yellow or red, with a peak wavelength of 570 nm or more and 750 nm or less in the emission spectrum. Some phosphorescent materials include the following:

[0195] For example, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinyl] dinato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)yl Ir(5mdppm)2(dpm)], bis[4,6-di (Naphthalen-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) ) (abbreviation: [Ir(d1npm)2(dpm)]), tris(4-t-butyl-6-phenyl) Nylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)3]) A novel organometallic complex with a pyrimidine skeleton, (acetylacetonato)bis(2,3,5-trimethylsilyl) Triphenylpyrazinate)iridium(III) (abbreviation: [Ir(tppr)2(acac )]), bis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridine Ir(tppr)2(dpm) -2-[3-(3,5-dimethylphenyl)-5-phenyl-2-pyrazinyl-κN]fu phenyl-κC}(2,6-dimethyl-3,5-heptanedionato-κ 2 O,O') Iriji Ir(III) (abbreviation: [Ir(dmdppr-P)2(dibm)]), bis{4,6 -dimethyl-2-[5-(4-cyano-2,6-dimethylphenyl)-3-(3,5-di methylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,2,6,6-tetra ... Methyl-3,5-heptanedionate-κ 2 O,O')iridium(III) (abbreviation: [I r(dmdppr-dmCP)2(dpm)]), (acetylacetonato)bis[2-methyl Thiyl-3-phenylquinoxalinato-N,C 2’ ]Iridium(III) (abbreviation: [Ir (mpq)2(acac)]), (acetylacetonato)bis(2,3-diphenylquinoline Xalinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(dpq)2(acac )]), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxa [Ir(Fdpq)2(acac)]), bis{ 4,6-dimethyl-2-[5-(5-cyano-2-methylphenyl)-3-(3,5-di methylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,2,6,6-tetra ... Methyl-3,5-heptanedionato-κ2O,O')iridium(III) (abbreviation: [I Organometallic compounds with pyrazine skeletons such as r(dmdppr-m5CP)2(dpm)] complexes and tris(1-phenylisoquinolinato-N,C 2’ ) Iridium (III) (abbreviation Name: [Ir(piq)3]), bis(1-phenylisoquinolinato-N,C 2’ ) Iriji Ir(III) acetylacetonate (abbreviation: [Ir(piq)2(acac)]), bis[4,6-dimethyl-2-(2-quinolinyl-κN)phenyl-κC](2,4-pentaerythroyl) Tandione-κ 2O,O') Iridium(III) and other organic compounds with a pyridine skeleton Metal complex, 2,3,7,8,12,13,17,18-octaethyl-21H,23H- Platinum complexes such as porphyrin platinum(II) (abbreviation: [PtOEP]), tris(1,3 -diphenyl-1,3-propanedionato)(monophenanthroline)europium(I II) (abbreviation: [Eu(DBM)3(Phen)]), tris[1-(2-thenoyl)- 3,3,3-Trifluoroacetonato](monophenanthroline)europium(III) ) (abbreviation: [Eu(TTA)3(Phen)])

[0196] The organic compounds (host material, assist material, etc.) used in the light-emitting layer 113 include light-emitting materials such as One or more substances with an energy gap larger than the energy gap It can be selected and used.

[0197] When the luminescent material used in the luminescent layer 113 is a fluorescent material, the active material used in combination with the luminescent material As an organic compound, the energy level of the singlet excited state is high, and the energy level of the triplet excited state is low. It is preferable to use an organic compound with a low energy level.

[0198] Although some of the above examples overlap, preferred combinations with luminescent materials (fluorescent materials, phosphorescent materials) From this viewpoint, specific examples of organic compounds are shown below.

[0199] When the luminescent material is a fluorescent material, an organic compound that can be used in combination with the luminescent material Examples include anthracene derivatives, tetracene derivatives, phenanthrene derivatives, and pyrene derivatives. condensed polycyclic aromatic compounds such as chrysene derivatives, dibenzo[g,p]chrysene derivatives, etc. It can be obtained.

[0200] Specific examples of organic compounds (host materials) used in combination with fluorescent materials include 9-phenyl 3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole ( Abbreviation: PCzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthracene Diphenyl)phenyl]-9H-carbazole (abbreviation: DPCzPA), PCPN, 9,10-diphenyl Phenylanthracene (abbreviation: DPAnth), N,N-diphenyl-9-[4-(10 -phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: C zA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: D PhPA), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-a N,9-diphenyl-N-[4- (10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation Name: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-an tolyl)phenyl]phenyl}-9H-carbazol-3-amine (abbreviation: PCAPBA ), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-chlor 2PCAPA, 6,12-dimethoxy-5,11-diphenyl- Phenilchrysen, N,N,N',N',N'',N'',N''',N'''-Octav Phenyldibenzo[g,p]chrysene-2,7,10,15-tetraamine (abbreviation: DBC 1), CzPA, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-di Benzo[c,g]carbazole (abbreviation: cgDBCzPA), 6-[3-(9,10-di (phenyl-2-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviation Name: 2mBnfPPA), 9-phenyl-10-{4-(9-phenyl-9H-fluorene 9,phenyl-9-yl)-biphenyl-4'-yl}-anthracene (abbreviation: FLPPA), 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 (t-BuDNA), 9,9'-bianthryl (abbreviation: BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene ( abbreviation: DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviation DPNS2), 1,3,5-tri(1-pyrenyl)benzene (TPB3), 5 ,12-diphenyltetracene, 5,12-bis(biphenyl-2-yl)tetracene, etc. Examples include:

[0201] When the luminescent substance is a phosphorescent material, the organic compound used in combination with the luminescent substance is The triplet excitation energy (energy difference between the ground state and the triplet excited state) of the optical substance is three times higher than the An organic compound with a large doublet excitation energy may be selected.

[0202] A plurality of organic compounds (e.g., a first host material and a second host material) are mixed together to form an exciplex. When using a resist material (or assist material, etc.) in combination with a light-emitting substance, It is preferable to use a mixture of a plurality of organic compounds with a phosphorescent material (particularly an organometallic complex).

[0203] By using this structure, the energy transfer from the exciplex to the luminescent material, Ex Using TET (Exciplex-Triplet Energy Transfer) It is possible to efficiently obtain light emission with high excitation power. It is preferable to use a compound that easily forms an electron-transporting complex, and a compound that easily accepts holes (hole transport material). It is particularly preferable to combine the compound with a compound that readily accepts electrons (electron transporting material). Note that the organic compound of one embodiment of the present invention described in Embodiment 1 has a low LUMO level and The hole transport material and the electron transport material are suitable as compounds that easily accept electrons. As a specific example of the above, the materials described in this embodiment can be used. This makes it possible to simultaneously achieve high efficiency, low voltage operation, and long life for light-emitting devices.

[0204] Organic compounds that can be used in combination with a light-emitting substance when the light-emitting substance is a phosphorescent material Examples of the compounds include aromatic amines, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, and the like. Orchid derivatives, zinc and aluminum metal complexes, oxadiazole derivatives, triazoles Derivatives, benzimidazole derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives , pyrimidine derivatives, triazine derivatives, pyridine derivatives, bipyridine derivatives, phenane Examples include thoroline derivatives.

[0205] Among the above, aromatic amines (aromatic amine skeletons) which are organic compounds with high hole transport properties are compounds having the formula (III), carbazole derivatives, dibenzothiophene derivatives (thiophene derivatives) ), and specific examples of dibenzofuran derivatives (furan derivatives) include the above-mentioned hole transporting Specific examples of materials include the same as those mentioned above.

[0206] Specific examples of zinc and aluminum metal complexes, which are organic compounds with high electron transport properties, include: , tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4- Methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq3), bis(10 -hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis (2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), etc. Examples of the metal complex include a metal complex having a quinoline skeleton or a benzoquinoline skeleton.

[0207] In addition, bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: Zn PBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: Zn Metal complexes with oxazole or thiazole ligands such as BTZ can also be used. can be done.

[0208] Oxadiazole derivatives, triazole derivatives, and benzyl alcohols, which are organic compounds with high electron transport properties, Benzoimidazole derivatives, benzimidazole derivatives, quinoxaline derivatives, dibenzoxazole Specific examples of the phenanthroline derivatives include 2-(4-biphenylyl) )-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: P BD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxazolidinyl] Azol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1, 3,4-Oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviation: CO1 1), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl) )-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl )-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazo p-EtTAZ, 2,2',2''-(1,3,5-benzenetriyl) Tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(di benzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole ( Abbreviation: mDBTBIm-II), 4,4'-bis(5-methylbenzoxazole-2- yl)stilbene (abbreviation: BzOs), bathophenanthroline (abbreviation: Bphen), batho Cuproine (abbreviation: BCP), 2,9-bis(naphthalen-2-yl)-4,7-difluoro Phenyl-1,10-phenanthroline (abbreviation: NBphen), 2-[3-(dibenzothiazolinone) [4-(4-(4-phenyl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTP DBq-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl ]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3' -(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxazone Sarin (abbreviation: 2mCzBPDBq), 2-[4-(3,6-diphenyl-9H-carba [f,h]quinoxaline (abbreviation: 2CzPDBq -III), 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h ]quinoxaline (abbreviation: 7mDBTPDBq-II), and 6-[3-(dibenzothiophene (4-phenyl)dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDB q-II) and others.

[0209] Heterocyclic compounds with diazine skeletons and triazine skeletons, which are organic compounds with high electron transport properties, Specific examples of heterocyclic compounds having a pyridine skeleton include 4,6 -Bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPn P2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation :4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazole-9-yl)] 2-[4-[3-(N-phenyl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), (phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl} -4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 9-[3 -(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl mPCCzPTzn-02, 3,5-trimethyl-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn-02), -Bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCz PPy), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmP yPB) and others.

[0210] An organic compound with high electron transport properties is poly(2,5-pyridinediyl) (abbreviated as PPy ), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3 ,5-diyl)] (abbreviation: PF-Py), poly[(9,9-dioctylfluorene-2, 7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-B Polymer compounds such as Py can also be used.

[0211] TADF materials are materials that convert triplet excited states into singlet excited states using a small amount of thermal energy. It is possible to convert the electrons into electrons (reverse intersystem crossing) and efficiently emit light (fluorescence) from the singlet excited state. In addition, the conditions for efficiently obtaining thermally activated delayed fluorescence are three The energy difference between the doublet excitation level and the singlet excitation level is 0 eV or more and 0.2 eV or less, preferably The delayed fluorescence in TADF materials is between 0 eV and 0.1 eV. The light is an emission that has a spectrum similar to that of normal fluorescence, but has a significantly longer lifespan. The lifespan of -6 seconds or more, preferably 10 -3 More than a second.

[0212] TADF materials include, for example, fullerenes and their derivatives, and acridines such as proflavine. Derivatives, eosin, etc. Also, magnesium (Mg), zinc (Zn), cadmium Cd, Sn, Pt, In, or Palladium Examples of metal-containing porphyrins include metal-containing porphyrins containing Pd, etc. For example, protoporphyrin-tin fluoride complex (abbreviation: SnF2(Proto IX)) , mesoporphyrin-tin fluoride complex (abbreviated as SnF2(Meso IX)), hematopoietin Hematoxyl tin fluoride complex (abbreviated as SnF2 (Hemato IX)), coproporf Fluorine tetramethyl ester-tin fluoride complex (abbreviation: SnF2(Copro III- 4Me), octaethylporphyrin-tin fluoride complex (abbreviation: SnF2(OEP)) , etioporphyrin-tin fluoride complex (abbreviation: SnF2(Etio I)), octaethene Examples include thylporphyrin-platinum chloride complex (abbreviation: PtCl2OEP).

[0213] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[ 2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-T RZ), PCCzPTzn, 2-[4-(10H-phenoxazin-10-yl)phenyl yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[ 4-(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5 -diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9- Dimethyl-9H-acridin-10-yl)-9H-xanthen-9-one (abbreviation: AC RXTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl ] sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10'H-spiro[ Acridine-9,9'-anthracene]-10'-one (abbreviation: ACRSA), etc. Heterocyclic compounds having a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring can be used. In addition, substances in which a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring are directly bonded are , the donor property of the π-electron rich heteroaromatic ring and the acceptor property of the π-electron deficient heteroaromatic ring are both This is particularly preferred because it increases the intensity of the excitation light and reduces the energy difference between the singlet and triplet excited states. It's nice.

[0214] When using a TADF material, it can also be used in combination with other organic compounds. In particular, it can be combined with the above-mentioned host material, hole transport material, and electron transport material.

[0215] Furthermore, the above materials can be used in combination with low molecular weight materials or high molecular weight materials to form the light emitting layer 113. The film can be formed by a known method (such as vapor deposition, coating, or printing). ) can be used as appropriate.

[0216] <Electron transport layer> The electron transport layer 114 transports electrons injected from the second electrode 102 by the electron injection layer 115. The electron transport layer 114 is a layer that transports electrons to the light-emitting layer 113. The electron transport material used in the electron transport layer 114 is 1×10 -6 cm 2 / Vs or more It is preferable that the material has an electron mobility higher than that of the hole transporting material. The light-emitting device according to one embodiment of the present invention can be used in an electronic transport device. The electron-transporting material used in the transport layer 114 may contain the organic compound of one embodiment of the present invention. preferable.

[0217] As the electron transporting material, metal complexes having a quinoline skeleton, Metal complexes, metal complexes having an oxazole skeleton, metal complexes having a thiazole skeleton, etc. , oxadiazole derivatives, triazole derivatives, imidazole derivatives, oxazole derivatives conductors, thiazole derivatives, phenanthroline derivatives, quinoline derivatives with quinoline ligands Conductors, benzoquinoline derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, pyridine derivatives derivatives, bipyridine derivatives, pyrimidine derivatives, and other nitrogen-containing heteroaromatic compounds. A material having high electron transporting properties, such as a π-electron deficient heteroaromatic compound, can be used.

[0218] As specific examples of the electron transporting material, the materials shown above can be used.

[0219] <Electron injection layer> The electron injection layer 115 is a layer containing a material with high electron injection properties. Lithium fluoride (LiF), Cesium fluoride (CsF), Calcium fluoride (CaF2), Lithium oxide (LiO x ) and the like, alkali metals, alkaline earth metals, or Compounds such as erbium fluoride (ErF3) can also be used. Alternatively, an electride may be used for the electron injection layer 115. For example, an electride is a mixed oxide of calcium and aluminum with electrons added. The above-mentioned material constituting the electron transport layer 114 may be a material containing a high concentration of dopant. It can also be used.

[0220] The electron injection layer 115 contains an electron transport material and a donor material (electron donor material). Composite materials may also be used. Such composite materials are made by adding electrons to organic compounds via electron donors. In this case, the organic compound is It is preferable that the material is excellent in transporting the generated electrons. Specifically, for example, The electron transporting material (metal complex, heteroaromatic compound, etc.) used for the electron transporting layer 114 is The electron donor can be any substance that exhibits electron donating properties to organic compounds. Specifically, alkali metals, alkaline earth metals and rare earth metals are preferred, and lithium, Examples include cesium, magnesium, calcium, erbium, and ytterbium. In addition, alkali metal oxides and alkaline earth metal oxides are preferred, and lithium oxide, calcium oxide, Examples of suitable oxides include ammonium oxide, barium oxide, etc. Also, Lewis salts such as magnesium oxide In addition, organic compounds such as tetrathiafulvalene (TTF) can also be used. can also be used.

[0221] <Charge generation layer> In the light-emitting device shown in FIG. 1C, the charge generating layer 104 is connected to the first electrode 101 (anode). When a voltage is applied between the second electrode 102 (cathode) and the EL layer 103a, electrons are injected into the EL layer 103a. It also has the function of injecting holes into the EL layer 103b.

[0222] The charge generation layer 104 contains a hole transport material and an acceptor material (electron acceptor material). The layer may have a structure containing an electron transport material and a donor material. By forming the charge generating layer 104 having such a configuration, it is possible to improve the driving efficiency when an EL layer is laminated. The voltage rise can be suppressed.

[0223] The hole transporting material, the acceptor material, the electron transporting material, and the donor material are The materials mentioned above can be used.

[0224] Note that the light-emitting device shown in this embodiment mode can be manufactured by a vacuum process such as evaporation or a spin process. Solution processes such as the ink-jet method and the vapor deposition method can be used. In this case, sputtering, ion plating, ion beam deposition, and molecular beam deposition are used. , physical vapor deposition (PVD) methods such as vacuum deposition, chemical vapor deposition (CVD) methods, etc. In particular, the functional layers included in the EL layer (hole injection layer, hole transport layer, light-emitting layer, electron transport layer , electron injection layer) and charge generation layer, deposition method (vacuum deposition method, etc.), coating method (dip coating method, die coating method, bar coating method, spin coating method, spray coating method, etc.), printing Methods (inkjet method, screen (stencil printing) method, offset (lithographic printing) method, flexible It can be formed by methods such as letterpress printing, gravure printing, microcontact printing, etc. This can be done.

[0225] The materials of the functional layer and the charge generating layer constituting the EL layer 103 are not limited to the above-mentioned materials. For example, polymer compounds (oligomers, dendrimers, polymers) can be used as materials for the functional layer. mers, etc.), medium molecular weight compounds (compounds in the intermediate range between low molecular weight and high molecular weight: molecular weight 400 to 400 0), inorganic compounds (quantum dot materials, etc.), etc. may also be used. colloidal quantum dot materials, alloy quantum dot materials, core-shell quantum dot materials , core-type quantum dot materials, etc. can be used.

[0226] This embodiment mode can be combined with other embodiment modes as appropriate.

[0227] (Embodiment 3) In this embodiment, a light-emitting device according to one embodiment of the present invention will be described with reference to FIGS.

[0228] [Configuration example 1 of light-emitting device] 2A shows a top view of the light emitting device, and FIGS. 2B and 2C show the structure between the dashed dotted line X1-Y1 in FIG. 2A. 2A to 2C are cross-sectional views taken along the line X2-Y2. The light-emitting device shown in FIGS. 2A to 2C may be, for example, a lighting device. The light emitting device can be used in bottom emission, top emission, dual emission, It may be either a light emission or a light emission.

[0229] The light emitting device shown in FIG. 2B includes a substrate 490a, a substrate 490b, a conductive layer 406, a conductive layer 416, The insulating layer 405, the organic EL device 450 (first electrode 401, EL layer 402, and second electrode 403) The organic EL device 450 includes a light-emitting element, an organic The EL layer 402 may be called an EL element, a light-emitting device, or the like. For example, the light-emitting layer may contain the organic compound of one embodiment of the present invention. It is preferable that the organic compound is contained as one or both of the materials of the electron transport layer and the electron-transport layer.

[0230] The organic EL device 450 includes a first electrode 401 on a substrate 490a and a The EL layer 402 and the second electrode 403 on the EL layer 402. Layer 407 and substrate 490b encapsulate organic EL device 450.

[0231] The ends of the first electrode 401 , the conductive layer 406 , and the conductive layer 416 are covered with an insulating layer 405 . The conductive layer 406 is electrically connected to the first electrode 401, and the conductive layer 416 is electrically connected to the second electrode 403. The conductive layer 406 covered with the insulating layer 405 via the first electrode 401 is It functions as an auxiliary wiring and is electrically connected to the first electrode 401. Organic EL device 450 By providing auxiliary wiring electrically connecting to the electrode, it is possible to suppress the voltage drop caused by the resistance of the electrode. The conductive layer 406 may be provided on the first electrode 401. In addition, auxiliary wiring electrically connected to the second electrode 403 may be provided on the insulating layer 405 or the like. good.

[0232] The substrate 490a and the substrate 490b are made of glass, quartz, ceramic, or sapphire, respectively. The substrate 490a and the substrate 490b may be flexible. The material allows the display device to be more flexible.

[0233] The light-emitting surface of the light-emitting device is equipped with a light extraction structure to increase light extraction efficiency and a structure to prevent dust from adhering. anti-static film that prevents adhesion of dirt, water-repellent film that prevents scratches caused by use A hard coat film, an impact absorbing layer, etc. may be disposed.

[0234] Examples of insulating materials that can be used for the insulating layer 405 include acrylic resin and epoxy. Resins such as resins, silicon oxide, silicon oxynitride, silicon nitride oxide, silicon nitride, Examples of the insulating material include inorganic insulating materials such as aluminum oxide.

[0235] The adhesive layer 407 may be a photo-curable adhesive such as an ultraviolet curable adhesive, a reaction-curable adhesive, or a thermosetting adhesive. Various curing adhesives such as adhesives and anaerobic adhesives can be used. Epoxy resin, acrylic resin, silicone resin, phenolic resin, polyimide resin, Imide resin, PVC (polyvinyl chloride) resin, PVB (polyvinyl butyral) resin Examples of the resin include EVA (ethylene vinyl acetate) resin. A material with low wettability is preferred. A two-component resin may also be used. etc. may also be used.

[0236] The light emitting device shown in FIG. 2C includes a barrier layer 490c, a conductive layer 406, a conductive layer 416, and an insulating layer 40 5, an organic EL device 450, an adhesive layer 407, a barrier layer 423, and a substrate 490b. do.

[0237] Barrier layer 490c shown in FIG. 2C is formed by interposing substrate 420, adhesive layer 422, and high-barrier insulating layer 490c. It has a layer 424.

[0238] In the light-emitting device shown in FIG. 2C, an insulating layer 424 having high barrier properties and a barrier layer 423 are provided between the insulating layer 424 and the barrier layer 423. The organic EL device 450 is disposed on the substrate 420. Therefore, compared to the substrate 420 and the substrate 490b, Even if a resin film with relatively low waterproofing is used, impurities such as water can get into the OLED device. This can prevent the shortening of the life span due to the incorporation of the solder.

[0239] The substrate 420 and the substrate 490b are each made of, for example, polyethylene terephthalate (P Polyester resins such as polyethylene naphthalate (ET), polyethylene naphthalate (PEN), polyacrylonite Acrylic resin, polyimide resin, polymethyl methacrylate resin, polycarbonate Polycarbonate (PC) resin, Polyethersulfone (PES) resin, Polyamide resin (Nylon , aramid, etc.), polysiloxane resin, cycloolefin resin, polystyrene resin, poly Amide-imide resin, polyurethane resin, polyvinyl chloride resin, polyvinylidene chloride resin, Polypropylene resin, polytetrafluoroethylene (PTFE) resin, ABS resin, cell The substrate 420 and the substrate 490b may be made of a flexible material. Glass having a thickness sufficient to provide the desired properties may also be used.

[0240] The insulating layer 424 having high barrier properties is preferably an inorganic insulating film. Examples of the film include a silicon nitride film, a silicon oxynitride film, a silicon oxide film, and a silicon nitride oxide film. Silicon film, aluminum oxide film, aluminum nitride film, etc. can be used. Hafnium oxide film, yttrium oxide film, zirconium oxide film, gallium oxide film, titanium oxide film tantalum film, magnesium oxide film, lanthanum oxide film, cerium oxide film, and neodymium oxide film Also, two or more of the above insulating films may be stacked.

[0241] The barrier layer 423 preferably has at least one inorganic film. The layer 423 may have a single layer structure of an inorganic film or a laminated structure of an inorganic film and an organic film. The inorganic film is preferably the inorganic insulating film described above. a silicon nitride film, a silicon oxide film, an organic film, a silicon oxide film, and a silicon nitride film; The protective layer may have a laminated structure of an inorganic film and an organic film. This prevents impurities (typically hydrogen, water, etc.) from entering the organic EL device 450. It can be suitably suppressed.

[0242] The insulating layer 424 with high barrier properties and the organic EL device 450 are mounted on a flexible substrate 420. In this case, the adhesive layer 422 is not necessary. The organic EL device 450 is formed on a hard substrate via a release layer, and then the substrate 42 is For example, by applying heat, force, laser light, etc. to the peeling layer, After the insulating layer 424 and the organic EL device 450 are peeled off from the hard substrate, the adhesive layer 422 The substrate 420 may be attached to the film 420 using a peeling layer. For example, the insulating film may be a laminated structure of inorganic films including a tungsten film and a silicon oxide film, or a polyimide film. When a hard substrate is used, it is difficult to use an organic resin film such as a resin substrate. Since the insulating layer 424 can be formed at high temperatures, the insulating layer 424 can be made dense and extremely An insulating film with high barrier properties can be obtained.

[0243] [Configuration example 2 of light-emitting device] FIG. 3A shows a cross-sectional view of a light-emitting device. The light-emitting device shown in FIG. The light emitting device is an active matrix type in which the substrate and the substrate are electrically connected.

[0244] The light emitting device shown in FIG. 3A includes a substrate 201, a transistor 210, a light emitting device 203R, and a light emitting Optical device 203G, light-emitting device 203B, color filter 206R, color filter 206G, a color filter 206B, a substrate 205, etc.

[0245] In FIG. 3A, a transistor 210 is provided on a substrate 201, and an insulating layer is provided on the transistor 210. An insulating layer 202 is provided, and light emitting devices 203R, 203G, and 203B are provided on the insulating layer 202. It is provided.

[0246] The transistor 210 and the light emitting devices 203R, 203G, and 203B are mounted on the substrate 201. , the substrate 205, and the adhesive layer 208. 07 can be applied to, for example, a reduced pressure atmosphere, an inert atmosphere, or a resin-filled configuration. .

[0247] In the light-emitting device shown in FIG. 3A, one pixel is composed of a red sub-pixel (R), a green sub-pixel (G), and a and a blue sub-pixel (B).

[0248] A light-emitting device according to one embodiment of the present invention has a plurality of pixels arranged in a matrix. A pixel has one or more sub-pixels. One sub-pixel has one light-emitting device. For example, For example, a pixel may have three sub-pixels (three colors of R, G, and B, or yellow (Y), cyan (C), and magenta (M), or a structure with four sub-pixels (R, G, , B, and white (W), or four colors (R, G, B, Y, etc.) can be applied.

[0249] FIG. 3B shows light-emitting device 203R, light-emitting device 203G, and light-emitting device 203B. The light-emitting devices 203R, 203G, and 203B share a common EL layer 21. 3, and the optical distance between the electrodes of each light-emitting device is adjusted according to the light-emitting color of each light-emitting device. The EL layer 213 has a microcavity structure in which the thickness is adjusted. It is preferable that the light-emitting layer contains an organic compound according to one embodiment of the present invention. For example, It is preferable that one or both of the materials of the electron transport layer contain the organic compound.

[0250] The first electrode 211 functions as a reflective electrode, and the second electrode 215 functions as a semi-transmissive and semi-reflective electrode. It functions as:

[0251] The light emitting device 203R has a first electrode 211 and a second electrode 212 so that the intensity of red light is enhanced. The distance between the light emitting device and the electrode 215 is adjusted to be an optical distance 220R. The first electrode 211 and the second electrode 215 are connected to the light source 203G so that the intensity of the green light is increased. The light emitting device 203B is adjusted so that the optical distance between the light emitting device 203B and the light emitting device 203B is 220G. To enhance the intensity, the first electrode 211 and the second electrode 215 are separated by an optical distance 220B. It is adjusted so that

[0252] As shown in FIG. 3B, in the light-emitting device 203R, the conductive layer 212R is connected to the first electrode 211. In the light-emitting device 203G, a conductive layer 212G is formed on the first electrode 211. Furthermore, in the light-emitting device 203B, A conductive layer having a thickness different from that of the conductive layer 212R and the conductive layer 212G is formed on the first electrode 211. As shown in FIG. 3A, the first electrode 21 1. The ends of the conductive layer 212R and the conductive layer 212G are covered with the insulating layer 204.

[0253] The light emitting device shown in FIG. 3A is a light emitting device in which light emitted from the light emitting device is converted into each color formed on the substrate 205. It is a top-emission type light-emitting device in which light is emitted through a color filter. The filter allows certain wavelengths of visible light to pass and blocks certain wavelengths. .

[0254] In the red sub-pixel (R), light emitted from the light-emitting device 203R is reflected by the red color filter 2 3A, the light is emitted through the light emitting device 206R. By providing a color filter 206R that passes only the red wavelength range, the light-emitting device Red light can be obtained from 203R.

[0255] Similarly, in the green subpixel (G), the light emitted from the light-emitting device 203G is a green color filter. The blue subpixel (B) emits light from the light-emitting device 203B through the filter 206G. The emitted light is emitted through the blue color filter 206B.

[0256] In addition, a black matrix 209 (also called a black layer) is provided at the edge of one type of color filter. Furthermore, color filters of each color and a black matrix may be provided. 209 may be covered with an overcoat layer that transmits visible light.

[0257] In the light-emitting device shown in FIG. 3C, one pixel has a red sub-pixel (R), a green sub-pixel (G), and a blue In FIG. 3C, the white sub-pixel (W) is The light from the light emitting device 203W of the pixel (W) is emitted through the light emitting device without passing through a color filter. It is ejected outside the device.

[0258] In addition, the optical fiber between the first electrode 211 and the second electrode 215 in the light-emitting device 203W is The distance may be the same as any of the light emitting devices 203R, 203G, 203B, It may be different from either one.

[0259] For example, the light emitted from the light-emitting device 203W may be white light with a low color temperature, and the light may be blue. When it is desired to increase the intensity of light of the wavelength, as shown in FIG. 3C, It is preferable to make the optical distance at the light emitting device 203B equal to the optical distance 220B at the light emitting device 203B. This allows the light obtained from the light emitting device 203W to be closer to white light with a desired color temperature. It can be attached.

[0260] FIG. 3A shows an example in which a common EL layer 213 is used for the light-emitting devices of the sub-pixels of each color. However, as shown in FIG. 4A, the light-emitting devices of the subpixels of each color have different E The L layer may also be used. The above-mentioned microcavity structure can also be applied to FIG. 4A. Cut.

[0261] In FIG. 4A, light-emitting device 203R has EL layer 213R, and light-emitting device 203G has 10 shows an example in which light-emitting device 203B has EL layer 213B, and light-emitting device 203G has EL layer 213G. The EL layers 213R, 213G, and 213B may have a common layer. 213R, 213G, and 213B have different light-emitting layer configurations, but the other layers are common layers. In FIG. 4A, the light emitted by the light-emitting devices 203R, 203G, and 203B may be The light may be extracted through a color filter or may be extracted without a color filter. Good too.

[0262] In FIG. 3A, a top-emission type light-emitting device is shown. However, as shown in FIG. 4B, A structure in which light is extracted to the substrate 201 side on which the resistor 210 is formed (bottom emission type) ) is also one embodiment of the present invention.

[0263] In a bottom emission type light emitting device, color filters of each color are disposed between the substrate 201 and the light emitting device. In FIG. 4B, a transistor 210 is preferably provided on a substrate 201. An insulating layer 202a is formed on the transistor 210, and a color filter is formed on the insulating layer 202a. and forming color filters 206R, 206G, and 206B. An insulating layer 202b is formed on the insulating layer 202b, and light-emitting devices 203R and 203 G, 203B is shown as an example.

[0264] In the case of a top emission type light emitting device, the substrate 201 is a light-shielding substrate and a light-transmitting substrate. The substrate 205 can be a light-transmitting substrate.

[0265] In the case of a bottom emission type light emitting device, the substrate 205 is made of a light-shielding substrate and a light-transmitting substrate. The substrate 201 can be a light-transmitting substrate.

[0266] [Configuration example 3 of light-emitting device] The light-emitting device of one embodiment of the present invention is a passive matrix type or an active matrix type. An active matrix light emitting device will be described with reference to FIG.

[0267] 5A shows a top view of the light-emitting device. 5B shows a cross-sectional view of the light-emitting device taken along the dashed line A-A' in FIG. 5A. Shows.

[0268] The active matrix light emitting device shown in FIGS. 5A and 5B includes a pixel section 302, a circuit section 303, and a 3, has circuit portion 304a and circuit portion 304b.

[0269] The circuit section 303, the circuit section 304a, and the circuit section 304b are each a scanning line driving circuit (gate The pixel circuit can function as a gate driver or a signal line driver circuit (source driver). Alternatively, an external gate driver or source driver and the pixel section 302 are electrically connected. It may also be a circuit for connecting.

[0270] On the first substrate 301, a lead wiring 307 is provided. The FPC 308 is electrically connected to the circuit section 303, which is an input terminal of the circuit section 303. The circuit unit 304a and the circuit unit 304b receive external signals (for example, video signals, clock The FPC308 also transmits signals such as pulses, start signals, and reset signals, as well as electrical potentials. The configuration shown in Figures 5A and 5B may be It can also be called a light-emitting module having an optical device (or light-emitting apparatus) and an FPC.

[0271] The pixel section 302 includes an organic EL device 317, a transistor 311, and a transistor 312. The transistor 312 has an organic EL device 317. The transistor 311 is electrically connected to a first electrode 313. The transistor 312 functions as a current control transistor. The number of transistors in each pixel is not particularly limited, and may be increased as needed. It can be provided appropriately depending on the situation.

[0272] The circuit section 303 includes a plurality of transistors, including a transistor 309, a transistor 310, etc. The circuit section 303 has a transistor of a single polarity (either N-type or P-type). It may be formed of a circuit including an N-type transistor and a P-type transistor. It may be formed of a CMOS circuit, or may have an external driver circuit.

[0273] The structure of the transistor included in the light-emitting device of this embodiment is not particularly limited. Uses a staggered transistor, a staggered transistor, an inverted staggered transistor, etc. In addition, either a top-gate type or a bottom-gate type transistor structure can be used. Alternatively, gates may be provided above and below the semiconductor layer where the channel is formed. Good too.

[0274] The crystallinity of the semiconductor material used in the transistor is not particularly limited. A semiconductor with crystallinity (microcrystalline semiconductor, polycrystalline semiconductor, single crystal semiconductor, or semiconductor with a partially crystalline region) If a semiconductor having crystallinity is used, This is preferable because it can suppress deterioration of the resistor characteristics.

[0275] The semiconductor layer of the transistor preferably contains a metal oxide (also called an oxide semiconductor). Alternatively, the semiconductor layer of the transistor may contain silicon. are amorphous silicon, crystalline silicon (low-temperature polysilicon, single-crystal silicon, etc.) ) etc.

[0276] The semiconductor layer may be made of, for example, indium and M (M is gallium, aluminum, silicon, fluorine, etc.). Uron, yttrium, tin, copper, vanadium, beryllium, titanium, iron, nickel, gel Al, zirconium, molybdenum, lanthanum, cerium, neodymium, hafnium, one or more selected from the group consisting of tantalum, tungsten, and magnesium), zinc, In particular, M is aluminum, gallium, yttrium, and sulphur. It is preferable that the organic solvent is one or more selected from the group consisting of:

[0277] In particular, the semiconductor layer contains indium (In), gallium (Ga), and zinc (Zn). It is preferable to use IGZO (Indium Zirconate Oxide).

[0278] When the semiconductor layer is an In-M-Zn oxide, a film of the In-M-Zn oxide is formed. In the sputtering target, the atomic ratio of In is preferably equal to or greater than the atomic ratio of M. The atomic ratio of the metal elements in such a sputtering target is In:M:Zn= 1:1:1, In:M:Zn=1:1:1.2, In:M:Zn=2:1:3, In:M :Zn=3:1:2, In:M:Zn=4:2:3, In:M:Zn=4:2:4.1, In:M:Zn=5:1:6, In:M:Zn=5:1:7, In:M:Zn=5:1: 8, In:M:Zn=6:1:6, In:M:Zn=5:2:5, etc.

[0279] The transistors included in the circuit portion 303, the circuit portion 304a, and the circuit portion 304b, and the pixel portion 302 The transistors in the circuit section may have the same structure or different structures. The structures of the transistors in the circuit section 303, the circuit section 304a, and the circuit section 304b are all the same. Similarly, the pixel portion 302 may have a plurality of transistors. The transistors may all have the same structure, or there may be two or more types.

[0280] The end of the first electrode 313 is covered with an insulating layer 314. , negative photosensitive resin, positive photosensitive resin (acrylic resin), and other organic compounds, Inorganic compounds such as silicon, silicon oxynitride, and silicon nitride can be used. The upper or lower end of the layer 314 preferably has a curved surface. This allows the film formed on the insulating layer 314 to have good coverage.

[0281] An EL layer 315 is provided on the first electrode 313, and a second electrode 316 is provided on the EL layer 315. The EL layer 315 includes a light-emitting layer, a hole-injecting layer, a hole-transporting layer, an electron ... a hole-transporting layer, an electron-transporting layer, an electron-transporting layer, an electron-transporting layer, an electron-transporting layer, an electron-transporting layer, The EL layer 315 includes an insulating layer, a charge generation layer, and the like. It is preferable to have an organic compound, for example, a host material for the light-emitting layer and a material for the electron transport layer. It is preferable that one or both of the above-mentioned organic compounds be contained.

[0282] The plurality of transistors and the plurality of organic EL devices 317 are formed on the first substrate 301, the second substrate 302, and the The first substrate 301 and the second substrate 302 are sealed by a plate 306 and a sealing material 305. The space 318 surrounded by the plate 306 and the sealing material 305 is filled with an inert gas (nitrogen, argon, etc.). ) or organic matter (including the sealant 305).

[0283] The sealing material 305 can be made of epoxy resin or glass frit. It is preferable to use a material that is as impermeable to moisture and oxygen as possible for the sealing material 305. When glass frit is used as the bonding material, the first substrate 301 and The second substrate 306 is preferably a glass substrate.

[0284] 5C and 5D show examples of transistors that can be used in the light-emitting device.

[0285] The transistor 320 shown in FIG. 5C includes a conductive layer 321 that functions as a gate, a gate insulating layer the insulating layer 328, which functions as a channel forming region 327i, and the pair of low resistance regions 327n a conductive layer 322a connected to one of the pair of low resistance regions 327n; The conductive layer 322b connected to the other of the pair of low resistance regions 327n functions as a gate insulating layer. the insulating layer 325 that functions as a gate, the conductive layer 323 that functions as a gate, and the insulating layer 325 that covers the conductive layer 323. The insulating layer 328 is formed between the conductive layer 321 and the channel forming region 327i. The insulating layer 325 is located between the conductive layer 323 and the channel forming region 327i. The transistor 320 is preferably covered by an insulating layer 326. 26 may be included as a component of the transistor 320.

[0286] The conductive layer 322a and the conductive layer 322b are respectively connected to each other through openings provided in the insulating layer 324. One of the conductive layer 322a and the conductive layer 322b is connected to the low resistance region 327n. One acts as a source and the other acts as a drain.

[0287] The insulating layer 325 is provided to overlap at least the channel formation region 327i of the semiconductor layer. The insulating layer 325 may cover the top and side surfaces of the pair of low resistance regions 327n.

[0288] The transistor 330 shown in FIG. 5D includes a conductive layer 331 that functions as a gate, a gate insulating layer the insulating layer 338 serving as the source and drain; the conductive layer 332a and the conductive layer 332b serving as the source and drain; The insulating layer 335 functions as a gate insulating layer. The insulating layer 338 is formed between the conductive layer 331 and the semiconductor layer 332. The insulating layer 335 is located between the conductive layer 333 and the semiconductor layer 337. The transistor 330 is preferably covered by an insulating layer 334. 334 may be included in the components of transistor 330.

[0289] The transistor 320 and the transistor 330 each have two semiconductor layers in which channels are formed. The structure is applied in which two gates are connected and the same signal is applied to them. Alternatively, one of the two gates may be driven by supplying By applying a potential to one side to control the threshold voltage and a potential to the other side to drive the transistor, The threshold voltage of the transistor may be controlled.

[0290] At least one insulating layer covering the transistor is made of a material that is resistant to the diffusion of impurities such as water and hydrogen. It is preferable to use a material such that the insulating layer can function as a barrier layer. This structure effectively prevents impurities from diffusing into the transistor from the outside. This can effectively suppress the occurrence of light, thereby improving the reliability of the light emitting device.

[0291] Insulating layer 325, insulating layer 326, insulating layer 328, insulating layer 334, insulating layer 335, and insulating layer It is preferable to use an inorganic insulating film as 338. For example, a silicon nitride film, a silicon oxynitride film, a silicon oxide film, a silicon nitride oxide film, An aluminum oxide film, an aluminum nitride film, or the like can be used. um film, yttrium oxide film, zirconium oxide film, gallium oxide film, tantalum oxide film, Magnesium oxide film, lanthanum oxide film, cerium oxide film, neodymium oxide film, etc. Two or more of the above insulating films may be stacked.

[0292] Materials that can be used for various conductive layers that constitute the light-emitting device include aluminum. , titanium, chromium, nickel, copper, yttrium, zirconium, molybdenum, silver, tungsten Examples include metals such as aluminum or tungsten, or alloys containing these as the main components. In addition, films containing these materials can be used as a single layer or as a laminated structure. For example, a single layer structure of an aluminum film containing silicon, or a structure in which an aluminum film is laminated on a titanium film, Two-layer structure: Two-layer structure with aluminum film laminated on tungsten film, copper-magnesium- Two-layer structure with copper film laminated on aluminum alloy film, two-layer structure with copper film laminated on titanium film , a two-layer structure in which a copper film is laminated on a tungsten film, a titanium film or titanium nitride film, and An aluminum film or copper film is laminated on top of the aluminum film, and then a titanium film or titanium nitride film is laminated on top of that. Three-layer structure that forms a film: molybdenum film or molybdenum nitride film, and aluminum layer on top of it. A tungsten film or copper film is laminated, and then a molybdenum film or molybdenum nitride film is formed on top of that. There are three-layer structures, etc., which are made up of oxides such as indium oxide, tin oxide, or zinc oxide. Furthermore, when copper containing manganese is used, the controllability of the shape by etching is improved. This is preferable.

[0293] This embodiment mode can be combined with other embodiment modes as appropriate.

[0294] (Fourth embodiment) In this embodiment, electronic devices of one embodiment of the present invention will be described with reference to drawings.

[0295] Examples of electronic devices include television sets, computer monitors, digital Cameras, digital video cameras, digital photo frames, mobile phones (mobile phones, mobile (also called telephone equipment), portable game machines, personal digital assistants, sound reproduction devices, pachinko machines, etc. Examples include large game consoles, biometric authentication devices, and testing equipment.

[0296] Since the electronic device of one embodiment of the present invention includes the light-emitting device of one embodiment of the present invention in a display portion, the light-emitting efficiency can be improved. High rate and high reliability.

[0297] The display unit of the electronic device of this embodiment can display, for example, full high definition, 4K2K, 8K4K, It is possible to display images with a resolution of 16K8K or higher. The display screen size is 20 inches or more diagonally, 30 inches or more diagonally, or 50 inches diagonally. or more, 60 inches or more diagonally, or 70 inches or more diagonally.

[0298] The electronic device of one embodiment of the present invention is flexible, and therefore can be attached to the inner or outer wall of a house or a building. , or can be incorporated along curved surfaces of the interior or exterior of a vehicle.

[0299] Furthermore, the electronic device of one embodiment of the present invention may include a secondary battery and may be configured to use wireless power transmission. It is preferable that the secondary battery can be charged.

[0300] As the secondary battery, for example, a lithium polymer battery (lithium ion battery) using a gel electrolyte is used. Lithium-ion secondary batteries such as lithium polymer batteries, nickel-metal hydride batteries, nickel-cadmium batteries, organic Examples include nickel-zinc batteries, lead-acid batteries, air secondary batteries, nickel-zinc batteries, and silver-zinc batteries. .

[0301] The electronic device according to one embodiment of the present invention may include an antenna. By doing so, it is possible to display images or information on the display unit. In the case where the device has a power supply and a secondary battery, the antenna may be used for contactless power transmission.

[0302] The electronic device of this embodiment includes sensors (force, displacement, position, velocity, acceleration, angular velocity, rotation speed, Distance, light, liquid, magnetism, temperature, chemicals, sound, time, hardness, electric field, current, voltage, power, radiation (including the ability to measure radiation, flow rate, humidity, gradient, vibration, odor or infrared) It may be possible.

[0303] The electronic device of this embodiment can have various functions. For example, Functions for displaying still images, videos, text images, etc. on the display, touch panel function, calendar - Functions to display date or time, etc., and to run various software (programs) Functions, wireless communication functions, and functions for reading programs or data recorded on recording media etc.

[0304] FIG. 6A shows an example of a television device. A television device 7100 is housed in a housing 7101. A display unit 7000 is built in. Here, the housing 7101 is supported by a stand 7103. 1 shows the supported configuration.

[0305] The light-emitting device of one embodiment of the present invention can be applied to the display portion 7000.

[0306] The television device 7100 shown in FIG. 6A is operated by operating the operation switches and the like provided on the housing 7101. This can be done by a separate remote control 7111. Alternatively, the display unit 7000 can be A touch sensor may be provided, and operation may be performed by touching the display unit 7000 with a finger or the like. The remote control unit 7111 has a display that displays information output from the remote control unit 7111. The remote control 7111 may have an operation key or a touch panel. This allows you to operate the channel and volume, and the image displayed on the display unit 7000 can be operated.

[0307] The television device 7100 includes a receiver, a modem, and the like. It is also possible to receive general television broadcasts via wired or wireless connection via a modem. By connecting to a wired communication network, it can be transmitted in one direction (sender to receiver) or two directions. It is also possible to communicate information in two directions (between a sender and a receiver, or between receivers). do.

[0308] FIG. 6B shows an example of a notebook personal computer. The computer 7200 includes a housing 7211, a keyboard 7212, a pointing device 7213, and a , an external connection port 7214, etc. The display unit 7000 is incorporated in the housing 7211. There are.

[0309] The light-emitting device of one embodiment of the present invention can be applied to the display portion 7000.

[0310] 6C and 6D show an example of digital signage.

[0311] The digital signage 7300 shown in FIG. 6C includes a housing 7301, a display unit 7000, and a speaker. In addition, LED lamps, operation keys (power switch, or operation It may have a variety of components, including switches, connection terminals, various sensors, a microphone, etc.

[0312] FIG. 6D shows a digital signage 7400 attached to a cylindrical pole 7401. The signage 7400 has a display unit 7000 provided along the curved surface of a pillar 7401. do.

[0313] 6C and 6D, the light-emitting device of one embodiment of the present invention is applied to the display portion 7000. can be done.

[0314] The larger the display unit 7000, the more information can be displayed at once. The wider the part 7000, the more noticeable it is, and for example, the more effective the advertisement. Cut.

[0315] By applying a touch panel to the display unit 7000, images or videos can be displayed on the display unit 7000. It is also preferable because it not only shows route information but also allows users to operate it intuitively. When used to provide information such as traffic information, intuitive operation is required. Usability can be improved.

[0316] Also, as shown in FIGS. 6C and 6D, the digital signage 7300 or the digital signage The page 7400 is an information terminal 7311 such as a smartphone owned by the user or an information terminal It is preferable that the display unit 7000 can be connected to the terminal device 7411 by wireless communication. The advertisement information displayed on the screen of the information terminal 7311 or the information terminal 7411 is displayed. In addition, the information terminal 7311 or the information terminal 7411 can be operated. The display on the display unit 7000 can be switched by doing this.

[0317] In addition, the digital signage 7300 or the digital signage 7400 is equipped with an information terminal 7 311 or the screen of the information terminal 7411 is used as a control means (controller) to play games. This allows an unspecified number of users to participate in the game at the same time and enjoy it. It is possible.

[0318] 7A to 7F show an example of a portable information terminal having a flexible display unit 7001. FIG.

[0319] The display portion 7001 is manufactured using the light-emitting device of one embodiment of the present invention. Light-emitting devices that can be bent between 0.01 mm and 150 mm can be applied. The display unit 7001 may be provided with a touch sensor, and when the display unit 7001 is touched with a finger or the like, You can operate a mobile information terminal.

[0320] 7A to 7C show an example of a foldable mobile information terminal. In FIG. 7B, the state is changing from one of the unfolded state to the other. 7C shows the portable information terminal 7600 in a folded state. The 600 is highly portable when folded and has a seamless, wide surface when unfolded. The display area provides excellent visibility.

[0321] The display unit 7001 is supported by three housings 7601 connected by hinges 7602. The two housings 7601 are bent via the hinge 7602, and the portable information terminal The 7600 can be reversibly transformed from an unfolded state to a folded state.

[0322] 7D and 7E show an example of a foldable mobile information terminal. In FIG. 7E, the display unit 7001 is on the outside. The portable information terminal 7650 is folded as shown in FIG. When the portable information terminal 7650 is not in use, the display By folding the case so that the display part 7001 is on the inside, the display part 7001 can be protected from dirt and scratches. It can be suppressed.

[0323] FIG. 7F shows an example of a wristwatch-type mobile information terminal. The mobile information terminal 7800 has a band 780 1, a display unit 7001, an input / output terminal 7802, an operation button 7803, etc. The portable information terminal 7800 has a flexible backing. The battery 7805 can be mounted on the display unit 7001 or may be arranged to overlap with the band 7801.

[0324] The band 7801, the display portion 7001, and the battery 7805 are flexible. The portable information terminal 7800 can be easily bent into a desired shape.

[0325] The operation button 7803 is used to set the time, turn the power on and off, and turn wireless communication on and off. It has various functions such as operation, silent mode activation and deactivation, power saving mode activation and deactivation, etc. For example, an operating system installed in the portable information terminal 7800 can The function of the operation button 7803 can also be freely set using the stem.

[0326] In addition, by touching an icon 7804 displayed on the display unit 7001 with a finger or the like, the application You can launch the application.

[0327] In addition, the mobile information terminal 7800 is capable of performing standardized short-range wireless communication. For example, by communicating with a wireless headset, hands-free operation is possible. You can also make calls.

[0328] The portable information terminal 7800 may also have an input / output terminal 7802. If you have a 02, you can exchange data directly with other information terminals via a connector. Charging can also be performed via the input / output terminal 7802. The charging operation of the mobile information terminal shown in is performed by non-contact power transmission without using input / output terminals. That's fine.

[0329] FIG. 8A shows the exterior of the automobile 9700. FIG. 8B shows the driver's seat of the automobile 9700. 9700 is the body 9701, wheels 9702, windshield 9703, lights 9704, The light-emitting device of one embodiment of the present invention includes a display of the automobile 9700. For example, the display portions 9710 to 9715 shown in FIG. The light-emitting device of one embodiment of the present invention can be provided in the light 9704 or the photosensitive drum. The light-emitting device of one embodiment of the present invention may be used for the lamp 9705.

[0330] The display portion 9710 and the display portion 9711 are display devices provided on a windshield of an automobile. In the light-emitting device of one embodiment of the present invention, electrodes and wirings are formed using a light-transmitting conductive material. This allows the opposite side to be seen through, creating a so-called see-through state. If the display unit 9710 or the display unit 9711 is in a see-through state, the driver of the car 9700 Therefore, the light-emitting device of one embodiment of the present invention can be mounted on an automobile 970 It can be installed on the windshield of a car. When a transistor or the like is provided, an organic transistor using an organic semiconductor material or an oxide semiconductor A light-transmitting transistor, such as a conductor transistor, is preferably used.

[0331] The display unit 9712 is a display device provided in a pillar part. By displaying an image from the imaging means on the display unit 9712, the view blocked by the pillars can be compensated for. The display unit 9713 is a display device provided in the dashboard. For example, an image captured by an imaging means provided on the vehicle body is displayed on the display unit 9713. This allows the driver to compensate for the obstructed view of the dashboard. By projecting images from the installed imaging means, blind spots can be compensated for and safety can be improved. In addition, by projecting images that complement the invisible parts, it is possible to make the sense of incongruity appear more natural. Safety checks can be performed without any need for manual intervention.

[0332] FIG. 8C shows the interior of a car with bench seats for the driver and passenger seats. The display unit 9721 is a display device provided in the door section. By displaying the image from the means on the display unit 9721, the view blocked by the door is complemented. The display unit 9722 is a display device provided on the handle. The display unit 9723 is a display device provided in the center of the seat surface of the bench seat. The display device is installed on the seat or backrest, and the heat generated by the display device is dissipated in a It can also be used as a seat heater powered by electricity.

[0333] The display unit 9714, the display unit 9715, or the display unit 9722 displays navigation information, It can display the odometer, tachometer, mileage, fuel gauge, gear status, air conditioning settings, etc. In addition, various information can be provided by displaying the items and layout displayed on the display unit. The above information can be changed as needed to suit the user's preferences. The display units 9710 to 9713, the display unit 9721, and the display unit 9723 may also display the In addition, the display units 9710 to 9715, the display units 9721 to 9722 The display units 9710 to 9715 can also be used as lighting devices. The display portions 9721 to 9723 can also be used as heating devices.

[0334] Furthermore, since the electronic device of one embodiment of the present invention includes the light-emitting device of one embodiment of the present invention as a light source, For example, the present invention can be applied to a light source that emits visible light or near-infrared light. The light-emitting device of one embodiment of the present invention can be used as a lighting device. It can also be used as a light source for equipment.

[0335] FIG. 9A shows a biometric authentication device for finger veins, which includes a housing 911, a light source 912, a detection stage 913, and a sensor 914. The detection stage 913 is used to capture an image of the shape of veins by placing a finger on the detection stage 913. A light source 912 that emits near-infrared light is installed above the detection stage 913. The detection stage 913 is made of a material that transmits near-infrared light. The near-infrared light emitted from the light source 912 and transmitted through the finger is captured by the image pickup device 914. An optical system is provided between the detection stage 913 and the imaging device 914. The above-mentioned device configuration may be used in a biometric authentication device targeting palm veins. You can also do this.

[0336] The light-emitting device of one embodiment of the present invention can be used as the light source 912. The device can be installed in a curved shape and can irradiate the object with light uniformly. In particular, the peak intensity is strongest in the wavelength range of 700 nm to 1200 nm. It is preferable that the light emitting device emits infrared light. The light is received by the finger or palm. By imaging the blood vessels, the location of the veins can be detected. This effect can be used as biometric authentication. In addition, by combining it with the global shutter system, it is possible to capture images without subject movement. Even if there is a problem, highly accurate sensing is possible.

[0337] The light source 912 may have a plurality of light emitting units, such as light emitting units 915, 916, and 917 shown in FIG. 9B. Each of the light emitting portions 915, 916, and 917 can have an emission wavelength of They may be different, and each may be irradiated at a different time. By changing the wavelength and angle of the irradiated light, different images can be captured continuously. This allows multiple images to be used for authentication, achieving high security.

[0338] FIG. 9C shows a biometric authentication device for palm veins, which includes a housing 921, an operation button 92 2, a detection unit 923, a light source 924 that emits near-infrared light, etc. By doing so, the shape of the veins in the palm of your hand can be recognized. A light source 924 is arranged around the detection unit 923. The object (hand) is illuminated with the light, and the light reflected from the object is incident on the detection unit 923. The light-emitting device of this embodiment can be used as the light source 924. The detection unit 925 is placed on the hand and can capture an image of the object (the entire image of the hand). An optical system may be provided between the image sensor 923 and the image sensor 925. It can also be used in biometric authentication devices that target veins.

[0339] FIG. 9D shows a non-destructive testing device, which includes a housing 931, an operation panel 932, a transport mechanism 933, a monitor, and The sensor 934 includes a sensor unit 935, a light source 938 that emits near-infrared light, and the like. A light emitting device similar to the above can be used as the light source 938. The inspected member 936 is conveyed by the conveying mechanism 933. The inspected member 936 is irradiated with near-infrared light from a light source 938. Light is irradiated, and the transmitted light is captured by an imaging device 937 provided in the detection unit 935. The captured image is displayed on a monitor 934. After that, the camera is carried to the exit of the housing 931. The product is transported to the factory, and defective products are separated and collected. This allows for non-destructive, high-speed detection of defects and foreign matter.

[0340] FIG. 9E shows a mobile phone, which includes a housing 981, a display unit 982, an operation button 983, and an external connection port. port 984, speaker 985, microphone 986, first camera 987, second camera 988 The mobile phone includes a touch sensor in a display portion 982. The display unit 982 is flexible. The operation can be performed by touching the display unit 982 with a finger or a stylus. The first camera 987 can capture visible light images, and the second camera 988 can capture infrared light images (nearby). The mobile phone or display unit 982 shown in FIG. 9E can acquire an infrared image. The light-emitting device according to one embodiment of the present invention may be included.

[0341] This embodiment mode can be combined with other embodiment modes as appropriate. [Example]

[0342] (Synthesis Example 1) In this example, a method for synthesizing an organic compound according to one embodiment of the present invention will be described. 10-[(3'-dibenzothiophene-4-yl)-4-methyl-2-(2-methyl-1-propanol)-4-one represented by the structural formula (100) of the first embodiment -yl)biphenyl-3-yl]naphtho[1',2':4,5]furo[2,3-b]quino The synthesis method of xaline (abbreviation: 10mDBtBPNfqn) will be explained.

[0343] [ka]

[0344] Step 1: 7-chloro-3-(2-methoxynaphthalen-1-yl)quinoxaline Synthesis of 2-amines First, 2.49 g of 3,7-dichloroquinoxalin-2-amine, 2-methoxynaphthalene 2.38 g of 1-boronic acid, 3.90 g of cesium carbonate, 46 mL of 1,4-dioxane, and 23 mL of water was placed in a three-necked flask equipped with a reflux condenser, and the inside of the flask was replaced with nitrogen. After degassing by stirring under reduced pressure, tetrakis(triphenylphosphine)palladium was added. Add 1.38 g of Pd(PPh3)4 (abbreviation: Pd(PPh3)4) and stir at 80°C for 6 hours. made him do so.

[0345] The solution after the reaction was extracted with dichloromethane to obtain a residue. The mixture was purified by silica gel column chromatography using dichloromethane: ethyl acetate = 50:1 as a developing solvent. The target quinoxaline derivative was obtained (yellow solid, yield 2.89 g) by filtration. The synthesis scheme for step 1 is shown in (a-1).

[0346] [ka]

[0347] Step 2: 10-chloronaphtho[1',2':4,5]furo[2,3-b]quinoxa Phosphorus Synthesis Next, 7-chloro-3-(2-methoxynaphthalen-1-yl)quinoxazone obtained in step 1 2.89 g of salin-2-amine, 90 mL of dehydrated tetrahydrofuran, and 90 mL of glacial acetic acid L was placed in a three-neck flask and the inside was replaced with nitrogen. After cooling the flask to -10°C, nitrous acid 3.0 mL of tert-butyl acetate was added dropwise, and the mixture was stirred at -10°C for 1 hour and at 0°C for 18 hours. After the specified time has elapsed, 400 mL of water is added to the resulting suspension, and the suspension is filtered by suction to obtain the desired The quinoxaline derivative was obtained (yellow-white solid, 1.63 g, yield 64%). The synthesis scheme is shown in (a-2).

[0348] [ka]

[0349] <Step 3: Synthesis of 10mDBtBPNfqn> Furthermore, 10-chloronaphtho[1',2':4,5]furo[2,3-b ]Quinoxaline 1.63g, 3'-(4-dibenzothiophene)-1,1'-biphenyl -3-boronic acid 3.29g, potassium phosphate tripotassium 5.48g, tert-butyl alcohol 1.42 g, diethylene glycol dimethyl ether (abbreviated as diglyme) 60 mL The contents of the flask were stirred under reduced pressure to degas the contents. Then, 0.10 g of palladium acetate (II) (abbreviation: Pd(OAc)2) and di(1-ad Add 0.32 g of manthyl-n-butylphosphine (abbreviation: CataCXium A) The mixture was stirred at 140°C for 31.5 hours to react.

[0350] After a predetermined time had passed, the resulting suspension was filtered by suction and washed with water and ethanol. The body was dissolved in toluene and passed through a filter aid consisting of layers of celite, alumina, and celite. After filtering, the target product was obtained by recrystallization from toluene (yellow solid, yield 2.1%). 9g, 69% yield.

[0351] The resulting yellow solid (2.19 g) was purified by train sublimation. The purification conditions were a pressure of 2.7 Pa, argon gas flow rate of 15 mL / min, and 34 The solid was heated at 0°C. After purification by sublimation, the target yellow solid was obtained in an amount of 1.48 g, a yield of 68%. The synthesis scheme for step 3 is shown in (a-3).

[0352] [ka]

[0353] Nuclear magnetic resonance spectroscopy of the yellow solid obtained in step 3 ( 1 The analysis results by H-NMR are shown below. As shown below. 1 The H-NMR chart is shown in Figure 10. From this result, in this example, As a result, 10mDBtBPNfqn shown in structural formula (100) was obtained.

[0354] 1 H-NMR.δ(CDCl3):7.47-7.50(m,2H),7.60-7. 62(m,2H),7.67(t,3H),7.78-7.80(m,3H),7.85 -7.90(m,4H),8.07(d,1H),8.13(d,2H),8.19-8 .23(m,4H),8.49-8.51(m,2H),9.39(d,1H).

[0355] Next, the ultraviolet-visible absorption spectrum of 10mDBtBPNfqn in toluene solution (hereinafter, The absorption spectrum (simply referred to as "absorption spectrum") and emission spectrum are shown in Figure 11A. The horizontal axis is the wavelength, and the vertical axis is the The axes represent the absorption intensity and emission intensity. was carried out at room temperature.

[0356] The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (JASCO Corporation, V550 model). The absorption spectrum of 10mDBtBPNfqn in toluene solution was The absorption spectrum obtained by measuring a toluene solution of PNfqn in a quartz cell shows that The absorption spectrum was calculated by subtracting the absorption spectrum obtained by measuring toluene in a quartz cell. The emission spectrum was measured using a fluorometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.). The emission spectrum of 10mDBtBPNfqn in toluene solution was A toluene solution of Nfqn was placed in a quartz cell and measured.

[0357] As shown in Figure 11A, in the toluene solution of 10mDBtBPNfqn, the peaks around 387 nm and 40 An absorption peak was observed around 6 nm, and around 422 nm and 443 nm (excitation wavelength: 29 A peak in the emission wavelength was observed at 2 nm.

[0358] Next, the absorption and emission spectra of the solid thin film of 10mDBtBPNfqn were measured. The solid thin film was prepared on a quartz substrate by vacuum deposition. The absorption spectrum of the thin film was , absorbance (-log 10 [%T / (100-% R), where %T represents transmittance and %R represents reflectance. An ultraviolet-visible spectrophotometer (Hitachi High-Technologies Corporation, U-4100) was used. The emission spectrum was measured using a fluorometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.). The absorption and emission spectra were measured at room temperature. The measurement results of the absorption spectrum and emission spectrum of the thin film are shown in Figure 11B. The horizontal axis is the wavelength, and the vertical axis is the The axes represent absorption and emission intensities.

[0359] From the results of Figure 11B, in the solid thin film of 10mDBtBPNfqn, An absorption peak is observed around 18 nm, and an emission peak is observed around 514 nm (excitation wavelength: 400 nm). A long peak was observed.

[0360] The organic compound 10mDBtBPNfqn according to one embodiment of the present invention emits light in red and longer wavelengths. It was found that this is a suitable host material for phosphorescent materials that emit light at energies near 10mD. BtBPNfqn is a visible light-emitting material (fluorescent material, delayed fluorescent material, phosphorescent material, etc.) ) and can also be used as a host material in combination with other compounds, or as a light-emitting material.

[0361] In addition, differential scanning calorimetry was performed on 10mDBtBPNfqn. A measuring device (Pyris 1, manufactured by PerkinElmer Japan Co., Ltd.) was used. The temperature was raised from 10°C to 350°C at a rate of 40°C / min, and then held at 350°C for 3 minutes. After that, the temperature was decreased from 350°C to -10°C at a rate of 100°C / min. This constituted one cycle. In this example, three cycles of measurement were carried out. The glass transition temperature (Tg) was 126°C based on the results of the third temperature rise. Therefore, the 10mDBtBPNfqn synthesized in this example is a highly heat-resistant material. It turned out to be a fee.

[0362] The Tg of 10mDBtBPNfqn is 126°C, which improves the heat resistance of light-emitting devices. It is possible.

[0363] 10mDBtBPNfqn is Ar in general formula (G0) 1 is an unsubstituted naphthalene ring This is an example of a certain case. 1 The naphthalene ring lowers the T1 level, and the LU Since the MO level can be deepened, it can be used for materials that emit light in the red and longer wavelengths. It is believed that a suitable host material has been synthesized.

[0364] 10mDBtBPNfqn is a compound having a hole-transporting skeleton or This is an example of a compound having a dibenzothiophene skeleton as a condensed ring. It is believed that the presence of an phenyl ring allows the synthesis of an organic compound with high chemical stability and heat resistance. can be obtained. [Example]

[0365] In this example, the results of manufacturing a light-emitting device according to one embodiment of the present invention will be described. The compound used in Example 1 was 10-[(3'-dibenzothiophen-4-yl)biphenyl] -3-yl]naphtho[1',2':4,5]furo[2,3-b]quinoxaline (abbreviation: 1 Structure of light-emitting device 1 using 0mDBtBPNfqn (structural formula (100)) as the light-emitting layer The fabrication method and characteristics of the film will be described.

[0366] The structure of the light-emitting device 1 used in this example is shown in FIG. 12, and the specific configuration is shown in Table 1. The chemical formulas of the materials used in this example are shown below.

[0367] [Table 1]

[0368] [ka]

[0369] <<Fabrication of Light-Emitting Device 1>> The light-emitting device 1 shown in this example has a first electrode 801 on a substrate 800 as shown in FIG. A hole injection layer 811, a hole transport layer 812, and a light emitting layer 813 are formed on the first electrode 801. , an electron transport layer 814, and an electron injection layer 815 are sequentially stacked, and a second The electrode 803 has a laminated structure.

[0370] First, a first electrode 801 was formed on a substrate 800. The electrode area was 4 mm 2 (2mm x 2 The substrate 800 was a glass substrate. The first electrode 801 was made of silicon oxide. Indium tin oxide (ITSO) containing ZnO was deposited by sputtering to a thickness of 70 nm. In this example, the first electrode 801 functions as an anode.

[0371] Here, as a pretreatment, the surface of the substrate is washed with water, baked at 200°C for 1 hour, and then UV- The treatment was carried out for 370 seconds. -4 Vacuum deposition equipment with the inside pressure reduced to about Pa The substrate was placed in the vacuum deposition chamber and vacuum baked at 170°C for 30 minutes. After this, the substrate was allowed to cool for about 30 minutes.

[0372] Next, a hole injection layer 811 was formed on the first electrode 801. The hole injection layer 811 was formed by vacuum evaporation. 10 in the receiving device -4 After reducing the pressure to 100 Pa, 1,3,5-tri(dibenzothiophene-4-yl) DBT3P-II: benzene (abbreviation: DBT3P-II) and molybdenum oxide The molybdenum oxide was co-deposited at a mass ratio of 2:1 to form a film with a thickness of 80 nm. .

[0373] Next, a hole transport layer 812 was formed on the hole injection layer 811. The hole transport layer 812 was formed of N-( 1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole- 3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PC BBiF) was vapor deposited to a thickness of 20 nm.

[0374] Next, a light-emitting layer 813 was formed on the hole-transporting layer 812. The organic compound 10mDBtBPNfqn is used as the assist material, and PCB BiF was used as the guest material (phosphorescent material), and (acetylacetonato)bis(2,3- Diphenylquinoxalinato-N,C2')iridium(III) (abbreviation: [Ir(dpq )2(acac)]) was used in a weight ratio of 10mDBtBPNfqn:PCBBiF:[I The vapor deposition was carried out so that the ratio of r(dpq)2(acac)] was 0.8:0.2:0.1. The film thickness was 40 nm.

[0375] Next, an electron transport layer 814 was formed on the light-emitting layer 813. The electron transport layer 814 was formed by 10 mDB The thickness of tBPNfqn is 30 nm, and 2,9-bis(naphthalen-2-yl)-4,7-di The film thickness of phenyl-1,10-phenanthroline (NBphen) is 15 nm. The layers were formed by sequential deposition as follows:

[0376] Next, the electron injection layer 815 was formed on the electron transport layer 814. The electron injection layer 815 was formed using a fluoride Lithium (LiF) was used and was formed by vapor deposition to a film thickness of 1 nm.

[0377] Next, the second electrode 803 was formed on the electron injection layer 815. The second electrode 803 was made of aluminum. The film was formed by vapor deposition so as to have a thickness of 200 nm. Thus, the second electrode 803 functions as a cathode.

[0378] By the above steps, a light-emitting device is formed on the substrate 800, with an EL layer sandwiched between a pair of electrodes. The hole injection layer 811, the hole transport layer 812, and the light emitting layer 813 described in the above steps were formed. The electron transport layer 814 and the electron injection layer 815 function to form the EL layer in one embodiment of the present invention. In addition, the deposition process in the above-mentioned manufacturing method is all performed by the resistance heating method. The method was used.

[0379] The light-emitting device fabricated as described above is sealed with another substrate (not shown). When sealing using another substrate (not shown), the device is sealed in a glove box with a nitrogen atmosphere. In this case, another substrate (not shown) coated with an adhesive that hardens when exposed to ultraviolet light is placed on the substrate 800. and the substrate 800 is fixed to the substrate 800 so that the adhesive adheres to the periphery of the light emitting device formed on the substrate 800. During sealing, 365 nm ultraviolet light was applied at 6 J / cm. 2 Irradiation is applied to harden the adhesive. The adhesive was stabilized by heat treatment at 80°C for 1 hour.

[0380] <Operating characteristics of light-emitting device 1> The operating characteristics of the light-emitting device 1 were measured. The measurements were carried out in an atmosphere maintained at room temperature (25°C). I went there with a feeling of excitement.

[0381] FIG. 13 shows the current density-luminance characteristics of the light-emitting device 1. FIG. FIG. 15 shows the luminance-current efficiency characteristics of the light-emitting device 1. FIG. 16 shows the luminance-current efficiency characteristics of the light-emitting device 1. 17 shows the voltage-current characteristics of the light-emitting device 1. FIG. 17 shows the brightness-external quantum Efficiency characteristics are shown.

[0382] Table 2 shows 600cd / m 2 1 shows the main initial characteristic values ​​of the light-emitting device 1 in the vicinity of the luminance.

[0383] [Table 2]

[0384] As shown in FIGS. 13 to 17 and Table 2, it was found that the light-emitting device 1 had high luminous efficiency. Ta.

[0385] In addition, 2.5 mA / cm2 was applied to light-emitting device 1. 2 The emission spectrum when a current is applied at a current density of 18. As shown in FIG. 18, the light-emitting device 1 includes a light-emitting layer 813. The maximum peak is around 680 nm, which is due to the emission of [Ir(dpq)2(acac)]. The emission spectrum showed

[0386] Next, a reliability test was carried out on the light-emitting device 1. The results of the reliability test are shown in FIG. In FIG. 19, the vertical axis indicates the normalized brightness (%) when the initial brightness is 100%, and the horizontal axis indicates The operating time (h) is shown. The reliability test was performed at a current density of 75 mA / cm 2 Set to The optical device 1 was driven.

[0387] The results of the reliability test showed that the light-emitting device 1 exhibited high reliability. 10mDBtBPNfqn (structural formula (100)), which is an organic compound according to one embodiment of the present invention, This can be said to be an effect of using the compound in the light-emitting layer of the light-emitting device 1.

[0388] The 10mDBtBPNfqn and PCBBiF used in the light-emitting layer of light-emitting device 1 are exciplexes. In the organic compound of one embodiment of the present invention, a hole-transporting skeleton By having a dibenzothiophene skeleton as a base, the HOMO level becomes deeper, and the hole transport property It is thought that the luminescence decomposition rate becomes lower or that the exciplex is easily formed. This suggests that the reliability of the chair has been improved. [Example]

[0389] In this example, the results of manufacturing a light-emitting device according to one embodiment of the present invention will be described. The compound used in Example 1 was 10-[(3'-dibenzothiophen-4-yl)biphenyl] -3-yl]naphtho[1',2':4,5]furo[2,3-b]quinoxaline (abbreviation: 1 0mDBtBPNfqn) (Structural formula (100)) in the light-emitting layer. An optical device 3 was fabricated and its characteristics were measured, and the results will be described.

[0390] The specific configurations of the light-emitting devices 2 and 3 used in this example are shown in Table 3. The structures of devices 2 and 3 are the same as those of light-emitting device 1 (Fig. 12), and the fabrication method is the same as that of the actual device. See Example 2. The chemical formulas of the materials used in this example are shown below.

[0391] [Table 3]

[0392] [ka]

[0393] <Operation characteristics of light-emitting device 2 and light-emitting device 3> The operating characteristics of light-emitting devices 2 and 3 were measured. The measurements were carried out at room temperature (25°C). I went there for the atmosphere.

[0394] FIG. 20 shows the current density-luminance characteristics of light-emitting devices 2 and 3. FIG. 21 shows the current density-luminance characteristics of light-emitting device 2. 22 shows the luminance-current efficiency characteristics of light-emitting devices 2 and 3. Figure 23 shows the voltage-current characteristics of light-emitting devices 2 and 3. Figure 24 shows the voltage-current characteristics of light-emitting device 2. , 3 shows the luminance-external quantum efficiency characteristics.

[0395] Table 4 shows 1000cd / m 2 1 shows the main initial characteristic values ​​of the light-emitting devices 2 and 3 in the vicinity.

[0396] [Table 4]

[0397] As shown in FIGS. 20 to 24 and Table 4, it is clear that light-emitting devices 2 and 3 have high luminous efficiency. It was.

[0398] In addition, 2.5 mA / cm2 is supplied to light-emitting devices 2 and 3. 2 The light emission spectrum when a current is passed at a current density of The spectrum is shown in Figure 25. The light-emitting devices 2 and 3 are made of bis{4, 6-dimethyl-2-[5-(5-cyano-2-methylphenyl)-3-(3,5-dimethyl {2,2,6,6-tetramethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,2,6,6-tetramethylphenyl)-2-pyrazinyl-κN]phenyl-κC} Iridium(III) (abbreviation: [Ir( The maximum peak was observed around 650 nm due to the emission of [(dmdppr-m5CP)2(dpm)]. Specifically, the light-emitting device 2 exhibits an emission spectrum with a peak at around 650 nm. Optical device 3 has a maximum peak near 649 nm.

[0399] Next, reliability tests were conducted on the light-emitting devices 2 and 3. The results of the reliability tests are shown in Figure 26. In Figure 26, the vertical axis indicates the normalized brightness (%) when the initial brightness is 100%, and the horizontal axis indicates the normalized brightness (%) when the initial brightness is 100%. The axis indicates the device operating time (h). The reliability test was performed at a current density of 75 mA / cm 2 to The light emitting devices 2 and 3 were then driven.

[0400] The results of the reliability test showed that the light-emitting devices 2 and 3 exhibited high reliability.

[0401] In this example, the light-emitting device 2 contains N-(4-biphenyl)-N -(9,9-dimethyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazo In the light-emitting device 3, the light-emitting layer 813 is formed of N-(1,1'-biphenyl-4-yl)-N-[4-(dibenzofuran-4-yl)phenyl]- [phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: FrBBiF-I The HOMO level of PCBiF is -5.26 eV, and FrBBiF-I The HOMO level of I is −5.42 eV. When mDBtBPNfqn is used in the light-emitting layer 813, it can be used in combination with either of them. This indicates that it is possible to fabricate light-emitting devices with excellent properties. The HOMO level of the material (assist material) that can be used in combination with Nfqn is suitable. The range of values ​​was wide, indicating that there was a wide range of options for assist materials. [Example]

[0402] In this example, the substitution position (R 1 or R 2 We investigated whether there are differences in the LUMO level and T1 level depending on the substitution position of the The results obtained by the calculation will be explained below.

[0403] In this example, calculations were performed on organic compounds represented by structural formulas (C1) to (C4). .

[0404] [ka]

[0405] For the molecular orbital calculations, Gaussian09 was used as a quantum chemical calculation program. Using 6-311G as the base function and B3LYP as the functional, the singlet ground state ( The structures in the lowest triplet excited state (T1) and S0 were optimized.

[0406] Table 5 shows the calculated values ​​of the LUMO level and T1 level (wavelength).

[0407] [Table 5]

[0408] As shown in Table 5, the organic compounds represented by structural formulas (C1) to (C4) all have a LUMO The level is deep, and the T1 level (wavelength) is found to be around 600 nm. C2) was found to have the deepest LUMO level and the lowest T1 level (longest wavelength).

[0409] The results of this example show that the organic compound of one embodiment of the present invention has a deep LUMO level and a T1 level Since the optical density is low, it is suitable for light-emitting devices (especially light-emitting devices that emit red or near-infrared light). It was suggested that this is the case. [Example]

[0410] (Synthesis Example 2) In this example, a method for synthesizing an organic compound according to one embodiment of the present invention will be described. 12-[(3'-dibenzothiophene-4-yl)-4-methyl-2- ... -yl)biphenyl-3-yl]phenanthro[9',10':4,5]furo[2,3- b] A method for synthesizing quinoxaline (abbreviation: 12mDBtBPPnfqn) will be explained.

[0411] [ka]

[0412] Step 1: 7-chloro-3-(10-methoxyphenanthrene-9-yl)quinoxa Synthesis of Phos-2-amine First, 2.70 g of 3,7-dichloroquinoxalin-2-amine, 10-methoxyphenanthroline Tren-9-boronic acid 3.27g, cesium carbonate 4.22g, 1,4-dioxane 50m 25 mL of ethanol and 25 mL of water were placed in a three-neck flask equipped with a reflux condenser, and the inside of the flask was replaced with nitrogen. After degassing the inside of the scope by stirring under reduced pressure, tetrakis(triphenylphosphine) Add 0.75 g of radium(0) (abbreviation: Pd(PPh3)4) and stir at 80°C for 11 hours. and reacted.

[0413] After a predetermined time had passed, the precipitated solid was filtered by suction and washed with water and ethanol. The desired product was purified by silica gel column chromatography using chloromethane as a developing solvent. A quinoxaline derivative was obtained (yellow solid, yield 3.30 g, 68%). The synthesis scheme is shown in (b-1).

[0414] [ka]

[0415] Step 2: 12-chlorophenanthro[9',10':4,5]furo[2,3-b] Synthesis of quinoxaline> Next, 7-chloro-3-(10-methoxyphenanthrene-9-yl) 3.29 g of quinoxalin-2-amine, 100 mL of dehydrated tetrahydrofuran, and glacial acetic acid 100 mL was placed in a three-neck flask, and the inside was replaced with nitrogen. The flask was cooled to -10°C. Then, 3.1 mL of tert-butyl nitrite was added dropwise, and the mixture was stirred at -10°C for 1 hour and at 0°C for 24 hours. After a predetermined time had passed, 400 mL of water was added to the resulting suspension, and the mixture was filtered by suction. The desired quinoxaline derivative was obtained (yellow solid, yield 2.52 g, 82%). The synthesis scheme of TOP 2 is shown in (b-2).

[0416] [ka]

[0417] <Step 3: Synthesis of 12mDBtBPPnfqn> Furthermore, 12-chlorophenanthro[9',10':4,5]furo[2 ,3-b]quinoxaline 1.19g, 3'-(4-dibenzothiophene)-1,1'-biphenyl Phenyl-3-boronic acid 1.58 g, potassium phosphate tripotassium 2.19 g, tert-butyl phosphate Alcohol 0.76g, diethylene glycol dimethyl ether (abbreviated as diglyme) 27 mL of the solution was placed in a three-necked flask, and the inside of the flask was replaced with nitrogen. After degassing, 15 mg of palladium acetate (II) (abbreviation: Pd(OAc)2) and di(1 -adamantyl)-n-butylphosphine (abbreviation: CataCXium A) 48 mg The mixture was added and reacted at 150°C for 15 hours with stirring.

[0418] After a predetermined time had passed, the resulting suspension was filtered by suction and washed with water and ethanol. The body was dissolved in toluene and passed through a filter aid consisting of layers of celite, alumina, and celite. After filtering, the target product was obtained by recrystallization from toluene (yellow solid, yield 1. 25g, 56% yield.

[0419] The resulting yellow solid (1.24 g) was purified by train sublimation. The purification conditions were a pressure of 2.6 Pa, argon gas flow rate of 10 mL / min, and 38 The solid was heated at 0°C. After purification by sublimation, the target yellow solid was obtained in an amount of 0.85 g, a yield of 69%. The synthesis scheme for step 3 is shown in (b-3).

[0420] [ka]

[0421] Nuclear magnetic resonance spectroscopy of the yellow solid obtained in step 3 ( 1 The analysis results by H-NMR are shown below. As shown below. 1 The H-NMR chart is shown in Figure 27. From this result, in this example, As a result, 12mDBtBPPnfqn shown in structural formula (113) was obtained.

[0422] 1 H-NMR.δ(CDCl3):7.47-7.50(m,2H),7.60-7.6 9(m,4H),7.78-7.94(m,9H),8.12(s,1H),8.15( s,1H),8.19-8.23(m,3H),8.50-8.52(m,2H),8. 65(d,1H),8.81(d,1H),8.85(d,1H),9.49(s,1H ). [Explanation of symbols]

[0423] 101: first electrode, 102: second electrode, 103: EL layer, 103a: EL layer, 103 b: EL layer, 103c: EL layer, 104: charge generation layer, 111: hole injection layer, 112: Hole transport layer, 113: light emitting layer, 114: electron transport layer, 115: electron injection layer, 201: substrate, 202: insulating layer, 202a: insulating layer, 202b: insulating layer, 203B: light-emitting device, 20 3G: Light-emitting device, 203R: Light-emitting device, 203W: Light-emitting device, 204: Insulation layer, 205: substrate, 206B: color filter, 206G: color filter, 206R: Color filter, 207: space, 208: adhesive layer, 209: black matrix, 21 0: transistor, 211: first electrode, 212G: conductive layer, 212R: conductive layer, 213 : EL layer, 213B: EL layer, 213G: EL layer, 213R: EL layer, 215: second electrode Pole, 220B: optical distance, 220G: optical distance, 220R: optical distance, 301: first base Plate, 302: pixel section, 303: circuit section, 304a: circuit section, 304b: circuit section, 305: Sealant, 306: second substrate, 307: wiring, 308: FPC, 309: transistor , 310: transistor, 311: transistor, 312: transistor, 313: first the electrode, 314: insulating layer, 315: EL layer, 316: second electrode, 317: organic EL device Chair, 318: space, 320: transistor, 321: conductive layer, 322a: conductive layer, 32 2b: conductive layer, 323: conductive layer, 324: insulating layer, 325: insulating layer, 326: insulating layer, 3 27: semiconductor layer, 327i: channel formation region, 327n: low resistance region, 328: insulating layer , 330: transistor, 331: conductive layer, 332a: conductive layer, 332b: conductive layer, 33 3: Conductive layer, 334: Insulating layer, 335: Insulating layer, 337: Semiconductor layer, 338: Insulating layer, 4 01: first electrode, 402: EL layer, 403: second electrode, 405: insulating layer, 406: conductive layer conductive layer, 407: adhesive layer, 416: conductive layer, 420: substrate, 422: adhesive layer, 423: burr layer, 424: insulating layer, 450: organic EL device, 490a: substrate, 490b: substrate, 490c: Barrier layer, 800: Substrate, 801: First electrode, 803: Second electrode, 811 : hole injection layer, 812: hole transport layer, 813: light emitting layer, 814: electron transport layer, 815: Child injection layer, 911: housing, 912: light source, 913: detection stage, 914: imaging device, 9 15: light emitting unit, 916: light emitting unit, 917: light emitting unit, 921: housing, 922: operation button, 923: detector, 924: light source, 925: imaging device, 931: housing, 932: operation panel , 933: conveying mechanism, 934: monitor, 935: detection unit, 936: inspected member, 9 37: Imaging device, 938: Light source, 981: Housing, 982: Display unit, 983: Operation button, 984: external connection port, 985: speaker, 986: microphone, 987: first camera, 988: Second camera, 7000: Display unit, 7001: Display unit, 7100: Television Device, 7101: Housing, 7103: Stand, 7111: Remote control unit, 7200: laptop-type personal computer, 7211: chassis, 7212: keyboard, 7213: Interfacing device, 7214: External connection port, 7300: Digital signage, 7 301: Housing, 7303: Speaker, 7311: Information terminal, 7400: Digital signage 7401: Pillar 7411: Information terminal 7600: Mobile information terminal 7601: Housing , 7602: hinge, 7650: mobile information terminal, 7651: non-display part, 7800: mobile information Information terminal, 7801: band, 7802: input / output terminal, 7803: operation button, 7804: Icon, 7805: Battery, 9700: Automobile, 9701: Body, 9702: Wheel, 9703: Windshield, 9704: Light, 9705: Fog lamp, 9710: Front Display, 9711: Display, 9712: Display, 9713: Display, 9714: Display, 9 715: Display section, 9721: Display section, 9722: Display section, 9723: Display section

Claims

1. A material for a light-emitting device, which has a structure in which a fused aromatic ring is fused to a furoquinoxaline skeleton or a thienoquinoxaline skeleton.

2. It has a structure in which a fused aromatic ring is fused to a furoquinoxaline skeleton or a thienoquinoxaline skeleton, A material for a light-emitting device, comprising a furoquinoxaline skeleton or a thienoquinoxaline skeleton having a benzene ring to which a group having a hole-transporting skeleton is bonded.

3. In claim 2, a material for a light-emitting device, wherein the group having a hole-transporting skeleton has at least one of a substituted or unsubstituted diarylamino group, a substituted or unsubstituted fused aromatic hydrocarbon ring, and a substituted or unsubstituted π-excessive fused heteroaromatic ring.

4. It has a structure in which a fused aromatic ring is fused to a furoquinoxaline skeleton or a thienoquinoxaline skeleton, A material for a light-emitting device, in which a group having a fused ring is bonded to a benzene ring possessed by a furoquinoxaline skeleton or a thienoquinoxaline skeleton.

5. In claim 4, The fused ring is at least one of a substituted or unsubstituted fused aromatic hydrocarbon ring and a substituted or unsubstituted π-excessive fused heteroaromatic ring.

6. In claim 4, The fused ring is a substituted or unsubstituted fused heteroaromatic ring having any one of a dibenzothiophene skeleton, a dibenzofuran skeleton, and a carbazole skeleton.

7. In claim 4, The fused ring is a substituted or unsubstituted fused aromatic hydrocarbon ring having any one of a naphthalene skeleton, a fluorene skeleton, a triphenylene skeleton, and a phenanthrene skeleton.

8. In any one of claims 1 to 7, A material for a light-emitting device, which is a material for a light-emitting device that emits red or near-infrared light.

9. A light-emitting device comprising the material for a light-emitting device according to any one of claims 1 to 8.

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